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-c3a75813d0b24864aa4f7cd526efd6aa | ord-23d8b3aa860946449b836e743b5e5189 | Brc1ccc2c(ccn2Cc2ccccc2)c1.OB(O)c1ccccc1>>c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)Br.ClCCl.C([O-])([O-])=O.[K+].[K+].C1(=CC=CC=C1)B(O)O>>C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)C1=CC=CC=C1 | Br[c:11]1[cH:10][c:9]2[cH:8][cH:7][n:6]([CH2:5][c:4]3[cH:3][cH:2][cH:1][cH:22][cH:21]3)[c:20]2[cH:19][cH:18]1.OB(O)[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][n:6]2[cH:7][cH:8][c:9]3[cH:10][c:11](-[c:12]4[cH:13][cH:14][cH:15][cH:16][cH:17]4)[cH:18][cH:19][c:20]23)[cH:21][cH:22]1 | Brc1ccc2c(ccn2Cc2ccccc2)c1.OB(O)c1ccccc1 | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | null | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2] | O1CCOCC1.O | C-C Coupling | Suzuki coupling with boronic acids | 42e21206f0250bb469664981cf521bd21ce6ff7bf8a8e9271f94397f7d3b79cb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#7;a:5]:[c:4]1:[c:6]:[c:7]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:2]:[c:3]:1 | 35 | [{"value": 35.0, "product": "C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 34.5, "product": "C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-Benzyl-5-phenyl-1H-indole was prepared by coupling 1-benzyl-5-bromo-1H-indole (2.72 g, 9.50 mmol), and phenylboronic acid (1.39 g, 11.4 mmol), using [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (0.266 g, 0.326 mmol), and potassium carbonate (2.06 g, 14.9 mmol) in dio... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | HBr.B | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].O1CCOCC1.O | null | null | Brc1ccc2c(ccn2Cc2ccccc2)c1.OB(O)c1ccccc1>C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].O1CCOCC1.O>c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-137b44c12907427ba89083a530a22b08 | CCO.O=C(Cl)C(=O)Cl.c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1>>CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccccc3)cc12 | C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)C1=CC=CC=C1.C(C(=O)Cl)(=O)Cl.C(C)O>>C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)C1=CC=CC=C1)C(C(=O)OCC)=O | [CH3:1][CH2:2][OH:3].Cl[C:4](=[O:5])[C:6](Cl)=[O:7].[cH:8]1[cH:9][n:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19][cH:20][c:21](-[c:22]3[cH:23][cH:24][cH:25][cH:26][cH:27]3)[cH:28][c:29]12>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[c:8]1[cH:9][n:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16... | CCO.O=C(Cl)C(=O)Cl.c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccccc3)cc12 | null | null | null | C-C Coupling | OtherReaction | e42beb79999369525e781f5f2a8c25a764f237d2f2302bca9902d8152413d7f2 | b36dbf7958ca5ae3ba65aceed13fac6c31bf5a9975134271733ce2a3346931a4 | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](-Cl)=[O;D1;H0:4].[C;D1;H3:5]-[C:6]-[OH;D1;+0:7].[C:8]-[#7;a:9]1:[c:10]:[cH;D2;+0:11]:[c:12](:[c:13]):[c:14]:1:[c:15]>>[C:8]-[#7;a:9]1:[c:10]:[c;H0;D3;+0:11](-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C:6]-[C;D1;H3:5]):[c:12](:[c:13]):[c:14]:... | 66 | [{"value": 66.0, "product": "C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)C1=CC=CC=C1)C(C(=O)OCC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Ethyl {1-benzyl-5-phenyl-1H-indol-3-yl}(oxo)acetate was prepared from 1-benzyl-5-phenyl-1H-indole (0.846 g, 2.99 mmol), oxalyl chloride (0.78 mL, 9.0 mmol), and ethanol (2 mL), following the procedure described in Step 3 of Example 1. Purification by flash chromatography (Biotage apparatus) using 5-7.5% ethyl acetate i... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary alcohol | Ketone.Ester | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | HCl | null | null | null | CCO.O=C(Cl)C(=O)Cl.c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1>>CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccccc3)cc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c63258f45f3848609e0a8ea5042f1287 | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccccc3)cc12>>O=C(O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccccc3)cc12 | C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)C1=CC=CC=C1)C(C(=O)OCC)=O.[OH-].[K+]>>C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)C1=CC=CC=C1)C(C(=O)O)=O | CC[O:3][C:2](=[O:1])[C:4](=[O:5])[c:6]1[cH:7][n:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]2[cH:17][cH:18][c:19](-[c:20]3[cH:21][cH:22][cH:23][cH:24][cH:25]3)[cH:26][c:27]12>>[O:1]=[C:2]([OH:3])[C:4](=[O:5])[c:6]1[cH:7][n:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]2[cH:17][cH:18][c:19]... | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccccc3)cc12 | O=C(O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccccc3)cc12 | null | null | O.C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](=[O;D1;H0:5])-[c:6]:[c:7]:[#7;a:8]>>[#7;a:8]:[c:7]:[c:6]-[C:4](=[O;D1;H0:5])-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 62.3 | [{"value": 62.0, "product": "C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)C1=CC=CC=C1)C(C(=O)O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.3, "product": "C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)C1=CC=CC=C1)C(C(=O)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | {1-Benzyl-5-phenyl-1H-indol-3-yl}(oxo)acetic acid was prepared from ethyl {1-benzyl-5-phenyl-1H-indol-3-yl}(oxo)acetate (0.680 g, 1.77 mmol), and potassium hydroxide (0.322 g, 5.74 mmol) in THF (10 mL) and water (10 mL), following the procedure described in Step 4 of Example 5. Crystallization from acetonitrile, and dr... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | Other | O.C1CCOC1 | null | null | CCOC(=O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccccc3)cc12>O.C1CCOC1>O=C(O)C(=O)c1cn(Cc2ccccc2)c2ccc(-c3ccccc3)cc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-83ac8374c5154999b98d4a40fefbd012 | Brc1ccc2[nH]ccc2c1.Cc1ccc(CBr)cc1>>Cc1ccc(Cn2ccc3cc(Br)ccc32)cc1 | [H-].[Na+].BrC=1C=C2C=CNC2=CC1.CC1=CC=C(CBr)C=C1>>BrC=1C=C2C=CN(C2=CC1)CC1=CC=C(C=C1)C | [nH:7]1[cH:8][cH:9][c:10]2[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]12.Br[CH2:6][c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:18][cH:17]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][n:7]2[cH:8][cH:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]23)[cH:17][cH:18]1 | Brc1ccc2[nH]ccc2c1.Cc1ccc(CBr)cc1 | Cc1ccc(Cn2ccc3cc(Br)ccc32)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 92cc004fc3e2a92f5c9aa0385cdf93f1126e35d5aa485f4f5fe9240c9543c8fe | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cn2ccc3ccccc32)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[c:5]:[c:6]1:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[c:5]:[c:6]1:[c:7]:[c:8]:[c:9]:[n;H0;D3;+0:10]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 1 | HOUR | NaH (60%, 2.53 g, 63.1 mmol) was added portionwise to a stirring solution of 5-bromoindole (8.25 g, 42.1 mmol) in DMF (80 mL) at 0° C. under a nitrogen atmosphere over a period of 10 min. The mixture was then warmed up to room temperature. After the reaction mixture was stirred at room temperature for 1 hour, 4-methylb... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | HBr | CN(C)C=O | null | 1 | Brc1ccc2[nH]ccc2c1.Cc1ccc(CBr)cc1>CN(C)C=O>Cc1ccc(Cn2ccc3cc(Br)ccc32)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c8100daffee34b4a9962e3d643e03b3a | Cc1ccc(Cn2ccc3cc(Br)ccc32)cc1.OB(O)c1ccccc1>>Cc1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | BrC=1C=C2C=CN(C2=CC1)CC1=CC=C(C=C1)C.C1(=CC=CC=C1)B(O)O.C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>>CC1=CC=C(CN2C=CC3=CC(=CC=C23)C2=CC=CC=C2)C=C1 | Br[c:12]1[cH:11][c:10]2[cH:9][cH:8][n:7]([CH2:6][c:5]3[cH:4][cH:3][c:2]([CH3:1])[cH:23][cH:22]3)[c:21]2[cH:20][cH:19]1.OB(O)[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][n:7]2[cH:8][cH:9][c:10]3[cH:11][c:12](-[c:13]4[cH:14][cH:15][cH:16][cH:17][cH:18]4)[cH:19][cH:20][c:21]23)[cH:22... | Cc1ccc(Cn2ccc3cc(Br)ccc32)cc1.OB(O)c1ccccc1 | Cc1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | null | null | O.O1CCOCC1.O | C-C Coupling | Suzuki coupling with boronic acids | 42e21206f0250bb469664981cf521bd21ce6ff7bf8a8e9271f94397f7d3b79cb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#7;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:7]:[c:6]:1 | 49 | [{"value": 49.0, "product": "CC1=CC=C(CN2C=CC3=CC(=CC=C23)C2=CC=CC=C2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.5, "product": "CC1=CC=C(CN2C=CC3=CC(=CC=C23)C2=CC=CC=C2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 2 | DAY | A mixture of 5-bromo-1-(4-methylbenzyl)-1H-indole (1.0 g, 3.33 mmol), benzeneboronic acid (0.621 g, 5.0 mmol), potassium carbonate (0.691 g, 5.0 mmol), and [1′1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II) complex with methylenechloride (1:1) (0.816 g, 1.0 mmol) in dioxane-water (10:1, 16.5 mL) was stirred a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | HBr.B | O.O1CCOCC1.O | 70 | 48 | Cc1ccc(Cn2ccc3cc(Br)ccc32)cc1.OB(O)c1ccccc1>O.O1CCOCC1.O>Cc1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5e7bd16ba5f94b02b3b6a3c660acd8af | Cc1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1.O=C(Cl)C(=O)Cl>>Cc1ccc(Cn2cc(C(=O)C(=O)O)c3cc(-c4ccccc4)ccc32)cc1 | C(C(=O)Cl)(=O)Cl.CC1=CC=C(CN2C=CC3=CC(=CC=C23)C2=CC=CC=C2)C=C1.C1CCOC1>>CC1=CC=C(CN2C=C(C3=CC(=CC=C23)C2=CC=CC=C2)C(C(=O)O)=O)C=C1 | [CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][n:7]2[cH:8][cH:9][c:15]3[cH:16][c:17](-[c:18]4[cH:19][cH:20][cH:21][cH:22][cH:23]4)[cH:24][cH:25][c:26]23)[cH:27][cH:28]1.Cl[C:10](=[O:11])[C:12](Cl)=[O:13]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][n:7]2[cH:8][c:9]([C:10](=[O:11])[C:12](=[O:13])[OH:14])[c:15]3[cH:16][c:17](-[c:18]4... | Cc1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1.O=C(Cl)C(=O)Cl | Cc1ccc(Cn2cc(C(=O)C(=O)O)c3cc(-c4ccccc4)ccc32)cc1 | null | null | null | Acylation | OtherReaction | 9d127b05b36fe9fe6fc80547d3614a823e90d1399390b2ba6617beb8202d8432 | 6b048b617f07704989b0d7eff26dc61c44694ea4e42b339d6d7680e8458e5255 | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](-Cl)=[O;D1;H0:4].[C:5]-[#7;a:6]1:[c:7]:[cH;D2;+0:8]:[c:9](:[c:10]):[c:11]:1:[c:12]>>[C:5]-[#7;a:6]1:[c:7]:[c;H0;D3;+0:8](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](=[O;D1;H0:4])-[O;D1;H1:13]):[c:9](:[c:10]):[c:11]:1:[c:12] | 72 | [{"value": 72.0, "product": "CC1=CC=C(CN2C=C(C3=CC(=CC=C23)C2=CC=CC=C2)C(C(=O)O)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | Oxalyl chloride (0.474 mL, 5.43 mmol) was added dropwise to a stirring solution of 1-(4-methylbenzyl)-5-phenyl-1H-indole (0.46 g, 1.55 mmol) in THF (15 mL) at room temperature over a period of 5 minutes under a nitrogen atmosphere. After the reaction mixture was stirred at room temperature for 4 hours, the reaction was... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide | Carboxylic acid.Ketone | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | Other | null | null | 4 | Cc1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1.O=C(Cl)C(=O)Cl>>Cc1ccc(Cn2cc(C(=O)C(=O)O)c3cc(-c4ccccc4)ccc32)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f9b1ebdd05e34c87bf371a2dd67ee2c3 | Cc1ccc(Cn2ccc3cc(Br)ccc32)cc1.OB(O)c1ccc(OC(F)(F)F)cc1>>Cc1ccc(Cn2ccc3cc(-c4ccc(OC(F)(F)F)cc4)ccc32)cc1 | BrC=1C=C2C=CN(C2=CC1)CC1=CC=C(C=C1)C.FC(OC1=CC=C(C=C1)B(O)O)(F)F>>CC1=CC=C(CN2C=CC3=CC(=CC=C23)C2=CC=C(C=C2)OC(F)(F)F)C=C1 | Br[c:12]1[cH:11][c:10]2[cH:9][cH:8][n:7]([CH2:6][c:5]3[cH:4][cH:3][c:2]([CH3:1])[cH:28][cH:27]3)[c:26]2[cH:25][cH:24]1.OB(O)[c:13]1[cH:14][cH:15][c:16]([O:17][C:18]([F:19])([F:20])[F:21])[cH:22][cH:23]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][n:7]2[cH:8][cH:9][c:10]3[cH:11][c:12](-[c:13]4[cH:14][cH:15][c:16]([O:17][C:1... | Cc1ccc(Cn2ccc3cc(Br)ccc32)cc1.OB(O)c1ccc(OC(F)(F)F)cc1 | Cc1ccc(Cn2ccc3cc(-c4ccc(OC(F)(F)F)cc4)ccc32)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 42e21206f0250bb469664981cf521bd21ce6ff7bf8a8e9271f94397f7d3b79cb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#7;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:7]:[c:6]:1 | null | [] | null | null | null | null | The title compound was prepared from 5-bromo-1-(4-methylbenzyl)-1H-indole (Step 1 of Example 25) and 4-(trifluoromethoxy)phenylboronic acid in substantially the same manner, as described in Step 2 of Example 25. The product was obtained as an oil. Mass spectrum (ESI, [M+H]+) m/z 382. 1HNMR (300 MHz, DMSO-d6): δ 7.83 (s... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | HBr.B | null | null | null | Cc1ccc(Cn2ccc3cc(Br)ccc32)cc1.OB(O)c1ccc(OC(F)(F)F)cc1>>Cc1ccc(Cn2ccc3cc(-c4ccc(OC(F)(F)F)cc4)ccc32)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f4f94b3fac1948a2b4bd89a4f06f205a | Brc1ccc2[nH]ccc2c1.Fc1ccc(CBr)cc1>>Fc1ccc(Cn2ccc3cc(Br)ccc32)cc1 | FC1=CC=C(CBr)C=C1.BrC=1C=C2C=CNC2=CC1>>BrC=1C=C2C=CN(C2=CC1)CC1=CC=C(C=C1)F | [nH:7]1[cH:8][cH:9][c:10]2[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]12.Br[CH2:6][c:5]1[cH:4][cH:3][c:2]([F:1])[cH:18][cH:17]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][n:7]2[cH:8][cH:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]23)[cH:17][cH:18]1 | Brc1ccc2[nH]ccc2c1.Fc1ccc(CBr)cc1 | Fc1ccc(Cn2ccc3cc(Br)ccc32)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 92cc004fc3e2a92f5c9aa0385cdf93f1126e35d5aa485f4f5fe9240c9543c8fe | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cn2ccc3ccccc32)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[c:5]:[c:6]1:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[c:5]:[c:6]1:[c:7]:[c:8]:[c:9]:[n;H0;D3;+0:10]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The title compound was prepared from 4-fluorobenzyl bromide and 5-bromoindole in substantially the same manner, as described in Step 1 of Example 25. The product was obtained as a white solid; mp: 57-58° C. Mass spectrum (APCI, [M+H]+) m/z 304. 1 HNMR (400 MHz, DMSO-d6): δ 7.73 (d, 1H, J=1.8 Hz), 7.55 (d, 1H, J=3.2 Hz)... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | HBr | null | null | null | Brc1ccc2[nH]ccc2c1.Fc1ccc(CBr)cc1>>Fc1ccc(Cn2ccc3cc(Br)ccc32)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1a929905409f4df2874edb2ef39fb252 | Fc1ccc(Cn2ccc3cc(Br)ccc32)cc1.OB(O)c1ccc(OC(F)(F)F)cc1>>Fc1ccc(Cn2ccc3cc(-c4ccc(OC(F)(F)F)cc4)ccc32)cc1 | BrC=1C=C2C=CN(C2=CC1)CC1=CC=C(C=C1)F.FC(OC1=CC=C(C=C1)B(O)O)(F)F>>FC1=CC=C(CN2C=CC3=CC(=CC=C23)C2=CC=C(C=C2)OC(F)(F)F)C=C1 | Br[c:12]1[cH:11][c:10]2[cH:9][cH:8][n:7]([CH2:6][c:5]3[cH:4][cH:3][c:2]([F:1])[cH:28][cH:27]3)[c:26]2[cH:25][cH:24]1.OB(O)[c:13]1[cH:14][cH:15][c:16]([O:17][C:18]([F:19])([F:20])[F:21])[cH:22][cH:23]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][n:7]2[cH:8][cH:9][c:10]3[cH:11][c:12](-[c:13]4[cH:14][cH:15][c:16]([O:17][C:18]([... | Fc1ccc(Cn2ccc3cc(Br)ccc32)cc1.OB(O)c1ccc(OC(F)(F)F)cc1 | Fc1ccc(Cn2ccc3cc(-c4ccc(OC(F)(F)F)cc4)ccc32)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 42e21206f0250bb469664981cf521bd21ce6ff7bf8a8e9271f94397f7d3b79cb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#7;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:7]:[c:6]:1 | null | [] | null | null | null | null | The title compound was prepared from 5-bromo-1-(4-fluorobenzyl)-1H-indole and 4-(trifluoromethoxy)phenylboronic acid in substantially the same manner, as described in Step 2 of Example 25. The product was obtained as an oil. Mass spectrum (ESI, [M+H]+) m/z 386. 1HNMR (300 MHz, DMSO-d6): δ 7.84 (s, 1H), 7.76 (d, 2H, J=8... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | HBr.B | null | null | null | Fc1ccc(Cn2ccc3cc(Br)ccc32)cc1.OB(O)c1ccc(OC(F)(F)F)cc1>>Fc1ccc(Cn2ccc3cc(-c4ccc(OC(F)(F)F)cc4)ccc32)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-879c708c3c7d4ea29f1ee08d3d08a6d4 | Fc1ccc(Cn2ccc3cc(Br)ccc32)cc1.OB(O)c1ccccc1>>Fc1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | BrC=1C=C2C=CN(C2=CC1)CC1=CC=C(C=C1)F.C1(=CC=CC=C1)B(O)O>>FC1=CC=C(CN2C=CC3=CC(=CC=C23)C2=CC=CC=C2)C=C1 | Br[c:12]1[cH:11][c:10]2[cH:9][cH:8][n:7]([CH2:6][c:5]3[cH:4][cH:3][c:2]([F:1])[cH:23][cH:22]3)[c:21]2[cH:20][cH:19]1.OB(O)[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][n:7]2[cH:8][cH:9][c:10]3[cH:11][c:12](-[c:13]4[cH:14][cH:15][cH:16][cH:17][cH:18]4)[cH:19][cH:20][c:21]23)[cH:22][cH... | Fc1ccc(Cn2ccc3cc(Br)ccc32)cc1.OB(O)c1ccccc1 | Fc1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 42e21206f0250bb469664981cf521bd21ce6ff7bf8a8e9271f94397f7d3b79cb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#7;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:7]:[c:6]:1 | null | [] | null | null | null | null | The title compound was prepared from 5-bromo-1-(4-fluorobenzyl)-1H-indole (Step 1 of Example 27) and benzeneboronic acid in substantially the same manner, as described in Step 2 of Example 25. The product was obtained as an oil. Mass spectrum (ESI, [M+H]+) m/z 302. 1HNMR (300 MHz, DMSO-d6): δ 7.81 (s, 1H), 7.63 (d, 2H,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | HBr.B | null | null | null | Fc1ccc(Cn2ccc3cc(Br)ccc32)cc1.OB(O)c1ccccc1>>Fc1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8c462a37513741d69cfce9855fa61341 | Brc1ccc2[nH]ccc2c1.CCCCBr>>CCCCn1ccc2cc(Br)ccc21 | BrCCCC.BrC=1C=C2C=CNC2=CC1>>BrC=1C=C2C=CN(C2=CC1)CCCC | [nH:5]1[cH:6][cH:7][c:8]2[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]12.Br[CH2:4][CH2:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[cH:6][cH:7][c:8]2[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]12 | Brc1ccc2[nH]ccc2c1.CCCCBr | CCCCn1ccc2cc(Br)ccc21 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 92cc004fc3e2a92f5c9aa0385cdf93f1126e35d5aa485f4f5fe9240c9543c8fe | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc2[nH]ccc2c1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[c:4]:[c:5]1:[c:6]:[c:7]:[c:8]:[nH;D2;+0:9]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:9]1:[c:8]:[c:7]:[c:6]:[c:5]:1:[c:4] | null | [] | null | null | null | null | The title compound was prepared from 1-bromobutane (11 mL, 101 mmol) and 5-bromoindole (20 g, 101 mmol) in substantially the same manner, as described in Step 1 of Example 25. The product was obtained as an oil. Mass spectrum (ESI, [M+H]+) m/z 252. 