dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-efeb259598b94a4596cd3d86f73616b9 | CN.O=C([O-])O.O=Cc1cc(-c2ccccc2)n(S(=O)(=O)c2cncc(Br)c2)c1>>CN(Cc1cc(-c2ccccc2)n(S(=O)(=O)c2cncc(Br)c2)c1)C(=O)OC(C)(C)C | C(O)([O-])=O.[Na+].CN.[BH4-].[Na+].BrC=1C=C(C=NC1)S(=O)(=O)N1C=C(C=C1C1=CC=CC=C1)C=O>>C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)C1=CC=CC=C1)S(=O)(=O)C=1C=NC=C(C1)Br)=O | [CH3:1][NH2:2].[O-][C:25](=[O:26])[OH:27].O=[CH:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[n:13]([S:14](=[O:15])(=[O:16])[c:17]2[cH:18][n:19][cH:20][c:21]([Br:22])[cH:23]2)[cH:24]1>>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[n:13]([S:14](=[O:15])(=[O:16])[c:17]2... | CN.O=C([O-])O.O=Cc1cc(-c2ccccc2)n(S(=O)(=O)c2cncc(Br)c2)c1 | CN(Cc1cc(-c2ccccc2)n(S(=O)(=O)c2cncc(Br)c2)c1)C(=O)OC(C)(C)C | null | null | O1CCCC1.O.CO | C-C Coupling | OtherReaction | f0b3014ece669517e5ed6889e7013da7c0a115904cabe9db5ebb7116f0744e47 | 3d8ce2b92b61290a79a351e04280a781726e579e49920cac71c26ad6abac8497 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4](-[#16:5]):[c:6]:[c:7]:1.[C;D1;H3:8]-[NH2;D1;+0:9].[O-]-[C;H0;D3;+0:10](=[O;D1;H0:11])-[OH;D1;+0:12]>>[#16:5]-[#7;a:4]1:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:9](-[C;D1;H3:8])-[C;H0;D3;+0:10](=[O;D1;H0:11])-[O;H0;D2;+0:12]-[C:13](-[C;D1;H3:14])(-[C;D1;H3:15])-[C;D1;H3:16]):[c:7]:[c:6... | 48 | [{"value": 48.0, "product": "C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)C1=CC=CC=C1)S(=O)(=O)C=1C=NC=C(C1)Br)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | 1-[(5-Bromopyridin-3-yl)sulfonyl]-5-phenyl-1H-pyrrole-3-carbaldehyde (1.18 g) was dissolved in absolute tetrahydrofuran (15 mL), a 2 mol/L solution (4.6 mL) of methylamine in tetrahydrofuran was added, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was added to a solution of sodium boro... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Carbonic Acid.Primary amine | Carbamic ester.Ether.Boc | null | null | c1cc[nH]c1.c1ccccc1.c1ccncc1 | null | O1CCCC1.O.CO | null | 16 | CN.O=C([O-])O.O=Cc1cc(-c2ccccc2)n(S(=O)(=O)c2cncc(Br)c2)c1>O1CCCC1.O.CO>CN(Cc1cc(-c2ccccc2)n(S(=O)(=O)c2cncc(Br)c2)c1)C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8918e7f0465c4e70aa1632d1106603b5 | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.CS(=O)(=O)c1ccc(B(O)O)cc1>>CN(Cc1cc(-c2ccc(S(C)(=O)=O)cc2)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | BrC1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C.CS(=O)(=O)C1=CC=C(C=C1)B(O)O.C([O-])([O-])=O.[Na+].[Na+].COCCOC>>CN(C(OC(C)(C)C)=O)CC1=CN(C(=C1)C1=CC=C(C=C1)S(=O)(=O)C)S(=O)(=O)C=1C=NC=CC1 | Br[c:6]1[cH:5][c:4]([CH2:3][N:2]([CH3:1])[C:28](=[O:29])[O:30][C:31]([CH3:32])([CH3:33])[CH3:34])[cH:27][n:17]1[S:18](=[O:19])(=[O:20])[c:21]1[cH:22][cH:23][cH:24][n:25][cH:26]1.OB(O)[c:7]1[cH:8][cH:9][c:10]([S:11]([CH3:12])(=[O:13])=[O:14])[cH:15][cH:16]1>>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10... | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.CS(=O)(=O)c1ccc(B(O)O)cc1 | CN(Cc1cc(-c2ccc(S(C)(=O)=O)cc2)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O | C-C Coupling | Suzuki coupling with boronic acids | b71c1accb23fcf6e808cbf7fdd27a50d721fbf67e253875213e991e29cdecd2f | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:1-[#16:6].O-B(-O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]>>[#16:6]-[#7;a:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11] | 64 | [{"value": 64.0, "product": "CN(C(OC(C)(C)C)=O)CC1=CN(C(=C1)C1=CC=C(C=C1)S(=O)(=O)C)S(=O)(=O)C=1C=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.4, "product": "CN(C(OC(C)(C)C)=O)CC1=CN(C(=C1)C1=CC=C(C=C1)S(=O)(=O)C)S(=O)(=O)C=1C=NC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 14 | HOUR | A mixture of tert-butyl {[5-bromo-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (430 mg), 4-(methanesulfonyl)phenylboronic acid (300 mg), tetrakis(triphenylphosphine)palladium (115 mg), sodium carbonate (320 mg), 1,2-dimethoxyethane (10 mL) and water (10 mL) was stirred under a nitrogen atmosphere at 8... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O | 80 | 14 | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.CS(=O)(=O)c1ccc(B(O)O)cc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O>CN(Cc1cc(-c2ccc(S(C)(=O)=O)cc2)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ea940686250b4adf96db68c31ee3f30f | CN(Cc1cc(-c2ccccc2C=O)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C>>CN(Cc1cc(-c2ccccc2CO)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | O.[BH4-].[Na+].CO.C(=O)C1=C(C=CC=C1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C>>OCC1=C(C=CC=C1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C | [CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[CH:13]=[O:14])[n:15]([S:16](=[O:17])(=[O:18])[c:19]2[cH:20][cH:21][cH:22][n:23][cH:24]2)[cH:25]1)[C:26](=[O:27])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32]>>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[CH2:13][... | CN(Cc1cc(-c2ccccc2C=O)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | CN(Cc1cc(-c2ccccc2CO)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | null | null | O1CCCC1 | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 60.3 | [{"value": 60.0, "product": "OCC1=C(C=CC=C1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.3, "product": "OCC1=C(C=CC=C1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | tert-Butyl {[5-(2-formylphenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (218 mg) was dissolved in tetrahydrofuran (2 mL), and sodium borohydride (24 mg) and methanol (1 mL) were added at 0° C. After stirring at the same temperature for 30 min, water was added, and the mixture was extracted with e... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1cc[nH]c1.c1ccccc1.c1ccncc1 | null | O1CCCC1 | null | 0.5 | CN(Cc1cc(-c2ccccc2C=O)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C>O1CCCC1>CN(Cc1cc(-c2ccccc2CO)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-207b1b52ece24842853daa73c4e5df6d | Cc1cc(C)c(B(O)O)c(C)c1.O=Cc1c[nH]c(Br)c1>>Cc1cc(C)c(-c2cc(C=O)c[nH]2)c(C)c1 | BrC1=CC(=CN1)C=O.CC1=C(C(=CC(=C1)C)C)B(O)O.C([O-])([O-])=O.[Cs+].[Cs+].C(C)(C)(C)P(C(C)(C)C)C(C)(C)C.C1(=CC(=CC(=C1)C)C)C>>C1(=C(C(=CC(=C1)C)C)C1=CC(=CN1)C=O)C | OB(O)[c:6]1[c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:16][c:14]1[CH3:15].Br[c:7]1[cH:8][c:9]([CH:10]=[O:11])[cH:12][nH:13]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6](-[c:7]2[cH:8][c:9]([CH:10]=[O:11])[cH:12][nH:13]2)[c:14]([CH3:15])[cH:16]1 | Cc1cc(C)c(B(O)O)c(C)c1.O=Cc1c[nH]c(Br)c1 | Cc1cc(C)c(-c2cc(C=O)c[nH]2)c(C)c1 | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | O | C-C Coupling | Suzuki coupling with boronic acids | b71c1accb23fcf6e808cbf7fdd27a50d721fbf67e253875213e991e29cdecd2f | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc[nH]2)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4](-[C:5]=[O;D1;H0:6]):[c:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9](-[C;D1;H3:10]):[c:11]):[c:12](-[C;D1;H3:13]):[c:14]>>[C;D1;H3:10]-[c:9](:[c:11]):[c;H0;D3;+0:8](-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4](-[C:5]=[O;D1;H0:6]):[c:7]:1):[c:12](-[C;D1;H3:13]):[c:14] | null | [] | null | null | null | null | A mixture of 5-bromo-1H-pyrrole-3-carbaldehyde (0.87 g), 2,4,6-trimethylphenylboronic acid (3.28 g), cesium carbonate (13.0 g), tri-tert-butylphosphine (0.10 g), tris(dibenzylideneacetone)dipalladium (0) (0.23 g) and mesitylene (200 mL) was stirred with heating under reflux for 5 hr. Water was added to the reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1cc[nH]c1 | c1ccccc1.c1cc[nH]c1 | c1ccccc1.c1cc[nH]c1 | HBr.B | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].O | null | null | Cc1cc(C)c(B(O)O)c(C)c1.O=Cc1c[nH]c(Br)c1>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].O>Cc1cc(C)c(-c2cc(C=O)c[nH]2)c(C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3140e6f898ac42889c77ed292f6a60e8 | CSc1ccccc1B(O)O.O=Cc1c[nH]c(Br)c1>>CSc1ccccc1-c1cc(C=O)c[nH]1 | COCCOC.BrC1=CC(=CN1)C=O.CSC1=C(C=CC=C1)B(O)O.C([O-])([O-])=O.[Na+].[Na+]>>CSC1=C(C=CC=C1)C1=CC(=CN1)C=O | OB(O)[c:8]1[c:3]([S:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]1.Br[c:9]1[cH:10][c:11]([CH:12]=[O:13])[cH:14][nH:15]1>>[CH3:1][S:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1-[c:9]1[cH:10][c:11]([CH:12]=[O:13])[cH:14][nH:15]1 | CSc1ccccc1B(O)O.O=Cc1c[nH]c(Br)c1 | CSc1ccccc1-c1cc(C=O)c[nH]1 | null | null | O | C-C Coupling | Suzuki coupling with boronic acids | b71c1accb23fcf6e808cbf7fdd27a50d721fbf67e253875213e991e29cdecd2f | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc[nH]2)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4](-[C:5]=[O;D1;H0:6]):[c:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11](-[#16:12]):[c:13]>>[#16:12]-[c:11](:[c:13]):[c;H0;D3;+0:8](-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4](-[C:5]=[O;D1;H0:6]):[c:7]:1):[c:9]:[c:10] | 69 | [{"value": 69.0, "product": "CSC1=C(C=CC=C1)C1=CC(=CN1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.0, "product": "CSC1=C(C=CC=C1)C1=CC(=CN1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 105 | CELSIUS | 16 | HOUR | 5-Bromo-1H-pyrrole-3-carbaldehyde (174 mg), [2-(methylthio)phenyl]boronic acid (202 mg) and sodium carbonate (254 mg) were suspended in a mixed solvent of 1,2-dimethoxyethane (5 mL) and water (2 mL), and the mixture was sufficiently degassed under a nitrogen atmosphere. Tetrakis(triphenylphosphine)palladium (58 mg) was... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1cc[nH]c1 | c1ccccc1.c1cc[nH]c1 | c1ccccc1.c1cc[nH]c1 | HBr.B | O | 105 | 16 | CSc1ccccc1B(O)O.O=Cc1c[nH]c(Br)c1>O>CSc1ccccc1-c1cc(C=O)c[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9e19db9fdb10451eb6a7563744aa4403 | O=Cc1c[nH]c(Br)c1.OB(O)c1ccccc1Br>>O=Cc1c[nH]c(-c2ccccc2Br)c1 | C([O-])([O-])=O.[Na+].[Na+].BrC1=CC(=CN1)C=O.BrC1=C(C=CC=C1)B(O)O>>BrC1=C(C=CC=C1)C1=CC(=CN1)C=O | Br[c:6]1[nH:5][cH:4][c:3]([CH:2]=[O:1])[cH:14]1.OB(O)[c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[Br:13]>>[O:1]=[CH:2][c:3]1[cH:4][nH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[Br:13])[cH:14]1 | O=Cc1c[nH]c(Br)c1.OB(O)c1ccccc1Br | O=Cc1c[nH]c(-c2ccccc2Br)c1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | C-C Coupling | Suzuki coupling with boronic acids | b71c1accb23fcf6e808cbf7fdd27a50d721fbf67e253875213e991e29cdecd2f | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc[nH]2)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4](-[C:5]=[O;D1;H0:6]):[c:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11](-[Br;D1;H0:12]):[c:13]>>[Br;D1;H0:12]-[c:11](:[c:13]):[c;H0;D3;+0:8](-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4](-[C:5]=[O;D1;H0:6]):[c:7]:1):[c:9]:[c:10] | 32 | [{"value": 32.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By a similar operation as in Reference Example 148 and using 5-bromo-1H-pyrrole-3-carbaldehyde (870 mg), (2-bromophenyl)boronic acid (1.20 g), sodium carbonate (1.27 g) and tetrakis(triphenylphosphine)palladium (289 mg), the title compound was obtained as colorless crystals (yield 396 mg, 32%).
Conditions: See reaction... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | null | O=Cc1c[nH]c(Br)c1.OB(O)c1ccccc1Br>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1>O=Cc1c[nH]c(-c2ccccc2Br)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-386e173fc7a4479bbc240764d2f07c34 | CSc1ccccc1-c1cc(C=O)c[nH]1>>CS(=O)c1ccccc1-c1cc(C=O)c[nH]1 | S(=S)(=O)([O-])[O-].[Na+].[Na+].CSC1=C(C=CC=C1)C1=CC(=CN1)C=O.ClC1=CC(=CC=C1)C(=O)OO>>CS(=O)C1=C(C=CC=C1)C1=CC(=CN1)C=O | [CH3:1][S:2][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1-[c:10]1[cH:11][c:12]([CH:13]=[O:14])[cH:15][nH:16]1>>[CH3:1][S:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1-[c:10]1[cH:11][c:12]([CH:13]=[O:14])[cH:15][nH:16]1 | CSc1ccccc1-c1cc(C=O)c[nH]1 | CS(=O)c1ccccc1-c1cc(C=O)c[nH]1 | null | null | C(C)(=O)OCC | Oxidation | Sulfanyl to sulfinyl | 9edfaf6d72a81452ea8e3a1cdcb10a58409fff36608e97019e7273998b3d5373 | f5f6bb6ca76a2267cd589767b4d67e7a17ab1ac383eeb6143dcd5d92e00e1b6a | c1ccc(-c2ccc[nH]2)cc1 | [C;D1;H3:1]-[S;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[C;D1;H3:1]-[S;H0;D3;+0:2](=[O;D1;H0:6])-[c:3](:[c:4]):[c:5] | 75 | [{"value": 75.0, "product": "CS(=O)C1=C(C=CC=C1)C1=CC(=CN1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.5, "product": "CS(=O)C1=C(C=CC=C1)C1=CC(=CN1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 5-[2-(methylthio)phenyl]-1H-pyrrole-3-carbaldehyde (200 mg) in ethyl acetate (10 mL) was added 3-chloroperbenzoic acid (238 mg) under ice-cooling. After stirring at room temperature for 1 hr, a saturated sodium thiosulfate aqueous solution was added to the reaction mixture, and the mixture was extracte... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfoxide | null | null | c1ccccc1.c1cc[nH]c1 | null | C(C)(=O)OCC | null | 1 | CSc1ccccc1-c1cc(C=O)c[nH]1>C(C)(=O)OCC>CS(=O)c1ccccc1-c1cc(C=O)c[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c265ec438a5a466d9e691a9e841318eb | CSc1ccccc1-c1cc(C=O)c[nH]1.O=C(OO)c1cccc(Cl)c1>>CS(=O)(=O)c1ccccc1-c1cc(C=O)c[nH]1 | S(=S)(=O)([O-])[O-].[Na+].[Na+].CSC1=C(C=CC=C1)C1=CC(=CN1)C=O.ClC1=CC(=CC=C1)C(=O)OO>>CS(=O)(=O)C1=C(C=CC=C1)C1=CC(=CN1)C=O | [CH3:1][S:2][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1-[c:11]1[cH:12][c:13]([CH:14]=[O:15])[cH:16][nH:17]1.Clc1cccc(C(O[OH:3])=[O:4])c1>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1-[c:11]1[cH:12][c:13]([CH:14]=[O:15])[cH:16][nH:17]1 | CSc1ccccc1-c1cc(C=O)c[nH]1.O=C(OO)c1cccc(Cl)c1 | CS(=O)(=O)c1ccccc1-c1cc(C=O)c[nH]1 | null | null | C(C)(=O)OCC | Oxidation | OtherReaction | 84855dd3f46d7f633669ce7b0a2d1343353729d5975dd53fd20abc6eb43ece69 | dc6f43112eef310adb122ebf81e1733b34eff292ed27058fb45445842d61d3da | c1ccc(-c2ccc[nH]2)cc1 | Cl-c1:c:c:c:c(-C(=[O;H0;D1;+0:1])-O-[OH;D1;+0:2]):c:1.[C;D1;H3:3]-[S;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:3]-[S;H0;D4;+0:4](=[O;H0;D1;+0:2])(=[O;H0;D1;+0:1])-[c:5](:[c:6]):[c:7] | 78 | [{"value": 78.0, "product": "CS(=O)(=O)C1=C(C=CC=C1)C1=CC(=CN1)C=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of 5-[2-(methylthio)phenyl]-1H-pyrrole-3-carbaldehyde (100 mg) in ethyl acetate (5 mL) was added 3-chloroperbenzoic acid (318 mg) under ice-cooling. After stirring at room temperature for 3 hr, a saturated sodium thiosulfate aqueous solution was added to the reaction mixture, and the mixture was extracted... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide.Monosulfide | Sulfone | c1ccccc1 | null | c1ccccc1.c1cc[nH]c1 | HCl | C(C)(=O)OCC | null | 3 | CSc1ccccc1-c1cc(C=O)c[nH]1.O=C(OO)c1cccc(Cl)c1>C(C)(=O)OCC>CS(=O)(=O)c1ccccc1-c1cc(C=O)c[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6adc0d538a8c4616b31f39fd01c23ad6 | O=C1CCC(=O)N1I.O=Cc1c[nH]c(-c2ccccc2F)c1>>O=Cc1c[nH]c(-c2ccccc2F)c1I | FC1=C(C=CC=C1)C1=CC(=CN1)C=O.IN1C(CCC1=O)=O.O>>FC1=C(C=CC=C1)C1=C(C(=CN1)C=O)I | O=C1CCC(=O)N1[I:15].[O:1]=[CH:2][c:3]1[cH:4][nH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[F:13])[cH:14]1>>[O:1]=[CH:2][c:3]1[cH:4][nH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[F:13])[c:14]1[I:15] | O=C1CCC(=O)N1I.O=Cc1c[nH]c(-c2ccccc2F)c1 | O=Cc1c[nH]c(-c2ccccc2F)c1I | null | null | CN(C=O)C | Functional Group Interconversion | OtherReaction | 40ba41cd9c6955f8bb4a47b285f327e8347ac41f3539d665e8b27d9300f356ae | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccc(-c2ccc[nH]2)cc1 | O=C1-C-C-C(=O)-N-1-[I;H0;D1;+0:1].[O;D1;H0:2]=[C:3]-[c:4]1:[c:5]:[#7;a:6]:[c:7](-[c:8]):[cH;D2;+0:9]:1>>[I;H0;D1;+0:1]-[c;H0;D3;+0:9]1:[c:4](-[C:3]=[O;D1;H0:2]):[c:5]:[#7;a:6]:[c:7]:1-[c:8] | 14 | [{"value": 14.0, "product": "FC1=C(C=CC=C1)C1=C(C(=CN1)C=O)I", "details": "PERCENTYIELD", "is_desired": false}, {"value": 13.5, "product": "FC1=C(C=CC=C1)C1=C(C(=CN1)C=O)I", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | 5-(2-Fluorophenyl)-1H-pyrrole-3-carbaldehyde (2.0 g) was dissolved in N,N-dimethylformamide (60 mL), N-iodosuccinimide (2.38 g) was added and the mixture was stirred at for 12 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed successively with a saturat... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | C1CCNC1.c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1.c1ccccc1 | HO- | CN(C=O)C | null | 12 | O=C1CCC(=O)N1I.O=Cc1c[nH]c(-c2ccccc2F)c1>CN(C=O)C>O=Cc1c[nH]c(-c2ccccc2F)c1I |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-931f6899ddd74f4089826a0fe33c8300 | Cc1cc(C)c(-c2cc(C=O)c[nH]2)c(C)c1.O=S(=O)(Cl)c1cccnc1>>Cc1cc(C)c(-c2cc(C=O)cn2S(=O)(=O)c2cccnc2)c(C)c1 | N1=CC(=CC=C1)S(=O)(=O)Cl.C1(=C(C(=CC(=C1)C)C)C1=CC(=CN1)C=O)C.[H-].[Na+].C1COCCOCCOCCOCCO1.C(O)([O-])=O.[Na+]>>C1(=C(C(=CC(=C1)C)C)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)C=O)C | [CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6](-[c:7]2[cH:8][c:9]([CH:10]=[O:11])[cH:12][nH:13]2)[c:23]([CH3:24])[cH:25]1.Cl[S:14](=[O:15])(=[O:16])[c:17]1[cH:18][cH:19][cH:20][n:21][cH:22]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6](-[c:7]2[cH:8][c:9]([CH:10]=[O:11])[cH:12][n:13]2[S:14](=[O:15])(=[O:16])[c:17]2[cH:18][cH:19][cH:... | Cc1cc(C)c(-c2cc(C=O)c[nH]2)c(C)c1.O=S(=O)(Cl)c1cccnc1 | Cc1cc(C)c(-c2cc(C=O)cn2S(=O)(=O)c2cccnc2)c(C)c1 | null | null | O1CCCC1 | Acylation | OtherReaction | b114dd962f9bbda43113428940d60131ff59184183aeb807b43d11ac89af2c38 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8].[O;D1;H0:9]=[C:10]-[c:11]1:[c:12]:[nH;D2;+0:13]:[c:14](-[c:15]):[c:16]:1>>[O;D1;H0:9]=[C:10]-[c:11]1:[c:12]:[n;H0;D3;+0:13](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8]):[c:14](-[c:15]):[c:16]:1 | null | [] | null | null | 0.5 | HOUR | To a solution of 5-mesityl-1H-pyrrole-3-carbaldehyde (0.36 g) in tetrahydrofuran (20 mL) was added sodium hydride (60% in oil, 0.14 g) under ice-cooling, and the mixture was stirred at room temperature for 0.5 hr. A solution of 15-crown-5 (0.75 g) in tetrahydrofuran (3 mL) was added and, after stirring for 5 min, pyrid... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1ccccc1.c1cc[nH]c1.c1ccncc1 | HCl | O1CCCC1 | null | 0.5 | Cc1cc(C)c(-c2cc(C=O)c[nH]2)c(C)c1.O=S(=O)(Cl)c1cccnc1>O1CCCC1>Cc1cc(C)c(-c2cc(C=O)cn2S(=O)(=O)c2cccnc2)c(C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1b00ddfebc1d4ef38bca770d3e48da80 | CSc1ccccc1-c1cc(C=O)c[nH]1.O=S(=O)(Cl)c1cccnc1>>CSc1ccccc1-c1cc(C=O)cn1S(=O)(=O)c1cccnc1 | [H-].[Na+].CSC1=C(C=CC=C1)C1=CC(=CN1)C=O.C1COCCOCCOCCOCCO1.N1=CC(=CC=C1)S(=O)(=O)Cl>>CSC1=C(C=CC=C1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)C=O | [CH3:1][S:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1-[c:9]1[cH:10][c:11]([CH:12]=[O:13])[cH:14][nH:15]1.Cl[S:16](=[O:17])(=[O:18])[c:19]1[cH:20][cH:21][cH:22][n:23][cH:24]1>>[CH3:1][S:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1-[c:9]1[cH:10][c:11]([CH:12]=[O:13])[cH:14][n:15]1[S:16](=[O:17])(=[O:18])[c:19]1[cH:20][cH:21][cH:22]... | CSc1ccccc1-c1cc(C=O)c[nH]1.O=S(=O)(Cl)c1cccnc1 | CSc1ccccc1-c1cc(C=O)cn1S(=O)(=O)c1cccnc1 | null | null | O1CCCC1.O | Acylation | OtherReaction | b114dd962f9bbda43113428940d60131ff59184183aeb807b43d11ac89af2c38 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8].[O;D1;H0:9]=[C:10]-[c:11]1:[c:12]:[c:13](-[c:14]):[nH;D2;+0:15]:[c:16]:1>>[O;D1;H0:9]=[C:10]-[c:11]1:[c:12]:[c:13](-[c:14]):[n;H0;D3;+0:15](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8]):[c:16]:1 | 69 | [{"value": 69.0, "product": "CSC1=C(C=CC=C1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.7, "product": "CSC1=C(C=CC=C1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a suspension of sodium hydride (60% in oil, 40 mg) in tetrahydrofuran (3 mL) were added a solution of 5-[2-(methylthio)phenyl]-1H-pyrrole-3-carbaldehyde (150 mg) in tetrahydrofuran (5 mL), 15-crown-5 (182 mg) and pyridin-3-ylsulfonyl chloride (135 mg) under ice-cooling. After stirring at room temperature for 2 hr, w... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1ccccc1.c1cc[nH]c1.c1ccncc1 | HCl | O1CCCC1.O | null | 2 | CSc1ccccc1-c1cc(C=O)c[nH]1.O=S(=O)(Cl)c1cccnc1>O1CCCC1.O>CSc1ccccc1-c1cc(C=O)cn1S(=O)(=O)c1cccnc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8c213effc8bb49d9b931a711b10d1d38 | O=Cc1c[nH]c(-c2ccccc2Br)c1.O=S(=O)(Cl)c1cccnc1>>O=Cc1cc(-c2ccccc2Br)n(S(=O)(=O)c2cccnc2)c1 | C1COCCOCCOCCOCCO1.[H-].[Na+].N1=CC(=CC=C1)S(=O)(=O)Cl.BrC1=C(C=CC=C1)C1=CC(=CN1)C=O>>BrC1=C(C=CC=C1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)C=O | [O:1]=[CH:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[Br:12])[nH:13][cH:23]1.Cl[S:14](=[O:15])(=[O:16])[c:17]1[cH:18][cH:19][cH:20][n:21][cH:22]1>>[O:1]=[CH:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[Br:12])[n:13]([S:14](=[O:15])(=[O:16])[c:17]2[cH:18][cH:19][cH:20][n:21][cH:22]2)[cH:23... | O=Cc1c[nH]c(-c2ccccc2Br)c1.O=S(=O)(Cl)c1cccnc1 | O=Cc1cc(-c2ccccc2Br)n(S(=O)(=O)c2cccnc2)c1 | null | null | null | Acylation | OtherReaction | b114dd962f9bbda43113428940d60131ff59184183aeb807b43d11ac89af2c38 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8].[O;D1;H0:9]=[C:10]-[c:11]1:[c:12]:[nH;D2;+0:13]:[c:14](-[c:15]):[c:16]:1>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8])-[n;H0;D3;+0:13]1:[c:12]:[c:11](-[C:10]=[O;D1;H0:9]):[c:16]:[c:14]:1-[c:15] | 91 | [{"value": 91.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By a similar operation as in Reference Example 154 and using sodium hydride (60% in oil, 91.0 mg), 5-(2-bromophenyl)-1H-pyrrole-3-carbaldehyde (396 mg), 15-crown-5 (418 mg) and pyridin-3-ylsulfonyl chloride (309 mg), the title compound was obtained as a pale-yellow solid (yield 560 mg, 91%).
Conditions: See reaction.no... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HCl | null | null | null | O=Cc1c[nH]c(-c2ccccc2Br)c1.O=S(=O)(Cl)c1cccnc1>>O=Cc1cc(-c2ccccc2Br)n(S(=O)(=O)c2cccnc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e05e16a7e1e848a19ae3a38a314b7bec | CS(=O)(=O)c1ccccc1-c1cc(C=O)c[nH]1.O=S(=O)(Cl)c1cccnc1>>CS(=O)(=O)c1ccccc1-c1cc(C=O)cn1S(=O)(=O)c1cccnc1 | N1=CC(=CC=C1)S(=O)(=O)Cl.[H-].[Na+].CS(=O)(=O)C1=C(C=CC=C1)C1=CC(=CN1)C=O.C1COCCOCCOCCOCCO1>>CS(=O)(=O)C1=C(C=CC=C1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)C=O | [CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1-[c:11]1[cH:12][c:13]([CH:14]=[O:15])[cH:16][nH:17]1.Cl[S:18](=[O:19])(=[O:20])[c:21]1[cH:22][cH:23][cH:24][n:25][cH:26]1>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1-[c:11]1[cH:12][c:13]([CH:14]=[O:15])[cH:16][n:17]1[S:18](=[O:19])(... | CS(=O)(=O)c1ccccc1-c1cc(C=O)c[nH]1.O=S(=O)(Cl)c1cccnc1 | CS(=O)(=O)c1ccccc1-c1cc(C=O)cn1S(=O)(=O)c1cccnc1 | null | null | null | Acylation | OtherReaction | b114dd962f9bbda43113428940d60131ff59184183aeb807b43d11ac89af2c38 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8].[O;D1;H0:9]=[C:10]-[c:11]1:[c:12]:[c:13](-[c:14]):[nH;D2;+0:15]:[c:16]:1>>[O;D1;H0:9]=[C:10]-[c:11]1:[c:12]:[c:13](-[c:14]):[n;H0;D3;+0:15](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8]):[c:16]:1 | null | [] | null | null | null | null | By a similar operation as in Reference Example 154 and using sodium hydride (60% in oil, 40 mg), 5-[2-(methylsulfonyl)phenyl]-1H-pyrrole-3-carbaldehyde (88.9 mg), 15-crown-5 (94.4 mg) and pyridin-3-ylsulfonyl chloride (69.7 mg), the title compound was obtained as a colorless amorphous form (yield 72.0 mg, 52%).
