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-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6b6484c542a4422eb9a68c56a12b0a18 | CC(C)CC(NCc1ccccc1CC(C(=O)OCC[Si](C)(C)C)N1C(=O)c2ccccc2C1=O)C(=O)OC(C)(C)C>>CC(C)CC(NCc1ccccc1CC(C(=O)O)N1C(=O)c2ccccc2C1=O)C(=O)OC(C)(C)C | [F-].C(CCC)[N+](CCCC)(CCCC)CCCC.O=C1N(C(C2=CC=CC=C12)=O)C(CC1=C(CNC(C(=O)OC(C)(C)C)CC(C)C)C=CC=C1)C(=O)OCC[Si](C)(C)C>>C(=O)(O)C(CC1=C(CNC(C(=O)OC(C)(C)C)CC(C)C)C=CC=C1)N1C(C2=CC=CC=C2C1=O)=O | C[Si](C)(C)CC[O:18][C:16]([CH:15]([CH2:14][c:13]1[c:8]([CH2:7][NH:6][CH:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[C:30](=[O:31])[O:32][C:33]([CH3:34])([CH3:35])[CH3:36])[cH:9][cH:10][cH:11][cH:12]1)[N:19]1[C:20](=[O:21])[c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]2[C:28]1=[O:29])=[O:17]>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH:5]([NH:6]... | CC(C)CC(NCc1ccccc1CC(C(=O)OCC[Si](C)(C)C)N1C(=O)c2ccccc2C1=O)C(=O)OC(C)(C)C | CC(C)CC(NCc1ccccc1CC(C(=O)O)N1C(=O)c2ccccc2C1=O)C(=O)OC(C)(C)C | null | null | O1CCCC1 | Deprotection | Ester saponification (alkyl deprotection) | a3c1e490feb6b7fce3c6323047260c78ad5d894f96ffb52fbe21f86a88668678 | 5b01c4b72bcb1d31e02ab060e26bc1888b853fee0b286003b9b19e22cf024145 | O=C1c2ccccc2C(=O)N1CCc1ccccc1 | C-[Si](-C)(-C)-C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 102.2 | [{"value": 102.2, "product": "C(=O)(O)C(CC1=C(CNC(C(=O)OC(C)(C)C)CC(C)C)C=CC=C1)N1C(C2=CC=CC=C2C1=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | Dissolve 2-{2-[2-(1,3-dioxo-1,3,dihydro-isoindol-2-yl)-2-(2-trimethylsilanyl-ethoxycarbonyl)-ethyl]-benzylamino}-4-methyl-valeric acid, tert-butyl ester (221 mg, 0.372 mmol) in tetrahydrofuran (5 mL) and treat with tetrabutylammonium fluoride (0.43 mL of a 1.0M solution in tetrahydrofuran, 0.43 mmol). Stir for 1.5 hour... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Silyl protective group | Carboxylic acid | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | Other | O1CCCC1 | null | 1.5 | CC(C)CC(NCc1ccccc1CC(C(=O)OCC[Si](C)(C)C)N1C(=O)c2ccccc2C1=O)C(=O)OC(C)(C)C>O1CCCC1>CC(C)CC(NCc1ccccc1CC(C(=O)O)N1C(=O)c2ccccc2C1=O)C(=O)OC(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d743b6dc42e449f9a5c576408807e9c4 | CC(C)CC(C(=O)OC(C)(C)C)N1Cc2ccccc2CC(NC(=O)C(Cc2ccccc2)SC(=O)c2ccccc2)C1=O>>CC(C)CC(C(=O)O)N1Cc2ccccc2CC(NC(=O)C(Cc2ccccc2)SC(=O)c2ccccc2)C1=O | C(C1=CC=CC=C1)(=O)SC(C(=O)NC1CC2=C(CN(C1=O)C(C(=O)OC(C)(C)C)CC(C)C)C=CC=C2)CC2=CC=CC=C2.C1(=CC=CC=C1)OC.FC(C(=O)O)(F)F>>C(C1=CC=CC=C1)(=O)SC(C(=O)NC1CC2=C(CN(C1=O)C(C(=O)O)CC(C)C)C=CC=C2)CC2=CC=CC=C2 | CC(C)(C)[O:8][C:6]([CH:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[N:9]1[CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[CH2:17][CH:18]([NH:19][C:20](=[O:21])[CH:22]([CH2:23][c:24]2[cH:25][cH:26][cH:27][cH:28][cH:29]2)[S:30][C:31](=[O:32])[c:33]2[cH:34][cH:35][cH:36][cH:37][cH:38]2)[C:39]1=[O:40])=[O:7]>>[CH3:1][CH:2]([CH3:3])... | CC(C)CC(C(=O)OC(C)(C)C)N1Cc2ccccc2CC(NC(=O)C(Cc2ccccc2)SC(=O)c2ccccc2)C1=O | CC(C)CC(C(=O)O)N1Cc2ccccc2CC(NC(=O)C(Cc2ccccc2)SC(=O)c2ccccc2)C1=O | null | null | C(Cl)Cl | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | O=C(SC(Cc1ccccc1)C(=O)NC1Cc2ccccc2CNC1=O)c1ccccc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 122.7 | [{"value": 122.7, "product": "C(C1=CC=CC=C1)(=O)SC(C(=O)NC1CC2=C(CN(C1=O)C(C(=O)O)CC(C)C)C=CC=C2)CC2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | Dissolve 2-[4-(2-benzoylsulfanyl-3-phenyl-propionyl-amino)-3-oxo-1,3,4,5-tetrahydro-benzo[c]azepin-2-yl]-4-methyl-valeric acid, tert-butyl ester (141 mg, 0.229 mmol) in methylene chloride (5 mL) and treat with anisole (0.12 mL, 1.15 mmol) then with trifluoroacetic acid (1.5M). Stir at room temperature for 15 hours, par... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | c1ccc2c(c1)CCC[NH]C2.c1ccccc1.c1ccccc1 | Other | C(Cl)Cl | null | 15 | CC(C)CC(C(=O)OC(C)(C)C)N1Cc2ccccc2CC(NC(=O)C(Cc2ccccc2)SC(=O)c2ccccc2)C1=O>C(Cl)Cl>CC(C)CC(C(=O)O)N1Cc2ccccc2CC(NC(=O)C(Cc2ccccc2)SC(=O)c2ccccc2)C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3307e69c593d48d58dc8fbd52835b144 | CC(C)CC(C(=O)O)N1Cc2ccccc2CC(NC(=O)C(Cc2ccccc2)SC(=O)c2ccccc2)C1=O>>CC(C)CC(C(=O)O)N1Cc2ccccc2CC(NC(=O)C(S)Cc2ccccc2)C1=O | C(C1=CC=CC=C1)(=O)SC(C(=O)NC1CC2=C(CN(C1=O)C(C(=O)O)CC(C)C)C=CC=C2)CC2=CC=CC=C2.Cl>>SC(C(=O)NC1CC2=C(CN(C1=O)C(C(=O)O)CC(C)C)C=CC=C2)CC2=CC=CC=C2 | O=C(c1ccccc1)[S:23][CH:22]([C:20]([NH:19][CH:18]1[CH2:17][c:16]2[c:11]([cH:12][cH:13][cH:14][cH:15]2)[CH2:10][N:9]([CH:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[C:6](=[O:7])[OH:8])[C:31]1=[O:32])=[O:21])[CH2:24][c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH:5]([C:6](=[O:7])[OH:8])[N:9]1[CH2:10][c... | CC(C)CC(C(=O)O)N1Cc2ccccc2CC(NC(=O)C(Cc2ccccc2)SC(=O)c2ccccc2)C1=O | CC(C)CC(C(=O)O)N1Cc2ccccc2CC(NC(=O)C(S)Cc2ccccc2)C1=O | null | null | CO | Reduction | OtherReaction | 3ad374f993c0dcc0c7bd535fc99990c89c5c9215cbb98c33afd4359fe55055ac | 18d802456fe85193570fdb3a00b25c8956a03b5a0210f708f961e42c1669d76e | O=C(CCc1ccccc1)NC1Cc2ccccc2CNC1=O | O=C(-[S;H0;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#7:6]-[C:7]-[C:8](=[O;D1;H0:9])-[#7:10])-c1:c:c:c:c:c:1>>[#7:10]-[C:8](=[O;D1;H0:9])-[C:7]-[#7:6]-[C:4](=[O;D1;H0:5])-[C:2](-[C:3])-[SH;D1;+0:1] | 80.8 | [{"value": 80.8, "product": "SC(C(=O)NC1CC2=C(CN(C1=O)C(C(=O)O)CC(C)C)C=CC=C2)CC2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.7, "product": "SC(C(=O)NC1CC2=C(CN(C1=O)C(C(=O)O)CC(C)C)C=CC=C2)CC2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Dissolve 2-[4-(2-benzoylsulfanyl-3-phenyl-propionyl-amino)-3-oxo-1,3,4,5-tetrahydro-benzo[c]azepin-2-yl]-4-methyl-valeric acid (0.229 mmol) in degassed methanol (3 mL) and cool in an ice bath. Treat with degassed 1N aqueous lithium hydroxide (1.0 mL) and stir, allowing the ice bath to warm gradually over 3 hours. With ... | 10.6084/m9.figshare.5104873.v1 | null | Carbo-thioester | Aliphatic thiol | c1ccccc1 | null | c1ccc2c(c1)CCC[NH]C2.c1ccccc1 | HO- | CO | null | null | CC(C)CC(C(=O)O)N1Cc2ccccc2CC(NC(=O)C(Cc2ccccc2)SC(=O)c2ccccc2)C1=O>CO>CC(C)CC(C(=O)O)N1Cc2ccccc2CC(NC(=O)C(S)Cc2ccccc2)C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6c4a508ae39645b5b1f65ea3b88e82b8 | CC(C)(C)OC(=O)NCC/C=C/c1cncnc1.CI>>CN(CC/C=C/c1cncnc1)C(=O)OC(C)(C)C | [H-].[Na+].C(C)(C)(C)OC(=O)NCC\C=C\C=1C=NC=NC1.IC.C(C)(C)NC(C)C>>CN(CC\C=C\C=1C=NC=NC1)C(=O)OC(C)(C)C | [NH:2]([CH2:3][CH2:4]/[CH:5]=[CH:6]/[c:7]1[cH:8][n:9][cH:10][n:11][cH:12]1)[C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19].I[CH3:1]>>[CH3:1][N:2]([CH2:3][CH2:4]/[CH:5]=[CH:6]/[c:7]1[cH:8][n:9][cH:10][n:11][cH:12]1)[C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19] | CC(C)(C)OC(=O)NCC/C=C/c1cncnc1.CI | CN(CC/C=C/c1cncnc1)C(=O)OC(C)(C)C | null | null | COCCOC.O.CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 29c841ae076cb6ee785aad2a4e3ce1a9b47357d7ad25657b8d9991b1347f5721 | c485eddcb40c5a0d396ffdb624041effa09ee4f5ca2ecce3fe13077cf65004ed | c1cncnc1 | I-[CH3;D1;+0:1].[C:2]=[C:3]/[C:4]-[C:5]-[NH;D2;+0:6]-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[C;D1;H3:13]>>[C:2]=[C:3]/[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH3;D1;+0:1])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[C;D1;H3:13] | 76.1 | [{"value": 76.1, "product": "CN(CC\\C=C\\C=1C=NC=NC1)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 45 | MINUTE | Under a nitrogen atmosphere, sodium hydride (0.78 g, 19.5 mmol, 60% dispersion in oil) was added to a stirring solution of IV (0.50 g, 2.0 mmol), 1,2-dimethoxyethane (20 mL), DMF (25 mL), and a trace of diisopropylamine. The mixture was stirred at ambient temperature for 45 min, and a solution of iodomethane (2.59 g, 1... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester | Carbamic ester | null | null | c1cncnc1 | HI | COCCOC.O.CN(C)C=O | null | 0.75 | CC(C)(C)OC(=O)NCC/C=C/c1cncnc1.CI>COCCOC.O.CN(C)C=O>CN(CC/C=C/c1cncnc1)C(=O)OC(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d7edba51f018489380d4a887b1e9b6d1 | BrC(Br)(Br)Br.O=Cc1cccnc1>>BrC(Br)=Cc1cccnc1 | BrC(Br)(Br)Br.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.N1=CC(=CC=C1)C=O>>BrC(=CC=1C=NC=CC1)Br | Br[C:2](Br)([Br:1])[Br:3].O=[CH:4][c:5]1[cH:6][cH:7][cH:8][n:9][cH:10]1>>[Br:1][C:2]([Br:3])=[CH:4][c:5]1[cH:6][cH:7][cH:8][n:9][cH:10]1 | BrC(Br)(Br)Br.O=Cc1cccnc1 | BrC(Br)=Cc1cccnc1 | null | null | C(Cl)Cl | C-C Coupling | OtherReaction | b27e55226bb2edd452ae488b95081b2b03421ee27be6c3935dbea4c7a5eeb5f6 | 695d5d1b30a064e72a7d907baf677e910730421b6580cc4e59d378cd6f0be898 | c1ccncc1 | Br-[C;H0;D4;+0:1](-Br)(-[Br;D1;H0:2])-[Br;D1;H0:3].O=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7]:[#7;a:8]:[c:9]>>[Br;D1;H0:2]-[C;H0;D3;+0:1](-[Br;D1;H0:3])=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7]:[#7;a:8]:[c:9] | 70 | [{"value": 70.0, "product": "BrC(=CC=1C=NC=CC1)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.0, "product": "BrC(=CC=1C=NC=CC1)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 45 | MINUTE | Tetrabromomethane (24.82 g, 0.747 mole) and triphenylphosphine (39.17 g, 0.149 mole) were stirred together in dry methylene chloride (100 mL) for 5 min. at 0° C. under a nitrogen atmosphere. To this mixture was added dropwise pyridine 3-carboxaldehyde (4 g, 0.0373 mole). The solution was then stirred for 45 min. at amb... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Aldehyde | Alkenyl halide.Alkenyl halide | null | null | c1ccncc1 | Br- | C(Cl)Cl | null | 0.75 | BrC(Br)(Br)Br.O=Cc1cccnc1>C(Cl)Cl>BrC(Br)=Cc1cccnc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-09f79ec740dc49de8727d8657531ecd2 | CN.OCCC#Cc1cccnc1>>CNCCC#Cc1cccnc1 | CN.N1=CC(=CC=C1)C#CCCO>>CNCCC#CC=1C=NC=CC1 | [CH3:1][NH2:2].O[CH2:3][CH2:4][C:5]#[C:6][c:7]1[cH:8][cH:9][cH:10][n:11][cH:12]1>>[CH3:1][NH:2][CH2:3][CH2:4][C:5]#[C:6][c:7]1[cH:8][cH:9][cH:10][n:11][cH:12]1 | CN.OCCC#Cc1cccnc1 | CNCCC#Cc1cccnc1 | null | null | O | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | 80c5fffb5a6cd9bcf0b3d20ee51fe5f6574f02d4cb5ea6a4d33b4a9098b0e672 | 405fc0d288d595940df82750271ed5f4125713ca8b676b8ed83063765fec7c50 | c1ccncc1 | O-[CH2;D2;+0:1]-[C:2]-[C:3]#[C:4]-[c:5]:[c:6]:[#7;a:7].[C;D1;H3:8]-[NH2;D1;+0:9]>>[#7;a:7]:[c:6]:[c:5]-[C:4]#[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:9]-[C;D1;H3:8] | 546.1 | [{"value": 546.1, "product": "CNCCC#CC=1C=NC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | An aqueous methylamine solution (5 mL, 40%, 58.7 mmole) was mixed with XII (200 mg, 0.08 mmole) and stirred for 3 hr. in a sealed tube at 45° C. After the reaction was complete, water (10 mL) was added to the cooled reaction mixture, and the reaction mixture was extracted with chloroform (10×5 mL). The combined organic... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Primary amine | Secondary amine | null | null | c1ccncc1 | HO- | O | null | 3 | CN.OCCC#Cc1cccnc1>O>CNCCC#Cc1cccnc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7ffeb21dee4c4bed8caf2b31d8aed738 | NCCc1ccc(O)c(O)c1.O=S(=O)(O)CCN1CCN(CCO)CC1.O=S(=O)(O)CCN1CCN(CCO)CC1>>CN1CCC[C@H]1c1cccnc1 | C1CN(CCN1CCO)CCS(=O)(=O)O.NCCC1=CC(O)=C(O)C=C1.C1CN(CCN1CCO)CCS(=O)(=O)O.NCCC1=CC(O)=C(O)C=C1>>N1=CC=CC(=C1)[C@H]1N(C)CCC1 | N[CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10](O)c(O)[cH:12]1.O=S(=O)(O)CCN1CC[N:11](CCO)CC1.O=S(=O)(O)CCN1CC[N:2]([CH2:1]CO)[CH2:3][CH2:4]1>>[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][C@H:6]1[c:7]1[cH:8][cH:9][cH:10][n:11][cH:12]1 | NCCc1ccc(O)c(O)c1.O=S(=O)(O)CCN1CCN(CCO)CC1.O=S(=O)(O)CCN1CCN(CCO)CC1 | CN1CCC[C@H]1c1cccnc1 | null | null | C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@]2([C@H]([C@@H]([C@H](O2)CO)O)O)CO)O)O)O)O | Heteroatom Alkylation and Arylation | OtherReaction | 19fc9a872b549396d811b42e2ef2bc61edfc6ad753a9b784038fcb2d26d8bd1b | 22424af31acac19f7bdb5717c7b71b423c8772246143962540fd1af6bf911444 | c1cncc([C@@H]2CCCN2)c1 | N-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[c;H0;D3;+0:6](-O):c(-O):[cH;D2;+0:7]:1.O-C-C-[N;H0;D3;+0:8]1-C-C-N(-C-C-S(-O)(=O)=O)-C-C-1.O-C-[CH2;D2;+0:9]-[N;H0;D3;+0:10]1-C-C-N(-C-C-S(-O)(=O)=O)-[CH2;D2;+0:11]-[C:12]-1>>[CH3;D1;+0:9]-[N;H0;D3;+0:10]1-[C:12]-[CH2;D2;+0:11]-[CH2;D2;+0:1]-[C@H;D3;+0:2]-1-[c:3]1:[c:4]... | null | [] | null | null | 10 | MINUTE | Dopamine release was measured by preparing synaptosomes from the striatal area of rat brain obtained from Sprague-Dawley rats generally according to the procedures set forth by Nagy et al., J. Neurochem., Vol. 43, pp. 1114-1123 (1984). Striata from 4 rats were homogenized in 2 ml of 0.32M sucrose buffered with 5 mM HEP... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Primary alcohol.Aromatic alcohol.Aromatic alcohol.Primary amine.Tertiary amine.Tertiary amine.Tertiary amine.Tertiary amine.Sulfonic acid.Sulfonic acid | Tertiary amine | c1ccccc1.C1CNCC[NH]1.C1CNCC[NH]1 | C1CC[NH]C1.c1ccncc1 | C1CC[NH]C1.c1ccncc1 | HO- | C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@]2([C@H]([C@@H]([C@H](O2)CO)O)O)CO)O)O)O)O | null | 0.166667 | NCCc1ccc(O)c(O)c1.O=S(=O)(O)CCN1CCN(CCO)CC1.O=S(=O)(O)CCN1CCN(CCO)CC1>C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@]2([C@H]([C@@H]([C@H](O2)CO)O)O)CO)O)O)O)O>CN1CCC[C@H]1c1cccnc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6f8a65c0c7a247018b76537d1c75a375 | N#Cc1ccc(CBr)cc1.O=C1NCCN1>>N#Cc1ccc(CN2CCN(Cc3ccc(C#N)cc3)C2=O)cc1 | O.BrCC1=CC=C(C#N)C=C1.[H-].[Na+].N1C(NCC1)=O>>O=C1N(CCN1CC1=CC=C(C#N)C=C1)CC1=CC=C(C#N)C=C1 | Br[CH2:7][c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:24][cH:23]1.[NH:8]1[CH2:9][CH2:15][NH:11][C:21]1=[O:22]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]2[CH2:9][CH2:10][N:11]([CH2:12][c:13]3[cH:14][cH:15][c:16]([C:17]#[N:18])[cH:19][cH:20]3)[C:21]2=[O:22])[cH:23][cH:24]1 | N#Cc1ccc(CBr)cc1.O=C1NCCN1 | N#Cc1ccc(CN2CCN(Cc3ccc(C#N)cc3)C2=O)cc1 | null | null | CN(C=O)C | Aromatic Heterocycle Formation | OtherReaction | 39571f641692bae0ab2e4fb7e56baf0a046bbe68e5d15065d8f936b61702d85c | 04064b000c1f037cb6379c4a9b891971302bcd094d2302ea56061b3b37327222 | O=C1N(Cc2ccccc2)CCN1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[NH;D2;+0:7]-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[NH;D2;+0:10]-1>>[C:11]-[c:12](:[c:13]):[cH;D2;+0:8]:[c:14]:[c:15]-[C:16]-[N;H0;D3;+0:7]1-[C:17]-[CH2;D2;+0:9]-[N;H0;D3;+0:10](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:6]-1=[O;D1;H0:5] | null | [] | null | null | 1 | HOUR | To sodium hydride (2.4 g, 60 mmol) in dimethylformamide (50 mL) at 0° C. was added imidazolin-2-one (2.6 g, 30 mmol). After stirring for 20 minutes 4-(bromomethyl)benzonitrile (13 g, 66 mmol) was added and the mixture was warmed to ambient temperature. After stirring for 1 hour the reaction was poured into water and a ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Urea | Urea.Nitrile | C1CNCN1 | C1C[NH]C[NH]1.c1ccccc1 | c1ccccc1.C1C[NH]C[NH]1.c1ccccc1 | Br- | CN(C=O)C | null | 1 | N#Cc1ccc(CBr)cc1.O=C1NCCN1>CN(C=O)C>N#Cc1ccc(CN2CCN(Cc3ccc(C#N)cc3)C2=O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4eef7a1f326e44c69373eeaaece2675b | CN(C)c1ccc(C(O)C(=O)c2ccccc2)cc1.NC(N)=O>>CN(C)c1ccc(-c2[nH]c(=O)[nH]c2-c2ccccc2)cc1 | NC(=O)N.CN(C1=CC=C(C=C1)C(C(=O)C1=CC=CC=C1)O)C>>CN(C1=CC=C(C=C1)C=1NC(NC1C1=CC=CC=C1)=O)C | O=[C:13]([CH:8](O)[c:7]1[cH:6][cH:5][c:4]([N:2]([CH3:1])[CH3:3])[cH:21][cH:20]1)[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.[NH2:9][C:10](=[O:11])[NH2:12]>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[nH:9][c:10](=[O:11])[nH:12][c:13]2-[c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[cH:20][cH:21]1 | CN(C)c1ccc(C(O)C(=O)c2ccccc2)cc1.NC(N)=O | CN(C)c1ccc(-c2[nH]c(=O)[nH]c2-c2ccccc2)cc1 | null | null | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 7a04490902783a9d1d6099ad78b95538301d0ef7b8b6cc364284d393dbdf37cd | 19da97726e6dc44d537eff971a50046c3e80ca62fdecca0b64533a3c10927d47 | O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)[nH]1 | O-[CH;D3;+0:1](-[C;H0;D3;+0:2](=O)-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7])-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12].[NH2;D1;+0:13]-[C;H0;D3;+0:14](-[NH2;D1;+0:15])=[O;D1;H0:16]>>[O;D1;H0:16]=[c;H0;D3;+0:14]1:[nH;D2;+0:13]:[c;H0;D3;+0:2](-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7]):[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:... | null | [] | 120 | CELSIUS | 2 | HOUR | To acetic acid (2 mL) was added urea (0.6 g, 10 mmol) and 2-(4-dimethylaminophenyl)-2-hydroxy-1-phenylethanone (2.6 g, 10 mmol). After stirring for 2 hours at 120° C., the reaction was cooled to ambient temperature. The resulting solid was filtered, washed with ether, and dried in vacuo to give 4-(4-dimethylaminophenyl... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Urea.Secondary alcohol | null | null | c1c[nH]cn1 | c1ccccc1.c1c[nH]cn1.c1ccccc1 | HO- | C(C)(=O)O | 120 | 2 | CN(C)c1ccc(C(O)C(=O)c2ccccc2)cc1.NC(N)=O>C(C)(=O)O>CN(C)c1ccc(-c2[nH]c(=O)[nH]c2-c2ccccc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-48581d9a191c4e318c4956285de6cfaf | N#Cc1cccc(CBr)c1.O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)[nH]1>>N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1 | C1(=CC=CC=C1)C=1NC(NC1C1=CC=CC=C1)=O.BrCC=1C=C(C#N)C=CC1.[H-].[Na+]>>C1(=CC=CC=C1)C=1NC(N(C1C1=CC=CC=C1)CC=1C=C(C#N)C=CC1)=O | Br[CH2:8][c:7]1[cH:6][cH:5][cH:4][c:3]([C:2]#[N:1])[cH:27]1.[nH:9]1[c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[nH:24][c:25]1=[O:26]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][n:9]2[c:10](-[c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[c:17](-[c:18]3[cH:1... | N#Cc1cccc(CBr)c1.O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)[nH]1 | N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b9d84e1ee028da6e8c5d8924d45fbf8f3755d9adc2caf0035bd5ed7f30f5ee03 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)n1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[c:6]1:[#7;a:7]:[c:8](-[c:9]):[c:10](-[c:11]):[nH;D2;+0:12]:1>>[O;D1;H0:5]=[c:6]1:[#7;a:7]:[c:8](-[c:9]):[c:10](-[c:11]):[n;H0;D3;+0:12]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | In a manner similar to Preparation 1 above, 2,3-dihydro-4,5-diphenyl-1H-imidazol-2-one (1.2 g, 5 mmol) was reacted with 3-(bromomethyl)benzonitrile (0.39 g, 2 mmol) and sodium hydride (0.18 g, 5 mmol) in dimethylformamide (20 mL) to give 3-[(2,3-dihydro-4,5-diphenyl-2-oxo-1H-imidazol-1-yl)methyl]benzonitrile after chro... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[nH]cn1 | c1ccccc1.c1ccccc1.c1ccccc1.c1c[nH]cn1 | HBr | CN(C=O)C | null | null | N#Cc1cccc(CBr)c1.O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)[nH]1>CN(C=O)C>N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8cacee1477ef4c929f9e4b44523e47a4 | COC(=O)c1cccc(CBr)c1.O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)[nH]1>>COC(=O)c1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1 | Cl.C1(=CC=CC=C1)C=1NC(NC1C1=CC=CC=C1)=O.[H-].[Na+].BrCC=1C=C(C(=O)OC)C=CC1>>COC(=O)C=1C=C(C=CC1)CN1C(NC(=C1C1=CC=CC=C1)C1=CC=CC=C1)=O | Br[CH2:10][c:9]1[cH:8][cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:29]1.[nH:11]1[c:12](-[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[c:19](-[c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[nH:26][c:27]1=[O:28]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([CH2:10][n:11]2[c:12](-[c:13]3[cH:14][cH:15][cH:16][cH:... | COC(=O)c1cccc(CBr)c1.O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)[nH]1 | COC(=O)c1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b9d84e1ee028da6e8c5d8924d45fbf8f3755d9adc2caf0035bd5ed7f30f5ee03 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)n1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[c:6]1:[#7;a:7]:[c:8](-[c:9]):[c:10](-[c:11]):[nH;D2;+0:12]:1>>[O;D1;H0:5]=[c:6]1:[#7;a:7]:[c:8](-[c:9]):[c:10](-[c:11]):[n;H0;D3;+0:12]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 25 | [{"value": 25.0, "product": "COC(=O)C=1C=C(C=CC1)CN1C(NC(=C1C1=CC=CC=C1)C1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 30 | MINUTE | To 2,3-dihydro-4,5-diphenyl-1H-imidazol-2-one (4.76 g, 20 mmol) in 50 mL DMF was added to a suspension of NaH (0.8 g, 20 mmol) in 25 mL DMF. The suspension was stirred at ambient temperatures for 30 minutes, then heated to 50° C. for 30 minutes. A solution of methyl 3-bromomethylbenzoate (2.86 g, 12.5 mmol) in 20 mL DM... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[nH]cn1 | c1ccccc1.c1ccccc1.c1ccccc1.c1c[nH]cn1 | HBr | CN(C)C=O | 50 | 0.5 | COC(=O)c1cccc(CBr)c1.O=c1[nH]c(-c2ccccc2)c(-c2ccccc2)[nH]1>CN(C)C=O>COC(=O)c1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5a2a11c5b78a483ca185dc9908165691 | N#Cc1ccc2ccc(CBr)cc2c1.N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1>>N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)n(Cc3ccc4ccc(C#N)cc4c3)c2=O)c1 | C1(=CC=CC=C1)C=1NC(N(C1C1=CC=CC=C1)CC=1C=C(C#N)C=CC1)=O.BrCC1=CC=C2C=CC(=CC2=C1)C#N>>C(#N)C=1C=C(C=CC1)CN1C(N(C(=C1C1=CC=CC=C1)C1=CC=CC=C1)CC1=CC=C2C=CC(=CC2=C1)C#N)=O | Br[CH2:25][c:26]1[cH:27][cH:28][c:29]2[cH:30][cH:31][c:32]([C:33]#[N:34])[cH:35][c:36]2[cH:37]1.