1HNMR (300 MHz, DMSO-d6): δ 7.71 (d, 1H, J=1.9 Hz), 7.46 (d, 1H, J=8.7 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HBr | null | null | null | Brc1ccc2[nH]ccc2c1.CCCCBr>>CCCCn1ccc2cc(Br)ccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-916330ebdd15492aaf890057b09b7397 | CCCCn1ccc2cc(Br)ccc21.OB(O)c1ccc(Cl)cc1>>CCCCn1ccc2cc(-c3ccc(Cl)cc3)ccc21 | BrC=1C=C2C=CN(C2=CC1)CCCC.ClC1=CC=C(C=C1)B(O)O>>C(CCC)N1C=CC2=CC(=CC=C12)C1=CC=C(C=C1)Cl | Br[c:10]1[cH:9][c:8]2[cH:7][cH:6][n:5]([CH2:4][CH2:3][CH2:2][CH3:1])[c:20]2[cH:19][cH:18]1.OB(O)[c:11]1[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]1>>[CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[cH:6][cH:7][c:8]2[cH:9][c:10](-[c:11]3[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]3)[cH:18][cH:19][c:20]12 | CCCCn1ccc2cc(Br)ccc21.OB(O)c1ccc(Cl)cc1 | CCCCn1ccc2cc(-c3ccc(Cl)cc3)ccc21 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 42e21206f0250bb469664981cf521bd21ce6ff7bf8a8e9271f94397f7d3b79cb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc3[nH]ccc3c2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#7;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:7]:[c:6]:1 | null | [] | null | null | null | null | The title compound was prepared from 5-bromo-1-butyl-1H-indole and 4-chlorophenylboronic acid in substantially the same manner, as described in Step 2 of Example 25. The product was obtained as an oil. Mass spectrum (ESI, [M+H]+) m/z 284. 1HNMR (400 MHz, DMSO-d6): δ 7.81 (s, 1H), 7.67 (d, 2H, J=8.56 Hz), 7.54 (d, 1H, J... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccc2[nH]ccc2c1.c1ccccc1 | HBr.B | null | null | null | CCCCn1ccc2cc(Br)ccc21.OB(O)c1ccc(Cl)cc1>>CCCCn1ccc2cc(-c3ccc(Cl)cc3)ccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-26f7f0c637c0454d8a1d2894c49931ac | CCCCn1ccc2cc(Br)ccc21.OB(O)c1cccc(Cl)c1>>CCCCn1ccc2cc(-c3cccc(Cl)c3)ccc21 | BrC=1C=C2C=CN(C2=CC1)CCCC.ClC=1C=C(C=CC1)B(O)O>>C(CCC)N1C=CC2=CC(=CC=C12)C1=CC(=CC=C1)Cl | Br[c:10]1[cH:9][c:8]2[cH:7][cH:6][n:5]([CH2:4][CH2:3][CH2:2][CH3:1])[c:20]2[cH:19][cH:18]1.OB(O)[c:11]1[cH:12][cH:13][cH:14][c:15]([Cl:16])[cH:17]1>>[CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[cH:6][cH:7][c:8]2[cH:9][c:10](-[c:11]3[cH:12][cH:13][cH:14][c:15]([Cl:16])[cH:17]3)[cH:18][cH:19][c:20]12 | CCCCn1ccc2cc(Br)ccc21.OB(O)c1cccc(Cl)c1 | CCCCn1ccc2cc(-c3cccc(Cl)c3)ccc21 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 42e21206f0250bb469664981cf521bd21ce6ff7bf8a8e9271f94397f7d3b79cb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc3[nH]ccc3c2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#7;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:7]:[c:6]:1 | null | [] | null | null | null | null | The title compound was prepared from 5-bromo-1-butyl-1H-indole (Step 1 of Example 29) and 3-chlorophenylboronic acid in substantially the same manner, as described in Step 2 of Example 25. The product was obtained as an oil. Mass spectrum (APCI, [M+H]+) m/z 284. 1HNMR (400 MHz, DMSO-d6): δ 7.85 (s, 1H), 7.69 (s, 1H), 7... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccc2[nH]ccc2c1.c1ccccc1 | HBr.B | null | null | null | CCCCn1ccc2cc(Br)ccc21.OB(O)c1cccc(Cl)c1>>CCCCn1ccc2cc(-c3cccc(Cl)c3)ccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cced9169477847a6bc9e85b61cea955c | CCCCn1ccc2cc(Br)ccc21.COc1cccc(B(O)O)c1>>CCCCn1ccc2cc(-c3cccc(OC)c3)ccc21 | BrC=1C=C2C=CN(C2=CC1)CCCC.COC=1C=C(C=CC1)B(O)O>>C(CCC)N1C=CC2=CC(=CC=C12)C1=CC(=CC=C1)OC | Br[c:10]1[cH:9][c:8]2[cH:7][cH:6][n:5]([CH2:4][CH2:3][CH2:2][CH3:1])[c:21]2[cH:20][cH:19]1.OB(O)[c:11]1[cH:12][cH:13][cH:14][c:15]([O:16][CH3:17])[cH:18]1>>[CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[cH:6][cH:7][c:8]2[cH:9][c:10](-[c:11]3[cH:12][cH:13][cH:14][c:15]([O:16][CH3:17])[cH:18]3)[cH:19][cH:20][c:21]12 | CCCCn1ccc2cc(Br)ccc21.COc1cccc(B(O)O)c1 | CCCCn1ccc2cc(-c3cccc(OC)c3)ccc21 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 42e21206f0250bb469664981cf521bd21ce6ff7bf8a8e9271f94397f7d3b79cb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc3[nH]ccc3c2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#7;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:7]:[c:6]:1 | null | [] | null | null | null | null | The title compound was prepared from 5-bromo-1-butyl-1H-indole (Step 1 of Example 29) and 3-methoxyphenylboronic acid in substantially the same manner, as described in Step 2 of Example 25. The product was obtained as an oil. Mass spectrum (APCI, [M+H]+) m/z 280. 1HNMR (300 MHz, DMSO-d6): δ 7.81 (s, 1H), 7.52 (d, 1H, J... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccc2[nH]ccc2c1.c1ccccc1 | HBr.B | null | null | null | CCCCn1ccc2cc(Br)ccc21.COc1cccc(B(O)O)c1>>CCCCn1ccc2cc(-c3cccc(OC)c3)ccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0c32c86514d84644a64ee65e2a0d2648 | CCCCn1ccc2cc(Br)ccc21.COc1ccc(B(O)O)cc1>>CCCCn1ccc2cc(-c3ccc(OC)cc3)ccc21 | BrC=1C=C2C=CN(C2=CC1)CCCC.COC1=CC=C(C=C1)B(O)O>>C(CCC)N1C=CC2=CC(=CC=C12)C1=CC=C(C=C1)OC | Br[c:10]1[cH:9][c:8]2[cH:7][cH:6][n:5]([CH2:4][CH2:3][CH2:2][CH3:1])[c:21]2[cH:20][cH:19]1.OB(O)[c:11]1[cH:12][cH:13][c:14]([O:15][CH3:16])[cH:17][cH:18]1>>[CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[cH:6][cH:7][c:8]2[cH:9][c:10](-[c:11]3[cH:12][cH:13][c:14]([O:15][CH3:16])[cH:17][cH:18]3)[cH:19][cH:20][c:21]12 | CCCCn1ccc2cc(Br)ccc21.COc1ccc(B(O)O)cc1 | CCCCn1ccc2cc(-c3ccc(OC)cc3)ccc21 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 42e21206f0250bb469664981cf521bd21ce6ff7bf8a8e9271f94397f7d3b79cb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc3[nH]ccc3c2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#7;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:7]:[c:6]:1 | null | [] | null | null | null | null | The title compound was prepared from 5-bromo-1-butyl-1H-indole (Step 1 of Example 29) and 4-methoxyphenylboronic acid in substantially the same manner, as described in Step 2 of Example 25. The product was obtained as an oil. Mass spectrum (ESI, [M+H]+) m/z 280.1 HNMR (400 MHz, DMSO-d6): δ 7.72 (s, 1H), 7.58 (dd, 2H, J... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccc2[nH]ccc2c1.c1ccccc1 | HBr.B | null | null | null | CCCCn1ccc2cc(Br)ccc21.COc1ccc(B(O)O)cc1>>CCCCn1ccc2cc(-c3ccc(OC)cc3)ccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-473ccea54dc34b72b66077d4b107335b | CCCCn1ccc2cc(Br)ccc21.OB(O)c1ccc(C(F)(F)F)cc1>>CCCCn1ccc2cc(-c3ccc(C(F)(F)F)cc3)ccc21 | BrC=1C=C2C=CN(C2=CC1)CCCC.FC(C1=CC=C(C=C1)B(O)O)(F)F>>C(CCC)N1C=CC2=CC(=CC=C12)C1=CC=C(C=C1)C(F)(F)F | Br[c:10]1[cH:9][c:8]2[cH:7][cH:6][n:5]([CH2:4][CH2:3][CH2:2][CH3:1])[c:23]2[cH:22][cH:21]1.OB(O)[c:11]1[cH:12][cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20]1>>[CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[cH:6][cH:7][c:8]2[cH:9][c:10](-[c:11]3[cH:12][cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20]3)[cH:21][cH:... | CCCCn1ccc2cc(Br)ccc21.OB(O)c1ccc(C(F)(F)F)cc1 | CCCCn1ccc2cc(-c3ccc(C(F)(F)F)cc3)ccc21 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 42e21206f0250bb469664981cf521bd21ce6ff7bf8a8e9271f94397f7d3b79cb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc3[nH]ccc3c2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#7;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:7]:[c:6]:1 | null | [] | null | null | null | null | The title compound was prepared from 5-bromo-1-butyl-1H-indole (Step 1 of Example 29) and 4-trifluoromethylphenylboronic acid in substantially the same manner, as described in Step 2 of Example 25. The product was obtained as an oil, mp: 52-53° C. Mass spectrum (APCI, [M+H]+) m/z 318. 1HNMR (400 MHz, DMSO-d6): δ 7.91-7... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccc2[nH]ccc2c1.c1ccccc1 | HBr.B | null | null | null | CCCCn1ccc2cc(Br)ccc21.OB(O)c1ccc(C(F)(F)F)cc1>>CCCCn1ccc2cc(-c3ccc(C(F)(F)F)cc3)ccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7315e87d178f4f0fa5176d9d518a0505 | Brc1ccc2[nH]ccc2c1.CC(C)(C)c1ccc(CBr)cc1>>CC(C)(C)c1ccc(Cn2ccc3cc(Br)ccc32)cc1 | C(C)(C)(C)C1=CC=C(CBr)C=C1.BrC=1C=C2C=CNC2=CC1>>BrC=1C=C2C=CN(C2=CC1)CC1=CC=C(C=C1)C(C)(C)C | [nH:10]1[cH:11][cH:12][c:13]2[cH:14][c:15]([Br:16])[cH:17][cH:18][c:19]12.Br[CH2:9][c:8]1[cH:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:21][cH:20]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][n:10]2[cH:11][cH:12][c:13]3[cH:14][c:15]([Br:16])[cH:17][cH:18][c:19]23)[cH:20][cH:21]1 | Brc1ccc2[nH]ccc2c1.CC(C)(C)c1ccc(CBr)cc1 | CC(C)(C)c1ccc(Cn2ccc3cc(Br)ccc32)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 92cc004fc3e2a92f5c9aa0385cdf93f1126e35d5aa485f4f5fe9240c9543c8fe | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cn2ccc3ccccc32)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[c:5]:[c:6]1:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[c:5]:[c:6]1:[c:7]:[c:8]:[c:9]:[n;H0;D3;+0:10]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 97 | [{"value": 97.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared from 4-(tert-butyl)benzyl bromide (180 g, 768 mmol) and 5-bromoindole (152 g, 768 mmol) in substantially the same manner, as described in Step 1 of Example 25. The product (257 g, 97%) was obtained as a yellow solid, mp: 108-109° C. Mass spectrum (ESI, [M+H]+) m/z 342. 1HNMR (400 MHz, DM... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | HBr | null | null | null | Brc1ccc2[nH]ccc2c1.CC(C)(C)c1ccc(CBr)cc1>>CC(C)(C)c1ccc(Cn2ccc3cc(Br)ccc32)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f29b65b14c4c478ab1b106ae40f55161 | CC(C)(C)c1ccc(Cn2ccc3cc(Br)ccc32)cc1.Cc1cccc(B(O)O)c1>>Cc1cccc(-c2ccc3c(ccn3Cc3ccc(C(C)(C)C)cc3)c2)c1 | CC=1C=C(C=CC1)B(O)O.BrC=1C=C2C=CN(C2=CC1)CC1=CC=C(C=C1)C(C)(C)C.CC=1C=C(C=CC1)B(O)O.C([O-])([O-])=O.[K+].[K+].BrC=1C=C2C=CN(C2=CC1)CC1=CC=C(C=C1)C(C)(C)C>>C(C)(C)(C)C1=CC=C(CN2C=CC3=CC(=CC=C23)C2=CC(=CC=C2)C)C=C1 | Br[c:7]1[cH:8][cH:9][c:10]2[c:11]([cH:12][cH:13][n:14]2[CH2:15][c:16]2[cH:17][cH:18][c:19]([C:20]([CH3:21])([CH3:22])[CH3:23])[cH:24][cH:25]2)[cH:26]1.OB(O)[c:6]1[cH:5][cH:4][cH:3][c:2]([CH3:1])[cH:27]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]3[c:11]([cH:12][cH:13][n:14]3[CH2:15][c:16]3[cH:17][cH... | CC(C)(C)c1ccc(Cn2ccc3cc(Br)ccc32)cc1.Cc1cccc(B(O)O)c1 | Cc1cccc(-c2ccc3c(ccn3Cc3ccc(C(C)(C)C)cc3)c2)c1 | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | O1CCOCC1.O | C-C Coupling | Suzuki coupling with boronic acids | 42e21206f0250bb469664981cf521bd21ce6ff7bf8a8e9271f94397f7d3b79cb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#7;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:7]:[c:6]:1 | 73 | [{"value": 73.0, "product": "C(C)(C)(C)C1=CC=C(CN2C=CC3=CC(=CC=C23)C2=CC(=CC=C2)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.9, "product": "C(C)(C)(C)C1=CC=C(CN2C=CC3=CC(=CC=C23)C2=CC(=CC=C2)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | The mixture of 5-bromo-1-(4-tert-butylbenzyl)-1H-indole (67.5 g, 197.2 mmol), 3-methylbenzeneboronic acid (27.6 g, 197.2 mmol), potassium carbonate (27.2 g, 493 mmol), palladium(II) acetate (0.338 g) and tetrabutylammonium bromide (63.5 g, 197.2 mmol) in 10% dioxane in water (degassed, 1.72 L) was stirred at 70° C. The... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | HBr.B | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O1CCOCC1.O | 70 | null | CC(C)(C)c1ccc(Cn2ccc3cc(Br)ccc32)cc1.Cc1cccc(B(O)O)c1>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O1CCOCC1.O>Cc1cccc(-c2ccc3c(ccn3Cc3ccc(C(C)(C)C)cc3)c2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9374a454b9cc4db5977db909ad4c6745 | CC(C)(C)c1ccc(Cn2ccc3cc(Br)ccc32)cc1.COc1cccc(B(O)O)c1>>COc1cccc(-c2ccc3c(ccn3Cc3ccc(C(C)(C)C)cc3)c2)c1 | BrC=1C=C2C=CN(C2=CC1)CC1=CC=C(C=C1)C(C)(C)C.COC=1C=C(C=CC1)B(O)O>>C(C)(C)(C)C1=CC=C(CN2C=CC3=CC(=CC=C23)C2=CC(=CC=C2)OC)C=C1 | Br[c:8]1[cH:9][cH:10][c:11]2[c:12]([cH:13][cH:14][n:15]2[CH2:16][c:17]2[cH:18][cH:19][c:20]([C:21]([CH3:22])([CH3:23])[CH3:24])[cH:25][cH:26]2)[cH:27]1.OB(O)[c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:28]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]3[c:12]([cH:13][cH:14][n:15]3[CH2:16][c:17... | CC(C)(C)c1ccc(Cn2ccc3cc(Br)ccc32)cc1.COc1cccc(B(O)O)c1 | COc1cccc(-c2ccc3c(ccn3Cc3ccc(C(C)(C)C)cc3)c2)c1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 42e21206f0250bb469664981cf521bd21ce6ff7bf8a8e9271f94397f7d3b79cb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#7;a:5]:[c:4]1:[c:6]:[c:7]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:2]:[c:3]:1 | null | [] | null | null | null | null | The title compound was prepared from 5-bromo-1-[4-(tert-butyl)benzyl]-1H-indole (Step 1 of Example 34) and 3-methoxyphenylboronic acid in substantially the same manner, as described in Step 2 of Example 25. The product was obtained as an oil. Mass spectrum (ESI, [M+H]+) m/z 370. 1HNMR (400 MHz, DMSO-d6): δ 7.81 (s, 1H)... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | HBr.B | null | null | null | CC(C)(C)c1ccc(Cn2ccc3cc(Br)ccc32)cc1.COc1cccc(B(O)O)c1>>COc1cccc(-c2ccc3c(ccn3Cc3ccc(C(C)(C)C)cc3)c2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-33fce8c9c52d453897e4300df2d0ba90 | CC(C)(C)c1ccc(B(O)O)cc1.CC(C)(C)c1ccc(Cn2ccc3cc(Br)ccc32)cc1>>CC(C)(C)c1ccc(Cn2ccc3cc(-c4ccc(C(C)(C)C)cc4)ccc32)cc1 | BrC=1C=C2C=CN(C2=CC1)CC1=CC=C(C=C1)C(C)(C)C.C(C)(C)(C)C1=CC=C(C=C1)B(O)O>>C(C)(C)(C)C1=CC=C(CN2C=CC3=CC(=CC=C23)C2=CC=C(C=C2)C(C)(C)C)C=C1 | OB(O)[c:16]1[cH:17][cH:18][c:19]([C:20]([CH3:21])([CH3:22])[CH3:23])[cH:24][cH:25]1.Br[c:15]1[cH:14][c:13]2[cH:12][cH:11][n:10]([CH2:9][c:8]3[cH:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:30][cH:29]3)[c:28]2[cH:27][cH:26]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][n:10]2[cH:11][cH:12][c:13]3[... | CC(C)(C)c1ccc(B(O)O)cc1.CC(C)(C)c1ccc(Cn2ccc3cc(Br)ccc32)cc1 | CC(C)(C)c1ccc(Cn2ccc3cc(-c4ccc(C(C)(C)C)cc4)ccc32)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 42e21206f0250bb469664981cf521bd21ce6ff7bf8a8e9271f94397f7d3b79cb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#7;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:7]:[c:6]:1 | null | [] | null | null | null | null | The title compound was prepared from 5-bromo-1-[4-(tert-butyl)benzyl]-1H-indole (Step 1 of Example 34) and 4-(tert-butyl)phenylboronic acid in substantially the same manner, as described in Step 2 of Example 25. The product was obtained as an off-white solid, mp: 167-168° C. Mass spectrum (ESI, [M+H]+) m/z 396. 1 HNMR ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | HBr.B | null | null | null | CC(C)(C)c1ccc(B(O)O)cc1.CC(C)(C)c1ccc(Cn2ccc3cc(Br)ccc32)cc1>>CC(C)(C)c1ccc(Cn2ccc3cc(-c4ccc(C(C)(C)C)cc4)ccc32)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-10349e0697f84ed19a2fddcc69306e49 | CC(C)(C)c1ccc(Cn2ccc3cc(Br)ccc32)cc1.OB(O)c1cccc(Cl)c1>>CC(C)(C)c1ccc(Cn2ccc3cc(-c4cccc(Cl)c4)ccc32)cc1 | BrC=1C=C2C=CN(C2=CC1)CC1=CC=C(C=C1)C(C)(C)C.ClC=1C=C(C=CC1)B(O)O>>C(C)(C)(C)C1=CC=C(CN2C=CC3=CC(=CC=C23)C2=CC(=CC=C2)Cl)C=C1 | Br[c:15]1[cH:14][c:13]2[cH:12][cH:11][n:10]([CH2:9][c:8]3[cH:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:27][cH:26]3)[c:25]2[cH:24][cH:23]1.OB(O)[c:16]1[cH:17][cH:18][cH:19][c:20]([Cl:21])[cH:22]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][n:10]2[cH:11][cH:12][c:13]3[cH:14][c:15](-[c:16]4[cH:17... | CC(C)(C)c1ccc(Cn2ccc3cc(Br)ccc32)cc1.OB(O)c1cccc(Cl)c1 | CC(C)(C)c1ccc(Cn2ccc3cc(-c4cccc(Cl)c4)ccc32)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 42e21206f0250bb469664981cf521bd21ce6ff7bf8a8e9271f94397f7d3b79cb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#7;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:7]:[c:6]:1 | null | [] | null | null | null | null | The title compound was prepared from 5-bromo-1-[4-(tert-butyl)benzyl]-1H-indole (Step 1 of Example 34) and 3-chlorophenylboronic acid in substantially the same manner, as described in Step 2 of Example 25. The product was obtained as an oil. Mass spectrum (ESI, [M+H]+) m/z 374. 1HNMR (400 MHz, DMSO-d6): δ 7.86 (d, 1H, ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | HBr.B | null | null | null | CC(C)(C)c1ccc(Cn2ccc3cc(Br)ccc32)cc1.OB(O)c1cccc(Cl)c1>>CC(C)(C)c1ccc(Cn2ccc3cc(-c4cccc(Cl)c4)ccc32)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d0c5fe00562440babe963c5778202b21 | CC(C)(C)c1ccc(Cn2ccc3cc(Br)ccc32)cc1.OB(O)c1ccc(Cl)cc1>>CC(C)(C)c1ccc(Cn2ccc3cc(-c4ccc(Cl)cc4)ccc32)cc1 | BrC=1C=C2C=CN(C2=CC1)CC1=CC=C(C=C1)C(C)(C)C.ClC1=CC=C(C=C1)B(O)O>>C(C)(C)(C)C1=CC=C(CN2C=CC3=CC(=CC=C23)C2=CC=C(C=C2)Cl)C=C1 | Br[c:15]1[cH:14][c:13]2[cH:12][cH:11][n:10]([CH2:9][c:8]3[cH:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:27][cH:26]3)[c:25]2[cH:24][cH:23]1.OB(O)[c:16]1[cH:17][cH:18][c:19]([Cl:20])[cH:21][cH:22]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][n:10]2[cH:11][cH:12][c:13]3[cH:14][c:15](-[c:16]4[cH:17... | CC(C)(C)c1ccc(Cn2ccc3cc(Br)ccc32)cc1.OB(O)c1ccc(Cl)cc1 | CC(C)(C)c1ccc(Cn2ccc3cc(-c4ccc(Cl)cc4)ccc32)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 42e21206f0250bb469664981cf521bd21ce6ff7bf8a8e9271f94397f7d3b79cb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#7;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:7]:[c:6]:1 | null | [] | null | null | null | null | The title compound was prepared from 5-bromo-1-[4-(tert-butyl)benzyl]-1H-indole (Step 1 of Example 34) and 4-chlorophenylboronic acid in substantially the same manner, as described in Step 2 of Example 25. The product was obtained as an oil. Mass spectrum (ESI, [M+H]+) m/z 374. 