Conditi... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1ccccc1.c1cc[nH]c1.c1ccncc1 | HCl | null | null | null | CS(=O)(=O)c1ccccc1-c1cc(C=O)c[nH]1.O=S(=O)(Cl)c1cccnc1>>CS(=O)(=O)c1ccccc1-c1cc(C=O)cn1S(=O)(=O)c1cccnc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d15aff367b2e4601bef1aa31e2531357 | O=Cc1cc(-c2ccccc2Br)n(S(=O)(=O)c2cccnc2)c1>>N#Cc1ccccc1-c1cc(C=O)cn1S(=O)(=O)c1cccnc1 | O.BrC1=C(C=CC=C1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)C=O.CN(C=O)C>>C(=O)C=1C=C(N(C1)S(=O)(=O)C=1C=NC=CC1)C1=C(C#N)C=CC=C1 | Br[c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1-[c:9]1[cH:10][c:11]([CH:12]=[O:13])[cH:14][n:15]1[S:16](=[O:17])(=[O:18])[c:19]1[cH:20][cH:21][cH:22][n:23][cH:24]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1-[c:9]1[cH:10][c:11]([CH:12]=[O:13])[cH:14][n:15]1[S:16](=[O:17])(=[O:18])[c:19]1[cH:20][cH:21][cH:22][n:23][cH:24]1 | O=Cc1cc(-c2ccccc2Br)n(S(=O)(=O)c2cccnc2)c1 | N#Cc1ccccc1-c1cc(C=O)cn1S(=O)(=O)c1cccnc1 | null | [C-]#N.[Zn+2].[C-]#N.C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | Miscellaneous | OtherReaction | 3ae4da8b7f110de99cf8afc091b6f0c8540050148e425770f8030bce1480042c | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[c:5]:[#7;a:6]):[c:7]>>[#7;a:6]:[c:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[C:8]#[N;D1;H0:9]):[c:2]:[c:3] | 63 | [{"value": 63.0, "product": "C(=O)C=1C=C(N(C1)S(=O)(=O)C=1C=NC=CC1)C1=C(C#N)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of 5-(2-bromophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde (102 mg), zinc cyanide (61.0 mg) and tetrakis(triphenylphosphine)palladium (60.0 mg) in N,N-dimethylformamide (2 mL) was heated (100 W, 4 min 30 sec) using a microwave focused chemical synthesis reactor manufactured by CEM, water was a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccccc1 | c1ccccc1 | c1ccccc1.c1cc[nH]c1.c1ccncc1 | Br- | [C-]#N.[Zn+2].[C-]#N.C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | null | O=Cc1cc(-c2ccccc2Br)n(S(=O)(=O)c2cccnc2)c1>[C-]#N.[Zn+2].[C-]#N.C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1>N#Cc1ccccc1-c1cc(C=O)cn1S(=O)(=O)c1cccnc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-72c07da92e47481193345178d42ea8e4 | O=Cc1c[nH]c(-c2ccccc2F)c1I.O=S(=O)(Cl)c1cccnc1>>O=Cc1cn(S(=O)(=O)c2cccnc2)c(-c2ccccc2F)c1I | N1=CC(=CC=C1)S(=O)(=O)Cl.C1COCCOCCOCCOCCO1.FC1=C(C=CC=C1)C1=C(C(=CN1)C=O)I.[H-].[Na+]>>FC1=C(C=CC=C1)C1=C(C(=CN1S(=O)(=O)C=1C=NC=CC1)C=O)I | [O:1]=[CH:2][c:3]1[cH:4][nH:5][c:15](-[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[F:22])[c:23]1[I:24].Cl[S:6](=[O:7])(=[O:8])[c:9]1[cH:10][cH:11][cH:12][n:13][cH:14]1>>[O:1]=[CH:2][c:3]1[cH:4][n:5]([S:6](=[O:7])(=[O:8])[c:9]2[cH:10][cH:11][cH:12][n:13][cH:14]2)[c:15](-[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[F:22])[c:... | O=Cc1c[nH]c(-c2ccccc2F)c1I.O=S(=O)(Cl)c1cccnc1 | O=Cc1cn(S(=O)(=O)c2cccnc2)c(-c2ccccc2F)c1I | null | null | O1CCCC1.[Cl-].[Na+].O | Acylation | OtherReaction | b114dd962f9bbda43113428940d60131ff59184183aeb807b43d11ac89af2c38 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8].[O;D1;H0:9]=[C:10]-[c:11]1:[c:12]:[c:13](-[c:14]):[nH;D2;+0:15]:[c:16]:1>>[O;D1;H0:9]=[C:10]-[c:11]1:[c:12]:[c:13](-[c:14]):[n;H0;D3;+0:15](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8]):[c:16]:1 | 93.2 | [{"value": 93.0, "product": "FC1=C(C=CC=C1)C1=C(C(=CN1S(=O)(=O)C=1C=NC=CC1)C=O)I", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.2, "product": "FC1=C(C=CC=C1)C1=C(C(=CN1S(=O)(=O)C=1C=NC=CC1)C=O)I", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution (42 mL) of 5-(2-fluorophenyl)-4-iodo-1H-pyrrole-3-carbaldehyde (400 mg) in tetrahydrofuran was added sodium hydride (60% in oil, 102 mg) at room temperature and the mixture was stirred for 30 min. 15-Crown-5 (560 mg) was added dropwise and the mixture was stirred for 30 min. Pyridin-3-ylsulfonyl chloride ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1.c1ccncc1.c1ccccc1 | HCl | O1CCCC1.[Cl-].[Na+].O | null | 0.5 | O=Cc1c[nH]c(-c2ccccc2F)c1I.O=S(=O)(Cl)c1cccnc1>O1CCCC1.[Cl-].[Na+].O>O=Cc1cn(S(=O)(=O)c2cccnc2)c(-c2ccccc2F)c1I |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-494d2c9f157546e684ff11beeda4d33f | O=C1CCC(=O)N1Br.O=Cc1cc(-c2ccccc2F)n(S(=O)(=O)c2cccnc2)c1>>O=Cc1cc(-c2ccccc2F)n(S(=O)(=O)c2cccnc2)c1Br | FC1=C(C=CC=C1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)C=O.BrN1C(CCC1=O)=O.C(O)([O-])=O.[Na+]>>BrC=1N(C(=CC1C=O)C1=C(C=CC=C1)F)S(=O)(=O)C=1C=NC=CC1 | O=C1CCC(=O)N1[Br:24].[O:1]=[CH:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[F:12])[n:13]([S:14](=[O:15])(=[O:16])[c:17]2[cH:18][cH:19][cH:20][n:21][cH:22]2)[cH:23]1>>[O:1]=[CH:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[F:12])[n:13]([S:14](=[O:15])(=[O:16])[c:17]2[cH:18][cH:19][cH:20][n:2... | O=C1CCC(=O)N1Br.O=Cc1cc(-c2ccccc2F)n(S(=O)(=O)c2cccnc2)c1 | O=Cc1cc(-c2ccccc2F)n(S(=O)(=O)c2cccnc2)c1Br | null | null | CN(C=O)C | Functional Group Interconversion | Bromination | d90c51e04980e4fd5c41f2d9df1deefa5e01053fdb0009dabf82d5beacca27ac | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#16:2]-[#7;a:3]1:[c:4]:[c:5]:[c:6](-[C:7]=[O;D1;H0:8]):[cH;D2;+0:9]:1>>[#16:2]-[#7;a:3]1:[c:4]:[c:5]:[c:6](-[C:7]=[O;D1;H0:8]):[c;H0;D3;+0:9]:1-[Br;H0;D1;+0:1] | null | [] | 80 | CELSIUS | 2 | HOUR | 5-(2-Fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde (330 mg) was dissolved in N,N-dimethylformamide (30 mL), N-bromosuccinimide (356 mg) was added and the mixture was stirred at 80° C. for 2 hr. The reaction mixture was allowed to cool, a saturated aqueous sodium hydrogencarbonate solution was added, ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | C1CCNC1.c1cc[nH]c1 | c1c[nH]cc1 | c1c[nH]cc1.c1ccccc1.c1ccncc1 | HO- | CN(C=O)C | 80 | 2 | O=C1CCC(=O)N1Br.O=Cc1cc(-c2ccccc2F)n(S(=O)(=O)c2cccnc2)c1>CN(C=O)C>O=Cc1cc(-c2ccccc2F)n(S(=O)(=O)c2cccnc2)c1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-530781b19afa4583a2a16ed99221b476 | O=Cc1cn(S(=O)(=O)c2cccnc2)c(-c2ccccc2F)c1I>>N#Cc1c(C=O)cn(S(=O)(=O)c2cccnc2)c1-c1ccccc1F | FC1=C(C=CC=C1)C1=C(C(=CN1S(=O)(=O)C=1C=NC=CC1)C=O)I.[Cu]C#N>>FC1=C(C=CC=C1)C=1N(C=C(C1C#N)C=O)S(=O)(=O)C=1C=NC=CC1 | I[c:3]1[c:4]([CH:5]=[O:6])[cH:7][n:8]([S:9](=[O:10])(=[O:11])[c:12]2[cH:13][cH:14][cH:15][n:16][cH:17]2)[c:18]1-[c:19]1[cH:20][cH:21][cH:22][cH:23][c:24]1[F:25]>>[N:1]#[C:2][c:3]1[c:4]([CH:5]=[O:6])[cH:7][n:8]([S:9](=[O:10])(=[O:11])[c:12]2[cH:13][cH:14][cH:15][n:16][cH:17]2)[c:18]1-[c:19]1[cH:20][cH:21][cH:22][cH:23][... | O=Cc1cn(S(=O)(=O)c2cccnc2)c(-c2ccccc2F)c1I | N#Cc1c(C=O)cn(S(=O)(=O)c2cccnc2)c1-c1ccccc1F | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)P([C-]1C=CC=C1)C1=CC=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2] | O1CCOCC1.C(C)(=O)OCC | Miscellaneous | OtherReaction | 4b83f0d144942e4d28094e20e917b3a04058a1e3505d2097405a3d1ffa833b25 | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | I-[c;H0;D3;+0:1]1:[c:2](-[c:3]):[#7;a:4](-[#16:5]):[c:6]:[c:7]:1-[C:8]=[O;D1;H0:9]>>[#16:5]-[#7;a:4]1:[c:6]:[c:7](-[C:8]=[O;D1;H0:9]):[c;H0;D3;+0:1](-[C:10]#[N;D1;H0:11]):[c:2]:1-[c:3] | 100 | [{"value": 100.0, "product": "FC1=C(C=CC=C1)C=1N(C=C(C1C#N)C=O)S(=O)(=O)C=1C=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.8, "product": "FC1=C(C=CC=C1)C=1N(C=C(C1C#N)C=O)S(=O)(=O)C=1C=NC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 5-(2-Fluorophenyl)-4-iodo-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde (489 mg), copper (I) cyanide (480 mg), tris(dibenzylideneacetone)dipalladium (0) (49 mg) and 1,1′-bis(diphenylphosphino)ferrocene (89 mg) were mixed in 1,4-dioxane (20 mL), and the mixture was heated under reflux for 3 hr. The reaction mixture... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1.c1ccncc1.c1ccccc1 | I- | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)P([C-]1C=CC=C1)C1=CC=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2].O1CCOCC1.C(C)(=O)OCC | null | null | O=Cc1cn(S(=O)(=O)c2cccnc2)c(-c2ccccc2F)c1I>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)P([C-]1C=CC=C1)C1=CC=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2].O1CCOCC1.C(C)(=O)OCC>N#Cc1c(C=O)cn(S(=O)(=O)c2cccnc2)c1-c1cc... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e9f38a1d417242f580b090c5ec4ba0d7 | O=Cc1cc(-c2ccccc2F)n(S(=O)(=O)c2cccnc2)c1Br>>N#Cc1c(C=O)cc(-c2ccccc2F)n1S(=O)(=O)c1cccnc1 | BrC=1N(C(=CC1C=O)C1=C(C=CC=C1)F)S(=O)(=O)C=1C=NC=CC1.[Cu]C#N>>FC1=C(C=CC=C1)C1=CC(=C(N1S(=O)(=O)C=1C=NC=CC1)C#N)C=O | Br[c:3]1[c:4]([CH:5]=[O:6])[cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[F:15])[n:16]1[S:17](=[O:18])(=[O:19])[c:20]1[cH:21][cH:22][cH:23][n:24][cH:25]1>>[N:1]#[C:2][c:3]1[c:4]([CH:5]=[O:6])[cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[F:15])[n:16]1[S:17](=[O:18])(=[O:19])[c:20]1[cH:21][cH:22][cH:23][... | O=Cc1cc(-c2ccccc2F)n(S(=O)(=O)c2cccnc2)c1Br | N#Cc1c(C=O)cc(-c2ccccc2F)n1S(=O)(=O)c1cccnc1 | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)P([C-]1C=CC=C1)C1=CC=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2] | O1CCOCC1.C(C)(=O)OCC | Miscellaneous | OtherReaction | 30908bcc3b754321926ea5ce6063b0580dfaa6092079ba4ccbfabdcfb7713644 | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2](-[#16:3]):[c:4]:[c:5]:[c:6]:1-[C:7]=[O;D1;H0:8]>>[#16:3]-[#7;a:2]1:[c:4]:[c:5]:[c:6](-[C:7]=[O;D1;H0:8]):[c;H0;D3;+0:1]:1-[C:9]#[N;D1;H0:10] | 57.2 | [{"value": 57.0, "product": "FC1=C(C=CC=C1)C1=CC(=C(N1S(=O)(=O)C=1C=NC=CC1)C#N)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.2, "product": "FC1=C(C=CC=C1)C1=CC(=C(N1S(=O)(=O)C=1C=NC=CC1)C#N)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Bromo-5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde (340 mg), copper (I) cyanide (400 mg), tris(dibenzylideneacetone)dipalladium (0) (40 mg), 1,1′-bis(diphenylphosphino)ferrocene (70 mg) were mixed in 1,4-dioxane (30 mL), and the mixture was heated under reflux for 24 hr. The reaction mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1c[nH]cc1 | c1c[nH]cc1 | c1c[nH]cc1.c1ccccc1.c1ccncc1 | Br- | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)P([C-]1C=CC=C1)C1=CC=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2].O1CCOCC1.C(C)(=O)OCC | null | null | O=Cc1cc(-c2ccccc2F)n(S(=O)(=O)c2cccnc2)c1Br>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)P([C-]1C=CC=C1)C1=CC=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2].O1CCOCC1.C(C)(=O)OCC>N#Cc1c(C=O)cc(-c2ccccc2F)n1S(=O)(=O)c1... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c2be1ffdfb244784bfa2d5017652f812 | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.N#Cc1ccc(B(O)O)cc1>>CN(Cc1cc(-c2ccc(C#N)cc2)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | C([O-])([O-])=O.[Na+].[Na+].BrC1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C.C(#N)C1=CC=C(C=C1)B(O)O>>C(#N)C1=CC=C(C=C1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C | Br[c:6]1[cH:5][c:4]([CH2:3][N:2]([CH3:1])[C:26](=[O:27])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32])[cH:25][n:15]1[S:16](=[O:17])(=[O:18])[c:19]1[cH:20][cH:21][cH:22][n:23][cH:24]1.OB(O)[c:7]1[cH:8][cH:9][c:10]([C:11]#[N:12])[cH:13][cH:14]1>>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11]#[N:12])[cH... | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.N#Cc1ccc(B(O)O)cc1 | CN(Cc1cc(-c2ccc(C#N)cc2)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | C-C Coupling | Suzuki coupling with boronic acids | b71c1accb23fcf6e808cbf7fdd27a50d721fbf67e253875213e991e29cdecd2f | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:1-[#16:6].O-B(-O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]>>[#16:6]-[#7;a:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11] | 84 | [{"value": 84.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By a similar operation as in Reference Example 79 and using tert-butyl {[5-bromo-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (430 mg), (4-cyanophenyl)boronic acid (176 mg), sodium carbonate (254 mg) and tetrakis(triphenylphosphine)palladium (57.8 mg), the title compound was obtained as a pale-yellow ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | null | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.N#Cc1ccc(B(O)O)cc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1>CN(Cc1cc(-c2ccc(C#N)cc2)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3bf5a65319f744f481f2c9512ba49155 | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.N#Cc1ccc(F)c(B(O)O)c1>>CN(Cc1cc(-c2cc(C#N)ccc2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | C([O-])([O-])=O.[Na+].[Na+].BrC1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C.C(#N)C=1C=CC(=C(C1)B(O)O)F>>C(#N)C=1C=CC(=C(C1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C)F | Br[c:6]1[cH:5][c:4]([CH2:3][N:2]([CH3:1])[C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33])[cH:26][n:16]1[S:17](=[O:18])(=[O:19])[c:20]1[cH:21][cH:22][cH:23][n:24][cH:25]1.OB(O)[c:7]1[cH:8][c:9]([C:10]#[N:11])[cH:12][cH:13][c:14]1[F:15]>>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][c:9]([C:10]#[N:11])[cH:1... | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.N#Cc1ccc(F)c(B(O)O)c1 | CN(Cc1cc(-c2cc(C#N)ccc2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | C-C Coupling | Suzuki coupling with boronic acids | b71c1accb23fcf6e808cbf7fdd27a50d721fbf67e253875213e991e29cdecd2f | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:1-[#16:6].O-B(-O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](-[F;D1;H0:11]):[c:12]>>[#16:6]-[#7;a:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](-[F;D1;H0:11]):[c:12] | 6 | [{"value": 6.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By a similar operation as in Reference Example 79 and using tert-butyl {[5-bromo-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (430 mg), (5-cyano-2-fluorophenyl)boronic acid (198 mg), sodium carbonate (254 mg) and tetrakis(triphenylphosphine)palladium (57.8 mg), the title compound was obtained as a pal... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | null | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.N#Cc1ccc(F)c(B(O)O)c1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1>CN(Cc1cc(-c2cc(C#N)ccc2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d20ad7774afe4de6b24bc5efc464d795 | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.COc1ccc(F)c(B(O)O)c1>>COc1ccc(F)c(-c2cc(CN(C)C(=O)OC(C)(C)C)cn2S(=O)(=O)c2cccnc2)c1 | C(O)([O-])=O.[Na+].BrC1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C.FC1=C(C=C(C=C1)OC)B(O)O.C(O)([O-])=O.[Na+].COCCOC>>FC1=C(C=C(C=C1)OC)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C | Br[c:9]1[cH:10][c:11]([CH2:12][N:13]([CH3:14])[C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[cH:22][n:23]1[S:24](=[O:25])(=[O:26])[c:27]1[cH:28][cH:29][cH:30][n:31][cH:32]1.OB(O)[c:8]1[c:6]([F:7])[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:33]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([F:7])[c:8](-[c:9]2[cH:10][c:11]([CH2... | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.COc1ccc(F)c(B(O)O)c1 | COc1ccc(F)c(-c2cc(CN(C)C(=O)OC(C)(C)C)cn2S(=O)(=O)c2cccnc2)c1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O | C-C Coupling | Suzuki coupling with boronic acids | b71c1accb23fcf6e808cbf7fdd27a50d721fbf67e253875213e991e29cdecd2f | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:1-[#16:6].O-B(-O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](-[F;D1;H0:11]):[c:12]>>[#16:6]-[#7;a:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](-[F;D1;H0:11]):[c:12] | 100 | [{"value": 100.0, "product": "FC1=C(C=C(C=C1)OC)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.7, "product": "FC1=C(C=C(C=C1)OC)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 1 | HOUR | tert-Butyl {[5-bromo-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (431 mg), (2-fluoro-5-methoxyphenyl)boronic acid (256 mg), sodium hydrogencarbonate (253 mg) and tetrakis(triphenylphosphine)palladium (174 mg) were added to a degassed mixture of 1,2-dimethoxyethane (8 mL) and water (2 mL), and the mix... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccccc1 | c1ccccc1.c1cc[nH]c1 | c1ccccc1.c1cc[nH]c1.c1ccncc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O | 90 | 1 | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.COc1ccc(F)c(B(O)O)c1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O>COc1ccc(F)c(-c2cc(CN(C)C(=O)OC(C)(C)C)cn2S(=O)(=O)c2cccnc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a0d18cb447804851b2c8bfd64f7095f8 | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.O=Cc1cccc(B(O)O)c1F>>CN(Cc1cc(-c2cccc(C=O)c2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | C([O-])([O-])=O.[Na+].[Na+].BrC1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C.FC1=C(C=CC=C1C=O)B(O)O>>FC1=C(C=CC=C1C=O)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C | Br[c:6]1[cH:5][c:4]([CH2:3][N:2]([CH3:1])[C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33])[cH:26][n:16]1[S:17](=[O:18])(=[O:19])[c:20]1[cH:21][cH:22][cH:23][n:24][cH:25]1.OB(O)[c:7]1[cH:8][cH:9][cH:10][c:11]([CH:12]=[O:13])[c:14]1[F:15]>>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][c:11]([CH:... | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.O=Cc1cccc(B(O)O)c1F | CN(Cc1cc(-c2cccc(C=O)c2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | C-C Coupling | Suzuki coupling with boronic acids | b71c1accb23fcf6e808cbf7fdd27a50d721fbf67e253875213e991e29cdecd2f | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:1-[#16:6].O-B(-O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](-[F;D1;H0:11]):[c:12]-[C:13]=[O;D1;H0:14]>>[#16:6]-[#7;a:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](-[F;D1;H0:11]):[c:12]-[C:13]=[O;D1;H0:14] | 53 | [{"value": 53.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By a similar operation as in Reference Example 79 and using tert-butyl {[5-bromo-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (430 mg), (2-fluoro-3-formylphenyl)boronic acid (252 mg), sodium carbonate (254 mg) and tetrakis(triphenylphosphine)palladium (173 mg), the title compound was obtained as a pal... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | null | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.O=Cc1cccc(B(O)O)c1F>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1>CN(Cc1cc(-c2cccc(C=O)c2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-060c35ff5859402aa86e806a435bdb7b | CC(=O)c1cccc(B(O)O)c1F.CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C>>CC(=O)c1cccc(-c2cc(CN(C)C(=O)OC(C)(C)C)cn2S(=O)(=O)c2cccnc2)c1F | C([O-])([O-])=O.[Na+].[Na+].BrC1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C.C(C)(=O)C=1C(=C(C=CC1)B(O)O)F>>C(C)(=O)C=1C(=C(C=CC1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C)F | OB(O)[c:8]1[cH:7][cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[c:33]1[F:34].Br[c:9]1[cH:10][c:11]([CH2:12][N:13]([CH3:14])[C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[cH:22][n:23]1[S:24](=[O:25])(=[O:26])[c:27]1[cH:28][cH:29][cH:30][n:31][cH:32]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][c:8](-[c:9]2[cH:10][c... | CC(=O)c1cccc(B(O)O)c1F.CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | CC(=O)c1cccc(-c2cc(CN(C)C(=O)OC(C)(C)C)cn2S(=O)(=O)c2cccnc2)c1F | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | C-C Coupling | Suzuki coupling with boronic acids | b71c1accb23fcf6e808cbf7fdd27a50d721fbf67e253875213e991e29cdecd2f | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:1-[#16:6].O-B(-O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](-[F;D1;H0:11]):[c:12]-[C:13](-[C;D1;H3:14])=[O;D1;H0:15]>>[#16:6]-[#7;a:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](-[F;D1;H0:11]):[c:12]-[C:13](-[C;D1;H3:14])=[O;D1;H0:15] | 91 | [{"value": 91.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By a similar operation as in Reference Example 79 and using tert-butyl {[5-bromo-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (430 mg), (3-acetyl-2-fluorophenyl)boronic acid (273 mg), sodium carbonate (254 mg), and tetrakis(triphenylphosphine)palladium (173 mg), the title compound was obtained as a pa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1cc[nH]c1 | c1ccccc1.c1cc[nH]c1 | c1ccccc1.c1cc[nH]c1.c1ccncc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | null | CC(=O)c1cccc(B(O)O)c1F.CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1>CC(=O)c1cccc(-c2cc(CN(C)C(=O)OC(C)(C)C)cn2S(=O)(=O)c2cccnc2)c1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-680b437d8f544f0eb56e177eab6ab8c1 | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.OB(O)c1cccnc1F>>CN(Cc1cc(-c2cccnc2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | BrC1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C.FC1=NC=CC=C1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>>FC1=NC=CC=C1C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C | Br[c:6]1[cH:5][c:4]([CH2:3][N:2]([CH3:1])[C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[cH:24][n:14]1[S:15](=[O:16])(=[O:17])[c:18]1[cH:19][cH:20][cH:21][n:22][cH:23]1.OB(O)[c:7]1[cH:8][cH:9][cH:10][n:11][c:12]1[F:13]>>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][n:11][c:12]2[F:13])[n:14](... | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.OB(O)c1cccnc1F | CN(Cc1cc(-c2cccnc2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O.COCCOC | C-C Coupling | Suzuki coupling with boronic acids | f9f2895ba733be961e7e7c9e72afbcb3ef214374a6ccd8f4d6cecf7b329fa7ee | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=S(=O)(c1cccnc1)n1cccc1-c1cccnc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:1-[#16:6].O-B(-O)-[c;H0;D3;+0:7]1:[c:8]:[c:9]:[c:10]:[#7;a:11]:[c:12]:1-[F;D1;H0:13]>>[#16:6]-[#7;a:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:7]1:[c:8]:[c:9]:[c:10]:[#7;a:11]:[c:12]:1-[F;D1;H0:13] | 69.5 | [{"value": 69.0, "product": "FC1=NC=CC=C1C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.5, "product": "FC1=NC=CC=C1C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 105 | CELSIUS | 1 | HOUR | A suspension of tert-butyl {[5-bromo-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (430 mg), (2-fluoropyridin-3-yl)boronic acid (221 mg), sodium carbonate (254 mg) and tetrakis(triphenylphosphine)palladium (173 mg) in 1,2-dimethoxyethane (10 mL) and water (5 mL) was stirred at 105° C. for 1 hr. The rea... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccncc1 | c1cc[nH]c1.c1ccncc1 | c1cc[nH]c1.c1ccncc1.c1ccncc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC | 105 | 1 | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.OB(O)c1cccnc1F>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC>CN(Cc1cc(-c2cccnc2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a304819d7a554cbdb209c0d520fc68a3 | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.OB(O)c1ccncc1F>>CN(Cc1cc(-c2ccncc2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | C(O)([O-])=O.[Na+].BrC1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C.O.FC=1C=NC=CC1B(O)O.C(O)([O-])=O.[Na+].COCCOC>>FC=1C=NC=CC1C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C | Br[c:6]1[cH:5][c:4]([CH2:3][N:2]([CH3:1])[C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[cH:24][n:14]1[S:15](=[O:16])(=[O:17])[c:18]1[cH:19][cH:20][cH:21][n:22][cH:23]1.OB(O)[c:7]1[cH:8][cH:9][n:10][cH:11][c:12]1[F:13]>>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][n:10][cH:11][c:12]2[F:13])[n:14](... | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.OB(O)c1ccncc1F | CN(Cc1cc(-c2ccncc2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O | C-C Coupling | Suzuki coupling with boronic acids | f9f2895ba733be961e7e7c9e72afbcb3ef214374a6ccd8f4d6cecf7b329fa7ee | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=S(=O)(c1cccnc1)n1cccc1-c1ccncc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:1-[#16:6].O-B(-O)-[c;H0;D3;+0:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1-[F;D1;H0:13]>>[#16:6]-[#7;a:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1-[F;D1;H0:13] | 27 | [{"value": 27.0, "product": "FC=1C=NC=CC1C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 26.9, "product": "FC=1C=NC=CC1C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 3 | HOUR | tert-Butyl {[5-bromo-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (215 mg), (3-fluoropyridin-4-yl)boronic acid hydrate (120 mg), sodium hydrogencarbonate (126 mg) and tetrakis(triphenylphosphine)palladium (87 mg) were added to a degassed mixture of 1,2-dimethoxyethane (8 mL) and water (2 mL), and the ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccncc1 | c1cc[nH]c1.c1ccncc1 | c1cc[nH]c1.c1ccncc1.c1ccncc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O | 80 | 3 | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.OB(O)c1ccncc1F>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O>CN(Cc1cc(-c2ccncc2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f15aa40daa0541c3a09617b9e1af0c0a | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.OB(O)c1cccnc1Cl>>CN(Cc1cc(-c2cccnc2Cl)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | C(O)([O-])=O.[Na+].BrC1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C.ClC1=NC=CC=C1B(O)O.C(O)([O-])=O.