[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][n:9]2[c:10](-[c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[c:17](-[c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[nH:24][c:38]2=[O:39])[cH:40]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6... | N#Cc1ccc2ccc(CBr)cc2c1.N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1 | N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)n(Cc3ccc4ccc(C#N)cc4c3)c2=O)c1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b9d84e1ee028da6e8c5d8924d45fbf8f3755d9adc2caf0035bd5ed7f30f5ee03 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1n(Cc2ccccc2)c(-c2ccccc2)c(-c2ccccc2)n1Cc1ccc2ccccc2c1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#7;a:6]1:[c:7](-[c:8]):[c:9](-[c:10]):[nH;D2;+0:11]:[c:12]:1=[O;D1;H0:13]>>[C:5]-[#7;a:6]1:[c:7](-[c:8]):[c:9](-[c:10]):[n;H0;D3;+0:11](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:12]:1=[O;D1;H0:13] | null | [] | null | null | null | null | In a manner similar to Preparation 2 above, 3-[(2,3-dihydro-4,5-diphenyl-2-oxo-1H-imidazol-1-yl)methyl]benzonitrile was reacted with 7-(bromomethyl)naphthalene-2-carbonitrile to give 7-[[3-(3-cyanophenyl)methyl-2,3-dihydro-4,5-diphenyl-2-oxo-1H-imidazol-1-yl]methyl]naphthalene-2-carbonitrile; NMR (CDCl3) 8.05 (s,1), 7.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[nH]cn1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2ccccc2c1.c1c[nH]cn1 | HBr | null | null | null | N#Cc1ccc2ccc(CBr)cc2c1.N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)[nH]c2=O)c1>>N#Cc1cccc(Cn2c(-c3ccccc3)c(-c3ccccc3)n(Cc3ccc4ccc(C#N)cc4c3)c2=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-28db859784404afd8675d326cead07a5 | C1COCCN1.CCCCC(=O)Nc1ccc(C(=O)O)cc1[N+](=O)[O-]>>CCCCC(=O)Nc1ccc(C(=O)N2CCOCC2)cc1[N+](=O)[O-] | N1CCOCC1.[N+](=O)([O-])C=1C=C(C(=O)O)C=CC1NC(CCCC)=O.C1(CCCCC1)N=C=NC1CCCCC1.ON1N=NC2=C1C=CC=C2>>[N+](=O)([O-])C=1C=C(C(=O)N2CCOCC2)C=CC1NC(CCCC)=O | [NH:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1.O[C:12]([c:11]1[cH:10][cH:9][c:8]([NH:7][C:5]([CH2:4][CH2:3][CH2:2][CH3:1])=[O:6])[c:21]([N+:22](=[O:23])[O-:24])[cH:20]1)=[O:13]>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][c:11]([C:12](=[O:13])[N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)[cH:20... | C1COCCN1.CCCCC(=O)Nc1ccc(C(=O)O)cc1[N+](=O)[O-] | CCCCC(=O)Nc1ccc(C(=O)N2CCOCC2)cc1[N+](=O)[O-] | null | null | O1CCCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | 2ef483949e7ba3e5f888cf14cdce25fa611f75be09fdf1854a473be519821b59 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1ccccc1)N1CCOCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#8:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#8:6]-[C:11]-[C:10]-1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | 15 | MINUTE | In tetrahydrofuran (800 ml), 3-nitro-4-valeramidobenzoic acid ([1]-(11)-1) (20.0 g) was dissolved. Dicyclohexylcarbodiimide (17.1 g) and 1-hydroxybenzotriazole (11.2 g) were added to the solution, and the mixture was stirred at room temperature for 15 minutes. Morpholine (7.27 g) was further added to the solution. The ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1COCCN1 | C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1 | HO- | O1CCCC1 | null | 0.25 | C1COCCN1.CCCCC(=O)Nc1ccc(C(=O)O)cc1[N+](=O)[O-]>O1CCCC1>CCCCC(=O)Nc1ccc(C(=O)N2CCOCC2)cc1[N+](=O)[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d355d2b6749d4fb59a2aefb995bcd837 | BrCc1ccc(-c2ccccc2-c2nnnn2C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1.C1COCCN1.O=C(O)c1ccc([N+](=O)[O-])c(O)c1>>O=C(c1ccc([N+](=O)[O-])c(OCc2ccc(-c3ccccc3-c3nnnn3C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2)c1)N1CCOCC1 | O.[H-].[Na+].N1CCOCC1.OC=1C=C(C(=O)O)C=CC1[N+](=O)[O-].C1(=CC=CC=C1)C(N1N=NN=C1C1=C(C=CC=C1)C1=CC=C(C=C1)CBr)(C1=CC=CC=C1)C1=CC=CC=C1>>C1(=CC=CC=C1)C(N1N=NN=C1C1=C(C=CC=C1)C1=CC=C(C=C1)COC=1C=C(C(=O)N2CCOCC2)C=CC1[N+](=O)[O-])(C1=CC=CC=C1)C1=CC=CC=C1 | Br[CH2:12][c:13]1[cH:14][cH:15][c:16](-[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2-[c:23]2[n:24][n:25][n:26][n:27]2[C:28]([c:29]2[cH:30][cH:31][cH:32][cH:33][cH:34]2)([c:35]2[cH:36][cH:37][cH:38][cH:39][cH:40]2)[c:41]2[cH:42][cH:43][cH:44][cH:45][cH:46]2)[cH:47][cH:48]1.[NH:50]1[CH2:51][CH2:52][O:53][CH2:54][CH2:55]1.O[... | BrCc1ccc(-c2ccccc2-c2nnnn2C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1.C1COCCN1.O=C(O)c1ccc([N+](=O)[O-])c(O)c1 | O=C(c1ccc([N+](=O)[O-])c(OCc2ccc(-c3ccccc3-c3nnnn3C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2)c1)N1CCOCC1 | null | null | CN(C=O)C | Acylation | OtherReaction | e1b8498ef40a5ada9c8073cd0aaefc1cbd3944b85096db8e8382b94b4f0c8207 | 702e687068298bcd1761113687349ebe151efaa2492f97e1b3e4f8fd84cb22e4 | O=C(c1cccc(OCc2ccc(-c3ccccc3-c3nnnn3C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2)c1)N1CCOCC1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].O-[C;H0;D3;+0:5](=[O;D1;H0:6])-[c:7](:[c:8]):[c:9]:[c:10](-[OH;D1;+0:11]):[c:12].[#8:13]1-[C:14]-[C:15]-[NH;D2;+0:16]-[C:17]-[C:18]-1>>[O;D1;H0:6]=[C;H0;D3;+0:5](-[N;H0;D3;+0:16]1-[C:15]-[C:14]-[#8:13]-[C:18]-[C:17]-1)-[c:7](:[c:8]):[c:9]:[c:10](-[O;H0;D2;+0:11]-[CH2;D2;+0:1]-[c:2](... | 101.9 | [{"value": 101.9, "product": "C1(=CC=CC=C1)C(N1N=NN=C1C1=C(C=CC=C1)C1=CC=C(C=C1)COC=1C=C(C(=O)N2CCOCC2)C=CC1[N+](=O)[O-])(C1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | The compound ([3]-(32)-587) (0.99 g) prepared in Example 36 was dissolved in dry N,N-dimethylformamide (19 ml), and 50% sodium hydride (0.20 g) was added to the solution. The mixture was stirred at room temperature for 15 minutes. A solution of N-(triphenylmethyl)-5-[4'-(bromomethyl)biphenyl-2-yl]tetrazole (2.19 g) in ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid.Aromatic alcohol.Secondary amine | Ether.Tertiary amide | C1COCCN1 | C1COCC[NH]1 | c1ccccc1.c1ccccc1.c1ccccc1.c1nnn[nH]1.c1ccccc1.c1ccccc1.c1ccccc1.C1COCC[NH]1 | HBr | CN(C=O)C | null | 0.25 | BrCc1ccc(-c2ccccc2-c2nnnn2C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1.C1COCCN1.O=C(O)c1ccc([N+](=O)[O-])c(O)c1>CN(C=O)C>O=C(c1ccc([N+](=O)[O-])c(OCc2ccc(-c3ccccc3-c3nnnn3C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2)c1)N1CCOCC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5a1f4fa16f264e7fb02a9d9377895d83 | O=C(c1ccc([N+](=O)[O-])c(OCc2ccc(-c3ccccc3-c3nnnn3C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2)c1)N1CCOCC1>>Nc1ccc(C(=O)N2CCOCC2)cc1OCc1ccc(-c2ccccc2-c2nnnn2C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | C1(=CC=CC=C1)C(N1N=NN=C1C1=C(C=CC=C1)C1=CC=C(C=C1)COC=1C=C(C(=O)N2CCOCC2)C=CC1[N+](=O)[O-])(C1=CC=CC=C1)C1=CC=CC=C1.C(C)O.O.NN>>C1(=CC=CC=C1)C(N1N=NN=C1C1=C(C=CC=C1)C1=CC=C(C=C1)COC=1C=C(C(=O)N2CCOCC2)C=CC1N)(C1=CC=CC=C1)C1=CC=CC=C1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[cH:14][c:15]1[O:16][CH2:17][c:18]1[cH:19][cH:20][c:21](-[c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]2-[c:28]2[n:29][n:30][n:31][n:32]2[C:33]([c:34]2[cH:35][cH:36][cH:37][cH:38][cH:39]2)([c:40]2[cH:41][cH:42][cH:43][cH:44][cH:4... | O=C(c1ccc([N+](=O)[O-])c(OCc2ccc(-c3ccccc3-c3nnnn3C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2)c1)N1CCOCC1 | Nc1ccc(C(=O)N2CCOCC2)cc1OCc1ccc(-c2ccccc2-c2nnnn2C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | null | [Pd] | C(C)(=O)OCC | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(c1cccc(OCc2ccc(-c3ccccc3-c3nnnn3C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2)c1)N1CCOCC1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 116.5 | [{"value": 116.5, "product": "C1(=CC=CC=C1)C(N1N=NN=C1C1=C(C=CC=C1)C1=CC=C(C=C1)COC=1C=C(C(=O)N2CCOCC2)C=CC1N)(C1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 1 | HOUR | A solution of the compound ([3]-(33)-587) (0.60 g) prepared in Example 37, ethanol (150 ml), and ethyl acetate (40 ml) was stirred at 70° C. for 15 minutes. After 10% Pd/C (0.10 g) and hydrazine monohydrate (1 ml) were added to the solution, the mixture was stirred at 70° C. for 1 hour. The insolubles were filtered thr... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.C1COCC[NH]1.c1ccccc1.c1ccccc1.c1nnn[nH]1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | [Pd].C(C)(=O)OCC | 70 | 1 | O=C(c1ccc([N+](=O)[O-])c(OCc2ccc(-c3ccccc3-c3nnnn3C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2)c1)N1CCOCC1>[Pd].C(C)(=O)OCC>Nc1ccc(C(=O)N2CCOCC2)cc1OCc1ccc(-c2ccccc2-c2nnnn2C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-72f20e5a16b14b8398629965aa0bea7a | CCCCC(=O)Cl.Nc1ccc(C(=O)N2CCOCC2)cc1OCc1ccc(-c2ccccc2-c2nnnn2C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1>>CCCCC(=O)Nc1ccc(C(=O)N2CCOCC2)cc1OCc1ccc(-c2ccccc2-c2nnnn2C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | C1(=CC=CC=C1)C(N1N=NN=C1C1=C(C=CC=C1)C1=CC=C(C=C1)COC=1C=C(C(=O)N2CCOCC2)C=CC1N)(C1=CC=CC=C1)C1=CC=CC=C1.C(CCCC)(=O)Cl.O>>C1(=CC=CC=C1)C(N1N=NN=C1C1=C(C=CC=C1)C1=CC=C(C=C1)COC=1C=C(C(=O)N2CCOCC2)C=CC1NC(CCCC)=O)(C1=CC=CC=C1)C1=CC=CC=C1 | Cl[C:5]([CH2:4][CH2:3][CH2:2][CH3:1])=[O:6].[NH2:7][c:8]1[cH:9][cH:10][c:11]([C:12](=[O:13])[N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)[cH:20][c:21]1[O:22][CH2:23][c:24]1[cH:25][cH:26][c:27](-[c:28]2[cH:29][cH:30][cH:31][cH:32][c:33]2-[c:34]2[n:35][n:36][n:37][n:38]2[C:39]([c:40]2[cH:41][cH:42][cH:43][cH:44][cH:45]... | CCCCC(=O)Cl.Nc1ccc(C(=O)N2CCOCC2)cc1OCc1ccc(-c2ccccc2-c2nnnn2C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | CCCCC(=O)Nc1ccc(C(=O)N2CCOCC2)cc1OCc1ccc(-c2ccccc2-c2nnnn2C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | null | CN(C1=CC=NC=C1)C | N1=CC=CC=C1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(c1cccc(OCc2ccc(-c3ccccc3-c3nnnn3C(c3ccccc3)(c3ccccc3)c3ccccc3)cc2)c1)N1CCOCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | 2 | HOUR | The compound ([3]-(34)-587) (0.07 g) prepared in Example 38 and 4-dimethylaminopyridine (0.01 g) were dissolved in dry pyridine (1 ml). Valeryl chloride (0.043 g) was added dropwise by a syringe while cooling on ice. The mixture was stirred at room temperature for 2 hours, then, poured into water (20 ml), extracted wit... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.C1COCC[NH]1.c1ccccc1.c1ccccc1.c1nnn[nH]1.c1ccccc1.c1ccccc1.c1ccccc1 | HCl | CN(C1=CC=NC=C1)C.N1=CC=CC=C1 | null | 2 | CCCCC(=O)Cl.Nc1ccc(C(=O)N2CCOCC2)cc1OCc1ccc(-c2ccccc2-c2nnnn2C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1>CN(C1=CC=NC=C1)C.N1=CC=CC=C1>CCCCC(=O)Nc1ccc(C(=O)N2CCOCC2)cc1OCc1ccc(-c2ccccc2-c2nnnn2C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9c42e3fc562e485b97a64b0a8e60149a | C1COCCN1.Nc1ccc(C(=O)O)cc1[N+](=O)[O-]>>Nc1ccc(C(=O)N2CCOCC2)cc1[N+](=O)[O-] | NC1=C(C=C(C(=O)O)C=C1)[N+](=O)[O-].ON1N=NC2=C1C=CC=C2.C1(CCCCC1)N=C=NC1CCCCC1.N1CCOCC1>>NC1=C(C=C(C(=O)N2CCOCC2)C=C1)[N+](=O)[O-] | [NH:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1.O[C:6]([c:5]1[cH:4][cH:3][c:2]([NH2:1])[c:15]([N+:16](=[O:17])[O-:18])[cH:14]1)=[O:7]>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[cH:14][c:15]1[N+:16](=[O:17])[O-:18] | C1COCCN1.Nc1ccc(C(=O)O)cc1[N+](=O)[O-] | Nc1ccc(C(=O)N2CCOCC2)cc1[N+](=O)[O-] | null | null | CN(C=O)C | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | 2ef483949e7ba3e5f888cf14cdce25fa611f75be09fdf1854a473be519821b59 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1ccccc1)N1CCOCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#8:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:10]-[C:11]-[#8:6]-[C:7]-[C:8]-1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | 2 | HOUR | A mixture of 4-amino-3-nitrobenzoic acid (7.40 g), 1-hydroxybenzotriazole (6.59 g), dicyclohexylcarbodiimide (10.90 g), dry N,N-dimethylformamide (74 ml), and morpholine (4.3 ml) was stirred at room temperature for 2 hours. The insolubles were filtered out, and washed with N,N-dimethylformamide. The filtrate and the wa... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1COCCN1 | C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1 | HO- | CN(C=O)C | null | 2 | C1COCCN1.Nc1ccc(C(=O)O)cc1[N+](=O)[O-]>CN(C=O)C>Nc1ccc(C(=O)N2CCOCC2)cc1[N+](=O)[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-afe1acea3c9c4770b2b372a33f6672d6 | CCCCC(=O)Cl.COC(=O)c1cccc(N)c1>>CCCCC(=O)Nc1cccc(C(=O)OC)c1 | N1=CC=CC=C1.NC=1C=C(C(=O)OC)C=CC1.C(CCCC)(=O)Cl>>C(CCCC)(=O)NC=1C=C(C(=O)OC)C=CC1 | Cl[C:5]([CH2:4][CH2:3][CH2:2][CH3:1])=[O:6].[NH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]([C:13](=[O:14])[O:15][CH3:16])[cH:17]1>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][cH:11][c:12]([C:13](=[O:14])[O:15][CH3:16])[cH:17]1 | CCCCC(=O)Cl.COC(=O)c1cccc(N)c1 | CCCCC(=O)Nc1cccc(C(=O)OC)c1 | null | null | O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | 4 | HOUR | To anhydrous pyridine (120 ml), methyl 3-aminobenzoate (5.00 g) was dissolved, and valeryl chloride (4.13 ml) was added while cooling on ice. The mixture was stirred at room temperature for 4 hours. Distilled water was added to the solution. The whole was extracted with ethyl acetate, washed with 5% sodium hydrogencarb... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1 | HCl | O | null | 4 | CCCCC(=O)Cl.COC(=O)c1cccc(N)c1>O>CCCCC(=O)Nc1cccc(C(=O)OC)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d4473f302a7441cbb178c086184f7270 | CCCCCCc1ccc(C(=O)N2CCOCC2)cc1[N+](=O)[O-]>>CCCCCCc1ccc(C(=O)N2CCOCC2)cc1N | C(CCCCC)C1=C(C=C(C(=O)N2CCOCC2)C=C1)[N+](=O)[O-].O.NN>>NC=1C=C(C(=O)N2CCOCC2)C=CC1CCCCCC | O=[N+:21]([O-])[c:20]1[c:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:8][cH:9][c:10]([C:11](=[O:12])[N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)[cH:19]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)[cH:19][c:20]1[NH2:21] | CCCCCCc1ccc(C(=O)N2CCOCC2)cc1[N+](=O)[O-] | CCCCCCc1ccc(C(=O)N2CCOCC2)cc1N | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(c1ccccc1)N1CCOCC1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 99.4 | [{"value": 99.4, "product": "NC=1C=C(C(=O)N2CCOCC2)C=CC1CCCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 30 | MINUTE | The compound ([5]-(54)-75) (700 mg) prepared in Example 62 was dissolved in ethanol (35 ml). After the solution was heated to 50° C., a suspension of 10% Pd/C (70 mg) in ethanol was added, and hydrazine monohydrate (0.35 ml) was added to the solution. The solution was stirred at 50° C. for 30 minutes. After the reactio... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.C1COCC[NH]1 | Other | [Pd].C(C)O | 50 | 0.5 | CCCCCCc1ccc(C(=O)N2CCOCC2)cc1[N+](=O)[O-]>[Pd].C(C)O>CCCCCCc1ccc(C(=O)N2CCOCC2)cc1N |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-20fb073b44614d5f8991584cce60fb11 | CCCCCCc1ccc(C(=O)N2CCOCC2)cc1N.COC(=O)c1ccc(C=O)cc1>>CCCCCCc1ccc(C(=O)N2CCOCC2)cc1NCc1ccc(C(=O)OC)cc1 | O.COC(=O)C1=CC=C(C=O)C=C1.NC=1C=C(C(=O)N2CCOCC2)C=CC1CCCCCC>>C(CCCCC)C1=C(C=C(C(=O)N2CCOCC2)C=C1)NCC1=CC=C(C=C1)C(=O)OC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)[cH:19][c:20]1[NH2:21].O=[CH:22][c:23]1[cH:24][cH:25][c:26]([C:27](=[O:28])[O:29][CH3:30])[cH:31][cH:32]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[N... | CCCCCCc1ccc(C(=O)N2CCOCC2)cc1N.COC(=O)c1ccc(C=O)cc1 | CCCCCCc1ccc(C(=O)N2CCOCC2)cc1NCc1ccc(C(=O)OC)cc1 | null | null | C(C)(=O)O | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | O=C(c1cccc(NCc2ccccc2)c1)N1CCOCC1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[NH;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8] | null | [] | null | null | 4 | HOUR | The compound ([5]-(55)-75) (600 mg) prepared in Example 63 was dissolved in acetic acid (6.0 ml). Then, 4-methoxycarbonylbenzaldehyde (373 mg) was added. The mixture was stirred at room temperature for 4 hours. Then, boranediethylamine complex (146 mg) was added to the solution. The mixture was stirred at room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.C1COCC[NH]1.c1ccccc1 | Other | C(C)(=O)O | null | 4 | CCCCCCc1ccc(C(=O)N2CCOCC2)cc1N.COC(=O)c1ccc(C=O)cc1>C(C)(=O)O>CCCCCCc1ccc(C(=O)N2CCOCC2)cc1NCc1ccc(C(=O)OC)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0fecae8b671b4957a472ce0b500305f7 | C1COCCN1.Cc1ccc(C(=O)O)cc1[N+](=O)[O-]>>Cc1ccc(C(=O)N2CCOCC2)cc1[N+](=O)[O-] | ON1N=NC2=C1C=CC=C2.Cl.C(C)N=C=NCCCN(C)C.N1CCOCC1.CC1=C(C=C(C(=O)O)C=C1)[N+](=O)[O-]>>CC1=C(C=C(C(=O)N2CCOCC2)C=C1)[N+](=O)[O-] | [NH:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1.O[C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:15]([N+:16](=[O:17])[O-:18])[cH:14]1)=[O:7]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[cH:14][c:15]1[N+:16](=[O:17])[O-:18] | C1COCCN1.Cc1ccc(C(=O)O)cc1[N+](=O)[O-] | Cc1ccc(C(=O)N2CCOCC2)cc1[N+](=O)[O-] | null | null | CN(C)C=O.O.C(C)N(CC)CC | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | 2ef483949e7ba3e5f888cf14cdce25fa611f75be09fdf1854a473be519821b59 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1ccccc1)N1CCOCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#8:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:10]-[C:11]-[#8:6]-[C:7]-[C:8]-1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | 4 | HOUR | The compound ([5]-(53)-278) (6.5272 g) prepared in Example 72 was dissolved in anhydrous DMF (98 ml). Then, 1-hydroxybenzotriazole (6.3297 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (8.9795 g), triethylamine (6.5 ml), and morpholine (4.1 ml) were added to the solution. The mixture was stirred at ro... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1COCCN1 | C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1 | HO- | CN(C)C=O.O.C(C)N(CC)CC | null | 4 | C1COCCN1.Cc1ccc(C(=O)O)cc1[N+](=O)[O-]>CN(C)C=O.O.C(C)N(CC)CC>Cc1ccc(C(=O)N2CCOCC2)cc1[N+](=O)[O-] |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-92408f87220947e8aa462aa1b48b9d43 | C1COCCN1.O=C(O)c1cccc([N+](=O)[O-])c1>>O=C(c1cccc([N+](=O)[O-])c1)N1CCOCC1 | [N+](=O)([O-])C=1C=C(C(=O)O)C=CC1.ON1N=NC2=C1C=CC=C2.Cl.C(C)N=C=NCCCN(C)C.N1CCOCC1>>[N+](=O)([O-])C=1C=C(C(=O)N2CCOCC2)C=CC1 | [NH:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1.O[C:2](=[O:1])[c:3]1[cH:4][cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11]1)[N:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1 | C1COCCN1.O=C(O)c1cccc([N+](=O)[O-])c1 | O=C(c1cccc([N+](=O)[O-])c1)N1CCOCC1 | null | null | ClCCl.C(Cl)(Cl)Cl.O1CCCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | 2ef483949e7ba3e5f888cf14cdce25fa611f75be09fdf1854a473be519821b59 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1ccccc1)N1CCOCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#8:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#8:6]-[C:11]-[C:10]-1)-[c:3](:[c:4]):[c:5] | 89.8 | [{"value": 89.8, "product": "[N+](=O)([O-])C=1C=C(C(=O)N2CCOCC2)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | In tetrahydrofuran (100 ml) and dichloromethane (100 ml), 3-nitrobenzoic acid (7.58 g) was dissolved. Then 1-hydroxybenzotriazole (6.74 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (9.57 g), and morpholine (9.47 g) were added to the solution. The mixture was stirred at room temperature overnight. Aft... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1COCCN1 | C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1 | HO- | ClCCl.C(Cl)(Cl)Cl.O1CCCC1 | null | 8 | C1COCCN1.O=C(O)c1cccc([N+](=O)[O-])c1>ClCCl.C(Cl)(Cl)Cl.O1CCCC1>O=C(c1cccc([N+](=O)[O-])c1)N1CCOCC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7cc7d41500194b2d804cca39c54e96aa | O=C(c1cccc([N+](=O)[O-])c1)N1CCOCC1>>Nc1cccc(C(=O)N2CCOCC2)c1 | [N+](=O)([O-])C=1C=C(C(=O)N2CCOCC2)C=CC1>>NC=1C=C(C(=O)N2CCOCC2)C=CC1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][cH:5][c:6]([C:7](=[O:8])[N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[cH:15]1>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]([C:7](=[O:8])[N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[cH:15]1 | O=C(c1cccc([N+](=O)[O-])c1)N1CCOCC1 | Nc1cccc(C(=O)N2CCOCC2)c1 | null | [Pd] | C(C)O.O.NN | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(c1ccccc1)N1CCOCC1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 100.5 | [{"value": 100.5, "product": "NC=1C=C(C(=O)N2CCOCC2)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 30 | MINUTE | The compound ([13]-(132)-158) (8.63 g) prepared in Example 83 was dissolved in ethanol (400 ml), and the solution was heated to 50° C. To the suspention, a solution of 10% Pd/C (2.25 g) in ethanol and hydrazine monohydrate (4.4 ml) were added to the solution. The mixture was stirred for 30 minutes. After the reaction w... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.C1COCC[NH]1 | Other | [Pd].C(C)O.O.NN | 50 | 0.5 | O=C(c1cccc([N+](=O)[O-])c1)N1CCOCC1>[Pd].C(C)O.O.NN>Nc1cccc(C(=O)N2CCOCC2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8debf37587f1426b9a2fd8782e5c9316 | O=C(O)c1cc[n+]([O-])cc1.O=P(Cl)(Cl)Cl>>O=C(O)c1ccnc(Cl)c1 | P(=O)(Cl)(Cl)Cl.C(C1=CC=[N+](C=C1)[O-])(=O)O>>ClC=1C=C(C(=O)O)C=CN1 | [O-][n+:7]1[cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:10][cH:8]1.O=P(Cl)(Cl)[Cl:9]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][n:7][c:8]([Cl:9])[cH:10]1 | O=C(O)c1cc[n+]([O-])cc1.O=P(Cl)(Cl)Cl | O=C(O)c1ccnc(Cl)c1 | null | null | null | Miscellaneous | OtherReaction | a7e4b874c7a18ec6b4305e16cc93c9103d77bfb4ce559ead41b2d45f56dcb90f | a48150e9dff88baab32dd83daf5ab089c597626e3c583c33a5868d8e1353c1ea | c1ccncc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].