1HNMR (400 MHz, DMSO-d6): δ 7.82 (d, 1H, ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | HBr.B | null | null | null | CC(C)(C)c1ccc(Cn2ccc3cc(Br)ccc32)cc1.OB(O)c1ccc(Cl)cc1>>CC(C)(C)c1ccc(Cn2ccc3cc(-c4ccc(Cl)cc4)ccc32)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-341dbc47d56e4f5d976add51f58dcf27 | CC(C)(C)c1ccc(Cn2ccc3cc(Br)ccc32)cc1.Cc1ccccc1B(O)O>>Cc1ccccc1-c1ccc2c(ccn2Cc2ccc(C(C)(C)C)cc2)c1 | BrC=1C=C2C=CN(C2=CC1)CC1=CC=C(C=C1)C(C)(C)C.CC1=C(C=CC=C1)B(O)O>>C(C)(C)(C)C1=CC=C(CN2C=CC3=CC(=CC=C23)C2=C(C=CC=C2)C)C=C1 | Br[c:8]1[cH:9][cH:10][c:11]2[c:12]([cH:13][cH:14][n:15]2[CH2:16][c:17]2[cH:18][cH:19][c:20]([C:21]([CH3:22])([CH3:23])[CH3:24])[cH:25][cH:26]2)[cH:27]1.OB(O)[c:7]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1-[c:8]1[cH:9][cH:10][c:11]2[c:12]([cH:13][cH:14][n:15]2[CH2:16][c:17]2[cH... | CC(C)(C)c1ccc(Cn2ccc3cc(Br)ccc32)cc1.Cc1ccccc1B(O)O | Cc1ccccc1-c1ccc2c(ccn2Cc2ccc(C(C)(C)C)cc2)c1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 42e21206f0250bb469664981cf521bd21ce6ff7bf8a8e9271f94397f7d3b79cb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11](-[C;D1;H3:12]):[c:13]>>[#7;a:5]:[c:4]1:[c:6]:[c:7]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11](-[C;D1;H3:12]):[c:13]):[c:2]:[c:3]:1 | null | [] | null | null | null | null | The title compound was prepared from 5-bromo-1-[4-(tert-butyl)benzyl]-1H-indole (Step 1 of Example 34) and 2-methylphenylboronic acid in substantially the same manner, as described in Step 2 of Example 25. The product was obtained as a brown oil. Mass spectrum (ESI, [M+H]+) m/z 354. 1HNMR (400 MHz, DMSO-d6): δ 7.53 (d,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | HBr.B | null | null | null | CC(C)(C)c1ccc(Cn2ccc3cc(Br)ccc32)cc1.Cc1ccccc1B(O)O>>Cc1ccccc1-c1ccc2c(ccn2Cc2ccc(C(C)(C)C)cc2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8510fa620e884ee7af4c9cee7d7feab0 | Brc1ccc2[nH]ccc2c1.CCC(CC)CBr>>CCC(CC)Cn1ccc2cc(Br)ccc21 | BrCC(CC)CC.BrC=1C=C2C=CNC2=CC1>>BrC=1C=C2C=CN(C2=CC1)CC(CC)CC | [nH:7]1[cH:8][cH:9][c:10]2[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]12.Br[CH2:6][CH:3]([CH2:2][CH3:1])[CH2:4][CH3:5]>>[CH3:1][CH2:2][CH:3]([CH2:4][CH3:5])[CH2:6][n:7]1[cH:8][cH:9][c:10]2[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]12 | Brc1ccc2[nH]ccc2c1.CCC(CC)CBr | CCC(CC)Cn1ccc2cc(Br)ccc21 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 92cc004fc3e2a92f5c9aa0385cdf93f1126e35d5aa485f4f5fe9240c9543c8fe | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc2[nH]ccc2c1 | Br-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4].[c:5]:[c:6]1:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[C:3]-[C:2](-[C:4])-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]:[c:6]:1:[c:5] | 62 | [{"value": 62.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared from 1-bromo-2-ethylbutane (14.14 mL, 101 mmol) and 5-bromoindole (20 g, 101 mmol) in substantially the same manner, as described in Step 1 of Example 25. The product (17.78 g, 62%) was obtained as a colorless oil. Mass spectrum (ESI, [M+H]+) m/z 280. 1 HNMR (400 MHz, DMSO-d6): δ 7.71 (d... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HBr | null | null | null | Brc1ccc2[nH]ccc2c1.CCC(CC)CBr>>CCC(CC)Cn1ccc2cc(Br)ccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b2bd910bae3f4c60a9cb3f3c9838f554 | CCC(CC)Cn1ccc2cc(Br)ccc21.OB(O)c1ccc(OC(F)(F)F)cc1>>CCC(CC)Cn1ccc2cc(-c3ccc(OC(F)(F)F)cc3)ccc21 | BrC=1C=C2C=CN(C2=CC1)CC(CC)CC.FC(OC1=CC=C(C=C1)B(O)O)(F)F>>C(C)C(CN1C=CC2=CC(=CC=C12)C1=CC=C(C=C1)OC(F)(F)F)CC | Br[c:12]1[cH:11][c:10]2[cH:9][cH:8][n:7]([CH2:6][CH:3]([CH2:2][CH3:1])[CH2:4][CH3:5])[c:26]2[cH:25][cH:24]1.OB(O)[c:13]1[cH:14][cH:15][c:16]([O:17][C:18]([F:19])([F:20])[F:21])[cH:22][cH:23]1>>[CH3:1][CH2:2][CH:3]([CH2:4][CH3:5])[CH2:6][n:7]1[cH:8][cH:9][c:10]2[cH:11][c:12](-[c:13]3[cH:14][cH:15][c:16]([O:17][C:18]([F:... | CCC(CC)Cn1ccc2cc(Br)ccc21.OB(O)c1ccc(OC(F)(F)F)cc1 | CCC(CC)Cn1ccc2cc(-c3ccc(OC(F)(F)F)cc3)ccc21 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 42e21206f0250bb469664981cf521bd21ce6ff7bf8a8e9271f94397f7d3b79cb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc3[nH]ccc3c2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#7;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:7]:[c:6]:1 | null | [] | null | null | null | null | The title compound was prepared from 5-bromo-1-(2-ethylbutyl)-1H-indole and 4-(trifluoromethoxy)phenylboronic acid in substantially the same manner, as described in Step 2 of Example 25. The product was obtained as an oil. Mass spectrum (APCI, [M+H]+) m/z 362. 1HNMR (300 MHz, DMSO-d6): δ 7.82 (s, 1H), 7.77 (d, 2H, J=8.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccc2[nH]ccc2c1.c1ccccc1 | HBr.B | null | null | null | CCC(CC)Cn1ccc2cc(Br)ccc21.OB(O)c1ccc(OC(F)(F)F)cc1>>CCC(CC)Cn1ccc2cc(-c3ccc(OC(F)(F)F)cc3)ccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d773cb8dbbcf421e89bf4e4e2f23ad48 | CCOC(=O)c1cc2cc(Br)ccc2[nH]1.Cc1ccc(CBr)cc1>>CCOC(=O)c1cc2cc(Br)ccc2n1Cc1ccc(C)cc1 | BrC=1C=C2C=C(NC2=CC1)C(=O)OCC.CC1=CC=C(CBr)C=C1.CN(C)C=O>>BrC=1C=C2C=C(N(C2=CC1)CC1=CC=C(C=C1)C)C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]2[nH:15]1.Br[CH2:16][c:17]1[cH:18][cH:19][c:20]([CH3:21])[cH:22][cH:23]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]2[n:15]1[CH2:16][c:17]1[cH:18][cH:19][c:20]([CH3:21])[cH:22][cH:... | CCOC(=O)c1cc2cc(Br)ccc2[nH]1.Cc1ccc(CBr)cc1 | CCOC(=O)c1cc2cc(Br)ccc2n1Cc1ccc(C)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 92cc004fc3e2a92f5c9aa0385cdf93f1126e35d5aa485f4f5fe9240c9543c8fe | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cn2ccc3ccccc32)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[c:10]:[c:11]:[c:12](:[c:13]):[nH;D2;+0:14]:1>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[c:10]:[c:11]:[c:12](:[c:13]):[n;H0;D3;+0:14]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The title compound was prepared from ethyl 5-bromo-1H-indole-2-carboxylate and 4-methylbenzyl bromide in substantially the same manner, as described in Step 1 of Example 25. The product was obtained as a semi-solid contained 0.8 mole equivalent DMF. Mass spectrum (ESI, [M+H]+) m/z 372. 1H NMR (400 MHz, DMSO-d6) δ 7.93 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | HBr | null | null | null | CCOC(=O)c1cc2cc(Br)ccc2[nH]1.Cc1ccc(CBr)cc1>>CCOC(=O)c1cc2cc(Br)ccc2n1Cc1ccc(C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a4be1e5594f1414f8eb7b885536308c5 | CCOC(=O)c1cc2cc(Br)ccc2n1Cc1ccc(C)cc1.OB(O)c1ccc(OC(F)(F)F)cc1>>CCOC(=O)c1cc2cc(-c3ccc(OC(F)(F)F)cc3)ccc2n1Cc1ccc(C)cc1 | BrC=1C=C2C=C(N(C2=CC1)CC1=CC=C(C=C1)C)C(=O)OCC.FC(OC1=CC=C(C=C1)B(O)O)(F)F>>CC1=CC=C(CN2C(=CC3=CC(=CC=C23)C2=CC=C(C=C2)OC(F)(F)F)C(=O)OCC)C=C1 | Br[c:10]1[cH:9][c:8]2[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[n:25]([CH2:26][c:27]3[cH:28][cH:29][c:30]([CH3:31])[cH:32][cH:33]3)[c:24]2[cH:23][cH:22]1.OB(O)[c:11]1[cH:12][cH:13][c:14]([O:15][C:16]([F:17])([F:18])[F:19])[cH:20][cH:21]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10](-[c:11]3[cH:12]... | CCOC(=O)c1cc2cc(Br)ccc2n1Cc1ccc(C)cc1.OB(O)c1ccc(OC(F)(F)F)cc1 | CCOC(=O)c1cc2cc(-c3ccc(OC(F)(F)F)cc3)ccc2n1Cc1ccc(C)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 42e21206f0250bb469664981cf521bd21ce6ff7bf8a8e9271f94397f7d3b79cb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#7;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:7]:[c:6]:1 | null | [] | null | null | null | null | The title compound was prepared from ethyl 5-bromo-1-(4-methylbenzyl)-1H-indole-2-carboxylate and 4-(trifluoromethoxy)phenylboronic acid in substantially the same manner, as described in Step 2 of Example 25. The product was obtained as an off-white solid, m.p. 77-78° C. Mass spectrum (ESI, [M+H]+) m/z 454. 1H NMR (400... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccc2[nH]ccc2c1.c1ccccc1.c1ccccc1 | HBr.B | null | null | null | CCOC(=O)c1cc2cc(Br)ccc2n1Cc1ccc(C)cc1.OB(O)c1ccc(OC(F)(F)F)cc1>>CCOC(=O)c1cc2cc(-c3ccc(OC(F)(F)F)cc3)ccc2n1Cc1ccc(C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-71d391290e9f492c834108966b3a84d2 | CCOC(=O)c1cc2cc(-c3ccc(OC(F)(F)F)cc3)ccc2n1Cc1ccc(C)cc1>>Cc1ccc(Cn2c(CO)cc3cc(-c4ccc(OC(F)(F)F)cc4)ccc32)cc1 | [H-].[Al+3].[Li+].[H-].[H-].[H-].CC1=CC=C(CN2C(=CC3=CC(=CC=C23)C2=CC=C(C=C2)OC(F)(F)F)C(=O)OCC)C=C1>>CC1=CC=C(CN2C(=CC3=CC(=CC=C23)C2=CC=C(C=C2)OC(F)(F)F)CO)C=C1 | CCO[C:9]([c:8]1[n:7]([CH2:6][c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:30][cH:29]2)[c:28]2[c:12]([cH:11]1)[cH:13][c:14](-[c:15]1[cH:16][cH:17][c:18]([O:19][C:20]([F:21])([F:22])[F:23])[cH:24][cH:25]1)[cH:26][cH:27]2)=[O:10]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][n:7]2[c:8]([CH2:9][OH:10])[cH:11][c:12]3[cH:13][c:14](-[c:15]4[... | CCOC(=O)c1cc2cc(-c3ccc(OC(F)(F)F)cc3)ccc2n1Cc1ccc(C)cc1 | Cc1ccc(Cn2c(CO)cc3cc(-c4ccc(OC(F)(F)F)cc4)ccc32)cc1 | null | null | C(C)OCC | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[#7;a:5](-[C:6]):[c:7]>>[C:6]-[#7;a:5](:[c:7]):[c:3](-[CH2;D2;+0:1]-[OH;D1;+0:2]):[c:4] | 86.2 | [{"value": 86.0, "product": "CC1=CC=C(CN2C(=CC3=CC(=CC=C23)C2=CC=C(C=C2)OC(F)(F)F)CO)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.2, "product": "CC1=CC=C(CN2C(=CC3=CC(=CC=C23)C2=CC=C(C=C2)OC(F)(F)F)CO)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | Lithium aluminum hydride (0.244 g, 6.1 mmol) was added portionwise to a stirring solution of ethyl 1-(4-methylbenzyl)-5-[4-(trifluoromethoxy)phenyl]-1H-indole-2-carboxylate (2.0 g, 4.4 mmol) in ethyl ether (17 mL) at 0° C. under a nitrogen atmosphere over a period of 5 minutes. The mixture was then warmed up to room te... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | HO- | C(C)OCC | null | 5 | CCOC(=O)c1cc2cc(-c3ccc(OC(F)(F)F)cc3)ccc2n1Cc1ccc(C)cc1>C(C)OCC>Cc1ccc(Cn2c(CO)cc3cc(-c4ccc(OC(F)(F)F)cc4)ccc32)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-80d80c1c55fb4578bdb49d8fb3a9d1a5 | CC(=O)Cl.Cc1ccc(Cn2c(CO)cc3cc(-c4ccc(OC(F)(F)F)cc4)ccc32)cc1>>CC(=O)OCc1cc2cc(-c3ccc(OC(F)(F)F)cc3)ccc2n1Cc1ccc(C)cc1 | C(C)(=O)Cl.CC1=CC=C(CN2C(=CC3=CC(=CC=C23)C2=CC=C(C=C2)OC(F)(F)F)CO)C=C1.C(C)(C)N(C(C)C)CC>>C(C)(=O)OCC=1N(C2=CC=C(C=C2C1)C1=CC=C(C=C1)OC(F)(F)F)CC1=CC=C(C=C1)C | Cl[C:2]([CH3:1])=[O:3].[OH:4][CH2:5][c:6]1[cH:7][c:8]2[cH:9][c:10](-[c:11]3[cH:12][cH:13][c:14]([O:15][C:16]([F:17])([F:18])[F:19])[cH:20][cH:21]3)[cH:22][cH:23][c:24]2[n:25]1[CH2:26][c:27]1[cH:28][cH:29][c:30]([CH3:31])[cH:32][cH:33]1>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][c:6]1[cH:7][c:8]2[cH:9][c:10](-[c:11]3[cH:12][cH:1... | CC(=O)Cl.Cc1ccc(Cn2c(CO)cc3cc(-c4ccc(OC(F)(F)F)cc4)ccc32)cc1 | CC(=O)OCc1cc2cc(-c3ccc(OC(F)(F)F)cc3)ccc2n1Cc1ccc(C)cc1 | null | null | C(Cl)Cl | Acylation | Schotten-Baumann to ester | 6cefe709828c5bd4655f254e75d5dff9e8876e192e7dd47256c1bc0067bc5291 | d8a7643b81ed07a6f633aa99465180dfa0565e61ae25aef36338ebb9837c9cef | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#7;a:4]:[c:5]-[C:6]-[OH;D1;+0:7]>>[#7;a:4]:[c:5]-[C:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | 99.9 | [{"value": 99.6, "product": "C(C)(=O)OCC=1N(C2=CC=C(C=C2C1)C1=CC=C(C=C1)OC(F)(F)F)CC1=CC=C(C=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.9, "product": "C(C)(=O)OCC=1N(C2=CC=C(C=C2C1)C1=CC=C(C=C1)OC(F)(F)F)CC1=CC=C(C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Acetyl chloride (0.222 mL, 3.08 mmol) was added to a stirring solution of {1-(4-methylbenzyl)-5-[4-(trifluoromethoxy)phenyl]-1H-indol-2-yl}methanol (0.507 g, 1.23 mmol) and N,N-diisopropylethylamine (0.547 mL, 3.08 mmol) in methylene chloride (8 mL) at 0° C. under a nitrogen atmosphere over a period of 5 minutes. After... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary alcohol | Ester | null | null | c1ccc2[nH]ccc2c1.c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | null | 8 | CC(=O)Cl.Cc1ccc(Cn2c(CO)cc3cc(-c4ccc(OC(F)(F)F)cc4)ccc32)cc1>C(Cl)Cl>CC(=O)OCc1cc2cc(-c3ccc(OC(F)(F)F)cc3)ccc2n1Cc1ccc(C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e835db01a31448aca69cfb8e455ba8aa | BrCc1ccccc1.CCOC(=O)c1cc2cc(Br)ccc2[nH]1>>CCOC(=O)c1cc2cc(Br)ccc2n1Cc1ccccc1 | BrC=1C=C2C=C(NC2=CC1)C(=O)OCC.C(C1=CC=CC=C1)Br>>BrC=1C=C2C=C(N(C2=CC1)CC1=CC=CC=C1)C(=O)OCC | Br[CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]2[nH:15]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]2[n:15]1[CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | BrCc1ccccc1.CCOC(=O)c1cc2cc(Br)ccc2[nH]1 | CCOC(=O)c1cc2cc(Br)ccc2n1Cc1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 92cc004fc3e2a92f5c9aa0385cdf93f1126e35d5aa485f4f5fe9240c9543c8fe | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cn2ccc3ccccc32)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[c:10]:[c:11]:[c:12](:[c:13]):[nH;D2;+0:14]:1>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[c:10]:[c:11]:[c:12](:[c:13]):[n;H0;D3;+0:14]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The title compound was prepared from ethyl 5-bromo-1H-indole-2-carboxylate and benzyl bromide in substantially the same manner, as described in Step 1 of Example 25. The product was obtained as a light yellow solid. Mass spectrum (ESI, [M+H]+) m/z 358.1 HNMR (300 MHz, DMSO-d6): δ 7.94 (s, 1H), 7.55 (d, 1H, J=9.01 Hz), ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | HBr | null | null | null | BrCc1ccccc1.CCOC(=O)c1cc2cc(Br)ccc2[nH]1>>CCOC(=O)c1cc2cc(Br)ccc2n1Cc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5495bbecea264db89a9b958f4af142e1 | CCOC(=O)c1cc2cc(Br)ccc2n1Cc1ccccc1.OB(O)c1ccc(OC(F)(F)F)cc1>>CCOC(=O)c1cc2cc(-c3ccc(OC(F)(F)F)cc3)ccc2n1Cc1ccccc1 | BrC=1C=C2C=C(N(C2=CC1)CC1=CC=CC=C1)C(=O)OCC.FC(OC1=CC=C(C=C1)B(O)O)(F)F>>C(C1=CC=CC=C1)N1C(=CC2=CC(=CC=C12)C1=CC=C(C=C1)OC(F)(F)F)C(=O)OCC | Br[c:10]1[cH:9][c:8]2[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[n:25]([CH2:26][c:27]3[cH:28][cH:29][cH:30][cH:31][cH:32]3)[c:24]2[cH:23][cH:22]1.OB(O)[c:11]1[cH:12][cH:13][c:14]([O:15][C:16]([F:17])([F:18])[F:19])[cH:20][cH:21]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][c:10](-[c:11]3[cH:12][cH:13][c... | CCOC(=O)c1cc2cc(Br)ccc2n1Cc1ccccc1.OB(O)c1ccc(OC(F)(F)F)cc1 | CCOC(=O)c1cc2cc(-c3ccc(OC(F)(F)F)cc3)ccc2n1Cc1ccccc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 42e21206f0250bb469664981cf521bd21ce6ff7bf8a8e9271f94397f7d3b79cb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#7;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:7]:[c:6]:1 | null | [] | null | null | null | null | The title compound was prepared from ethyl 5-bromo-1-benzyl-1H-indole-2-carboxylate and 4-(trifluoromethoxy)phenylboronic acid in substantially the same manner, as described in Step 2 of Example 25. The product was obtained as an oil. Mass spectrum (ESI, [M+H]+) m/z 440. 1HNMR (400 MHz, DMSO-d6): δ 8.01 (s, 1H), 7.79 (... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccc2[nH]ccc2c1.c1ccccc1.c1ccccc1 | HBr.B | null | null | null | CCOC(=O)c1cc2cc(Br)ccc2n1Cc1ccccc1.OB(O)c1ccc(OC(F)(F)F)cc1>>CCOC(=O)c1cc2cc(-c3ccc(OC(F)(F)F)cc3)ccc2n1Cc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-94f437dd366c48669ce5e425d84773b9 | CCOC(=O)c1cc2cc(-c3ccc(OC(F)(F)F)cc3)ccc2n1Cc1ccccc1>>OCc1cc2cc(-c3ccc(OC(F)(F)F)cc3)ccc2n1Cc1ccccc1 | C(C1=CC=CC=C1)N1C(=CC2=CC(=CC=C12)C1=CC=C(C=C1)OC(F)(F)F)C(=O)OCC.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>C(C1=CC=CC=C1)N1C(=CC2=CC(=CC=C12)C1=CC=C(C=C1)OC(F)(F)F)CO | CCO[C:2](=[O:1])[c:3]1[cH:4][c:5]2[cH:6][c:7](-[c:8]3[cH:9][cH:10][c:11]([O:12][C:13]([F:14])([F:15])[F:16])[cH:17][cH:18]3)[cH:19][cH:20][c:21]2[n:22]1[CH2:23][c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1>>[OH:1][CH2:2][c:3]1[cH:4][c:5]2[cH:6][c:7](-[c:8]3[cH:9][cH:10][c:11]([O:12][C:13]([F:14])([F:15])[F:16])[cH:17][cH... | CCOC(=O)c1cc2cc(-c3ccc(OC(F)(F)F)cc3)ccc2n1Cc1ccccc1 | OCc1cc2cc(-c3ccc(OC(F)(F)F)cc3)ccc2n1Cc1ccccc1 | null | null | null | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[#7;a:5](-[C:6]):[c:7]>>[C:6]-[#7;a:5](:[c:7]):[c:3](-[CH2;D2;+0:1]-[OH;D1;+0:2]):[c:4] | null | [] | null | null | null | null | The title compound was prepared from Ethyl 1-benzyl-5-[4-(trifluoromethoxy)phenyl]-1H-indole-2-carboxylate (Step 2 of Example 25) and lithium aluminum hydride in substantially the same manner, as described in Step 1 of Example 21. The product was obtained as a white solid, mp: 108-109° C. Mass spectrum (ESI, [M+H]+) m/... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccc2[nH]ccc2c1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CCOC(=O)c1cc2cc(-c3ccc(OC(F)(F)F)cc3)ccc2n1Cc1ccccc1>>OCc1cc2cc(-c3ccc(OC(F)(F)F)cc3)ccc2n1Cc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7510a371f1a04711bd90311ce57847a5 | Brc1ccc2[nH]ccc2c1.OB(O)c1cccc(Cl)c1>>Clc1cccc(-c2ccc3[nH]ccc3c2)c1 | C(=O)([O-])[O-].[Na+].[Na+].BrC=1C=C2C=CNC2=CC1.ClC=1C=C(C=CC1)B(O)O.CCO.O>>ClC=1C=C(C=CC1)C=1C=C2C=CNC2=CC1 | Br[c:7]1[cH:8][cH:9][c:10]2[nH:11][cH:12][cH:13][c:14]2[cH:15]1.OB(O)[c:6]1[cH:5][cH:4][cH:3][c:2]([Cl:1])[cH:16]1>>[Cl:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]3[nH:11][cH:12][cH:13][c:14]3[cH:15]2)[cH:16]1 | Brc1ccc2[nH]ccc2c1.OB(O)c1cccc(Cl)c1 | Clc1cccc(-c2ccc3[nH]ccc3c2)c1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O | C-C Coupling | Suzuki coupling with boronic acids | 42e21206f0250bb469664981cf521bd21ce6ff7bf8a8e9271f94397f7d3b79cb | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc3[nH]ccc3c2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[#7;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:7]:[c:6]:1 | 100.5 | [{"value": 100.5, "product": "ClC=1C=C(C=CC1)C=1C=C2C=CNC2=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred slurry of 4.23 g (40 mmol) Na2CO3, 1.84 g (9.4 mmol) 5-bromoindole, 1.88 g (10 mmol) 3-chlorophenylboronic acid, and 0.29 g (0.25 mmol) Pd(PPh3)4 in 50 mL 1:1 EtOH-water was heated to reflux for 2.5 hours. The reaction mixture was allowed to cool and was then poured into 400 mL water and extracted with EtOAc.