[Na+].COCCOC>>ClC1=NC=CC=C1C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C | Br[c:6]1[cH:5][c:4]([CH2:3][N:2]([CH3:1])[C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[cH:24][n:14]1[S:15](=[O:16])(=[O:17])[c:18]1[cH:19][cH:20][cH:21][n:22][cH:23]1.OB(O)[c:7]1[cH:8][cH:9][cH:10][n:11][c:12]1[Cl:13]>>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][n:11][c:12]2[Cl:13])[n:14... | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.OB(O)c1cccnc1Cl | CN(Cc1cc(-c2cccnc2Cl)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O | C-C Coupling | Suzuki coupling with boronic acids | f9f2895ba733be961e7e7c9e72afbcb3ef214374a6ccd8f4d6cecf7b329fa7ee | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=S(=O)(c1cccnc1)n1cccc1-c1cccnc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:1-[#16:6].O-B(-O)-[c;H0;D3;+0:7]1:[c:8]:[c:9]:[c:10]:[#7;a:11]:[c:12]:1-[Cl;D1;H0:13]>>[#16:6]-[#7;a:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:7]1:[c:8]:[c:9]:[c:10]:[#7;a:11]:[c:12]:1-[Cl;D1;H0:13] | 60.4 | [{"value": 60.0, "product": "ClC1=NC=CC=C1C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.4, "product": "ClC1=NC=CC=C1C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 3 | HOUR | tert-Butyl {[5-bromo-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (431 mg), (2-chloropyridin-3-yl)boronic acid (237 mg), sodium hydrogencarbonate (126 mg) and tetrakis(triphenylphosphine)palladium (87 mg) were added to a degassed mixture of 1,2-dimethoxyethane (8 mL) and water (2 mL), and the mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccncc1 | c1cc[nH]c1.c1ccncc1 | c1cc[nH]c1.c1ccncc1.c1ccncc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O | 100 | 3 | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.OB(O)c1cccnc1Cl>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O>CN(Cc1cc(-c2cccnc2Cl)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aa362333ad1745a49b752d194bf2bcf2 | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.COCCOC.OB(O)c1ccc(Cl)nc1>>CN(Cc1cc(-c2ccc(-c3ccc(Cl)nc3)nc2)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | C(O)([O-])=O.[Na+].BrC1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C.ClC1=CC=C(C=N1)B(O)O.C(O)([O-])=O.[Na+].COCCOC>>ClC1=CC=C(C=N1)C1=NC=C(C=C1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C | Br[c:6]1[cH:5][c:4]([CH2:3][N:2]([CH3:1])[C:31](=[O:32])[O:33][C:34]([CH3:35])([CH3:36])[CH3:37])[cH:30][n:20]1[S:21](=[O:22])(=[O:23])[c:24]1[cH:25][cH:26][cH:27][n:28][cH:29]1.CO[CH2:9][CH2:8]O[CH3:19].OB(O)[c:11]1[cH:12][cH:13][c:14]([Cl:15])[n:16][cH:17]1>>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c... | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.COCCOC.OB(O)c1ccc(Cl)nc1 | CN(Cc1cc(-c2ccc(-c3ccc(Cl)nc3)nc2)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O | Aromatic Heterocycle Formation | OtherReaction | 7f0c716d3404dcb1513bfb9479eacbe19555b76ef0116724523af9eff62bea1b | b1e241b5084d6e28bf03ac261b0549b490e89d026ab46cd01531bc037abf1ffb | O=S(=O)(c1cccnc1)n1cccc1-c1ccc(-c2cccnc2)nc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:1-[#16:6].C-O-[CH2;D2;+0:7]-[CH2;D2;+0:8]-O-[CH3;D1;+0:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[c:12]:[c:13]:[#7;a:14]:[c:15]:1>>[#16:6]-[#7;a:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[c:16]1:[cH;D2;+0:9]:[#7;a:17]:[c:18](-[c;H0;D3;+0:10]2:[c:11]:[c:12]:[c:13]:[#7;a:14]:[c:15]:2):... | 22 | [{"value": 22.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 3 | HOUR | tert-Butyl {[5-bromo-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (431 mg), (6-chloropyridin-3-yl)boronic acid (237 mg), sodium hydrogencarbonate (252 mg) and tetrakis(triphenylphosphine)palladium (87 mg) were added to a degassed mixture of 1,2-dimethoxyethane (8 mL) and water (2 mL), and the mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Ether.Boronic acid | null | c1cc[nH]c1.c1ccncc1 | c1cc[nH]c1.c1ccncc1.c1ccncc1 | c1cc[nH]c1.c1ccncc1.c1ccncc1.c1ccncc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O | 90 | 3 | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.COCCOC.OB(O)c1ccc(Cl)nc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O>CN(Cc1cc(-c2ccc(-c3ccc(Cl)nc3)nc2)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-721d04ecc4af47aabeb31515c2586abd | COc1ccc(S(=O)(=O)n2cc(CN(C)C(=O)OC(C)(C)C)cc2Br)cn1.OB(O)c1cccnc1F>>COc1ccc(S(=O)(=O)n2cc(CN(C)C(=O)OC(C)(C)C)cc2-c2cccnc2F)cn1 | C([O-])([O-])=O.[Na+].[Na+].BrC1=CC(=CN1S(=O)(=O)C=1C=NC(=CC1)OC)CN(C(OC(C)(C)C)=O)C.FC1=NC=CC=C1B(O)O>>FC1=NC=CC=C1C1=CC(=CN1S(=O)(=O)C=1C=NC(=CC1)OC)CN(C(OC(C)(C)C)=O)C | Br[c:24]1[n:10]([S:7]([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[n:33][cH:32]2)(=[O:8])=[O:9])[cH:11][c:12]([CH2:13][N:14]([CH3:15])[C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[cH:23]1.OB(O)[c:25]1[cH:26][cH:27][cH:28][n:29][c:30]1[F:31]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[n:10]2[cH:11][c:... | COc1ccc(S(=O)(=O)n2cc(CN(C)C(=O)OC(C)(C)C)cc2Br)cn1.OB(O)c1cccnc1F | COc1ccc(S(=O)(=O)n2cc(CN(C)C(=O)OC(C)(C)C)cc2-c2cccnc2F)cn1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | C-C Coupling | Suzuki coupling with boronic acids | f9f2895ba733be961e7e7c9e72afbcb3ef214374a6ccd8f4d6cecf7b329fa7ee | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=S(=O)(c1cccnc1)n1cccc1-c1cccnc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:1-[#16:6].O-B(-O)-[c;H0;D3;+0:7]1:[c:8]:[c:9]:[c:10]:[#7;a:11]:[c:12]:1-[F;D1;H0:13]>>[#16:6]-[#7;a:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:7]1:[c:8]:[c:9]:[c:10]:[#7;a:11]:[c:12]:1-[F;D1;H0:13] | 45 | [{"value": 45.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By a similar operation as in Reference Example 79 and using tert-butyl ({5-bromo-1-[(6-methoxypyridin-3-yl)sulfonyl]-1H-pyrrol-3-yl}methyl)methylcarbamate (463 mg), (2-fluoropyridin-3-yl)boronic acid (172 mg), sodium carbonate (260 mg) and tetrakis(triphenylphosphine)palladium (176 mg), the title compound was obtained ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccncc1 | c1cc[nH]c1.c1ccncc1 | c1ccncc1.c1cc[nH]c1.c1ccncc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | null | COc1ccc(S(=O)(=O)n2cc(CN(C)C(=O)OC(C)(C)C)cc2Br)cn1.OB(O)c1cccnc1F>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1>COc1ccc(S(=O)(=O)n2cc(CN(C)C(=O)OC(C)(C)C)cc2-c2cccnc2F)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1fbb10aa96304307b81d061841206f33 | CN(Cc1cc(-c2cccc(C=O)c2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C>>CN(Cc1cc(-c2cccc(CO)c2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | O.[BH4-].[Na+].FC1=C(C=CC=C1C=O)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C.CO>>FC1=C(C=CC=C1CO)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C | [CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][c:11]([CH:12]=[O:13])[c:14]2[F:15])[n:16]([S:17](=[O:18])(=[O:19])[c:20]2[cH:21][cH:22][cH:23][n:24][cH:25]2)[cH:26]1)[C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33]>>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][c:11]([CH2:12][... | CN(Cc1cc(-c2cccc(C=O)c2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | CN(Cc1cc(-c2cccc(CO)c2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | null | null | O1CCCC1 | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 61.1 | [{"value": 61.0, "product": "FC1=C(C=CC=C1CO)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.1, "product": "FC1=C(C=CC=C1CO)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of tert-butyl {[5-(2-fluoro-3-formylphenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (388 mg) in tetrahydrofuran (8 mL) were added under ice-cooling, sodium borohydride (41.3 mg) and methanol (3 mL). After stirring at the same temperature for 30 min, water was added to the reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1cc[nH]c1.c1ccccc1.c1ccncc1 | null | O1CCCC1 | null | 0.5 | CN(Cc1cc(-c2cccc(C=O)c2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C>O1CCCC1>CN(Cc1cc(-c2cccc(CO)c2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-90cce5cb93644aeb961c04a3a39e21dc | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.COc1cccc(B(O)O)c1F>>COc1cccc(-c2cc(CN(C)C(=O)OC(C)(C)C)cn2S(=O)(=O)c2cccnc2)c1F | C(O)([O-])=O.[Na+].BrC1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C.FC1=C(C=CC=C1OC)B(O)O.C(O)([O-])=O.[Na+].COCCOC>>FC1=C(C=CC=C1OC)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C | Br[c:8]1[cH:9][c:10]([CH2:11][N:12]([CH3:13])[C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[cH:21][n:22]1[S:23](=[O:24])(=[O:25])[c:26]1[cH:27][cH:28][cH:29][n:30][cH:31]1.OB(O)[c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[c:32]1[F:33]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][c:10]([CH2:11][N:12... | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.COc1cccc(B(O)O)c1F | COc1cccc(-c2cc(CN(C)C(=O)OC(C)(C)C)cn2S(=O)(=O)c2cccnc2)c1F | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O | C-C Coupling | Suzuki coupling with boronic acids | b71c1accb23fcf6e808cbf7fdd27a50d721fbf67e253875213e991e29cdecd2f | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:1-[#16:6].O-B(-O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](-[F;D1;H0:11]):[c:12]>>[#16:6]-[#7;a:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](-[F;D1;H0:11]):[c:12] | 100 | [{"value": 100.0, "product": "FC1=C(C=CC=C1OC)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.7, "product": "FC1=C(C=CC=C1OC)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 2 | HOUR | tert-Butyl {[5-bromo-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (431 mg), (2-fluoro-3-methoxyphenyl)boronic acid (256 mg), sodium hydrogencarbonate (253 mg) and tetrakis(triphenylphosphine)palladium (88 mg) were added to a mixture of 1,2-dimethoxyethane (8 mL) and water (2 mL), and the mixture was s... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccccc1 | c1ccccc1.c1cc[nH]c1 | c1ccccc1.c1cc[nH]c1.c1ccncc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O | 100 | 2 | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.COc1cccc(B(O)O)c1F>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O>COc1cccc(-c2cc(CN(C)C(=O)OC(C)(C)C)cn2S(=O)(=O)c2cccnc2)c1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a36f3585c76a4e129ae0ad34d09b0399 | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.COc1cccc(F)c1B(O)O>>COc1cccc(F)c1-c1cc(CN(C)C(=O)OC(C)(C)C)cn1S(=O)(=O)c1cccnc1 | C(O)([O-])=O.[Na+].BrC1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C.FC1=C(C(=CC=C1)OC)B(O)O.C(O)([O-])=O.[Na+].COCCOC>>FC1=C(C(=CC=C1)OC)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C | Br[c:10]1[cH:11][c:12]([CH2:13][N:14]([CH3:15])[C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[cH:23][n:24]1[S:25](=[O:26])(=[O:27])[c:28]1[cH:29][cH:30][cH:31][n:32][cH:33]1.OB(O)[c:9]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][c:7]1[F:8]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([F:8])[c:9]1-[c:10]1[cH:11][c:12]... | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.COc1cccc(F)c1B(O)O | COc1cccc(F)c1-c1cc(CN(C)C(=O)OC(C)(C)C)cn1S(=O)(=O)c1cccnc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O | C-C Coupling | Suzuki coupling with boronic acids | b71c1accb23fcf6e808cbf7fdd27a50d721fbf67e253875213e991e29cdecd2f | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:1-[#16:6].O-B(-O)-[c;H0;D3;+0:7](:[c:8](-[#8:9]):[c:10]):[c:11](-[F;D1;H0:12]):[c:13]>>[#16:6]-[#7;a:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:7](:[c:8](-[#8:9]):[c:10]):[c:11](-[F;D1;H0:12]):[c:13] | 21 | [{"value": 21.0, "product": "FC1=C(C(=CC=C1)OC)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 21.0, "product": "FC1=C(C(=CC=C1)OC)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 20 | HOUR | tert-butyl {[5-bromo-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (431 mg), (2-fluoro-6-methoxyphenyl)boronic acid (256 mg), sodium hydrogencarbonate (253 mg) and tetrakis(triphenylphosphine)palladium (176 mg) were added to a mixture of 1,2-dimethoxyethane (8 mL) and water (2 mL), and the mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccccc1 | c1ccccc1.c1cc[nH]c1 | c1ccccc1.c1cc[nH]c1.c1ccncc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O | 100 | 20 | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.COc1cccc(F)c1B(O)O>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O>COc1cccc(F)c1-c1cc(CN(C)C(=O)OC(C)(C)C)cn1S(=O)(=O)c1cccnc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-827acfb8ff0d4c77bcb847dfdcd60f74 | CC1(C)OB(c2ccc(OC(F)F)cc2)OC1(C)C.CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C>>CN(Cc1cc(-c2ccc(OC(F)F)cc2)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | BrC1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C.C([O-])([O-])=O.[Na+].[Na+].FC(OC1=CC=C(C=C1)B1OC(C(O1)(C)C)(C)C)F>>FC(OC1=CC=C(C=C1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C)F | CC1(C)OB([c:7]2[cH:8][cH:9][c:10]([O:11][CH:12]([F:13])[F:14])[cH:15][cH:16]2)OC1(C)C.Br[c:6]1[cH:5][c:4]([CH2:3][N:2]([CH3:1])[C:28](=[O:29])[O:30][C:31]([CH3:32])([CH3:33])[CH3:34])[cH:27][n:17]1[S:18](=[O:19])(=[O:20])[c:21]1[cH:22][cH:23][cH:24][n:25][cH:26]1>>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:... | CC1(C)OB(c2ccc(OC(F)F)cc2)OC1(C)C.CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | CN(Cc1cc(-c2ccc(OC(F)F)cc2)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O.C(OC)COC | C-C Coupling | Suzuki coupling with boronic esters | d881c94f6706aff038a18340f5cfc1595fb272241e523b8d9697762ef26623fc | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:1-[#16:6].C-C1(-C)-O-B(-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11])-O-C-1(-C)-C>>[#16:6]-[#7;a:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11] | 111.5 | [{"value": 111.5, "product": "FC(OC1=CC=C(C=C1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | tert-Butyl {[5-bromo-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (430 mg), 2-[4-(difluoromethoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (348 mg), sodium carbonate (254 mg) and tetrakis(triphenylphosphine)palladium (174 mg) were suspended in dimethoxyethane (10 mL) and water (4 mL), and the m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | B1OCCO1.c1ccccc1.c1cc[nH]c1 | c1cc[nH]c1.c1ccccc1 | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.C(OC)COC | null | null | CC1(C)OB(c2ccc(OC(F)F)cc2)OC1(C)C.CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.C(OC)COC>CN(Cc1cc(-c2ccc(OC(F)F)cc2)n(S(=O)(=O)c2cccnc2)c1)C(=O... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-18ea53f10e90468db2d2e8f32760e04c | COC(=O)c1ccc(C)nc1.N>>Cc1ccc(C(N)=O)cn1 | CC1=NC=C(C(=O)OC)C=C1.N>>CC1=NC=C(C(=O)N)C=C1 | CO[C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[n:10][cH:9]1)=[O:8].[NH3:7]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]([NH2:7])=[O:8])[cH:9][n:10]1 | COC(=O)c1ccc(C)nc1.N | Cc1ccc(C(N)=O)cn1 | null | null | null | Acylation | OtherReaction | d5b10d4f469e7a196a3b04a6a9e159a7d90514b6df5b50c1197d4b1b774c04e1 | adc0ef6f6c1340dd2dbab737c85bf17fc842769181c5db1a2b4f82b391b28f9f | c1ccncc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].[NH3;D0;+0:8]>>[NH2;D1;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | 72 | [{"value": 72.0, "product": "CC1=NC=C(C(=O)N)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A mixture of methyl 6-methylnicotinate (13.9 g) and 28% aqueous ammonia (140 mL) was stirred at room temperature for 4 hr. The reaction mixture was concentrated under reduced pressure, and the residue was recrystallized from ethanol to give the title compound as a white solid (yield 8.98 g, 72%).
Conditions: See reacti... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary amide | null | null | c1ccncc1 | HO- | null | null | 4 | COC(=O)c1ccc(C)nc1.N>>Cc1ccc(C(N)=O)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-41d4ea4a7fe4421e8ab45eec520f6a0e | Cc1ccc(N)cn1.Cl>>Cc1ccc(S(=O)(=O)Cl)cn1 | Cl.S(=O)(O)[O-].[Na+].N(=O)[O-].[Na+].CC1=CC=C(C=N1)N.Cl>>CC1=CC=C(C=N1)S(=O)(=O)Cl | N[c:5]1[cH:4][cH:3][c:2]([CH3:1])[n:11][cH:10]1.[ClH:9]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[Cl:9])[cH:10][n:11]1 | Cc1ccc(N)cn1.Cl | Cc1ccc(S(=O)(=O)Cl)cn1 | null | S(=O)(=O)([O-])[O-].[Cu+2] | O | Oxidation | OtherReaction | ecf1acd34cb4a0cd4ff4e0d9c6183b72a52f8d3b7fe15a03cdfa932b4ff35d44 | 1d4cad94c21636bff4e568099df1dbf6182f0b939dba308ba7cb5f2ccc1f5a72 | c1ccncc1 | N-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.[ClH;D0;+0:7]>>[Cl;H0;D1;+0:7]-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1 | 15 | [{"value": 15.0, "product": "CC1=CC=C(C=N1)S(=O)(=O)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a mixture of 6-methylpyridine-3-amine (449 mg) and concentrated hydrochloric acid (5 mL) was added a solution of sodium nitrite (857 mg) in water (2 mL) at 0° C., and the mixture was stirred at the same temperature for 10 min. To the mixture was added a solution of concentrated hydrochloric acid (2.5 mL), copper sul... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Sulfonyl halide | c1ccncc1 | c1ccncc1 | c1ccncc1 | null | S(=O)(=O)([O-])[O-].[Cu+2].O | null | 0.166667 | Cc1ccc(N)cn1.Cl>S(=O)(=O)([O-])[O-].[Cu+2].O>Cc1ccc(S(=O)(=O)Cl)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-680d114cfcdd4ec49d65a822b993eb19 | CN(Cc1c[nH]c(Br)c1)C(=O)OC(C)(C)C.Cc1ccc(S(=O)(=O)Cl)cn1>>Cc1ccc(S(=O)(=O)n2cc(CN(C)C(=O)OC(C)(C)C)cc2Br)cn1 | C1COCCOCCOCCOCCO1.CC1=CC=C(C=N1)S(=O)(=O)Cl.BrC1=CC(=CN1)CN(C(OC(C)(C)C)=O)C.[H-].[Na+]>>BrC1=CC(=CN1S(=O)(=O)C=1C=NC(=CC1)C)CN(C(OC(C)(C)C)=O)C | [nH:9]1[cH:10][c:11]([CH2:12][N:13]([CH3:14])[C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[cH:22][c:23]1[Br:24].Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[n:26][cH:25]1)(=[O:7])=[O:8]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[n:9]2[cH:10][c:11]([CH2:12][N:13]([CH3:14])[C:15](=[O:16])[O:17][C:18]([C... | CN(Cc1c[nH]c(Br)c1)C(=O)OC(C)(C)C.Cc1ccc(S(=O)(=O)Cl)cn1 | Cc1ccc(S(=O)(=O)n2cc(CN(C)C(=O)OC(C)(C)C)cc2Br)cn1 | null | null | O1CCCC1.O | Acylation | OtherReaction | b114dd962f9bbda43113428940d60131ff59184183aeb807b43d11ac89af2c38 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1cccnc1)n1cccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8].[Br;D1;H0:9]-[c:10]1:[c:11]:[c:12]:[c:13]:[nH;D2;+0:14]:1>>[Br;D1;H0:9]-[c:10]1:[c:11]:[c:12]:[c:13]:[n;H0;D3;+0:14]:1-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8] | 79 | [{"value": 79.0, "product": "BrC1=CC(=CN1S(=O)(=O)C=1C=NC(=CC1)C)CN(C(OC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.5, "product": "BrC1=CC(=CN1S(=O)(=O)C=1C=NC(=CC1)C)CN(C(OC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of tert-butyl [(5-bromo-1H-pyrrol-3-yl)methyl]methylcarbamate (207 mg) in tetrahydrofuran (30 mL) was added sodium hydride (60% in oil, 31 mg) at 0° C., and the mixture was stirred at the same temperature for 10 min. A solution (3 mL) of 15-crown-5 (0.16 mL) and 6-methylpyridin-3-ylsulfonyl chloride (117 ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1ccncc1.c1cc[nH]c1 | HCl | O1CCCC1.O | null | 0.166667 | CN(Cc1c[nH]c(Br)c1)C(=O)OC(C)(C)C.Cc1ccc(S(=O)(=O)Cl)cn1>O1CCCC1.O>Cc1ccc(S(=O)(=O)n2cc(CN(C)C(=O)OC(C)(C)C)cc2Br)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-388329946d964227bbcad966b23e8a51 | Cc1ccc(S(=O)(=O)n2cc(CN(C)C(=O)OC(C)(C)C)cc2Br)cn1.OB(O)c1cccnc1F>>Cc1ccc(S(=O)(=O)n2cc(CN(C)C(=O)OC(C)(C)C)cc2-c2cccnc2F)cn1 | BrC1=CC(=CN1S(=O)(=O)C=1C=NC(=CC1)C)CN(C(OC(C)(C)C)=O)C.FC1=NC=CC=C1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>>FC1=NC=CC=C1C1=CC(=CN1S(=O)(=O)C=1C=NC(=CC1)C)CN(C(OC(C)(C)C)=O)C | Br[c:23]1[n:9]([S:6]([c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:32][cH:31]2)(=[O:7])=[O:8])[cH:10][c:11]([CH2:12][N:13]([CH3:14])[C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[cH:22]1.OB(O)[c:24]1[cH:25][cH:26][cH:27][n:28][c:29]1[F:30]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[n:9]2[cH:10][c:11]([CH2:12]... | Cc1ccc(S(=O)(=O)n2cc(CN(C)C(=O)OC(C)(C)C)cc2Br)cn1.OB(O)c1cccnc1F | Cc1ccc(S(=O)(=O)n2cc(CN(C)C(=O)OC(C)(C)C)cc2-c2cccnc2F)cn1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O.COCCOC | C-C Coupling | Suzuki coupling with boronic acids | f9f2895ba733be961e7e7c9e72afbcb3ef214374a6ccd8f4d6cecf7b329fa7ee | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=S(=O)(c1cccnc1)n1cccc1-c1cccnc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:1-[#16:6].O-B(-O)-[c;H0;D3;+0:7]1:[c:8]:[c:9]:[c:10]:[#7;a:11]:[c:12]:1-[F;D1;H0:13]>>[#16:6]-[#7;a:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:7]1:[c:8]:[c:9]:[c:10]:[#7;a:11]:[c:12]:1-[F;D1;H0:13] | 41 | [{"value": 41.0, "product": "FC1=NC=CC=C1C1=CC(=CN1S(=O)(=O)C=1C=NC(=CC1)C)CN(C(OC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.7, "product": "FC1=NC=CC=C1C1=CC(=CN1S(=O)(=O)C=1C=NC(=CC1)C)CN(C(OC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 105 | CELSIUS | 1 | HOUR | A suspension of tert-butyl ({5-bromo-1-[(6-methylpyridin-3-yl)sulfonyl]-1H-pyrrol-3-yl}methyl)methylcarbamate (206 mg), (2-fluoropyridin-3-yl)boronic acid (80 mg), sodium carbonate (119 mg) and tetrakis(triphenylphosphine)palladium (80 mg) in 1,2-dimethoxyethane (5 mL) and water (2.5 mL) was stirred under a nitrogen at... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccncc1 | c1cc[nH]c1.c1ccncc1 | c1ccncc1.c1cc[nH]c1.c1ccncc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC | 105 | 1 | Cc1ccc(S(=O)(=O)n2cc(CN(C)C(=O)OC(C)(C)C)cc2Br)cn1.OB(O)c1cccnc1F>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC>Cc1ccc(S(=O)(=O)n2cc(CN(C)C(=O)OC(C)(C)C)cc2-c2cccnc2F)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9f9df08ce22a4171b96b3e410f9b31fb | O=Cc1cc(Br)n(S(=O)(=O)c2ccccc2)c1.OB(O)c1cccnc1F>>O=Cc1cc(-c2cccnc2F)n(S(=O)(=O)c2ccccc2)c1 | C(O)([O-])=O.[Na+].BrC1=CC(=CN1S(=O)(=O)C1=CC=CC=C1)C=O.FC1=NC=CC=C1B(O)O.C(O)([O-])=O.[Na+].COCCOC>>FC1=NC=CC=C1C1=CC(=CN1S(=O)(=O)C1=CC=CC=C1)C=O | Br[c:5]1[cH:4][c:3]([CH:2]=[O:1])[cH:23][n:13]1[S:14](=[O:15])(=[O:16])[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.OB(O)[c:6]1[cH:7][cH:8][cH:9][n:10][c:11]1[F:12]>>[O:1]=[CH:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][n:10][c:11]2[F:12])[n:13]([S:14](=[O:15])(=[O:16])[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[cH:2... | O=Cc1cc(Br)n(S(=O)(=O)c2ccccc2)c1.OB(O)c1cccnc1F | O=Cc1cc(-c2cccnc2F)n(S(=O)(=O)c2ccccc2)c1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O | C-C Coupling | Suzuki coupling with boronic acids | f9f2895ba733be961e7e7c9e72afbcb3ef214374a6ccd8f4d6cecf7b329fa7ee | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=S(=O)(c1ccccc1)n1cccc1-c1cccnc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[C:4]=[O;D1;H0:5]):[c:6]:[#7;a:7]:1-[#16:8].O-B(-O)-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[c:12]:[#7;a:13]:[c:14]:1-[F;D1;H0:15]>>[#16:8]-[#7;a:7]1:[c:6]:[c:3](-[C:4]=[O;D1;H0:5]):[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[c:12]:[#7;a:13]:[c:14]:1-[F;D1;H0:15] | 68 | [{"value": 68.0, "product": "FC1=NC=CC=C1C1=CC(=CN1S(=O)(=O)C1=CC=CC=C1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.9, "product": "FC1=NC=CC=C1C1=CC(=CN1S(=O)(=O)C1=CC=CC=C1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 5 | HOUR | 5-Bromo-1-(phenylsulfonyl)-1H-pyrrole-3-carbaldehyde (3.15 g), (2-fluoropyridin-3-yl)boronic acid (2.83 g), sodium hydrogencarbonate (2.53 g) and tetrakis(triphenylphosphine)palladium (870 mg) were added to a degassed mixture of 1,2-dimethoxyethane (80 mL) and water (20 mL), and the mixture was stirred under a nitrogen... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccncc1 | c1cc[nH]c1.c1ccncc1 | c1cc[nH]c1.c1ccncc1.c1ccccc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O | 80 | 5 | O=Cc1cc(Br)n(S(=O)(=O)c2ccccc2)c1.OB(O)c1cccnc1F>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O>O=Cc1cc(-c2cccnc2F)n(S(=O)(=O)c2ccccc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3ec90486c2354644810e077b509e47b2 | O=Cc1cc(-c2cccnc2F)n(S(=O)(=O)c2ccccc2)c1>>O=Cc1c[nH]c(-c2cccnc2F)c1 | [OH-].[Na+].FC1=NC=CC=C1C1=CC(=CN1S(=O)(=O)C1=CC=CC=C1)C=O>>FC1=NC=CC=C1C1=CC(=CN1)C=O | O=S(=O)(c1ccccc1)[n:5]1[cH:4][c:3]([CH:2]=[O:1])[cH:14][c:6]1-[c:7]1[cH:8][cH:9][cH:10][n:11][c:12]1[F:13]>>[O:1]=[CH:2][c:3]1[cH:4][nH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][n:11][c:12]2[F:13])[cH:14]1 | O=Cc1cc(-c2cccnc2F)n(S(=O)(=O)c2ccccc2)c1 | O=Cc1c[nH]c(-c2cccnc2F)c1 | null | null | O1CCCC1.[Cl-].[Na+].O.CO | Reduction | OtherReaction | e84bce0a3684cb001278a9df3f54235c2ecd212d7bfeaa59bdd53379604bae1d | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1cncc(-c2ccc[nH]2)c1 | O=S(=O)(-[n;H0;D3;+0:1]1:[c:2]:[c:3](-[C:4]=[O;D1;H0:5]):[c:6]:[c:7]:1-[c:8]:[c:9]:[#7;a:10])-c1:c:c:c:c:c:1>>[#7;a:10]:[c:9]:[c:8]-[c:7]1:[c:6]:[c:3](-[C:4]=[O;D1;H0:5]):[c:2]:[nH;D2;+0:1]:1 | 79.5 | [{"value": 79.0, "product": "FC1=NC=CC=C1C1=CC(=CN1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.5, "product": "FC1=NC=CC=C1C1=CC(=CN1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 5-(2-Fluoropyridin-3-yl)-1-(phenylsulfonyl)-1H-pyrrole-3-carbaldehyde (2.25 g) was dissolved in methanol (20 mL) and tetrahydrofuran (20 mL), a 8 mol/L aqueous sodium hydroxide solution (20 mL) was added dropwise at room temperature and the mixture was stirred for 1 hr. The reaction mixture was diluted with saturated b... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1.c1ccncc1 | HO- | O1CCCC1.[Cl-].[Na+].O.CO | null | 1 | O=Cc1cc(-c2cccnc2F)n(S(=O)(=O)c2ccccc2)c1>O1CCCC1.