[O-]-[n+;H0;D3:2]1:[c:3]:[c:4]:[c:5](-[C:6](=[O;D1;H0:7])-[O;D1;H1:8]):[c:9]:[cH;D2;+0:10]:1>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:10]1:[c:9]:[c:5](-[C:6](=[O;D1;H0:7])-[O;D1;H1:8]):[c:4]:[c:3]:[n;H0;D2;+0:2]:1 | null | [] | 120 | CELSIUS | 7 | HOUR | Phosphorus oxychloride (220.7 g) was added to isonicotinic acid N-oxide (50.064 g), and the mixture was stirred on an oil bath at 120° C. for 7 hours. The reaction mixture was slowly poured into ice water with vigorously stirring to precipitate light yellow crystals. The mixture was adjusted to approximately pH 4 with ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | C1=CC=[NH+]C=C1 | c1ccncc1 | c1ccncc1 | HCl | null | 120 | 7 | O=C(O)c1cc[n+]([O-])cc1.O=P(Cl)(Cl)Cl>>O=C(O)c1ccnc(Cl)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9ca3b20357e643e9bc74d3800e3ccc9e | C(=NC1CCCCC1)=NC1CCCCC1.C1COCCN1.CN(C)C=O.On1nnc2ccccc21>>CCCCC(=O)Nc1cc(C(=O)N2CCOCC2)ccn1 | CN(C=O)C.ON1N=NC2=C1C=CC=C2.C1(CCCCC1)N=C=NC1CCCCC1.N1CCOCC1>>C(CCCC)(=O)NC=1C=C(C(=O)N2CCOCC2)C=CN1 | C1CCC(N=[C:11]=[N:7][CH:8]2C[CH2:4][CH2:3][CH2:2][CH2:1]2)CC1.[NH:13]1[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1.CN(C)[CH:5]=[O:6].c1c[cH:20][cH:19][c:10]2[c:9]1nn[n:21]2[OH:12]>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5](=[O:6])[NH:7][c:8]1[cH:9][c:10]([C:11](=[O:12])[N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)[cH:19][cH:20][n... | C(=NC1CCCCC1)=NC1CCCCC1.C1COCCN1.CN(C)C=O.On1nnc2ccccc21 | CCCCC(=O)Nc1cc(C(=O)N2CCOCC2)ccn1 | null | null | null | Acylation | OtherReaction | b4eca18c1e81fb2adbb867f7c371ac807826031d01124995c3857abc5c07cb31 | d85bff90a58c0088fa8a198a2f67ce036783adfb91b17ebe99d5b32192428e50 | O=C(c1ccncc1)N1CCOCC1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].C1-C-C-C(-N=[C;H0;D2;+0:3]=[N;H0;D2;+0:4]-[CH;D3;+0:5]2-C-[CH2;D2;+0:6]-[C:7]-[C:8]-[CH2;D2;+0:9]-2)-C-C-1.[#8:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1.[OH;D1;+0:16]-[n;H0;D3;+0:17]1:n:n:[c;H0;D3;+0:18]2:c:c:[cH;D2;+0:19]:[c:20]:[c;H0;D3;+0:21]:2:1>>[CH3;D1;+0:9]-[C:8]-[C:7]-[CH... | null | [] | null | null | 16 | HOUR | The compound ([9]-(94)-467') (2.4610 g) prepared in Example 98 was dissolved in anhydrous dimethylformamide (DMF) (37 ml). Then, 1-hydroxybenzotriazole (1.9477 g), N,N'-dicyclohexylcarbodiimide (2.9739 g), and morpholine (1.3 ml) were added to the solution. The mixture was stirred at room temperature for 16 hours. The ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Secondary amine | Secondary amide.Tertiary amide | C1CCCCC1.C1CCCCC1.C1COCCN1.c1ccc2[nH]nnc2c1 | c1ccncc1.C1COCC[NH]1 | c1ccncc1.C1COCC[NH]1 | Other | null | null | 16 | C(=NC1CCCCC1)=NC1CCCCC1.C1COCCN1.CN(C)C=O.On1nnc2ccccc21>>CCCCC(=O)Nc1cc(C(=O)N2CCOCC2)ccn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5f18c5914e004a9f8905dfa1893ebe5b | CO[C@H](C)C(=O)O.CO[C@H](C)CO>>CO[C@@H](C)C(=O)O.CO[C@@H](C)CO | CO[C@@H](CO)C.CO[C@@H](C(=O)O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>CO[C@H](CO)C.CO[C@H](C(=O)O)C | [CH3:1][O:2][C@H:3]([CH3:4])[C:5](=[O:6])[OH:7].[CH3:8][O:9][C@H:10]([CH3:11])[CH2:12][OH:13]>>[CH3:1][O:2][C@@H:3]([CH3:4])[C:5](=[O:6])[OH:7].[CH3:8][O:9][C@@H:10]([CH3:11])[CH2:12][OH:13] | CO[C@H](C)C(=O)O.CO[C@H](C)CO | CO[C@@H](C)C(=O)O.CO[C@@H](C)CO | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | By reduction of the (+)-(R)-2-methoxy-propionic acid known from the prior art with lithium aluminium hydride (LiAlH4) the (-)-(R)-2-methoxy-propanol is obtained with a boiling point of 70° C. under a pressure of 76 mbar and a specific rotation of [α]D25 =-15.8° (c=100). The corresponding (+)-(S)-2-methoxy-propanol with... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | null | null | null | CO[C@H](C)C(=O)O.CO[C@H](C)CO>>CO[C@@H](C)C(=O)O.CO[C@@H](C)CO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-03dd32c613004882b1e3b3fe47dd3050 | CO[C@H](C)CO.Cc1ccc(S(=O)(=O)Cl)cc1>>CO[C@H](C)COS(=O)(=O)c1ccc(C)cc1 | CO[C@@H](CO)C.C1(=CC=C(C=C1)S(=O)(=O)Cl)C>>CO[C@@H](COS(=O)(=O)C1=CC=C(C=C1)C)C | [CH3:1][O:2][C@H:3]([CH3:4])[CH2:5][OH:6].Cl[S:7](=[O:8])(=[O:9])[c:10]1[cH:11][cH:12][c:13]([CH3:14])[cH:15][cH:16]1>>[CH3:1][O:2][C@H:3]([CH3:4])[CH2:5][O:6][S:7](=[O:8])(=[O:9])[c:10]1[cH:11][cH:12][c:13]([CH3:14])[cH:15][cH:16]1 | CO[C@H](C)CO.Cc1ccc(S(=O)(=O)Cl)cc1 | CO[C@H](C)COS(=O)(=O)c1ccc(C)cc1 | null | null | N1=CC=CC=C1 | Acylation | Formation of Sulfonic Esters | d05d91207659f8fa672c205a316a670adfe2b92492fc9adad2ee3f241e574fb9 | a7748b0f3b0eba3868d0cf03ae67721db046202accaaea9cadb4edbc96ec8768 | c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[OH;D1;+0:9]>>[C:7]-[C:8]-[O;H0;D2;+0:9]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | By reacting (-)-(R)-2-methoxypropanol with p-toluenesulphonic acid chloride in pyridine analogously to R. S. Tipson [J. Org. Chem. 9 (1944) 235] the (+)-(R)-2-methoxypropyl-p-toluenesulphonate is obtained in the form of a yellowish oil with a specific rotation of [α]D25 =+3.7° (c=100) and analogously, from (+)-(S)-2-me... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Primary alcohol.Sulfonyl halide | Tosylate | null | null | c1ccccc1 | HCl | N1=CC=CC=C1 | null | null | CO[C@H](C)CO.Cc1ccc(S(=O)(=O)Cl)cc1>N1=CC=CC=C1>CO[C@H](C)COS(=O)(=O)c1ccc(C)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c6c10cd15dfc4d01b84ec18ab3764f16 | C#CC1(O)CN2CCC1CC2.CCCCOc1ccc(Br)cn1>>CCCCOc1ccc(C#CC2(O)CN3CCC2CC3)cn1 | C(#C)C1(CN2CCC1CC2)O.BrC=1C=CC(=NC1)OCCCC.C(C)N(CC)CC>>C(CCC)OC1=CC=C(C=N1)C#CC1(CN2CCC1CC2)O | [CH:10]#[C:11][C:12]1([OH:13])[CH2:14][N:15]2[CH2:16][CH2:17][CH:18]1[CH2:19][CH2:20]2.Br[c:9]1[cH:8][cH:7][c:6]([O:5][CH2:4][CH2:3][CH2:2][CH3:1])[n:22][cH:21]1>>[CH3:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([C:10]#[C:11][C:12]2([OH:13])[CH2:14][N:15]3[CH2:16][CH2:17][CH:18]2[CH2:19][CH2:20]3)[cH:21][n:22]1 | C#CC1(O)CN2CCC1CC2.CCCCOc1ccc(Br)cn1 | CCCCOc1ccc(C#CC2(O)CN3CCC2CC3)cn1 | null | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Cu]I | CN(C=O)C | C-C Coupling | Sonogashira alkyne_aryl halide | d920908f7cd8d5c12cc1e0ae172ea45585ee68f03cd2df6faa8b9163bac60cda | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | C(#CC1CN2CCC1CC2)c1cccnc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.[C:7]-[C:8]#[CH;D1;+0:9]>>[C:7]-[C:8]#[C;H0;D2;+0:9]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1 | 25.2 | [{"value": 25.2, "product": "C(CCC)OC1=CC=C(C=N1)C#CC1(CN2CCC1CC2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | A stirred mixture of 3-ethynyl-3-hydroxyquinuclidine (600 mg), 5-bromo-2-n-butoxypyridine (920 mg), bis-(triphenylphosphine)-palladium (II) chloride (140 mg), copper (I) iodide (70 mg) and dry triethylamine (10 ml) in dry dimethylformamide (20 ml) was heated at 90° C. under an atmosphere of argon for 6 hours. The react... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccncc1 | c1ccncc1 | c1ccncc1.C1CN2CCC1CC2 | HBr | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Cu]I.CN(C=O)C | 90 | null | C#CC1(O)CN2CCC1CC2.CCCCOc1ccc(Br)cn1>C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Cu]I.CN(C=O)C>CCCCOc1ccc(C#CC2(O)CN3CCC2CC3)cn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3e2d6cb3d26542d4af0ef67db3bb40ab | Brc1ccc(Br)nc1.CCCCO>>CCCCOc1ccc(Br)cn1 | [H-].[Na+].C(CCC)O.[H][H].BrC1=NC=C(C=C1)Br>>BrC=1C=CC(=NC1)OCCCC | Br[c:6]1[cH:7][cH:8][c:9]([Br:10])[cH:11][n:12]1.[CH3:1][CH2:2][CH2:3][CH2:4][OH:5]>>[CH3:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([Br:10])[cH:11][n:12]1 | Brc1ccc(Br)nc1.CCCCO | CCCCOc1ccc(Br)cn1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | ea617b323b892eda23f5ae30e789991ea9692064ef355a16e8ed81c16e743d2b | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccncc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | Sodium hydride (60% w/v dispersion in mineral oil; 1.8 g) was added in portions over 20 minutes to n-butanol (100 ml) with stirring. The mixture was then stirred until no further hydrogen evolution was noted. 2,5-Dibromopyridine (7.1 g) was added and the resulting mixture stirred at reflux for 6 hours. After cooling, t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccncc1 | c1ccncc1 | c1ccncc1 | HBr | null | null | null | Brc1ccc(Br)nc1.CCCCO>>CCCCOc1ccc(Br)cn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0a8a7f7391de4560854070e9af7b0eeb | C[C@H](C(=O)OC(C)(C)C)C(N)(N)C(=O)O>>CC(C)(C)OC(=O)N[C@H]1CCNC1=O | Cl.CN(CCCN=C=NCC)C.C(=O)(OC(C)(C)C)[C@H](C(C(=O)O)(N)N)C.C(C)N(CC)CC.O.ON1N=NC2=C1C=CC=C2>>C(C)(C)(C)OC(N[C@@H]1C(NCC1)=O)=O | OC([C:13]([NH2:8])([C@@H:9]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH3:10])[NH2:12])=[O:14]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][NH:12][C:13]1=[O:14] | C[C@H](C(=O)OC(C)(C)C)C(N)(N)C(=O)O | CC(C)(C)OC(=O)N[C@H]1CCNC1=O | null | null | C1CCOC1 | Functional Group Interconversion | OtherReaction | df4ed86ce3b13d026296b5d16b2b83654b2f4a0eeecdbfcb4970ca5fd979ba5f | de7b6965e5bd008e02634eac07364d65da582f6be224fde946a47e5de914f290 | O=C1CCCN1 | O-C(=[O;H0;D1;+0:1])-[C;H0;D4;+0:2](-[NH2;D1;+0:3])(-[NH2;D1;+0:4])-[C@H;D3;+0:5](-[CH3;D1;+0:6])-[C;H0;D3;+0:7](=[O;D1;H0:8])-[#8:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[C;D1;H3:13]>>[C;D1;H3:11]-[C:10](-[C;D1;H3:12])(-[C;D1;H3:13])-[#8:9]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[NH;D2;+0:4]-[C@H;D3;+0:5]1-[CH2;D2;+0:6]-[C:14]-... | 85.2 | [{"value": 85.2, "product": "C(C)(C)(C)OC(N[C@@H]1C(NCC1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 4 | HOUR | (S)-Boc-Diaminobutyric acid (25 g, 115 mmol), triethylamine (35 g, 344 mmol), and 1-hydroxybenzotriazole hydrate (19.3 g, 143 mmol) are dissolved in 300 mL of THF. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (27.4 g, 143 mmol) is added to the solution. The solution is heated at 60° C. over 15 min. A whi... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester.Primary amine.Primary amine.Boc | Carbamic ester.Ether.Secondary amide.Boc | null | C1CCNC1 | C1CCNC1 | HO- | C1CCOC1 | 60 | 4 | C[C@H](C(=O)OC(C)(C)C)C(N)(N)C(=O)O>C1CCOC1>CC(C)(C)OC(=O)N[C@H]1CCNC1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4851d21d5df64c59acbb06e19d6ebd27 | CC(C)(C)OC(=O)N[C@H]1CCN(Cc2cccc(C#N)c2)C1=O>>N#Cc1cccc(CN2CC[C@H](N)C2=O)c1 | C(C)(C)(C)OC(N[C@@H]1C(N(CC1)CC1=CC(=CC=C1)C#N)=O)=O.Cl>>Cl.N[C@@H]1C(N(CC1)CC=1C=C(C#N)C=CC1)=O | CC(C)(C)OC(=O)[NH:14][C@H:13]1[CH2:12][CH2:11][N:10]([CH2:9][c:8]2[cH:7][cH:6][cH:5][c:4]([C:3]#[N:2])[cH:17]2)[C:15]1=[O:16]>>[N:2]#[C:3][c:4]1[cH:5][cH:6][cH:7][c:8]([CH2:9][N:10]2[CH2:11][CH2:12][C@H:13]([NH2:14])[C:15]2=[O:16])[cH:17]1 | CC(C)(C)OC(=O)N[C@H]1CCN(Cc2cccc(C#N)c2)C1=O | N#Cc1cccc(CN2CC[C@H](N)C2=O)c1 | null | null | CCOC(=O)C | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C1CCCN1Cc1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]1-[C:3]-[C:4]-[#7:5](-[C:6])-[C:7]-1=[O;D1;H0:8]>>[C:6]-[#7:5]1-[C:4]-[C:3]-[C:2](-[NH2;D1;+0:1])-[C:7]-1=[O;D1;H0:8] | null | [] | null | null | 4 | HOUR | To a solution of [1-(3-cyanobenzyl)-2-oxo-pyrrolidin-3-(S)-yl]-carbamic acid tert-butyl ester (9.1 g, 29 mmol) in 150 mL of EtOAc at 0° C. is bubbled HCl gas for 10 min. After this time, the solution is stirred for 4 h. The solution is then concentrated to afford the title compound (7.3 g, 29 mmol) as a white solid.
Co... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.C1CC[NH]C1 | HO- | CCOC(=O)C | null | 4 | CC(C)(C)OC(=O)N[C@H]1CCN(Cc2cccc(C#N)c2)C1=O>CCOC(=O)C>N#Cc1cccc(CN2CC[C@H](N)C2=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9e191b19e3934f0d93b05d666f8a5d42 | N#Cc1cccc(CN2CC[C@H](N)C2=O)c1.O=S(=O)(Cl)c1cc2ccccc2s1>>N#Cc1cccc(CN2CC[C@H](NS(=O)(=O)c3cc4ccccc4s3)C2=O)c1 | C(C)N(CC)CC.Cl.N[C@@H]1C(N(CC1)CC=1C=C(C#N)C=CC1)=O.S1C2=C(C=C1S(=O)(=O)Cl)C=CC=C2>>C(#N)C=1C=C(CN2C([C@H](CC2)NS(=O)(=O)C2=CC3=C(S2)C=CC=C3)=O)C=CC1 | [N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][N:9]2[CH2:10][CH2:11][C@H:12]([NH2:13])[C:26]2=[O:27])[cH:28]1.Cl[S:14](=[O:15])(=[O:16])[c:17]1[cH:18][c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]2[s:25]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][N:9]2[CH2:10][CH2:11][C@H:12]([NH:13][S:14](=[O:15])(=[O:16])[c:17]3... | N#Cc1cccc(CN2CC[C@H](N)C2=O)c1.O=S(=O)(Cl)c1cc2ccccc2s1 | N#Cc1cccc(CN2CC[C@H](NS(=O)(=O)c3cc4ccccc4s3)C2=O)c1 | null | null | C(Cl)Cl.CCOC(=O)C | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C1[C@@H](NS(=O)(=O)c2cc3ccccc3s2)CCN1Cc1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[#16;a:6]:[c:7].[C:8]-[#7:9]1-[C:10]-[C:11]-[C:12](-[NH2;D1;+0:13])-[C:14]-1=[O;D1;H0:15]>>[C:8]-[#7:9]1-[C:10]-[C:11]-[C:12](-[NH;D2;+0:13]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[#16;a:6]:[c:7])-[C:14]-1=[O;D1;H0:15] | 79 | [{"value": 79.0, "product": "C(#N)C=1C=C(CN2C([C@H](CC2)NS(=O)(=O)C2=CC3=C(S2)C=CC=C3)=O)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of 3-(3-(S)-amino-2-oxo-pyrrolidin-1-ylmethyl)-benzonitrile hydrochloride (0.36 g, 1.43 mmol) in 15 mL of CH2Cl2 is added benzo[b]thiophene-2-sulfonyl chloride (0.32 g, 1.38 mmol). To the resulting solution is added triethylamine (0.29 g, 2.88 mmol). After 16 h, the solution is diluted with EtOAc. The sol... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.C1CC[NH]C1.c1ccc2sccc2c1 | HCl | C(Cl)Cl.CCOC(=O)C | null | 16 | N#Cc1cccc(CN2CC[C@H](N)C2=O)c1.O=S(=O)(Cl)c1cc2ccccc2s1>C(Cl)Cl.CCOC(=O)C>N#Cc1cccc(CN2CC[C@H](NS(=O)(=O)c3cc4ccccc4s3)C2=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f4e8e6ec20fc45b7ba597aed2b56cab8 | CI.N#Cc1cccc(CN2CC[C@H](NS(=O)(=O)c3cc4ccccc4s3)C2=O)c1>>CN([C@H]1CCN(Cc2cccc(C#N)c2)C1=O)S(=O)(=O)c1cc2ccccc2s1 | C(=O)([O-])[O-].[K+].[K+].C(#N)C=1C=C(CN2C([C@H](CC2)NS(=O)(=O)C2=CC3=C(S2)C=CC=C3)=O)C=CC1.CI>>C(#N)C=1C=C(CN2C([C@H](CC2)N(S(=O)(=O)C2=CC3=C(S2)C=CC=C3)C)=O)C=CC1 | I[CH3:1].[NH:2]([C@H:3]1[CH2:4][CH2:5][N:6]([CH2:7][c:8]2[cH:9][cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15]2)[C:16]1=[O:17])[S:18](=[O:19])(=[O:20])[c:21]1[cH:22][c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]2[s:29]1>>[CH3:1][N:2]([C@H:3]1[CH2:4][CH2:5][N:6]([CH2:7][c:8]2[cH:9][cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15]2)[C:16... | CI.N#Cc1cccc(CN2CC[C@H](NS(=O)(=O)c3cc4ccccc4s3)C2=O)c1 | CN([C@H]1CCN(Cc2cccc(C#N)c2)C1=O)S(=O)(=O)c1cc2ccccc2s1 | null | null | CCOC(=O)C.O.CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | c6ca050f6d67acb7bc6fc8b4d7848b3f349e4e8db81643cbb6d12b5a34cbf965 | 9d3dfd18cb6410898a6d822a6d80081d602cf34984cafbfa56b84aa4b38ddbf6 | O=C1[C@@H](NS(=O)(=O)c2cc3ccccc3s2)CCN1Cc1ccccc1 | I-[CH3;D1;+0:1].[#16;a:2]:[c:3]-[#16:4](=[O;D1;H0:5])(=[O;D1;H0:6])-[NH;D2;+0:7]-[C:8]1-[C:9]-[C:10]-[#7:11](-[C:12])-[C:13]-1=[O;D1;H0:14]>>[#16;a:2]:[c:3]-[#16:4](=[O;D1;H0:5])(=[O;D1;H0:6])-[N;H0;D3;+0:7](-[CH3;D1;+0:1])-[C:8]1-[C:9]-[C:10]-[#7:11](-[C:12])-[C:13]-1=[O;D1;H0:14] | 96.7 | [{"value": 96.7, "product": "C(#N)C=1C=C(CN2C([C@H](CC2)N(S(=O)(=O)C2=CC3=C(S2)C=CC=C3)C)=O)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | To a solution of benzo[b]thiophene-2-sulfonic acid [1-(3-cyano-benzyl)-2-oxo-pyrrolidin-3-(S)-yl]-amide (0.25 g, 0.61 mmol) in 3 mL of DMF is added methyl iodide (0.13 g, 0.91 mmol) followed by K2CO3 (0.13 g, 0.91 mmol). The solution is stirred at ambient temperatures for 6 h. After this time, the solution is diluted w... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Tertiary amine | null | null | C1CC[NH]C1.c1ccccc1.c1ccc2sccc2c1 | HI | CCOC(=O)C.O.CN(C)C=O | null | 6 | CI.N#Cc1cccc(CN2CC[C@H](NS(=O)(=O)c3cc4ccccc4s3)C2=O)c1>CCOC(=O)C.O.CN(C)C=O>CN([C@H]1CCN(Cc2cccc(C#N)c2)C1=O)S(=O)(=O)c1cc2ccccc2s1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e6dea7c2aa4947e5bcc870d26f4d2244 | OCc1csc(I)c1>>N#Cc1cc(CO)cs1 | IC1=CC(=CS1)CO.CN(C)C=O>>OCC=1C=C(SC1)C#N | I[c:3]1[cH:4][c:5]([CH2:6][OH:7])[cH:8][s:9]1>>[N:1]#[C:2][c:3]1[cH:4][c:5]([CH2:6][OH:7])[cH:8][s:9]1 | OCc1csc(I)c1 | N#Cc1cc(CO)cs1 | null | [C-]#N.[Zn+2].[C-]#N | CCOC(=O)C | Miscellaneous | OtherReaction | ebc2e53b7bb2dea43338a6ebf76eca4e26da1c045bb86707697af7150e28603d | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | c1ccsc1 | I-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1>>[N;D1;H0:6]#[C:7]-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1 | null | [] | 80 | CELSIUS | 6 | HOUR | To a solution of (5-iodo-thiophene-3-yl)methanol (42 g, 176 mmol) in 150 mL of DMF is added zinc cyanide (12.4 g, 106 mmol) and tetrakis(triphenylphospine)palladium (0) (8.13 g, 7.04 mmol). The solution is heated to 80° C. After 6 h, the solution is diluted with 3 L of EtOAc. The resulting solution is washed with 1N NH... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccsc1 | c1ccsc1 | c1ccsc1 | I- | [C-]#N.[Zn+2].[C-]#N.CCOC(=O)C | 80 | 6 | OCc1csc(I)c1>[C-]#N.[Zn+2].[C-]#N.CCOC(=O)C>N#Cc1cc(CO)cs1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3997d852565a4edcadde399de94e54e4 | BrC(Br)(Br)Br.N#Cc1cc(CO)cs1>>N#Cc1cc(CBr)cs1 | OCC=1C=C(SC1)C#N.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(Br)(Br)(Br)Br>>BrCC=1C=C(SC1)C#N | BrC(Br)(Br)[Br:7].O[CH2:6][c:5]1[cH:4][c:3]([C:2]#[N:1])[s:9][cH:8]1>>[N:1]#[C:2][c:3]1[cH:4][c:5]([CH2:6][Br:7])[cH:8][s:9]1 | BrC(Br)(Br)Br.N#Cc1cc(CO)cs1 | N#Cc1cc(CBr)cs1 | null | null | C1CCOC1 | Functional Group Interconversion | Appel reaction | 752e1807cd47d8316010cc3f92eab16c5a89ffb844d9514fcae469ba993c78dd | 2c6b51fb1e17cb2c93d565e0423c75825df2c8e11c870e0c98b278f20ba9f3ad | c1ccsc1 | Br-C(-Br)(-Br)-[Br;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[#16;a:6]:[c:7]:1>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[#16;a:6]:[c:7]:1 | 95.8 | [{"value": 95.8, "product": "BrCC=1C=C(SC1)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of 4-hydroxymethyl-thiophene-2-carbonitrile (10 g, 72 mmol), in 360 mL of THF is added triphenyl phosphine (18.3 g, 76 mmol) and carbon tetrabromide (25 g, 76 mmol). After 3 h, the solution is filtered and concentrated. The crude product is purified by column chromatography eluting with gradient of 5% EtO... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Primary alcohol | Primary halide | null | null | c1ccsc1 | HBr | C1CCOC1 | null | 3 | BrC(Br)(Br)Br.N#Cc1cc(CO)cs1>C1CCOC1>N#Cc1cc(CBr)cs1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-84a55dcc108c4ee98e6877dc7c417430 | CC(C)(C)OC(=O)N[C@H]1CCNC1=O.N#Cc1cc(CBr)cs1>>CC(C)(C)OC(=O)N[C@H]1CCN(Cc2csc(C#N)c2)C1=O | C(C)(C)(C)OC(N[C@@H]1C(NCC1)=O)=O.BrCC=1C=C(SC1)C#N.[H-].[Na+]>>C(C)(C)(C)OC(N[C@@H]1C(N(CC1)CC1=CSC(=C1)C#N)=O)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][NH:12][C:21]1=[O:22].Br[CH2:13][c:14]1[cH:15][s:16][c:17]([C:18]#[N:19])[cH:20]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][N:12]([CH2:13][c:14]2[cH:15][s:16][c:17]([C:18]#[N:19])[cH:20]2)[C:21]1=[O:22] | CC(C)(C)OC(=O)N[C@H]1CCNC1=O.N#Cc1cc(CBr)cs1 | CC(C)(C)OC(=O)N[C@H]1CCN(Cc2csc(C#N)c2)C1=O | null | null | C1CCOC1.CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | f5f217f17d493fffc808e7019c66db8bb20f63ec70b29db349ba715e196bdaf0 | 4a6c1e88c9e8bed487b746792f88d478ff36cc235f9a217d4632e6babdebdc9a | O=C1CCCN1Cc1ccsc1 | Br-[CH2;D2;+0:1]-[c:2]1:[c:3]:[#16;a:4]:[c:5]:[c:6]:1.[O;D1;H0:7]=[C:8]1-[C:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[O;D1;H0:7]=[C:8]1-[C:9]-[C:10]-[C:11]-[N;H0;D3;+0:12]-1-[CH2;D2;+0:1]-[c:2]1:[c:3]:[#16;a:4]:[c:5]:[c:6]:1 | 86.3 | [{"value": 86.3, "product": "C(C)(C)(C)OC(N[C@@H]1C(N(CC1)CC1=CSC(=C1)C#N)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of (2-oxo-pyrrolidin-3-(S)-yl)-carbamic acid tert-butyl ester (3.2 g, 16 mmol), prepared as described in EXAMPLE 1, Part A in 80 mL of THF:DMF (10:1) at 0° C. is added 4-bromomethyl-thiophene-2-carbonitrile (3.23 g, 16 mmol) and sodium hydride (60% dispersion in oil, 0.67 g, 16.8 mmol). After addition, th... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amide | Tertiary amide | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccsc1 | HBr | C1CCOC1.CN(C)C=O | null | 2 | CC(C)(C)OC(=O)N[C@H]1CCNC1=O.N#Cc1cc(CBr)cs1>C1CCOC1.CN(C)C=O>CC(C)(C)OC(=O)N[C@H]1CCN(Cc2csc(C#N)c2)C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e29b70eff24e450cac1d8727621cd4a4 | CC(C)(C)OC(=O)N[C@H]1CCN(Cc2csc(C#N)c2)C1=O>>N#Cc1cc(CN2CC[C@H](N)C2=O)cs1 | C(C)(C)(C)OC(N[C@@H]1C(N(CC1)CC1=CSC(=C1)C#N)=O)=O.Cl>>Cl.N[C@@H]1C(N(CC1)CC=1C=C(SC1)C#N)=O | CC(C)(C)OC(=O)[NH:12][C@H:11]1[CH2:10][CH2:9][N:8]([CH2:7][c:6]2[cH:5][c:4]([C:3]#[N:2])[s:16][cH:15]2)[C:13]1=[O:14]>>[N:2]#[C:3][c:4]1[cH:5][c:6]([CH2:7][N:8]2[CH2:9][CH2:10][C@H:11]([NH2:12])[C:13]2=[O:14])[cH:15][s:16]1 | CC(C)(C)OC(=O)N[C@H]1CCN(Cc2csc(C#N)c2)C1=O | N#Cc1cc(CN2CC[C@H](N)C2=O)cs1 | null | null | CCOC(=O)C | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C1CCCN1Cc1ccsc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]1-[C:3]-[C:4]-[#7:5](-[C:6])-[C:7]-1=[O;D1;H0:8]>>[C:6]-[#7:5]1-[C:4]-[C:3]-[C:2](-[NH2;D1;+0:1])-[C:7]-1=[O;D1;H0:8] | null | [] | null | null | 3 | HOUR | [1-(5-Cyanothiophene3-ylmethyl)-2-oxo-pyrrolidin-3-(S)-yl]-carbamic acid tert-butyl ester (4.0 g, 13.8 mmol) is added to a solution of 100 mL of EtOAc saturated with HCl gas at 0° C. After 3 h, the solution is concentrated. The title compound (3.3 g, 13.5 mmol) is obtained as a white solid.