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O | null | null | Brc1ccc2[nH]ccc2c1.OB(O)c1cccc(Cl)c1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O>Clc1cccc(-c2ccc3[nH]ccc3c2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-947dac7a446e4ebf97672fc1bae21095 | Clc1cccc(-c2ccc3[nH]ccc3c2)c1.O=S(=O)(Cl)c1ccccc1>>O=S(=O)(c1ccccc1)n1ccc2cc(-c3cccc(Cl)c3)ccc21 | O.C1(=CC=CC=C1)S(=O)(=O)Cl.[H-].[Na+].ClC=1C=C(C=CC1)C=1C=C2C=CNC2=CC1>>C1(=CC=CC=C1)S(=O)(=O)N1C=CC2=CC(=CC=C12)C1=CC(=CC=C1)Cl | [nH:10]1[cH:11][cH:12][c:13]2[cH:14][c:15](-[c:16]3[cH:17][cH:18][cH:19][c:20]([Cl:21])[cH:22]3)[cH:23][cH:24][c:25]12.Cl[S:2](=[O:1])(=[O:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1>>[O:1]=[S:2](=[O:3])([c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[n:10]1[cH:11][cH:12][c:13]2[cH:14][c:15](-[c:16]3[cH:17][cH:18][cH:19][c:20]([Cl... | Clc1cccc(-c2ccc3[nH]ccc3c2)c1.O=S(=O)(Cl)c1ccccc1 | O=S(=O)(c1ccccc1)n1ccc2cc(-c3cccc(Cl)c3)ccc21 | null | null | C1CCOC1 | Miscellaneous | OtherReaction | b2b0fa9a79049e6f5621e837ed4836919c6cf82dece4f60c93a30b12a3dbd400 | 5f0d826ff827e7d94d07bc9ee74d0a88c79bcf75bb024f05043486e1cbe294bd | O=S(=O)(c1ccccc1)n1ccc2cc(-c3ccccc3)ccc21 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[c:7]:[c:8]1:[c:9]:[c:10]:[c:11]:[nH;D2;+0:12]:1>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[c:4](:[c:5]):[c:6])-[n;H0;D3;+0:12]1:[c:11]:[c:10]:[c:9]:[c:8]:1:[c:7] | 42.2 | [{"value": 42.2, "product": "C1(=CC=CC=C1)S(=O)(=O)N1C=CC2=CC(=CC=C12)C1=CC(=CC=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a stirred slurry of 0.61 g (12.7 mmol), 50% dispersion of NaH in mineral oil, in 36 mL anhydrous THF was added 2.15 g crude 5-(3-chlorophenyl)indole (Step 1 of Example 45). The solution was allowed to stir at room temperature 15 min upon which time 1.2 mL (9.4 mmol) phenylsulfonyl chloride was added dropwise. The so... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | HCl | C1CCOC1 | null | 8 | Clc1cccc(-c2ccc3[nH]ccc3c2)c1.O=S(=O)(Cl)c1ccccc1>C1CCOC1>O=S(=O)(c1ccccc1)n1ccc2cc(-c3cccc(Cl)c3)ccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fea3f796f3cd4a8cb293301673c4d261 | O=S(=O)(c1ccccc1)n1ccc2cc(-c3cccc(Cl)c3)ccc21.OC1CCCC1>>Clc1cccc(-c2ccc3c(ccn3C3CCCC3)c2)c1 | CC(C)(C)[O-].[K+].C1(CCCC1)O.C1(=CC=CC=C1)S(=O)(=O)N1C=CC2=CC(=CC=C12)C1=CC(=CC=C1)Cl>>ClC=1C=C(C=CC1)C=1C=C2C=CN(C2=CC1)C1CCCC1 | O=S(=O)(c1ccccc1)[n:14]1[c:10]2[cH:9][cH:8][c:7](-[c:6]3[cH:5][cH:4][cH:3][c:2]([Cl:1])[cH:21]3)[cH:20][c:11]2[cH:12][cH:13]1.O[CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19]1>>[Cl:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]3[c:11]([cH:12][cH:13][n:14]3[CH:15]3[CH2:16][CH2:17][CH2:18][CH2:19]3)[cH:20]2)[cH:21]1 | O=S(=O)(c1ccccc1)n1ccc2cc(-c3cccc(Cl)c3)ccc21.OC1CCCC1 | Clc1cccc(-c2ccc3c(ccn3C3CCCC3)c2)c1 | null | null | [Cl-].[Na+].O.C1(=CC=CC=C1)C.C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 6c63ad0e43571b718b9bb9b22f2e8ed127a9af6ff3894c292116211cd0b45762 | 7e4920259a1416b2ad82882dcdd5ff78bfba80ea8d17566c27d0d8f23a71cd94 | c1ccc(-c2ccc3c(ccn3C3CCCC3)c2)cc1 | O-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1.O=S(=O)(-[n;H0;D3;+0:6]1:[c:7]:[c:8]:[c:9]:[c:10]:1:[c:11])-c1:c:c:c:c:c:1>>[c:11]:[c:10]1:[c:9]:[c:8]:[c:7]:[n;H0;D3;+0:6]:1-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1 | null | [] | 150 | CELSIUS | null | null | A 5 mL conical glass microwave reaction vessel with stir bar, sealed with a septum and swept with nitrogen, was charged with a solution of 0.08 g (0.22 mmol) 1-(benzenesulfonyl-5-(3-chlorophenyl)-1H-indole in 1.2 mL anhydrous toluene. 32 μL (0.33 mmol) cyclopentanol was added with stirring, followed by 0.3 mL 1.0 M sol... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | null | c1ccccc1.c1ccc2[nH]ccc2c1.C1CCCC1 | c1ccc2[nH]ccc2c1.C1CCCC1 | c1ccccc1.c1ccc2[nH]ccc2c1.C1CCCC1 | HO- | [Cl-].[Na+].O.C1(=CC=CC=C1)C.C1CCOC1 | 150 | null | O=S(=O)(c1ccccc1)n1ccc2cc(-c3cccc(Cl)c3)ccc21.OC1CCCC1>[Cl-].[Na+].O.C1(=CC=CC=C1)C.C1CCOC1>Clc1cccc(-c2ccc3c(ccn3C3CCCC3)c2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-611af92e7dae4267bc90a76f838d59bc | Clc1cccc(-c2ccc3c(ccn3C3CCCC3)c2)c1.O=C(Cl)C(=O)Cl>>O=C(O)C(=O)c1cn(C2CCCC2)c2ccc(-c3cccc(Cl)c3)cc12 | ClC=1C=C(C=CC1)C=1C=C2C=CN(C2=CC1)C1CCCC1.C1CCOC1.C(=O)(C(=O)Cl)Cl>>ClC=1C=C(C=CC1)C=1C=C2C(=CN(C2=CC1)C1CCCC1)C(C(=O)O)=O | [cH:6]1[cH:7][n:8]([CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13]2)[c:14]2[cH:15][cH:16][c:17](-[c:18]3[cH:19][cH:20][cH:21][c:22]([Cl:23])[cH:24]3)[cH:25][c:26]12.Cl[C:2](=[O:1])[C:4](Cl)=[O:5]>>[O:1]=[C:2]([OH:3])[C:4](=[O:5])[c:6]1[cH:7][n:8]([CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13]2)[c:14]2[cH:15][cH:16][c:17](-[c:18]3[cH:... | Clc1cccc(-c2ccc3c(ccn3C3CCCC3)c2)c1.O=C(Cl)C(=O)Cl | O=C(O)C(=O)c1cn(C2CCCC2)c2ccc(-c3cccc(Cl)c3)cc12 | null | null | null | Acylation | OtherReaction | 9d127b05b36fe9fe6fc80547d3614a823e90d1399390b2ba6617beb8202d8432 | 6b048b617f07704989b0d7eff26dc61c44694ea4e42b339d6d7680e8458e5255 | c1ccc(-c2ccc3c(ccn3C3CCCC3)c2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](-Cl)=[O;D1;H0:4].[C:5]-[#7;a:6]1:[c:7]:[cH;D2;+0:8]:[c:9](:[c:10]):[c:11]:1:[c:12]>>[C:5]-[#7;a:6]1:[c:7]:[c;H0;D3;+0:8](-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;D1;H1:13]):[c:9](:[c:10]):[c:11]:1:[c:12] | null | [] | null | null | null | null | The product from Step 3 of Example 45 was dissolved in 0.5 ml anhydrous THF and 50 μL (COCl)2 was added. The solution was mixed at room temperature overnight with orbital shaking. An aliquot removed for LC analysis indicated that the reaction was complete. The solution was added to 1 mL aqueous NaHCO3 and the vial was ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide | Carboxylic acid.Ketone | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | C1CCCC1.c1ccc2[nH]ccc2c1.c1ccccc1 | Other | null | null | null | Clc1cccc(-c2ccc3c(ccn3C3CCCC3)c2)c1.O=C(Cl)C(=O)Cl>>O=C(O)C(=O)c1cn(C2CCCC2)c2ccc(-c3cccc(Cl)c3)cc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-93b4e1e9211d4d059eda2a8ed161a707 | Cn1ccc2ccc(-c3ccc(C(F)(F)F)cc3)cc21.O=C=O>>Cn1cc(C(=O)O)c2ccc(-c3ccc(C(F)(F)F)cc3)cc21 | C(=O)=O.CN1C=CC2=CC=C(C=C12)C1=CC=C(C=C1)C(F)(F)F.C(CCC)[Li]>>CN1C=C(C2=CC=C(C=C12)C1=CC=C(C=C1)C(F)(F)F)C(=O)O | [CH3:1][n:2]1[cH:3][cH:4][c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][c:15]([C:16]([F:17])([F:18])[F:19])[cH:20][cH:21]3)[cH:22][c:23]12.[C:5](=[O:6])=[O:7]>>[CH3:1][n:2]1[cH:3][c:4]([C:5](=[O:6])[OH:7])[c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][c:15]([C:16]([F:17])([F:18])[F:19])[cH:20][cH:21]3)[cH:22][c:23]... | Cn1ccc2ccc(-c3ccc(C(F)(F)F)cc3)cc21.O=C=O | Cn1cc(C(=O)O)c2ccc(-c3ccc(C(F)(F)F)cc3)cc21 | null | null | C1CCOC1 | Acylation | OtherReaction | df7c74f2ca61ca5e8f920d60e8c90613bc2bb44892a91d0192b927d32b27b4ca | f2fa2063dd26da08ea200eb6cbb3037b91013a82352a2b60120e98f9e54cbd88 | c1ccc(-c2ccc3cc[nH]c3c2)cc1 | [C;D1;H3:1]-[#7;a:2]1:[c:3]:[cH;D2;+0:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[O;D1;H0:9]=[C;H0;D2;+0:10]=[O;H0;D1;+0:11]>>[C;D1;H3:1]-[#7;a:2]1:[c:3]:[c;H0;D3;+0:4](-[C;H0;D3;+0:10](=[O;D1;H0:9])-[OH;D1;+0:11]):[c:5](:[c:6]):[c:7]:1:[c:8] | 19 | [{"value": 19.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 30 | MINUTE | To a solution of 1-methyl-6-(4-trifluoromethyl-phenyl)-1H-indole (0.483 g, 1.75 mmol) in dry THF (10 mL) at −78° C. was added n-butyllithium (0.84 mL, 2.1 mmol). The reaction mixture was stirred under nitrogen at −78° C. for 30 minutes then at −50 to −40° C. for 30 minutes. It reaction temperature was cooled to −78° C.... | 10.6084/m9.figshare.5104873.v1 | null | Carbon dioxide | Carboxylic acid | c1ccc2cc[nH]c2c1 | c1ccc2cc[nH]c2c1 | c1ccc2cc[nH]c2c1.c1ccccc1 | null | C1CCOC1 | -78 | 0.5 | Cn1ccc2ccc(-c3ccc(C(F)(F)F)cc3)cc21.O=C=O>C1CCOC1>Cn1cc(C(=O)O)c2ccc(-c3ccc(C(F)(F)F)cc3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5ec2f35bd10448598046f7b4147eeb64 | Cn1ccc2ccc(-c3ccc(C(C)(C)C)cc3)cc21.O=C=O>>Cn1cc(C(=O)O)c2ccc(-c3ccc(C(C)(C)C)cc3)cc21 | C(C)(C)(C)C1=CC=C(C=C1)C1=CC=C2C=CN(C2=C1)C.C(CCC)[Li].C(=O)=O>>C(C)(C)(C)C1=CC=C(C=C1)C1=CC=C2C(=CN(C2=C1)C)C(=O)O | [CH3:1][n:2]1[cH:3][cH:4][c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][c:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][cH:21]3)[cH:22][c:23]12.[C:5](=[O:6])=[O:7]>>[CH3:1][n:2]1[cH:3][c:4]([C:5](=[O:6])[OH:7])[c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][c:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][cH:21]3)[... | Cn1ccc2ccc(-c3ccc(C(C)(C)C)cc3)cc21.O=C=O | Cn1cc(C(=O)O)c2ccc(-c3ccc(C(C)(C)C)cc3)cc21 | null | null | C1CCOC1 | Acylation | OtherReaction | df7c74f2ca61ca5e8f920d60e8c90613bc2bb44892a91d0192b927d32b27b4ca | f2fa2063dd26da08ea200eb6cbb3037b91013a82352a2b60120e98f9e54cbd88 | c1ccc(-c2ccc3cc[nH]c3c2)cc1 | [C;D1;H3:1]-[#7;a:2]1:[c:3]:[cH;D2;+0:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[O;D1;H0:9]=[C;H0;D2;+0:10]=[O;H0;D1;+0:11]>>[C;D1;H3:1]-[#7;a:2]1:[c:3]:[c;H0;D3;+0:4](-[C;H0;D3;+0:10](=[O;D1;H0:9])-[OH;D1;+0:11]):[c:5](:[c:6]):[c:7]:1:[c:8] | 10.7 | [{"value": 10.7, "product": "C(C)(C)(C)C1=CC=C(C=C1)C1=CC=C2C(=CN(C2=C1)C)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 10.7, "product": "C(C)(C)(C)C1=CC=C(C=C1)C1=CC=C2C(=CN(C2=C1)C)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 6-(4-tert-Butyl-phenyl)-1-methyl-1H-indole-3-carboxylic acid was prepared from 6-(4-tert-butyl-phenyl)-1-methyl-1H-indole (0.541 g, 2.05 mmol), n-butyllithium (0.98 mL, 2.5 mmol), crushed dry ice (3 g, 70 mmol) in dry THF (10 mL) according to the procedure described in Example 60. Purification by flash chromatography u... | 10.6084/m9.figshare.5104873.v1 | null | Carbon dioxide | Carboxylic acid | c1ccc2cc[nH]c2c1 | c1ccc2cc[nH]c2c1 | c1ccc2cc[nH]c2c1.c1ccccc1 | null | C1CCOC1 | null | null | Cn1ccc2ccc(-c3ccc(C(C)(C)C)cc3)cc21.O=C=O>C1CCOC1>Cn1cc(C(=O)O)c2ccc(-c3ccc(C(C)(C)C)cc3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f2c14f61129d4978b91d83e4b3022efc | Fc1ccc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc1Cl.O=C=O>>O=C(O)c1cn(Cc2ccccc2)c2ccc(-c3ccc(F)c(Cl)c3)cc12 | C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)C1=CC(=C(C=C1)F)Cl.C(CCC)[Li].C(=O)=O>>C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)C1=CC(=C(C=C1)F)Cl)C(=O)O | [cH:4]1[cH:5][n:6]([CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[c:14]2[cH:15][cH:16][c:17](-[c:18]3[cH:19][cH:20][c:21]([F:22])[c:23]([Cl:24])[cH:25]3)[cH:26][c:27]12.[O:1]=[C:2]=[O:3]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][n:6]([CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[c:14]2[cH:15][cH:16][c:17](-[c:18]3[cH:19]... | Fc1ccc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc1Cl.O=C=O | O=C(O)c1cn(Cc2ccccc2)c2ccc(-c3ccc(F)c(Cl)c3)cc12 | null | null | C1CCOC1 | Acylation | OtherReaction | 73b6b50aa9b03f0c498dcfa29ca94d47bf015c87854538026c3079cdf775e6ac | f2fa2063dd26da08ea200eb6cbb3037b91013a82352a2b60120e98f9e54cbd88 | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | [C:1]-[#7;a:2]1:[c:3]:[cH;D2;+0:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[O;D1;H0:9]=[C;H0;D2;+0:10]=[O;H0;D1;+0:11]>>[C:1]-[#7;a:2]1:[c:3]:[c;H0;D3;+0:4](-[C;H0;D3;+0:10](=[O;D1;H0:9])-[OH;D1;+0:11]):[c:5](:[c:6]):[c:7]:1:[c:8] | 32 | [{"value": 32.0, "product": "C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)C1=CC(=C(C=C1)F)Cl)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.0, "product": "C(C1=CC=CC=C1)N1C=C(C2=CC(=CC=C12)C1=CC(=C(C=C1)F)Cl)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-Benzyl-5-(3-chloro-4-fluoro-phenyl)-1H-indole-3-carboxylic acid was prepared from 1-benzyl-5-(3-chloro-4-fluorophenyl)-1H-indole (17.99 g, 53.6 mmol), n-butyllithium (26 mL, 65 mmol), crushed dry ice (20 g, 450 mmol) in dry THF (180 mL) according to the procedure described in Example 60. Purification by HPLC using 85... | 10.6084/m9.figshare.5104873.v1 | null | Carbon dioxide | Carboxylic acid | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | null | C1CCOC1 | null | null | Fc1ccc(-c2ccc3c(ccn3Cc3ccccc3)c2)cc1Cl.O=C=O>C1CCOC1>O=C(O)c1cn(Cc2ccccc2)c2ccc(-c3ccc(F)c(Cl)c3)cc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9299ce90a014458f90c0ed8e50ecd9e9 | Brc1ccc2[nH]ccc2c1.C=O.CNC>>CN(C)Cc1c[nH]c2ccc(Br)cc12 | CNC.C=O.BrC=1C=C2C=CNC2=CC1>>BrC=1C=C2C(=CNC2=CC1)CN(C)C | [cH:5]1[cH:6][nH:7][c:8]2[cH:9][cH:10][c:11]([Br:12])[cH:13][c:14]12.O=[CH2:4].[CH3:1][NH:2][CH3:3]>>[CH3:1][N:2]([CH3:3])[CH2:4][c:5]1[cH:6][nH:7][c:8]2[cH:9][cH:10][c:11]([Br:12])[cH:13][c:14]12 | Brc1ccc2[nH]ccc2c1.C=O.CNC | CN(C)Cc1c[nH]c2ccc(Br)cc12 | null | null | C(C)(=O)O | Heteroatom Alkylation and Arylation | OtherReaction | 14f2bfa3d907d463fab4dfc74293051dd668edd77fb6e0a45ccb47b35b91e990 | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | c1ccc2[nH]ccc2c1 | O=[CH2;D1;+0:1].[C;D1;H3:2]-[NH;D2;+0:3]-[C;D1;H3:4].[c:5]:[c:6]1:[cH;D2;+0:7]:[c:8]:[#7;a:9]:[c:10]:1:[c:11]>>[C;D1;H3:2]-[N;H0;D3;+0:3](-[C;D1;H3:4])-[CH2;D2;+0:1]-[c;H0;D3;+0:7]1:[c:8]:[#7;a:9]:[c:10](:[c:11]):[c:6]:1:[c:5] | 88.7 | [{"value": 88.7, "product": "BrC=1C=C2C(=CNC2=CC1)CN(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 21 | HOUR | To a mixture of 40% aqueous dimethylamine (5.95 g, 52.8 mmol), 37% aqueous formaldehyde (4.21 g, 51.9 mmol) and acetic acid (7 mL) was added 5-bromo-1H-indole (9.79 g, 49.9 mmol). The reaction mixture was stirred for 21 hours at room temperature and poured into a 2.5 N sodium hydroxide/ice mixture (200 mL). This was ex... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HO- | C(C)(=O)O | null | 21 | Brc1ccc2[nH]ccc2c1.C=O.CNC>C(C)(=O)O>CN(C)Cc1c[nH]c2ccc(Br)cc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-76d2e0726b0d492a92d963f3bba1cef9 | CN(C)Cc1c[nH]c2ccc(Br)cc12>>N#CCc1c[nH]c2ccc(Br)cc12 | BrC=1C=C2C(=CNC2=CC1)CN(C)C.C[Si](C)(C)C#N.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC.IC>>BrC=1C=C2C(=CNC2=CC1)CC#N | CN(C)[CH2:3][c:4]1[cH:5][nH:6][c:7]2[cH:8][cH:9][c:10]([Br:11])[cH:12][c:13]12>>[N:1]#[C:2][CH2:3][c:4]1[cH:5][nH:6][c:7]2[cH:8][cH:9][c:10]([Br:11])[cH:12][c:13]12 | CN(C)Cc1c[nH]c2ccc(Br)cc12 | N#CCc1c[nH]c2ccc(Br)cc12 | null | null | C1=CC=CC=C1.O.C1CCOC1 | Miscellaneous | OtherReaction | eeb390a765a14be516804ac95cf046d9e14d2a33610d749ac9b0df57ebee4fc2 | dbf463487c354e590d1a121365b90aebc9d0a0d1f40f1a429596c4c6b1e08f52 | c1ccc2[nH]ccc2c1 | C-N(-C)-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:1>>[N;D1;H0:7]#[C:8]-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:1 | 51.1 | [{"value": 51.0, "product": "BrC=1C=C2C(=CNC2=CC1)CC#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.1, "product": "BrC=1C=C2C(=CNC2=CC1)CC#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To an ice cooled suspension of (5-bromo-1H-indol-3-ylmethyl)-dimethyl-amine (11.2 g, 44.1 mmol) in benzene (145 mL) was added iodomethane (8.2 mL, 130 mmol). The reaction mixture was stirred overnight at room temperature and concentrated. The residue was dissolved in THF (210 mL). Trimethylsilyl cyanide (11.7 mL, 87.7 ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Nitrile | null | null | c1ccc2[nH]ccc2c1 | Other | C1=CC=CC=C1.O.C1CCOC1 | null | 8 | CN(C)Cc1c[nH]c2ccc(Br)cc12>C1=CC=CC=C1.O.C1CCOC1>N#CCc1c[nH]c2ccc(Br)cc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-072604a9467041429ec0d15ea0bffc5c | CI.N#CCc1c[nH]c2ccc(-c3ccc(C(F)(F)F)cc3)cc12>>Cn1cc(CC#N)c2cc(-c3ccc(C(F)(F)F)cc3)ccc21 | FC(C1=CC=C(C=C1)C=1C=C2C(=CNC2=CC1)CC#N)(F)F.[H-].[Na+].IC>>CN1C=C(C2=CC(=CC=C12)C1=CC=C(C=C1)C(F)(F)F)CC#N | I[CH3:1].[nH:2]1[cH:3][c:4]([CH2:5][C:6]#[N:7])[c:8]2[cH:9][c:10](-[c:11]3[cH:12][cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20]3)[cH:21][cH:22][c:23]12>>[CH3:1][n:2]1[cH:3][c:4]([CH2:5][C:6]#[N:7])[c:8]2[cH:9][c:10](-[c:11]3[cH:12][cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20]3)[cH:21][cH:22][c:23... | CI.N#CCc1c[nH]c2ccc(-c3ccc(C(F)(F)F)cc3)cc12 | Cn1cc(CC#N)c2cc(-c3ccc(C(F)(F)F)cc3)ccc21 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 5f4295751cbf2eac77c77b599ebb727e1800dd106de3a7476670f0ac76dbeba5 | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | c1ccc(-c2ccc3[nH]ccc3c2)cc1 | I-[CH3;D1;+0:1].[c:2]:[c:3]1:[c:4]:[c:5]:[c:6]:[nH;D2;+0:7]:1>>[CH3;D1;+0:1]-[n;H0;D3;+0:7]1:[c:6]:[c:5]:[c:4]:[c:3]:1:[c:2] | 60 | [{"value": 60.0, "product": "CN1C=C(C2=CC(=CC=C12)C1=CC=C(C=C1)C(F)(F)F)CC#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.8, "product": "CN1C=C(C2=CC(=CC=C12)C1=CC=C(C=C1)C(F)(F)F)CC#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | [1-Methyl-5-(4-trifluoromethyl-phenyl)-1H-indol-3-yl]-acetonitrile was prepared from [5-(4-trifluoromethyl-phenyl)-1H-indol-3-yl]-acetonitrile (0.377 g, 1.26 mmol), sodium hydride (0.117 g, 2.93 mmol of a 60% dispersion on mineral oil), iodomethane ( 0.17 mL, 2.8 mmol) and THF (10 mL) according to the procedure describ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | HI | C1CCOC1 | null | null | CI.N#CCc1c[nH]c2ccc(-c3ccc(C(F)(F)F)cc3)cc12>C1CCOC1>Cn1cc(CC#N)c2cc(-c3ccc(C(F)(F)F)cc3)ccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3f3e8c19a7c34e0fbbd45aff63378f4c | Cc1cccc(-c2ccc3c(c2)c(C(=O)C(=O)O)cn3Cc2ccc(C(C)(C)C)cc2)c1>>Cc1cccc(-c2ccc3c(c2)c(CC(=O)O)cn3Cc2ccc(C(C)(C)C)cc2)c1 | O.NN.C(C)(C)(C)C1=CC=C(CN2C=C(C3=CC(=CC=C23)C2=CC(=CC=C2)C)C(C(=O)O)=O)C=C1.C[O-].