[Cl-].[Na+].O.CO>O=Cc1c[nH]c(-c2cccnc2F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f3dfb5d580d3496e9876488b1377cca3 | O=C1CCC(=O)N1Cl.O=Cc1c[nH]c(-c2cccnc2F)c1>>O=Cc1c[nH]c(-c2cccnc2F)c1Cl | FC1=NC=CC=C1C1=CC(=CN1)C=O.ClN1C(CCC1=O)=O.O>>ClC=1C(=CNC1C=1C(=NC=CC1)F)C=O | O=C1CCC(=O)N1[Cl:15].[O:1]=[CH:2][c:3]1[cH:4][nH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][n:11][c:12]2[F:13])[cH:14]1>>[O:1]=[CH:2][c:3]1[cH:4][nH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][n:11][c:12]2[F:13])[c:14]1[Cl:15] | O=C1CCC(=O)N1Cl.O=Cc1c[nH]c(-c2cccnc2F)c1 | O=Cc1c[nH]c(-c2cccnc2F)c1Cl | null | null | CN(C=O)C | Functional Group Interconversion | Chlorination | 40ba41cd9c6955f8bb4a47b285f327e8347ac41f3539d665e8b27d9300f356ae | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1cncc(-c2ccc[nH]2)c1 | O=C1-C-C-C(=O)-N-1-[Cl;H0;D1;+0:1].[#7;a:2]:[c:3]:[c:4]-[c:5]1:[#7;a:6]:[c:7]:[c:8](-[C:9]=[O;D1;H0:10]):[cH;D2;+0:11]:1>>[#7;a:2]:[c:3]:[c:4]-[c:5]1:[#7;a:6]:[c:7]:[c:8](-[C:9]=[O;D1;H0:10]):[c;H0;D3;+0:11]:1-[Cl;H0;D1;+0:1] | 44.4 | [{"value": 44.0, "product": "ClC=1C(=CNC1C=1C(=NC=CC1)F)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.4, "product": "ClC=1C(=CNC1C=1C(=NC=CC1)F)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 40 | MINUTE | 5-(2-Fluoropyridin-3-yl)-1H-pyrrole-3-carbaldehyde (610 mg) was dissolved in N,N-dimethylformamide (20 mL), N-chlorosuccinimide (641 mg) was added and the mixture was stirred at 80° C. for 40 min. After cooling, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was w... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | C1CCNC1.c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1.c1ccncc1 | HO- | CN(C=O)C | 80 | 0.666667 | O=C1CCC(=O)N1Cl.O=Cc1c[nH]c(-c2cccnc2F)c1>CN(C=O)C>O=Cc1c[nH]c(-c2cccnc2F)c1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-411af986b68c4915bbedc178280717e7 | O=Cc1c[nH]c(-c2cccnc2F)c1Cl.O=S(=O)(Cl)c1cccnc1>>O=Cc1cn(S(=O)(=O)c2cccnc2)c(-c2cccnc2F)c1Cl | N1=CC(=CC=C1)S(=O)(=O)Cl.C1COCCOCCOCCOCCO1.ClC=1C(=CNC1C=1C(=NC=CC1)F)C=O.[H-].[Na+]>>ClC=1C(=CN(C1C=1C(=NC=CC1)F)S(=O)(=O)C=1C=NC=CC1)C=O | [O:1]=[CH:2][c:3]1[cH:4][nH:5][c:15](-[c:16]2[cH:17][cH:18][cH:19][n:20][c:21]2[F:22])[c:23]1[Cl:24].Cl[S:6](=[O:7])(=[O:8])[c:9]1[cH:10][cH:11][cH:12][n:13][cH:14]1>>[O:1]=[CH:2][c:3]1[cH:4][n:5]([S:6](=[O:7])(=[O:8])[c:9]2[cH:10][cH:11][cH:12][n:13][cH:14]2)[c:15](-[c:16]2[cH:17][cH:18][cH:19][n:20][c:21]2[F:22])[c:2... | O=Cc1c[nH]c(-c2cccnc2F)c1Cl.O=S(=O)(Cl)c1cccnc1 | O=Cc1cn(S(=O)(=O)c2cccnc2)c(-c2cccnc2F)c1Cl | null | null | O1CCCC1.[Cl-].[Na+].O | Acylation | OtherReaction | b114dd962f9bbda43113428940d60131ff59184183aeb807b43d11ac89af2c38 | 97f7469015d28c17dd04331dd6d96add6c8052624259a8aad52811d647e364c7 | O=S(=O)(c1cccnc1)n1cccc1-c1cccnc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8].[#7;a:9]:[c:10]:[c:11]-[c:12]1:[c:13]:[c:14](-[C:15]=[O;D1;H0:16]):[c:17]:[nH;D2;+0:18]:1>>[#7;a:9]:[c:10]:[c:11]-[c:12]1:[c:13]:[c:14](-[C:15]=[O;D1;H0:16]):[c:17]:[n;H0;D3;+0:18]:1-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5])... | 81.4 | [{"value": 81.0, "product": "ClC=1C(=CN(C1C=1C(=NC=CC1)F)S(=O)(=O)C=1C=NC=CC1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.4, "product": "ClC=1C(=CN(C1C=1C(=NC=CC1)F)S(=O)(=O)C=1C=NC=CC1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution (20 mL) of 4-chloro-5-(2-fluoropyridin-3-yl)-1H-pyrrole-3-carbaldehyde (270 mg) in tetrahydrofuran was added sodium hydride (60% in oil, 100 mg) at room temperature and the mixture was stirred for 30 min. 15-Crown-5 (530 mg) was added dropwise and the mixture was stirred for 30 min. 3-Pyridylsulfonyl chlo... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1cc[nH]c1.c1ccncc1.c1ccncc1 | HCl | O1CCCC1.[Cl-].[Na+].O | null | 0.5 | O=Cc1c[nH]c(-c2cccnc2F)c1Cl.O=S(=O)(Cl)c1cccnc1>O1CCCC1.[Cl-].[Na+].O>O=Cc1cn(S(=O)(=O)c2cccnc2)c(-c2cccnc2F)c1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e9ef8d9357e749f19747a0c93c25e16c | Brc1cccs1.CCC[CH2][Sn]([Cl])([CH2]CCC)[CH2]CCC>>CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cccs1 | C(CCC)[Sn](CCCC)(CCCC)Cl.C(CCC)[Li].BrC=1SC=CC1.O>>C(CCC)[Sn](C=1SC=CC1)(CCCC)CCCC | Br[c:14]1[cH:15][cH:16][cH:17][s:18]1.[Cl][Sn:5]([CH2:4][CH2:3][CH2:2][CH3:1])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:10][CH2:11][CH2:12][CH3:13]>>[CH3:1][CH2:2][CH2:3][CH2:4][Sn:5]([CH2:6][CH2:7][CH2:8][CH3:9])([CH2:10][CH2:11][CH2:12][CH3:13])[c:14]1[cH:15][cH:16][cH:17][s:18]1 | Brc1cccs1.CCC[CH2][Sn]([Cl])([CH2]CCC)[CH2]CCC | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cccs1 | null | null | O1CCCC1.CCCCCC | Functional Group Interconversion | OtherReaction | e363417aa5b20edf9c75e86f016b75ab78ca0c0aabdcfb807eb5acd778537bff | d9bf9bd3fc00efb5d713d9ac7f168986c2c94f1f455d32bdc9901567c1014c76 | c1ccsc1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1.[C:6]-[C:7]-[Sn;H0;D4;+0:8](-[Cl])(-[C:9]-[C:10])-[C:11]-[C:12]>>[C:6]-[C:7]-[Sn;H0;D4;+0:8](-[C:9]-[C:10])(-[C:11]-[C:12])-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1 | null | [] | null | null | 30 | MINUTE | A solution (10 mL) of 2-bromothiophene (1.0 g) in tetrahydrofuran was cooled to −70° C., and a 1.6 mol/L solution (4.2 mL) of n-butyllithium in hexane was added dropwise. After stirring at the same temperature for 30 min, tributyltin chloride (2.1 g) was added dropwise. After further stirring for 1 hr, water was added ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | Tin | c1ccsc1 | c1ccsc1 | c1ccsc1 | Br- | O1CCCC1.CCCCCC | null | 0.5 | Brc1cccs1.CCC[CH2][Sn]([Cl])([CH2]CCC)[CH2]CCC>O1CCCC1.CCCCCC>CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cccs1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6e02e46e866c46c99e8a35736d9466fa | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cccs1.CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C>>CN(Cc1cc(-c2cccs2)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | C(CCC)[Sn](C=1SC=CC1)(CCCC)CCCC.BrC1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C>>CN(C(OC(C)(C)C)=O)CC1=CN(C(=C1)C=1SC=CC1)S(=O)(=O)C=1C=NC=CC1 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:7]1[cH:8][cH:9][cH:10][s:11]1.Br[c:6]1[cH:5][c:4]([CH2:3][N:2]([CH3:1])[C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[cH:22][n:12]1[S:13](=[O:14])(=[O:15])[c:16]1[cH:17][cH:18][cH:19][n:20][cH:21]1>>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][s:11]2)[n:1... | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cccs1.CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | CN(Cc1cc(-c2cccs2)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C1(=CC=CC=C1)C | C-C Coupling | Stille reaction_aryl | 0633e4f5a640a10123223b534128162781440d4e4fc895bc244198018a95099f | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | O=S(=O)(c1cccnc1)n1cccc1-c1cccs1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:1-[#16:6].C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:7]1:[#16;a:8]:[c:9]:[c:10]:[c:11]:1>>[#16:6]-[#7;a:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:7]1:[#16;a:8]:[c:9]:[c:10]:[c:11]:1 | 73 | [{"value": 73.0, "product": "CN(C(OC(C)(C)C)=O)CC1=CN(C(=C1)C=1SC=CC1)S(=O)(=O)C=1C=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.7, "product": "CN(C(OC(C)(C)C)=O)CC1=CN(C(=C1)C=1SC=CC1)S(=O)(=O)C=1C=NC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 1 | HOUR | To a solution of crude tributyl(2-thienyl)stannane (1.1 g) and tert-butyl {[5-bromo-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (430 mg) in toluene was added tetrakis(triphenylphosphine)palladium (116 mg), and the mixture was stirred under a nitrogen atmosphere at 120° C. for 1 hr. The reaction mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1ccsc1.c1cc[nH]c1 | c1cc[nH]c1.c1ccsc1 | c1cc[nH]c1.c1ccsc1.c1ccncc1 | HBr.Sn | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C | 120 | 1 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cccs1.CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C>CN(Cc1cc(-c2cccs2)n(S(=O)(=O)c2cccnc2)c1)C... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3c913c3f3cb8466ca9305ca3d7fc9612 | CCC[CH2][Sn]([Cl])([CH2]CCC)[CH2]CCC.Cc1cccnc1Br>>CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ncccc1C | C(CCC)[Sn](CCCC)(CCCC)Cl.C(CCC)[Li].BrC1=NC=CC=C1C.O>>CC=1C(=NC=CC1)[Sn](CCCC)(CCCC)CCCC | [Cl][Sn:5]([CH2:4][CH2:3][CH2:2][CH3:1])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:10][CH2:11][CH2:12][CH3:13].Br[c:14]1[n:15][cH:16][cH:17][cH:18][c:19]1[CH3:20]>>[CH3:1][CH2:2][CH2:3][CH2:4][Sn:5]([CH2:6][CH2:7][CH2:8][CH3:9])([CH2:10][CH2:11][CH2:12][CH3:13])[c:14]1[n:15][cH:16][cH:17][cH:18][c:19]1[CH3:20] | CCC[CH2][Sn]([Cl])([CH2]CCC)[CH2]CCC.Cc1cccnc1Br | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ncccc1C | null | null | O1CCCC1.CCCCCC | Functional Group Interconversion | OtherReaction | 595ac0abb5e92435d058c6ee48fc895ec9c292bdbe417f57a54b9f065eff0354 | d9bf9bd3fc00efb5d713d9ac7f168986c2c94f1f455d32bdc9901567c1014c76 | c1ccncc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6].[C:7]-[C:8]-[Sn;H0;D4;+0:9](-[Cl])(-[C:10]-[C:11])-[C:12]-[C:13]>>[C:7]-[C:8]-[Sn;H0;D4;+0:9](-[C:10]-[C:11])(-[C:12]-[C:13])-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6] | 79 | [{"value": 79.0, "product": "CC=1C(=NC=CC1)[Sn](CCCC)(CCCC)CCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.8, "product": "CC=1C(=NC=CC1)[Sn](CCCC)(CCCC)CCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A solution (10 mL) of 2-bromo-3-methylpyridine (1.0 g) in tetrahydrofuran was cooled to −70° C., and a 1.6 mol/L solution (4.0 mL) of n-butyllithium in hexane was added dropwise. After stirring at the same temperature for 15 min, tributyltin chloride (2.2 g) was added dropwise. After further stirring for 1 hr, water wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | Tin | c1ccncc1 | c1ccncc1 | c1ccncc1 | Br- | O1CCCC1.CCCCCC | null | 0.25 | CCC[CH2][Sn]([Cl])([CH2]CCC)[CH2]CCC.Cc1cccnc1Br>O1CCCC1.CCCCCC>CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ncccc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7e097de107c94f40815c9390fe085e9f | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ncccc1C.CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C>>Cc1cccnc1-c1cc(CN(C)C(=O)OC(C)(C)C)cn1S(=O)(=O)c1cccnc1 | CC=1C(=NC=CC1)[Sn](CCCC)(CCCC)CCCC.BrC1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C>>CN(C(OC(C)(C)C)=O)CC1=CN(C(=C1)C1=NC=CC=C1C)S(=O)(=O)C=1C=NC=CC1 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:7]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][n:6]1.Br[c:8]1[cH:9][c:10]([CH2:11][N:12]([CH3:13])[C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[cH:21][n:22]1[S:23](=[O:24])(=[O:25])[c:26]1[cH:27][cH:28][cH:29][n:30][cH:31]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1-[c:8]1[cH:9][c:10... | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ncccc1C.CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | Cc1cccnc1-c1cc(CN(C)C(=O)OC(C)(C)C)cn1S(=O)(=O)c1cccnc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C1(=CC=CC=C1)C | C-C Coupling | Stille reaction_aryl | 2b1ce17c4236d1fc1461a80952491ef35edb4706d7dcf6a032a7dd68392b8501 | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccn1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:1-[#16:6].C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:7](:[#7;a:8]:[c:9]):[c:10](-[C;D1;H3:11]):[c:12]>>[#16:6]-[#7;a:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:7](:[#7;a:8]:[c:9]):[c:10](-[C;D1;H3:11]):[c:12] | 22.3 | [{"value": 22.0, "product": "CN(C(OC(C)(C)C)=O)CC1=CN(C(=C1)C1=NC=CC=C1C)S(=O)(=O)C=1C=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 22.3, "product": "CN(C(OC(C)(C)C)=O)CC1=CN(C(=C1)C1=NC=CC=C1C)S(=O)(=O)C=1C=NC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3-methyl-2-(tributylstannyl)pyridine (1.0 g), tert-butyl {[5-bromo-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (563 mg) and tetrakis(triphenylphosphine)palladium (454 mg) in toluene was stirred under a nitrogen atmosphere at 120° C. for 30 hr. The mixture was cooled to room temperature ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1ccncc1.c1cc[nH]c1 | c1ccncc1.c1cc[nH]c1 | c1ccncc1.c1cc[nH]c1.c1ccncc1 | HBr.Sn | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C | null | null | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ncccc1C.CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C>Cc1cccnc1-c1cc(CN(C)C(=O)OC(C)(C)C)cn1S(... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aebfa6072d1a4614bf68fd306315f268 | CN(Cc1cc(-c2cccc(C=O)c2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.NO>>CN(Cc1cc(-c2cccc(C=NO)c2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | C(O)([O-])=O.[Na+].C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)C1=C(C(=CC=C1)C=O)F)S(=O)(=O)C=1C=NC=CC1)=O.Cl.NO.C(C)(=O)[O-].[Na+]>>FC1=C(C=CC=C1C=NO)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C | O=[CH:12][c:11]1[cH:10][cH:9][cH:8][c:7](-[c:6]2[cH:5][c:4]([CH2:3][N:2]([CH3:1])[C:28](=[O:29])[O:30][C:31]([CH3:32])([CH3:33])[CH3:34])[cH:27][n:17]2[S:18](=[O:19])(=[O:20])[c:21]2[cH:22][cH:23][cH:24][n:25][cH:26]2)[c:15]1[F:16].[NH2:13][OH:14]>>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][c:11](... | CN(Cc1cc(-c2cccc(C=O)c2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.NO | CN(Cc1cc(-c2cccc(C=NO)c2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | null | null | CC(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 26f32c058bcc6b69b34e9c38433bccb165270e0a55ab24439c783c1aee9d8dac | 3593c4a8dedbac5f92a1a749cef37ecd686935362f91b9154f0c9930a5edea38 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[O;D1;H1:6]-[N;H0;D2;+0:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 80 | [{"value": 80.0, "product": "FC1=C(C=CC=C1C=NO)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.9, "product": "FC1=C(C=CC=C1C=NO)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution (3 mL) of tert-butyl{[5-(2-fluoro-3-formylphenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (182 mg) in 2-propanol were added hydroxylamine hydrochloride (40 mg) and sodium acetate (47 mg). After stirring at room temperature for 3 hr, saturated aqueous sodium hydrogencarbonate solutio... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Oxime | null | null | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HO- | CC(C)O | null | 3 | CN(Cc1cc(-c2cccc(C=O)c2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.NO>CC(C)O>CN(Cc1cc(-c2cccc(C=NO)c2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-26031506c17e4b9db5e5157307bed460 | CN(Cc1cc(-c2cccc(C=NO)c2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C>>CN(Cc1cc(-c2cccc(C#N)c2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | O.FC1=C(C=CC=C1C=NO)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C.C(C)N(CC)CC.CS(=O)(=O)Cl>>C(#N)C=1C(=C(C=CC1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C)F | O[N:13]=[CH:12][c:11]1[cH:10][cH:9][cH:8][c:7](-[c:6]2[cH:5][c:4]([CH2:3][N:2]([CH3:1])[C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33])[cH:26][n:16]2[S:17](=[O:18])(=[O:19])[c:20]2[cH:21][cH:22][cH:23][n:24][cH:25]2)[c:14]1[F:15]>>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][c:11]([C:12]#[N:... | CN(Cc1cc(-c2cccc(C=NO)c2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | CN(Cc1cc(-c2cccc(C#N)c2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | null | null | O1CCCC1 | Functional Group Interconversion | OtherReaction | 17f476cc256704e312f02cdb730538a4d2e78e129aaed9ef4aa555a9b052c890 | 9ad4e779dba60265752423413bc1b61ff9562539f91b24f3b3d9205e4bb46232 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | O-[N;H0;D2;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5] | 73.4 | [{"value": 73.0, "product": "C(#N)C=1C(=C(C=CC1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.4, "product": "C(#N)C=1C(=C(C=CC1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 8 | HOUR | To a solution (5 mL) of tert-butyl {[5-{2-fluoro-3-[(hydroxyimino)methyl]phenyl}-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (150 mg) in tetrahydrofuran were added triethylamine (93 mg) and methanesulfonyl chloride (84 mg) at room temperature. The reaction mixture was stirred at 70° C. for 8 hr, and ... | 10.6084/m9.figshare.5104873.v1 | null | Oxime | Nitrile | null | null | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HO- | O1CCCC1 | 70 | 8 | CN(Cc1cc(-c2cccc(C=NO)c2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C>O1CCCC1>CN(Cc1cc(-c2cccc(C#N)c2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7fa40e8c7b76432192b5e42f2048969e | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.OB(O)c1cscc1Br>>CN(Cc1cc(-c2cscc2Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | C([O-])([O-])=O.[Na+].[Na+].BrC1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C.BrC=1C(=CSC1)B(O)O>>BrC=1C(=CSC1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C | Br[c:6]1[cH:5][c:4]([CH2:3][N:2]([CH3:1])[C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])[cH:23][n:13]1[S:14](=[O:15])(=[O:16])[c:17]1[cH:18][cH:19][cH:20][n:21][cH:22]1.OB(O)[c:7]1[cH:8][s:9][cH:10][c:11]1[Br:12]>>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][s:9][cH:10][c:11]2[Br:12])[n:13]([S:14](=[O:1... | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.OB(O)c1cscc1Br | CN(Cc1cc(-c2cscc2Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | C-C Coupling | Suzuki coupling with boronic acids | 487361cf9c8a098c20bfd7c2c5754120927e29e3849a70b2ee791c6972a05de5 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=S(=O)(c1cccnc1)n1cccc1-c1ccsc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:1-[#16:6].O-B(-O)-[c;H0;D3;+0:7]1:[c:8]:[#16;a:9]:[c:10]:[c:11]:1-[Br;D1;H0:12]>>[#16:6]-[#7;a:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:7]1:[c:8]:[#16;a:9]:[c:10]:[c:11]:1-[Br;D1;H0:12] | 92 | [{"value": 92.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By a similar operation as in Reference Example 79 and using tert-butyl {[5-bromo-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (430 mg), (4-bromo-3-thienyl)boronic acid (248 mg), sodium carbonate (254 mg) and tetrakis(triphenylphosphine)palladium (116 mg), the title compound was obtained as a pale-yell... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc[nH]c1.c1ccsc1 | c1cc[nH]c1.c1ccsc1 | c1cc[nH]c1.c1ccsc1.c1ccncc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | null | CN(Cc1cc(Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.OB(O)c1cscc1Br>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1>CN(Cc1cc(-c2cscc2Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e4e1353da35943b5aed4126e8a4a3946 | CN(Cc1cc(-c2cscc2Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C>>CN(Cc1cc(-c2cscc2C#N)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | BrC=1C(=CSC1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C.CN(C=O)C>>C(#N)C=1C(=CSC1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C | Br[c:11]1[c:7](-[c:6]2[cH:5][c:4]([CH2:3][N:2]([CH3:1])[C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[cH:24][n:14]2[S:15](=[O:16])(=[O:17])[c:18]2[cH:19][cH:20][cH:21][n:22][cH:23]2)[cH:8][s:9][cH:10]1>>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][s:9][cH:10][c:11]2[C:12]#[N:13])[n:14]([S:15](=[O:16])(... | CN(Cc1cc(-c2cscc2Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | CN(Cc1cc(-c2cscc2C#N)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | null | [C-]#N.[Zn+2].[C-]#N.C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | Miscellaneous | OtherReaction | ebc2e53b7bb2dea43338a6ebf76eca4e26da1c045bb86707697af7150e28603d | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | O=S(=O)(c1cccnc1)n1cccc1-c1ccsc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#16;a:3]:[c:4]:[c:5]:1-[c:6]:[#7;a:7]>>[#7;a:7]:[c:6]-[c:5]1:[c:4]:[#16;a:3]:[c:2]:[c;H0;D3;+0:1]:1-[C:8]#[N;D1;H0:9] | 71 | [{"value": 71.0, "product": "C(#N)C=1C(=CSC1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | To a solution (5 mL) of tert-butyl {[5-(4-bromo-3-thienyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (470 mg) in N,N-dimethylformamide were added zinc cyanide (215 mg) and tetrakis(triphenylphosphine)palladium (212 mg) and the mixture was sufficiently degassed. The mixture was stirred with heating ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccsc1 | c1ccsc1 | c1cc[nH]c1.c1ccsc1.c1ccncc1 | Br- | [C-]#N.[Zn+2].[C-]#N.C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | 120 | null | CN(Cc1cc(-c2cscc2Br)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C>[C-]#N.[Zn+2].[C-]#N.C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1>CN(Cc1cc(-c2cscc2C#N)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bc30b0b5f94249a4883bc6b18506480c | CN.CO.O=C([O-])O.O=Cc1cc(-c2ccccc2F)n(S(=O)(=O)c2cccnc2)c1>>CNCc1cc(-c2ccccc2F)n(S(=O)(=O)c2cccnc2)c1.O=C(O)/C=C/C(=O)O | Cl.FC1=C(C=CC=C1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)C=O.CO.CN.C(O)([O-])=O.[Na+].[BH4-].[Na+]>>C(\C=C\C(=O)O)(=O)O.FC1=C(C=CC=C1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CNC | [CH3:1][NH2:2].[CH3:26][OH:27].[O-][C:30](=[O:31])[OH:32].[CH:3]([c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[F:13])[n:14]([S:15](=[O:16])(=[O:17])[c:18]2[cH:19][cH:20][cH:21][n:22][cH:23]2)[cH:24]1)=[O:25]>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[F:13])[n:14]([S:15]... | CN.CO.O=C([O-])O.O=Cc1cc(-c2ccccc2F)n(S(=O)(=O)c2cccnc2)c1 | CNCc1cc(-c2ccccc2F)n(S(=O)(=O)c2cccnc2)c1.O=C(O)/C=C/C(=O)O | null | null | CO | C-C Coupling | OtherReaction | 0a605e925875fd65b9b2cb49daa436da4548265f3a1a9496b2721d18503f4e01 | fd98091f83c9c9233753685e3e98b99ddf33a81d8eeee2f387ca4a01bfcbe777 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | [#16:1]-[#7;a:2]1:[c:3]:[c:4](-[CH;D2;+0:5]=[O;H0;D1;+0:6]):[c:7]:[c:8]:1.[C;D1;H3:9]-[NH2;D1;+0:10].[CH3;D1;+0:11]-[O;D1;H1:12].[O-]-[C;H0;D3;+0:13](=[O;D1;H0:14])-[O;D1;H1:15]>>[#16:1]-[#7;a:2]1:[c:3]:[c:4](-[CH2;D2;+0:5]-[NH;D2;+0:10]-[C;D1;H3:9]):[c:7]:[c:8]:1.[O;D1;H0:14]=[C;H0;D3;+0:13](-[O;D1;H1:15])/[C:16]=[C:1... | null | [] | null | null | 30 | MINUTE | 5-(2-Fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde (1.52 g) was dissolved in methanol (30 mL), a 40% methylamine methanol solution (3.57 g) was added at room temperature and the mixture was stirred for 30 min. Sodium borohydride (523 mg) was added at room temperature and the mixture was stirred for 1... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Carbonic Acid.Primary amine.Methanol | Carboxylic acid.Carboxylic acid.Secondary amine | null | null | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HO- | CO | null | 0.5 | CN.CO.O=C([O-])O.O=Cc1cc(-c2ccccc2F)n(S(=O)(=O)c2cccnc2)c1>CO>CNCc1cc(-c2ccccc2F)n(S(=O)(=O)c2cccnc2)c1.O=C(O)/C=C/C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-23487a1ea3584d0d9da6cbbaf7fdcb22 | CN.O=Cc1cc(-c2ccccc2C(F)(F)F)n(S(=O)(=O)c2cccnc2)c1>>CNCc1cc(-c2ccccc2C(F)(F)F)n(S(=O)(=O)c2cccnc2)c1.Cl | Cl.N1=CC(=CC=C1)S(=O)(=O)N1C=C(C=C1C1=C(C=CC=C1)C(F)(F)F)C=O.CO.CN.C(O)([O-])=O.[Na+].[BH4-].[Na+]>>Cl.Cl.CNCC1=CN(C(=C1)C1=C(C=CC=C1)C(F)(F)F)S(=O)(=O)C=1C=NC=CC1 | [CH3:1][NH2:2].O=[CH:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[C:13]([F:14])([F:15])[F:16])[n:17]([S:18](=[O:19])(=[O:20])[c:21]2[cH:22][cH:23][cH:24][n:25][cH:26]2)[cH:27]1>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[C:13]([F:14])([F:15])[F:16])[n:17]([S:18](=[O:1... | CN.O=Cc1cc(-c2ccccc2C(F)(F)F)n(S(=O)(=O)c2cccnc2)c1 | CNCc1cc(-c2ccccc2C(F)(F)F)n(S(=O)(=O)c2cccnc2)c1.Cl | null | null | C(C)O | Functional Group Interconversion | Reductive amination with aldehyde | 7d1b6092237fd369773eab744edec53855841c9fba6370f9ea667d17afb10a43 | 349d032a341f28a5e8c653eea4b45ad75ec46e02d142d0018cfaf68db09826d4 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4](-[#16:5]):[c:6]:[c:7]:1.[C;D1;H3:8]-[NH2;D1;+0:9]>>[#16:5]-[#7;a:4]1:[c:3]:[c:2](-[CH2;D2;+0:1]-[NH;D2;+0:9]-[C;D1;H3:8]):[c:7]:[c:6]:1 | 69 | [{"value": 69.0, "product": "Cl.Cl.CNCC1=CN(C(=C1)C1=C(C=CC=C1)C(F)(F)F)S(=O)(=O)C=1C=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 1-(Pyridin-3-ylsulfonyl)-5-[2-(trifluoromethyl)phenyl]-1H-pyrrole-3-carbaldehyde (340 mg) was dissolved in ethanol (34 mL), a 40% methylamine methanol solution (695 mg) was added at room temperature and the mixture was stirred for 30 min. Sodium borohydride (102 mg) was added at room temperature and the mixture was sti... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1cc[nH]c1.c1ccccc1.c1ccncc1 | null | C(C)O | null | 0.5 | CN.O=Cc1cc(-c2ccccc2C(F)(F)F)n(S(=O)(=O)c2cccnc2)c1>C(C)O>CNCc1cc(-c2ccccc2C(F)(F)F)n(S(=O)(=O)c2cccnc2)c1.