Conditions: See reaction.not... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccsc1.C1CC[NH]C1 | HO- | CCOC(=O)C | null | 3 | CC(C)(C)OC(=O)N[C@H]1CCN(Cc2csc(C#N)c2)C1=O>CCOC(=O)C>N#Cc1cc(CN2CC[C@H](N)C2=O)cs1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7a1103e60e4f437b972528004aa20c58 | N=C(N)c1cccc(CN2CC[C@H](NS(=O)(=O)c3cc4c(Cl)cc(Cl)cc4s3)C2=O)c1.O=C(Cl)OCC(Cl)(Cl)Cl>>N=C(NC(=O)OCC(Cl)(Cl)Cl)c1cccc(CN2CC[C@H](NS(=O)(=O)c3cc4c(Cl)cc(Cl)cc4s3)C2=O)c1 | CN1CCCCC1.FC(C(=O)O)(F)F.ClC1=CC(=CC=2SC(=CC21)S(=O)(=O)N[C@@H]2C(N(CC2)CC=2C=C(C(=N)N)C=CC2)=O)Cl.ClC(=O)OCC(Cl)(Cl)Cl>>ClC(COC(NC(=N)C1=CC(=CC=C1)CN1C([C@H](CC1)NS(=O)(=O)C1=CC2=C(S1)C=C(C=C2Cl)Cl)=O)=O)(Cl)Cl | [NH:1]=[C:2]([NH2:3])[c:12]1[cH:13][cH:14][cH:15][c:16]([CH2:17][N:18]2[CH2:19][CH2:20][C@H:21]([NH:22][S:23](=[O:24])(=[O:25])[c:26]3[cH:27][c:28]4[c:29]([Cl:30])[cH:31][c:32]([Cl:33])[cH:34][c:35]4[s:36]3)[C:37]2=[O:38])[cH:39]1.Cl[C:4](=[O:5])[O:6][CH2:7][C:8]([Cl:9])([Cl:10])[Cl:11]>>[NH:1]=[C:2]([NH:3][C:4](=[O:5]... | N=C(N)c1cccc(CN2CC[C@H](NS(=O)(=O)c3cc4c(Cl)cc(Cl)cc4s3)C2=O)c1.O=C(Cl)OCC(Cl)(Cl)Cl | N=C(NC(=O)OCC(Cl)(Cl)Cl)c1cccc(CN2CC[C@H](NS(=O)(=O)c3cc4c(Cl)cc(Cl)cc4s3)C2=O)c1 | null | null | CCOC(=O)C.C(Cl)Cl.CN(C)C=O | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | O=C1[C@@H](NS(=O)(=O)c2cc3ccccc3s2)CCN1Cc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[N;D1;H1:5]=[C:6](-[NH2;D1;+0:7])-[c:8]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6](=[N;D1;H1:5])-[c:8] | 75 | [{"value": 75.0, "product": "ClC(COC(NC(=N)C1=CC(=CC=C1)CN1C([C@H](CC1)NS(=O)(=O)C1=CC2=C(S1)C=C(C=C2Cl)Cl)=O)=O)(Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of 3-[3-(S)-(4,6-dichlorobenzo[b]thiophene-2-sulfonylamino)-2-oxo-pyrrolidin-1-ylmethyl]-benzamidine trifluoroacetate (0.25 g, 0.40 mmol), prepared as in EXAMPLE 14, Part E, in 4 mL of CH2Cl2 :DMF (10:1) is added N-methyl piperidine (0.12 g, 1.2 mmol) followed by trichloroethyl chloroformate (0.93 g, 0.44... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccccc1.C1CC[NH]C1.c1ccc2sccc2c1 | HCl | CCOC(=O)C.C(Cl)Cl.CN(C)C=O | null | 16 | N=C(N)c1cccc(CN2CC[C@H](NS(=O)(=O)c3cc4c(Cl)cc(Cl)cc4s3)C2=O)c1.O=C(Cl)OCC(Cl)(Cl)Cl>CCOC(=O)C.C(Cl)Cl.CN(C)C=O>N=C(NC(=O)OCC(Cl)(Cl)Cl)c1cccc(CN2CC[C@H](NS(=O)(=O)c3cc4c(Cl)cc(Cl)cc4s3)C2=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-68a8e77da56c464fb8e4488b01b277d1 | Cc1cc(C#N)ccc1[N+](=O)[O-]>>Cc1cc(C#N)ccc1N | C(=O)(O)[O-].[Na+].CC=1C=C(C#N)C=CC1[N+](=O)[O-].Cl[Sn]Cl>>NC1=C(C=C(C#N)C=C1)C | O=[N+:10]([O-])[c:9]1[c:2]([CH3:1])[cH:3][c:4]([C:5]#[N:6])[cH:7][cH:8]1>>[CH3:1][c:2]1[cH:3][c:4]([C:5]#[N:6])[cH:7][cH:8][c:9]1[NH2:10] | Cc1cc(C#N)ccc1[N+](=O)[O-] | Cc1cc(C#N)ccc1N | null | null | CCO.CCOC(=O)C | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 70.7 | [{"value": 70.7, "product": "NC1=C(C=C(C#N)C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 3-methyl-4-nitrobenzonitrile (2.0 g, 12.3 mmol) in 100 mL of EtOH is added SnCl2 (13.9 g, 61.7 mmol). The resulting solution is heated at reflux. After 2 h, the solution is cooled to ambient temperatures. The solution is poured into 150 mL of ice water. The pH of the solution is adjusted to >7 with a s... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | CCO.CCOC(=O)C | null | 2 | Cc1cc(C#N)ccc1[N+](=O)[O-]>CCO.CCOC(=O)C>Cc1cc(C#N)ccc1N |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8506789e76894b63af6d91cbe4235510 | Cc1cc(C#N)ccc1N.O=C(c1ccccc1)c1ccccc1>>Cc1cc(C#N)ccc1N=C(c1ccccc1)c1ccccc1 | NC1=C(C=C(C#N)C=C1)C.C(C1=CC=CC=C1)(=O)C1=CC=CC=C1.C1(=CC=C(C=C1)S(=O)(=O)O)C>>C(C1=CC=CC=C1)(C1=CC=CC=C1)=NC1=C(C=C(C#N)C=C1)C | [CH3:1][c:2]1[cH:3][c:4]([C:5]#[N:6])[cH:7][cH:8][c:9]1[NH2:10].O=[C:11]([c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][c:2]1[cH:3][c:4]([C:5]#[N:6])[cH:7][cH:8][c:9]1[N:10]=[C:11]([c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1 | Cc1cc(C#N)ccc1N.O=C(c1ccccc1)c1ccccc1 | Cc1cc(C#N)ccc1N=C(c1ccccc1)c1ccccc1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Addition of primary amines to ketones/thiocarbonyls | cb968592dec1a2c40e9f51052b6ef3c2d7edca4da22c8c4bb0fad7e1c1c69433 | 009cc6a97ebe0dc96c669f0ef59b95bcc20de7cae20b1b648ce8f8fa82309e57 | c1ccc(N=C(c2ccccc2)c2ccccc2)cc1 | O=[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[c:3]:[c:2](-[C;H0;D3;+0:1](=[N;H0;D2;+0:8]-[c:9](:[c:10]):[c:11])-[c:5](:[c:6]):[c:7]):[c:4] | 90.3 | [{"value": 90.3, "product": "C(C1=CC=CC=C1)(C1=CC=CC=C1)=NC1=C(C=C(C#N)C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a solution of 4-amino-3-methyl benzonitrile (1.20 g, 9.08 mmol) in 75 mL of toluene is added benzophenone (1.74 g, 9.53 mmol) and p-toluenesulfonic acid (0.43 g, 2.1 mmol). The reaction vessel is fitted with a Dean-Stark trap and the solution is heated at reflux. After 24 h, the solution is cooled to ambient tempera... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Substituted imine | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C1(=CC=CC=C1)C | null | 24 | Cc1cc(C#N)ccc1N.O=C(c1ccccc1)c1ccccc1>C1(=CC=CC=C1)C>Cc1cc(C#N)ccc1N=C(c1ccccc1)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d5d7a05761ee49b4bed0ffdf724b4bc7 | Cc1cc(C#N)ccc1N=C(c1ccccc1)c1ccccc1.O=C1CCC(=O)N1Br>>N#Cc1ccc(N=C(c2ccccc2)c2ccccc2)c(CBr)c1 | C(C1=CC=CC=C1)(C1=CC=CC=C1)=NC1=C(C=C(C#N)C=C1)C.BrN1C(CCC1=O)=O.C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O>>C(C1=CC=CC=C1)(C1=CC=CC=C1)=NC1=C(C=C(C#N)C=C1)CBr | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([N:7]=[C:8]([c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[c:21]([CH3:22])[cH:24]1.O=C1CCC(=O)N1[Br:23]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([N:7]=[C:8]([c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[c:21... | Cc1cc(C#N)ccc1N=C(c1ccccc1)c1ccccc1.O=C1CCC(=O)N1Br | N#Cc1ccc(N=C(c2ccccc2)c2ccccc2)c(CBr)c1 | null | null | C(Cl)Cl.C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccc(N=C(c2ccccc2)c2ccccc2)cc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 56.9 | [{"value": 56.9, "product": "C(C1=CC=CC=C1)(C1=CC=CC=C1)=NC1=C(C=C(C#N)C=C1)CBr", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4-(benzhydrylidene-amino)-3-methyl-benzonitrile (1.36 g, 4.27 mmol) in 40 mL of CCl4 is added N-bromosuccinimide (0.84 g, 4.7 mmol) and benzoyl peroxide (0.22 g, 0.64 mmol). The solution is heated to reflux for 16 h. The solution is cooled to ambient temperatures. The solution is diluted with CH2Cl2. T... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl.C(Cl)(Cl)(Cl)Cl | null | null | Cc1cc(C#N)ccc1N=C(c1ccccc1)c1ccccc1.O=C1CCC(=O)N1Br>C(Cl)Cl.C(Cl)(Cl)(Cl)Cl>N#Cc1ccc(N=C(c2ccccc2)c2ccccc2)c(CBr)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8ec2d97e687846619b32961cdb968717 | ClI.O=Cc1ccccc1O>>O=Cc1cc(I)ccc1O | S(=O)([O-])[O-].[Na+].[Na+].C(C=1C(O)=CC=CC1)=O.ClCl.ICl>>OC1=C(C=O)C=C(C=C1)I | Cl[I:6].[O:1]=[CH:2][c:3]1[cH:4][cH:5][cH:7][cH:8][c:9]1[OH:10]>>[O:1]=[CH:2][c:3]1[cH:4][c:5]([I:6])[cH:7][cH:8][c:9]1[OH:10] | ClI.O=Cc1ccccc1O | O=Cc1cc(I)ccc1O | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | f6effe61353895b318215d8bd9b6bb1105cafbf7be8c217d748df587260b32c3 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccccc1 | Cl-[I;H0;D1;+0:1].[O;D1;H0:2]=[C:3]-[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]>>[I;H0;D1;+0:1]-[c;H0;D3;+0:6](:[c:5]:[c:4]-[C:3]=[O;D1;H0:2]):[c:7]:[c:8] | null | [] | null | null | 14 | HOUR | To a solution of salicylaldehyde (10 g, 82 mmol) in 50 mL of CH2 Cl2 is added 22 mL of a 1M ICl solution in CH2Cl2. The solution is stirred for 14 h. After this time, a saturated solution of sodium sulfite is added until the color is discharged. The solution is diluted with CH2Cl2. The layers are separated. The organic... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | C(Cl)Cl | null | 14 | ClI.O=Cc1ccccc1O>C(Cl)Cl>O=Cc1cc(I)ccc1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2272a341dfe943cb9a6785a30ad21c5c | COCCOCOCl.O=Cc1cc(I)ccc1O>>COCCOCOc1ccc(I)cc1CO | COCCOCOCl.Cl.[BH4-].[Na+].[H-].[Na+].OC1=C(C=O)C=C(C=C1)I>>IC=1C=CC(=C(CO)C1)OCOCCOC | ClO[CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1].[OH:7][c:8]1[cH:9][cH:10][c:11]([I:12])[cH:13][c:14]1[CH:15]=[O:16]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([I:12])[cH:13][c:14]1[CH2:15][OH:16] | COCCOCOCl.O=Cc1cc(I)ccc1O | COCCOCOc1ccc(I)cc1CO | null | null | C1CCOC1.O.CCOCC.CN1C(N(CCC1)C)=O | Heteroatom Alkylation and Arylation | OtherReaction | 1f796c19d61e38a980dbd12a8b7e4bc91b4c45606bee8630f6ab6cb5896a36ab | 2348e4239c85d37ea6edd02746be3284fcef19afee175a79ad4b1cb0d469e15f | c1ccccc1 | Cl-O-[CH2;D2;+0:1]-[#8:2]-[C:3].[O;H0;D1;+0:4]=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8](-[OH;D1;+0:9]):[c:10]>>[C:3]-[#8:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:9]-[c:8](:[c:10]):[c:6](-[CH2;D2;+0:5]-[OH;D1;+0:4]):[c:7] | 80.4 | [{"value": 80.4, "product": "IC=1C=CC(=C(CO)C1)OCOCCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -15 | CELSIUS | 45 | MINUTE | To a solution of sodium hydride (1.2 g of a 60% mineral oil dispersion, 52 mmol) in 25 mL of THF at 0° C., is added 2-hydroxy-5-iodo-benzaldehyde (7.0 g, 28 mmol). To the resulting solution is added 2-methoxy-ethoxymethoxy chloride (3.4 mL, 30 mmol) and 4 mL of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone. The so... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ether.Aromatic alcohol | Ether.Ether.Primary alcohol | null | null | c1ccccc1 | Other | C1CCOC1.O.CCOCC.CN1C(N(CCC1)C)=O | -15 | 0.75 | COCCOCOCl.O=Cc1cc(I)ccc1O>C1CCOC1.O.CCOCC.CN1C(N(CCC1)C)=O>COCCOCOc1ccc(I)cc1CO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fcd44485706940d6937ed2c6fbc98557 | COCCOCOc1ccc(I)cc1CO.NC(=O)CCC(=O)NBr>>COCCOCOc1ccc(I)cc1CBr | BrNC(CCC(=O)N)=O.IC=1C=CC(=C(CO)C1)OCOCCOC.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>IC=1C=CC(=C(CBr)C1)OCOCCOC | O[CH2:15][c:14]1[c:8]([O:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[cH:9][cH:10][c:11]([I:12])[cH:13]1.NC(=O)CCC(=O)N[Br:16]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([I:12])[cH:13][c:14]1[CH2:15][Br:16] | COCCOCOc1ccc(I)cc1CO.NC(=O)CCC(=O)NBr | COCCOCOc1ccc(I)cc1CBr | null | null | C1CCOC1 | Functional Group Interconversion | OtherReaction | 36d5a3000ac6c18c3e3d0fda946e9d162639e9954840bbf4cf8fd21a99f6135c | a49bb2725045f0903d387e3d995d862f3db137c208b16c8cc18a21cfd61f70da | c1ccccc1 | N-C(=O)-C-C-C(=O)-N-[Br;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | 5 | MINUTE | To a solution of 5-iodo-2-(2-methoxy-ethoxymethoxy)-benzyl alcohol (7.5 g, 22 mmol) in 60 mL of THF at 15° C. is added triphenylphospine (6.35 g, 24 mmol) followed by N-bromosuccinamide (4.3 g, 24 mmol). The solution is stirred for 5 min. The solution is allowed to warm to ambient temperature. After 20 min, the solutio... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Secondary amide.Primary alcohol | Primary halide | null | null | c1ccccc1 | HO- | C1CCOC1 | null | 0.083333 | COCCOCOc1ccc(I)cc1CO.NC(=O)CCC(=O)NBr>C1CCOC1>COCCOCOc1ccc(I)cc1CBr |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8e6bf9e4d5934b93a925c96b54265e92 | N#Cc1ccc(O)c(CN2CCC(N)C2=O)c1.O=S(=O)(Cl)c1cc2c(Cl)cc(Cl)cc2s1>>N#Cc1ccc(O)c(CN2CCC(NS(=O)(=O)c3cc4c(Cl)cc(Cl)cc4s3)C2=O)c1 | Cl.NC1C(N(CC1)CC=1C=C(C#N)C=CC1O)=O.ClC1=CC(=CC=2SC(=CC21)S(=O)(=O)Cl)Cl>>OC1=C(CN2C(C(CC2)NS(=O)(=O)C2=CC3=C(S2)C=C(C=C3Cl)Cl)=O)C=C(C=C1)C#N | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[c:8]([CH2:9][N:10]2[CH2:11][CH2:12][CH:13]([NH2:14])[C:29]2=[O:30])[cH:31]1.Cl[S:15](=[O:16])(=[O:17])[c:18]1[cH:19][c:20]2[c:21]([Cl:22])[cH:23][c:24]([Cl:25])[cH:26][c:27]2[s:28]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[c:8]([CH2:9][N:10]2[CH2:11][CH2:12][CH:13]([NH:14][... | N#Cc1ccc(O)c(CN2CCC(N)C2=O)c1.O=S(=O)(Cl)c1cc2c(Cl)cc(Cl)cc2s1 | N#Cc1ccc(O)c(CN2CCC(NS(=O)(=O)c3cc4c(Cl)cc(Cl)cc4s3)C2=O)c1 | null | null | N1=CC=CC=C1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C1C(NS(=O)(=O)c2cc3ccccc3s2)CCN1Cc1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[#16;a:6]:[c:7].[C:8]-[#7:9]1-[C:10]-[C:11]-[C:12](-[NH2;D1;+0:13])-[C:14]-1=[O;D1;H0:15]>>[C:8]-[#7:9]1-[C:10]-[C:11]-[C:12](-[NH;D2;+0:13]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[#16;a:6]:[c:7])-[C:14]-1=[O;D1;H0:15] | null | [] | null | null | 6 | HOUR | To a solution of 3-[(3-amino-2-oxo-pyrrolidin-1-yl)-methyl]-4-hydroxy-benzonitrile hydrochloride (0.20 g, 0.75 mmol) in 3 mL of pyridine at 0° C. is added 4,6-dichlorobenzo[b]thiophene-2-sulfonyl chloride. The solution is allowed to warm to ambient temperatures and is stirred for 6 h. After this time, the solution is c... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.C1CC[NH]C1.c1ccc2sccc2c1 | HCl | N1=CC=CC=C1 | null | 6 | N#Cc1ccc(O)c(CN2CCC(N)C2=O)c1.O=S(=O)(Cl)c1cc2c(Cl)cc(Cl)cc2s1>N1=CC=CC=C1>N#Cc1ccc(O)c(CN2CCC(NS(=O)(=O)c3cc4c(Cl)cc(Cl)cc4s3)C2=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1904bdb207a945399ea4b67f6fd8eb2b | O=C(O)C=Cc1cccs1>>O=c1[nH]ccc2sccc12 | S1C(=CC=C1)C=CC(=O)O.C(C)N(CC)CC.C(CCC)N(CCCC)CCCC.[N-]=[N+]=[N-].[Na+].ClC(=O)OCC>>S1C=CC=2C(NC=CC21)=O | O[C:2](=[O:1])[CH:4]=[CH:5][c:6]1[s:7][cH:8][cH:9][cH:10]1>>[O:1]=[c:2]1[nH:3][cH:4][cH:5][c:6]2[s:7][cH:8][cH:9][c:10]12 | O=C(O)C=Cc1cccs1 | O=c1[nH]ccc2sccc12 | null | null | C1(=CC=CC=C1)OC1=CC=CC=C1.O.CC(=O)C | Aromatic Heterocycle Formation | OtherReaction | 54828a5eb96b04385f635b09e9c699fa55ec9027c5a700824956ade8a99bdccd | 9d5f549a93bb7df3bc372c7e0f1ee6b9917d95c912013b318e77400a6ad5952c | O=c1[nH]ccc2sccc12 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D2;+0:3]=[CH;D2;+0:4]-[c:5]1:[#16;a:6]:[c:7]:[c:8]:[cH;D2;+0:9]:1>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[#7;a:10]:[cH;D2;+0:3]:[cH;D2;+0:4]:[c:5]2:[#16;a:6]:[c:7]:[c:8]:[c;H0;D3;+0:9]:2:1 | 49.7 | [{"value": 49.7, "product": "S1C=CC=2C(NC=CC21)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | To a solution of 3-thiophene-2-yl-acrylic acid (7.39 g, 47.9 mmol) in 200 mL of acetone is added triethylamine (4.9 g, 47.9 mmol). The resulting solution is cooled to 0° C. and ethyl chloroformate (5.7 g, 52.8 mmol) is added dropwise. After 2 h, sodium azide (4.67 g, 71.9 mmol) in 25 mL of H2O is then added. The soluti... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | c1ccsc1 | c1nccc2sccc12 | c1nccc2sccc12 | null | C1(=CC=CC=C1)OC1=CC=CC=C1.O.CC(=O)C | 0 | 2 | O=C(O)C=Cc1cccs1>C1(=CC=CC=C1)OC1=CC=CC=C1.O.CC(=O)C>O=c1[nH]ccc2sccc12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-91ec8de0a1e542cc9e6a284639bbfc6c | O=P(Cl)(Cl)Cl.O=c1[nH]ccc2sccc12>>Clc1nccc2sccc12 | S1C=CC=2C(NC=CC21)=O.P(=O)(Cl)(Cl)Cl>>ClC1=NC=CC2=C1C=CS2 | O=P(Cl)(Cl)[Cl:1].O=[c:2]1[nH:3][cH:4][cH:5][c:6]2[s:7][cH:8][cH:9][c:10]12>>[Cl:1][c:2]1[n:3][cH:4][cH:5][c:6]2[s:7][cH:8][cH:9][c:10]12 | O=P(Cl)(Cl)Cl.O=c1[nH]ccc2sccc12 | Clc1nccc2sccc12 | null | null | null | Functional Group Interconversion | OtherReaction | 42c68942de59e6d930c84cbb3b9eb0b91e5428d9560f2ecf517feddb81854e5e | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1cc2sccc2cn1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4]:[c:5]:[c:6]2:[#16;a:7]:[c:8]:[c:9]:[c:10]:2:1>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c:4]:[c:5]:[c:6]2:[#16;a:7]:[c:8]:[c:9]:[c:10]:2:1 | null | [] | 100 | CELSIUS | 4 | HOUR | 5H-Thieno[3,2-c]pyridin-4-one (1.0 g, 6.62 mmol) is dissolved in 30 mL of phosphorous oxy chloride. The solution is heated to 100° C. After 4 h, the solution is concentrated. The residue is dissolved in CH2 Cl2. The resulting solution is washed with water and saturated NaCl. The organic layer is dried over MgSO4, filte... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1nccc2sccc12 | c1cc2sccc2cn1 | c1cc2sccc2cn1 | HCl | null | 100 | 4 | O=P(Cl)(Cl)Cl.O=c1[nH]ccc2sccc12>>Clc1nccc2sccc12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e0b43900a7e1454399672e06b3cc15d4 | N#Cc1cccc(CN2CC[C@H](N)C2=O)c1.O=S(=O)(Cl)c1cc2nc(Cl)ccc2s1>>N#Cc1cccc(CN2CC[C@H](NS(=O)(=O)c3cc4nc(Cl)ccc4s3)C2=O)c1 | ClC1=CC=C2C(=N1)C=C(S2)S(=O)(=O)Cl.Cl.N[C@@H]1C(N(CC1)CC=1C=C(C#N)C=CC1)=O>>C(#N)C=1C=C(CN2C([C@H](CC2)NS(=O)(=O)C2=CC3=NC(=CC=C3S2)Cl)=O)C=CC1 | [N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][N:9]2[CH2:10][CH2:11][C@H:12]([NH2:13])[C:27]2=[O:28])[cH:29]1.Cl[S:14](=[O:15])(=[O:16])[c:17]1[cH:18][c:19]2[n:20][c:21]([Cl:22])[cH:23][cH:24][c:25]2[s:26]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][N:9]2[CH2:10][CH2:11][C@H:12]([NH:13][S:14](=[O:15])(=[O:16])... | N#Cc1cccc(CN2CC[C@H](N)C2=O)c1.O=S(=O)(Cl)c1cc2nc(Cl)ccc2s1 | N#Cc1cccc(CN2CC[C@H](NS(=O)(=O)c3cc4nc(Cl)ccc4s3)C2=O)c1 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C1[C@@H](NS(=O)(=O)c2cc3ncccc3s2)CCN1Cc1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4]1:[#16;a:5]:[c:6]:[c:7](:[#7;a:8]):[c:9]:1.[C:10]-[#7:11]1-[C:12]-[C:13]-[C:14](-[NH2;D1;+0:15])-[C:16]-1=[O;D1;H0:17]>>[#7;a:8]:[c:7]1:[c:9]:[c:4](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[NH;D2;+0:15]-[C:14]2-[C:13]-[C:12]-[#7:11](-[C:10])-[C:16]-2=[O;D1;H0:17]):[... | null | [] | null | null | null | null | The title compound is prepared from 3-(3-(S)-amino-2-oxo-pyrrolidin-1-ylmethyl)-benzonitrile hydrochloride as described in EXAMPLE 1, Part E using 5-chlorothieno[3,2-b]pyridine-2-sulfonyl chloride in place of benzo[b]thiophene-2sulfonyl chloride. The product is obtained as a white solid.
Conditions: See reaction.notes.... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.C1CC[NH]C1.c1cnc2ccsc2c1 | HCl | null | null | null | N#Cc1cccc(CN2CC[C@H](N)C2=O)c1.O=S(=O)(Cl)c1cc2nc(Cl)ccc2s1>>N#Cc1cccc(CN2CC[C@H](NS(=O)(=O)c3cc4nc(Cl)ccc4s3)C2=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e34502d7c6c04c4ba22048fd23ff4bf0 | CI.N#Cc1cccc(CN2CC[C@H](NS(=O)(=O)c3cc4nc(Cl)ccc4s3)C2=O)c1>>CN([C@H]1CCN(Cc2cccc(C#N)c2)C1=O)S(=O)(=O)c1cc2nc(Cl)ccc2s1 | CCOC(=O)C.CI.[H-].[Na+].C(#N)C=1C=C(CN2C([C@H](CC2)NS(=O)(=O)C2=CC3=NC(=CC=C3S2)Cl)=O)C=CC1>>C(#N)C=1C=C(CN2C([C@H](CC2)N(S(=O)(=O)C2=CC3=NC(=CC=C3S2)Cl)C)=O)C=CC1 | I[CH3:1].[NH:2]([C@H:3]1[CH2:4][CH2:5][N:6]([CH2:7][c:8]2[cH:9][cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15]2)[C:16]1=[O:17])[S:18](=[O:19])(=[O:20])[c:21]1[cH:22][c:23]2[n:24][c:25]([Cl:26])[cH:27][cH:28][c:29]2[s:30]1>>[CH3:1][N:2]([C@H:3]1[CH2:4][CH2:5][N:6]([CH2:7][c:8]2[cH:9][cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15]... | CI.N#Cc1cccc(CN2CC[C@H](NS(=O)(=O)c3cc4nc(Cl)ccc4s3)C2=O)c1 | CN([C@H]1CCN(Cc2cccc(C#N)c2)C1=O)S(=O)(=O)c1cc2nc(Cl)ccc2s1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | c6ca050f6d67acb7bc6fc8b4d7848b3f349e4e8db81643cbb6d12b5a34cbf965 | 9d3dfd18cb6410898a6d822a6d80081d602cf34984cafbfa56b84aa4b38ddbf6 | O=C1[C@@H](NS(=O)(=O)c2cc3ncccc3s2)CCN1Cc1ccccc1 | I-[CH3;D1;+0:1].[#16;a:2]:[c:3]-[#16:4](=[O;D1;H0:5])(=[O;D1;H0:6])-[NH;D2;+0:7]-[C:8]1-[C:9]-[C:10]-[#7:11](-[C:12])-[C:13]-1=[O;D1;H0:14]>>[#16;a:2]:[c:3]-[#16:4](=[O;D1;H0:5])(=[O;D1;H0:6])-[N;H0;D3;+0:7](-[CH3;D1;+0:1])-[C:8]1-[C:9]-[C:10]-[#7:11](-[C:12])-[C:13]-1=[O;D1;H0:14] | null | [] | 0 | CELSIUS | 2 | HOUR | 5-Chlorothieno[3,2-b]pyridine-2-sulfonic acid [1-(3-cyanobenzyl)-2-oxo-pyrrolidin-3-(S)-yl]-amide (0.25 g, 0.56 mmol) is dissolved in 6 mL of DMF and cooled to 0° C. To the solution is added methyl iodide (0.40 g, 2.82 mmol) and sodium hydride (25 mg of a 60% dispersion in mineral oil, 0.62 mmol). The reaction mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Tertiary amine | null | null | C1CC[NH]C1.c1ccccc1.c1cnc2ccsc2c1 | HI | CN(C)C=O | 0 | 2 | CI.N#Cc1cccc(CN2CC[C@H](NS(=O)(=O)c3cc4nc(Cl)ccc4s3)C2=O)c1>CN(C)C=O>CN([C@H]1CCN(Cc2cccc(C#N)c2)C1=O)S(=O)(=O)c1cc2nc(Cl)ccc2s1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3fd33ae5f6e6424f853b83bed699d2ad | N#Cc1cccc(CN2CC[C@H](N)C2=O)c1.O=S(=O)(Cl)c1cc2ccc(Cl)nc2s1>>N#Cc1cccc(CN2CC[C@H](NS(=O)(=O)c3cc4ccc(Cl)nc4s3)C2=O)c1 | ClC1=CC=C2C(=N1)SC(=C2)S(=O)(=O)Cl.Cl.N[C@@H]1C(N(CC1)CC=1C=C(C#N)C=CC1)=O>>C(#N)C=1C=C(CN2C([C@H](CC2)NS(=O)(=O)C2=CC=3C(=NC(=CC3)Cl)S2)=O)C=CC1 | [N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][N:9]2[CH2:10][CH2:11][C@H:12]([NH2:13])[C:27]2=[O:28])[cH:29]1.Cl[S:14](=[O:15])(=[O:16])[c:17]1[cH:18][c:19]2[cH:20][cH:21][c:22]([Cl:23])[n:24][c:25]2[s:26]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][N:9]2[CH2:10][CH2:11][C@H:12]([NH:13][S:14](=[O:15])(=[O:16])... | N#Cc1cccc(CN2CC[C@H](N)C2=O)c1.O=S(=O)(Cl)c1cc2ccc(Cl)nc2s1 | N#Cc1cccc(CN2CC[C@H](NS(=O)(=O)c3cc4ccc(Cl)nc4s3)C2=O)c1 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C1[C@@H](NS(=O)(=O)c2cc3cccnc3s2)CCN1Cc1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[#16;a:6]:[c:7]:[#7;a:8].[C:9]-[#7:10]1-[C:11]-[C:12]-[C:13](-[NH2;D1;+0:14])-[C:15]-1=[O;D1;H0:16]>>[#7;a:8]:[c:7]:[#16;a:6]:[c:4](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[NH;D2;+0:14]-[C:13]1-[C:12]-[C:11]-[#7:10](-[C:9])-[C:15]-1=[O;D1;H0:16]):[c:5] | null | [] | null | null | null | null | The title compound is prepared from 3-(3-(S)-amino-2-oxo-pyrrolidin-1-ylmethyl)-benzonitrile hydrochloride as described in EXAMPLE 1, Part E using 6-chlorothieno[2,3-b]pyridine-2-sulfonyl chloride in place of benzo[b]thiophene-2-sulfonyl chloride. The crude product is purified by column chromatography eluting with a gr... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.C1CC[NH]C1.c1cnc2sccc2c1 | HCl | null | null | null | N#Cc1cccc(CN2CC[C@H](N)C2=O)c1.O=S(=O)(Cl)c1cc2ccc(Cl)nc2s1>>N#Cc1cccc(CN2CC[C@H](NS(=O)(=O)c3cc4ccc(Cl)nc4s3)C2=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7d83168d7ce54c43b52724a182b35f94 | N#Cc1ccc(O)c(CN2CC[C@H](N)C2=O)c1.O=S(=O)(Cl)c1cc2nc(Cl)ccc2s1>>N#Cc1ccc(O)c(CN2CC[C@H](NS(=O)(=O)c3cc4nc(Cl)ccc4s3)C2=O)c1 | ClC1=CC=C2C(=N1)C=C(S2)S(=O)(=O)Cl.Cl.OC1=C(C=C(C#N)C=C1)CN1C([C@H](CC1)N)=O>>C(#N)C=1C=CC(=C(CN2C([C@H](CC2)NS(=O)(=O)C2=CC3=NC(=CC=C3S2)Cl)=O)C1)O | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[c:8]([CH2:9][N:10]2[CH2:11][CH2:12][C@H:13]([NH2:14])[C:28]2=[O:29])[cH:30]1.Cl[S:15](=[O:16])(=[O:17])[c:18]1[cH:19][c:20]2[n:21][c:22]([Cl:23])[cH:24][cH:25][c:26]2[s:27]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[c:8]([CH2:9][N:10]2[CH2:11][CH2:12][C@H:13]([NH:14][S:15](=... | N#Cc1ccc(O)c(CN2CC[C@H](N)C2=O)c1.O=S(=O)(Cl)c1cc2nc(Cl)ccc2s1 | N#Cc1ccc(O)c(CN2CC[C@H](NS(=O)(=O)c3cc4nc(Cl)ccc4s3)C2=O)c1 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C1[C@@H](NS(=O)(=O)c2cc3ncccc3s2)CCN1Cc1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4]1:[#16;a:5]:[c:6]:[c:7](:[#7;a:8]):[c:9]:1.[C:10]-[#7:11]1-[C:12]-[C:13]-[C:14](-[NH2;D1;+0:15])-[C:16]-1=[O;D1;H0:17]>>[#7;a:8]:[c:7]1:[c:9]:[c:4](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[NH;D2;+0:15]-[C:14]2-[C:13]-[C:12]-[#7:11](-[C:10])-[C:16]-2=[O;D1;H0:17]):[... | null | [] | null | null | null | null | The title compound is prepared from 4-hydroxy-3-(3-(S)-amino-2-oxo-pyrrolidin-1-ylmethyl)-benzonitrile hydrochloride as described in EXAMPLE 17, Part F using 5-chlorothieno[3,2-b]pyridine-2-sulfonyl chloride in place of 4,6-dichlorobenzo[b]thiophene-2-sulfonyl chloride. The product is obtained as a white solid.