[Na+]>>C(C)(C)(C)C1=CC=C(CN2C=C(C3=CC(=CC=C23)C2=CC(=CC=C2)C)CC(=O)O)C=C1 | O=[C:14]([c:13]1[c:11]2[c:10]([cH:9][cH:8][c:7](-[c:6]3[cH:5][cH:4][cH:3][c:2]([CH3:1])[cH:31]3)[cH:12]2)[n:19]([CH2:20][c:21]2[cH:22][cH:23][c:24]([C:25]([CH3:26])([CH3:27])[CH3:28])[cH:29][cH:30]2)[cH:18]1)[C:15](=[O:16])[OH:17]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]3[c:11]([cH:12]2)[c:13]([C... | Cc1cccc(-c2ccc3c(c2)c(C(=O)C(=O)O)cn3Cc2ccc(C(C)(C)C)cc2)c1 | Cc1cccc(-c2ccc3c(c2)c(CC(=O)O)cn3Cc2ccc(C(C)(C)C)cc2)c1 | null | null | COCCO | Reduction | OtherReaction | bdac4f77103f4da1c5b42ea95e05b0b7b31176b78204db5f4144ffca7b3d54d5 | f9ba67182f94acd5fbe41487f8f71e26bccf898b8fc8091ef46f4363de5628d4 | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | O=[C;H0;D3;+0:1](-[C:2](=[O;D1;H0:3])-[O;D1;H1:4])-[c:5]1:[c:6]:[c:7]:[#7;a:8](-[C:9]):[c:10]:1>>[C:9]-[#7;a:8]1:[c:7]:[c:6]:[c:5](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[O;D1;H1:4]):[c:10]:1 | 46.7 | [{"value": 46.7, "product": "C(C)(C)(C)C1=CC=C(CN2C=C(C3=CC(=CC=C23)C2=CC(=CC=C2)C)CC(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 1 | HOUR | Hydrazine monohydrate (0.56 mL, 11.75 mmol) was added to a stirring solution of 2-[1-[4-(tert-Butyl)benzyl]-5-(3-methylphenyl)-1H-indol-3-yl]-2-oxoacetic acid (WAY-201417, 1.0 g, 2.35 mmol) in 2-methoxyethanol (10 mL). After the mixture was heated to 60° C. Sodium methoxide (1.34 g, 23.5 mmol) was added portionwise to ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | null | null | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | Other | COCCO | 60 | 1 | Cc1cccc(-c2ccc3c(c2)c(C(=O)C(=O)O)cn3Cc2ccc(C(C)(C)C)cc2)c1>COCCO>Cc1cccc(-c2ccc3c(c2)c(CC(=O)O)cn3Cc2ccc(C(C)(C)C)cc2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d6a90b55366546e79a79da13a90f1eb1 | Cc1ccc(Cn2cc(C(=O)C(=O)O)c3cc(-c4ccc(OC(F)(F)F)cc4)ccc32)cc1>>Cc1ccc(Cn2cc(CC(=O)O)c3cc(-c4ccc(OC(F)(F)F)cc4)ccc32)cc1 | CC1=CC=C(CN2C=C(C3=CC(=CC=C23)C2=CC=C(C=C2)OC(F)(F)F)C(C(=O)O)=O)C=C1.O.NN.C[O-].[Na+]>>CC1=CC=C(CN2C=C(C3=CC(=CC=C23)C2=CC=C(C=C2)OC(F)(F)F)CC(=O)O)C=C1 | O=[C:10]([c:9]1[cH:8][n:7]([CH2:6][c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:32][cH:31]2)[c:30]2[c:14]1[cH:15][c:16](-[c:17]1[cH:18][cH:19][c:20]([O:21][C:22]([F:23])([F:24])[F:25])[cH:26][cH:27]1)[cH:28][cH:29]2)[C:11](=[O:12])[OH:13]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][n:7]2[cH:8][c:9]([CH2:10][C:11](=[O:12])[OH:13])[c:... | Cc1ccc(Cn2cc(C(=O)C(=O)O)c3cc(-c4ccc(OC(F)(F)F)cc4)ccc32)cc1 | Cc1ccc(Cn2cc(CC(=O)O)c3cc(-c4ccc(OC(F)(F)F)cc4)ccc32)cc1 | null | null | null | Reduction | OtherReaction | bdac4f77103f4da1c5b42ea95e05b0b7b31176b78204db5f4144ffca7b3d54d5 | f9ba67182f94acd5fbe41487f8f71e26bccf898b8fc8091ef46f4363de5628d4 | c1ccc(Cn2ccc3cc(-c4ccccc4)ccc32)cc1 | O=[C;H0;D3;+0:1](-[C:2](=[O;D1;H0:3])-[O;D1;H1:4])-[c:5]1:[c:6]:[c:7]:[#7;a:8](-[C:9]):[c:10]:1>>[C:9]-[#7;a:8]1:[c:7]:[c:6]:[c:5](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[O;D1;H1:4]):[c:10]:1 | null | [] | null | null | null | null | The title compound was prepared from {1-(4-methylbenzyl)-5-[4-(trifluoromethoxy)phenyl]-1H-indol-3-yl}(oxo)acetic acid, hydrazine monohydrate and sodium methoxide according to the procedure described in Example 64. The product was obtained as a brown solid, mp: 62-63° C. Mass spectrum (−ESI, [M−H]−) m/z 438. 1HNMR (400... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | null | null | c1ccccc1.c1ccc2[nH]ccc2c1.c1ccccc1 | Other | null | null | null | Cc1ccc(Cn2cc(C(=O)C(=O)O)c3cc(-c4ccc(OC(F)(F)F)cc4)ccc32)cc1>>Cc1ccc(Cn2cc(CC(=O)O)c3cc(-c4ccc(OC(F)(F)F)cc4)ccc32)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0005d89300f14179ba31eec63084a118 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Oc1ccc2ncccc2c1>>COc1cc2c(Oc3ccc4ncccc4c3)ncnc2cc1OCCCN1CCOCC1 | [OH-].[Na+].ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1.C([O-])([O-])=O.[K+].[K+].OC=1C=C2C=CC=NC2=CC1>>COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)OC=1C=C2C=CC=NC2=CC1 | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:23]([O:24][CH2:25][CH2:26][CH2:27][N:28]3[CH2:29][CH2:30][O:31][CH2:32][CH2:33]3)[cH:22][c:21]2[n:20][cH:19][n:18]1.[OH:7][c:8]1[cH:9][cH:10][c:11]2[n:12][cH:13][cH:14][cH:15][c:16]2[cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[n:12][cH:13][cH:14... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Oc1ccc2ncccc2c1 | COc1cc2c(Oc3ccc4ncccc4c3)ncnc2cc1OCCCN1CCOCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1cnc2ccc(Oc3ncnc4cc(OCCCN5CCOCC5)ccc34)cc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[O;H0;D2;+0:9]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 55 | [{"value": 55.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)OC=1C=C2C=CC=NC2=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.5, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)OC=1C=C2C=CC=NC2=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 5 | HOUR | A mixture of 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (225 mg, 0.67 mmol), potassium carbonate (106 mg, 0.77 mmol) and 6-hydroxyquinoline (112 mg, 0.77 mmol) in DMF (7.5 ml) was stirred at 100° C. for 5 hours and allowed to cool to ambient temperature. The reaction mixture was treated with 1M aqueous sodiu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncccc2c1.c1ccc2ncncc2c1.C1COCC[NH]1 | HCl | CN(C)C=O | 100 | 5 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Oc1ccc2ncccc2c1>CN(C)C=O>COc1cc2c(Oc3ccc4ncccc4c3)ncnc2cc1OCCCN1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b4837dce22a34cdc876d8215b2e10c85 | COc1cc(C(N)=O)c(N)cc1OCc1ccccc1>>COc1cc2c(=O)[nH]cnc2cc1OCc1ccccc1 | NC1=C(C(=O)N)C=C(C(=C1)OCC1=CC=CC=C1)OC.CN(C)C=NC=[N+](C)C.[Cl-].C(C)(=O)[O-].[Na+].C(C)(=O)O>>C(C1=CC=CC=C1)OC1=C(C=C2C(NC=NC2=C1)=O)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[NH2:8])[c:11]([NH2:10])[cH:12][c:13]1[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6](=[O:7])[nH:8][cH:9][n:10][c:11]2[cH:12][c:13]1[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | COc1cc(C(N)=O)c(N)cc1OCc1ccccc1 | COc1cc2c(=O)[nH]cnc2cc1OCc1ccccc1 | null | null | O1CCOCC1 | Aromatic Heterocycle Formation | OtherReaction | 0798449d56bc7e7756a703d33bd60780d26c4986e39e1809e15228456c95135b | 3074b6c74bc99545969aa05d42dae7b149d9d6bb1b36a52cec3a362e1e7f7ca0 | O=c1[nH]cnc2cc(OCc3ccccc3)ccc12 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4](-[C;H0;D3;+0:5](-[NH2;D1;+0:6])=[O;D1;H0:7]):[c:8]>>[O;D1;H0:7]=[c;H0;D3;+0:5]1:[nH;D2;+0:6]:[c:9]:[n;H0;D2;+0:1]:[c:2](:[c:3]):[c:4]:1:[c:8] | 84 | [{"value": 84.0, "product": "C(C1=CC=CC=C1)OC1=C(C=C2C(NC=NC2=C1)=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.0, "product": "C(C1=CC=CC=C1)OC1=C(C=C2C(NC=NC2=C1)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-amino-4-benzyloxy-5-methoxybenzamide (10 g, 0.04 mol), (J. Med. Chem. 1977, vol 20, 146–149), and Gold's reagent (7.4 g, 0.05 mol) in dioxane (100ml) was stirred and heated at reflux for 24 hours. Sodium acetate (3.02 g, 0.037 mol) and acetic acid (1.65 ml, 0.029 mol) were added to the reaction mixture a... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Primary amine | null | c1ccccc1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccccc1 | Other | O1CCOCC1 | null | null | COc1cc(C(N)=O)c(N)cc1OCc1ccccc1>O1CCOCC1>COc1cc2c(=O)[nH]cnc2cc1OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f526d9d4190842b6bad655cc059ecc6a | COc1cc2c(=O)[nH]cnc2cc1OCc1ccccc1.O=S(Cl)Cl>>COc1cc2c(Cl)ncnc2cc1OCc1ccccc1 | C(C1=CC=CC=C1)OC1=C(C=C2C(NC=NC2=C1)=O)OC.CN(C)C=O.S(=O)(Cl)Cl>>C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)Cl)OC | O=[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:13]([O:14][CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[cH:12][c:11]2[n:10][cH:9][nH:8]1.O=S(Cl)[Cl:7]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([Cl:7])[n:8][cH:9][n:10][c:11]2[cH:12][c:13]1[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | COc1cc2c(=O)[nH]cnc2cc1OCc1ccccc1.O=S(Cl)Cl | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1 | null | null | null | Functional Group Interconversion | OtherReaction | 3788560e87eee8765e749543914a91a512631307b97fad163ebef894d2a0ea68 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc(COc2ccc3cncnc3c2)cc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9] | null | [] | null | null | null | null | 7-Benzyloxy-6-methoxy-3,4-dihydroquinazolin-4-one (35 g, 124 mmol) was suspended in thionyl chloride (440 ml) and DMF (1.75 ml) and heated at reflux for 4 hours. The thionyl chloride was evaporated under vacuum and the residue azeotroped with toluene three times. The residue was dissolved in NMP (250 ml) to give a solu... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccccc1 | HCl | null | null | null | COc1cc2c(=O)[nH]cnc2cc1OCc1ccccc1.O=S(Cl)Cl>>COc1cc2c(Cl)ncnc2cc1OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-672212fe43174053a6b602a2597f9975 | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Oc1ccccc1>>COc1cc2c(Oc3ccccc3)ncnc2cc1OCc1ccccc1 | O.[H-].[Na+].C1(=CC=CC=C1)O.C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)Cl)OC>>C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)OC1=CC=CC=C1)OC | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:19]([O:20][CH2:21][c:22]3[cH:23][cH:24][cH:25][cH:26][cH:27]3)[cH:18][c:17]2[n:16][cH:15][n:14]1.[OH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][cH:11][cH:12][cH:13]3)[n:14][cH:15][n:16][c:17]2[cH:18][c:19]1[O:20][CH... | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Oc1ccccc1 | COc1cc2c(Oc3ccccc3)ncnc2cc1OCc1ccccc1 | null | null | CN1CCCC1=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(COc2ccc3c(Oc4ccccc4)ncnc3c2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[O;H0;D2;+0:9]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 83 | [{"value": 83.0, "product": "C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)OC1=CC=CC=C1)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Phenol (29.05 g, 309 mmol) was dissolved in NMP (210 ml), sodium hydride (11.025 g, 60% dispersion in mineral oil) was added in portions with cooling and the mixture was stirred for 3 hours. The viscous suspension was diluted with NMP (180 ml) and stirred overnight. The solution of 7-benzyloxy-4-chloro-6-methoxyquinazo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccccc1.c1ccc2ncncc2c1.c1ccccc1 | HCl | CN1CCCC1=O | null | 3 | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Oc1ccccc1>CN1CCCC1=O>COc1cc2c(Oc3ccccc3)ncnc2cc1OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-36e35b2dcbe54393ad2cd3b23febd9d7 | COc1cc2c(Oc3ccccc3)ncnc2cc1OCc1ccccc1>>COc1cc2c(Oc3ccccc3)ncnc2cc1O | C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)OC1=CC=CC=C1)OC>>OC1=C(C=C2C(=NC=NC2=C1)OC1=CC=CC=C1)OC | c1ccc(C[O:20][c:19]2[c:3]([O:2][CH3:1])[cH:4][c:5]3[c:6]([O:7][c:8]4[cH:9][cH:10][cH:11][cH:12][cH:13]4)[n:14][cH:15][n:16][c:17]3[cH:18]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][cH:11][cH:12][cH:13]3)[n:14][cH:15][n:16][c:17]2[cH:18][c:19]1[OH:20] | COc1cc2c(Oc3ccccc3)ncnc2cc1OCc1ccccc1 | COc1cc2c(Oc3ccccc3)ncnc2cc1O | null | null | C(=O)(C(F)(F)F)O | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(Oc2ncnc3ccccc23)cc1 | [#7;a:1]:[c:2]:[c:3]:[c:4](-[O;H0;D2;+0:5]-C-c1:c:c:c:c:c:1):[c:6]>>[#7;a:1]:[c:2]:[c:3]:[c:4](-[OH;D1;+0:5]):[c:6] | 96 | [{"value": 96.0, "product": "OC1=C(C=C2C(=NC=NC2=C1)OC1=CC=CC=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.0, "product": "OC1=C(C=C2C(=NC=NC2=C1)OC1=CC=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 7-Benzyloxy-6-methoxy-4-phenoxyquinazoline (36.95 g, 105.5 mmol) was suspended in TFA (420 ml) and heated at reflux for 3 hours. The reaction mixture was allowed to cool and evaporated under vacuum. The residue was stirred mechanically in water then basified with saturated aqueous sodium hydrogen carbonate solution and... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccccc1.c1ccc2ncncc2c1 | Other | C(=O)(C(F)(F)F)O | null | null | COc1cc2c(Oc3ccccc3)ncnc2cc1OCc1ccccc1>C(=O)(C(F)(F)F)O>COc1cc2c(Oc3ccccc3)ncnc2cc1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-67df1fd40f8a49ee96ddc5e8b3355166 | C1COCCN1.ClCCCBr>>ClCCCN1CCOCC1 | N1CCOCC1.BrCCCCl>>ClCCCN1CCOCC1 | [NH:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1.Br[CH2:4][CH2:3][CH2:2][Cl:1]>>[Cl:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1 | C1COCCN1.ClCCCBr | ClCCCN1CCOCC1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 2bad30dcdb0a20edb8ce877f072b133eedfd870621da393ec393128bfee00977 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | C1COCCN1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#8:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:8]-[C:9]-[#8:4]-[C:5]-[C:6]-1 | 77.2 | [{"value": 77.0, "product": "ClCCCN1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.2, "product": "ClCCCN1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | Morpholine (52.2 ml, 600 mmol) and 1-bromo-3-chloropropane (30 ml, 300 mmol) were dissolved in dry toluene (180 ml) and heated to 70° C. for 3 hours. The solid was removed by filtration and the filtrate evaporated under vacuum. The resulting oil was decanted from the additional solid residue and the oil was vacuum dist... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1COCCN1 | C1COCC[NH]1 | C1COCC[NH]1 | HBr | C1(=CC=CC=C1)C | 70 | null | C1COCCN1.ClCCCBr>C1(=CC=CC=C1)C>ClCCCN1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-abe597ff8efa41fdb57f768e0a03584f | COc1cc2c(Oc3ccccc3)ncnc2cc1OCCCN1CCOCC1>>COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCOCC1 | COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)OC1=CC=CC=C1>>COC=1C=C2C(NC=NC2=CC1OCCCN1CCOCC1)=O | c1ccc([O:7][c:6]2[c:5]3[cH:4][c:3]([O:2][CH3:1])[c:13]([O:14][CH2:15][CH2:16][CH2:17][N:18]4[CH2:19][CH2:20][O:21][CH2:22][CH2:23]4)[cH:12][c:11]3[n:10][cH:9][n:8]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6](=[O:7])[nH:8][cH:9][n:10][c:11]2[cH:12][c:13]1[O:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][O:21][CH2:22][... | COc1cc2c(Oc3ccccc3)ncnc2cc1OCCCN1CCOCC1 | COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCOCC1 | null | null | Cl | Miscellaneous | OtherReaction | 35688e011295b3fd61af43341ada8b6a68d47734fb10ccd0734838342d415c85 | 291cad8b6dfbbd2c823b5c9d45efc37a166dc3454a9f151ac48cb357f4bc155f | O=c1[nH]cnc2cc(OCCCN3CCOCC3)ccc12 | [c:1]:[c:2]1:[#7;a:3]:[c:4]:[n;H0;D2;+0:5]:[c;H0;D3;+0:6](-[O;H0;D2;+0:7]-c2:c:c:c:c:c:2):[c:8]:1:[c:9]>>[O;H0;D1;+0:7]=[c;H0;D3;+0:6]1:[nH;D2;+0:5]:[c:4]:[#7;a:3]:[c:2](:[c:1]):[c:8]:1:[c:9] | 89.1 | [{"value": 89.0, "product": "COC=1C=C2C(NC=NC2=CC1OCCCN1CCOCC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.1, "product": "COC=1C=C2C(NC=NC2=CC1OCCCN1CCOCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 6-Methoxy-7-(3-morpholinopropoxy)-4-phenoxyquinazoline (33.08 g, 84 mmol) was dissolved in 6M aqueous hydrochloric acid (800 ml) and heated at reflux for 1.5 hours. The reaction mixture was decanted and concentrated to 250 ml then basified (pH9) with saturated aqueous sodium hydrogen carbonate solution. The aqueous lay... | 10.6084/m9.figshare.5104873.v1 | null | Ether | null | c1ccccc1.c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1COCC[NH]1 | Other | Cl | null | null | COc1cc2c(Oc3ccccc3)ncnc2cc1OCCCN1CCOCC1>Cl>COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c5247d25e4c64561a536322973f5e5ef | COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCOCC1.O=S(Cl)Cl>>COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1 | COC=1C=C2C(NC=NC2=CC1OCCCN1CCOCC1)=O.CN(C)C=O.S(=O)(Cl)Cl>>ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1 | O=[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:13]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)[cH:12][c:11]2[n:10][cH:9][nH:8]1.O=S(Cl)[Cl:7]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([Cl:7])[n:8][cH:9][n:10][c:11]2[cH:12][c:13]1[O:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][O:21][CH2:22]... | COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCOCC1.O=S(Cl)Cl | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1 | null | null | null | Functional Group Interconversion | OtherReaction | 3788560e87eee8765e749543914a91a512631307b97fad163ebef894d2a0ea68 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ncc2ccc(OCCCN3CCOCC3)cc2n1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9] | 52 | [{"value": 52.0, "product": "ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 6-Methoxy-7-(3-morpholinopropoxy)-3,4-dihydroquinazolin-4-one (23.9 g, 75 mmol) was suspended in thionyl chloride (210 ml) and DMF (1.8 ml) then heated at reflux for 1.5 hours. The thionyl chloride was removed by evaporation under vacuum and the residue azeotroped with toluene three times. The residue was taken up in w... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1COCC[NH]1 | HCl | null | null | null | COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCOCC1.O=S(Cl)Cl>>COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3b09a4491fb64908b3138363b9488451 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Oc1ccc2cccnc2c1>>COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1OCCCN1CCOCC1 | [OH-].[Na+].ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1.C([O-])([O-])=O.[K+].[K+].OC1=CC=C2C=CC=NC2=C1>>COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)OC1=CC=C2C=CC=NC2=C1 | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:23]([O:24][CH2:25][CH2:26][CH2:27][N:28]3[CH2:29][CH2:30][O:31][CH2:32][CH2:33]3)[cH:22][c:21]2[n:20][cH:19][n:18]1.[OH:7][c:8]1[cH:9][cH:10][c:11]2[cH:12][cH:13][cH:14][n:15][c:16]2[cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[cH:12][cH:13][cH:1... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Oc1ccc2cccnc2c1 | COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1OCCCN1CCOCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1cnc2cc(Oc3ncnc4cc(OCCCN5CCOCC5)ccc34)ccc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#7;a:9]:[c:10]:[c:11]:[c:12](-[OH;D1;+0:13]):[c:14]>>[#7;a:9]:[c:10]:[c:11]:[c:12](-[O;H0;D2;+0:13]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:14] | 39 | [{"value": 39.