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-00c09674435b450e97fbf7f3f21188ed | CN(Cc1cc(-c2ccccc2)n(S(=O)(=O)c2cccnc2Cl)c1)C(=O)OC(C)(C)C>>CNCc1cc(-c2ccccc2)n(S(=O)(=O)c2cccnc2Cl)c1 | C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)C1=CC=CC=C1)S(=O)(=O)C=1C(=NC=CC1)Cl)=O.C(C)(=O)OCC.Cl>>Cl.ClC1=NC=CC=C1S(=O)(=O)N1C=C(C=C1C1=CC=CC=C1)CNC | CC(C)(C)OC(=O)[N:2]([CH3:1])[CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[n:13]([S:14](=[O:15])(=[O:16])[c:17]2[cH:18][cH:19][cH:20][n:21][c:22]2[Cl:23])[cH:24]1>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[n:13]([S:14](=[O:15])(=[O:16])[c:17]2[cH:18][cH:19][cH... | CN(Cc1cc(-c2ccccc2)n(S(=O)(=O)c2cccnc2Cl)c1)C(=O)OC(C)(C)C | CNCc1cc(-c2ccccc2)n(S(=O)(=O)c2cccnc2Cl)c1 | null | null | C(C)(=O)OCC | Reduction | Boc amine deprotection | bbda4640db5f48af4538caded12fdadd56eacd6d4e5f7aefe46282d665df167e | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:3]-[NH;D2;+0:1]-[C;D1;H3:2] | 96.1 | [{"value": 49.0, "product": "Cl.ClC1=NC=CC=C1S(=O)(=O)N1C=C(C=C1C1=CC=CC=C1)CNC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.1, "product": "Cl.ClC1=NC=CC=C1S(=O)(=O)N1C=C(C=C1C1=CC=CC=C1)CNC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution (3 mL) of tert-butyl{[1-(2-chloro-3-pyridinesulfonyl)-5-phenyl-1H-pyrrol-3-yl]methyl}methylcarbamate (70 mg) in ethyl acetate was added a 4 mol/L hydrogen chloride-ethyl acetate solution (1 mL), and the mixture was stirred at room temperature for 3 hr. The solvent was evaporated under reduced pressure, an... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | null | null | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HO- | C(C)(=O)OCC | null | 3 | CN(Cc1cc(-c2ccccc2)n(S(=O)(=O)c2cccnc2Cl)c1)C(=O)OC(C)(C)C>C(C)(=O)OCC>CNCc1cc(-c2ccccc2)n(S(=O)(=O)c2cccnc2Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-85801938e66047ab856535a7ca1f64cf | CCOC(C)=O.Cc1cc(S(=O)(=O)n2cc(CN(C)C(=O)OC(C)(C)C)cc2-c2ccccc2)cnc1Cl.O=C([O-])O>>CNCc1cc(-c2ccccc2)n(S(=O)(=O)c2cncc(C)c2)c1.O=C(O)/C=C/C(=O)O | C(C)(=O)OCC.Cl.C(O)([O-])=O.[Na+].ClC1=C(C=C(C=N1)S(=O)(=O)N1C=C(C=C1C1=CC=CC=C1)CN(C(OC(C)(C)C)=O)C)C.NN>>C(\C=C\C(=O)O)(=O)O.CNCC1=CN(C(=C1)C1=CC=CC=C1)S(=O)(=O)C=1C=NC=C(C1)C | CCO[C:29](=O)[CH3:28].CC(C)(C)[O:32][C:30]([N:2]([CH3:1])[CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[n:13]([S:14](=[O:15])(=[O:16])[c:17]2[cH:18][n:19][c:20](Cl)[c:21]([CH3:22])[cH:23]2)[cH:24]1)=[O:31].[O-][C:26](=[O:25])[OH:27]>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][... | CCOC(C)=O.Cc1cc(S(=O)(=O)n2cc(CN(C)C(=O)OC(C)(C)C)cc2-c2ccccc2)cnc1Cl.O=C([O-])O | CNCc1cc(-c2ccccc2)n(S(=O)(=O)c2cncc(C)c2)c1.O=C(O)/C=C/C(=O)O | null | null | O1CCCC1.C(C)O | C-C Coupling | OtherReaction | e87e13069b1080103e17ce269338e5a993e10d2d02e8a08624789f801c3cf904 | be4200df74cbeda5aced664931b431d459b27627e8a4136273569d95010f98e0 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[N;H0;D3;+0:4](-[C;D1;H3:5])-[C:6]-[c:7]:[c:8]:[#7;a:9].Cl-[c;H0;D3;+0:10](:[#7;a:11]:[c:12]):[c:13](-[C;D1;H3:14]):[c:15].C-C-O-[C;H0;D3;+0:16](=O)-[CH3;D1;+0:17].[O-]-[C;H0;D3;+0:18](=[O;D1;H0:19])-[O;D1;H1:20]>>[#7;a:9]:[c:8]:[c:7]-[C:6]-[NH;D2;+0:4]-[C;D1;H3:5... | 40 | [{"value": 40.0, "product": "C(\\C=C\\C(=O)O)(=O)O.CNCC1=CN(C(=C1)C1=CC=CC=C1)S(=O)(=O)C=1C=NC=C(C1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution (5 mL) of tert-butyl {[1-(6-chloro-5-methyl-3-pyridinesulfonyl)-5-phenyl-1H-pyrrol-3-yl]methyl}methylcarbamate (237 mg) in tetrahydrofuran was added hydrazine (160 mg) at room temperature with stirring. After stirring at the same temperature for 3 hr, a saturated aqueous sodium hydrogencarbonate solution ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester.Carbonic Acid.Ester.Ether.Boc | Carboxylic acid.Carboxylic acid.Secondary amine | c1ccncc1 | c1ccncc1 | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HCl | O1CCCC1.C(C)O | null | 0.5 | CCOC(C)=O.Cc1cc(S(=O)(=O)n2cc(CN(C)C(=O)OC(C)(C)C)cc2-c2ccccc2)cnc1Cl.O=C([O-])O>O1CCCC1.C(C)O>CNCc1cc(-c2ccccc2)n(S(=O)(=O)c2cncc(C)c2)c1.O=C(O)/C=C/C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-367c5f6b1e814262992c461a262c74be | CN(Cc1cc(-c2ccccc2)n(S(=O)(=O)c2ccc(Cl)nc2)c1)C(=O)OC(C)(C)C>>CNCc1cc(-c2ccccc2)n(S(=O)(=O)c2ccc(O)nc2)c1.Cl | ClC1=CC=C(C=N1)S(=O)(=O)N1C=C(C=C1C1=CC=CC=C1)CN(C(OC(C)(C)C)=O)C.[OH-].[Na+].O>>Cl.CNCC=1C=C(N(C1)S(=O)(=O)C=1C=CC(=NC1)O)C1=CC=CC=C1 | CC(C)(C)OC([N:2]([CH3:1])[CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[n:13]([S:14](=[O:15])(=[O:16])[c:17]2[cH:18][cH:19][c:20]([Cl:25])[n:22][cH:23]2)[cH:24]1)=[O:21]>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[n:13]([S:14](=[O:15])(=[O:16])[c:17]2[cH:18][cH... | CN(Cc1cc(-c2ccccc2)n(S(=O)(=O)c2ccc(Cl)nc2)c1)C(=O)OC(C)(C)C | CNCc1cc(-c2ccccc2)n(S(=O)(=O)c2ccc(O)nc2)c1.Cl | null | null | O1CCCC1 | Miscellaneous | OtherReaction | ef10cba1c40db98ca2cbeaa63622df64b98772fea85a322dc528330edaecccb3 | 9a28f6ad5aacdc6a99219b8a21f7421d43118498deed2dfba6a2c4c005a60419 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | C-C(-C)(-C)-O-C(=[O;H0;D1;+0:1])-[N;H0;D3;+0:2](-[C;D1;H3:3])-[C:4]-[c:5]:[c:6]:[#7;a:7].[Cl;H0;D1;+0:8]-[c;H0;D3;+0:9](:[#7;a:10]:[c:11]):[c:12]:[c:13]>>[#7;a:7]:[c:6]:[c:5]-[C:4]-[NH;D2;+0:2]-[C;D1;H3:3].[OH;D1;+0:1]-[c;H0;D3;+0:9](:[#7;a:10]:[c:11]):[c:12]:[c:13].[ClH;D0;+0:8] | null | [] | 50 | CELSIUS | 2 | DAY | tert-Butyl {[1-(6-chloro-3-pyridinesulfonyl)-5-phenyl-1H-pyrrol-3-yl]methyl}methylcarbamate (175 mg) was dissolved in tetrahydrofuran (10 mL), a 8 mol/L aqueous sodium hydroxide solution (3.8 mL) was added, and the mixture was stirred at 50° C. for 2 days. Water was added to the reaction mixture, and the mixture was ex... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester.Ether.Boc | Aromatic alcohol.Secondary amine | c1ccncc1 | c1ccncc1 | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HO- | O1CCCC1 | 50 | 48 | CN(Cc1cc(-c2ccccc2)n(S(=O)(=O)c2ccc(Cl)nc2)c1)C(=O)OC(C)(C)C>O1CCCC1>CNCc1cc(-c2ccccc2)n(S(=O)(=O)c2ccc(O)nc2)c1.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-19234356e9f74460af3c01daba87d2e0 | CN(Cc1cc(-c2ccccc2)n(S(=O)(=O)c2ccc(Cl)nc2)c1)C(=O)OC(C)(C)C>>CNCc1cc(-c2ccccc2)n(S(=O)(=O)c2ccc(C#N)nc2)c1 | C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)C1=CC=CC=C1)S(=O)(=O)C=1C=NC(=CC1)Cl)=O.CN(C=O)C.C(C)(=O)OCC.Cl>>Cl.CNCC=1C=C(N(C1)S(=O)(=O)C=1C=CC(=NC1)C#N)C1=CC=CC=C1 | CC(C)(C)OC(=O)[N:2]([CH3:1])[CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[n:13]([S:14](=[O:15])(=[O:16])[c:17]2[cH:18][cH:19][c:20](Cl)[n:23][cH:24]2)[cH:25]1>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[n:13]([S:14](=[O:15])(=[O:16])[c:17]2[cH:18][cH:19][c:20]... | CN(Cc1cc(-c2ccccc2)n(S(=O)(=O)c2ccc(Cl)nc2)c1)C(=O)OC(C)(C)C | CNCc1cc(-c2ccccc2)n(S(=O)(=O)c2ccc(C#N)nc2)c1 | null | [C-]#N.[Zn+2].[C-]#N.C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C(C)(=O)OCC | Miscellaneous | OtherReaction | 65fb274b9e40f0c73e43dcee64f9109c6f96aabdce8e472231611ca5fe7a8006 | 1057828eb7854b3bc292e1cd602b9bc4b8e879a7adfc7e5babd071ec27c3bf86 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[c:4]:[c:5]:[#7;a:6].Cl-[c;H0;D3;+0:7](:[#7;a:8]:[c:9]):[c:10]:[c:11]>>[#7;a:6]:[c:5]:[c:4]-[C:3]-[NH;D2;+0:1]-[C;D1;H3:2].[N;D1;H0:12]#[C:13]-[c;H0;D3;+0:7](:[#7;a:8]:[c:9]):[c:10]:[c:11] | 68 | [{"value": 68.0, "product": "Cl.CNCC=1C=C(N(C1)S(=O)(=O)C=1C=CC(=NC1)C#N)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 2 | HOUR | Under an argon atmosphere, a mixture of tert-butyl{[1-(6-chloro-3-pyridinesulfonyl)-5-phenyl-1H-pyrrol-3-yl]methyl}methylcarbamate (100 mg), zinc (II) cyanide (51 mg), tetrakis(triphenylphosphine)palladium (50 mg) and N,N-dimethylformamide (4 mL) was stirred at 100° C. for 2 hr. The reaction mixture was diluted with et... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester.Ether.Boc | Nitrile.Secondary amine | c1ccncc1 | c1ccncc1 | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HCl | [C-]#N.[Zn+2].[C-]#N.C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C(C)(=O)OCC | 100 | 2 | CN(Cc1cc(-c2ccccc2)n(S(=O)(=O)c2ccc(Cl)nc2)c1)C(=O)OC(C)(C)C>[C-]#N.[Zn+2].[C-]#N.C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C(C)(=O)OCC>CNCc1cc(-c2ccccc2)n(S(=O)(=O)c2ccc(C#N)nc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6fcf058be28741cea7563a87455b9037 | CN(Cc1cc(-c2ccc(F)cc2)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.ClCCl>>CNCc1cc(-c2ccc(F)cc2)n(S(=O)(=O)c2cccnc2)c1.Cl.Cl | FC1=CC=C(C=C1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C.ClCCl.FC(C(=O)O)(F)F.C(O)([O-])=O.[Na+]>>Cl.Cl.FC1=CC=C(C=C1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CNC | CC(C)(C)OC(=O)[N:2]([CH3:1])[CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[n:14]([S:15](=[O:16])(=[O:17])[c:18]2[cH:19][cH:20][cH:21][n:22][cH:23]2)[cH:24]1.C([Cl:25])[Cl:26]>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[n:14]([S:15](=[O:16])(=[O:17... | CN(Cc1cc(-c2ccc(F)cc2)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.ClCCl | CNCc1cc(-c2ccc(F)cc2)n(S(=O)(=O)c2cccnc2)c1.Cl.Cl | null | null | null | Miscellaneous | OtherReaction | d5c00134b46725a233b056828144ae17a788b8b64d6f419672c7619603d6f1d1 | 016f034d4f383e2d40e897f441602a7d95bad94b528953d03d8a2ec434dca97e | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[c:4]:[c:5]:[#7;a:6].[Cl;H0;D1;+0:7]-C-[Cl;H0;D1;+0:8]>>[#7;a:6]:[c:5]:[c:4]-[C:3]-[NH;D2;+0:1]-[C;D1;H3:2].[ClH;D0;+0:7].[ClH;D0;+0:8] | null | [] | null | null | 3 | HOUR | tert-Butyl {[5-(4-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (293 mg) was dissolved in dichloromethane (1 mL), trifluoroacetic acid (1 mL) was added at 0° C., and the mixture was stirred at room temperature for 3 hr. The reaction solution was basified by adding dropwise to a 6% aqueous... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Carbamic ester.Ether.Boc | Secondary amine | null | null | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HO- | null | null | 3 | CN(Cc1cc(-c2ccc(F)cc2)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.ClCCl>>CNCc1cc(-c2ccc(F)cc2)n(S(=O)(=O)c2cccnc2)c1.Cl.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-02929bb33f6c4b8c85f121d961699d80 | Cc1ccccc1-c1cc(CN(C)C(=O)OC(C)(C)C)cn1S(=O)(=O)c1cccnc1.ClCCl>>CNCc1cc(-c2ccccc2C)n(S(=O)(=O)c2cccnc2)c1.Cl.Cl | CN(C(OC(C)(C)C)=O)CC1=CN(C(=C1)C1=C(C=CC=C1)C)S(=O)(=O)C=1C=NC=CC1.ClCCl.FC(C(=O)O)(F)F.C(O)([O-])=O.[Na+]>>Cl.Cl.CNCC1=CN(C(=C1)C1=C(C=CC=C1)C)S(=O)(=O)C=1C=NC=CC1 | CC(C)(C)OC(=O)[N:2]([CH3:1])[CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[CH3:13])[n:14]([S:15](=[O:16])(=[O:17])[c:18]2[cH:19][cH:20][cH:21][n:22][cH:23]2)[cH:24]1.C([Cl:25])[Cl:26]>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[CH3:13])[n:14]([S:15](=[O:16])(=[O:17... | Cc1ccccc1-c1cc(CN(C)C(=O)OC(C)(C)C)cn1S(=O)(=O)c1cccnc1.ClCCl | CNCc1cc(-c2ccccc2C)n(S(=O)(=O)c2cccnc2)c1.Cl.Cl | null | null | null | Miscellaneous | OtherReaction | d5c00134b46725a233b056828144ae17a788b8b64d6f419672c7619603d6f1d1 | 016f034d4f383e2d40e897f441602a7d95bad94b528953d03d8a2ec434dca97e | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[c:4]:[c:5]:[#7;a:6].[Cl;H0;D1;+0:7]-C-[Cl;H0;D1;+0:8]>>[#7;a:6]:[c:5]:[c:4]-[C:3]-[NH;D2;+0:1]-[C;D1;H3:2].[ClH;D0;+0:7].[ClH;D0;+0:8] | null | [] | null | null | 2 | HOUR | By a similar operation as in Example 26 and using tert-butyl methyl{[5-(2-methylphenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}carbamate (210 mg), the title compound was obtained as colorless crystals (yield 67 mg, 34%). More specifically, tert-butyl methyl{[5-(2-methylphenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Carbamic ester.Ether.Boc | Secondary amine | null | null | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HO- | null | null | 2 | Cc1ccccc1-c1cc(CN(C)C(=O)OC(C)(C)C)cn1S(=O)(=O)c1cccnc1.ClCCl>>CNCc1cc(-c2ccccc2C)n(S(=O)(=O)c2cccnc2)c1.Cl.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1b51617b1f3647518381053fa544333a | Cc1cscc1-c1cc(CN(C)C(=O)OC(C)(C)C)cn1S(=O)(=O)c1cccnc1.ClCCl>>CNCc1cc(-c2cscc2C)n(S(=O)(=O)c2cccnc2)c1.Cl.Cl | CN(C(OC(C)(C)C)=O)CC1=CN(C(=C1)C1=CSC=C1C)S(=O)(=O)C=1C=NC=CC1.ClCCl.FC(C(=O)O)(F)F.C(O)([O-])=O.[Na+]>>Cl.Cl.CNCC1=CN(C(=C1)C1=CSC=C1C)S(=O)(=O)C=1C=NC=CC1 | CC(C)(C)OC(=O)[N:2]([CH3:1])[CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][s:9][cH:10][c:11]2[CH3:12])[n:13]([S:14](=[O:15])(=[O:16])[c:17]2[cH:18][cH:19][cH:20][n:21][cH:22]2)[cH:23]1.C([Cl:24])[Cl:25]>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][s:9][cH:10][c:11]2[CH3:12])[n:13]([S:14](=[O:15])(=[O:16])[c:17]2[cH:18]... | Cc1cscc1-c1cc(CN(C)C(=O)OC(C)(C)C)cn1S(=O)(=O)c1cccnc1.ClCCl | CNCc1cc(-c2cscc2C)n(S(=O)(=O)c2cccnc2)c1.Cl.Cl | null | null | null | Miscellaneous | OtherReaction | d5c00134b46725a233b056828144ae17a788b8b64d6f419672c7619603d6f1d1 | 016f034d4f383e2d40e897f441602a7d95bad94b528953d03d8a2ec434dca97e | O=S(=O)(c1cccnc1)n1cccc1-c1ccsc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[c:4]:[c:5]:[#7;a:6].[Cl;H0;D1;+0:7]-C-[Cl;H0;D1;+0:8]>>[#7;a:6]:[c:5]:[c:4]-[C:3]-[NH;D2;+0:1]-[C;D1;H3:2].[ClH;D0;+0:7].[ClH;D0;+0:8] | null | [] | null | null | 1 | HOUR | By a similar operation as in Example 26 and using tert-butyl methyl{[5-(4-methyl-3-thienyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}carbamate (200 mg), the title compound was obtained as colorless crystals (yield 125 mg, 67%). More specifically, tert-butyl methyl{[5-(4-methyl-3-thienyl)-1-(pyridin-3-ylsulfonyl)-... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Carbamic ester.Ether.Boc | Secondary amine | null | null | c1cc[nH]c1.c1ccsc1.c1ccncc1 | HO- | null | null | 1 | Cc1cscc1-c1cc(CN(C)C(=O)OC(C)(C)C)cn1S(=O)(=O)c1cccnc1.ClCCl>>CNCc1cc(-c2cscc2C)n(S(=O)(=O)c2cccnc2)c1.Cl.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-18d4ca2772db43a7a9ad96b52fff9f4d | CN(Cc1cc(-c2cccc(F)c2)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C>>CNCc1cc(-c2cccc(F)c2)n(S(=O)(=O)c2cccnc2)c1 | C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)C1=CC(=CC=C1)F)S(=O)(=O)C=1C=NC=CC1)=O.C(C)(=O)OCC.Cl.C(O)([O-])=O.[Na+]>>Cl.FC=1C=C(C=CC1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CNC | CC(C)(C)OC(=O)[N:2]([CH3:1])[CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][c:11]([F:12])[cH:13]2)[n:14]([S:15](=[O:16])(=[O:17])[c:18]2[cH:19][cH:20][cH:21][n:22][cH:23]2)[cH:24]1>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][c:11]([F:12])[cH:13]2)[n:14]([S:15](=[O:16])(=[O:17])[c:18]2[cH:19][c... | CN(Cc1cc(-c2cccc(F)c2)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | CNCc1cc(-c2cccc(F)c2)n(S(=O)(=O)c2cccnc2)c1 | null | null | C(C)(=O)OCC | Reduction | Boc amine deprotection | bbda4640db5f48af4538caded12fdadd56eacd6d4e5f7aefe46282d665df167e | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:3]-[NH;D2;+0:1]-[C;D1;H3:2] | null | [] | null | null | 16 | HOUR | tert-Butyl{[5-(3-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (280 mg) was dissolved in ethyl acetate (3 mL), a 4 mol/L hydrogen chloride-ethyl acetate solution (6 mL) was added, and the mixture was stirred at room temperature for 16 hr. The reaction solution was basified by adding dropw... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | null | null | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HO- | C(C)(=O)OCC | null | 16 | CN(Cc1cc(-c2cccc(F)c2)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C>C(C)(=O)OCC>CNCc1cc(-c2cccc(F)c2)n(S(=O)(=O)c2cccnc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5fdb655fcdd443919fd9760b8e9bceb8 | CN.O=Cc1cn(S(=O)(=O)c2cccnc2)c(-c2ccccc2)c1F>>CNCc1cn(S(=O)(=O)c2cccnc2)c(-c2ccccc2)c1F | CN.FC=1C(=CN(C1C1=CC=CC=C1)S(=O)(=O)C=1C=NC=CC1)C=O.[BH4-].[Na+].CO>>FC=1C(=CN(C1C1=CC=CC=C1)S(=O)(=O)C=1C=NC=CC1)CNC | [CH3:1][NH2:2].O=[CH:3][c:4]1[cH:5][n:6]([S:7](=[O:8])(=[O:9])[c:10]2[cH:11][cH:12][cH:13][n:14][cH:15]2)[c:16](-[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[c:23]1[F:24]>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][n:6]([S:7](=[O:8])(=[O:9])[c:10]2[cH:11][cH:12][cH:13][n:14][cH:15]2)[c:16](-[c:17]2[cH:18][cH:19][cH:20][cH:21][cH... | CN.O=Cc1cn(S(=O)(=O)c2cccnc2)c(-c2ccccc2)c1F | CNCc1cn(S(=O)(=O)c2cccnc2)c(-c2ccccc2)c1F | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5](-[#16:6]):[c:7]:1.[C;D1;H3:8]-[NH2;D1;+0:9]>>[#16:6]-[#7;a:5]1:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[NH;D2;+0:9]-[C;D1;H3:8]):[c:7]:1 | 39 | [{"value": 39.0, "product": "FC=1C(=CN(C1C1=CC=CC=C1)S(=O)(=O)C=1C=NC=CC1)CNC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 4-Fluoro-5-phenyl-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde (0.27 g) was dissolved in tetrahydrofuran (10 mL), a 2 mol/L solution (0.8 mL) of methylamine in tetrahydrofuran was added, and the mixture was stirred at room temperature for 2 hr. Sodium borohydride (91 mg) and methanol (7 mL) were added, and the mi... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1cc[nH]c1.c1ccncc1.c1ccccc1 | Other | O1CCCC1 | null | 2 | CN.O=Cc1cn(S(=O)(=O)c2cccnc2)c(-c2ccccc2)c1F>O1CCCC1>CNCc1cn(S(=O)(=O)c2cccnc2)c(-c2ccccc2)c1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-53b858c7e1e04d4c877b362dbc5462a5 | C1CCOC1.CN.CO.Cc1ccccc1-c1cc(C=O)cn1S(=O)(=O)c1cccnc1.O>>CNCc1cc(-c2ccccc2C)n(S(=O)(=O)c2cccnc2)c1.O=C(O)/C=C/C(=O)O | O.[BH4-].[Na+].CC1=C(C=CC=C1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)C=O.CO.CN.O1CCCC1>>C(\C=C\C(=O)O)(=O)O.CNCC1=CN(C(=C1)C1=C(C=CC=C1)C)S(=O)(=O)C=1C=NC=CC1 | C1[O:17][CH2:30][CH2:29][CH2:28]1.[CH3:1][NH2:2].[CH3:26][OH:27].[CH:3]([c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[CH3:13])[n:14]([S:15](=[O:16])([c:18]2[cH:19][cH:20][cH:21][n:22][cH:23]2)=[O:25])[cH:24]1)=[O:31].[OH2:32]>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[C... | C1CCOC1.CN.CO.Cc1ccccc1-c1cc(C=O)cn1S(=O)(=O)c1cccnc1.O | CNCc1cc(-c2ccccc2C)n(S(=O)(=O)c2cccnc2)c1.O=C(O)/C=C/C(=O)O | null | null | CO | Acylation | OtherReaction | 7e2ad918b73cdbcabb395f5c91e75ccc1ba842f47c26cee594645c1094937ad4 | 3a5ae6ba2fbec8cd2490fbc510db817be75b8affbf2c80b952cbe8065e7c0a33 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | C1-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[O;H0;D2;+0:4]-1.[C;D1;H3:5]-[NH2;D1;+0:6].[CH3;D1;+0:7]-[O;D1;H1:8].[O;D1;H0:9]=[S;H0;D4;+0:10](=[O;H0;D1;+0:11])(-[#7;a:12]1:[c:13]:[c:14](-[CH;D2;+0:15]=[O;H0;D1;+0:16]):[c:17]:[c:18]:1)-[c:19](:[c:20]):[c:21]:[#7;a:22]:[c:23].[OH2;D0;+0:24]>>[C;D1;H3:5]-[NH;D2;+0:6]-[CH2... | null | [] | null | null | 1 | HOUR | To a solution of 5-(2-methylphenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde (521 mg) in tetrahydrofuran (5 mL) and methanol (5 mL) was added a 40% methylamine methanol solution (373 mg). After stirring at room temperature for 1 hr, sodium borohydride (202 mg) was added. After stirring at the same temperature... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ether.Primary amine.Methanol | Carboxylic acid.Carboxylic acid.Secondary amine | C1CCOC1 | null | c1cc[nH]c1.c1ccccc1.c1ccncc1 | Other | CO | null | 1 | C1CCOC1.CN.CO.Cc1ccccc1-c1cc(C=O)cn1S(=O)(=O)c1cccnc1.O>CO>CNCc1cc(-c2ccccc2C)n(S(=O)(=O)c2cccnc2)c1.O=C(O)/C=C/C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ddb70487f118486db6c55096aebb1c3a | C1CCOC1.CN.CO.O.O=Cc1cn(S(=O)(=O)c2cccnc2)c(-c2ccccc2F)c1Cl>>CNCc1cn(S(=O)(=O)c2cccnc2)c(-c2ccccc2F)c1Cl.O=C(O)/C=C/C(=O)O | O.[BH4-].[Na+].ClC=1C(=CN(C1C1=C(C=CC=C1)F)S(=O)(=O)C=1C=NC=CC1)C=O.CO.CN.O1CCCC1>>C(\C=C\C(=O)O)(=O)O.ClC=1C(=CN(C1C1=C(C=CC=C1)F)S(=O)(=O)C=1C=NC=CC1)CNC | C1[CH2:29][CH2:30][CH2:31][O:32]1.[CH3:1][NH2:2].[CH3:27][OH:28].[OH2:33].[CH:3]([c:4]1[cH:5][n:6]([S:7](=[O:8])(=[O:9])[c:10]2[cH:11][cH:12][cH:13][n:14][cH:15]2)[c:16](-[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2[F:23])[c:24]1[Cl:25])=[O:26]>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][n:6]([S:7](=[O:8])(=[O:9])[c:10]2[cH:11][cH... | C1CCOC1.CN.CO.O.O=Cc1cn(S(=O)(=O)c2cccnc2)c(-c2ccccc2F)c1Cl | CNCc1cn(S(=O)(=O)c2cccnc2)c(-c2ccccc2F)c1Cl.O=C(O)/C=C/C(=O)O | null | null | CO | Acylation | OtherReaction | 7e2ad918b73cdbcabb395f5c91e75ccc1ba842f47c26cee594645c1094937ad4 | 3a5ae6ba2fbec8cd2490fbc510db817be75b8affbf2c80b952cbe8065e7c0a33 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | C1-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[O;H0;D2;+0:4]-1.[#16:5]-[#7;a:6]1:[c:7]:[c:8]:[c:9](-[CH;D2;+0:10]=[O;H0;D1;+0:11]):[c:12]:1.[C;D1;H3:13]-[NH2;D1;+0:14].[CH3;D1;+0:15]-[O;D1;H1:16].[OH2;D0;+0:17]>>[#16:5]-[#7;a:6]1:[c:7]:[c:8]:[c:9](-[CH2;D2;+0:10]-[NH;D2;+0:14]-[C;D1;H3:13]):[c:12]:1.[O;D1;H1:16]-[C;H0;D... | null | [] | null | null | 30 | MINUTE | To a solution of 4-chloro-5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde (429 mg) in tetrahydrofuran (5 mL) and methanol (3 mL) was added a 40% methylamine methanol solution (275 mg) at room temperature. After stirring for 30 min, sodium borohydride (99 mg) was added. After stirring at the same t... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ether.Primary amine.Methanol | Carboxylic acid.Carboxylic acid.Secondary amine | C1CCOC1 | null | c1cc[nH]c1.c1ccncc1.c1ccccc1 | Other | CO | null | 0.5 | C1CCOC1.CN.CO.O.O=Cc1cn(S(=O)(=O)c2cccnc2)c(-c2ccccc2F)c1Cl>CO>CNCc1cn(S(=O)(=O)c2cccnc2)c(-c2ccccc2F)c1Cl.O=C(O)/C=C/C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-88d68714342a477a8b43eff172c0bc34 | CN(Cc1cc(-c2ccccc2)n(S(=O)(=O)c2cncc(Br)c2)c1)C(=O)OC(C)(C)C>>CNCc1cc(-c2ccccc2)n(S(=O)(=O)c2cncc(Br)c2)c1 | C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)C1=CC=CC=C1)S(=O)(=O)C=1C=NC=C(C1)Br)=O.C(C)(=O)OCC.Cl>>Cl.BrC=1C=C(C=NC1)S(=O)(=O)N1C=C(C=C1C1=CC=CC=C1)CNC | CC(C)(C)OC(=O)[N:2]([CH3:1])[CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[n:13]([S:14](=[O:15])(=[O:16])[c:17]2[cH:18][n:19][cH:20][c:21]([Br:22])[cH:23]2)[cH:24]1>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[n:13]([S:14](=[O:15])(=[O:16])[c:17]2[cH:18][n:19][c... | CN(Cc1cc(-c2ccccc2)n(S(=O)(=O)c2cncc(Br)c2)c1)C(=O)OC(C)(C)C | CNCc1cc(-c2ccccc2)n(S(=O)(=O)c2cncc(Br)c2)c1 | null | null | C(C)O | Reduction | Boc amine deprotection | bbda4640db5f48af4538caded12fdadd56eacd6d4e5f7aefe46282d665df167e | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:3]-[NH;D2;+0:1]-[C;D1;H3:2] | 49 | [{"value": 49.0, "product": "Cl.BrC=1C=C(C=NC1)S(=O)(=O)N1C=C(C=C1C1=CC=CC=C1)CNC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | tert-Butyl({1-[(5-bromopyridin-3-yl)sulfonyl]-5-phenyl-1H-pyrr-ol-3-yl}methyl)methylcarbamate (120 mg) was dissolved in ethanol (3 mL), and a 4 mol/L hydrogen chloride-ethyl acetate solution (1 mL) was added. After stirring at room temperature for 4 hr, the mixture was concentrated under reduced pressure, and the resid... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | null | null | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HO- | C(C)O | null | 4 | CN(Cc1cc(-c2ccccc2)n(S(=O)(=O)c2cncc(Br)c2)c1)C(=O)OC(C)(C)C>C(C)O>CNCc1cc(-c2ccccc2)n(S(=O)(=O)c2cncc(Br)c2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-94e31daf15374fc184a1963d777b0026 | CN(Cc1cc(-c2ccccc2)n(S(=O)(=O)c2cncc(Br)c2)c1)C(=O)OC(C)(C)C>>CNCc1cc(-c2ccccc2)n(S(=O)(=O)c2cncc(C#N)c2)c1 | C(C)(=O)OCC.Cl.C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)C1=CC=CC=C1)S(=O)(=O)C=1C=NC=C(C1)Br)=O.CN(C=O)C>>Cl.CNCC=1C=C(N(C1)S(=O)(=O)C=1C=NC=C(C#N)C1)C1=CC=CC=C1 | CC(C)(C)OC(=O)[N:2]([CH3:1])[CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[n:13]([S:14](=[O:15])(=[O:16])[c:17]2[cH:18][n:19][cH:20][c:21](Br)[cH:24]2)[cH:25]1>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[n:13]([S:14](=[O:15])(=[O:16])[c:17]2[cH:18][n:19][cH:20]... | CN(Cc1cc(-c2ccccc2)n(S(=O)(=O)c2cncc(Br)c2)c1)C(=O)OC(C)(C)C | CNCc1cc(-c2ccccc2)n(S(=O)(=O)c2cncc(C#N)c2)c1 | null | [C-]#N.[Zn+2].[C-]#N | C(C)O | Miscellaneous | OtherReaction | 65fb274b9e40f0c73e43dcee64f9109c6f96aabdce8e472231611ca5fe7a8006 | 1057828eb7854b3bc292e1cd602b9bc4b8e879a7adfc7e5babd071ec27c3bf86 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:7](-[C;D1;H3:8])-[C:9]-[c:10]:[c:11]:[#7;a:12]>>[#7;a:12]:[c:11]:[c:10]-[C:9]-[NH;D2;+0:7]-[C;D1;H3:8].[N;D1;H0:13]#[C:14]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1 | 42 | [{"value": 42.0, "product": "Cl.CNCC=1C=C(N(C1)S(=O)(=O)C=1C=NC=C(C#N)C1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | A mixture of tert-butyl({1-[(5-bromopyridin-3-yl)sulfonyl]-5-phenyl-1H-pyrrol-3-yl}methyl)methylcarbamate (112 mg), zinc cyanide (50 mg) and N,N-dimethylformamide (4 mL) was degassed with argon gas. Tetrakis(triphenylphosphine)palladium (46 mg) was added, and the mixture was stirred at 100 degree C. for 1.5 hr. After c... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester.Ether.Boc | Nitrile.Secondary amine | c1ccncc1 | c1ccncc1 | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HBr | [C-]#N.[Zn+2].[C-]#N.C(C)O | null | 1.5 | CN(Cc1cc(-c2ccccc2)n(S(=O)(=O)c2cncc(Br)c2)c1)C(=O)OC(C)(C)C>[C-]#N.[Zn+2].[C-]#N.C(C)O>CNCc1cc(-c2ccccc2)n(S(=O)(=O)c2cncc(C#N)c2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2f6c77cd4b6048ea88e2d704e3a9cf14 | CN(Cc1cc(-c2ccccc2)n(S(=O)(=O)c2cncc(Br)c2)c1)C(=O)OC(C)(C)C.CO>>CNCc1cc(-c2ccccc2)n(S(=O)(=O)c2cncc(C(=O)OC)c2)c1 | C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)C1=CC=CC=C1)S(=O)(=O)C=1C=NC=C(C1)Br)=O.C(C)N(CC)CC.CO.C(C)(=O)OCC.Cl>>Cl.CNCC=1C=C(N(C1)S(=O)(=O)C=1C=NC=C(C(=O)OC)C1)C1=CC=CC=C1 | CC(C)(C)O[C:22]([N:2]([CH3:1])[CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[n:13]([S:14](=[O:15])(=[O:16])[c:17]2[cH:18][n:19][cH:20][c:21](Br)[cH:26]2)[cH:27]1)=[O:23].[OH:24][CH3:25]>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[n:13]([S:14](=[O:15])(=[O:16])[... | CN(Cc1cc(-c2ccccc2)n(S(=O)(=O)c2cncc(Br)c2)c1)C(=O)OC(C)(C)C.CO | CNCc1cc(-c2ccccc2)n(S(=O)(=O)c2cncc(C(=O)OC)c2)c1 | null | null | C(C)O | Acylation | OtherReaction | c4427b086282ae53c5a0f9986143e85739109e7cfddbb260d9d90eddd04f7db4 | 1e965b9ee81a202b4285c1c70b8e930c647d3362d016c130b7fafd76d8951b20 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.C-C(-C)(-C)-O-[C;H0;D3;+0:7](=[O;D1;H0:8])-[N;H0;D3;+0:9](-[C;D1;H3:10])-[C:11]-[c:12]:[c:13]:[#7;a:14].[C;D1;H3:15]-[OH;D1;+0:16]>>[#7;a:14]:[c:13]:[c:12]-[C:11]-[NH;D2;+0:9]-[C;D1;H3:10].[C;D1;H3:15]-[O;H0;D2;+0:16]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[c;H0;D3;+0:1]1:[c:... | 56 | [{"value": 56.0, "product": "Cl.CNCC=1C=C(N(C1)S(=O)(=O)C=1C=NC=C(C(=O)OC)C1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 12 | HOUR | A mixture of tert-butyl({1-[(5-bromopyridin-3-yl)sulfonyl]-5-phenyl-1H-pyrrol-3-yl}methyl)methylcarbamate (112 mg), dichloro[bis(triphenylphosphine)]palladium (28 mg), triethylamine (0.25 mL) and methanol (15 mL) was stirred under a carbon monoxide atmosphere (3 atm) at 100° C. for 12 hr. After cooling to room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester.Ether.Methanol.Boc | Ester.Secondary amine | c1ccncc1 | c1ccncc1 | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HBr | C(C)O | 100 | 12 | CN(Cc1cc(-c2ccccc2)n(S(=O)(=O)c2cncc(Br)c2)c1)C(=O)OC(C)(C)C.CO>C(C)O>CNCc1cc(-c2ccccc2)n(S(=O)(=O)c2cncc(C(=O)OC)c2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c44b1020d9024f7fa52adf28504de0b9 | CB(O)O.CN(Cc1cc(-c2ccccc2)n(S(=O)(=O)c2cncc(Br)c2)c1)C(=O)OC(C)(C)C>>CNCc1cc(-c2ccccc2)n(S(=O)(=O)c2cncc(C)c2)c1.Cl | C(O)([O-])=O.[Na+].BrC=1C=C(C=NC1)S(=O)(=O)N1C=C(C=C1C1=CC=CC=C1)CN(C(OC(C)(C)C)=O)C.CB(O)O.C([O-])([O-])=O.[K+].[K+].C(C)(=O)OCC.Cl>>Cl.Cl.CNCC1=CN(C(=C1)C1=CC=CC=C1)S(=O)(=O)C=1C=NC=C(C1)C | OB(O)[CH3:22].CC(C)(C)OC(=O)[N:2]([CH3:1])[CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[n:13]([S:14](=[O:15])(=[O:16])[c:17]2[cH:18][n:19][cH:20][c:21](Br)[cH:23]2)[cH:24]1>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[n:13]([S:14](=[O:15])(=[O:16])[c:17]2[cH:18... | CB(O)O.CN(Cc1cc(-c2ccccc2)n(S(=O)(=O)c2cncc(Br)c2)c1)C(=O)OC(C)(C)C | CNCc1cc(-c2ccccc2)n(S(=O)(=O)c2cncc(C)c2)c1.Cl | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O1CCOCC1.C(C)O | C-C Coupling | OtherReaction | 8fb62dff871de5a0e397efb0fec99d36e5d97aa8d62e29afcd4e40f0340ed4c9 | f8bc7d7af72f3dcb1d8785ac96c7aaf97c54842222d3f4332a40344844fc1d1c | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:7](-[C;D1;H3:8])-[C:9]-[c:10]:[c:11]:[#7;a:12].O-B(-O)-[CH3;D1;+0:13]>>[#7;a:12]:[c:11]:[c:10]-[C:9]-[NH;D2;+0:7]-[C;D1;H3:8].[CH3;D1;+0:13]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1 | 39 | [{"value": 39.0, "product": "Cl.Cl.CNCC1=CN(C(=C1)C1=CC=CC=C1)S(=O)(=O)C=1C=NC=C(C1)C", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 1 | DAY | Under an argon atmosphere, a mixture of tert-butyl ({1-[(5-bromopyridin-3-yl)sulfonyl]-5-phenyl-1H-pyrrol-3-yl}methyl)methylcarbamate (112 mg), methylboronic acid (18 mg), tetrakis(triphenylphosphine)palladium (23 mg), potassium carbonate (138 mg) and 1,4-dioxane (5 mL) was stirred at 80° C. for one day. The reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester.Ether.Boronic acid.Boc | Secondary amine | c1ccncc1 | c1ccncc1 | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1.C(C)O | 80 | 24 | CB(O)O.CN(Cc1cc(-c2ccccc2)n(S(=O)(=O)c2cncc(Br)c2)c1)C(=O)OC(C)(C)C>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1.C(C)O>CNCc1cc(-c2ccccc2)n(S(=O)(=O)c2cncc(C)c2)c1.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-923e1c30b1054c37bf5e8f9dfbbe1be9 | CN(Cc1cc(-c2ccc(S(C)(=O)=O)cc2)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C>>CNCc1cc(-c2ccc(S(C)(=O)=O)cc2)n(S(=O)(=O)c2cccnc2)c1.Cl | CN(C(OC(C)(C)C)=O)CC1=CN(C(=C1)C1=CC=C(C=C1)S(=O)(=O)C)S(=O)(=O)C=1C=NC=CC1.C(C)(=O)OCC.Cl>>Cl.Cl.CNCC1=CN(C(=C1)C1=CC=C(C=C1)S(=O)(=O)C)S(=O)(=O)C=1C=NC=CC1 | CC(C)(C)OC(=O)[N:2]([CH3:1])[CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([S:11]([CH3:12])(=[O:13])=[O:14])[cH:15][cH:16]2)[n:17]([S:18](=[O:19])(=[O:20])[c:21]2[cH:22][cH:23][cH:24][n:25][cH:26]2)[cH:27]1>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([S:11]([CH3:12])(=[O:13])=[O:14])[cH:15][cH:... | CN(Cc1cc(-c2ccc(S(C)(=O)=O)cc2)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | CNCc1cc(-c2ccc(S(C)(=O)=O)cc2)n(S(=O)(=O)c2cccnc2)c1.Cl | null | null | C(C)(=O)OCC | Miscellaneous | Boc amine deprotection | 43bd7dbe082e19ce552084e8c807e7cb13b754bbd3730fa221829c57747abf05 | c95e79e18f8ea11cf22745e0eab38cab98566b1b63e7d80ee200f4cb4f94f00c | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:3]-[NH;D2;+0:1]-[C;D1;H3:2] | 33 | [{"value": 33.0, "product": "Cl.Cl.CNCC1=CN(C(=C1)C1=CC=C(C=C1)S(=O)(=O)C)S(=O)(=O)C=1C=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a solution of tert-butyl methyl{[5-[4-(methylsulfonyl)phenyl]-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}carbamate (275 mg) in ethyl acetate (2 mL) was added a 4 mol/L hydrogen chloride-ethyl acetate solution (2 mL), and the mixture was stirred at room temperature for 4 hr. The precipitated crystals were collect... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | null | null | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HO- | C(C)(=O)OCC | null | 4 | CN(Cc1cc(-c2ccc(S(C)(=O)=O)cc2)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C>C(C)(=O)OCC>CNCc1cc(-c2ccc(S(C)(=O)=O)cc2)n(S(=O)(=O)c2cccnc2)c1.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-77eef838e6e44cf1bb88ed78cce2ccba | CN(Cc1cc(-c2ccccc2CO)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.O=C([O-])O>>CNCc1cc(-c2ccccc2CO)n(S(=O)(=O)c2cccnc2)c1.O=C(O)/C=C/C(=O)O | C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)C1=C(C=CC=C1)CO)S(=O)(=O)C=1C=NC=CC1)=O.FC(C(=O)O)(F)F.C(O)([O-])=O.[Na+]>>C(\C=C\C(=O)O)(=O)O.CNCC=1C=C(N(C1)S(=O)(=O)C=1C=NC=CC1)C1=C(C=CC=C1)CO | CC(C)(C)[O:33][C:31]([N:2]([CH3:1])[CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[CH2:13][OH:14])[n:15]([S:16](=[O:17])(=[O:18])[c:19]2[cH:20][cH:21][cH:22][n:23][cH:24]2)[cH:25]1)=[O:32].[O-][C:27](=[O:26])[OH:28]>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[CH2:13... | CN(Cc1cc(-c2ccccc2CO)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.O=C([O-])O | CNCc1cc(-c2ccccc2CO)n(S(=O)(=O)c2cccnc2)c1.O=C(O)/C=C/C(=O)O | null | null | null | C-C Coupling | OtherReaction | 359b5f4f5a3fcf33ed7479cd94b28e63af8eeeded4d3f49f8b911a64e24e12ba | 83d77212ee8fec248940498d330551265ab62ee32da500d145814cea7313a179 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[N;H0;D3;+0:4](-[C;D1;H3:5])-[C:6]-[c:7]:[c:8]:[#7;a:9].[O-]-[C;H0;D3;+0:10](=[O;D1;H0:11])-[O;D1;H1:12]>>[#7;a:9]:[c:8]:[c:7]-[C:6]-[NH;D2;+0:4]-[C;D1;H3:5].[O;D1;H0:11]=[C;H0;D3;+0:10](-[O;D1;H1:12])/[C:13]=[C:14]/[C;H0;D3;+0:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | 1 | HOUR | tert-Butyl({5-[2-(hydroxymethyl)phenyl]-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl}methyl)methylcarbamate (132 mg) was dissolved in trifluoroacetic acid (1 mL), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was basified with a saturated aqueous sodium hydrogencarbonate solution and extract... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbonic Acid.Ether.Boc | Carboxylic acid.Carboxylic acid.Secondary amine | null | null | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HO- | null | null | 1 | CN(Cc1cc(-c2ccccc2CO)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.O=C([O-])O>>CNCc1cc(-c2ccccc2CO)n(S(=O)(=O)c2cccnc2)c1.O=C(O)/C=C/C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d8bcd2ae641f489f9c9f5f4837682ee6 | Cc1cscc1-c1cc(CN(C)C(=O)OC(C)(C)C)cn1S(=O)(=O)c1cccnc1.O=C([O-])O>>CNCc1cc(-c2cscc2C)n(S(=O)(=O)c2cccnc2)c1.O=C(O)/C=C/C(=O)O | C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)C1=CSC=C1C)S(=O)(=O)C=1C=NC=CC1)=O.FC(C(=O)O)(F)F.C(O)([O-])=O.[Na+]>>C(\C=C\C(=O)O)(=O)O.CNCC1=CN(C(=C1)C1=CSC=C1C)S(=O)(=O)C=1C=NC=CC1 | CC(C)(C)[O:31][C:29]([N:2]([CH3:1])[CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][s:9][cH:10][c:11]2[CH3:12])[n:13]([S:14](=[O:15])(=[O:16])[c:17]2[cH:18][cH:19][cH:20][n:21][cH:22]2)[cH:23]1)=[O:30].[O-][C:25](=[O:24])[OH:26]>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][s:9][cH:10][c:11]2[CH3:12])[n:13]([S:14](=[O:15]... | Cc1cscc1-c1cc(CN(C)C(=O)OC(C)(C)C)cn1S(=O)(=O)c1cccnc1.O=C([O-])O | CNCc1cc(-c2cscc2C)n(S(=O)(=O)c2cccnc2)c1.O=C(O)/C=C/C(=O)O | null | null | null | C-C Coupling | OtherReaction | 359b5f4f5a3fcf33ed7479cd94b28e63af8eeeded4d3f49f8b911a64e24e12ba | 83d77212ee8fec248940498d330551265ab62ee32da500d145814cea7313a179 | O=S(=O)(c1cccnc1)n1cccc1-c1ccsc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[N;H0;D3;+0:4](-[C;D1;H3:5])-[C:6]-[c:7]:[c:8]:[#7;a:9].[O-]-[C;H0;D3;+0:10](=[O;D1;H0:11])-[O;D1;H1:12]>>[#7;a:9]:[c:8]:[c:7]-[C:6]-[NH;D2;+0:4]-[C;D1;H3:5].[O;D1;H0:11]=[C;H0;D3;+0:10](-[O;D1;H1:12])/[C:13]=[C:14]/[C;H0;D3;+0:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | 30 | MINUTE | By a similar reaction as in Example 59 and using tert-butyl {[5-(4-methyl-3-thienyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (943 mg), the title compound was obtained as colorless crystals (yield 553 mg, 57%). More specifically, tert-butyl{[5-(4-methyl-3-thienyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrro... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbonic Acid.Ether.Boc | Carboxylic acid.Carboxylic acid.Secondary amine | null | null | c1cc[nH]c1.c1ccsc1.c1ccncc1 | HO- | null | null | 0.5 | Cc1cscc1-c1cc(CN(C)C(=O)OC(C)(C)C)cn1S(=O)(=O)c1cccnc1.O=C([O-])O>>CNCc1cc(-c2cscc2C)n(S(=O)(=O)c2cccnc2)c1.O=C(O)/C=C/C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f9dd6d764c5a4a88b4ccfaa1a6667fb3 | CCOC(C)=O.CN(Cc1cc(-c2ccc(C#N)cc2)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.O=C([O-])O>>CNCc1cc(-c2ccc(C#N)cc2)n(S(=O)(=O)c2cccnc2)c1.O=C(O)/C=C/C(=O)O | C(O)([O-])=O.[Na+].C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)C1=CC=C(C=C1)C#N)S(=O)(=O)C=1C=NC=CC1)=O.C(C)(=O)OCC.Cl>>C(\C=C\C(=O)O)(=O)O.CNCC=1C=C(N(C1)S(=O)(=O)C=1C=NC=CC1)C1=CC=C(C#N)C=C1 | CCO[C:29](=O)[CH3:30].CC(C)(C)[O:33][C:31]([N:2]([CH3:1])[CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11]#[N:12])[cH:13][cH:14]2)[n:15]([S:16](=[O:17])(=[O:18])[c:19]2[cH:20][cH:21][cH:22][n:23][cH:24]2)[cH:25]1)=[O:32].[O-][C:27](=[O:26])[OH:28]>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]... | CCOC(C)=O.CN(Cc1cc(-c2ccc(C#N)cc2)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.O=C([O-])O | CNCc1cc(-c2ccc(C#N)cc2)n(S(=O)(=O)c2cccnc2)c1.O=C(O)/C=C/C(=O)O | null | null | C(C)(=O)OCC | C-C Coupling | OtherReaction | b1f1bf4555efbcd39304f367cad38877042f23289af2dc03ffc0fb8c5c4fcb56 | 49143ed6936a5663738db68234634880fb840e0856ca233e09905efff6240e90 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[N;H0;D3;+0:4](-[C;D1;H3:5])-[C:6]-[c:7]:[c:8]:[#7;a:9].C-C-O-[C;H0;D3;+0:10](=O)-[CH3;D1;+0:11].[O-]-[C;H0;D3;+0:12](=[O;D1;H0:13])-[O;D1;H1:14]>>[#7;a:9]:[c:8]:[c:7]-[C:6]-[NH;D2;+0:4]-[C;D1;H3:5].[O;D1;H0:13]=[C;H0;D3;+0:12](-[O;D1;H1:14])/[CH;D2;+0:10]=[CH;D2;... | null | [] | null | null | 3 | HOUR | To a solution (2 mL) of tert-butyl{[5-(4-cyanophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (382 mg) in ethyl acetate was added a 4 mol/L hydrogen chloride-ethyl acetate solution (3 mL) at room temperature. The mixture was stirred for 3 hr, and basified with a saturated aqueous sodium hydrogenc... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbonic Acid.Ester.Ether.Boc | Carboxylic acid.Carboxylic acid.Secondary amine | null | null | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HO- | C(C)(=O)OCC | null | 3 | CCOC(C)=O.CN(Cc1cc(-c2ccc(C#N)cc2)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.O=C([O-])O>C(C)(=O)OCC>CNCc1cc(-c2ccc(C#N)cc2)n(S(=O)(=O)c2cccnc2)c1.O=C(O)/C=C/C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-60714ff2c48f45849d7e54e9e5ae7f35 | CCO.CCOC(C)=O.COc1ccc(F)c(-c2cc(CN(C)C(=O)OC(C)(C)C)cn2S(=O)(=O)c2cccnc2)c1>>CNCc1cc(-c2cc(OC)ccc2F)n(S(=O)(=O)c2cccnc2)c1.O=C(O)/C=C/C(=O)O | FC1=C(C=C(C=C1)OC)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C.C(C)O.C(C)(=O)OCC.Cl>>C(\C=C\C(=O)O)(=O)O.FC1=C(C=C(C=C1)OC)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CNC | OC[CH3:31].CC[O:29][C:28](=[O:27])[CH3:30].CC(C)(C)[O:34][C:32]([N:2]([CH3:1])[CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][c:9]([O:10][CH3:11])[cH:12][cH:13][c:14]2[F:15])[n:16]([S:17](=[O:18])(=[O:19])[c:20]2[cH:21][cH:22][cH:23][n:24][cH:25]2)[cH:26]1)=[O:33]>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][c:9]([O:10]... | CCO.CCOC(C)=O.COc1ccc(F)c(-c2cc(CN(C)C(=O)OC(C)(C)C)cn2S(=O)(=O)c2cccnc2)c1 | CNCc1cc(-c2cc(OC)ccc2F)n(S(=O)(=O)c2cccnc2)c1.O=C(O)/C=C/C(=O)O | null | null | null | C-C Coupling | OtherReaction | b2772822100ec83589a5419602251f63691b562eccefe71bbfb3dd5d43ad2727 | 1e2a39df58a861e56d93cf7fb5c19acd7b0143d6fcd8ce21a82118549c442685 | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[N;H0;D3;+0:4](-[C;D1;H3:5])-[C:6]-[c:7]:[c:8]:[#7;a:9].C-C-[O;H0;D2;+0:10]-[C:11](-[CH3;D1;+0:12])=[O;D1;H0:13].O-C-[CH3;D1;+0:14]>>[#7;a:9]:[c:8]:[c:7]-[C:6]-[NH;D2;+0:4]-[C;D1;H3:5].[O;D1;H0:13]=[C:11](-[OH;D1;+0:10])/[CH;D2;+0:12]=[CH;D2;+0:14]/[C;H0;D3;+0:2](... | 78 | [{"value": 78.0, "product": "C(\\C=C\\C(=O)O)(=O)O.FC1=C(C=C(C=C1)OC)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CNC", "details": "PERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 30 | MINUTE | tert-Butyl {[5-(2-fluoro-5-methoxyphenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (475 mg) was dissolved in ethanol (10 mL), a 4 mol/L hydrogen chloride-ethyl acetate solution (2 mL) was added and the mixture was stirred at 70° C. for 30 min. The reaction mixture was concentrated under reduced pr... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether.Primary alcohol.Boc | Carboxylic acid.Carboxylic acid.Secondary amine | null | null | c1cc[nH]c1.c1ccccc1.c1ccncc1 | HO- | null | 70 | 0.5 | CCO.CCOC(C)=O.COc1ccc(F)c(-c2cc(CN(C)C(=O)OC(C)(C)C)cn2S(=O)(=O)c2cccnc2)c1>>CNCc1cc(-c2cc(OC)ccc2F)n(S(=O)(=O)c2cccnc2)c1.O=C(O)/C=C/C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ce6974ad2ed04bea915957b9e9596a4a | CCOC(C)=O.CCOC(C)=O.CN(Cc1cc(-c2cccnc2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C>>CNCc1cc(-c2cccnc2F)n(S(=O)(=O)c2cccnc2)c1.O=C(O)/C=C/C(=O)O | C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)C=1C(=NC=CC1)F)S(=O)(=O)C=1C=NC=CC1)=O.C(C)(=O)OCC.Cl.C(C)(=O)OCC>>C(\C=C\C(=O)O)(=O)O.FC1=NC=CC=C1C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CNC | CCOC(=O)[CH3:29].CC[O:27][C:26](=[O:25])[CH3:28].CC(C)(C)[O:32][C:30]([N:2]([CH3:1])[CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][n:11][c:12]2[F:13])[n:14]([S:15](=[O:16])(=[O:17])[c:18]2[cH:19][cH:20][cH:21][n:22][cH:23]2)[cH:24]1)=[O:31]>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][n:11][c:... | CCOC(C)=O.CCOC(C)=O.CN(Cc1cc(-c2cccnc2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | CNCc1cc(-c2cccnc2F)n(S(=O)(=O)c2cccnc2)c1.O=C(O)/C=C/C(=O)O | null | null | CO | C-C Coupling | OtherReaction | 016971eedbd9e416d15e57cb8dd0c618d5e7f7ea7beeca021ce99a471d298a85 | bfaa49588aee2f1c98925b568e27805a4d35222fd79509d26ab2fd71eb963c44 | O=S(=O)(c1cccnc1)n1cccc1-c1cccnc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[N;H0;D3;+0:4](-[C;D1;H3:5])-[C:6]-[c:7]:[c:8]:[#7;a:9].C-C-O-C(=O)-[CH3;D1;+0:10].C-C-[O;H0;D2;+0:11]-[C:12](-[CH3;D1;+0:13])=[O;D1;H0:14]>>[#7;a:9]:[c:8]:[c:7]-[C:6]-[NH;D2;+0:4]-[C;D1;H3:5].[O;D1;H0:14]=[C:12](-[OH;D1;+0:11])/[CH;D2;+0:13]=[CH;D2;+0:10]/[C;H0;D... | null | [] | null | null | 5 | HOUR | To a solution of tert-butyl{[5-(2-fluoropyridin-3-yl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (2.48 g) in ethyl acetate (10 mL) and methanol (10 mL) was added a 4 mol/L hydrogen chloride-ethyl acetate solution (20 mL) at room temperature. After stirring for 5 hr, the mixture was concentrated unde... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ester.Ether.Boc | Carboxylic acid.Carboxylic acid.Secondary amine | null | null | c1cc[nH]c1.c1ccncc1.c1ccncc1 | HO- | CO | null | 5 | CCOC(C)=O.CCOC(C)=O.CN(Cc1cc(-c2cccnc2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C>CO>CNCc1cc(-c2cccnc2F)n(S(=O)(=O)c2cccnc2)c1.O=C(O)/C=C/C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c34adda1448a40d4936e9f7ffc4e51b8 | CCOC(C)=O.CN(Cc1cc(-c2ccncc2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.CO>>CNCc1cc(-c2ccncc2F)n(S(=O)(=O)c2cccnc2)c1.O=C(O)/C=C/C(=O)O | C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)C1=C(C=NC=C1)F)S(=O)(=O)C=1C=NC=CC1)=O.CO.C(C)(=O)OCC.Cl>>C(\C=C\C(=O)O)(=O)O.FC=1C=NC=CC1C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CNC | CC[O:27][C:26](=[O:25])[CH3:28].CC(C)(C)[O:32][C:30]([N:2]([CH3:1])[CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][n:10][cH:11][c:12]2[F:13])[n:14]([S:15](=[O:16])(=[O:17])[c:18]2[cH:19][cH:20][cH:21][n:22][cH:23]2)[cH:24]1)=[O:31].O[CH3:29]>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][n:10][cH:11][c:12]2[F:... | CCOC(C)=O.CN(Cc1cc(-c2ccncc2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.CO | CNCc1cc(-c2ccncc2F)n(S(=O)(=O)c2cccnc2)c1.O=C(O)/C=C/C(=O)O | null | null | null | C-C Coupling | OtherReaction | e4e5caaba6ab23b1932f6e4327b97b3251aa2cc7e076a046177804f7856091a5 | db3ed21b2158edff973626241b7526d211895d664e0ff80960cdd9b9ab6a2c6a | O=S(=O)(c1cccnc1)n1cccc1-c1ccncc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[N;H0;D3;+0:4](-[C;D1;H3:5])-[C:6]-[c:7]:[c:8]:[#7;a:9].C-C-[O;H0;D2;+0:10]-[C:11](-[CH3;D1;+0:12])=[O;D1;H0:13].O-[CH3;D1;+0:14]>>[#7;a:9]:[c:8]:[c:7]-[C:6]-[NH;D2;+0:4]-[C;D1;H3:5].[O;D1;H0:13]=[C:11](-[OH;D1;+0:10])/[CH;D2;+0:12]=[CH;D2;+0:14]/[C;H0;D3;+0:2](=[... | 72 | [{"value": 72.0, "product": "C(\\C=C\\C(=O)O)(=O)O.FC=1C=NC=CC1C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CNC", "details": "PERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 30 | MINUTE | tert-Butyl{[5-(3-fluoropyridin-4-yl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (60 mg) was dissolved in methanol (5 mL), a 4 mol/L hydrogen chloride-ethyl acetate solution (1.5 mL) was added and the mixture was stirred at 70° C. for 30 min. The reaction mixture was concentrated under reduced pressu... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether.Methanol.Boc | Carboxylic acid.Carboxylic acid.Secondary amine | null | null | c1cc[nH]c1.c1ccncc1.c1ccncc1 | HO- | null | 70 | 0.5 | CCOC(C)=O.CN(Cc1cc(-c2ccncc2F)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C.CO>>CNCc1cc(-c2ccncc2F)n(S(=O)(=O)c2cccnc2)c1.O=C(O)/C=C/C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4856e5d0e8274874b5bc5064c680b232 | CCO.CCOC(C)=O.CN(Cc1cc(-c2cccnc2Cl)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C>>CNCc1cc(-c2cccnc2Cl)n(S(=O)(=O)c2cccnc2)c1.O=C(O)/C=C/C(=O)O | ClC1=NC=CC=C1C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C.C(C)O.C(C)(=O)OCC.Cl>>C(\C=C\C(=O)O)(=O)O.ClC1=NC=CC=C1C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CNC | OC[CH3:29].CC[O:27][C:26](=[O:25])[CH3:28].CC(C)(C)[O:32][C:30]([N:2]([CH3:1])[CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][n:11][c:12]2[Cl:13])[n:14]([S:15](=[O:16])(=[O:17])[c:18]2[cH:19][cH:20][cH:21][n:22][cH:23]2)[cH:24]1)=[O:31]>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][n:11][c:12]2[... | CCO.CCOC(C)=O.CN(Cc1cc(-c2cccnc2Cl)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | CNCc1cc(-c2cccnc2Cl)n(S(=O)(=O)c2cccnc2)c1.O=C(O)/C=C/C(=O)O | null | null | null | C-C Coupling | OtherReaction | b2772822100ec83589a5419602251f63691b562eccefe71bbfb3dd5d43ad2727 | 1e2a39df58a861e56d93cf7fb5c19acd7b0143d6fcd8ce21a82118549c442685 | O=S(=O)(c1cccnc1)n1cccc1-c1cccnc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[N;H0;D3;+0:4](-[C;D1;H3:5])-[C:6]-[c:7]:[c:8]:[#7;a:9].C-C-[O;H0;D2;+0:10]-[C:11](-[CH3;D1;+0:12])=[O;D1;H0:13].O-C-[CH3;D1;+0:14]>>[#7;a:9]:[c:8]:[c:7]-[C:6]-[NH;D2;+0:4]-[C;D1;H3:5].[O;D1;H0:13]=[C:11](-[OH;D1;+0:10])/[CH;D2;+0:12]=[CH;D2;+0:14]/[C;H0;D3;+0:2](... | 68 | [{"value": 68.0, "product": "C(\\C=C\\C(=O)O)(=O)O.ClC1=NC=CC=C1C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CNC", "details": "PERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 30 | MINUTE | tert-Butyl {[5-(2-chloropyridin-3-yl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (280 mg) was dissolved in ethanol (10 mL), a 4 mol/L hydrogen chloride-ethyl acetate solution (2 mL) was added and the mixture was stirred at 70° C. for 30 min. The reaction mixture was concentrated under reduced pressu... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether.Primary alcohol.Boc | Carboxylic acid.Carboxylic acid.Secondary amine | null | null | c1cc[nH]c1.c1ccncc1.c1ccncc1 | HO- | null | 70 | 0.5 | CCO.CCOC(C)=O.CN(Cc1cc(-c2cccnc2Cl)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C>>CNCc1cc(-c2cccnc2Cl)n(S(=O)(=O)c2cccnc2)c1.O=C(O)/C=C/C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-41b9bf854afd41eca4a08bed58840e92 | CN(Cc1cc(-c2ccc(-c3ccc(Cl)nc3)nc2)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C>>CNCc1cc(-c2ccc(-c3ccc(Cl)nc3)nc2)n(S(=O)(=O)c2cccnc2)c1 | C(C)(C)(C)OC(N(C)CC1=CN(C(=C1)C=1C=CC(=NC1)C=1C=NC(=CC1)Cl)S(=O)(=O)C=1C=NC=CC1)=O.C(C)(=O)OCC.Cl>>ClC1=CC=C(C=N1)C1=NC=C(C=C1)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CNC | CC(C)(C)OC(=O)[N:2]([CH3:1])[CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][c:14]([Cl:15])[n:16][cH:17]3)[n:18][cH:19]2)[n:20]([S:21](=[O:22])(=[O:23])[c:24]2[cH:25][cH:26][cH:27][n:28][cH:29]2)[cH:30]1>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][c:1... | CN(Cc1cc(-c2ccc(-c3ccc(Cl)nc3)nc2)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C | CNCc1cc(-c2ccc(-c3ccc(Cl)nc3)nc2)n(S(=O)(=O)c2cccnc2)c1 | null | null | C(C)O | Reduction | Boc amine deprotection | bbda4640db5f48af4538caded12fdadd56eacd6d4e5f7aefe46282d665df167e | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=S(=O)(c1cccnc1)n1cccc1-c1ccc(-c2cccnc2)nc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:3]-[NH;D2;+0:1]-[C;D1;H3:2] | null | [] | 70 | CELSIUS | 30 | MINUTE | tert-Butyl{[5-(6′-chloro-2,3′-bipyridin-5-yl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (100 mg) was dissolved in ethanol (8 mL), a 4 mol/L hydrogen chloride-ethyl acetate solution (2 mL) was added and the mixture was stirred at 70° C. for 30 min. The reaction mixture was concentrated under reduced... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | null | null | c1cc[nH]c1.c1ccncc1.c1ccncc1.c1ccncc1 | HO- | C(C)O | 70 | 0.5 | CN(Cc1cc(-c2ccc(-c3ccc(Cl)nc3)nc2)n(S(=O)(=O)c2cccnc2)c1)C(=O)OC(C)(C)C>C(C)O>CNCc1cc(-c2ccc(-c3ccc(Cl)nc3)nc2)n(S(=O)(=O)c2cccnc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d4e4e34ad55c4072b257a70b618af76d | CCOC(C)=O.COc1cccc(-c2cc(CN(C)C(=O)OC(C)(C)C)cn2S(=O)(=O)c2cccnc2)c1F>>CNCc1cc(-c2cccc(OC)c2F)n(S(=O)(=O)c2cccnc2)c1.O=C(O)/C=C/C(=O)O | FC1=C(C=CC=C1OC)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C.CO.C(C)(=O)OCC.Cl>>C(\C=C\C(=O)O)(=O)O.FC1=C(C=CC=C1OC)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CNC | C([O:29][C:28](=[O:27])[CH3:30])[CH3:31].CC(C)(C)[O:34][C:32]([N:2]([CH3:1])[CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][c:11]([O:12][CH3:13])[c:14]2[F:15])[n:16]([S:17](=[O:18])(=[O:19])[c:20]2[cH:21][cH:22][cH:23][n:24][cH:25]2)[cH:26]1)=[O:33]>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][... | CCOC(C)=O.COc1cccc(-c2cc(CN(C)C(=O)OC(C)(C)C)cn2S(=O)(=O)c2cccnc2)c1F | CNCc1cc(-c2cccc(OC)c2F)n(S(=O)(=O)c2cccnc2)c1.O=C(O)/C=C/C(=O)O | null | null | null | C-C Coupling | OtherReaction | a3d6e908fa11301e95929180d6e7776b7e915d4799420ce671bd568439f40061 | ec8427350d5c3d6027e2dff7ad15c326b11d7a1b23060029c3c2227580232ddc | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[N;H0;D3;+0:4](-[C;D1;H3:5])-[C:6]-[c:7]:[c:8]:[#7;a:9].