Conditi... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.C1CC[NH]C1.c1cnc2ccsc2c1 | HCl | null | null | null | N#Cc1ccc(O)c(CN2CC[C@H](N)C2=O)c1.O=S(=O)(Cl)c1cc2nc(Cl)ccc2s1>>N#Cc1ccc(O)c(CN2CC[C@H](NS(=O)(=O)c3cc4nc(Cl)ccc4s3)C2=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-da66f9befd2a4203a17ae478295b584e | N#Cc1ccc(N)c(CN2CC[C@H](N)C2=O)c1.O=S(=O)(Cl)c1cc2nc(Cl)ccc2s1>>N#Cc1ccc(N)c(CN2CC[C@H](NS(=O)(=O)c3cc4nc(Cl)ccc4s3)C2=O)c1 | ClC1=CC=C2C(=N1)C=C(S2)S(=O)(=O)Cl.Cl.Cl.NC1=C(C=C(C#N)C=C1)CN1C([C@H](CC1)N)=O>>NC1=C(CN2C([C@H](CC2)NS(=O)(=O)C2=CC3=NC(=CC=C3S2)Cl)=O)C=C(C=C1)C#N | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[c:8]([CH2:9][N:10]2[CH2:11][CH2:12][C@H:13]([NH2:14])[C:28]2=[O:29])[cH:30]1.Cl[S:15](=[O:16])(=[O:17])[c:18]1[cH:19][c:20]2[n:21][c:22]([Cl:23])[cH:24][cH:25][c:26]2[s:27]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[c:8]([CH2:9][N:10]2[CH2:11][CH2:12][C@H:13]([NH:14][S:15]... | N#Cc1ccc(N)c(CN2CC[C@H](N)C2=O)c1.O=S(=O)(Cl)c1cc2nc(Cl)ccc2s1 | N#Cc1ccc(N)c(CN2CC[C@H](NS(=O)(=O)c3cc4nc(Cl)ccc4s3)C2=O)c1 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C1[C@@H](NS(=O)(=O)c2cc3ncccc3s2)CCN1Cc1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4]1:[#16;a:5]:[c:6]:[c:7](:[#7;a:8]):[c:9]:1.[C:10]-[#7:11]1-[C:12]-[C:13]-[C:14](-[NH2;D1;+0:15])-[C:16]-1=[O;D1;H0:17]>>[#7;a:8]:[c:7]1:[c:9]:[c:4](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[NH;D2;+0:15]-[C:14]2-[C:13]-[C:12]-[#7:11](-[C:10])-[C:16]-2=[O;D1;H0:17]):[... | null | [] | null | null | null | null | The title compound is prepared from 4-amino-3-(3-(S)-amino-2-oxo-pyrrolidin-1-ylmethyl)-benzonitrile dihydrochloride as described in EXAMPLE 17, Part F using 5-chlorothieno[3,2-b]pyridine-2-sulfonyl chloride in place of 4,6-dichlorobenzo[b]thiophene-2-sulfonyl chloride. The crude product is purified by column chromatog... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.C1CC[NH]C1.c1cnc2ccsc2c1 | HCl | null | null | null | N#Cc1ccc(N)c(CN2CC[C@H](N)C2=O)c1.O=S(=O)(Cl)c1cc2nc(Cl)ccc2s1>>N#Cc1ccc(N)c(CN2CC[C@H](NS(=O)(=O)c3cc4nc(Cl)ccc4s3)C2=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-394fa6eeedf64e31a0dbc91c22f2c1e3 | N#Cc1cc(CN2CC[C@H](N)C2=O)cs1.O=S(=O)(Cl)c1cc2nc(Cl)ccc2s1>>N#Cc1cc(CN2CC[C@H](NS(=O)(=O)c3cc4nc(Cl)ccc4s3)C2=O)cs1 | ClC1=CC=C2C(=N1)C=C(S2)S(=O)(=O)Cl.Cl.N[C@@H]1C(N(CC1)CC=1C=C(SC1)C#N)=O>>C(#N)C1=CC(=CS1)CN1C([C@H](CC1)NS(=O)(=O)C1=CC2=NC(=CC=C2S1)Cl)=O | [N:1]#[C:2][c:3]1[cH:4][c:5]([CH2:6][N:7]2[CH2:8][CH2:9][C@H:10]([NH2:11])[C:25]2=[O:26])[cH:27][s:28]1.Cl[S:12](=[O:13])(=[O:14])[c:15]1[cH:16][c:17]2[n:18][c:19]([Cl:20])[cH:21][cH:22][c:23]2[s:24]1>>[N:1]#[C:2][c:3]1[cH:4][c:5]([CH2:6][N:7]2[CH2:8][CH2:9][C@H:10]([NH:11][S:12](=[O:13])(=[O:14])[c:15]3[cH:16][c:17]4[... | N#Cc1cc(CN2CC[C@H](N)C2=O)cs1.O=S(=O)(Cl)c1cc2nc(Cl)ccc2s1 | N#Cc1cc(CN2CC[C@H](NS(=O)(=O)c3cc4nc(Cl)ccc4s3)C2=O)cs1 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C1[C@@H](NS(=O)(=O)c2cc3ncccc3s2)CCN1Cc1ccsc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4]1:[#16;a:5]:[c:6]:[c:7](:[#7;a:8]):[c:9]:1.[C:10]-[#7:11]1-[C:12]-[C:13]-[C:14](-[NH2;D1;+0:15])-[C:16]-1=[O;D1;H0:17]>>[#7;a:8]:[c:7]1:[c:9]:[c:4](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[NH;D2;+0:15]-[C:14]2-[C:13]-[C:12]-[#7:11](-[C:10])-[C:16]-2=[O;D1;H0:17]):[... | null | [] | null | null | null | null | The title compound is prepared from 4-(3-(S)-amino-2-oxo-pyrrolidin-1-ylmethyl)-thiophene-2carbonitrile hydrochloride as described in EXAMPLE 1, Part E using 5-chlorothieno[3,2-b]pyridine-2-sulfonyl chloride in place of benzo[b]thiophene-2-sulfonyl chloride. The product is triturated with Et2O/CH2Cl2 /hexanes to give a... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccsc1.C1CC[NH]C1.c1cnc2ccsc2c1 | HCl | null | null | null | N#Cc1cc(CN2CC[C@H](N)C2=O)cs1.O=S(=O)(Cl)c1cc2nc(Cl)ccc2s1>>N#Cc1cc(CN2CC[C@H](NS(=O)(=O)c3cc4nc(Cl)ccc4s3)C2=O)cs1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-60b484981a1542b5a69074c8e93eaa5c | CS(=O)(=O)c1nccc(-c2ccc(S(=O)(=O)N[C@H]3CCN(Cc4cccc(C#N)c4)C3=O)s2)n1.CS(=O)c1nccc(-c2ccc(S(=O)(=O)N[C@H]3CCN(Cc4cccc(C#N)c4)C3=O)s2)n1>>N#Cc1cccc(CN2CC[C@H](NS(=O)(=O)c3ccc(-c4ccnc(N)n4)s3)C2=O)c1 | C(#N)C=1C=C(CN2C([C@H](CC2)NS(=O)(=O)C=2SC(=CC2)C2=NC(=NC=C2)S(=O)C)=O)C=CC1.C(#N)C=1C=C(CN2C([C@H](CC2)NS(=O)(=O)C=2SC(=CC2)C2=NC(=NC=C2)S(=O)(=O)C)=O)C=CC1>>C(#N)C=1C=C(CN2C([C@H](CC2)NS(=O)(=O)C=2SC(=CC2)C2=NC(=NC=C2)N)=O)C=CC1 | CS(=O)(=O)[c:25]1[n:24][cH:23][cH:22][c:21](-[c:20]2[cH:19][cH:18][c:17]([S:14]([NH:13][C@H:12]3[CH2:11][CH2:10][N:9]([CH2:8][c:7]4[cH:6][cH:5][cH:4][c:3]([C:2]#[N:1])[cH:31]4)[C:29]3=[O:30])(=[O:15])=[O:16])[s:28]2)[n:27]1.CS(=O)c1nccc(-c2ccc(S(=O)(=O)N[C@H]3CCN(Cc4cccc(C#[N:26])c4)C3=O)s2)n1>>[N:1]#[C:2][c:3]1[cH:4][... | CS(=O)(=O)c1nccc(-c2ccc(S(=O)(=O)N[C@H]3CCN(Cc4cccc(C#N)c4)C3=O)s2)n1.CS(=O)c1nccc(-c2ccc(S(=O)(=O)N[C@H]3CCN(Cc4cccc(C#N)c4)C3=O)s2)n1 | N#Cc1cccc(CN2CC[C@H](NS(=O)(=O)c3ccc(-c4ccnc(N)n4)s3)C2=O)c1 | null | null | CCO | Heteroatom Alkylation and Arylation | OtherReaction | 54eab23b3237332c5d911f55f8de73819a92e25047c9befc930c43eb534fca94 | 6f8c87b921d87706e8de9cc2c402f07b60f84539e4d441961d16151021dfe716 | O=C1[C@@H](NS(=O)(=O)c2ccc(-c3ccncn3)s2)CCN1Cc1ccccc1 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].C-S(=O)-c1:n:c:c:c(-c2:c:c:c(-S(=O)(=O)-N-[C@@H]3-C-C-N(-C-c4:c:c:c:c(-C#[N;H0;D1;+0:6]):c:4)-C-3=O):s:2):n:1>>[NH2;D1;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | null | [] | 90 | CELSIUS | null | null | A mixture of [5-(2-methylsulfinyl-pyrimidin-4-yl)-thiophene-2-sulfonic acid [1-(3-cyanobenzyl)-2-oxo-pyrrolidin3-(S)-yl]-amide and [5-(2-methylsulfonyl-pyrimidin-4-yl)-thiophene-2sulfonic acid [1-(3-cyanobenzyl)-2-oxo-pyrrolidin-3-(S)-yl]-amide (0.20 g, 0.39 mmol) is dissolved in 10 mL of EtOH and NH3 gas is bubbled th... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Nitrile.Tertiary amide.Sulfone.Sulfoxide | Primary amine | c1cncnc1.c1cncnc1.c1ccsc1.C1CCNC1.c1ccccc1 | c1cncnc1 | c1ccccc1.C1CC[NH]C1.c1ccsc1.c1cncnc1 | Other | CCO | 90 | null | CS(=O)(=O)c1nccc(-c2ccc(S(=O)(=O)N[C@H]3CCN(Cc4cccc(C#N)c4)C3=O)s2)n1.CS(=O)c1nccc(-c2ccc(S(=O)(=O)N[C@H]3CCN(Cc4cccc(C#N)c4)C3=O)s2)n1>CCO>N#Cc1cccc(CN2CC[C@H](NS(=O)(=O)c3ccc(-c4ccnc(N)n4)s3)C2=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c424644c1b9d4f20a208e338fe1bae0a | N#Cc1cccc(CN2CC[C@H](N)C2=O)c1.O=S(=O)(Cl)c1ccc(-c2ccc(Cl)s2)s1>>N#Cc1cccc(CN2CC[C@H](NS(=O)(=O)c3ccc(-c4ccc(Cl)s4)s3)C2=O)c1 | ClC1=CC=C(S1)C=1SC(=CC1)S(=O)(=O)Cl.Cl.N[C@@H]1C(N(CC1)CC=1C=C(C#N)C=CC1)=O>>C(#N)C=1C=C(CN2C([C@H](CC2)NS(=O)(=O)C2=CC=C(S2)C=2SC(=CC2)Cl)=O)C=CC1 | [N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][N:9]2[CH2:10][CH2:11][C@H:12]([NH2:13])[C:28]2=[O:29])[cH:30]1.Cl[S:14](=[O:15])(=[O:16])[c:17]1[cH:18][cH:19][c:20](-[c:21]2[cH:22][cH:23][c:24]([Cl:25])[s:26]2)[s:27]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][N:9]2[CH2:10][CH2:11][C@H:12]([NH:13][S:14](=[O:15]... | N#Cc1cccc(CN2CC[C@H](N)C2=O)c1.O=S(=O)(Cl)c1ccc(-c2ccc(Cl)s2)s1 | N#Cc1cccc(CN2CC[C@H](NS(=O)(=O)c3ccc(-c4ccc(Cl)s4)s3)C2=O)c1 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C1[C@@H](NS(=O)(=O)c2ccc(-c3cccs3)s2)CCN1Cc1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[#16;a:6]:[c:7].[C:8]-[#7:9]1-[C:10]-[C:11]-[C:12](-[NH2;D1;+0:13])-[C:14]-1=[O;D1;H0:15]>>[C:8]-[#7:9]1-[C:10]-[C:11]-[C:12](-[NH;D2;+0:13]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[#16;a:6]:[c:7])-[C:14]-1=[O;D1;H0:15] | null | [] | null | null | null | null | The title compound is prepared from 3-(3-(S)-amino-2-oxo-pyrrolidin-1-ylmethyl)-benzonitrile hydrochloride as described in EXAMPLE 1, Part E using 5'-chloro-[2,2']bithiophenyl-5-sulfonyl chloride in place of benzo[b]thiophene-2-sulfonyl chloride. The crude product is triturated with EtOAc/CH2Cl2 to yield a beige solid.... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.C1CC[NH]C1.c1ccsc1.c1ccsc1 | HCl | null | null | null | N#Cc1cccc(CN2CC[C@H](N)C2=O)c1.O=S(=O)(Cl)c1ccc(-c2ccc(Cl)s2)s1>>N#Cc1cccc(CN2CC[C@H](NS(=O)(=O)c3ccc(-c4ccc(Cl)s4)s3)C2=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2304608b9689445eb80f2a17289a2a83 | N#Cc1ccc(N)c(CN2CC[C@H](N)C2=O)c1.O=S(=O)(Cl)c1cc2ccccc2s1>>N#Cc1cc(CN2CC[C@H](NS(=O)(=O)c3cc4ccccc4s3)C2=O)ccc1N | Cl.Cl.NC1=C(C=C(C#N)C=C1)CN1C([C@H](CC1)N)=O.S1C2=C(C=C1S(=O)(=O)Cl)C=CC=C2.C(C)#N>>NC1=C(C=C(CN2C([C@H](CC2)NS(=O)(=O)C2=CC3=C(S2)C=CC=C3)=O)C=C1)C#N | [N:1]#[C:2][c:3]1[cH:4][c:5]([CH2:6][N:7]2[CH2:8][CH2:9][C@H:10]([NH2:11])[C:24]2=[O:25])[c:28]([NH2:29])[cH:27][cH:26]1.Cl[S:12](=[O:13])(=[O:14])[c:15]1[cH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2[s:23]1>>[N:1]#[C:2][c:3]1[cH:4][c:5]([CH2:6][N:7]2[CH2:8][CH2:9][C@H:10]([NH:11][S:12](=[O:13])(=[O:14])[c:15]3[cH:1... | N#Cc1ccc(N)c(CN2CC[C@H](N)C2=O)c1.O=S(=O)(Cl)c1cc2ccccc2s1 | N#Cc1cc(CN2CC[C@H](NS(=O)(=O)c3cc4ccccc4s3)C2=O)ccc1N | null | null | null | Acylation | OtherReaction | 865d2c7ca0b2405c43aad840bd1da2da815f90bc528694bbf6f112a385856db3 | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C1[C@@H](NS(=O)(=O)c2cc3ccccc3s2)CCN1Cc1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[#16;a:6]:[c:7].[N;D1;H0:8]#[C:9]-[c;H0;D3;+0:10]1:[c:11]:[c;H0;D3;+0:12](-[C:13]-[#7:14]2-[C:15]-[C:16]-[C:17](-[NH2;D1;+0:18])-[C:19]-2=[O;D1;H0:20]):[c;H0;D3;+0:21](-[N;D1;H2:22]):[c:23]:[cH;D2;+0:24]:1>>[N;D1;H0:8]#[C:9]-[c;H0;D3;+0:10]1:[c:11]:[c;H0;D3;+0... | null | [] | null | null | null | null | The title compound (0.131 g, 0.307 mmol) is prepared as in EXAMPLE 1, Part E from 4-amino-3-(3-(S)-amino-2-oxo-pyrrolidin-1-ylmethyl)benzonitrile dihydrochloride (0.135 g, 0.445 mmol) and benzo[b]thiophene-2-sulfonyl chloride (0.114 g, 0.49 mmol) in acetonitrile.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CC[NH]C1.c1ccc2sccc2c1 | HCl | null | null | null | N#Cc1ccc(N)c(CN2CC[C@H](N)C2=O)c1.O=S(=O)(Cl)c1cc2ccccc2s1>>N#Cc1cc(CN2CC[C@H](NS(=O)(=O)c3cc4ccccc4s3)C2=O)ccc1N |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8d5d986597254a4b95b496e32a884a31 | Brc1cccnc1.OB(O)c1cccs1>>c1cncc(-c2cccs2)c1 | BrC=1C=NC=CC1.S1C(=CC=C1)B(O)O.C([O-])([O-])=O.[Na+].[Na+]>>S1C(=CC=C1)C=1C=NC=CC1 | Br[c:5]1[cH:4][n:3][cH:2][cH:1][cH:11]1.OB(O)[c:6]1[cH:7][cH:8][cH:9][s:10]1>>[cH:1]1[cH:2][n:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][s:10]2)[cH:11]1 | Brc1cccnc1.OB(O)c1cccs1 | c1cncc(-c2cccs2)c1 | null | null | C(OC)COC | C-C Coupling | Suzuki coupling with boronic acids | 4843472bfbf876bd84b6771e3b8ba0d5e71e698fe8e6f3b53c129c420510bd0d | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1cncc(-c2cccs2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.O-B(-O)-[c;H0;D3;+0:7]1:[#16;a:8]:[c:9]:[c:10]:[c:11]:1>>[#16;a:8]1:[c:9]:[c:10]:[c:11]:[c;H0;D3;+0:7]:1-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1 | 16.3 | [{"value": 16.3, "product": "S1C(=CC=C1)C=1C=NC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | A mixture of 3-bromopyridine (1.30 mL, 13.5 mmol) and tetrakis(triphenylphosphine) (0.468 g, 0.41 mmol) in 40 mL of dimethoxyethane is stirred under nitrogen at room temperature for 10 min. 2-Thiophene boronic acid (1.90 g, 14.8 mmol) and 20 mL of 1N sodium carbonate are added and the resulting mixture is refluxed over... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccncc1.c1ccsc1 | c1ccncc1.c1ccsc1 | c1ccncc1.c1ccsc1 | HBr.B | C(OC)COC | null | 0.166667 | Brc1cccnc1.OB(O)c1cccs1>C(OC)COC>c1cncc(-c2cccs2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-385105c7ada24b3c981f877c5e6c950f | O=S(=O)(Cl)Cl.c1cncc(-c2cccs2)c1>>O=S(=O)(Cl)c1ccc(-c2cccnc2)s1 | S(=O)(=O)(Cl)Cl.S1C(=CC=C1)C=1C=NC=CC1.[Li]CCCC.C(Cl)Cl>>N1=CC(=CC=C1)C1=CC=C(S1)S(=O)(=O)Cl | Cl[S:2](=[O:1])(=[O:3])[Cl:4].[cH:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][n:13][cH:14]2)[s:15]1>>[O:1]=[S:2](=[O:3])([Cl:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][n:13][cH:14]2)[s:15]1 | O=S(=O)(Cl)Cl.c1cncc(-c2cccs2)c1 | O=S(=O)(Cl)c1ccc(-c2cccnc2)s1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 8262cd7e2fb49c292864204e18c959a9ad65e1b79f29da3707f938430466ad5f | d32b60b8f9bfd187c6c9f1eef6a22a00f53525a7532b83aba763d5389c9e4280 | c1cncc(-c2cccs2)c1 | Cl-[S;H0;D4;+0:1](-[Cl;D1;H0:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#16;a:5]1:[c:6]:[c:7]:[c:8]:[cH;D2;+0:9]:1>>[Cl;D1;H0:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[c;H0;D3;+0:9]1:[#16;a:5]:[c:6]:[c:7]:[c:8]:1 | 79.1 | [{"value": 79.1, "product": "N1=CC(=CC=C1)C1=CC=C(S1)S(=O)(=O)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a solution of 3-thiophen-2-yl-pyridine (0.355 g, 2.20 mmol) in 15 mL of THF at -78° C. is added n-BuLi (1.44 mL of a 1.6M solution in hexanes, 2.31 mmol). After stirring for 15 min, SO2 gas is bubbled through the solution for 30 min. The solution is then allowed to warm to room temperature and stirred overnight. The... | 10.6084/m9.figshare.5104873.v1 | null | null | Sulfonyl halide | c1ccsc1 | c1ccsc1 | c1ccsc1.c1ccncc1 | HCl | C1CCOC1 | null | 0.25 | O=S(=O)(Cl)Cl.c1cncc(-c2cccs2)c1>C1CCOC1>O=S(=O)(Cl)c1ccc(-c2cccnc2)s1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-657035b18b544c1293249703fa8250ea | CC#N.N#Cc1cccc(CN2CC[C@H](N)C2=O)c1.O=S(=O)(Cl)c1ccc(-c2cccnc2)s1>>N#Cc1ccc(N)c(CN2CC[C@H](NS(=O)(=O)c3ccc(-c4cccnc4)s3)C2=O)c1 | N1=CC(=CC=C1)C1=CC=C(S1)S(=O)(=O)Cl.CC#N.Cl.N[C@@H]1C(N(CC1)CC=1C=C(C#N)C=CC1)=O>>NC1=C(CN2C([C@H](CC2)NS(=O)(=O)C=2SC(=CC2)C=2C=NC=CC2)=O)C=C(C=C1)C#N | CC#[N:7].[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:8]([CH2:9][N:10]2[CH2:11][CH2:12][C@H:13]([NH2:14])[C:29]2=[O:30])[cH:31]1.Cl[S:15](=[O:16])(=[O:17])[c:18]1[cH:19][cH:20][c:21](-[c:22]2[cH:23][cH:24][cH:25][n:26][cH:27]2)[s:28]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[c:8]([CH2:9][N:10]2[CH2:11][CH2:12][C@H:13]([NH... | CC#N.N#Cc1cccc(CN2CC[C@H](N)C2=O)c1.O=S(=O)(Cl)c1ccc(-c2cccnc2)s1 | N#Cc1ccc(N)c(CN2CC[C@H](NS(=O)(=O)c3ccc(-c4cccnc4)s3)C2=O)c1 | null | null | null | Acylation | OtherReaction | 8afe1904efc9c56f3a478f1f851926bec9095cb960fe02c612daf3bfd60dfb59 | 580d1fb3543ef370dc3c840c57a206adf6b1dcac30b9008c5ac60289e3adbd76 | O=C1[C@@H](NS(=O)(=O)c2ccc(-c3cccnc3)s2)CCN1Cc1ccccc1 | C-C#[N;H0;D1;+0:1].Cl-[S;H0;D4;+0:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5](:[c:6]):[#16;a:7]:[c:8].[NH2;D1;+0:9]-[C:10]1-[C:11]-[C:12]-[#7:13](-[C:14]-[c:15](:[c:16]):[cH;D2;+0:17]:[c:18]:[c:19])-[C:20]-1=[O;D1;H0:21]>>[NH2;D1;+0:1]-[c;H0;D3;+0:17](:[c:18]:[c:19]):[c:15](-[C:14]-[#7:13]1-[C:12]-[C:11]-[C:10](-[NH;D2;+0:9]-... | null | [] | null | null | null | null | The title compound is prepared in CH3CN instead of CH2Cl2 as described in EXAMPLE 1, Part E using 5-pyridin-3-yl-thiophene-2-sulfonyl choride in place of benzo[b]thiophene-2-sulfonyl chloride and substituting 4-amino-[3-(3-(S)-amino-2-oxo-pyrrolidin-1-ylmethyl)]-benzonitrile dihydrochloride for 3-(3-(S)-amino-2-oxo-pyr... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine.Sulfonyl halide | Sulfonamide.Primary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CC[NH]C1.c1ccsc1.c1ccncc1 | HCl | null | null | null | CC#N.N#Cc1cccc(CN2CC[C@H](N)C2=O)c1.O=S(=O)(Cl)c1ccc(-c2cccnc2)s1>>N#Cc1ccc(N)c(CN2CC[C@H](NS(=O)(=O)c3ccc(-c4cccnc4)s3)C2=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a640257498cc4980927471255d5a0aa0 | CC(C)(C)[Si](C)(C)Cl.N#Cc1ccc(O)c(CN2CCC(NS(=O)(=O)c3ccc(-c4cccnc4)s3)C2=O)c1>>CC(C)(C)[Si](C)(C)Oc1ccc(C#N)cc1CN1CC[C@H](NS(=O)(=O)c2ccc(-c3cccnc3)s2)C1=O | N1C=NC=C1.C(C)(C)(C)[Si](Cl)(C)C.C(#N)C=1C=CC(=C(CN2C(C(CC2)NS(=O)(=O)C=2SC(=CC2)C=2C=NC=CC2)=O)C1)O>>C(C)(C)(C)[Si](OC1=C(CN2C([C@H](CC2)NS(=O)(=O)C=2SC(=CC2)C=2C=NC=CC2)=O)C=C(C=C1)C#N)(C)C | Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][c:9]1[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][c:16]1[CH2:17][N:18]1[CH2:19][CH2:20][CH:21]([NH:22][S:23](=[O:24])(=[O:25])[c:26]2[cH:27][cH:28][c:29](-[c:30]3[cH:31][cH:32][cH:33][n:34][cH:35]3)[s:36]2)[C:37]1=[O:38]>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]... | CC(C)(C)[Si](C)(C)Cl.N#Cc1ccc(O)c(CN2CCC(NS(=O)(=O)c3ccc(-c4cccnc4)s3)C2=O)c1 | CC(C)(C)[Si](C)(C)Oc1ccc(C#N)cc1CN1CC[C@H](NS(=O)(=O)c2ccc(-c3cccnc3)s2)C1=O | null | null | CN(C)C=O.CCOC(=O)C | Protection | Alcohol protection with silyl ethers | 91043baed1393f1ecd2302d7d0b31c01cf171d3977dd7c70afa1da52fa298c73 | 4a917c959d011f885a1269fa3c1f022ee5e09144996246d24e42e65634a451ac | O=C1[C@@H](NS(=O)(=O)c2ccc(-c3cccnc3)s2)CCN1Cc1ccccc1 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C;D1;H3:5]-[C:4](-[C;D1;H3:6])(-[C;D1;H3:7])-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11] | 74.5 | [{"value": 74.5, "product": "C(C)(C)(C)[Si](OC1=C(CN2C([C@H](CC2)NS(=O)(=O)C=2SC(=CC2)C=2C=NC=CC2)=O)C=C(C=C1)C#N)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Imidazole (0.094 g, 1.37 mmol) and t-butyldimethylchlorosilane (0.099 g, 0.66 mmol) are added to a solution of 5-pyridin-3-yl-thiophene-2-sulfonic acid {1-[5-cyano-2-hydroxy-benzyl]-2-oxo-pyrrolidin-3-yl}-amide (0.25 g, 0.55 mmol) in 10 mL of DMF. The resulting mixture is stirred overnight, then diluted with EtOAc and ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Silyl protective group | TMS ether protective group | null | null | c1ccccc1.C1CC[NH]C1.c1ccsc1.c1ccncc1 | HCl | CN(C)C=O.CCOC(=O)C | null | 8 | CC(C)(C)[Si](C)(C)Cl.N#Cc1ccc(O)c(CN2CCC(NS(=O)(=O)c3ccc(-c4cccnc4)s3)C2=O)c1>CN(C)C=O.CCOC(=O)C>CC(C)(C)[Si](C)(C)Oc1ccc(C#N)cc1CN1CC[C@H](NS(=O)(=O)c2ccc(-c3cccnc3)s2)C1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a753907ee0d040cd8bed715a621a022d | Clc1cncc(Cl)c1.OB(O)c1cccs1>>Clc1cncc(-c2cccs2)c1 | ClC=1C=NC=C(C1)Cl.S1C(=CC=C1)B(O)O>>ClC=1C=C(C=NC1)C=1SC=CC1 | Cl[c:6]1[cH:5][n:4][cH:3][c:2]([Cl:1])[cH:12]1.OB(O)[c:7]1[cH:8][cH:9][cH:10][s:11]1>>[Cl:1][c:2]1[cH:3][n:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][s:11]2)[cH:12]1 | Clc1cncc(Cl)c1.OB(O)c1cccs1 | Clc1cncc(-c2cccs2)c1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 4843472bfbf876bd84b6771e3b8ba0d5e71e698fe8e6f3b53c129c420510bd0d | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1cncc(-c2cccs2)c1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.O-B(-O)-[c;H0;D3;+0:7]1:[#16;a:8]:[c:9]:[c:10]:[c:11]:1>>[#16;a:8]1:[c:9]:[c:10]:[c:11]:[c;H0;D3;+0:7]:1-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1 | 16 | [{"value": 16.0, "product": "ClC=1C=C(C=NC1)C=1SC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound (0.21 g, 1.08 mmol) was prepared from 3,5-dichloropyridine (1.0 g, 6.76 mmol) and 2-thiophene boronic acid (0.95 g, 7.43 mmol) as described in EXAMPLE 48, Part B.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccncc1.c1ccsc1 | c1ccncc1.c1ccsc1 | c1ccncc1.c1ccsc1 | HCl.B | null | null | null | Clc1cncc(Cl)c1.OB(O)c1cccs1>>Clc1cncc(-c2cccs2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d795401eb6db4990a351bd0a3efc3fc2 | Brc1cccnc1.Clc1ccsc1>>Clc1ccsc1-c1ccccn1 | ClC1=C(SC=C1)B(O)O.ClC1=CSC=C1.BrC=1C=NC=CC1>>ClC1=C(SC=C1)C1=NC=CC=C1 | Br[c:7]1[cH:8][cH:9][cH:10][n:12][cH:11]1.[Cl:1][c:2]1[cH:3][cH:4][s:5][cH:6]1>>[Cl:1][c:2]1[cH:3][cH:4][s:5][c:6]1-[c:7]1[cH:8][cH:9][cH:10][cH:11][n:12]1 | Brc1cccnc1.Clc1ccsc1 | Clc1ccsc1-c1ccccn1 | null | null | null | C-C Coupling | OtherReaction | 28ca612c50c0f8a71de1ac3bd932995b182c25a058e4478fec3664443b94c68f | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1ccc(-c2cccs2)nc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[cH;D2;+0:4]:[n;H0;D2;+0:5]:[cH;D2;+0:6]:1.[Cl;D1;H0:7]-[c:8]1:[c:9]:[c:10]:[#16;a:11]:[cH;D2;+0:12]:1>>[Cl;D1;H0:7]-[c:8]1:[c:9]:[c:10]:[#16;a:11]:[c;H0;D3;+0:12]:1-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[cH;D2;+0:4]:[cH;D2;+0:6]:[n;H0;D2;+0:5]:1 | 14.2 | [{"value": 14.2, "product": "ClC1=C(SC=C1)C1=NC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-Chlorothiophene-2-boronic acid (1.5 g, 9.24 mmol), prepared as described in EXAMPLE 48, Part A from 3-chlorothiophene was reacted with 3-bromopyridine (0.81 mL, 8.4 mmol) as described in EXAMPLE 48, Part B to give the title compound (0.232 g, 1.19 mmol).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccncc1.c1ccsc1 | c1ccsc1.c1ccncc1 | c1ccsc1.c1ccncc1 | HBr | null | null | null | Brc1cccnc1.Clc1ccsc1>>Clc1ccsc1-c1ccccn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5319433aef944914adab5a67046697cc | N#Cc1ccc(O)c(CN2CCC(N)C2=O)c1.O=S(=O)(Cl)c1cc2ccc(Cl)cc2s1>>N#Cc1ccc(O)c(CN2CC[C@H](NS(=O)(=O)c3cc4ccc(Cl)cc4s3)C2=O)c1 | Cl.NC1C(N(CC1)CC=1C=C(C#N)C=CC1O)=O.ClC=1C=CC2=C(SC(=C2)S(=O)(=O)Cl)C1>>C(#N)C=1C=CC(=C(CN2C([C@H](CC2)NS(=O)(=O)C2=CC3=C(S2)C=C(C=C3)Cl)=O)C1)O | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[c:8]([CH2:9][N:10]2[CH2:11][CH2:12][CH:13]([NH2:14])[C:28]2=[O:29])[cH:30]1.Cl[S:15](=[O:16])(=[O:17])[c:18]1[cH:19][c:20]2[cH:21][cH:22][c:23]([Cl:24])[cH:25][c:26]2[s:27]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[c:8]([CH2:9][N:10]2[CH2:11][CH2:12][C@H:13]([NH:14][S:15](=... | N#Cc1ccc(O)c(CN2CCC(N)C2=O)c1.O=S(=O)(Cl)c1cc2ccc(Cl)cc2s1 | N#Cc1ccc(O)c(CN2CC[C@H](NS(=O)(=O)c3cc4ccc(Cl)cc4s3)C2=O)c1 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C1[C@@H](NS(=O)(=O)c2cc3ccccc3s2)CCN1Cc1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[#16;a:6]:[c:7].[C:8]-[#7:9]1-[C:10]-[C:11]-[CH;D3;+0:12](-[NH2;D1;+0:13])-[C:14]-1=[O;D1;H0:15]>>[C:8]-[#7:9]1-[C:10]-[C:11]-[C@H;D3;+0:12](-[NH;D2;+0:13]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[#16;a:6]:[c:7])-[C:14]-1=[O;D1;H0:15] | null | [] | null | null | null | null | The title compound is prepared from 3-[(3-amino-2-oxo-pyrrolidin-1-yl)-methyl]-4-hydroxy-benzonitrile hydrochloride as described in EXAMPLE 17, Part G substituting 6-chlorobenzo[b]thiophene-2-sulfonyl chloride in place of 4,6-dichlorobenzo[b]thiophene-2-sulfonyl chloride. The crude product is triturated with Et2O to gi... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.C1CC[NH]C1.c1ccc2sccc2c1 | HCl | null | null | null | N#Cc1ccc(O)c(CN2CCC(N)C2=O)c1.O=S(=O)(Cl)c1cc2ccc(Cl)cc2s1>>N#Cc1ccc(O)c(CN2CC[C@H](NS(=O)(=O)c3cc4ccc(Cl)cc4s3)C2=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d723d805d22049e68439ec36653ca220 | O=C(O)CC(=O)O.O=Cc1cccc(Br)c1>>O=C(O)C=Cc1cccc(Br)c1 | BrC=1C=C(C=O)C=CC1.C(CC(=O)O)(=O)O.Cl>>BrC=1C=C(C=CC1)C=CC(=O)O | O=C(O)[CH2:4][C:2](=[O:1])[OH:3].O=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([Br:11])[cH:12]1>>[O:1]=[C:2]([OH:3])[CH:4]=[CH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([Br:11])[cH:12]1 | O=C(O)CC(=O)O.O=Cc1cccc(Br)c1 | O=C(O)C=Cc1cccc(Br)c1 | null | N1CCCCC1 | N1=CC=CC=C1 | C-C Coupling | OtherReaction | 0c2382c2f7ea556671f2a3c58036f5e0661a08f7658c9ccbb421e2a9daac089b | a6032dd2ea62d1cf56f5cee7663c80211fe5b6aa714acc87461f75a8053630fd | c1ccccc1 | O-C(=O)-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[O;D1;H1:4].O=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[O;D1;H0:3]=[C:2](-[O;D1;H1:4])-[CH;D2;+0:1]=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 94.4 | [{"value": 94.4, "product": "BrC=1C=C(C=CC1)C=CC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | 3-Bromobenzaldehyde (10.0 g, 54 mmol), malonic acid (10.1 g, 97 mmol) and piperidine (0.267 mL, 2.7 mmol) are treated with pyridine (30 mL) and heated at 100° C. for 3.5 h. The reaction mixture is cooled to room temperature, poured into 200 ml of 20% hydrochloric acid at 0° C.; the resultant precipitate is collected, w... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Carboxylic acid | null | null | null | c1ccccc1 | HO- | N1CCCCC1.N1=CC=CC=C1 | 100 | null | O=C(O)CC(=O)O.O=Cc1cccc(Br)c1>N1CCCCC1.N1=CC=CC=C1>O=C(O)C=Cc1cccc(Br)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dfa8e518af0e4946b9f86e5f4d0e8666 | O=Cc1cc(Br)ccc1F>>OCc1cc(Br)ccc1F | BrC=1C=CC(=C(C=O)C1)F.[BH4-].[Na+]>>BrC=1C=CC(=C(CO)C1)F | [O:1]=[CH:2][c:3]1[cH:4][c:5]([Br:6])[cH:7][cH:8][c:9]1[F:10]>>[OH:1][CH2:2][c:3]1[cH:4][c:5]([Br:6])[cH:7][cH:8][c:9]1[F:10] | O=Cc1cc(Br)ccc1F | OCc1cc(Br)ccc1F | null | null | C1CCOC1 | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | 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] | 97.7 | [{"value": 97.7, "product": "BrC=1C=CC(=C(CO)C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 25 | MINUTE | To a solution of 5-bromo-2-fluoro-benzaldehyde (6.10 g, 30.0 mmol) in 30 mL of THF at 0° C. is added 5 mL of sodium borohydride (2.0M solution in triglyme, 10.0 mmol). The reaction mixture is stirred at 0° C. for 25 min and then quenched by the addition of 1N HCl. The mixture is diluted with EtOAc and the layers are se... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccccc1 | null | C1CCOC1 | 0 | 0.416667 | O=Cc1cc(Br)ccc1F>C1CCOC1>OCc1cc(Br)ccc1F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-01265d1ee5214b12aaf7fb783abeb10c | O=C1CCC(=O)N1Br.OCc1cc(Br)ccc1F>>Fc1ccc(Br)cc1CBr | BrN1C(CCC1=O)=O.BrC=1C=CC(=C(CO)C1)F.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>BrC=1C=CC(=C(CBr)C1)F | O=C1CCC(=O)N1[Br:10].O[CH2:9][c:8]1[c:2]([F:1])[cH:3][cH:4][c:5]([Br:6])[cH:7]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([Br:6])[cH:7][c:8]1[CH2:9][Br:10] | O=C1CCC(=O)N1Br.OCc1cc(Br)ccc1F | Fc1ccc(Br)cc1CBr | null | null | C1CCOC1 | Functional Group Interconversion | OtherReaction | f5aab884336f72e1370119b83151f1b95e31e5f052f259aee44382a5b9c14686 | 2aeb112456268e3e5dab065a03bb8fc4b6e8f1d07cae05ef26dce278613b654e | c1ccccc1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:5]>>[Br;H0;D1;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 96.7 | [{"value": 96.7, "product": "BrC=1C=CC(=C(CBr)C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | To a solution of 5-bromo-2-fluoro-benzyl alcohol (3.10 g, 15.1 mmol) in 30 mL of THF at 10° C. is added triphenyl phosphine (4.10 g, 15.6 mmol) followed by N-bromosuccinimide (2.67 g, 15.0 mmol). The ice bath is removed and the resulting solution is stirred for 20 min at room temperature. The crude product is purified ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide.Primary alcohol | Primary halide | C1CCNC1 | null | c1ccccc1 | HO- | C1CCOC1 | null | 0.333333 | O=C1CCC(=O)N1Br.OCc1cc(Br)ccc1F>C1CCOC1>Fc1ccc(Br)cc1CBr |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-806352f5d1f24257a0c79e1cedfd6e4a | N#Cc1ccc(F)c(CN2CC[C@H](N)C2=O)c1.O=S(=O)(Cl)c1ccc(-c2cccnc2)s1>>N#Cc1ccc(F)c(CN2CC[C@H](NS(=O)(=O)c3ccc(-c4cccnc4)s3)C2=O)c1 | Cl.N[C@@H]1C(N(CC1)CC=1C=C(C#N)C=CC1F)=O.N1=CC(=CC=C1)C1=CC=C(S1)S(=O)(=O)Cl>>C(#N)C=1C=CC(=C(CN2C([C@H](CC2)NS(=O)(=O)C=2SC(=CC2)C=2C=NC=CC2)=O)C1)F | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([F:7])[c:8]([CH2:9][N:10]2[CH2:11][CH2:12][C@H:13]([NH2:14])[C:29]2=[O:30])[cH:31]1.Cl[S:15](=[O:16])(=[O:17])[c:18]1[cH:19][cH:20][c:21](-[c:22]2[cH:23][cH:24][cH:25][n:26][cH:27]2)[s:28]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([F:7])[c:8]([CH2:9][N:10]2[CH2:11][CH2:12][C@H:13]([NH:14][... | N#Cc1ccc(F)c(CN2CC[C@H](N)C2=O)c1.O=S(=O)(Cl)c1ccc(-c2cccnc2)s1 | N#Cc1ccc(F)c(CN2CC[C@H](NS(=O)(=O)c3ccc(-c4cccnc4)s3)C2=O)c1 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C1[C@@H](NS(=O)(=O)c2ccc(-c3cccnc3)s2)CCN1Cc1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[#16;a:6]:[c:7].[C:8]-[#7:9]1-[C:10]-[C:11]-[C:12](-[NH2;D1;+0:13])-[C:14]-1=[O;D1;H0:15]>>[C:8]-[#7:9]1-[C:10]-[C:11]-[C:12](-[NH;D2;+0:13]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[#16;a:6]:[c:7])-[C:14]-1=[O;D1;H0:15] | null | [] | null | null | null | null | The title compound is prepared from 3-(S)-[(3-amino-2-oxo-pyrrolidin-1-yl)-methyl]-4-fluoro-benzonitrile hydrochloride as described in EXAMPLE 17, Part G substituting 5-pyridin-3-yl-thiophene-2-sulfonyl chloride in place of 4,6-dichlorobenzo[b]thiophene-2-sulfonyl chloride. The crude product is triturated with Et2O to ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.C1CC[NH]C1.c1ccsc1.c1ccncc1 | HCl | null | null | null | N#Cc1ccc(F)c(CN2CC[C@H](N)C2=O)c1.O=S(=O)(Cl)c1ccc(-c2cccnc2)s1>>N#Cc1ccc(F)c(CN2CC[C@H](NS(=O)(=O)c3ccc(-c4cccnc4)s3)C2=O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d45dd22efe384d6e8d41b31969ccab08 | Nc1ccc(Br)cc1.O=C(Cl)C=Cc1ccccc1>>Clc1ccc2cc(Br)ccc2n1.O=c1ccc2cc(Br)ccc2[nH]1 | BrC1=CC=C(N)C=C1.C(C=CC1=CC=CC=C1)(=O)Cl>>ClC1=NC2=CC=C(C=C2C=C1)Br.BrC=1C=C2C=CC(NC2=CC1)=O | [c:7]1([Br:8])[cH:9][cH:10][c:11]([NH2:12])[cH:19][cH:21]1.[Cl:1][C:14](=[O:13])[CH:15]=[CH:16][c:17]1[cH:18][cH:3][cH:2][cH:22][cH:23]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]([Br:8])[cH:9][cH:10][c:11]2[n:12]1.[O:13]=[c:14]1[cH:15][cH:16][c:17]2[cH:18][c:19]([Br:20])[cH:21][cH:22][c:23]2[nH:24]1 | Nc1ccc(Br)cc1.O=C(Cl)C=Cc1ccccc1 | Clc1ccc2cc(Br)ccc2n1.O=c1ccc2cc(Br)ccc2[nH]1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 0cbcc759f6c07543aecf25f793381137acb525633c2c9bcb9d5a67a29429e70b | 39ffedfff726ec745f1b3654fe377a449f1cf31d2b696ecf18bd11ad86c47cac | O=c1ccc2ccccc2[nH]1.c1ccc2ncccc2c1 | [Br;D1;H0:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c;H0;D3;+0:5](-[NH2;D1;+0:6]):[cH;D2;+0:7]:[cH;D2;+0:8]:1.[Cl;H0;D1;+0:9]-[C;H0;D3;+0:10](=[O;D1;H0:11])-[CH;D2;+0:12]=[CH;D2;+0:13]-[c:14]1:[cH;D2;+0:15]:[cH;D2;+0:16]:[cH;D2;+0:17]:[cH;D2;+0:18]:[cH;D2;+0:19]:1>>[Br;D1;H0:20]-[c;H0;D3;+0:7]1:[cH;D2;+0:15]:[c:14]2:[cH;D2;+0:13... | null | [] | null | null | null | null | The title compound is prepared from 4-bromoaniline and cinnamoyl chloride according to the procedure described in J. Chem. Soc., Perkin Trans. I, 1972, 1648. The crude 6-bromo-1H-quinolin-2-one intermediate obtained is triturated in Et2O/hexanes and filtered to give a beige solid which is used directly in the chlorinat... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic halide.Primary amine | Aromatic halide.Aromatic halide.Aromatic halide | c1ccccc1.c1ccccc1 | c1ccc2ncccc2c1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccc2ncccc2c1 | Other | null | null | null | Nc1ccc(Br)cc1.O=C(Cl)C=Cc1ccccc1>>Clc1ccc2cc(Br)ccc2n1.O=c1ccc2cc(Br)ccc2[nH]1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6f47bc261884491694bca9fab87d052d | CCOC(=O)c1ccc(O)cc1.ClCCN1CCCCC1>>CCOC(=O)c1ccc(OCCN2CCCCC2)cc1 | Cl.ClCCN1CCCCC1.OC1=CC=C(C(=O)OCC)C=C1.Cl.ClCCN1CCCCC1.C([O-])([O-])=O.[K+].[K+].C(C)C(=O)C.Cl.ClCCN1CCCCC1>>N1(CCCCC1)CCOC1=CC=C(C(=O)OCC)C=C1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([OH:10])[cH:19][cH:20]1.Cl[CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][CH2:12][N:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)[cH:19][cH:20]1 | CCOC(=O)c1ccc(O)cc1.ClCCN1CCCCC1 | CCOC(=O)c1ccc(OCCN2CCCCC2)cc1 | null | null | O.C(C)(=O)OCC.C(C)#N.C(C)N(CC)CC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(OCCN2CCCCC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | 80 | CELSIUS | 1 | HOUR | A mixture of ethyl 4-hydroxybenzoate (8.31 g), 1-(2-chloroethyl)piperidine monohydrochloride (10.13 g), potassium carbonate (16.59 g), and methyl ethyl ketone (60 mL) was heated to 80° C. After one hour, the mixture was cooled to about 55° C. and treated with additional 1-(2-chloroethyl)piperidine mono-hydrochloride (0... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.C1CC[NH]CC1 | HCl | O.C(C)(=O)OCC.C(C)#N.C(C)N(CC)CC | 80 | 1 | CCOC(=O)c1ccc(O)cc1.ClCCN1CCCCC1>O.C(C)(=O)OCC.C(C)#N.C(C)N(CC)CC>CCOC(=O)c1ccc(OCCN2CCCCC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8147e79bd48043f3aa5c475b74c99072 | ClB(Cl)Cl>>Cl | B(Cl)(Cl)Cl.COC=1C=CC2=C(SC(=C2C(C2=CC=C(C=C2)OCCN2CCCCC2)=O)C2=CC=C(C=C2)OC)C1>>Cl.COC=1C=CC2=C(SC(=C2C(C2=CC=C(C=C2)OCCN2CCCCC2)=O)C2=CC=C(C=C2)OC)C1 | ClB(Cl)[Cl:37]>>[ClH:37] | ClB(Cl)Cl | Cl | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 42af6cdfb86a130c92365e01a31b50705eea7bdf12f67dc370bf24402f7ceedc | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | null | Cl-B(-Cl)-[Cl;H0;D1;+0:1]>>[ClH;D0;+0:1] | null | [] | null | null | 85 | MINUTE | A mixture of the compound prepared as described in Preparation 1 (8.46 grams) and the acid chloride prepared as described in Preparation 4 (10.0 grams) in methylene chloride (350 mL) was cooled to about 20°-25° C. The cool mixture was treated with boron trichloride (2.6 mL), and the resulting mixture mechanically stirr... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | B | C(Cl)Cl | null | 1.416667 | ClB(Cl)Cl>C(Cl)Cl>Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0969f815c0174faf9aaa41c9d3fe2629 | CCO.COc1ccc(-c2sc3cc(OC)ccc3c2C(=O)c2ccc(OCCN3CCCCC3)cc2)cc1.ClB(Cl)Cl>>ClCCCl.O=C(c1ccc(OCCN2CCCCC2)cc1)c1c(-c2ccc(O)cc2)sc2cc(O)ccc12 | C(C)O.CO.Cl.COC=1C=CC2=C(SC(=C2C(C2=CC=C(C=C2)OCCN2CCCCC2)=O)C2=CC=C(C=C2)OC)C1.B(Cl)(Cl)Cl>>ClCCCl.Cl.OC=1C=CC2=C(SC(=C2C(C2=CC=C(C=C2)OCCN2CCCCC2)=O)C2=CC=C(C=C2)O)C1 | O[CH2:3][CH3:4].C[O:29][c:28]1[cH:27][cH:26][c:25](-[c:24]2[c:23]([C:7](=[O:6])[c:8]3[cH:9][cH:10][c:11]([O:12][CH2:13][CH2:14][N:15]4[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]4)[cH:21][cH:22]3)[c:39]3[c:33]([s:32]2)[cH:34][c:35]([O:36]C)[cH:37][cH:38]3)[cH:31][cH:30]1.ClB([Cl:2])[Cl:5]>>[Cl:2][CH2:3][CH2:4][Cl:5].[O:6]=... | CCO.COc1ccc(-c2sc3cc(OC)ccc3c2C(=O)c2ccc(OCCN3CCCCC3)cc2)cc1.ClB(Cl)Cl | ClCCCl.O=C(c1ccc(OCCN2CCCCC2)cc1)c1c(-c2ccc(O)cc2)sc2cc(O)ccc12 | null | null | ClCCCl | Functional Group Addition | OtherReaction | e291139d13c0b8e8e7de6d945637022181541a3fcaeb505deeb3482cdf2d3c97 | 51cde90debbb9e2e5883e732ee764a21d0f87b929ee7730b1cba1ccfb1a57fee | O=C(c1ccc(OCCN2CCCCC2)cc1)c1c(-c2ccccc2)sc2ccccc12 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].C-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]:[c:9]:[#16;a:10].Cl-B(-[Cl;H0;D1;+0:11])-[Cl;H0;D1;+0:12].O-[CH2;D2;+0:13]-[CH3;D1;+0:14]>>[#16;a:10]:[c:9]:[c:8]:[c:6](-[OH;D1;+0:5]):[c:7].[OH;D1;+0:1]-[c:2](:[c:3]):[c:4].[Cl;H0;D1;+0:11]-[CH2;D2;+0:13]-[CH2;D2;+0:14]-[Cl;H0;D1;+0:12] | null | [] | 35 | CELSIUS | 18 | HOUR | A solution of 6-methoxy-2-(4-methoxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]benzo[b]thiophene hydrochloride (2.0 g) in 1,2-dichloroethane (20 mL) was treated with boron trichloride (2.0 mL). The resulting mixture was stirred at 35° C. for about 18 hours. A mixture of ethanol and methanol (10 mL, 95:5, 3A) was treated ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Primary alcohol | Primary halide.Primary halide.Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1.c1ccc2sccc2c1 | HCl.B | ClCCCl | 35 | 18 | CCO.COc1ccc(-c2sc3cc(OC)ccc3c2C(=O)c2ccc(OCCN3CCCCC3)cc2)cc1.ClB(Cl)Cl>ClCCCl>ClCCCl.O=C(c1ccc(OCCN2CCCCC2)cc1)c1c(-c2ccc(O)cc2)sc2cc(O)ccc12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0c09083e2b874221ab0a6e445f536398 | Clc1cn[nH]c1.OC1(c2ccccc2)CC[N+]2(CCCC2)CC1>>OC1(c2ccccc2)CCN(CCCCn2cc(Cl)cn2)CC1 | OC1(CC[N+]2(CCCC2)CC1)C1=CC=CC=C1.ClC=1C=NNC1.C([O-])([O-])=O.[K+].[K+]>>ClC=1C=NN(C1)CCCCN1CCC(CC1)(C1=CC=CC=C1)O | [nH:16]1[cH:17][c:18]([Cl:19])[cH:20][n:21]1.[OH:1][C:2]1([c:3]2[cH:4][cH:5][cH:6][cH:7][cH:8]2)[CH2:9][CH2:10][N+:11]2([CH2:12][CH2:13][CH2:14][CH2:15]2)[CH2:22][CH2:23]1>>[OH:1][C:2]1([c:3]2[cH:4][cH:5][cH:6][cH:7][cH:8]2)[CH2:9][CH2:10][N:11]([CH2:12][CH2:13][CH2:14][CH2:15][n:16]2[cH:17][c:18]([Cl:19])[cH:20][n:21]... | Clc1cn[nH]c1.OC1(c2ccccc2)CC[N+]2(CCCC2)CC1 | OC1(c2ccccc2)CCN(CCCCn2cc(Cl)cn2)CC1 | null | null | CN(C=O)C.C(C)OCC | Functional Group Addition | OtherReaction | 7f675e4b5b49a74d97d1a13f2621ade6753f19308221f920741cfac5e065a78c | a5ecc0f9f40a26873e3f25b9146fa7daf7ef454ae1fed653ab37babf6624d21a | c1ccc(C2CCN(CCCCn3cccn3)CC2)cc1 | [#7;a:1]1:[c:2]:[c:3]:[c:4]:[nH;D2;+0:5]:1.[C:6]-[C:7]-[N+;H0;D4:8]1(-[C:9]-[C:10])-[C:11]-[C:12]-[C:13]-[CH2;D2;+0:14]-1>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[C:11]-[C:12]-[C:13]-[CH2;D2;+0:14]-[n;H0;D3;+0:5]1:[#7;a:1]:[c:2]:[c:3]:[c:4]:1)-[C:9]-[C:10] | 77.3 | [{"value": 77.3, "product": "ClC=1C=NN(C1)CCCCN1CCC(CC1)(C1=CC=CC=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 15.0 g (48 mmol) of 8-hydroxy-8-phenyl-5-azoniaspiro[4,5]decane, 5.4 g (53 mmol) of 4-chloropyrazole and 13.2 g of potassium carbonate in 200 ml of dimethylformamide is heated at reflux for 20 hours. Evaporation to dryness is then carried out at reduced pressure, the residue is redissolved in chloroform an... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1cn[nH]c1.C1CC[N+]2(CC1)CCCC2 | C1CC[NH]CC1.c1cn[nH]c1 | c1ccccc1.C1CC[NH]CC1.c1cn[nH]c1 | null | CN(C=O)C.C(C)OCC | null | null | Clc1cn[nH]c1.OC1(c2ccccc2)CC[N+]2(CCCC2)CC1>CN(C=O)C.C(C)OCC>OC1(c2ccccc2)CCN(CCCCn2cc(Cl)cn2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a1beaa3b1b63410ca82b9562ddec3ef2 | C1=C(c2ccccc2)CCNC1.ClCCCCn1ccc2ccccc21>>C1=C(c2ccccc2)CCN(CCCCn2ccc3ccccc32)C1 | C1(=CC=CC=C1)C=1CCNCC1.ClCCCCN1C=CC2=CC=CC=C12.C([O-])([O-])=O.[K+].