[CH3;D1;+0:10]-[C:11](=[O;D1;H0:12])-[O;H0;D2;+0:13]-C-[CH3;D1;+0:14]>>[#7;a:9]:[c:8]:[c:7]-[C:6]-[NH;D2;+0:4]-[C;D1;H3:5].[O;D1;H0:12]=[C:11](-[OH;D1;+0:13])/[CH;D2;+0:10]=[CH;D2;+0:14]/[C;H0;D3;+0:2](=[O;D1... | 63 | [{"value": 63.0, "product": "C(\\C=C\\C(=O)O)(=O)O.FC1=C(C=CC=C1OC)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CNC", "details": "PERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 20 | MINUTE | tert-Butyl {[5-(2-fluoro-3-methoxyphenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (475 mg) was dissolved in methanol (20 mL), a 4 mol/L hydrogen chloride-ethyl acetate solution (2 mL) was added and the mixture was stirred at 70° C. for 20 min. The reaction mixture was concentrated under reduced p... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether.Boc | Carboxylic acid.Carboxylic acid.Secondary amine | null | null | c1cc[nH]c1.c1ccccc1.c1ccncc1 | Other | null | 70 | 0.333333 | CCOC(C)=O.COc1cccc(-c2cc(CN(C)C(=O)OC(C)(C)C)cn2S(=O)(=O)c2cccnc2)c1F>>CNCc1cc(-c2cccc(OC)c2F)n(S(=O)(=O)c2cccnc2)c1.O=C(O)/C=C/C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b83f256db5e847eeb9a99bc63b0ddc29 | CCOC(C)=O.COc1cccc(F)c1-c1cc(CN(C)C(=O)OC(C)(C)C)cn1S(=O)(=O)c1cccnc1>>CNCc1cc(-c2c(F)cccc2OC)n(S(=O)(=O)c2cccnc2)c1.O=C(O)/C=C/C(=O)O | FC1=C(C(=CC=C1)OC)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CN(C(OC(C)(C)C)=O)C.CO.C(C)(=O)OCC.Cl>>C(\C=C\C(=O)O)(=O)O.FC1=C(C(=CC=C1)OC)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CNC | C([O:29][C:28](=[O:27])[CH3:30])[CH3:31].CC(C)(C)[O:34][C:32]([N:2]([CH3:1])[CH2:3][c:4]1[cH:5][c:6](-[c:7]2[c:8]([F:9])[cH:10][cH:11][cH:12][c:13]2[O:14][CH3:15])[n:16]([S:17](=[O:18])(=[O:19])[c:20]2[cH:21][cH:22][cH:23][n:24][cH:25]2)[cH:26]1)=[O:33]>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[c:8]([F:9])[cH:10][... | CCOC(C)=O.COc1cccc(F)c1-c1cc(CN(C)C(=O)OC(C)(C)C)cn1S(=O)(=O)c1cccnc1 | CNCc1cc(-c2c(F)cccc2OC)n(S(=O)(=O)c2cccnc2)c1.O=C(O)/C=C/C(=O)O | null | null | null | C-C Coupling | OtherReaction | a3d6e908fa11301e95929180d6e7776b7e915d4799420ce671bd568439f40061 | ec8427350d5c3d6027e2dff7ad15c326b11d7a1b23060029c3c2227580232ddc | O=S(=O)(c1cccnc1)n1cccc1-c1ccccc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[N;H0;D3;+0:4](-[C;D1;H3:5])-[C:6]-[c:7]:[c:8]:[#7;a:9].[CH3;D1;+0:10]-[C:11](=[O;D1;H0:12])-[O;H0;D2;+0:13]-C-[CH3;D1;+0:14]>>[#7;a:9]:[c:8]:[c:7]-[C:6]-[NH;D2;+0:4]-[C;D1;H3:5].[O;D1;H0:12]=[C:11](-[OH;D1;+0:13])/[CH;D2;+0:10]=[CH;D2;+0:14]/[C;H0;D3;+0:2](=[O;D1... | 51 | [{"value": 51.0, "product": "C(\\C=C\\C(=O)O)(=O)O.FC1=C(C(=CC=C1)OC)C1=CC(=CN1S(=O)(=O)C=1C=NC=CC1)CNC", "details": "PERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 20 | MINUTE | tert-Butyl {[5-(2-fluoro-6-methoxyphenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (100 mg) was dissolved in methanol (20 mL), a 4 mol/L hydrogen chloride-ethyl acetate solution (2 mL) was added and the mixture was stirred at 70° C. for 20 min. The reaction mixture was concentrated under reduced p... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether.Boc | Carboxylic acid.Carboxylic acid.Secondary amine | null | null | c1cc[nH]c1.c1ccccc1.c1ccncc1 | Other | null | 70 | 0.333333 | CCOC(C)=O.COc1cccc(F)c1-c1cc(CN(C)C(=O)OC(C)(C)C)cn1S(=O)(=O)c1cccnc1>>CNCc1cc(-c2c(F)cccc2OC)n(S(=O)(=O)c2cccnc2)c1.O=C(O)/C=C/C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9a8710ed5398494381e381d5acd99f98 | CCOC(C)=O.CO.Cc1ccncc1-c1cc(CN(C)C(=O)OC(C)(C)C)cn1S(=O)(=O)c1cccnc1>>CNCc1cc(-c2cnccc2C)n(S(=O)(=O)c2cccnc2)c1.O=C(O)/C=C/C(=O)O | CN(C(OC(C)(C)C)=O)CC1=CN(C(=C1)C=1C=NC=CC1C)S(=O)(=O)C=1C=NC=CC1.CO.C(C)(=O)OCC.Cl>>C(\C=C\C(=O)O)(=O)O.CNCC1=CN(C(=C1)C=1C=NC=CC1C)S(=O)(=O)C=1C=NC=CC1 | CC[O:27][C:26](=[O:25])[CH3:28].O[CH3:29].CC(C)(C)[O:32][C:30]([N:2]([CH3:1])[CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][n:9][cH:10][cH:11][c:12]2[CH3:13])[n:14]([S:15](=[O:16])(=[O:17])[c:18]2[cH:19][cH:20][cH:21][n:22][cH:23]2)[cH:24]1)=[O:31]>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][n:9][cH:10][cH:11][c:12]2[... | CCOC(C)=O.CO.Cc1ccncc1-c1cc(CN(C)C(=O)OC(C)(C)C)cn1S(=O)(=O)c1cccnc1 | CNCc1cc(-c2cnccc2C)n(S(=O)(=O)c2cccnc2)c1.O=C(O)/C=C/C(=O)O | null | null | null | C-C Coupling | OtherReaction | e4e5caaba6ab23b1932f6e4327b97b3251aa2cc7e076a046177804f7856091a5 | db3ed21b2158edff973626241b7526d211895d664e0ff80960cdd9b9ab6a2c6a | O=S(=O)(c1cccnc1)n1cccc1-c1cccnc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[N;H0;D3;+0:4](-[C;D1;H3:5])-[C:6]-[c:7]:[c:8]:[#7;a:9].C-C-[O;H0;D2;+0:10]-[C:11](-[CH3;D1;+0:12])=[O;D1;H0:13].O-[CH3;D1;+0:14]>>[#7;a:9]:[c:8]:[c:7]-[C:6]-[NH;D2;+0:4]-[C;D1;H3:5].[O;D1;H0:13]=[C:11](-[OH;D1;+0:10])/[CH;D2;+0:12]=[CH;D2;+0:14]/[C;H0;D3;+0:2](=[... | null | [] | 70 | CELSIUS | 20 | MINUTE | tert-Butyl methyl{[5-(4-methylpyridin-3-yl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}carbamate (230 mg) was dissolved in methanol (20 mL), a 4 mol/L hydrogen chloride-ethyl acetate solution (2 mL) was added and the mixture was stirred at 70° C. for 20 min. The reaction mixture was concentrated under reduced press... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether.Methanol.Boc | Carboxylic acid.Carboxylic acid.Secondary amine | null | null | c1cc[nH]c1.c1ccncc1.c1ccncc1 | HO- | null | 70 | 0.333333 | CCOC(C)=O.CO.Cc1ccncc1-c1cc(CN(C)C(=O)OC(C)(C)C)cn1S(=O)(=O)c1cccnc1>>CNCc1cc(-c2cnccc2C)n(S(=O)(=O)c2cccnc2)c1.O=C(O)/C=C/C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5e08db24b1874000975d56a18a10f343 | Cc1ccc(S(=O)(=O)n2cc(CN(C)C(=O)OC(C)(C)C)cc2-c2cccnc2F)cn1>>CNCc1cc(-c2cccnc2F)n(S(=O)(=O)c2ccc(C)nc2)c1 | FC1=NC=CC=C1C1=CC(=CN1S(=O)(=O)C=1C=NC(=CC1)C)CN(C(OC(C)(C)C)=O)C.C(C)(=O)OCC.Cl>>FC1=NC=CC=C1C1=CC(=CN1S(=O)(=O)C=1C=NC(=CC1)C)CNC | CC(C)(C)OC(=O)[N:2]([CH3:1])[CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][n:11][c:12]2[F:13])[n:14]([S:15](=[O:16])(=[O:17])[c:18]2[cH:19][cH:20][c:21]([CH3:22])[n:23][cH:24]2)[cH:25]1>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][n:11][c:12]2[F:13])[n:14]([S:15](=[O:16])(=[O:17])[c:18]2[cH:19... | Cc1ccc(S(=O)(=O)n2cc(CN(C)C(=O)OC(C)(C)C)cc2-c2cccnc2F)cn1 | CNCc1cc(-c2cccnc2F)n(S(=O)(=O)c2ccc(C)nc2)c1 | null | null | C(C)O | Reduction | Boc amine deprotection | bbda4640db5f48af4538caded12fdadd56eacd6d4e5f7aefe46282d665df167e | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=S(=O)(c1cccnc1)n1cccc1-c1cccnc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:3]-[NH;D2;+0:1]-[C;D1;H3:2] | null | [] | null | null | 2 | HOUR | To a solution of tert-butyl ({5-(2-fluoropyridin-3-yl)-1-[(6-methylpyridin-3-yl)sulfonyl]-1H-pyrrol-3-yl}methyl)methylcarbamate (86 mg) in ethanol (2 mL) was added a 4 mol/L hydrogen chloride-ethyl acetate solution (2 mL) at room temperature. The mixture was stirred for 2 hr, and concentrated under reduced pressure. Th... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | null | null | c1cc[nH]c1.c1ccncc1.c1ccncc1 | HO- | C(C)O | null | 2 | Cc1ccc(S(=O)(=O)n2cc(CN(C)C(=O)OC(C)(C)C)cc2-c2cccnc2F)cn1>C(C)O>CNCc1cc(-c2cccnc2F)n(S(=O)(=O)c2ccc(C)nc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c8cf715d635b48be87c38449243a596a | O=C([O-])CC[C@H](NC(=O)CCS)C(=O)[O-].O=[As]c1ccc(NC(=O)CSCCC(=O)N[C@@H](CC(=O)O)C(=O)O)cc1>>O=[As]c1ccc(NC(=O)CSCCC(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1 | [As](=O)C1=CC=C(C=C1)NC(=O)CSCCC(=O)N[C@@H](CC(=O)O)C(=O)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.SCCC(=O)N[C@@H](CCC(=O)[O-])C(=O)[O-].[Na+].[Na+].C([O-])(O)=O>>[As](=O)C1=CC=C(C=C1)NC(=O)CSCCC(=O)N[C@@H](CCC(=O)O)C(=O)O | O=C(CCS)N[C@H](C(=O)[O-])[CH2:18][CH2:19][C:20](=[O:21])[O-:22].O=C(O)C[C@H:17]([NH:16][C:14]([CH2:13][CH2:12][S:11][CH2:10][C:8]([NH:7][c:6]1[cH:5][cH:4][c:3]([As:2]=[O:1])[cH:27][cH:26]1)=[O:9])=[O:15])[C:23](=[O:24])[OH:25]>>[O:1]=[As:2][c:3]1[cH:4][cH:5][c:6]([NH:7][C:8](=[O:9])[CH2:10][S:11][CH2:12][CH2:13][C:14](... | O=C([O-])CC[C@H](NC(=O)CCS)C(=O)[O-].O=[As]c1ccc(NC(=O)CSCCC(=O)N[C@@H](CC(=O)O)C(=O)O)cc1 | O=[As]c1ccc(NC(=O)CSCCC(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1 | null | null | CS(=O)C | C-C Coupling | OtherReaction | 27df6118213d0a186385ca2c07812d6bde0c77fb447f8e5ba884d3fa9fc2c7c8 | 4a0ad09b2376324fd5f347eb80435967738ca7e434f5634c3eca7157b018355a | c1ccccc1 | O-C(=O)-C-[C@H;D3;+0:1](-[#7:2]-[C:3](-[C:4])=[O;D1;H0:5])-[C:6](=[O;D1;H0:7])-[O;D1;H1:8].O=C(-C-C-S)-N-[C@H](-[CH2;D2;+0:9]-[C:10]-[C:11](-[O-;H0;D1:12])=[O;D1;H0:13])-C(=O)-[O-]>>[C:4]-[C:3](=[O;D1;H0:5])-[#7:2]-[C@@H;D3;+0:1](-[CH2;D2;+0:9]-[C:10]-[C:11](=[O;D1;H0:13])-[OH;D1;+0:12])-[C:6](=[O;D1;H0:7])-[O;D1;H1:8] | null | [] | null | null | null | null | The procedure used was the same as for N-(3-(4-arsenosophenylcarbamoylmethylthio)-propanoyl)-L-aspartic acid, using 2.63 mL (184 μmol) of 70.0 mM BRAO in DMSO, the disulfide of disodium N-(3-mercaptopropanoyl)-L-glutamate (0.61 g), 0.5 M bicarbonate buffer, pH 9 (10.52 mL, 5.3 mmol), and 0.69 M triphenylphosphine in DM... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amide.Aliphatic thiol | Carboxylic acid | null | null | c1ccccc1 | Other | CS(=O)C | null | null | O=C([O-])CC[C@H](NC(=O)CCS)C(=O)[O-].O=[As]c1ccc(NC(=O)CSCCC(=O)N[C@@H](CC(=O)O)C(=O)O)cc1>CS(=O)C>O=[As]c1ccc(NC(=O)CSCCC(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fade2171f5ec4ebca010a1abc225720a | O=C(CCS)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O.O=[As]c1ccc(NC(=O)CSCCC(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1>>O=[As]c1ccc(NC(=O)CSCCC(=O)N[C@H]2C(O)O[C@H](CO)[C@@H](O)[C@@H]2O)cc1 | [As](=O)C1=CC=C(C=C1)NC(=O)CSCCC(=O)N[C@@H](CCC(=O)O)C(=O)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.SCCC(=O)N[C@H]1C(O)O[C@@H]([C@H]([C@@H]1O)O)CO.[Na].[Na].C([O-])(O)=O>>[As](=O)C1=CC=C(C=C1)NC(=O)CSCCC(=O)N[C@H]1C(O)O[C@@H]([C@H]([C@@H]1O)O)CO | O=C(CCS)[NH:16][C@H:17]1[CH:18]([OH:19])[O:20][C@H:21]([CH2:22][OH:23])[C@@H:24]([OH:25])[C@@H:26]1[OH:27].O=C(O)CC[C@H](N[C:14]([CH2:13][CH2:12][S:11][CH2:10][C:8]([NH:7][c:6]1[cH:5][cH:4][c:3]([As:2]=[O:1])[cH:29][cH:28]1)=[O:9])=[O:15])C(=O)O>>[O:1]=[As:2][c:3]1[cH:4][cH:5][c:6]([NH:7][C:8](=[O:9])[CH2:10][S:11][CH2... | O=C(CCS)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O.O=[As]c1ccc(NC(=O)CSCCC(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1 | O=[As]c1ccc(NC(=O)CSCCC(=O)N[C@H]2C(O)O[C@H](CO)[C@@H](O)[C@@H]2O)cc1 | null | null | CS(=O)C | Acylation | OtherReaction | 36506d5556b04762dba6d7c1cd60be5c7bff26fb8832038c2f0dd5528c975f1c | 0e1078419ee18e1670d05b07c6b68c5e4f56a22cbc2db8c51866c068bd88bea7 | O=C(CSCCC(=O)N[C@@H]1CCCOC1)Nc1ccccc1 | O-C(=O)-C-C-[C@H](-N-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4])-C(-O)=O.O=C(-C-C-S)-[NH;D2;+0:5]-[C:6](-[C:7])-[C:8]-[#8:9]>>[#8:9]-[C:8]-[C:6](-[NH;D2;+0:5]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4])-[C:7] | null | [] | null | null | null | null | The procedure used was the same as for N-(3-(4-arsenosophenylcarbamoylmethylthio)propanoyl)-L-glutamic acid, using 3.00 mL (210 μmol) of 70.0 mM BRAO in DMSO, the disulfide of disodium N-(3-mercaptopropanoyl)-D-glucosamine (0.67 g), 0.5 M bicarbonate buffer, pH 9 (11.96 mL, 600 mmol), and 0.69 M triphenylphosphine in D... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Secondary amide.Secondary amide.Aliphatic thiol | Secondary amide | null | null | c1ccccc1.C1CCOCC1 | Other | CS(=O)C | null | null | O=C(CCS)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O.O=[As]c1ccc(NC(=O)CSCCC(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1>CS(=O)C>O=[As]c1ccc(NC(=O)CSCCC(=O)N[C@H]2C(O)O[C@H](CO)[C@@H](O)[C@@H]2O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5142d963d8614728b1d522ca8767fa7b | C1CNCCN2CCNCCNCCN(CCN1)CCNCCNCC2>>C1=NCCN2CCN=CC=NCCN(CCN=C1)CCN=CC=NCC2 | N12CCNCCNCCN(CCNCCNCC1)CCNCCNCC2.N12CCNCCNCCN(CCNCCNCC1)CCNCCNCC2.[Ba].C(=O)C=O.C(CN(CCN)CCN)N>>N12CCN=CC=NCCN(CCN=CC=NCC1)CCN=CC=NCC2 | C1C[NH:24][CH2:25][CH2:26][N:5]2[CH2:4][CH2:3][NH:2][CH2:1][CH2:18][NH:17][CH2:16][CH2:15][N:14]([CH2:13][CH2:12][NH:11][CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[CH2:19][CH2:20][NH:21]1>>[CH:1]1=[N:2][CH2:3][CH2:4][N:5]2[CH2:6][CH2:7][N:8]=[CH:9][CH:10]=[N:11][CH2:12][CH2:13][N:14]([CH2:15][CH2:16][N:17]=[CH:18]1)[CH2:19][... | C1CNCCN2CCNCCNCCN(CCN1)CCNCCNCC2 | C1=NCCN2CCN=CC=NCCN(CCN=C1)CCN=CC=NCC2 | null | null | null | Miscellaneous | OtherReaction | f8ba7851142a0b7a435fa037a1b65660f9664d57597b2c2f3d3997a3cba5624c | 63a5a62a11d930508436c8a721d8a35fb3b9e902d518606541c6db931fef6462 | C1=NCCN2CCN=CC=NCCN(CCN=C1)CCN=CC=NCC2 | C1-C-[NH;D2;+0:1]-[C:2]-[C:3]-[#7:4]2-[C:5]-[C:6]-[NH;D2;+0:7]-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[NH;D2;+0:10]-[C:11]-[C:12]-[#7:13](-[C:14]-[C:15]-[NH;D2;+0:16]-[CH2;D2;+0:17]-[CH2;D2;+0:18]-[NH;D2;+0:19]-[C:20]-[C:21]-2)-[C:22]-[C:23]-[NH;D2;+0:24]-1>>[C:15]1-[C:14]-[#7:13]2-[C:12]-[C:11]-[N;H0;D2;+0:10]=[CH;D2;+0:9]-[CH;D... | null | [] | null | null | null | null | There is interest in nitrogen-donor cryptands for the preparation of room-temperature stable alkalides and electrides (Kim, J., et al., J. Am. Chem. Soc., 121 10666-10667 (1999)) which led to reinvestigation of the synthesis of 1,4,7,10,13,16,21,24-octaazabicyclo[8.8.8]hexacosane (1), the aza analog of cryptand [2.2.2]... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Secondary amine.Secondary amine.Secondary amine.Secondary amine.Secondary amine | Substituted imine.Substituted imine.Substituted imine.Substituted imine.Substituted imine.Substituted imine | C1CNCCN2CCNCCNCCN(CCN1)CCNCCNCC2 | C1=NCCN2CCN=CC=NCCN(CCN=C1)CCN=CC=NCC2 | C1=NCCN2CCN=CC=NCCN(CCN=C1)CCN=CC=NCC2 | null | null | null | null | C1CNCCN2CCNCCNCCN(CCN1)CCNCCNCC2>>C1=NCCN2CCN=CC=NCCN(CCN=C1)CCN=CC=NCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6fc82c8a128a4762b4fe4e7a617d8fbd | C1CNCCN2CCNCCNCCN(CCN1)CCNCCNCC2.NCCN(CCN)CCN>>C1CNCCN2CCNCCNCCN(CCN1)CCNCCNCC2.N | N12CCNCCNCCN(CCNCCNCC1)CCNCCNCC2.N12CCN=CC=NCCN(CCN=CC=NCC1)CCN=CC=NCC2.C(=O)C=O.NCCN(CCN)CCN.C(=O)C=O>>N.N12CCNCCNCCN(CCNCCNCC1)CCNCCNCC2.N12CCN=CC=NCCN(CCN=CC=NCC1)CCN=CC=NCC2 | [CH2:27]1[CH2:28][NH:29][CH2:30][CH2:31][N:32]2[CH2:33][CH2:34][NH:35][CH2:36][CH2:37][NH:38][CH2:39][CH2:40][N:41]([CH2:42][CH2:43][NH:44]1)[CH2:45][CH2:46][NH:47][CH2:48][CH2:49][NH:50][CH2:51][CH2:52]2.NCCN(CCN)CC[NH2:53]>>[CH2:27]1[CH2:28][NH:29][CH2:30][CH2:31][N:32]2[CH2:33][CH2:34][NH:35][CH2:36][CH2:37][NH:38][... | C1CNCCN2CCNCCNCCN(CCN1)CCNCCNCC2.NCCN(CCN)CCN | C1CNCCN2CCNCCNCCN(CCN1)CCNCCNCC2.N | null | null | O | Miscellaneous | OtherReaction | 36971b47ce0721c538a6ba2e7fa89e7be33f535be7997e002232d5832a88bf0e | 5b6c0451a13b3b4b2b77a6b81b1035ce59879090826074fcdb2cb74edd4b09e4 | C1CNCCN2CCNCCNCCN(CCN1)CCNCCNCC2 | N-C-C-N(-C-C-N)-C-C-[NH2;D1;+0:1]>>[NH3;D0;+0:1] | null | [] | null | null | null | null | The present invention also relates to a process for the preparation of 1,4,7,10,13,16,21,24-octaazabicyclo[8.8.8]hexacosane (1) which comprises: reacting in a non-reactive gas atmosphere a mixture of tris (2-aminoethyl)amine (tren) with glyoxal in the presence of water, a water miscible solvent and a tertiary amine wit... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine.Primary amine.Tertiary amine | null | null | null | C1CNCCN2CCNCCNCCN(CCN1)CCNCCNCC2 | Other | O | null | null | C1CNCCN2CCNCCNCCN(CCN1)CCNCCNCC2.NCCN(CCN)CCN>O>C1CNCCN2CCNCCNCCN(CCN1)CCNCCNCC2.N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9876b5db7b444962811c98f10c017d2b | C1CNCCN2CCNCCNCCN(CCN1)CCNCCNCC2.NCCN(CCN)CCN>>C1CNCCN2CCNCCNCCN(CCN1)CCNCCNCC2.N | N12CCNCCNCCN(CCNCCNCC1)CCNCCNCC2.C(=O)C=O.N12CCN=CC=NCCN(CCN=CC=NCC1)CCN=CC=NCC2.NCCN(CCN)CCN.C(=O)C=O.N12CCN=CC=NCCN(CCN=CC=NCC1)CCN=CC=NCC2.N12CCN=CC=NCCN(CCN=CC=NCC1)CCN=CC=NCC2>>N.N12CCNCCNCCN(CCNCCNCC1)CCNCCNCC2.N12CCN=CC=NCCN(CCN=CC=NCC1)CCN=CC=NCC2 | [CH2:27]1[CH2:28][NH:29][CH2:30][CH2:31][N:32]2[CH2:33][CH2:34][NH:35][CH2:36][CH2:37][NH:38][CH2:39][CH2:40][N:41]([CH2:42][CH2:43][NH:44]1)[CH2:45][CH2:46][NH:47][CH2:48][CH2:49][NH:50][CH2:51][CH2:52]2.NCCN(CCN)CC[NH2:53]>>[CH2:27]1[CH2:28][NH:29][CH2:30][CH2:31][N:32]2[CH2:33][CH2:34][NH:35][CH2:36][CH2:37][NH:38][... | C1CNCCN2CCNCCNCCN(CCN1)CCNCCNCC2.NCCN(CCN)CCN | C1CNCCN2CCNCCNCCN(CCN1)CCNCCNCC2.N | null | null | C(C)N(CC)CC.C(C)(C)O | Miscellaneous | OtherReaction | 36971b47ce0721c538a6ba2e7fa89e7be33f535be7997e002232d5832a88bf0e | 5b6c0451a13b3b4b2b77a6b81b1035ce59879090826074fcdb2cb74edd4b09e4 | C1CNCCN2CCNCCNCCN(CCN1)CCNCCNCC2 | N-C-C-N(-C-C-N)-C-C-[NH2;D1;+0:1]>>[NH3;D0;+0:1] | null | [] | null | null | null | null | The present invention also relates to a process for the preparation of 1,4,7,10,13,16,21,24-octaazabicyclo[8.8.8]hexacosane (1) which comprises: reacting in a non-reactive gas atmosphere a mixture of tris(2-aminoethyl)amine (tren), isopropyl alcohol (i-PrOH) and triethylamine (Et3N) with glyoxal with a first cooling of... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine.Primary amine.Tertiary amine | null | null | null | C1CNCCN2CCNCCNCCN(CCN1)CCNCCNCC2 | Other | C(C)N(CC)CC.C(C)(C)O | null | null | C1CNCCN2CCNCCNCCN(CCN1)CCNCCNCC2.NCCN(CCN)CCN>C(C)N(CC)CC.C(C)(C)O>C1CNCCN2CCNCCNCCN(CCN1)CCNCCNCC2.N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0e8c1bb6a9204f87b65d9dd37506e727 | CCN(C(C)=O)c1cccc(C(=O)C=CN(C)C)c1.N#Cc1c[nH]nc1N>>CCN(C(C)=O)c1cccc(-c2ccnc3c(C#N)cnn23)c1 | O=O.CN(C=CC(=O)C=1C=C(C=CC1)N(C(C)=O)CC)C.NC1=NNC=C1C#N>>CCN(C=1C=CC=C(C1)C2=CC=NC=3N2N=CC3C#N)C(=O)C | CN(C)[CH:14]=[CH:13][C:12](=O)[c:11]1[cH:10][cH:9][cH:8][c:7]([N:3]([CH2:2][CH3:1])[C:4]([CH3:5])=[O:6])[cH:23]1.[NH2:15][c:16]1[c:17]([C:18]#[N:19])[cH:20][nH:21][n:22]1>>[CH3:1][CH2:2][N:3]([C:4]([CH3:5])=[O:6])[c:7]1[cH:8][cH:9][cH:10][c:11](-[c:12]2[cH:13][cH:14][n:15][c:16]3[c:17]([C:18]#[N:19])[cH:20][n:21][n:22]... | CCN(C(C)=O)c1cccc(C(=O)C=CN(C)C)c1.N#Cc1c[nH]nc1N | CCN(C(C)=O)c1cccc(-c2ccnc3c(C#N)cnn23)c1 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | 96776ab271e66aa9498d22bf4895610823debf6383f7e2056bca170b2b60c022 | 11da551d0a7bf93f6d300d0e461ec1d4a2060497908163f95323146dc93cd499 | c1ccc(-c2ccnc3ccnn23)cc1 | C-N(-C)-[CH;D2;+0:1]=[CH;D2;+0:2]-[C;H0;D3;+0:3](=O)-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8].[NH2;D1;+0:9]-[c:10]1:[c:11]:[c:12]:[nH;D2;+0:13]:[n;H0;D2;+0:14]:1>>[c:8]:[c:7]:[c;H0;D3;+0:4](-[c;H0;D3;+0:3]1:[cH;D2;+0:2]:[cH;D2;+0:1]:[n;H0;D2;+0:9]:[c:10]2:[c:11]:[c:12]:[n;H0;D2;+0:13]:[n;H0;D3;+0:14]:2:1):[c:5]:[c:6] | 91 | [{"value": 91.0, "product": "CCN(C=1C=CC=C(C1)C2=CC=NC=3N2N=CC3C#N)C(=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | WO O2/100828 A2 discloses a further improvement in the '538 process by reacting the same intermediates, N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]-N-ethylacetamide and 3-amino-4-cyanopyrazole, in a liquid medium of water and a water-miscible organic compound under acidic conditions. Although the reaction is claim... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ketone.Primary amine | null | c1cn[nH]c1 | c1cnc2ccnn2c1 | c1ccccc1.c1cnc2ccnn2c1 | HO- | O | null | null | CCN(C(C)=O)c1cccc(C(=O)C=CN(C)C)c1.N#Cc1c[nH]nc1N>O>CCN(C(C)=O)c1cccc(-c2ccnc3c(C#N)cnn23)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-04e9fdd4be344ec89e6c72bfdcb0480a | Nc1cccs1.O=[N+]([O-])c1ccccc1F>>O=[N+]([O-])c1ccccc1Nc1cccs1 | NC=1SC=CC1.[N+](=O)([O-])C1=C(C=CC=C1)F>>[N+](=O)([O-])C1=C(NC=2SC=CC2)C=CC=C1 | [NH2:10][c:11]1[cH:12][cH:13][cH:14][s:15]1.F[c:9]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][cH:6][cH:7][cH:8]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[NH:10][c:11]1[cH:12][cH:13][cH:14][s:15]1 | Nc1cccs1.O=[N+]([O-])c1ccccc1F | O=[N+]([O-])c1ccccc1Nc1cccs1 | null | null | null | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2cccs2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[#16;a:10]:[c:11]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[#16;a:10]:[c:11]):[c:2]:[c:3] | null | [] | null | null | null | null | Both paths start with a Gewald reaction to form appropriately substituted 2-amino-thiophenes (a). This type of reaction is described in Chem. Ber. 1965, 98, 3571-3577; Chem. Ber. 1966, 99, 94-100. The second step involves the reaction of 2-aminothiophene with 2-nitro-1-fluorobenzene (b), to give a 2-(2-nitro-anilino)th... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccsc1 | HF | null | null | null | Nc1cccs1.O=[N+]([O-])c1ccccc1F>>O=[N+]([O-])c1ccccc1Nc1cccs1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-582cb0c430004610875bfb0ff5aad5c3 | CN1CCNCC1.CS(C)=O.NC1=Nc2ccccc2N=C(N)C1>>CN1CCN(C2=Nc3ccccc3N=C(N3CCN(C)CC3)C2)CC1 | N1=C(CC(=NC2=C1C=CC=C2)N)N.CS(=O)C.CN1CCNCC1>>CN1CCN(CC1)C=1CC(=NC2=C(N1)C=CC=C2)N2CCN(CC2)C | [CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:24][CH2:25]1.O=S([CH3:17])[CH3:20].[C:6]1([NH2:19])=[N:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[N:14]=[C:15]([NH2:16])[CH2:23]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6]2=[N:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[N:14]=[C:15]([N:16]3[CH2:17][CH2:18][N:19]([CH3:20])[CH2:21][CH2:... | CN1CCNCC1.CS(C)=O.NC1=Nc2ccccc2N=C(N)C1 | CN1CCN(C2=Nc3ccccc3N=C(N3CCN(C)CC3)C2)CC1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 230aacd78d7e77a983ed7252a3f7d8fbbb77e5b6ddc4731b45460cb6016141cc | bc45e941fab0ddc16b61dbe72b02c40f7e87d6dfe92f3a2a70162befb3c1d510 | c1ccc2c(c1)N=C(N1CCNCC1)CC(N1CCNCC1)=N2 | O=S(-[CH3;D1;+0:1])-[CH3;D1;+0:2].[#7:3]1-[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]-1.[NH2;D1;+0:9]-[C:10]1=[#7:11]-[c:12]:[c:13]-[#7:14]=[C;H0;D3;+0:15](-[NH2;D1;+0:16])-[C:17]-1>>[CH3;D1;+0:2]-[N;H0;D3;+0:16]1-[C:18]-[CH2;D2;+0:1]-[N;H0;D3;+0:9](-[C:10]2=[#7:11]-[c:12]:[c:13]-[#7:14]=[C;H0;D3;+0:15](-[N;H0;D3;+0:6]3-[C:5]... | 74 | [{"value": 74.0, "product": "CN1CCN(CC1)C=1CC(=NC2=C(N1)C=CC=C2)N2CCN(CC2)C", "details": "PERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | 3H-[1,5]Benzodiazepine-2,4-diamine (32.50 g, 160 mmol, 86%) was added to a solution of dimethyl sulfoxide (220 ml), toluene (220 ml) and 1-methylpiperazine (165 ml). The mixture was heated for 16 h at 120° C. After cooling the product precipitated. It was filtered off and washed with isopropyl ether (80 ml) to give 40.... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine.Secondary amine.Sulfoxide | Tertiary amine.Tertiary amine.Tertiary amine | C1C[NH]CCN1.C1=Nc2ccccc2N=CC1 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N=CC1.C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N=CC1.C1C[NH]CC[NH]1 | null | C1(=CC=CC=C1)C | 120 | null | CN1CCNCC1.CS(C)=O.NC1=Nc2ccccc2N=C(N)C1>C1(=CC=CC=C1)C>CN1CCN(C2=Nc3ccccc3N=C(N3CCN(C)CC3)C2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e7a00b85ee584f81a8e05b4ea71e8100 | CCC=O.CN1CCN(C2=Nc3ccccc3N=C(N3CCN(C)CC3)C2)CC1>>CCC(O)C1C(N2CCN(C)CC2)=Nc2ccccc2N=C1N1CCN(C)CC1 | O.C(C)(C)[N-]C(C)C.[Li+].CN1CCN(CC1)C=1CC(=NC2=C(N1)C=CC=C2)N2CCN(CC2)C.C(CC)=O>>CN1CCN(CC1)C=1C(C(=NC2=C(N1)C=CC=C2)N2CCN(CC2)C)C(CC)O | [CH3:1][CH2:2][CH:3]=[O:4].[CH2:5]1[C:6]([N:7]2[CH2:8][CH2:9][N:10]([CH3:11])[CH2:12][CH2:13]2)=[N:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[N:21]=[C:22]1[N:23]1[CH2:24][CH2:25][N:26]([CH3:27])[CH2:28][CH2:29]1>>[CH3:1][CH2:2][CH:3]([OH:4])[CH:5]1[C:6]([N:7]2[CH2:8][CH2:9][N:10]([CH3:11])[CH2:12][CH2:13]2)=[N:14][c... | CCC=O.CN1CCN(C2=Nc3ccccc3N=C(N3CCN(C)CC3)C2)CC1 | CCC(O)C1C(N2CCN(C)CC2)=Nc2ccccc2N=C1N1CCN(C)CC1 | null | null | O1CCCC1.C(Cl)(Cl)Cl | C-C Coupling | OtherReaction | f974512da8891223359f5856665b89b2ef1b61a21e358a2a11f5e24ea6c6f455 | a7cae52d902b2812376f5459a7a8b7ead54e8ef31fd78982d2e99bec532613ba | c1ccc2c(c1)N=C(N1CCNCC1)CC(N1CCNCC1)=N2 | [#7:1]-[C:2]1=[#7:3]-[c:4]:[c:5]-[#7:6]=[C:7](-[#7:8])-[CH2;D2;+0:9]-1.[C;D1;H3:10]-[C:11]-[CH;D2;+0:12]=[O;H0;D1;+0:13]>>[#7:1]-[C:2]1=[#7:3]-[c:4]:[c:5]-[#7:6]=[C:7](-[#7:8])-[CH;D3;+0:9]-1-[CH;D3;+0:12](-[OH;D1;+0:13])-[C:11]-[C;D1;H3:10] | 92 | [{"value": 92.0, "product": "CN1CCN(CC1)C=1C(C(=NC2=C(N1)C=CC=C2)N2CCN(CC2)C)C(CC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.0, "product": "CN1CCN(CC1)C=1C(C(=NC2=C(N1)C=CC=C2)N2CCN(CC2)C)C(CC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -30 | CELSIUS | null | null | A suspension of 2,4-bis(4-methyl-1-piperazinyl)-3H-[1,5]benzodiazepine (17.024 g, 50 mmol) in tetrahydrofuran (200 ml) under constant flow of argon was cooled to −30° C. A solution of lithium diisopropylamide (LDA) (2 M, 37.5 ml, 75 mmol) was added dropwise. Thus obtained dark brown suspension was allowed to warm to −5... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary alcohol | C1=Nc2ccccc2N=CC1 | C1=Nc2ccccc2N=CC1 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N=CC1.C1C[NH]CC[NH]1 | null | O1CCCC1.C(Cl)(Cl)Cl | -30 | null | CCC=O.CN1CCN(C2=Nc3ccccc3N=C(N3CCN(C)CC3)C2)CC1>O1CCCC1.C(Cl)(Cl)Cl>CCC(O)C1C(N2CCN(C)CC2)=Nc2ccccc2N=C1N1CCN(C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b122cf529c28402ba6b23f656be4f042 | CCC=O.CN1CCN(C2=Nc3ccccc3N=C(N3CCN(C)CC3)C2)CC1>>CCC=C1C(N2CCN(C)CC2)=Nc2ccccc2N=C1N1CCN(C)CC1 | C(CC)=O.[OH-].[Na+].FC(C(=O)OC(C(F)(F)F)=O)(F)F.C(C)(C)[N-]C(C)C.[Li+].C(C)N(CC)CC.N1=CC=CC=C1.CN1CCN(CC1)C=1CC(=NC2=C(N1)C=CC=C2)N2CCN(CC2)C>>CN1CCN(CC1)C=1C(C(=NC2=C(N1)C=CC=C2)N2CCN(CC2)C)=CCC | O=[CH:3][CH2:2][CH3:1].[CH2:4]1[C:5]([N:6]2[CH2:7][CH2:8][N:9]([CH3:10])[CH2:11][CH2:12]2)=[N:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[N:20]=[C:21]1[N:22]1[CH2:23][CH2:24][N:25]([CH3:26])[CH2:27][CH2:28]1>>[CH3:1][CH2:2][CH:3]=[C:4]1[C:5]([N:6]2[CH2:7][CH2:8][N:9]([CH3:10])[CH2:11][CH2:12]2)=[N:13][c:14]2[cH:15][c... | CCC=O.CN1CCN(C2=Nc3ccccc3N=C(N3CCN(C)CC3)C2)CC1 | CCC=C1C(N2CCN(C)CC2)=Nc2ccccc2N=C1N1CCN(C)CC1 | null | null | O1CCCC1.CO | C-C Coupling | OtherReaction | 5f84e778947cde25eb401df9b5f8de4c39579e7ebdadd4660585f2c805303e63 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | [CH]=C1C(N2CCNCC2)=Nc2ccccc2N=C1N1CCNCC1 | O=[CH;D2;+0:1]-[C:2]-[C;D1;H3:3].[#7:4]-[C:5]1=[#7:6]-[c:7]:[c:8]-[#7:9]=[C:10](-[#7:11])-[CH2;D2;+0:12]-1>>[#7:4]-[C:5]1=[#7:6]-[c:7]:[c:8]-[#7:9]=[C:10](-[#7:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[C:2]-[C;D1;H3:3] | 36,843.4 | [{"value": 89.0, "product": "CN1CCN(CC1)C=1C(C(=NC2=C(N1)C=CC=C2)N2CCN(CC2)C)=CCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36843.4, "product": "CN1CCN(CC1)C=1C(C(=NC2=C(N1)C=CC=C2)N2CCN(CC2)C)=CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -30 | CELSIUS | null | null | A suspension of 2,4-bis(4-methyl-1-piperazinyl)-3H-[1,5]benzodiazepine (1.702 g, 5 mmol) in tetrahydrofuran (20 ml) under constant flow of argon was cooled to −30° C. A solution of lithium diisopropylamide (LDA) (2 M, 3.75 ml, 7.5 mmol) was added dropwise. Thus obtained dark brown suspension was allowed to warm to −5° ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | C1=Nc2ccccc2N=CC1 | C1=Nc2ccccc2N=CC1 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N=CC1.C1C[NH]CC[NH]1 | HO- | O1CCCC1.CO | -30 | null | CCC=O.CN1CCN(C2=Nc3ccccc3N=C(N3CCN(C)CC3)C2)CC1>O1CCCC1.CO>CCC=C1C(N2CCN(C)CC2)=Nc2ccccc2N=C1N1CCN(C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-543564be2c4b452e9aa1c6dde5f5860e | CCC(O)C1C(N2CCN(C)CC2)=Nc2ccccc2N=C1N1CCN(C)CC1>>CCC=C1C(N2CCN(C)CC2)=Nc2ccccc2N=C1N1CCN(C)CC1 | FC(C(=O)OC(C(F)(F)F)=O)(F)F.CN1CCN(CC1)C=1C(C(=NC2=C(N1)C=CC=C2)N2CCN(CC2)C)C(CC)O.C(C)N(CC)CC.N1=CC=CC=C1.[OH-].[Na+]>>CN1CCN(CC1)C=1C(C(=NC2=C(N1)C=CC=C2)N2CCN(CC2)C)=CCC | O[CH:3]([CH2:2][CH3:1])[CH:4]1[C:5]([N:6]2[CH2:7][CH2:8][N:9]([CH3:10])[CH2:11][CH2:12]2)=[N:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[N:20]=[C:21]1[N:22]1[CH2:23][CH2:24][N:25]([CH3:26])[CH2:27][CH2:28]1>>[CH3:1][CH2:2][CH:3]=[C:4]1[C:5]([N:6]2[CH2:7][CH2:8][N:9]([CH3:10])[CH2:11][CH2:12]2)=[N:13][c:14]2[cH:15][cH... | CCC(O)C1C(N2CCN(C)CC2)=Nc2ccccc2N=C1N1CCN(C)CC1 | CCC=C1C(N2CCN(C)CC2)=Nc2ccccc2N=C1N1CCN(C)CC1 | null | null | ClCCl.O1CCCC1.CO | Functional Group Interconversion | OtherReaction | 0bb60ba0b0e02b49ef6b197543c249cd957a9c7120ef53710548a4b3ffdf4fb9 | f8118e7f3e1d7109575c0c77239dee8da98ec71a2b23460bcda2084274bdf7e7 | [CH]=C1C(N2CCNCC2)=Nc2ccccc2N=C1N1CCNCC1 | O-[CH;D3;+0:1](-[C:2]-[C;D1;H3:3])-[CH;D3;+0:4]1-[C:5](-[#7:6])=[#7:7]-[c:8]:[c:9]-[#7:10]=[C:11]-1-[#7:12]>>[#7:6]-[C:5]1=[#7:7]-[c:8]:[c:9]-[#7:10]=[C:11](-[#7:12])-[C;H0;D3;+0:4]-1=[CH;D2;+0:1]-[C:2]-[C;D1;H3:3] | 85.1 | [{"value": 84.0, "product": "CN1CCN(CC1)C=1C(C(=NC2=C(N1)C=CC=C2)N2CCN(CC2)C)=CCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.1, "product": "CN1CCN(CC1)C=1C(C(=NC2=C(N1)C=CC=C2)N2CCN(CC2)C)=CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | To a suspension of 1-[2,4-bis(4-methyl-1-piperazinyl)-3H-[1,5]benzodiazepin-3-yl]-1-propanol (1.195 g, 3 mmol), triethylamine (2.50 ml, 18 mmol) and pyridine (0.024 ml, 0.3 mmol) in tetrahydrofuran (10 ml) under constant flow of argon, at 0° C., a solution of trifluoroacetic anhydride (1.26 ml, 9 mmol) in tetrahydrofur... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | C1=Nc2ccccc2N=CC1 | C1=Nc2ccccc2N=CC1 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N=CC1.C1C[NH]CC[NH]1 | HO- | ClCCl.O1CCCC1.CO | 0 | null | CCC(O)C1C(N2CCN(C)CC2)=Nc2ccccc2N=C1N1CCN(C)CC1>ClCCl.O1CCCC1.CO>CCC=C1C(N2CCN(C)CC2)=Nc2ccccc2N=C1N1CCN(C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1e0c4f3c945e4e7e8a516efbac4e0901 | CCC(O)C1C(N2CCN(C)CC2)=Nc2ccccc2N=C1N1CCN(C)CC1>>CCC=C1C(N2CCN(C)CC2)=Nc2ccccc2N=C1N1CCN(C)CC1 | [OH-].[Na+].CN1CCN(CC1)C=1C(C(=NC2=C(N1)C=CC=C2)N2CCN(CC2)C)C(CC)O.C(C)N(CC)CC.FC(C(=O)OC(C(F)(F)F)=O)(F)F>>CN1CCN(CC1)C=1C(C(=NC2=C(N1)C=CC=C2)N2CCN(CC2)C)=CCC | O[CH:3]([CH2:2][CH3:1])[CH:4]1[C:5]([N:6]2[CH2:7][CH2:8][N:9]([CH3:10])[CH2:11][CH2:12]2)=[N:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[N:20]=[C:21]1[N:22]1[CH2:23][CH2:24][N:25]([CH3:26])[CH2:27][CH2:28]1>>[CH3:1][CH2:2][CH:3]=[C:4]1[C:5]([N:6]2[CH2:7][CH2:8][N:9]([CH3:10])[CH2:11][CH2:12]2)=[N:13][c:14]2[cH:15][cH... | CCC(O)C1C(N2CCN(C)CC2)=Nc2ccccc2N=C1N1CCN(C)CC1 | CCC=C1C(N2CCN(C)CC2)=Nc2ccccc2N=C1N1CCN(C)CC1 | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | ClCCl.CO | Functional Group Interconversion | OtherReaction | 0bb60ba0b0e02b49ef6b197543c249cd957a9c7120ef53710548a4b3ffdf4fb9 | f8118e7f3e1d7109575c0c77239dee8da98ec71a2b23460bcda2084274bdf7e7 | [CH]=C1C(N2CCNCC2)=Nc2ccccc2N=C1N1CCNCC1 | O-[CH;D3;+0:1](-[C:2]-[C;D1;H3:3])-[CH;D3;+0:4]1-[C:5](-[#7:6])=[#7:7]-[c:8]:[c:9]-[#7:10]=[C:11]-1-[#7:12]>>[#7:6]-[C:5]1=[#7:7]-[c:8]:[c:9]-[#7:10]=[C:11](-[#7:12])-[C;H0;D3;+0:4]-1=[CH;D2;+0:1]-[C:2]-[C;D1;H3:3] | 76 | [{"value": 76.0, "product": "CN1CCN(CC1)C=1C(C(=NC2=C(N1)C=CC=C2)N2CCN(CC2)C)=CCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.9, "product": "CN1CCN(CC1)C=1C(C(=NC2=C(N1)C=CC=C2)N2CCN(CC2)C)=CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | To a suspension of 1-[2,4-bis(4-methyl-1-piperazinyl)-3H-[1,5]benzodiazepin-3-yl]-1-propanol (19.93 g, 50 mmol) and triethylamine (45 ml, 325 mmol) in dichloromethane (100 ml) under constant flow of argon, at 0° C., a solution of trifluoroacetic anhydride (21 ml, 150 mmol) in dichloromethane (50 ml) was added dropwise.... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | C1=Nc2ccccc2N=CC1 | C1=Nc2ccccc2N=CC1 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N=CC1.C1C[NH]CC[NH]1 | HO- | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.ClCCl.CO | 0 | null | CCC(O)C1C(N2CCN(C)CC2)=Nc2ccccc2N=C1N1CCN(C)CC1>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.ClCCl.CO>CCC=C1C(N2CCN(C)CC2)=Nc2ccccc2N=C1N1CCN(C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8b5675230ec94026a54d8d3d7571bd19 | CCC=O.CN1CCN(C2=Nc3ccccc3N=C(N3CCN(C)CC3)C2)CC1>>CCC=C1C(N2CCN(C)CC2)=Nc2ccccc2N=C1N1CCN(C)CC1 | [OH-].[Na+].C(CC)=O.Cl.C(C)N(CC)CC.C(C)(C)[N-]C(C)C.[Li+].CN1CCN(CC1)C=1CC(=NC2=C(N1)C=CC=C2)N2CCN(CC2)C>>CN1CCN(CC1)C=1C(C(=NC2=C(N1)C=CC=C2)N2CCN(CC2)C)=CCC | O=[CH:3][CH2:2][CH3:1].[CH2:4]1[C:5]([N:6]2[CH2:7][CH2:8][N:9]([CH3:10])[CH2:11][CH2:12]2)=[N:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[N:20]=[C:21]1[N:22]1[CH2:23][CH2:24][N:25]([CH3:26])[CH2:27][CH2:28]1>>[CH3:1][CH2:2][CH:3]=[C:4]1[C:5]([N:6]2[CH2:7][CH2:8][N:9]([CH3:10])[CH2:11][CH2:12]2)=[N:13][c:14]2[cH:15][c... | CCC=O.CN1CCN(C2=Nc3ccccc3N=C(N3CCN(C)CC3)C2)CC1 | CCC=C1C(N2CCN(C)CC2)=Nc2ccccc2N=C1N1CCN(C)CC1 | null | N1=CC=CC=C1 | O1CCCC1.CO | C-C Coupling | OtherReaction | 5f84e778947cde25eb401df9b5f8de4c39579e7ebdadd4660585f2c805303e63 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | [CH]=C1C(N2CCNCC2)=Nc2ccccc2N=C1N1CCNCC1 | O=[CH;D2;+0:1]-[C:2]-[C;D1;H3:3].[#7:4]-[C:5]1=[#7:6]-[c:7]:[c:8]-[#7:9]=[C:10](-[#7:11])-[CH2;D2;+0:12]-1>>[#7:4]-[C:5]1=[#7:6]-[c:7]:[c:8]-[#7:9]=[C:10](-[#7:11])-[C;H0;D3;+0:12]-1=[CH;D2;+0:1]-[C:2]-[C;D1;H3:3] | 95.4 | [{"value": 95.0, "product": "CN1CCN(CC1)C=1C(C(=NC2=C(N1)C=CC=C2)N2CCN(CC2)C)=CCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.4, "product": "CN1CCN(CC1)C=1C(C(=NC2=C(N1)C=CC=C2)N2CCN(CC2)C)=CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -10 | CELSIUS | 30 | MINUTE | A suspension of 2,4-bis(4-methyl-1-piperazinyl)-3H-[1,5]benzodiazepine (45.396 g, 133.3 mmol) in tetrahydrofuran (560 ml) under constant flow of argon was cooled to −10° C. A solution of lithium diisopropylamide (LDA) (2M, 100 ml, 200 mmol) was added over a period of 20 min, maintaining the temperature at −10° C. The o... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | C1=Nc2ccccc2N=CC1 | C1=Nc2ccccc2N=CC1 | C1C[NH]CC[NH]1.C1=Nc2ccccc2N=CC1.C1C[NH]CC[NH]1 | HO- | N1=CC=CC=C1.O1CCCC1.CO | -10 | 0.5 | CCC=O.CN1CCN(C2=Nc3ccccc3N=C(N3CCN(C)CC3)C2)CC1>N1=CC=CC=C1.O1CCCC1.CO>CCC=C1C(N2CCN(C)CC2)=Nc2ccccc2N=C1N1CCN(C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9507b3ebe976448097f8f383c6174f7a | CCC=C1C(N2CCN(C)CC2)=Nc2ccccc2N=C1N1CCN(C)CC1.[S]>>Cc1cc2c(s1)Nc1ccccc1N=C2N1CCN(C)CC1 | CN1CCN(CC1)C=1C(C(=NC2=C(N1)C=CC=C2)N2CCN(CC2)C)=CCC.[S].C(C)N(CC)CC.CS(=O)C.Cl>>CC1=CC2=C(S1)NC=3C=CC=CC3N=C2N4CCN(CC4)C | CN1CCN([C:5]2=[N:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[N:14]=[C:15]([N:16]3[CH2:17][CH2:18][N:19]([CH3:20])[CH2:21][CH2:22]3)[C:4]2=[CH:3][CH2:2][CH3:1])CC1.[S:6]>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([s:6]1)[NH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[N:14]=[C:15]2[N:16]1[CH2:17][CH2:18][N:19]([CH3:20])[CH2:21][CH2:2... | CCC=C1C(N2CCN(C)CC2)=Nc2ccccc2N=C1N1CCN(C)CC1.[S] | Cc1cc2c(s1)Nc1ccccc1N=C2N1CCN(C)CC1 | null | null | ClCCl.C(CC)O | Aromatic Heterocycle Formation | OtherReaction | 58437555b371f300221d57bfd4dee344d3eb9828826019d32e59a67a3496b757 | f46c889d27949611a36fcf899c8bd2d91cb3692c1a0cfb7a7bf34840185adb82 | c1ccc2c(c1)N=C(N1CCNCC1)c1ccsc1N2 | C-N1-C-C-N(-[C;H0;D3;+0:1]2=[N;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]-[#7:6]=[C:7](-[#7:8])-[C;H0;D3;+0:9]-2=[CH;D2;+0:10]-[CH2;D2;+0:11]-[C;D1;H3:12])-C-C-1.[S;H0;D0;+0:13]>>[#7:8]-[C:7]1=[#7:6]-[c:5]:[c:3](:[c:4])-[NH;D2;+0:2]-[c;H0;D3;+0:1]2:[s;H0;D2;+0:13]:[c;H0;D3;+0:11](-[C;D1;H3:12]):[cH;D2;+0:10]:[c;H0;D3;+0:9]:2-1 | 12 | [{"value": 12.0, "product": "CC1=CC2=C(S1)NC=3C=CC=CC3N=C2N4CCN(CC4)C", "details": "PERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A suspension of 2,4-bis(4-methyl-1-piperazinyl)-3-propylidene-3H-[1,5]benzodiazepine (11.90 g, 31.3 mmol), sulphur (20.07 g, 626 mmol) and triethyl amine (4.34 ml, 31.3 mmol) in dimethyl sulfoxide (100 ml) and 1-propanol (100 ml) was heated at 100° C. for five days. The resulting black suspension was cooled and filtere... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine.Tertiary amine | Secondary amine | C1CNCCN1.C1=Nc2ccccc2N=CC1 | C1=Nc2ccccc2Nc2sccc21 | C1=Nc2ccccc2Nc2sccc21.C1C[NH]CC[NH]1 | Other | ClCCl.C(CC)O | 100 | null | CCC=C1C(N2CCN(C)CC2)=Nc2ccccc2N=C1N1CCN(C)CC1.[S]>ClCCl.C(CC)O>Cc1cc2c(s1)Nc1ccccc1N=C2N1CCN(C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5712266dd2d843d7b502f58744faa9cc | CC1(C)NCc2ccccc2O1>>CC(C)Nc1ccccc1CO | CC1(OC2=C(CN1)C=CC=C2)C.C1CCOC1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C1CCOC1>>C(C)(C)NC1=C(C=CC=C1)CO | [CH3:1][C:2]1([CH3:3])[NH:4][CH2:11][c:10]2[c:5]([cH:6][cH:7][cH:8][cH:9]2)[O:12]1>>[CH3:1][CH:2]([CH3:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[CH2:11][OH:12] | CC1(C)NCc2ccccc2O1 | CC(C)Nc1ccccc1CO | null | null | null | Miscellaneous | OtherReaction | bf0fd08faea41f249ad245c627ae5eaa44305b733aa8f021166c9982d83d6e4c | 6731e713966699a550554bf52935dfe7a2b2eb2cafc83e524d2ff6fcc59af15d | c1ccccc1 | [C;D1;H3:1]-[C;H0;D4;+0:2]1(-[C;D1;H3:3])-[NH;D2;+0:4]-[CH2;D2;+0:5]-[c:6](:[c:7]):[c;H0;D3;+0:8](:[c:9]:[c:10])-[O;H0;D2;+0:11]-1>>[C;D1;H3:1]-[CH;D3;+0:2](-[C;D1;H3:3])-[NH;D2;+0:4]-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:6](-[CH2;D2;+0:5]-[OH;D1;+0:11]):[c:7] | 95 | [{"value": 95.0, "product": "C(C)(C)NC1=C(C=CC=C1)CO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of 2,2,-dimethyl-1,4-dihydro-2H-benzo[1,3]oxazine (125 g, 0.77 mol) in THF (1 L) was filtered through a scintillation funnel and then added dropwise via an addition funnel, over a period of 2.5 h, to a stirred solution of 1.0 M LiAlH4 in THF (800 mL) at 0° C. The reaction was quenched by slow portionwise add... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Primary alcohol.Secondary amine | c1ccc2c(c1)CNCO2 | c1ccccc1 | c1ccccc1 | null | null | null | 8 | CC1(C)NCc2ccccc2O1>>CC(C)Nc1ccccc1CO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-911a4a32cd8c43a4999e683c4feac203 | CC(C)Nc1ccccc1CO>>CC(C)Nc1ccccc1C=O | C(C)(C)NC1=C(C=CC=C1)CO>>C(C)(C)NC1=C(C=O)C=CC=C1 | [CH3:1][CH:2]([CH3:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[CH2:11][OH:12]>>[CH3:1][CH:2]([CH3:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[CH:11]=[O:12] | CC(C)Nc1ccccc1CO | CC(C)Nc1ccccc1C=O | null | [O-2].[O-2].[Mn+4] | C1(=CC=CC=C1)C | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccccc1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5] | 90.6 | [{"value": 90.0, "product": "C(C)(C)NC1=C(C=O)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.6, "product": "C(C)(C)NC1=C(C=O)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 117 | CELSIUS | null | null | Manganese dioxide (85% 182.6 g, 1.79 mol) was added to a stirred solution of 2-isopropylaminophenylmethanol (118 g, 0.71 mol) in toluene (800 mL) and the reaction mixture was heated to 117° C. for 4 h. The reaction mixture was allowed to cool to room temperature overnight and then filtered through a pad of Celite which... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1 | null | [O-2].[O-2].[Mn+4].C1(=CC=CC=C1)C | 117 | null | CC(C)Nc1ccccc1CO>[O-2].[O-2].[Mn+4].C1(=CC=CC=C1)C>CC(C)Nc1ccccc1C=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-836ed5d4326948f8846af139c8a9b36e | CC(C)Nc1ccccc1C=O.CC1(C)OC(=O)CC(=O)O1>>CC(C)n1c(=O)c(C(=O)O)cc2ccccc21 | CC1(OC(CC(O1)=O)=O)C.CC1(OC(=O)CC(=O)O1)C.C(C)(C)NC1=C(C=O)C=CC=C1.C(C)(=O)O.C(CN)N>>C(C)(C)N1C(C(=CC2=CC=CC=C12)C(=O)O)=O | O=[CH:11][c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[NH:4][CH:2]([CH3:1])[CH3:3].CC1(C)O[C:5](=[O:6])[CH2:7][C:8](=[O:9])[O:10]1>>[CH3:1][CH:2]([CH3:3])[n:4]1[c:5](=[O:6])[c:7]([C:8](=[O:9])[OH:10])[cH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12 | CC(C)Nc1ccccc1C=O.CC1(C)OC(=O)CC(=O)O1 | CC(C)n1c(=O)c(C(=O)O)cc2ccccc21 | null | null | CO | Miscellaneous | OtherReaction | 7da7c8932064b44b257d05fda8b8362a79f28b679166e64d691318db6946232e | ddbf93ce274a07b125aec0b5e9bfc602f13d41e2bbc449e0d8b2eac033b184d0 | O=c1ccc2ccccc2[nH]1 | C-C1(-C)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-1.O=[CH;D2;+0:7]-[c:8](:[c:9]):[c:10](-[NH;D2;+0:11]-[C:12](-[C;D1;H3:13])-[C;D1;H3:14]):[c:15]>>[C;D1;H3:13]-[C:12](-[C;D1;H3:14])-[n;H0;D3;+0:11]1:[c:10](:[c:15]):[c:8](:[c:9]):[cH;D2;+0:7]:[c;H0;D3;+0:3](-[C:4](=[O;D1;H0:5])-[OH... | 98 | [{"value": 98.0, "product": "C(C)(C)N1C(C(=CC2=CC=CC=C12)C(=O)O)=O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | 2,2-Dimethyl-[1,3]dioxane-4,6-dione, commonly Meldrum's acid, (166.9 g, 1.16 mol) was added to a stirred solution of 2-isopropylaminobenzaldehyde (105 g, 0.64 mol), acetic acid (73.6 mL, 1.29 mol) and ethylenediamine (43.0 mL, 0.64 mol) in methanol (1 L) at 0° C. The reaction mixture was stirred for 1 h at 0° C. and th... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester.Ester.Secondary amine | Carboxylic acid | c1ccccc1.C1COCOC1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HO- | CO | 0 | 1 | CC(C)Nc1ccccc1C=O.CC1(C)OC(=O)CC(=O)O1>CO>CC(C)n1c(=O)c(C(=O)O)cc2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cc19a12757ec4654bd758bcbb9d224fb | C1CNCCN1.CN[SH](=O)=O.ClC[C@@H]1CO1>>CS(=O)(=O)N1CCN(C[C@H](O)CCl)CC1 | C(Cl)[C@@H]1CO1.CNS(=O)=O.N1CCNCC1.C(C)O>>ClC[C@H](CN1CCN(CC1)S(=O)(=O)C)O | [NH:5]1[CH2:6][CH2:7][NH:8][CH2:14][CH2:15]1.N([CH3:1])[SH:2](=[O:3])=[O:4].[CH2:9]1[C@@H:10]([CH2:12][Cl:13])[O:11]1>>[CH3:1][S:2](=[O:3])(=[O:4])[N:5]1[CH2:6][CH2:7][N:8]([CH2:9][C@H:10]([OH:11])[CH2:12][Cl:13])[CH2:14][CH2:15]1 | C1CNCCN1.CN[SH](=O)=O.ClC[C@@H]1CO1 | CS(=O)(=O)N1CCN(C[C@H](O)CCl)CC1 | null | null | null | Protection | OtherReaction | b1d0cfa658c622676ee7327d9df82372236105c7e33c63a949aef25bb6ad5538 | e6671e6060742aee54f790d41e5fab09be0d791ee3d1f3466271576ca7438a8d | C1CNCCN1 | [CH3;D1;+0:1]-N-[SH;D3;+0:2](=[O;D1;H0:3])=[O;D1;H0:4].[C:5]1-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-[NH;D2;+0:10]-1.[Cl;D1;H0:11]-[C:12]-[C@@H;D3;+0:13]1-[CH2;D2;+0:14]-[O;H0;D2;+0:15]-1>>[CH3;D1;+0:1]-[S;H0;D4;+0:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[N;H0;D3;+0:10](-[CH2;D2;+0:14]-[C@H;D3;+0:13](-[OH;D1... | null | [] | null | null | 18 | HOUR | (S)-Epichlorohydrin (48.0 mL, 0.612 mol) was added to a stirred solution of piperazine N-methylsulfonamide (87.3 g, 0.532 mol) in ethanol (1.33 L) at room temperature. The reaction mixture was stirred for 18 h and the white solid precipitate which formed was collected by filtration and washed with ethanol to afford (S)... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Ether.Secondary amine.Secondary amine | Secondary alcohol.Tertiary amine.Tertiary amine | C1CNCCN1.C1CO1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1 | Other | null | null | 18 | C1CNCCN1.CN[SH](=O)=O.ClC[C@@H]1CO1>>CS(=O)(=O)N1CCN(C[C@H](O)CCl)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b7b288b0fae543ada466fd64394a99a7 | C=CCBr.COC(CNc1cnc(Cl)c(Cl)c1)OC>>C=CCN(CC(OC)OC)c1cnc(Cl)c(Cl)c1 | ClC=1C=C(C=NC1Cl)NCC(OC)OC.C(C=C)Br>>C(C=C)N(CC(OC)OC)C=1C=NC(=C(C1)Cl)Cl | Br[CH2:3][CH:2]=[CH2:1].[NH:4]([CH2:5][CH:6]([O:7][CH3:8])[O:9][CH3:10])[c:11]1[cH:12][n:13][c:14]([Cl:15])[c:16]([Cl:17])[cH:18]1>>[CH2:1]=[CH:2][CH2:3][N:4]([CH2:5][CH:6]([O:7][CH3:8])[O:9][CH3:10])[c:11]1[cH:12][n:13][c:14]([Cl:15])[c:16]([Cl:17])[cH:18]1 | C=CCBr.COC(CNc1cnc(Cl)c(Cl)c1)OC | C=CCN(CC(OC)OC)c1cnc(Cl)c(Cl)c1 | null | [Cl-].C[N+](CCCC)(CCCC)CCCC | C(C)(C)(C)OC.[OH-].[Na+] | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | f41840cb514801a9cb1d5daa03acb2d980295bce2299a2397b84c433eee890b2 | 17be7e5233143f3f5efba3e4456f48662a03854e74790b373fce106317c9bff2 | c1ccncc1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[C:4]-[C:5]-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]:[c:11]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3])-[c:7](:[c:8]):[c:9]:[#7;a:10]:[c:11] | null | [] | null | null | null | null | As shown in Scheme 2, the sequential treatment of 2-hydroxy-5-nitropyridine with potassium chlorate under heated conditions provides 3-chloro-2-hydroxy-5-nitropyridine which when further treated with phosphorous oxychloride under heated conditions provides 2,3-dichloro-5-nitropyridine. The nitro containing compound whe... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine.Allyl | null | null | c1ccncc1 | HBr | [Cl-].C[N+](CCCC)(CCCC)CCCC.C(C)(C)(C)OC.[OH-].[Na+] | null | null | C=CCBr.COC(CNc1cnc(Cl)c(Cl)c1)OC>[Cl-].C[N+](CCCC)(CCCC)CCCC.C(C)(C)(C)OC.[OH-].[Na+]>C=CCN(CC(OC)OC)c1cnc(Cl)c(Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-767701720cf34de38245dfe493bdb5e8 | N[C@@H]1CN(c2cnc(Cl)c(Cl)c2)C[C@@H]1CO>>Clc1cc(N2C[C@@H]3CN[C@@H]3C2)cnc1Cl | [OH-].[Na+].N[C@H]1[C@H](CN(C1)C=1C=NC(=C(C1)Cl)Cl)CO.S(=O)(Cl)Cl.CN1C(CCC1)=O>>ClC=1C=C(C=NC1Cl)N1C[C@@H]2CN[C@@H]2C1 | O[CH2:8][C@H:7]1[CH2:6][N:5]([c:4]2[cH:3][c:2]([Cl:1])[c:14]([Cl:15])[n:13][cH:12]2)[CH2:11][C@H:10]1[NH2:9]>>[Cl:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][C@@H:7]3[CH2:8][NH:9][C@@H:10]3[CH2:11]2)[cH:12][n:13][c:14]1[Cl:15] | N[C@@H]1CN(c2cnc(Cl)c(Cl)c2)C[C@@H]1CO | Clc1cc(N2C[C@@H]3CN[C@@H]3C2)cnc1Cl | null | null | COCCOC | Heteroatom Alkylation and Arylation | OtherReaction | 5d35acc0b8f3b4b621b508209e76a9ce91ed7a09bd17af2e1e1b4523596d0b15 | 405fc0d288d595940df82750271ed5f4125713ca8b676b8ed83063765fec7c50 | c1cncc(N2C[C@@H]3CN[C@@H]3C2)c1 | O-[CH2;D2;+0:1]-[C:2]1-[C:3]-[#7:4]-[C:5]-[C:6]-1-[NH2;D1;+0:7]>>[#7:4]1-[C:5]-[C:6]2-[NH;D2;+0:7]-[CH2;D2;+0:1]-[C:2]-2-[C:3]-1 | null | [] | null | null | null | null | The treatment of Compound 6E with an acid such as hydrochloric acid under cooling conditions provides (allyl-5,6-dichloro-pyridin-3-yl)-amino)-acetaldehyde which when treated with 2-(S)-hydroxyamino-2-phenyl-ethanol and magnesium bromide in a solvent such as isopropyl alcohol provides (3S,4S)-2-[5-(5,6-dichloro-pyridin... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Primary amine | Secondary amine | null | C1[NH]C[C@H]2NC[C@@H]12 | c1ccncc1.C1[NH]C[C@H]2NC[C@@H]12 | HO- | COCCOC | null | null | N[C@@H]1CN(c2cnc(Cl)c(Cl)c2)C[C@@H]1CO>COCCOC>Clc1cc(N2C[C@@H]3CN[C@@H]3C2)cnc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c00a4082f0204f5caea99ef0143d335c | CC(C)(C)OC(=O)N1C[C@H]2CN(c3cnc(Cl)c(Cl)c3)C[C@H]21>>Clc1cc(N2C[C@@H]3CN[C@@H]3C2)cnc1Cl | ClC=1C=C(C=NC1Cl)N1C[C@@H]2CN([C@@H]2C1)C(=O)OC(C)(C)C.C1(=CC=CC=C1)S(=O)(=O)O>>C1(=CC=CC=C1)S(=O)(=O)O.ClC=1C=C(C=NC1Cl)N1C[C@@H]2CN[C@@H]2C1 | CC(C)(C)OC(=O)[N:9]1[CH2:8][C@H:7]2[CH2:6][N:5]([c:4]3[cH:3][c:2]([Cl:1])[c:14]([Cl:15])[n:13][cH:12]3)[CH2:11][C@H:10]21>>[Cl:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][C@@H:7]3[CH2:8][NH:9][C@@H:10]3[CH2:11]2)[cH:12][n:13][c:14]1[Cl:15] | CC(C)(C)OC(=O)N1C[C@H]2CN(c3cnc(Cl)c(Cl)c3)C[C@H]21 | Clc1cc(N2C[C@@H]3CN[C@@H]3C2)cnc1Cl | null | null | C(CC)O | Reduction | Boc amine deprotection | c91c139510b962eec8753afc23347f4b4d0eeb6c9d120e9798c55c78755a1e54 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1cncc(N2C[C@@H]3CN[C@@H]3C2)c1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-1-[C:5]-[#7:6]>>[#7:6]-[C:5]-[C:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-1 | 38.9 | [{"value": 38.9, "product": "C1(=CC=CC=C1)S(=O)(=O)O.ClC=1C=C(C=NC1Cl)N1C[C@@H]2CN[C@@H]2C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 2 | HOUR | Tert-butyl (1R,5S)-3-(5,6-dichloropyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane-6-carboxylate (642 mg) in 1-propanol (8 mL) was treated with benzenesulfonic acid (516 mg) and heated at 75° C. with stirring for 2 hours. The reaction mixture was cooled to room temperature, filtered, and the wetcake was dried in a vacuum o... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1[NH]C[C@H]2[NH]C[C@@H]12 | C1[NH]C[C@H]2NC[C@@H]12 | c1ccncc1.C1[NH]C[C@H]2NC[C@@H]12 | HO- | C(CC)O | 75 | 2 | CC(C)(C)OC(=O)N1C[C@H]2CN(c3cnc(Cl)c(Cl)c3)C[C@H]21>C(CC)O>Clc1cc(N2C[C@@H]3CN[C@@H]3C2)cnc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0ae8829a5a944635b7a4e768a0a6db5d | COC(CN)OC.O=C(OCc1ccccc1)ON1C(=O)CCC1=O>>COC(CNC(=O)OCc1ccccc1)OC | C(=O)(OCC1=CC=CC=C1)ON1C(=O)CCC1=O.C(C1=CC=CC=C1)OC(=O)ON1C(CCC1=O)=O.COC(CN)OC.C(C)N(CC)CC.O>>COC(CNC(OCC1=CC=CC=C1)=O)OC | [CH3:1][O:2][CH:3]([CH2:4][NH2:5])[O:16][CH3:17].O=C1CCC(=O)N1O[C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1>>[CH3:1][O:2][CH:3]([CH2:4][NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[O:16][CH3:17] | COC(CN)OC.O=C(OCc1ccccc1)ON1C(=O)CCC1=O | COC(CNC(=O)OCc1ccccc1)OC | null | null | C1(=CC=CC=C1)C | Protection | OtherReaction | 90f1cd2cfb4916c247fdb0b8c4bcd653fe37fb375d251f3afd49969111cee737 | f7ec1d72774a3155b06d1cf24e018b58f69117ddf4d9559df84efc3ecef0f4d7 | c1ccccc1 | O=C1-C-C-C(=O)-N-1-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4] | null | [] | 5 | CELSIUS | 15 | MINUTE | N-(Benzyloxycarbonyloxy)succinimide (74.5 Kg) was charged to a 200-gallon reactor, followed by toluene (235.1 Kg). The mixture was stirred for 15 minutes and cooled to 5° C. A solution of aminoacetaldehyde dimethylacetal (30 Kg) and triethylamine (28.9 Kg) in toluene (26.1 Kg) was charged slowly to the reactor over a 1... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Tertiary amide.Tertiary amide.Primary amine | Carbamic ester | C1CCNC1 | null | c1ccccc1 | HO- | C1(=CC=CC=C1)C | 5 | 0.25 | COC(CN)OC.O=C(OCc1ccccc1)ON1C(=O)CCC1=O>C1(=CC=CC=C1)C>COC(CNC(=O)OCc1ccccc1)OC |
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