[K+]>>C1(=CC=CC=C1)C=1CCN(CC1)CCCCN1C=CC2=CC=CC=C12 | [CH:1]1=[C:2]([c:3]2[cH:4][cH:5][cH:6][cH:7][cH:8]2)[CH2:9][CH2:10][NH:11][CH2:25]1.Cl[CH2:12][CH2:13][CH2:14][CH2:15][n:16]1[cH:17][cH:18][c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]12>>[CH:1]1=[C:2]([c:3]2[cH:4][cH:5][cH:6][cH:7][cH:8]2)[CH2:9][CH2:10][N:11]([CH2:12][CH2:13][CH2:14][CH2:15][n:16]2[cH:17][cH:18][c:19]3[c... | C1=C(c2ccccc2)CCNC1.ClCCCCn1ccc2ccccc21 | C1=C(c2ccccc2)CCN(CCCCn2ccc3ccccc32)C1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 8654cc80599d789a53d1ba976beafc80caf5e8f4841be95ae420fabbb64ff19c | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | C1=C(c2ccccc2)CCN(CCCCn2ccc3ccccc32)C1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[c:4]-[C:5]1=[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:9]-[C:10]-[C:5](-[c:4])=[C:6]-[C:7]-1 | null | [] | 90 | CELSIUS | null | null | A mixture of 4.8 g (30 mmol) of 4-phenyl-1,2,3,6-tetrahydropyridine, 6.22 g of 1-(4-chlorobutyl)indole and 8.3 g of potassium carbonate in 100 ml of dimethylformamide is heated at 90° C. for 3 hours. Evaporation to dryness is then carried out at reduced pressure, the residue is redissolved in chloroform and washing is ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1=CCNCC1 | C1=CC[NH]CC1 | C1=CC[NH]CC1.c1ccccc1.c1ccc2[nH]ccc2c1 | HCl | CN(C=O)C | 90 | null | C1=C(c2ccccc2)CCNC1.ClCCCCn1ccc2ccccc21>CN(C=O)C>C1=C(c2ccccc2)CCN(CCCCn2ccc3ccccc32)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3a1aef668cbd4a6686d1e5acf17de1e2 | ClCCCN1CC=C(c2ccccc2)CC1.Clc1cn[nH]c1>>Clc1cnn(CCCN2CC=C(c3ccccc3)CC2)c1 | ClC=1C=NNC1.[H-].[Na+].ClCCCN1CCC(=CC1)C1=CC=CC=C1>>ClC=1C=NN(C1)CCCN1CCC(=CC1)C1=CC=CC=C1 | Cl[CH2:6][CH2:7][CH2:8][N:9]1[CH2:10][CH:11]=[C:12]([c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19][CH2:20]1.[Cl:1][c:2]1[cH:3][n:4][nH:5][cH:21]1>>[Cl:1][c:2]1[cH:3][n:4][n:5]([CH2:6][CH2:7][CH2:8][N:9]2[CH2:10][CH:11]=[C:12]([c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[CH2:19][CH2:20]2)[cH:21]1 | ClCCCN1CC=C(c2ccccc2)CC1.Clc1cn[nH]c1 | Clc1cnn(CCCN2CC=C(c3ccccc3)CC2)c1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 31849359320dc3760d1a762ce95f120a544970fcb32b476aacf584ef81779a29 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | C1=C(c2ccccc2)CCN(CCCn2cccn2)C1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[#7;a:4]1:[c:5]:[c:6]:[c:7]:[nH;D2;+0:8]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:8]1:[#7;a:4]:[c:5]:[c:6]:[c:7]:1 | 86 | [{"value": 86.0, "product": "ClC=1C=NN(C1)CCCN1CCC(=CC1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A solution of 2.05 g (20 mmol of 4-chloropyrazole in dimethylformamide is added dropwise to a suspension of 1.0 g of NaH in dimethylformamide. The white suspension is heated for 30 minutes at 100° C. Cooling is carried out and 4.7 g (20 mmol) of 1-(3-chloropropyl)-4-phenyl-1,2,3,6-tetrahydropyridine, dissolved in dimet... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1.C1=CC[NH]CC1.c1ccccc1 | HCl | CN(C=O)C | 100 | null | ClCCCN1CC=C(c2ccccc2)CC1.Clc1cn[nH]c1>CN(C=O)C>Clc1cnn(CCCN2CC=C(c3ccccc3)CC2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6084487d99d546f3b8c77a5c36cc747e | OC1(c2ccccc2)CCN(CCCCn2cnc3ccccc32)CC1>>C1=C(c2ccccc2)CCN(CCCCn2cnc3ccccc32)C1 | OC1(CCN(CC1)CCCCN1C=NC2=C1C=CC=C2)C2=CC=CC=C2.Cl>>C1(=CC=CC=C1)C=1CCN(CC1)CCCCN1C=NC2=C1C=CC=C2 | O[C:2]1([c:3]2[cH:4][cH:5][cH:6][cH:7][cH:8]2)[CH2:1][CH2:25][N:11]([CH2:12][CH2:13][CH2:14][CH2:15][n:16]2[cH:17][n:18][c:19]3[cH:20][cH:21][cH:22][cH:23][c:24]23)[CH2:10][CH2:9]1>>[CH:1]1=[C:2]([c:3]2[cH:4][cH:5][cH:6][cH:7][cH:8]2)[CH2:9][CH2:10][N:11]([CH2:12][CH2:13][CH2:14][CH2:15][n:16]2[cH:17][n:18][c:19]3[cH:2... | OC1(c2ccccc2)CCN(CCCCn2cnc3ccccc32)CC1 | C1=C(c2ccccc2)CCN(CCCCn2cnc3ccccc32)C1 | null | null | C(C)O | Functional Group Interconversion | OtherReaction | 21476e2591dc4a15ee4440257bad6bfadae9c4aed3c143a44bb1d4238f3edeac | 63e4ba80024292782b5f87f96975225484dff39f49e96eea21874ac0cd9091a0 | C1=C(c2ccccc2)CCN(CCCCn2cnc3ccccc32)C1 | O-[C;H0;D4;+0:1]1(-[c:2](:[c:3]):[c:4])-[C:5]-[C:6]-[#7:7](-[C:8])-[C:9]-[CH2;D2;+0:10]-1>>[C:8]-[#7:7]1-[C:6]-[C:5]-[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4])=[CH;D2;+0:10]-[C:9]-1 | 72 | [{"value": 72.0, "product": "C1(=CC=CC=C1)C=1CCN(CC1)CCCCN1C=NC2=C1C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 13.4 g (38.2 mmol) of 1-[4-(4-hydroxy-4-phenyl-1-piperidyl)butyl]-1H-benzimidazole, 150 ml of concentrated HCl and 75 ml of ethanol is heated at reflux for 6 hours. The ethanol is then evaporated and the aqueous solution is cooled, basified with dilute NaOH and extracted with chloroform. The organic phase... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | C1CC[NH]CC1 | C1=CC[NH]CC1 | C1=CC[NH]CC1.c1ccccc1.c1ccc2[nH]cnc2c1 | HO- | C(C)O | null | null | OC1(c2ccccc2)CCN(CCCCn2cnc3ccccc32)CC1>C(C)O>C1=C(c2ccccc2)CCN(CCCCn2cnc3ccccc32)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2c61f63832514f10a9e3abea4cbd484d | Cc1cc[c]([Mg][Br])cc1.Cc1nc(Cl)c(Cl)n1CCCCN1CCC(=O)CC1>>Cc1ccc(C2(O)CCN(CCCCn3c(C)nc(Cl)c3Cl)CC2)cc1 | ClC=1N=C(N(C1Cl)CCCCN1CCC(CC1)=O)C.[Mg+2].[Cl-].[Cl-].CC1=CC=C(C=C1)[Mg]Br.[Cl-].[NH4+]>>ClC=1N=C(N(C1Cl)CCCCN1CCC(CC1)(C1=CC=C(C=C1)C)O)C | [Br][Mg][c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:26][cH:25]1.[C:6]1(=[O:7])[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][CH2:13][CH2:14][n:15]2[c:16]([CH3:17])[n:18][c:19]([Cl:20])[c:21]2[Cl:22])[CH2:23][CH2:24]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]2([OH:7])[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][CH2:13][CH2:14][n:15]3[c:16]([CH3:17... | Cc1cc[c]([Mg][Br])cc1.Cc1nc(Cl)c(Cl)n1CCCCN1CCC(=O)CC1 | Cc1ccc(C2(O)CCN(CCCCn3c(C)nc(Cl)c3Cl)CC2)cc1 | null | null | C1CCOC1.O1CCCC1 | C-C Coupling | Grignard from ketone to alcohol | 39a69a1fc9e827e1539c014575b38996b95ae95069c5158a41f5642f53096240 | 5854166cd4ea706bc07d74dc79eb8f4a990bc6c5eacbf0ca947d88ee86e78fdf | c1ccc(C2CCN(CCCCn3ccnc3)CC2)cc1 | [Br]-[Mg]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[O;H0;D1;+0:6]=[C;H0;D3;+0:7]1-[C:8]-[C:9]-[#7:10]-[C:11]-[C:12]-1>>[OH;D1;+0:6]-[C;H0;D4;+0:7]1(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:8]-[C:9]-[#7:10]-[C:11]-[C:12]-1 | null | [] | null | null | 5 | MINUTE | A solution of 1.0 g (3.3 mmol) of 4,5-dichloro-2-methyl-1-[4-(4-oxo-1-piperidyl)butyl]-1H-imidazole in 10 ml of anhydrous tetrahydrofuran is added to a suspension of 1.08 g (11.4 mmol) of MgCl2 in 15 ml of anhydrous THF at -40° C. and under a nitrogen atmosphere. The mixture is stirred for 5 minutes and then, at -40° C... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Ketone | Tertiary alcohol | c1ccccc1.C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1c[nH]cn1 | Br-.Mg | C1CCOC1.O1CCCC1 | null | 0.083333 | Cc1cc[c]([Mg][Br])cc1.Cc1nc(Cl)c(Cl)n1CCCCN1CCC(=O)CC1>C1CCOC1.O1CCCC1>Cc1ccc(C2(O)CCN(CCCCn3c(C)nc(Cl)c3Cl)CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1d493516fe2d4ee2a7f47af68aa4490b | O=C(CCn1cccn1)CN1CC=C(c2ccccc2)CC1>>C1=C(c2ccccc2)CCN(CCCCn2cccn2)C1 | [H-].[H-].[H-].[H-].[Li+].[Al+3].C1(=CC=CC=C1)C=1CCN(CC1)CC(CCN1N=CC=C1)=O>>C1(=CC=CC=C1)C=1CCN(CC1)CCCCN1N=CC=C1 | O=[C:13]([CH2:12][N:11]1[CH2:10][CH2:9][C:2]([c:3]2[cH:4][cH:5][cH:6][cH:7][cH:8]2)=[CH:1][CH2:21]1)[CH2:14][CH2:15][n:16]1[cH:17][cH:18][cH:19][n:20]1>>[CH:1]1=[C:2]([c:3]2[cH:4][cH:5][cH:6][cH:7][cH:8]2)[CH2:9][CH2:10][N:11]([CH2:12][CH2:13][CH2:14][CH2:15][n:16]2[cH:17][cH:18][cH:19][n:20]2)[CH2:21]1 | O=C(CCn1cccn1)CN1CC=C(c2ccccc2)CC1 | C1=C(c2ccccc2)CCN(CCCCn2cccn2)C1 | null | null | C1CCOC1 | Reduction | OtherReaction | bdac4f77103f4da1c5b42ea95e05b0b7b31176b78204db5f4144ffca7b3d54d5 | f9ba67182f94acd5fbe41487f8f71e26bccf898b8fc8091ef46f4363de5628d4 | C1=C(c2ccccc2)CCN(CCCCn2cccn2)C1 | O=[C;H0;D3;+0:1](-[C:2]-[#7:3])-[C:4]-[C:5]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[C:4]-[C:5] | 82 | [{"value": 82.0, "product": "C1(=CC=CC=C1)C=1CCN(CC1)CCCCN1N=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2.0 g of LiAlH4 are added to a solution of 3.3 g (10 mmol) of 1-[4-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)-3-oxobutyl]-1H-pyrazole in 25 ml of THF. The resulting mixture is refluxed for 2 hours. The excess LiAlH4 is destroyed by addition of concentrated NaOH and water. The inorganic salts are filtered off and the THF i... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | null | null | C1=CC[NH]CC1.c1ccccc1.c1cn[nH]c1 | Other | C1CCOC1 | null | null | O=C(CCn1cccn1)CN1CC=C(c2ccccc2)CC1>C1CCOC1>C1=C(c2ccccc2)CCN(CCCCn2cccn2)C1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4897d8268b054a86a723074d1e00d03f | Cl>>Cl | Cl.C(C)O.ClC=1N=C(N(C1Cl)CCCCN1CCC(=CC1)C1=CC=CC=C1)C>>Cl.ClC=1N=C(N(C1Cl)CCCCN1CCC(=CC1)C1=CC=CC=C1)C | [ClH:25]>>[ClH:25] | Cl | Cl | null | null | C(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 189.2 | [{"value": 189.2, "product": "Cl.ClC=1N=C(N(C1Cl)CCCCN1CCC(=CC1)C1=CC=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2.5 ml of an 8.4N hydrochloric acid/ethanol solution are added to a solution, cooled in an ice bath, of 7.4 g (20.3 mmol) of 4,5-dichloro-2-methyl-1-[4-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)butyl]-1H-imidazole in 15 ml of absolute ethanol. After a few minutes, a precipitate appears which is filtered, washed with cold ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)O | null | null | Cl>C(C)O>Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5e0b95a71d344bdb9f611380d0f3cc56 | O=C1CCCc2ccccc21>>C1=Cc2ccccc2CC1 | C(C1=CC=CC=C1)(=N)N.C1(CCCC2=CC=CC=C12)=O.CC=1C=CC(=CC1)S(=O)(=O)O.[BH4-].[Na+]>>C1CC=CC2=CC=CC=C12 | O=[C:2]1[CH2:1][CH2:10][CH2:9][c:8]2[c:3]1[cH:4][cH:5][cH:6][cH:7]2>>[CH:1]1=[CH:2][c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[CH2:9][CH2:10]1 | O=C1CCCc2ccccc21 | C1=Cc2ccccc2CC1 | null | null | C(C)(=O)O.C1=CC=CC=C1 | Miscellaneous | OtherReaction | f554b4ee49b6c7645f21398f5b85a4d4b9e15676f9e956613ba40937cf15d837 | 9db0f73aed071f5fa7238b261fc87a241efa69e871d2f239452605149d0c954e | C1=Cc2ccccc2CC1 | O=[C;H0;D3;+0:1]1-[CH2;D2;+0:2]-[C:3]-[C:4]-[c:5]:[c:6]-1:[c:7]>>[c:7]:[c:6]1:[c:5]-[C:4]-[C:3]-[CH;D2;+0:2]=[CH;D2;+0:1]-1 | null | [] | null | null | null | null | Scheme 12 outlines the preparation of tetralins having an acetic acid residue at C2 and an amide linked benzamidine at C6. In the first step, tetralone 81 is reduced with NaBH4 and the resultant unstable alcohol is dehydrated with TsOH in benzene giving dihydronapthalene 82. Osymylation of 82 affords diol 83 which is t... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | c1ccc2c(c1)CCCC2 | C1=Cc2ccccc2CC1 | C1=Cc2ccccc2CC1 | Other | C(C)(=O)O.C1=CC=CC=C1 | null | null | O=C1CCCc2ccccc21>C(C)(=O)O.C1=CC=CC=C1>C1=Cc2ccccc2CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b9c8478b753b4132a133ace38f7e208b | CNOC.Cc1ncoc1C(=O)Cl>>CON(C)C(=O)c1ocnc1C | C(O)([O-])=O.[Na+].CC=1N=COC1C(=O)Cl.Cl.CNOC.N1=CC=CC=C1>>CON(C(=O)C1=C(N=CO1)C)C | [CH3:1][O:2][NH:3][CH3:4].Cl[C:5](=[O:6])[c:7]1[o:8][cH:9][n:10][c:11]1[CH3:12]>>[CH3:1][O:2][N:3]([CH3:4])[C:5](=[O:6])[c:7]1[o:8][cH:9][n:10][c:11]1[CH3:12] | CNOC.Cc1ncoc1C(=O)Cl | CON(C)C(=O)c1ocnc1C | null | null | C(Cl)(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | c1cocn1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#8;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[C;D1;H3:8].[C;D1;H3:9]-[#8:10]-[NH;D2;+0:11]-[C;D1;H3:12]>>[C;D1;H3:8]-[c:7]1:[#7;a:6]:[c:5]:[#8;a:4]:[c:3]:1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:11](-[C;D1;H3:12])-[#8:10]-[C;D1;H3:9] | null | [] | null | null | null | null | 4-Methyl-5-oxazolecarbonyl chloride (15 g) and N,O-dimethylhydroxylamine hydrochloride (11 g) in dry chloroform (100 ml) were cooled to 0° C. and dry pyridine (28.5 g) was added. The mixture was allowed to warm to room temperature. After 30 minutes aqueous sodium hydrogen carbonate was added and the organic layer separ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1cocn1 | HCl | C(Cl)(Cl)Cl | null | null | CNOC.Cc1ncoc1C(=O)Cl>C(Cl)(Cl)Cl>CON(C)C(=O)c1ocnc1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-69d90fe1ebe346e2ad0d74e44a53c346 | Brc1ccoc1.CON(C)C(=O)c1ocnc1C>>Cc1ncoc1C(=O)c1ccoc1 | [Cl-].[Na+].C(CCC)[Li].BrC1=COC=C1.CON(C(=O)C1=C(N=CO1)C)C>>CC=1N=COC1C(=O)C1=COC=C1 | Br[c:9]1[cH:10][cH:11][o:12][cH:13]1.CON(C)[C:7]([c:6]1[c:2]([CH3:1])[n:3][cH:4][o:5]1)=[O:8]>>[CH3:1][c:2]1[n:3][cH:4][o:5][c:6]1[C:7](=[O:8])[c:9]1[cH:10][cH:11][o:12][cH:13]1 | Brc1ccoc1.CON(C)C(=O)c1ocnc1C | Cc1ncoc1C(=O)c1ccoc1 | null | null | C(C)O.C(C)OCC | C-C Coupling | OtherReaction | b6253f5511204f961138e67901e3464478ba474fec97457ac8b7f18ef0d3225e | 7d9aa59f8ecc532475d910f9ab122332ecbb7f9444a37371b7c1bac80798d342 | O=C(c1ccoc1)c1cnco1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#8;a:4]:[c:5]:1.C-O-N(-C)-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8]1:[#8;a:9]:[c:10]:[#7;a:11]:[c:12]:1-[C;D1;H3:13]>>[C;D1;H3:13]-[c:12]1:[#7;a:11]:[c:10]:[#8;a:9]:[c:8]:1-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#8;a:4]:[c:5]:1 | null | [] | -70 | CELSIUS | 30 | MINUTE | 3-Bromofuran (2.5 g) in dry diethylether was stirred and cooled to -70° C. under an atmosphere of dry nitrogen and n-butyllithium (2.5M solution in hexane, 6.8 ml) was added dropwise. After 30 minutes, N-methoxy-N-methyl-4-methyl-5-oxazolecarboxamide (2.89 g) in dry diethylether was added dropwise. After a further 30 m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amide | Ketone | c1ccoc1 | c1ccoc1 | c1cocn1.c1ccoc1 | HBr | C(C)O.C(C)OCC | -70 | 0.5 | Brc1ccoc1.CON(C)C(=O)c1ocnc1C>C(C)O.C(C)OCC>Cc1ncoc1C(=O)c1ccoc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-eb5bfefcbfd94ea0be77c604cb53b9bd | CC(=O)C(Cl)C(C)=O.CCC(N)=O>>CCc1nc(C)c(C(C)=O)o1 | [OH-].[Na+].ClC(C(C)=O)C(C)=O.C(CC)(=O)N.C(CC)(=O)O>>C(C)(=O)C1=C(N=C(O1)CC)C | O=[C:5]([CH3:6])[CH:7](Cl)[C:8]([CH3:9])=[O:10].[CH3:1][CH2:2][C:3]([NH2:4])=[O:11]>>[CH3:1][CH2:2][c:3]1[n:4][c:5]([CH3:6])[c:7]([C:8]([CH3:9])=[O:10])[o:11]1 | CC(=O)C(Cl)C(C)=O.CCC(N)=O | CCc1nc(C)c(C(C)=O)o1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | d7ae04d5597e28d8d2674031fcc7f379795c815d9b55b6459504c8b3ba9e8c0b | 560d41b5d5b41ecc3e1c1e993b94a7d490fe96e95dfe180ea404e97cf4fa1c36 | c1cocn1 | Cl-[CH;D3;+0:1](-[C:2](-[C;D1;H3:3])=[O;D1;H0:4])-[C;H0;D3;+0:5](=O)-[C;D1;H3:6].[C;D1;H3:7]-[C:8]-[C;H0;D3;+0:9](-[NH2;D1;+0:10])=[O;H0;D1;+0:11]>>[C;D1;H3:7]-[C:8]-[c;H0;D3;+0:9]1:[n;H0;D2;+0:10]:[c;H0;D3;+0:5](-[C;D1;H3:6]):[c;H0;D3;+0:1](-[C:2](-[C;D1;H3:3])=[O;D1;H0:4]):[o;H0;D2;+0:11]:1 | null | [] | null | null | null | null | 3-Chloropentane-2,4-dione (46.5 g), propionamide (50 g) and propionic acid (151 g) were heated at 145° C. for 5 hours. The mixture was cooled to room temperature, then basified to pH 10 using 10M aqueous sodium hydroxide, and extracted with dichloromethane. The combined extracts were washed with brine, dried and the so... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone.Ketone.Primary amide | Ketone | null | c1cocn1 | c1cocn1 | HCl | null | null | null | CC(=O)C(Cl)C(C)=O.CCC(N)=O>>CCc1nc(C)c(C(C)=O)o1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1bc1f72b809c473ca26027a1470cdec4 | CON(C)C(=O)c1ocnc1C>>CCC(=O)c1ocnc1C | CON(C(=O)C1=C(N=CO1)C)C.C(C)[Mg]Br.C(O)([O-])=O.[Na+]>>CC=1N=COC1C(CC)=O | CON(C)[C:3](=[O:4])[c:5]1[o:6][cH:7][n:8][c:9]1[CH3:10]>>[CH3:1][CH2:2][C:3](=[O:4])[c:5]1[o:6][cH:7][n:8][c:9]1[CH3:10] | CON(C)C(=O)c1ocnc1C | CCC(=O)c1ocnc1C | null | null | O1CCCC1 | Functional Group Interconversion | OtherReaction | 0e1b501f4aadb0e84ffc93b33216cc37dfe617cb6c3e325779c58539a7f5c4e4 | af85307a4412ed48cedcfde84079732215472ffbe274bdc1dc12e9979d5c5e06 | c1cocn1 | C-O-N(-C)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#8;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[C;D1;H3:8]>>[C;D1;H3:8]-[c:7]1:[#7;a:6]:[c:5]:[#8;a:4]:[c:3]:1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:9]-[C;D1;H3:10] | null | [] | null | null | 30 | MINUTE | N-Methoxy-N-methyl-4-methyl-5-oxazolecarboxamide (5 g) in dry tetrahydrofuran at -40° C. was stirred under a nitrogen atmosphere and ethylmagnesium bromide (1M solution in tetrahydrofuran, 35 ml) was added dropwise. After 30 minutes the mixture was allowed to warm to room temperature and then stirred for a further 1 ho... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Ketone | null | null | c1cocn1 | HO- | O1CCCC1 | null | 0.5 | CON(C)C(=O)c1ocnc1C>O1CCCC1>CCC(=O)c1ocnc1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5a7b382c7d5a4739a7806a3eb2f4a308 | C[Si](C)(C)Cl.Cc1cscn1>>Cc1csc([Si](C)(C)C)n1 | C(CCC)[Li].CC=1N=CSC1.C[Si](C)(C)Cl>>CC=1N=C(SC1)[Si](C)(C)C | Cl[Si:6]([CH3:7])([CH3:8])[CH3:9].[CH3:1][c:2]1[cH:3][s:4][cH:5][n:10]1>>[CH3:1][c:2]1[cH:3][s:4][c:5]([Si:6]([CH3:7])([CH3:8])[CH3:9])[n:10]1 | C[Si](C)(C)Cl.Cc1cscn1 | Cc1csc([Si](C)(C)C)n1 | null | null | C(C)OCC | Functional Group Interconversion | OtherReaction | 846f89985496818bb5656201a7c930a33abe7137a81d5d33bff710dc37660505 | 62b25486659a0c3b8981491307676661488416039e4a601c8996c7216be92cf1 | c1cscn1 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C;D1;H3:4].[#16;a:5]1:[c:6]:[c:7]:[#7;a:8]:[cH;D2;+0:9]:1>>[C;D1;H3:2]-[Si;H0;D4;+0:1](-[C;D1;H3:3])(-[C;D1;H3:4])-[c;H0;D3;+0:9]1:[#16;a:5]:[c:6]:[c:7]:[#7;a:8]:1 | null | [] | null | null | 30 | MINUTE | n-Butyllithium (2.5M solution in hexane, 1.1 equivalents) was added dropwise to a solution of 4-methylthiazole (1.0 equivalent) in dry diethyl ether at -70° C. under an atmosphere of dry nitrogen. After 30 minutes, trimethylsilylchloride (1.0 equivalent) was added dropwise. The mixture was allowed to warm to room tempe... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | Silyl protective group | c1cscn1 | c1cscn1 | c1cscn1 | HCl | C(C)OCC | null | 0.5 | C[Si](C)(C)Cl.Cc1cscn1>C(C)OCC>Cc1csc([Si](C)(C)C)n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-24c2c46a829e48159acfde789ed8bd92 | CON(C)C(=O)c1oc(C)nc1C.[Li][C](C)(C)C>>Cc1nc(C)c(C(=O)C(C)(C)C)o1 | CON(C(=O)C1=C(N=C(O1)C)C)C.C(C)(C)(C)[Li]>>CC=1OC(=C(N1)C)C(=O)C(C)(C)C | CON(C)[C:7]([c:6]1[c:4]([CH3:5])[n:3][c:2]([CH3:1])[o:13]1)=[O:8].[Li][C:9]([CH3:10])([CH3:11])[CH3:12]>>[CH3:1][c:2]1[n:3][c:4]([CH3:5])[c:6]([C:7](=[O:8])[C:9]([CH3:10])([CH3:11])[CH3:12])[o:13]1 | CON(C)C(=O)c1oc(C)nc1C.[Li][C](C)(C)C | Cc1nc(C)c(C(=O)C(C)(C)C)o1 | null | null | null | C-C Coupling | OtherReaction | 023cbc9ce5f0e6327f737604e238c90756daffe1dbbd1c1832c34b492285347c | da1a5f48015ed28f0e16771d2a6b49d21657cdf8fc269eb48a3cbe2895ec45db | c1cocn1 | C-O-N(-C)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#8;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[C;D1;H3:8].[C;D1;H3:9]-[C;H0;D4;+0:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[Li]>>[C;D1;H3:9]-[C;H0;D4;+0:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#8;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[C;D1;H3:8] | null | [] | null | null | null | null | Starting with N-methoxy-N-methyl-2,4-dimethyl-5-oxazolecarboxamide and t-butyllithium and following the general method of Preparation 3, the title compound was prepared.
Conditions: See reaction.notes.procedure_details.
Workup: the general method of Preparation 3 | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Alkyl lithium | Ketone | null | null | c1cocn1 | HO-.Li | null | null | null | CON(C)C(=O)c1oc(C)nc1C.[Li][C](C)(C)C>>Cc1nc(C)c(C(=O)C(C)(C)C)o1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ca2c656728094237986dc15e1b9e16c6 | Brc1ccoc1.CCOC(=O)C(F)(F)F>>O=C(c1ccoc1)C(F)(F)F | Cl.BrC1=COC=C1.C(CCC)[Li].FC(C(=O)OCC)(F)F>>FC(C(=O)C1=COC=C1)(F)F | Br[c:3]1[cH:4][cH:5][o:6][cH:7]1.CCO[C:2](=[O:1])[C:8]([F:9])([F:10])[F:11]>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][o:6][cH:7]1)[C:8]([F:9])([F:10])[F:11] | Brc1ccoc1.CCOC(=O)C(F)(F)F | O=C(c1ccoc1)C(F)(F)F | null | null | C(C)OCC | C-C Coupling | Ester and halide to ketone | e99ab082d1e0901cc6d4f26518f3f447f1da675f1df7d5c41dc50e8ccb392711 | 7000e6fa6236297c1c515ebeaf5c7ba17704e006a4336e184f2503c0f1949baf | c1ccoc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#8;a:4]:[c:5]:1.C-C-O-[C;H0;D3;+0:6](=[O;D1;H0:7])-[C:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11]>>[F;D1;H0:9]-[C:8](-[F;D1;H0:10])(-[F;D1;H0:11])-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#8;a:4]:[c:5]:1 | null | [] | null | null | 30 | MINUTE | 3-Bromofuran (20 g) was added to a solution of n-butyllithium (2.5M in hexanes, 60 ml) in diethyl ether (200 ml) at -70° C. After 30 minutes, ethyl trifluoroacetate (28.6 g) was added slowly. After a further 1 hour the mixture was allowed to warm to room temperature and was then left to stir overnight. 1M Hydrochloric ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester | Ketone | c1ccoc1 | c1ccoc1 | c1ccoc1 | HBr | C(C)OCC | null | 0.5 | Brc1ccoc1.CCOC(=O)C(F)(F)F>C(C)OCC>O=C(c1ccoc1)C(F)(F)F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ea8d9c1fc5de4b569364ab4d8c41abcc | CC(=O)CC(=O)C(F)(F)F.NC(N)=S>>CC(=O)c1sc(N)nc1C(F)(F)F | OC=1C(=C(C=CC1)I)OS(=O)(=O)C1=CC=C(C)C=C1.FC(C(CC(C)=O)=O)(F)F.NC(=S)N>>C(C)(=O)C1=C(N=C(S1)N)C(F)(F)F | O=[C:9]([CH2:4][C:2]([CH3:1])=[O:3])[C:10]([F:11])([F:12])[F:13].[S:5]=[C:6]([NH2:7])[NH2:8]>>[CH3:1][C:2](=[O:3])[c:4]1[s:5][c:6]([NH2:7])[n:8][c:9]1[C:10]([F:11])([F:12])[F:13] | CC(=O)CC(=O)C(F)(F)F.NC(N)=S | CC(=O)c1sc(N)nc1C(F)(F)F | null | null | C(C)#N | Aromatic Heterocycle Formation | OtherReaction | eaa861bc361e3c3da89965dbe533556c2590fa3862defaa8bf6fa6c7c8db93dd | 9697a30197f0349c13522202327fe4f1dc1b0146b3367b74ef1050a9ef769e2b | c1cscn1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[C:3](-[C;D1;H3:4])=[O;D1;H0:5])-[C:6](-[F;D1;H0:7])(-[F;D1;H0:8])-[F;D1;H0:9].[N;D1;H2:10]-[C;H0;D3;+0:11](-[NH2;D1;+0:12])=[S;H0;D1;+0:13]>>[C;D1;H3:4]-[C:3](=[O;D1;H0:5])-[c;H0;D3;+0:2]1:[s;H0;D2;+0:13]:[c;H0;D3;+0:11](-[N;D1;H2:10]):[n;H0;D2;+0:12]:[c;H0;D3;+0:1]:1-[C:6](-[F;D1;H0:7]... | null | [] | null | null | 8 | HOUR | Hydroxy(tosyloxy)iodobenzene (78.5 g) was added to a solution of 1,1,1-trifluoropentane-2,4-dione in acetonitrile (500 ml). The mixture was heated under reflux for 45 minutes, then cooled, and thiourea (15.2 g) was added. The mixture was heated under reflux for 4 hours and then left to stand overnight. Evaporation and ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Thiourea | Ketone | null | c1cscn1 | c1cscn1 | HO- | C(C)#N | null | 8 | CC(=O)CC(=O)C(F)(F)F.NC(N)=S>C(C)#N>CC(=O)c1sc(N)nc1C(F)(F)F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ac7f5eb35ef547d1a557dea38319f19e | CI.Cc1n[nH]c(C)c1Br>>Cc1nn(C)c(C)c1Br | IC.BrC=1C(=NNC1C)C.[H-].[Na+].C(O)([O-])=O.[Na+].[H][H]>>BrC=1C(=NN(C1C)C)C | I[CH3:5].[CH3:1][c:2]1[n:3][nH:4][c:6]([CH3:7])[c:8]1[Br:9]>>[CH3:1][c:2]1[n:3][n:4]([CH3:5])[c:6]([CH3:7])[c:8]1[Br:9] | CI.Cc1n[nH]c(C)c1Br | Cc1nn(C)c(C)c1Br | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 1feb5c3ff035c64f7021c6a0375839863d523e5d8e7a88a1745adbd51ab4e08b | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | c1cn[nH]c1 | I-[CH3;D1;+0:1].[C;D1;H3:2]-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[nH;D2;+0:7]:1>>[C;D1;H3:2]-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[n;H0;D3;+0:7]:1-[CH3;D1;+0:1] | null | [] | null | null | null | null | 4-Bromo-3,5-dimethylpyrazole (10 g) in dry dimethylformamide (50 ml) was added to a stirred suspension of sodium hydride (1.8 g) in dry dimethylformamide at 0° C. When the evolution of hydrogen was complete, iodomethane (8.9 g) was added dropwise. The mixture was allowed to warm to room temperature and after 30 minutes... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1 | HI | CN(C=O)C | null | null | CI.Cc1n[nH]c(C)c1Br>CN(C=O)C>Cc1nn(C)c(C)c1Br |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4117f1caea15466f91091f87c8c7eae4 | Cc1coc([Si](C)(C)C)n1.O=C(n1ccnc1)C(F)(F)F>>Cc1coc(C(=O)C(F)(F)F)n1 | FC(C(=O)N1C=NC=C1)(F)F.CC=1N=C(OC1)[Si](C)(C)C.O>>CC=1N=C(OC1)C(C(F)(F)F)=O | C[Si](C)(C)[c:5]1[o:4][cH:3][c:2]([CH3:1])[n:12]1.c1cn([C:6](=[O:7])[C:8]([F:9])([F:10])[F:11])cn1>>[CH3:1][c:2]1[cH:3][o:4][c:5]([C:6](=[O:7])[C:8]([F:9])([F:10])[F:11])[n:12]1 | Cc1coc([Si](C)(C)C)n1.O=C(n1ccnc1)C(F)(F)F | Cc1coc(C(=O)C(F)(F)F)n1 | null | null | C(C)OCC | C-C Coupling | OtherReaction | 4df5d6b3daf1d80542692220c964a729cf11d1409a0a78479d367cab64f9ff97 | e1ab351a0eb86efa7b9dd45bd6c2b1455685889dbf3f96ecb913465d314258ed | c1cocn1 | C-[Si](-C)(-C)-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#8;a:5]:1.[F;D1;H0:6]-[C:7](-[F;D1;H0:8])(-[F;D1;H0:9])-[C;H0;D3;+0:10](=[O;D1;H0:11])-n1:c:c:n:c:1>>[F;D1;H0:6]-[C:7](-[F;D1;H0:8])(-[F;D1;H0:9])-[C;H0;D3;+0:10](=[O;D1;H0:11])-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#8;a:5]:1 | null | [] | null | null | 8 | HOUR | 1-Trifluoroacetylimidazole (10 g) was added dropwise to 4-methyl-2-trimethylsilyloxazole (J. Chem. Soc., Chem. Commun., 1984, 258) (9.95 g) in diethyl ether (100 ml) at 0° C. under an atmosphere of dry nitrogen. The mixture was stirred overnight at room temperature. Water was added and the organic layer was separated, ... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | Ketone | c1cocn1.c1c[nH]cn1 | c1cocn1 | c1cocn1 | Other | C(C)OCC | null | 8 | Cc1coc([Si](C)(C)C)n1.O=C(n1ccnc1)C(F)(F)F>C(C)OCC>Cc1coc(C(=O)C(F)(F)F)n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7f93372015354dc38e885820152952ed | Cc1ncsc1C=O>>COCc1scnc1C | CC=1N=CSC1C=O.CC([O-])C.[Al+3].CC([O-])C.CC([O-])C.[H-].[Na+]>>COCC1=C(N=CS1)C | [O:2]=[CH:3][c:4]1[s:5][cH:6][n:7][c:8]1[CH3:9]>>[CH3:1][O:2][CH2:3][c:4]1[s:5][cH:6][n:7][c:8]1[CH3:9] | Cc1ncsc1C=O | COCc1scnc1C | null | null | CC(C)O.C(OC)COC.IC | Miscellaneous | OtherReaction | be6cac7451b8f19bfaedda10ad61a954be22d2de8098149054d551fc07cba67f | 277af6fcd8fab5f78787555255bbb2148673a2ee227942cc2003726a8aadde9b | c1cscn1 | [C;D1;H3:1]-[c:2]1:[#7;a:3]:[c:4]:[#16;a:5]:[c:6]:1-[CH;D2;+0:7]=[O;H0;D1;+0:8]>>[C;D1;H3:9]-[O;H0;D2;+0:8]-[CH2;D2;+0:7]-[c:6]1:[#16;a:5]:[c:4]:[#7;a:3]:[c:2]:1-[C;D1;H3:1] | null | [] | null | null | null | null | 4-Methyl-5-thiazolecarbaldehyde (J. Amer. Chem. Soc., 1982, 104, 4934-4943) was reduced using aluminium isopropoxide in 2-propanol. The resulting alcohol was treated with sodium hydride in dimethoxyethane and iodomethane was added. Distillation gave the title compound.
Conditions: See reaction.notes.procedure_details.
... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Ether | null | null | c1cscn1 | Other | CC(C)O.C(OC)COC.IC | null | null | Cc1ncsc1C=O>CC(C)O.C(OC)COC.IC>COCc1scnc1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c3b3ce4ed08846c8b1f2907496e08f51 | Cc1nc(-c2ccoc2)oc1C(=O)c1oc(-c2ccoc2)nc1C>>Cc1ncoc1C(C)(O)c1ccoc1 | C(C)O.O1C=C(C=C1)C=1OC(=C(N1)C)C(=O)C1=C(N=C(O1)C1=COC=C1)C.C[Li].[Cl-].[Na+]>>O1C=C(C=C1)C(C)(O)C1=C(N=CO1)C | Cc1nc(-c2ccoc2)oc1[C:7]([c:6]1[c:2]([CH3:1])[n:3][c:4](-[c:10]2[cH:11][cH:12][o:13][cH:14]2)[o:5]1)=[O:9]>>[CH3:1][c:2]1[n:3][cH:4][o:5][c:6]1[C:7]([CH3:8])([OH:9])[c:10]1[cH:11][cH:12][o:13][cH:14]1 | Cc1nc(-c2ccoc2)oc1C(=O)c1oc(-c2ccoc2)nc1C | Cc1ncoc1C(C)(O)c1ccoc1 | null | null | C(C)OCC | Miscellaneous | OtherReaction | b9782805797e3294e7f856b574bcb728d358fe7893dcb00a3def3b4ff1463020 | 8811b4d793f7cfa9f0f1f47a008648edabb54f371f76dfa680dd5b2e1564c6c5 | c1cc(Cc2cnco2)co1 | C-c1:n:c(-c2:c:c:o:c:2):o:c:1-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3]1:[#8;a:4]:[c;H0;D3;+0:5](-[c;H0;D3;+0:6]2:[c:7]:[c:8]:[#8;a:9]:[c:10]:2):[#7;a:11]:[c:12]:1-[C;D1;H3:13]>>[C;D1;H3:13]-[c:12]1:[#7;a:11]:[cH;D2;+0:5]:[#8;a:4]:[c:3]:1-[C;H0;D4;+0:1](-[C;D1;H3:14])(-[OH;D1;+0:2])-[c;H0;D3;+0:6]1:[c:7]:[c:8]:[#8;a:9]:[c:... | null | [] | null | null | 45 | MINUTE | 3-Furyl-4-methyl-5-oxazolyl ketone (1 g) in dry diethylether (15 ml) at -70° C. under a nitrogen atmosphere was treated dropwise with methyllithium (1.5M solution in diethylether, 4.1 ml). After 45 minutes the reaction mixture was allowed to warm to room temperature and ethanol (2 ml) was added. The mixture was poured ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol | c1cocn1.c1ccoc1.c1cocn1.c1ccoc1 | c1cocn1.c1ccoc1 | c1cocn1.c1ccoc1 | HO- | C(C)OCC | null | 0.75 | Cc1nc(-c2ccoc2)oc1C(=O)c1oc(-c2ccoc2)nc1C>C(C)OCC>Cc1ncoc1C(C)(O)c1ccoc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4d4da764b7ca493a80454e012df84e7d | Brc1ccsc1.CC(=O)c1ocnc1C>>Cc1ncoc1C(C)(O)c1ccsc1 | O.BrC1=CSC=C1.C(CCC)[Li].C(C)(=O)C1=C(N=CO1)C>>CC=1N=COC1C(C)(O)C1=CSC=C1 | Br[c:10]1[cH:11][cH:12][s:13][cH:14]1.[CH3:1][c:2]1[n:3][cH:4][o:5][c:6]1[C:7]([CH3:8])=[O:9]>>[CH3:1][c:2]1[n:3][cH:4][o:5][c:6]1[C:7]([CH3:8])([OH:9])[c:10]1[cH:11][cH:12][s:13][cH:14]1 | Brc1ccsc1.CC(=O)c1ocnc1C | Cc1ncoc1C(C)(O)c1ccsc1 | null | null | C(C)OCC | C-C Coupling | Grignard_alcohol | ced8db25e742cc856055ca33877a37cbea1e62e1ac0cab97d987f0994afc50bc | b8801be51258f6ee39fb6aad45dd9677b1b9eed3d6e0018ffb065bca8e787abf | c1ncc(Cc2ccsc2)o1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#16;a:4]:[c:5]:1.[C;D1;H3:6]-[c:7]1:[#7;a:8]:[c:9]:[#8;a:10]:[c:11]:1-[C;H0;D3;+0:12](-[C;D1;H3:13])=[O;H0;D1;+0:14]>>[C;D1;H3:6]-[c:7]1:[#7;a:8]:[c:9]:[#8;a:10]:[c:11]:1-[C;H0;D4;+0:12](-[C;D1;H3:13])(-[OH;D1;+0:14])-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#16;a:4]:[c:5]:1 | null | [] | null | null | 2.5 | HOUR | 3-Bromothiophene (4.23 g) in diethylether (10 ml) was added dropwise to n-butyllithium (2.5M solution in hexane, 10.4 ml) in dry diethylether (20 ml) at -70° C. under a nitrogen atmosphere. After 3 hours 5-acetyl-4-methyloxazole (2.5 g) in diethylether (10 ml) was added dropwise. After a further 2.5 hours at -70° C., t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | Tertiary alcohol | c1ccsc1 | c1ccsc1 | c1cocn1.c1ccsc1 | Br- | C(C)OCC | null | 2.5 | Brc1ccsc1.CC(=O)c1ocnc1C>C(C)OCC>Cc1ncoc1C(C)(O)c1ccsc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0cd8b984bb7449ec9670db072ec4ad56 | CC(=O)c1ocnc1C.c1ccsc1>>Cc1ncoc1C(C)(O)c1cccs1 | C(O)([O-])=O.[Na+].C(CCC)[Li].S1C=CC=C1.C(C)(=O)C1=C(N=CO1)C>>CC=1N=COC1C(C)(O)C=1SC=CC1 | [CH3:1][c:2]1[n:3][cH:4][o:5][c:6]1[C:7]([CH3:8])=[O:9].[cH:10]1[cH:11][cH:12][cH:13][s:14]1>>[CH3:1][c:2]1[n:3][cH:4][o:5][c:6]1[C:7]([CH3:8])([OH:9])[c:10]1[cH:11][cH:12][cH:13][s:14]1 | CC(=O)c1ocnc1C.c1ccsc1 | Cc1ncoc1C(C)(O)c1cccs1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 7c7bd5a8216634c04beb429a761e799f12b2429431c704ffe50a4a9c2247490a | 454f67ba8644982dc9f605915a0f36178771eadaffb50d3f1e0f17f2b6fdeb10 | c1csc(Cc2cnco2)c1 | [#16;a:1]1:[c:2]:[c:3]:[c:4]:[cH;D2;+0:5]:1.[C;D1;H3:6]-[c:7]1:[#7;a:8]:[c:9]:[#8;a:10]:[c:11]:1-[C;H0;D3;+0:12](-[C;D1;H3:13])=[O;H0;D1;+0:14]>>[C;D1;H3:6]-[c:7]1:[#7;a:8]:[c:9]:[#8;a:10]:[c:11]:1-[C;H0;D4;+0:12](-[C;D1;H3:13])(-[OH;D1;+0:14])-[c;H0;D3;+0:5]1:[#16;a:1]:[c:2]:[c:3]:[c:4]:1 | null | [] | -40 | CELSIUS | 1 | HOUR | Thiophene (3.36 g) in dry tetrahydrofuran (20 ml) was stirred and cooled to -40° C. under a dry nitrogen atmosphere and n-butyllithium (2.5M solution in hexane, 16 ml) was added dropwise. The mixture was allowed to warm to -20° C. and then after 1 hour was cooled to -70° C. 5-Acetyl-4-methyloxazole (5 g) in dry tetrahy... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol | c1ccsc1 | c1ccsc1 | c1cocn1.c1ccsc1 | null | O1CCCC1 | -40 | 1 | CC(=O)c1ocnc1C.c1ccsc1>O1CCCC1>Cc1ncoc1C(C)(O)c1cccs1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ebc0a62248e849b8b300ac6d76abcd18 | Brc1ccoc1.CC(=O)c1scnc1C>>Cc1ncsc1C(C)(O)c1ccoc1 | O.BrC1=COC=C1.C(CCC)[Li].C(C)(=O)C1=C(N=CS1)C>>O1C=C(C=C1)C(C)(O)C1=C(N=CS1)C | Br[c:10]1[cH:11][cH:12][o:13][cH:14]1.[CH3:1][c:2]1[n:3][cH:4][s:5][c:6]1[C:7]([CH3:8])=[O:9]>>[CH3:1][c:2]1[n:3][cH:4][s:5][c:6]1[C:7]([CH3:8])([OH:9])[c:10]1[cH:11][cH:12][o:13][cH:14]1 | Brc1ccoc1.CC(=O)c1scnc1C | Cc1ncsc1C(C)(O)c1ccoc1 | null | null | C(C)OCC | C-C Coupling | Grignard_alcohol | 387b0cbaf6cbd397bd265f915bdee829fa87b6f14aea3f8eab7ebee183cf19f8 | b8801be51258f6ee39fb6aad45dd9677b1b9eed3d6e0018ffb065bca8e787abf | c1cc(Cc2cncs2)co1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#8;a:4]:[c:5]:1.[C;D1;H3:6]-[c:7]1:[#7;a:8]:[c:9]:[#16;a:10]:[c:11]:1-[C;H0;D3;+0:12](-[C;D1;H3:13])=[O;H0;D1;+0:14]>>[C;D1;H3:6]-[c:7]1:[#7;a:8]:[c:9]:[#16;a:10]:[c:11]:1-[C;H0;D4;+0:12](-[C;D1;H3:13])(-[OH;D1;+0:14])-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#8;a:4]:[c:5]:1 | null | [] | null | null | 1 | HOUR | 3-Bromofuran (6.8 g) in diethylether (15 ml) was added dropwise to n-butyllithium (2.5M solution in hexane, 18.4 ml) in diethylether (20 ml) at -70° C. under a nitrogen atmosphere. After 1 hour, 5-acetyl-4-methylthiazole (5 g) in diethylether (15 ml) was added dropwise. After a further 3 hours at -70° C., the mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | Tertiary alcohol | c1ccoc1 | c1ccoc1 | c1cscn1.c1ccoc1 | Br- | C(C)OCC | null | 1 | Brc1ccoc1.CC(=O)c1scnc1C>C(C)OCC>Cc1ncsc1C(C)(O)c1ccoc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a28e5022014c4c90b9d6d574f252284a | Brc1ccsc1.CC(=O)c1oc(C)nc1C>>Cc1nc(C)c(C(C)(O)c2ccsc2)o1 | BrC1=CSC=C1.C(C)(=O)C1=C(N=C(O1)C)C>>CC=1OC(=C(N1)C)C(C)(O)C1=CSC=C1 | Br[c:10]1[cH:11][cH:12][s:13][cH:14]1.[CH3:1][c:2]1[n:3][c:4]([CH3:5])[c:6]([C:7]([CH3:8])=[O:9])[o:15]1>>[CH3:1][c:2]1[n:3][c:4]([CH3:5])[c:6]([C:7]([CH3:8])([OH:9])[c:10]2[cH:11][cH:12][s:13][cH:14]2)[o:15]1 | Brc1ccsc1.CC(=O)c1oc(C)nc1C | Cc1nc(C)c(C(C)(O)c2ccsc2)o1 | null | null | null | C-C Coupling | Grignard_alcohol | ced8db25e742cc856055ca33877a37cbea1e62e1ac0cab97d987f0994afc50bc | b8801be51258f6ee39fb6aad45dd9677b1b9eed3d6e0018ffb065bca8e787abf | c1ncc(Cc2ccsc2)o1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#16;a:4]:[c:5]:1.[C;D1;H3:6]-[c:7]1:[#7;a:8]:[c:9]:[#8;a:10]:[c:11]:1-[C;H0;D3;+0:12](-[C;D1;H3:13])=[O;H0;D1;+0:14]>>[C;D1;H3:6]-[c:7]1:[#7;a:8]:[c:9]:[#8;a:10]:[c:11]:1-[C;H0;D4;+0:12](-[C;D1;H3:13])(-[OH;D1;+0:14])-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#16;a:4]:[c:5]:1 | null | [] | null | null | null | null | Starting with 3-bromothiophene and 5-acetyl-2,4-dimethyloxazole and following the general method of Example 4 the title compound was prepared. M.p. 132°-133° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | Tertiary alcohol | c1ccsc1 | c1ccsc1 | c1cocn1.c1ccsc1 | Br- | null | null | null | Brc1ccsc1.CC(=O)c1oc(C)nc1C>>Cc1nc(C)c(C(C)(O)c2ccsc2)o1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e1ffdfaddb4c40e0b14bbab38f1940b1 | Brc1ccsc1.CCc1nc(C)c(C(C)=O)o1>>CCc1nc(C)c(C(C)(O)c2ccsc2)o1 | BrC1=CSC=C1.C(C)(=O)C1=C(N=C(O1)CC)C>>C(C)C=1OC(=C(N1)C)C(C)(O)C1=CSC=C1 | Br[c:11]1[cH:12][cH:13][s:14][cH:15]1.[CH3:1][CH2:2][c:3]1[n:4][c:5]([CH3:6])[c:7]([C:8]([CH3:9])=[O:10])[o:16]1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]([CH3:6])[c:7]([C:8]([CH3:9])([OH:10])[c:11]2[cH:12][cH:13][s:14][cH:15]2)[o:16]1 | Brc1ccsc1.CCc1nc(C)c(C(C)=O)o1 | CCc1nc(C)c(C(C)(O)c2ccsc2)o1 | null | null | null | C-C Coupling | Grignard_alcohol | ced8db25e742cc856055ca33877a37cbea1e62e1ac0cab97d987f0994afc50bc | b8801be51258f6ee39fb6aad45dd9677b1b9eed3d6e0018ffb065bca8e787abf | c1ncc(Cc2ccsc2)o1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#16;a:4]:[c:5]:1.[C;D1;H3:6]-[c:7]1:[#7;a:8]:[c:9]:[#8;a:10]:[c:11]:1-[C;H0;D3;+0:12](-[C;D1;H3:13])=[O;H0;D1;+0:14]>>[C;D1;H3:6]-[c:7]1:[#7;a:8]:[c:9]:[#8;a:10]:[c:11]:1-[C;H0;D4;+0:12](-[C;D1;H3:13])(-[OH;D1;+0:14])-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#16;a:4]:[c:5]:1 | null | [] | null | null | null | null | Starting with 3-bromothiophene and 5-acetyl-2-ethyl-4-methyloxazole and following the general method of Example 4 the title compound was prepared. M.p. 77.5°-79° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | Tertiary alcohol | c1ccsc1 | c1ccsc1 | c1cocn1.c1ccsc1 | Br- | null | null | null | Brc1ccsc1.CCc1nc(C)c(C(C)=O)o1>>CCc1nc(C)c(C(C)(O)c2ccsc2)o1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7c881ec5980549f28fcc3efe8598f0f3 | Brc1ccoc1.CCC(=O)c1ocnc1C>>CCC(O)(c1ccoc1)c1ocnc1C | BrC1=COC=C1.CC=1N=COC1C(CC)=O>>O1C=C(C=C1)C(CC)(O)C1=C(N=CO1)C | Br[c:5]1[cH:6][cH:7][o:8][cH:9]1.[CH3:1][CH2:2][C:3](=[O:4])[c:10]1[o:11][cH:12][n:13][c:14]1[CH3:15]>>[CH3:1][CH2:2][C:3]([OH:4])([c:5]1[cH:6][cH:7][o:8][cH:9]1)[c:10]1[o:11][cH:12][n:13][c:14]1[CH3:15] | Brc1ccoc1.CCC(=O)c1ocnc1C | CCC(O)(c1ccoc1)c1ocnc1C | null | null | null | C-C Coupling | Grignard_alcohol | 387b0cbaf6cbd397bd265f915bdee829fa87b6f14aea3f8eab7ebee183cf19f8 | b8801be51258f6ee39fb6aad45dd9677b1b9eed3d6e0018ffb065bca8e787abf | c1cc(Cc2cnco2)co1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#8;a:4]:[c:5]:1.[C;D1;H3:6]-[c:7]1:[#7;a:8]:[c:9]:[#8;a:10]:[c:11]:1-[C;H0;D3;+0:12](=[O;H0;D1;+0:13])-[C:14]-[C;D1;H3:15]>>[C;D1;H3:6]-[c:7]1:[#7;a:8]:[c:9]:[#8;a:10]:[c:11]:1-[C;H0;D4;+0:12](-[OH;D1;+0:13])(-[C:14]-[C;D1;H3:15])-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#8;a:4]:[c:5]:1 | null | [] | null | null | null | null | Starting with 3-bromofuran and 4-methyl-5-propionyloxazole and following the general method of Example 4 the title compound was prepared.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | Tertiary alcohol | c1ccoc1 | c1ccoc1 | c1ccoc1.c1cocn1 | Br- | null | null | null | Brc1ccoc1.CCC(=O)c1ocnc1C>>CCC(O)(c1ccoc1)c1ocnc1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-efc8b15097db4a8899ec13fa077a9b2a | Brc1ccoc1.CCc1nc(C)c(C(C)=O)o1>>CCc1nc(C)c(C(C)(O)c2ccoc2)o1 | BrC1=COC=C1.C(C)(=O)C1=C(N=C(O1)CC)C>>C(C)C=1OC(=C(N1)C)C(C)(O)C1=COC=C1 | Br[c:11]1[cH:12][cH:13][o:14][cH:15]1.[CH3:1][CH2:2][c:3]1[n:4][c:5]([CH3:6])[c:7]([C:8]([CH3:9])=[O:10])[o:16]1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]([CH3:6])[c:7]([C:8]([CH3:9])([OH:10])[c:11]2[cH:12][cH:13][o:14][cH:15]2)[o:16]1 | Brc1ccoc1.CCc1nc(C)c(C(C)=O)o1 | CCc1nc(C)c(C(C)(O)c2ccoc2)o1 | null | null | null | C-C Coupling | Grignard_alcohol | 387b0cbaf6cbd397bd265f915bdee829fa87b6f14aea3f8eab7ebee183cf19f8 | b8801be51258f6ee39fb6aad45dd9677b1b9eed3d6e0018ffb065bca8e787abf | c1cc(Cc2cnco2)co1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#8;a:4]:[c:5]:1.[C;D1;H3:6]-[c:7]1:[#7;a:8]:[c:9]:[#8;a:10]:[c:11]:1-[C;H0;D3;+0:12](-[C;D1;H3:13])=[O;H0;D1;+0:14]>>[C;D1;H3:6]-[c:7]1:[#7;a:8]:[c:9]:[#8;a:10]:[c:11]:1-[C;H0;D4;+0:12](-[C;D1;H3:13])(-[OH;D1;+0:14])-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#8;a:4]:[c:5]:1 | null | [] | null | null | null | null | Starting with 3-bromofuran and 5-acetyl-2-ethyl-4-methyloxazole and following the general method of Example 4 the title compound was prepared.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | Tertiary alcohol | c1ccoc1 | c1ccoc1 | c1cocn1.c1ccoc1 | Br- | null | null | null | Brc1ccoc1.CCc1nc(C)c(C(C)=O)o1>>CCc1nc(C)c(C(C)(O)c2ccoc2)o1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8c46d271dc924094b2300f23ad9e41d8 | Brc1ccsc1.CCC(=O)c1oc(C)nc1C>>CCC(O)(c1ccsc1)c1oc(C)nc1C | BrC1=CSC=C1.CC=1OC(=C(N1)C)C(CC)=O>>CC=1OC(=C(N1)C)C(CC)(O)C1=CSC=C1 | Br[c:5]1[cH:6][cH:7][s:8][cH:9]1.[CH3:1][CH2:2][C:3](=[O:4])[c:10]1[o:11][c:12]([CH3:13])[n:14][c:15]1[CH3:16]>>[CH3:1][CH2:2][C:3]([OH:4])([c:5]1[cH:6][cH:7][s:8][cH:9]1)[c:10]1[o:11][c:12]([CH3:13])[n:14][c:15]1[CH3:16] | Brc1ccsc1.CCC(=O)c1oc(C)nc1C | CCC(O)(c1ccsc1)c1oc(C)nc1C | null | null | null | C-C Coupling | Grignard_alcohol | ced8db25e742cc856055ca33877a37cbea1e62e1ac0cab97d987f0994afc50bc | b8801be51258f6ee39fb6aad45dd9677b1b9eed3d6e0018ffb065bca8e787abf | c1ncc(Cc2ccsc2)o1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#16;a:4]:[c:5]:1.[C;D1;H3:6]-[c:7]1:[#7;a:8]:[c:9]:[#8;a:10]:[c:11]:1-[C;H0;D3;+0:12](=[O;H0;D1;+0:13])-[C:14]-[C;D1;H3:15]>>[C;D1;H3:6]-[c:7]1:[#7;a:8]:[c:9]:[#8;a:10]:[c:11]:1-[C;H0;D4;+0:12](-[OH;D1;+0:13])(-[C:14]-[C;D1;H3:15])-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#16;a:4]:[c:5]:1 | null | [] | null | null | null | null | Starting with 3-bromothiophene and 2,4-dimethyl-5-propionyloxazole and following the general method of Example 4 the title compound was prepared. Purification by preparative HPLC gave a white solid. M.p. 81°-83° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | Tertiary alcohol | c1ccsc1 | c1ccsc1 | c1ccsc1.c1cocn1 | Br- | null | null | null | Brc1ccsc1.CCC(=O)c1oc(C)nc1C>>CCC(O)(c1ccsc1)c1oc(C)nc1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e9d4ef0ff6ff4c95929f4a2bec5c4a5f | Brc1ccoc1.CC(=O)c1nc(C)oc1C>>Cc1nc(C(C)(O)c2ccoc2)c(C)o1 | BrC1=COC=C1.C(C)(=O)C=1N=C(OC1C)C>>CC=1OC(=C(N1)C(C)(O)C1=COC=C1)C | Br[c:8]1[cH:9][cH:10][o:11][cH:12]1.[CH3:1][c:2]1[n:3][c:4]([C:5]([CH3:6])=[O:7])[c:13]([CH3:14])[o:15]1>>[CH3:1][c:2]1[n:3][c:4]([C:5]([CH3:6])([OH:7])[c:8]2[cH:9][cH:10][o:11][cH:12]2)[c:13]([CH3:14])[o:15]1 | Brc1ccoc1.CC(=O)c1nc(C)oc1C | Cc1nc(C(C)(O)c2ccoc2)c(C)o1 | null | null | null | C-C Coupling | Grignard_alcohol | 387b0cbaf6cbd397bd265f915bdee829fa87b6f14aea3f8eab7ebee183cf19f8 | b8801be51258f6ee39fb6aad45dd9677b1b9eed3d6e0018ffb065bca8e787abf | c1cc(Cc2cocn2)co1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#8;a:3]:[c:4]:[c:5]:1.[C;D1;H3:6]-[c:7]1:[#8;a:8]:[c:9]:[#7;a:10]:[c:11]:1-[C;H0;D3;+0:12](-[C;D1;H3:13])=[O;H0;D1;+0:14]>>[C;D1;H3:6]-[c:7]1:[#8;a:8]:[c:9]:[#7;a:10]:[c:11]:1-[C;H0;D4;+0:12](-[C;D1;H3:13])(-[OH;D1;+0:14])-[c;H0;D3;+0:1]1:[c:2]:[#8;a:3]:[c:4]:[c:5]:1 | null | [] | null | null | null | null | Starting with 3-bromofuran and 4-acetyl-2,5-dimethyloxazole and following the general method of Example 4 the title compound was prepared.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | Tertiary alcohol | c1ccoc1 | c1ccoc1 | c1cocn1.c1ccoc1 | Br- | null | null | null | Brc1ccoc1.CC(=O)c1nc(C)oc1C>>Cc1nc(C(C)(O)c2ccoc2)c(C)o1 |
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