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)OC1=CC=C2C=CC=NC2=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 38.8, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)OC1=CC=C2C=CC=NC2=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 5 | HOUR | A mixture of 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (225 mg, 0.67 mmol), (prepared as described for the starting material in Example 1), potassium carbonate (106 g, 0.77 mmol) and 7-hydroxyquinoline (112 mg, 0.77 mmol) in DMF (7.5 ml) was stirred at 100° C. for 5 hours and allowed to cool to ambient temp... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncccc2c1.c1ccc2ncncc2c1.C1COCC[NH]1 | HCl | CN(C)C=O | 100 | 5 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Oc1ccc2cccnc2c1>CN(C)C=O>COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1OCCCN1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8f09a10886004035a4e54b16cdcc6b3a | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Oc1cccc2ccccc12>>COc1cc2c(Oc3cccc4ccccc34)ncnc2cc1OCCCN1CCOCC1 | [OH-].[Na+].ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1.C([O-])([O-])=O.[K+].[K+].C1(=CC=CC2=CC=CC=C12)O>>COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)OC1=CC=CC2=CC=CC=C12 | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:23]([O:24][CH2:25][CH2:26][CH2:27][N:28]3[CH2:29][CH2:30][O:31][CH2:32][CH2:33]3)[cH:22][c:21]2[n:20][cH:19][n:18]1.[OH:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][cH:11][c:12]4[cH:13][cH:... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Oc1cccc2ccccc12 | COc1cc2c(Oc3cccc4ccccc34)ncnc2cc1OCCCN1CCOCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc2c(Oc3ncnc4cc(OCCCN5CCOCC5)ccc34)cccc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[O;H0;D2;+0:9]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 65 | [{"value": 65.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)OC1=CC=CC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)OC1=CC=CC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 5 | HOUR | A mixture of 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (225 mg, 0.67 mmol), (prepared as described for the starting material in Example 1), potassium carbonate (106 mg, 0.77 mmol) and 1-naphthol (111 mg, 0.77 mmol) in DMF (7.5 ml) was stirred at 100° C. for 5 hours then allowed to cool to ambient temperatur... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ccccc2c1.c1ccc2ncncc2c1.C1COCC[NH]1 | HCl | CN(C)C=O | 100 | 5 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Oc1cccc2ccccc12>CN(C)C=O>COc1cc2c(Oc3cccc4ccccc34)ncnc2cc1OCCCN1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-19d86247b43c4c8da664f827b85e6008 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Cc1ccnc2cc(O)ccc12>>COc1cc2c(Oc3ccc4c(C)ccnc4c3)ncnc2cc1OCCCN1CCOCC1 | [OH-].[Na+].ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1.C([O-])([O-])=O.[K+].[K+].OC1=CC=C2C(=CC=NC2=C1)C>>COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)OC1=CC=C2C(=CC=NC2=C1)C | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:24]([O:25][CH2:26][CH2:27][CH2:28][N:29]3[CH2:30][CH2:31][O:32][CH2:33][CH2:34]3)[cH:23][c:22]2[n:21][cH:20][n:19]1.[OH:7][c:8]1[cH:9][cH:10][c:11]2[c:12]([CH3:13])[cH:14][cH:15][n:16][c:17]2[cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[c:12]([CH... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Cc1ccnc2cc(O)ccc12 | COc1cc2c(Oc3ccc4c(C)ccnc4c3)ncnc2cc1OCCCN1CCOCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1cnc2cc(Oc3ncnc4cc(OCCCN5CCOCC5)ccc34)ccc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#7;a:9]:[c:10]:[c:11]:[c:12](-[OH;D1;+0:13]):[c:14]>>[#7;a:9]:[c:10]:[c:11]:[c:12](-[O;H0;D2;+0:13]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:14] | 57 | [{"value": 57.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)OC1=CC=C2C(=CC=NC2=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.7, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCOCC1)OC1=CC=C2C(=CC=NC2=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 5 | HOUR | A mixture of 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (225 mg, 0.67 mmol), (prepared as described for the starting material in Example 1), potassium carbonate (106 mg, 0.77 mmol) and 7-hydroxy-4-methylquinoline (122 mg, 0.77 mmol), (Chem. Berich. 1967, 100, 2077), in DMF (7.5 ml) was stirred at 100° C. for... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncccc2c1.c1ccc2ncncc2c1.C1COCC[NH]1 | HCl | CN(C)C=O | 100 | 5 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.Cc1ccnc2cc(O)ccc12>CN(C)C=O>COc1cc2c(Oc3ccc4c(C)ccnc4c3)ncnc2cc1OCCCN1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b95c0f24fb5144c7b69042eedf25564a | COc1cc2c(Cl)ncnc2cc1OCCCN1CCS(=O)(=O)CC1.Oc1ccc2cccnc2c1>>COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1OCCCN1CCS(=O)(=O)CC1 | [OH-].[Na+].ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCS(CC1)(=O)=O.C([O-])([O-])=O.[K+].[K+].OC1=CC=C2C=CC=NC2=C1>>O=S1(CCN(CC1)CCCOC1=C(C=C2C(=NC=NC2=C1)OC1=CC=C2C=CC=NC2=C1)OC)=O | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:23]([O:24][CH2:25][CH2:26][CH2:27][N:28]3[CH2:29][CH2:30][S:31](=[O:32])(=[O:33])[CH2:34][CH2:35]3)[cH:22][c:21]2[n:20][cH:19][n:18]1.[OH:7][c:8]1[cH:9][cH:10][c:11]2[cH:12][cH:13][cH:14][n:15][c:16]2[cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCS(=O)(=O)CC1.Oc1ccc2cccnc2c1 | COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1OCCCN1CCS(=O)(=O)CC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | O=S1(=O)CCN(CCCOc2ccc3c(Oc4ccc5cccnc5c4)ncnc3c2)CC1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#7;a:9]:[c:10]:[c:11]:[c:12](-[OH;D1;+0:13]):[c:14]>>[#7;a:9]:[c:10]:[c:11]:[c:12](-[O;H0;D2;+0:13]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:14] | 73 | [{"value": 73.0, "product": "O=S1(CCN(CC1)CCCOC1=C(C=C2C(=NC=NC2=C1)OC1=CC=C2C=CC=NC2=C1)OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.7, "product": "O=S1(CCN(CC1)CCCOC1=C(C=C2C(=NC=NC2=C1)OC1=CC=C2C=CC=NC2=C1)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 5 | HOUR | A mixture of 4-chloro-7-(3-(1,1-dioxothiomorpholino)propoxy)-6-methoxyquinazoline (220 mg, 0.57 mmol), potassium carbonate (106 mg, 0.77 mmol) and 7-hydroxyquinoline (111 mg, 0.76 mmol) in DMF (7.5 ml) was stirred at 100° C. for 5 hours then allowed to cool to ambient temperature. The reaction mixture was treated with ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncccc2c1.c1ccc2ncncc2c1.C1CSCC[NH]1 | HCl | CN(C)C=O | 100 | 5 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCS(=O)(=O)CC1.Oc1ccc2cccnc2c1>CN(C)C=O>COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1OCCCN1CCS(=O)(=O)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6e4a2e6d07af474dba1790077b8de6ed | COc1cc2c(=O)[nH]cnc2cc1OCc1ccccc1.O=S(Cl)Cl>>COc1cc2c(Cl)ncnc2cc1OCc1ccccc1 | C(C1=CC=CC=C1)OC1=C(C=C2C(NC=NC2=C1)=O)OC.CN(C)C=O.S(=O)(Cl)Cl>>C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)Cl)OC | O=[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:13]([O:14][CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[cH:12][c:11]2[n:10][cH:9][nH:8]1.O=S(Cl)[Cl:7]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([Cl:7])[n:8][cH:9][n:10][c:11]2[cH:12][c:13]1[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | COc1cc2c(=O)[nH]cnc2cc1OCc1ccccc1.O=S(Cl)Cl | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1 | null | null | null | Functional Group Interconversion | OtherReaction | 3788560e87eee8765e749543914a91a512631307b97fad163ebef894d2a0ea68 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc(COc2ccc3cncnc3c2)cc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9] | null | [] | null | null | null | null | 7-Benzyloxy-6-methoxy-3,4-dihydroquinazolin-4-one (20.3 g, 124 mmol), (prepared as described for the starting material in Example 1), was taken up in thionyl chloride (440 ml) and DMF (1.75 ml) then heated at reflux for 4 hours. The thionyl chloride was evaporated under vacuum and the residue azeotroped with toluene th... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccccc1 | HCl | null | null | null | COc1cc2c(=O)[nH]cnc2cc1OCc1ccccc1.O=S(Cl)Cl>>COc1cc2c(Cl)ncnc2cc1OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c9a78dfb7663487fa2f53baeda49ab42 | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Oc1ccc(Cl)cc1F>>COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1OCc1ccccc1 | O.C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)Cl)OC.C([O-])([O-])=O.[K+].[K+].ClC1=CC(=C(C=C1)O)F>>C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)OC1=C(C=C(C=C1)Cl)F)OC | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:21]([O:22][CH2:23][c:24]3[cH:25][cH:26][cH:27][cH:28][cH:29]3)[cH:20][c:19]2[n:18][cH:17][n:16]1.[OH:7][c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]1[F:15]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]3[F:15])[n:16][cH:17][n:18][c:1... | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Oc1ccc(Cl)cc1F | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1OCc1ccccc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(COc2ccc3c(Oc4ccccc4)ncnc3c2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[O;H0;D2;+0:9]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 76 | [{"value": 76.0, "product": "C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)OC1=C(C=C(C=C1)Cl)F)OC", "details": "PERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 5 | HOUR | A mixture of the crude 7-benzyloxy-4-chloro-6-methoxyquinazoline, potassium carbonate (50 g, 362 mmol) and 4-chloro-2-fluorophenol (8.8 ml, 83 mmol) in DMF (500 ml) was stirred at 100° C. for 5 hours then allowed to cool to ambient temperature overnight. The reaction mixture was poured into water (21) and was stirred a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccccc1.c1ccc2ncncc2c1.c1ccccc1 | HCl | CN(C)C=O | 100 | 5 | COc1cc2c(Cl)ncnc2cc1OCc1ccccc1.Oc1ccc(Cl)cc1F>CN(C)C=O>COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ad22f7bf657a4e92a7fad388b17051f4 | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1OCc1ccccc1>>COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1O | C(C1=CC=CC=C1)OC1=C(C=C2C(=NC=NC2=C1)OC1=C(C=C(C=C1)Cl)F)OC.C1(=CC=CC=C1)C>>ClC1=CC(=C(OC2=NC=NC3=CC(=C(C=C23)OC)O)C=C1)F | c1ccc(C[O:22][c:21]2[c:3]([O:2][CH3:1])[cH:4][c:5]3[c:6]([O:7][c:8]4[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]4[F:15])[n:16][cH:17][n:18][c:19]3[cH:20]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]3[F:15])[n:16][cH:17][n:18][c:19]2[cH:20][c:21]1[OH:22] | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1OCc1ccccc1 | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1O | null | null | C(=O)(C(F)(F)F)O | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(Oc2ncnc3ccccc23)cc1 | [#7;a:1]:[c:2]:[c:3]:[c:4](-[O;H0;D2;+0:5]-C-c1:c:c:c:c:c:1):[c:6]>>[#7;a:1]:[c:2]:[c:3]:[c:4](-[OH;D1;+0:5]):[c:6] | 1,999.3 | [{"value": 1999.3, "product": "ClC1=CC(=C(OC2=NC=NC3=CC(=C(C=C23)OC)O)C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 7-Benzyloxy-4-(4-chloro-2-fluorophenoxy)-6-methoxyquinazoline (1.4 g, 3.4 mmol) was suspended in TFA (15 ml) and heated at reflux for 3 hours. The reaction mixture was allowed to cool, toluene was added and the volatiles were removed by evaporation under vacuum. The residue was triturated with ether and then acetone. T... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccccc1.c1ccc2ncncc2c1 | Other | C(=O)(C(F)(F)F)O | null | null | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1OCc1ccccc1>C(=O)(C(F)(F)F)O>COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f34a995a35ed4900be5a3bf68a995419 | C=CS(=O)(=O)C=C.NCCCO>>O=S1(=O)CCN(CCCO)CC1 | NCCCO.C(=C)S(=O)(=O)C=C>>O=S1(CCN(CC1)CCCO)=O | [O:1]=[S:2](=[O:3])([CH:4]=[CH2:5])[CH:12]=[CH2:11].[NH2:6][CH2:7][CH2:8][CH2:9][OH:10]>>[O:1]=[S:2]1(=[O:3])[CH2:4][CH2:5][N:6]([CH2:7][CH2:8][CH2:9][OH:10])[CH2:11][CH2:12]1 | C=CS(=O)(=O)C=C.NCCCO | O=S1(=O)CCN(CCCO)CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 97798d54365c4c593d15899edbd669dc532e6c6ab5378706898ea9faa974a532 | cefc6df58e07d9b40193ef729e97b03e3cecc4f809d3df23d8c2c9918762ceb6 | O=S1(=O)CCNCC1 | [CH2;D1;+0:1]=[CH;D2;+0:2]-[#16:3](=[O;D1;H0:4])(=[O;D1;H0:5])-[CH;D2;+0:6]=[CH2;D1;+0:7].[C:8]-[C:9]-[NH2;D1;+0:10]>>[C:8]-[C:9]-[N;H0;D3;+0:10]1-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[#16:3](=[O;D1;H0:4])(=[O;D1;H0:5])-[CH2;D2;+0:6]-[CH2;D2;+0:7]-1 | 90 | [{"value": 90.0, "product": "O=S1(CCN(CC1)CCCO)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.3, "product": "O=S1(CCN(CC1)CCCO)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | null | null | A mixture of 3-amino-1-propanol (650 μl, 8.4 mmol) and vinyl sulphone (1 g, 8.4 mmol) was heated at 110° C. for 45 minutes. The mixture was allowed to cool and was purified by column chromatography eluting with methylene chloride/methanol (95/5) to give 3-(1,1-dioxothiomorpholino)-1-propanol (800 mg, 90%).
Conditions: ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Vinyl.Vinyl | Tertiary amine | null | C1CSCC[NH]1 | C1CSCC[NH]1 | null | null | 110 | null | C=CS(=O)(=O)C=C.NCCCO>>O=S1(=O)CCN(CCCO)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d77ca0f9e0534ccab0157a4494ac4df6 | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1O.O=S1(=O)CCN(CCCO)CC1>>COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1OCCCN1CCS(=O)(=O)CC1 | N(=NC(=O)N1CCCCC1)C(=O)N1CCCCC1.ClC1=CC(=C(OC2=NC=NC3=CC(=C(C=C23)OC)O)C=C1)F.C(CCC)P(CCCC)CCCC.O=S1(CCN(CC1)CCCO)=O>>ClC1=CC(=C(OC2=NC=NC3=CC(=C(C=C23)OC)OCCCN2CCS(CC2)(=O)=O)C=C1)F | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]3[F:15])[n:16][cH:17][n:18][c:19]2[cH:20][c:21]1[OH:22].O[CH2:23][CH2:24][CH2:25][N:26]1[CH2:27][CH2:28][S:29](=[O:30])(=[O:31])[CH2:32][CH2:33]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:... | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1O.O=S1(=O)CCN(CCCO)CC1 | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1OCCCN1CCS(=O)(=O)CC1 | null | null | ClCCl.CCOCC | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | O=S1(=O)CCN(CCCOc2ccc3c(Oc4ccccc4)ncnc3c2)CC1 | O-[CH2;D2;+0:1]-[C:2]-[C:3].[#7;a:4]:[c:5]:[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[#7;a:4]:[c:5]:[c:6]:[c:7](-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[C:2]-[C:3]):[c:9] | 70 | [{"value": 70.0, "product": "ClC1=CC(=C(OC2=NC=NC3=CC(=C(C=C23)OC)OCCCN2CCS(CC2)(=O)=O)C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.8, "product": "ClC1=CC(=C(OC2=NC=NC3=CC(=C(C=C23)OC)OCCCN2CCS(CC2)(=O)=O)C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 4-(4-Chloro-2-fluorophenoxy)-7-hydroxy-6-methoxyquinazoline (5.0 g, 15.6 mmol) was suspended in dichloromethane (150 ml) and tributylphosphine (11.1 ml, 44.6 mmol) was added followed by stirring at ambient temperature for 30 minutes. To this mixture was added 3-(1,1-dioxothiomorpholino)-1-propanol (4.2 g, 21.8 mmol) fo... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccc2ncncc2c1.C1CSCC[NH]1 | HO- | ClCCl.CCOCC | null | 0.5 | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1O.O=S1(=O)CCN(CCCO)CC1>ClCCl.CCOCC>COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1OCCCN1CCS(=O)(=O)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c918506e6f194ea3828b100f13b83d54 | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1OCCCN1CCS(=O)(=O)CC1>>COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCS(=O)(=O)CC1 | ClC1=CC(=C(OC2=NC=NC3=CC(=C(C=C23)OC)OCCCN2CCS(CC2)(=O)=O)C=C1)F.C(O)([O-])=O.[Na+]>>O=S1(CCN(CC1)CCCOC1=C(C=C2C(NC=NC2=C1)=O)OC)=O | Fc1cc(Cl)ccc1[O:7][c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:13]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:19][CH2:20][S:21](=[O:22])(=[O:23])[CH2:24][CH2:25]3)[cH:12][c:11]2[n:10][cH:9][n:8]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6](=[O:7])[nH:8][cH:9][n:10][c:11]2[cH:12][c:13]1[O:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:19][C... | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1OCCCN1CCS(=O)(=O)CC1 | COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCS(=O)(=O)CC1 | null | null | Cl.O | Functional Group Interconversion | OtherReaction | 2e331e7f987e2f208a7bb6621e9b7dc6ca9e78c94b181dc5496a50196c7c48fe | a99fd2343850f6fbc4a4d7024846a70661aad8ef3f77938589a06d4940f99c06 | O=c1[nH]cnc2cc(OCCCN3CCS(=O)(=O)CC3)ccc12 | Cl-c1:c:c:c(-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]2:[n;H0;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:2:[c:9]):c(-F):c:1>>[O;H0;D1;+0:1]=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9] | 87.9 | [{"value": 87.0, "product": "O=S1(CCN(CC1)CCCOC1=C(C=C2C(NC=NC2=C1)=O)OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.9, "product": "O=S1(CCN(CC1)CCCOC1=C(C=C2C(NC=NC2=C1)=O)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | null | null | 4-(4-Chloro-2-fluorophenoxy)-7-(3-(1,1-dioxothiomorpholino)propoxy)-6-methoxyquinazoline (3.5 g, 7 mmol) was dissolved in 2M aqueous hydrochloric acid (56 ml) and heated at 95° C. for 2 hours. The cooled reaction mixture was treated with solid sodium hydrogen carbonate solution to give a thick paste which was diluted w... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ether | null | c1ccccc1.c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1CSCC[NH]1 | HF | Cl.O | 95 | null | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1OCCCN1CCS(=O)(=O)CC1>Cl.O>COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCS(=O)(=O)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2f235a95498b4d10814564c5c2d79684 | COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCS(=O)(=O)CC1.O=S(Cl)Cl>>COc1cc2c(Cl)ncnc2cc1OCCCN1CCS(=O)(=O)CC1 | O=S1(CCN(CC1)CCCOC1=C(C=C2C(NC=NC2=C1)=O)OC)=O.CN(C)C=O.S(=O)(Cl)Cl>>ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCS(CC1)(=O)=O | O=[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:13]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:19][CH2:20][S:21](=[O:22])(=[O:23])[CH2:24][CH2:25]3)[cH:12][c:11]2[n:10][cH:9][nH:8]1.O=S(Cl)[Cl:7]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([Cl:7])[n:8][cH:9][n:10][c:11]2[cH:12][c:13]1[O:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:19][CH2... | COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCS(=O)(=O)CC1.O=S(Cl)Cl | COc1cc2c(Cl)ncnc2cc1OCCCN1CCS(=O)(=O)CC1 | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | 3788560e87eee8765e749543914a91a512631307b97fad163ebef894d2a0ea68 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | O=S1(=O)CCN(CCCOc2ccc3cncnc3c2)CC1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9] | 52 | [{"value": 52.0, "product": "ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCS(CC1)(=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 7-(3-(1, 1-Dioxothiomorpholino)propoxy)-6-methoxy-3,4-dihydroquinazolin-4-one (4.2 g, 11.4 mmol) was suspended in thionyl chloride (45 ml) and DMF (0.1 ml) then heated at reflux for 2.5 hours. The residue was diluted with toluene, the thionyl chloride was evaporated under vacuum, the residue was then azeotroped with to... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1CSCC[NH]1 | HCl | C1(=CC=CC=C1)C | null | null | COc1cc2c(=O)[nH]cnc2cc1OCCCN1CCS(=O)(=O)CC1.O=S(Cl)Cl>C1(=CC=CC=C1)C>COc1cc2c(Cl)ncnc2cc1OCCCN1CCS(=O)(=O)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0c43765f9a3f4cde8df5f300566eb048 | COc1cc2nc[nH]c(=O)c2cc1OC.O=S(Cl)Cl>>COc1cc2ncnc(Cl)c2cc1OC | COC=1C=C2C(NC=NC2=CC1OC)=O.S(=O)(Cl)Cl>>ClC1=NC=NC2=CC(=C(C=C12)OC)OC | O=[c:9]1[nH:8][cH:7][n:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:13]([O:14][CH3:15])[cH:12][c:11]21.O=S(Cl)[Cl:10]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8][c:9]([Cl:10])[c:11]2[cH:12][c:13]1[O:14][CH3:15] | COc1cc2nc[nH]c(=O)c2cc1OC.O=S(Cl)Cl | COc1cc2ncnc(Cl)c2cc1OC | null | CN(C)C=O | null | Functional Group Interconversion | OtherReaction | 3788560e87eee8765e749543914a91a512631307b97fad163ebef894d2a0ea68 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc2ncncc2c1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9] | null | [] | null | null | null | null | 6,7-Dimethoxy-3,4-dihydroquinazolin-4-one (290 mg, 1.4 mmol) was suspended in thionyl chloride (5 ml) and DMF (2 drops) and heated at reflux for 2 hours. The thionyl chloride was evaporated under vacuum and the residue azeotroped with toluene three times to give 4-chloro-6,7-dimethoxyquinazoline. A mixture of the crude... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | HCl | CN(C)C=O | null | null | COc1cc2nc[nH]c(=O)c2cc1OC.O=S(Cl)Cl>CN(C)C=O>COc1cc2ncnc(Cl)c2cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-37bbdc2f6f0a44189f2d09f7b653fc72 | COc1cc2ncnc(Cl)c2cc1OC.Oc1ccc2cccnc2c1>>COc1cc2ncnc(Oc3ccc4cccnc4c3)c2cc1OC | [OH-].[Na+].ClC1=NC=NC2=CC(=C(C=C12)OC)OC.C([O-])([O-])=O.[K+].[K+].OC1=CC=C2C=CC=NC2=C1>>COC=1C=C2C(=NC=NC2=CC1OC)OC1=CC=C2C=CC=NC2=C1 | Cl[c:9]1[n:8][cH:7][n:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:23]([O:24][CH3:25])[cH:22][c:21]21.[OH:10][c:11]1[cH:12][cH:13][c:14]2[cH:15][cH:16][cH:17][n:18][c:19]2[cH:20]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8][c:9]([O:10][c:11]3[cH:12][cH:13][c:14]4[cH:15][cH:16][cH:17][n:18][c:19]4[cH:20]3)[c:21]2[cH:22][c:23... | COc1cc2ncnc(Cl)c2cc1OC.Oc1ccc2cccnc2c1 | COc1cc2ncnc(Oc3ccc4cccnc4c3)c2cc1OC | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1cnc2cc(Oc3ncnc4ccccc34)ccc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#7;a:9]:[c:10]:[c:11]:[c:12](-[OH;D1;+0:13]):[c:14]>>[#7;a:9]:[c:10]:[c:11]:[c:12](-[O;H0;D2;+0:13]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:14] | 24 | [{"value": 24.0, "product": "COC=1C=C2C(=NC=NC2=CC1OC)OC1=CC=C2C=CC=NC2=C1", "details": "PERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 5 | HOUR | 6,7-Dimethoxy-3,4-dihydroquinazolin-4-one (290 mg, 1.4 mmol) was suspended in thionyl chloride (5 ml) and DMF (2 drops) and heated at reflux for 2 hours. The thionyl chloride was evaporated under vacuum and the residue azeotroped with toluene three times to give 4-chloro-6,7-dimethoxyquinazoline. A mixture of the crude... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccc2ncccc2c1 | HCl | CN(C)C=O | 100 | 5 | COc1cc2ncnc(Cl)c2cc1OC.Oc1ccc2cccnc2c1>CN(C)C=O>COc1cc2ncnc(Oc3ccc4cccnc4c3)c2cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6cd23c6db37a414ea12170b692f454ab | COc1cc(N)c(C(=O)O)cc1OC.NC=O>>COc1cc2nc[nH]c(=O)c2cc1OC | COC=1C=C(C(C(=O)O)=CC1OC)N.C(=O)N>>COC=1C=C2C(NC=NC2=CC1OC)=O | O[C:9](=[O:10])[c:11]1[c:5]([NH2:6])[cH:4][c:3]([O:2][CH3:1])[c:13]([O:14][CH3:15])[cH:12]1.O=[CH:7][NH2:8]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][nH:8][c:9](=[O:10])[c:11]2[cH:12][c:13]1[O:14][CH3:15] | COc1cc(N)c(C(=O)O)cc1OC.NC=O | COc1cc2nc[nH]c(=O)c2cc1OC | null | null | O | Aromatic Heterocycle Formation | OtherReaction | 5215b2aebdf37498a4d4a87048f2b5a68a2aa2731f8695ccc5897fee02296c51 | 42d7d0d29a255bcbf4fdad9c0b39487d2cf609ac6796e99c9c033d59efbdbdc9 | O=c1[nH]cnc2ccccc12 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[NH2;D1;+0:6]):[c:7].O=[CH;D2;+0:8]-[NH2;D1;+0:9]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[nH;D2;+0:9]:[cH;D2;+0:8]:[n;H0;D2;+0:6]:[c:5](:[c:7]):[c:3]:1:[c:4] | null | [] | 190 | CELSIUS | 3 | HOUR | A mixture of 4,5-dimethoxyanthranilic acid (19.7 g) and formamide (10 ml) was stirred and heated at 190° C. for 5 hours. The mixture was allowed to cool to approximately 80° C. and water (50 ml) was added. The mixture was then allowed to stand at ambient temperature for 3 hours. The precipitate was collected by filtrat... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amide.Primary amine | null | c1ccccc1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | HO- | O | 190 | 3 | COc1cc(N)c(C(=O)O)cc1OC.NC=O>O>COc1cc2nc[nH]c(=O)c2cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a0c6379d14634e24819afeaf203f941c | CCOC(=O)[C@@H]1CCCNC1>>CCOC(=O)[C@@H]1CCCN(C)C1 | [OH-].[Na+].C(=O)O.N1C[C@H](C(=O)OCC)CCC1.C(O)([O-])=O.[Na+]>>CN1C[C@@H](CCC1)C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C@@H:6]1[CH2:7][CH2:8][CH2:9][NH:10][CH2:12]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C@@H:6]1[CH2:7][CH2:8][CH2:9][N:10]([CH3:11])[CH2:12]1 | CCOC(=O)[C@@H]1CCCNC1 | CCOC(=O)[C@@H]1CCCN(C)C1 | null | null | C=O | Miscellaneous | OtherReaction | 4d488e5359293a04a32bace2709761d0f67be5de1412a33fc85af08dc47f7ab7 | 06e4cfdff0e70e885199cc5de7382cc871277954ed1dd9750edc3ce3b12c44bd | C1CCNCC1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[N;H0;D3;+0:6](-[C;D1;H3:9])-[C:7]-[C:8] | 73 | [{"value": 73.0, "product": "CN1C[C@@H](CCC1)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | (R)-Ethyl nipecotate (5.7 g 365 mmol), (prepared by resolution of ethyl nipecotate by treatment with L(+)-tartaric acid as described in J. Org. Chem. 1991, (56), 1168), was dissolved in 38.5% aqueous formaldehyde solution (45 ml) and formic acid (90 ml) and the mixture heated at reflux for 18 hours. The mixture was all... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1 | Other | C=O | null | null | CCOC(=O)[C@@H]1CCCNC1>C=O>CCOC(=O)[C@@H]1CCCN(C)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8a3b45b57fa245f5b86550b96b500be5 | CCOC(=O)[C@@H]1CCCN(C)C1>>CN1CCC[C@@H](CO)C1 | CN1C[C@@H](CCC1)C(=O)OCC.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+].O>>CN1C[C@@H](CCC1)CO | CCO[C:7]([C@@H:6]1[CH2:5][CH2:4][CH2:3][N:2]([CH3:1])[CH2:9]1)=[O:8]>>[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][C@@H:6]([CH2:7][OH:8])[CH2:9]1 | CCOC(=O)[C@@H]1CCCN(C)C1 | CN1CCC[C@@H](CO)C1 | null | null | CCOCC.C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | C1CCNCC1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[C:4])-[C:5]-[#7:6]>>[#7:6]-[C:5]-[C:3](-[CH2;D2;+0:1]-[OH;D1;+0:2])-[C:4] | 94.3 | [{"value": 94.0, "product": "CN1C[C@@H](CCC1)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.3, "product": "CN1C[C@@H](CCC1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 1.5 | HOUR | A solution of (R)-ethyl 1-methylpiperidine-3-carboxylate (5.69 g, 33 mmol) in ether (20 ml) was added dropwise to a stirred solution of lithium aluminium hydride (36.6 ml of a 1M solution in THF, 36.6 mmol) in ether (85 ml) cooled to maintain a reaction temperature of 20° C. The mixture was stirred for 1.5 hours at amb... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1CC[NH]CC1 | HO- | CCOCC.C1CCOC1 | 20 | 1.5 | CCOC(=O)[C@@H]1CCCN(C)C1>CCOCC.C1CCOC1>CN1CCC[C@@H](CO)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-953ee293a6614f7c84aa8f7936ea4c3a | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1O.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>CN1CCCC(CO)C1.CN1CCC[C@@H](CO)C1 | ClC1=CC(=C(OC2=NC=NC3=CC(=C(C=C23)OC)O)C=C1)F.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>CN1CC(CCC1)CO.CN1C[C@@H](CCC1)CO | Fc1cc(Cl)ccc1O[c:16]1[n:2][cH:10][n:11][c:14]2[cH:9][c:6]([OH:17])[c:7]([O:8][CH3:1])[cH:18][c:15]21.c1ccc(P(c2cc[cH:12][cH:13]c2)c2cc[cH:3][cH:4][cH:5]2)cc1>>[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][CH:6]([CH2:7][OH:8])[CH2:9]1.[CH3:10][N:11]1[CH2:12][CH2:13][CH2:14][C@@H:15]([CH2:16][OH:17])[CH2:18]1 | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1O.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | CN1CCCC(CO)C1.CN1CCC[C@@H](CO)C1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | OtherReaction | b8c593b8a7987448fb9f49e9e1dc564e9d8d35ddf43c6096f8f47b89bcde483e | 14ad35e74b335fe2dbf329950ee580105f2b6b3ea5bdb6d5c86b06fec4f8886a | C1CCNCC1.C1CCNCC1 | Cl-c1:c:c:c(-O-[c;H0;D3;+0:1]2:[n;H0;D2;+0:2]:[cH;D2;+0:3]:[n;H0;D2;+0:4]:[c;H0;D3;+0:5]3:[cH;D2;+0:6]:[c;H0;D3;+0:7](-[OH;D1;+0:8]):[c;H0;D3;+0:9](-[O;H0;D2;+0:10]-[CH3;D1;+0:11]):[cH;D2;+0:12]:[c;H0;D3;+0:13]:3:2):c(-F):c:1.[cH;D2;+0:14]1:[cH;D2;+0:15]:c:c(-P(-c2:[cH;D2;+0:16]:[cH;D2;+0:17]:[cH;D2;+0:18]:c:c:2)-c2:c:... | null | [] | null | null | 30 | MINUTE | 4-(4-Chloro-2-fluorophenoxy)-7-hydroxy-6-methoxyquinazoline (12.1 g, 38 mmol), (prepared as described for the starting material in Example 5), was suspended in dichloromethane (375 ml) and treated with triphenylphosphine (29.6 g, 113 mmol) then stirred at ambient temperature for 30 minutes. (1-Methylpiperidin-3-yl)meth... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ether.Ether.Aromatic alcohol | Primary alcohol.Primary alcohol.Tertiary amine.Tertiary amine | c1ccccc1.c1ccc2ncncc2c1.c1ccccc1.c1ccccc1.c1ccccc1 | C1CC[NH]CC1.C1CC[NH]CC1 | C1CC[NH]CC1.C1CC[NH]CC1 | Other | ClCCl | null | 0.5 | COc1cc2c(Oc3ccc(Cl)cc3F)ncnc2cc1O.c1ccc(P(c2ccccc2)c2ccccc2)cc1>ClCCl>CN1CCCC(CO)C1.CN1CCC[C@@H](CO)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-468c8a1ab0824fd196d274cd310a5cf7 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Cc1cc2cc(O)ccc2[nH]1>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCCN1CCCC1 | O.ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1.OC=1C=C2C=C(NC2=CC1)C.C([O-])([O-])=O.[K+].[K+]>>COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCC1)OC=1C=C2C=C(NC2=CC1)C | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:23]([O:24][CH2:25][CH2:26][CH2:27][N:28]3[CH2:29][CH2:30][CH2:31][CH2:32]3)[cH:22][c:21]2[n:20][cH:19][n:18]1.[OH:7][c:8]1[cH:9][cH:10][c:11]2[nH:12][c:13]([CH3:14])[cH:15][c:16]2[cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][c:13]([CH3:14]... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Cc1cc2cc(O)ccc2[nH]1 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCCN1CCCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCCCN3CCCC3)cc2n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[O;H0;D2;+0:9]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 46.2 | [{"value": 46.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCC1)OC=1C=C2C=C(NC2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.2, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCC1)OC=1C=C2C=C(NC2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 2 | HOUR | A suspension of 4-chloro-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline (0.13 g, 0.4 mmol), 5-hydroxy-2-methylindole (74 mg, 0.5 mmol) and potassium carbonate (83 mg, 0.6 mmol) in DMF (1.5 ml) was stirred at 100° C. for 2 hours. After cooling to ambient temperature, water (20 ml) was added. The precipitate was col... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]C1 | HCl | CN(C)C=O | 100 | 2 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Cc1cc2cc(O)ccc2[nH]1>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCCCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e3d1096b942a4a54904d797e6ac7b158 | COc1cc(C(=O)O)ccc1O.ClCCCN1CCCC1>>COc1cc(C(=O)O)ccc1OCCCN1CCCC1.Cl | OC1=C(C=C(C(=O)O)C=C1)OC.N1(CCCC1)CCCCl.C([O-])([O-])=O.[K+].[K+].[I-].[K+]>>Cl.COC=1C=C(C(=O)O)C=CC1OCCCN1CCCC1 | [CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[OH:8])[cH:9][cH:10][c:11]1[OH:12].[CH2:13]([CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][CH2:19][CH2:20]1)[Cl:21]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[OH:8])[cH:9][cH:10][c:11]1[O:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][CH2:19][CH2:20]1.[ClH:21] | COc1cc(C(=O)O)ccc1O.ClCCCN1CCCC1 | COc1cc(C(=O)O)ccc1OCCCN1CCCC1.Cl | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(OCCCN2CCCC2)cc1 | [C:1]-[C:2]-[CH2;D2;+0:3]-[Cl;H0;D1;+0:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8].[ClH;D0;+0:4] | 77.3 | [{"value": 77.0, "product": "Cl.COC=1C=C(C(=O)O)C=CC1OCCCN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.3, "product": "Cl.COC=1C=C(C(=O)O)C=CC1OCCCN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A mixture of 4-hydroxy-3-methoxybenzoic acid (8.4 g, 50 mmol), 3-(pyrrolidin-1-yl)propyl chloride (14.75 g, 0.1 mol), (J. Am. Chem. Soc. 1955, 77, 2272), potassium carbonate (13.8 g, 0.1 mol) and potassium iodide (1.66 g, 10 mmol) in DMF (150 ml) was stirred and heated at 100° C. for 3 hours. The mixture was allowed to... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.C1CC[NH]C1 | null | CN(C)C=O | 100 | null | COc1cc(C(=O)O)ccc1O.ClCCCN1CCCC1>CN(C)C=O>COc1cc(C(=O)O)ccc1OCCCN1CCCC1.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c78eec71e77643b88860c1c2db4a5eee | COc1cc(C(=O)O)ccc1OCCCN1CCCC1.O=[N+]([O-])O>>COc1cc(C(=O)O)c([N+](=O)[O-])cc1OCCCN1CCCC1 | [N+](=O)(O)[O-].Cl.COC=1C=C(C(=O)O)C=CC1OCCCN1CCCC1>>Cl.COC=1C(=CC(=C(C(=O)O)C1)[N+](=O)[O-])OCCCN1CCCC1 | [CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[OH:8])[cH:9][cH:13][c:14]1[O:15][CH2:16][CH2:17][CH2:18][N:19]1[CH2:20][CH2:21][CH2:22][CH2:23]1.O[N+:10](=[O:11])[O-:12]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[OH:8])[c:9]([N+:10](=[O:11])[O-:12])[cH:13][c:14]1[O:15][CH2:16][CH2:17][CH2:18][N:19]1[CH2:20][CH2:21][CH2:2... | COc1cc(C(=O)O)ccc1OCCCN1CCCC1.O=[N+]([O-])O | COc1cc(C(=O)O)c([N+](=O)[O-])cc1OCCCN1CCCC1 | null | null | C(=O)(C(F)(F)F)O | Functional Group Addition | Aromatic nitration with HNO3 | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccc(OCCCN2CCCC2)cc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[O;D1;H0:4]=[C:5](-[O;D1;H1:6])-[c:7](:[c:8]):[cH;D2;+0:9]:[c:10]:[c:11]>>[O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:7](-[C:5](=[O;D1;H0:4])-[O;D1;H1:6]):[c:8] | 90 | [{"value": 90.0, "product": "Cl.COC=1C(=CC(=C(C(=O)O)C1)[N+](=O)[O-])OCCCN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.9, "product": "Cl.COC=1C(=CC(=C(C(=O)O)C1)[N+](=O)[O-])OCCCN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Fuming nitric acid (2.4 ml, 57.9 mmol) was added slowly at 0° C. to a solution of 3-methoxy-4-(3-(pyrrolidin-1-yl)propoxy)benzoic acid hydrochloride (12.15 g, 38.17 mmol) in TFA (40 ml). The cooling bath was removed and the reaction mixture stirred at ambient temperature for 1 hour. The TFA was removed by evaporation a... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CC[NH]C1 | HO- | C(=O)(C(F)(F)F)O | null | 1 | COc1cc(C(=O)O)ccc1OCCCN1CCCC1.O=[N+]([O-])O>C(=O)(C(F)(F)F)O>COc1cc(C(=O)O)c([N+](=O)[O-])cc1OCCCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9f93506979e14002b2e5ba7689e3e458 | COc1cc(C(=O)O)c([N+](=O)[O-])cc1OCCCN1CCCC1>>COc1cc(C(N)=O)c([N+](=O)[O-])cc1OCCCN1CCCC1 | Cl.COC=1C(=CC(=C(C(=O)O)C1)[N+](=O)[O-])OCCCN1CCCC1.CN(C)C=O>>COC=1C(=CC(=C(C(=O)N)C1)[N+](=O)[O-])OCCCN1CCCC1 | O[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:14]([O:15][CH2:16][CH2:17][CH2:18][N:19]2[CH2:20][CH2:21][CH2:22][CH2:23]2)[cH:13][c:9]1[N+:10](=[O:11])[O-:12])=[O:8]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]([NH2:7])=[O:8])[c:9]([N+:10](=[O:11])[O-:12])[cH:13][c:14]1[O:15][CH2:16][CH2:17][CH2:18][N:19]1[CH2:20][CH2:21][CH2:22][CH... | COc1cc(C(=O)O)c([N+](=O)[O-])cc1OCCCN1CCCC1 | COc1cc(C(N)=O)c([N+](=O)[O-])cc1OCCCN1CCCC1 | null | null | S(=O)(Cl)Cl | Functional Group Interconversion | OtherReaction | e1b1a1f71ee10336b9e90a021457b106dbfe08a22161aaad6804675a8134a46f | 5d384be3554a01fd49be5eb779c3b10075a4cc9a2373eb20aaa867286d4e28a9 | c1ccc(OCCCN2CCCC2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]>>[N;D1;H2:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 73 | [{"value": 73.0, "product": "COC=1C(=CC(=C(C(=O)N)C1)[N+](=O)[O-])OCCCN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | A solution of 5-methoxy-2-nitro-4-(3-(pyrrolidin-1-yl)propoxy)benzoic acid hydrochloride (9.63 g, 24 mmol) in thionyl chloride (20 ml) and DMF (50 μl) was heated at 45° C. for 1.5 hours. The excess thionyl chloride was removed by evaporation and by azeotroping with toluene (×2). The resulting solid was suspended in THF... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | c1ccccc1.C1CC[NH]C1 | null | S(=O)(Cl)Cl | null | 1.5 | COc1cc(C(=O)O)c([N+](=O)[O-])cc1OCCCN1CCCC1>S(=O)(Cl)Cl>COc1cc(C(N)=O)c([N+](=O)[O-])cc1OCCCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-65c85e4819d640f5a613400a453478e4 | COc1cc(C(N)=O)c([N+](=O)[O-])cc1OCCCN1CCCC1>>COc1cc(C(N)=O)c(N)cc1OCCCN1CCCC1 | Cl.COC=1C(=CC(=C(C(=O)N)C1)[N+](=O)[O-])OCCCN1CCCC1>>Cl.NC1=C(C(=O)N)C=C(C(=C1)OCCCN1CCCC1)OC | O=[N+:10]([O-])[c:9]1[c:5]([C:6]([NH2:7])=[O:8])[cH:4][c:3]([O:2][CH3:1])[c:12]([O:13][CH2:14][CH2:15][CH2:16][N:17]2[CH2:18][CH2:19][CH2:20][CH2:21]2)[cH:11]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]([NH2:7])=[O:8])[c:9]([NH2:10])[cH:11][c:12]1[O:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:18][CH2:19][CH2:20][CH2:21]1 | COc1cc(C(N)=O)c([N+](=O)[O-])cc1OCCCN1CCCC1 | COc1cc(C(N)=O)c(N)cc1OCCCN1CCCC1 | null | [Fe] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(OCCCN2CCCC2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]-[C:5](-[N;D1;H2:6])=[O;D1;H0:7]>>[N;D1;H2:6]-[C:5](=[O;D1;H0:7])-[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | 85 | [{"value": 85.0, "product": "Cl.NC1=C(C(=O)N)C=C(C(=C1)OCCCN1CCCC1)OC", "details": "PERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | Concentrated hydrochloric acid (5 ml) was added to a suspension of 5-methoxy-2-nitro-4-(3-(pyrrolidin-1-yl)propoxy)benzamide (1.5 g, 4.64 mmol) in methanol (20 ml) and the mixture was heated at 50° C. to give a solution. Iron powder (1.3 g, 23.2 mmol) was added in portions and the reaction mixture was then heated at re... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.C1CC[NH]C1 | Other | [Fe].CO | 50 | null | COc1cc(C(N)=O)c([N+](=O)[O-])cc1OCCCN1CCCC1>[Fe].CO>COc1cc(C(N)=O)c(N)cc1OCCCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e8213d2577f9480c993b2fc592165aac | COc1cc(C(N)=O)c(N)cc1OCCCN1CCCC1>>COc1cc2c(O)ncnc2cc1OCCCN1CCCC1 | Cl.NC1=C(C(=O)N)C=C(C(=C1)OCCCN1CCCC1)OC.CN(C)C=NC=[N+](C)C.[Cl-].C(C)(=O)O.C(C)(=O)[O-].[Na+]>>OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1 | [CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[NH2:8])[c:11]([NH2:10])[cH:12][c:13]1[O:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][CH2:21][CH2:22]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([OH:7])[n:8][cH:9][n:10][c:11]2[cH:12][c:13]1[O:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][CH2:21][CH2:22]1 | COc1cc(C(N)=O)c(N)cc1OCCCN1CCCC1 | COc1cc2c(O)ncnc2cc1OCCCN1CCCC1 | null | null | O1CCOCC1 | Aromatic Heterocycle Formation | OtherReaction | 0a83a7d1eeda533da1fe0ab49b40addde9a79d36d3b4681a7c25cbc84aae3632 | c7f1baf6d039a31bf559cfdf0b5118c8ff66e7eb348eec43bb09814b0890990b | c1ncc2ccc(OCCCN3CCCC3)cc2n1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4](-[C;H0;D3;+0:5](-[NH2;D1;+0:6])=[O;H0;D1;+0:7]):[c:8]>>[OH;D1;+0:7]-[c;H0;D3;+0:5]1:[n;H0;D2;+0:6]:[c:9]:[n;H0;D2;+0:1]:[c:2](:[c:3]):[c:4]:1:[c:8] | 92.6 | [{"value": 83.0, "product": "OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.6, "product": "OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-amino-5-methoxy-4-(3-(pyrrolidin-1-yl)propoxy)benzamide hydrochloride (5.92 g, 16.2 mmol) and Gold's reagent (3.5 g, 21.4 mmol) in dioxane (50 ml) was heated at reflux for 5 hours. Acetic acid (0.7 ml) and sodium acetate (1.33 g) were added to the reaction mixture which was heated at reflux for a further... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Primary amine | Aromatic alcohol | c1ccccc1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1CC[NH]C1 | Other | O1CCOCC1 | null | null | COc1cc(C(N)=O)c(N)cc1OCCCN1CCCC1>O1CCOCC1>COc1cc2c(O)ncnc2cc1OCCCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f0abda1a6a304b70a4c0bcb58c3af872 | COc1cc2c(O)ncnc2cc1OCCCN1CCCC1.O=S(Cl)Cl>>COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1 | OC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1.S(=O)(Cl)Cl>>ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1 | O[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:13]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:19][CH2:20][CH2:21][CH2:22]3)[cH:12][c:11]2[n:10][cH:9][n:8]1.O=S(Cl)[Cl:7]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([Cl:7])[n:8][cH:9][n:10][c:11]2[cH:12][c:13]1[O:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][CH2:21][CH2:22]1 | COc1cc2c(O)ncnc2cc1OCCCN1CCCC1.O=S(Cl)Cl | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1 | null | null | CN(C)C=O | Functional Group Interconversion | Alcohol to chloride_SOCl2 | b0b0f8b7642d018e3b261231985ddd65d16d4d42cce7aa11791e49c826337b90 | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1ncc2ccc(OCCCN3CCCC3)cc2n1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9] | null | [] | null | null | null | null | A mixture of 4-hydroxy-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline (1.7 g, 5 mmol) and thionyl chloride (25 ml) containing DMF (0.2 ml) was heated at reflux for 3 hours. Excess thionyl chloride was removed by evaporation and by azeotroping with toluene (×2). The residue was suspended in ether and 10% aqueous so... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1CC[NH]C1 | HCl | CN(C)C=O | null | null | COc1cc2c(O)ncnc2cc1OCCCN1CCCC1.O=S(Cl)Cl>CN(C)C=O>COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-86f4f72f75ec49408153ebc85b29e367 | CC(C)(C)OC(=O)N1CCC(CO)CC1.Cc1ccccc1S(=O)(=O)Cl>>Cc1ccc(S(=O)(=O)OCC2CCN(C(=O)OC(C)(C)C)CC2)cc1 | C=1(C(=CC=CC1)S(=O)(=O)Cl)C.OCC1CCN(CC1)C(=O)OC(C)(C)C.N12CCN(CC1)CC2>>CC1=CC=C(C=C1)S(=O)(=O)OCC1CCN(CC1)C(=O)OC(C)(C)C | [OH:9][CH2:10][CH:11]1[CH2:12][CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22][CH2:23]1.Cl[S:6]([c:5]1[c:2]([CH3:1])[cH:3][cH:4][cH:25][cH:24]1)(=[O:7])=[O:8]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[O:9][CH2:10][CH:11]2[CH2:12][CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:... | CC(C)(C)OC(=O)N1CCC(CO)CC1.Cc1ccccc1S(=O)(=O)Cl | Cc1ccc(S(=O)(=O)OCC2CCN(C(=O)OC(C)(C)C)CC2)cc1 | null | null | CCOCC.COC(C)(C)C | Acylation | OtherReaction | 6dd26378b7c569e7e73da2c430efcb9bc58014e30edce94cf052e575133a80c4 | 436a9e21ae4d378d7049998650bf5bf959f4c8094cc386d78e7e073ba98e619a | O=S(=O)(OCC1CCNCC1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c;H0;D3;+0:4]1:[c:5]:[cH;D2;+0:6]:[cH;D2;+0:7]:[c:8]:[c;H0;D3;+0:9]:1-[C;D1;H3:10].[C:11]-[C:12]-[OH;D1;+0:13]>>[C:11]-[C:12]-[O;H0;D2;+0:13]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c;H0;D3;+0:4]1:[c:5]:[cH;D2;+0:6]:[c;H0;D3;+0:9](-[C;D1;H3:10]):[c:8]:[cH;D2;+0:7]:1 | 62,906.5 | [{"value": 85.0, "product": "CC1=CC=C(C=C1)S(=O)(=O)OCC1CCN(CC1)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62906.5, "product": "CC1=CC=C(C=C1)S(=O)(=O)OCC1CCN(CC1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a solution of 4-hydroxymethyl-1-tert-butyloxycarbonylpiperidine (52.5 g, 0.244 mol) in tert-butyl methyl ether (525 ml) was added 1,4-diazabicyclo[2.2.2]octane (42.4 g, 0.378 mol). After stirring for 15 minutes at ambient temperature, the mixture was cooled to 5° C. and a solution of toluene sulphonyl chloride (62.8... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Tosylate | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CC[NH]CC1 | HCl | CCOCC.COC(C)(C)C | null | 0.25 | CC(C)(C)OC(=O)N1CCC(CO)CC1.Cc1ccccc1S(=O)(=O)Cl>CCOCC.COC(C)(C)C>Cc1ccc(S(=O)(=O)OCC2CCN(C(=O)OC(C)(C)C)CC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fd0a40d6fd0f4a0fa3e2bcf016c3a5a1 | CCOC(=O)c1ccc(O)c(OC)c1.Cc1ccc(S(=O)(=O)OCC2CCN(C(=O)OC(C)(C)C)CC2)cc1>>CCOC(=O)c1ccc(OCC2CCN(C(=O)OC(C)(C)C)CC2)c(OC)c1 | COC=1C=C(C(=O)OCC)C=CC1O.C([O-])([O-])=O.[K+].[K+].CC1=CC=C(C=C1)S(=O)(=O)OCC1CCN(CC1)C(=O)OC(C)(C)C>>COC=1C=C(C(=O)OCC)C=CC1OCC1CCN(CC1)C(=O)OC(C)(C)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([OH:10])[c:25]([O:26][CH3:27])[cH:28]1.Cc1ccc(S(=O)(=O)O[CH2:11][CH:12]2[CH2:13][CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][CH2:24]2)cc1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][CH:12]2[CH2:13][CH2... | CCOC(=O)c1ccc(O)c(OC)c1.Cc1ccc(S(=O)(=O)OCC2CCN(C(=O)OC(C)(C)C)CC2)cc1 | CCOC(=O)c1ccc(OCC2CCN(C(=O)OC(C)(C)C)CC2)c(OC)c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | b5213736859cf91483a02f350869986d9b7674724716adef8a5d7a4bbdb79574 | 3d107e624e135e10014c7bf413dd0be27e1e4488f039e545b94cb1680b764158 | c1ccc(OCC2CCNCC2)cc1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4]):c:c:1.[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:3]-[C:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8])-[C:4] | 89 | [{"value": 89.0, "product": "COC=1C=C(C(=O)OCC)C=CC1OCC1CCN(CC1)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.0, "product": "COC=1C=C(C(=O)OCC)C=CC1OCC1CCN(CC1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | 2.5 | HOUR | To a suspension of ethyl 3-methoxy-4-hydroxybenzoate (19.6 g, 0.1 mol) and potassium carbonate (28 g, 0.2 mol) in dry DMF (200 ml) was added 4-(4-methylphenylsulphonyloxymethyl)-1-tert-butyloxycarbonylpiperidine (40 g, 0.11 mol). After stirring at 95° C. for 2.5 hours, the mixture was cooled to ambient temperature and ... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Aromatic alcohol | Ether | c1ccccc1 | null | c1ccccc1.C1CC[NH]CC1 | TsOH.HO- | CN(C)C=O | 95 | 2.5 | CCOC(=O)c1ccc(O)c(OC)c1.Cc1ccc(S(=O)(=O)OCC2CCN(C(=O)OC(C)(C)C)CC2)cc1>CN(C)C=O>CCOC(=O)c1ccc(OCC2CCN(C(=O)OC(C)(C)C)CC2)c(OC)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0d70b38b1805414687e476e36009fc18 | CCOC(=O)c1ccc(OCC2CCN(C(=O)OC(C)(C)C)CC2)c(OC)c1>>CCOC(=O)c1ccc(OCC2CCN(C)CC2)c(OC)c1 | Cl.CCOCC.COC=1C=C(C(=O)OCC)C=CC1OCC1CCN(CC1)C(=O)OC(C)(C)C.C=O>>COC=1C=C(C(=O)OCC)C=CC1OCC1CCN(CC1)C | CC(C)(C)O[C:16](=O)[N:15]1[CH2:14][CH2:13][CH:12]([CH2:11][O:10][c:9]2[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:22][c:19]2[O:20][CH3:21])[CH2:18][CH2:17]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][CH:12]2[CH2:13][CH2:14][N:15]([CH3:16])[CH2:17][CH2:18]2)[c:19]([O:20][CH3:21])[... | CCOC(=O)c1ccc(OCC2CCN(C(=O)OC(C)(C)C)CC2)c(OC)c1 | CCOC(=O)c1ccc(OCC2CCN(C)CC2)c(OC)c1 | null | null | C(=O)O | Reduction | OtherReaction | dcda46d15ef9f01c1f93228fbde5fe507f031b166ebcdcda0b018d3445dde9e4 | 414023a339cb5e5ca20834c6434c67bcea724431433bac28293e7fcfb67a2a9e | c1ccc(OCC2CCNCC2)cc1 | C-C(-C)(-C)-O-[C;H0;D3;+0:1](=O)-[#7:2](-[C:3])-[C:4]>>[C:3]-[#7:2](-[CH3;D1;+0:1])-[C:4] | 111.9 | [{"value": 111.9, "product": "COC=1C=C(C(=O)OCC)C=CC1OCC1CCN(CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | 3 | HOUR | To a solution of ethyl 3-methoxy-4-(1-tert-butyloxycarbonylpiperidin-4-ylmethoxy)benzoate (35 g, 89 mmol) in formic acid (35 ml) was added formaldehyde (12M, 37% in water, 35 ml, 420 mmol). After stirring at 95° C. for 3 hours, the volatiles were removed by evaporation. The residue was dissolved in methylene chloride a... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | null | null | null | c1ccccc1.C1CC[NH]CC1 | HO- | C(=O)O | 95 | 3 | CCOC(=O)c1ccc(OCC2CCN(C(=O)OC(C)(C)C)CC2)c(OC)c1>C(=O)O>CCOC(=O)c1ccc(OCC2CCN(C)CC2)c(OC)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5db72145fc924655aa52ca487a293c36 | CCOC(=O)c1ccc(OCC2CCN(C)CC2)c(OC)c1.O=[N+]([O-])O>>CCOC(=O)c1cc(OC)c(OCC2CCN(C)CC2)cc1[N+](=O)[O-] | COC=1C=C(C(=O)OCC)C=CC1OCC1CCN(CC1)C.C(=O)(C(F)(F)F)O.[N+](=O)(O)[O-]>>COC=1C=C(C(=O)OCC)C(=CC1OCC1CCN(CC1)C)[N+](=O)[O-] | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([O:9][CH3:10])[c:11]([O:12][CH2:13][CH:14]2[CH2:15][CH2:16][N:17]([CH3:18])[CH2:19][CH2:20]2)[cH:21][cH:22]1.O[N+:23](=[O:24])[O-:25]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([O:9][CH3:10])[c:11]([O:12][CH2:13][CH:14]2[CH2:15][CH2:16][N:17]([CH3:18])[CH2:19][C... | CCOC(=O)c1ccc(OCC2CCN(C)CC2)c(OC)c1.O=[N+]([O-])O | CCOC(=O)c1cc(OC)c(OCC2CCN(C)CC2)cc1[N+](=O)[O-] | null | null | C(Cl)Cl | Functional Group Addition | Aromatic nitration with HNO3 | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccc(OCC2CCNCC2)cc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12]>>[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c;H0;D3;+0:10](-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3]):[c:11]:[c:12] | 90.6 | [{"value": 82.0, "product": "COC=1C=C(C(=O)OCC)C(=CC1OCC1CCN(CC1)C)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.6, "product": "COC=1C=C(C(=O)OCC)C(=CC1OCC1CCN(CC1)C)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of ethyl 3-methoxy-4-(1-methylpiperidin-4-ylmethoxy)benzoate (30.6 g, 89 mmol) in methylene chloride (75 ml) was cooled to 0–5° C. TFA (37.5 ml) was added followed by the dropwise addition over 15 minutes of a solution of fuming 24M nitric acid (7.42 ml, 178 mmol) in methylene chloride (15 ml). After complet... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CC[NH]CC1 | HO- | C(Cl)Cl | null | 2 | CCOC(=O)c1ccc(OCC2CCN(C)CC2)c(OC)c1.O=[N+]([O-])O>C(Cl)Cl>CCOC(=O)c1cc(OC)c(OCC2CCN(C)CC2)cc1[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d82fc98a94e14acc8e1f82ee567bacfc | CCOC(=O)c1cc(OC)c(OCC2CCN(C)CC2)cc1[N+](=O)[O-]>>CCOC(=O)c1cc(OC)c(OCC2CCN(C)CC2)cc1N | COC=1C=C(C(=O)OCC)C(=CC1OCC1CCN(CC1)C)[N+](=O)[O-].[H][H]>>NC1=CC(=C(C=C1C(=O)OCC)OC)OCC1CCN(CC1)C | O=[N+:23]([O-])[c:22]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:7][c:8]([O:9][CH3:10])[c:11]([O:12][CH2:13][CH:14]2[CH2:15][CH2:16][N:17]([CH3:18])[CH2:19][CH2:20]2)[cH:21]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([O:9][CH3:10])[c:11]([O:12][CH2:13][CH:14]2[CH2:15][CH2:16][N:17]([CH3:18])[CH2:19][CH2:20]2)[... | CCOC(=O)c1cc(OC)c(OCC2CCN(C)CC2)cc1[N+](=O)[O-] | CCOC(=O)c1cc(OC)c(OCC2CCN(C)CC2)cc1N | null | [Pt] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(OCC2CCNCC2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]-[C:5](-[#8:6])=[O;D1;H0:7]>>[#8:6]-[C:5](=[O;D1;H0:7])-[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | 80 | [{"value": 80.0, "product": "NC1=CC(=C(C=C1C(=O)OCC)OC)OCC1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.0, "product": "NC1=CC(=C(C=C1C(=O)OCC)OC)OCC1CCN(CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of ethyl 3-methoxy-4-(1-methylpiperidin-4-ylmethoxy)-6-nitrobenzoate (3.89 g, 10 mmol) in methanol (80 ml) containing 10% platinum on activated carbon (50% wet) (389 mg) was hydrogenated at 1.8 atmospheres pressure until uptake of hydrogen ceased. The mixture was filtered and the filtrate was evaporated. T... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.C1CC[NH]CC1 | Other | [Pt].CO | null | null | CCOC(=O)c1cc(OC)c(OCC2CCN(C)CC2)cc1[N+](=O)[O-]>[Pt].CO>CCOC(=O)c1cc(OC)c(OCC2CCN(C)CC2)cc1N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1e7f1c8f0d364e399633d11e965d2672 | CCOC(=O)c1cc(OC)c(OCC2CCN(C)CC2)cc1N.N=CN>>COc1cc2c(=O)[nH]cnc2cc1OCC1CCN(C)CC1 | C(C)(=O)O.C(=N)N.NC1=CC(=C(C=C1C(=O)OCC)OC)OCC1CCN(CC1)C.C(C)(=O)O.C(=N)N>>COC=1C=C2C(NC=NC2=CC1OCC1CCN(CC1)C)=O | CCO[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:13]([O:14][CH2:15][CH:16]2[CH2:17][CH2:18][N:19]([CH3:20])[CH2:21][CH2:22]2)[cH:12][c:11]1[NH2:10])=[O:7].N[CH:9]=[NH:8]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6](=[O:7])[nH:8][cH:9][n:10][c:11]2[cH:12][c:13]1[O:14][CH2:15][CH:16]1[CH2:17][CH2:18][N:19]([CH3:20])[CH2:21][CH2:22]1 | CCOC(=O)c1cc(OC)c(OCC2CCN(C)CC2)cc1N.N=CN | COc1cc2c(=O)[nH]cnc2cc1OCC1CCN(C)CC1 | null | null | COCCO | Aromatic Heterocycle Formation | OtherReaction | 13c011143e351c3bbcd763cf1f04e086fd7ad2457d617cac850e1edc36b71aac | 36efa24579e0043fdba8918e78f1d75cb4504837c08d344d01203f5fa64bfaef | O=c1[nH]cnc2cc(OCC3CCNCC3)ccc12 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[NH2;D1;+0:6]):[c:7].N-[CH;D2;+0:8]=[NH;D1;+0:9]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[nH;D2;+0:9]:[cH;D2;+0:8]:[n;H0;D2;+0:6]:[c:5](:[c:7]):[c:3]:1:[c:4] | 83.7 | [{"value": 70.0, "product": "COC=1C=C2C(NC=NC2=CC1OCC1CCN(CC1)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.7, "product": "COC=1C=C2C(NC=NC2=CC1OCC1CCN(CC1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 115 | CELSIUS | 30 | MINUTE | A solution of ethyl 6-amino-3-methoxy-4-(1-methylpiperidin-4-ylmethoxy)benzoate (16.1 g, 50 mmol) in 2-methoxyethanol (160 ml) containing formamidine acetate (5.2 g, 50 mmol) was heated at 115° C. for 2 hours. Formamidine acetate (10.4 g, 100 mmol) was added in portions every 30 minutes during 4 hours. Heating was prol... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine.Primary amine | null | c1ccccc1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1CC[NH]CC1 | HO- | COCCO | 115 | 0.5 | CCOC(=O)c1cc(OC)c(OCC2CCN(C)CC2)cc1N.N=CN>COCCO>COc1cc2c(=O)[nH]cnc2cc1OCC1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2a8ee02ecab44445b12b1c97515591ac | COc1cc2c(=O)[nH]cnc2cc1OCC1CCN(C)CC1.O=S(Cl)Cl>>COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1 | COC=1C=C2C(NC=NC2=CC1OCC1CCN(CC1)C)=O.CN(C)C=O.S(=O)(Cl)Cl>>ClC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C | O=[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:13]([O:14][CH2:15][CH:16]3[CH2:17][CH2:18][N:19]([CH3:20])[CH2:21][CH2:22]3)[cH:12][c:11]2[n:10][cH:9][nH:8]1.O=S(Cl)[Cl:7]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([Cl:7])[n:8][cH:9][n:10][c:11]2[cH:12][c:13]1[O:14][CH2:15][CH:16]1[CH2:17][CH2:18][N:19]([CH3:20])[CH2:21][CH2:22]1 | COc1cc2c(=O)[nH]cnc2cc1OCC1CCN(C)CC1.O=S(Cl)Cl | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1 | null | null | null | Functional Group Interconversion | OtherReaction | 3788560e87eee8765e749543914a91a512631307b97fad163ebef894d2a0ea68 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ncc2ccc(OCC3CCNCC3)cc2n1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9] | 98 | [{"value": 98.0, "product": "ClC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | A solution of 6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)-3,4-dihydroquinazolin-4-one (2.8 g, 9.24 mmol) in thionyl chloride (28 ml) containing DMF (2801 μl) was refluxed at 85° C. for 1 hour. After cooling, the volatiles were removed by evaporation. The precipitate was triturated with ether, filtered, washed with et... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1CC[NH]CC1 | HCl | null | 85 | null | COc1cc2c(=O)[nH]cnc2cc1OCC1CCN(C)CC1.O=S(Cl)Cl>>COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c6abee09358844058b596e6adcde4f1a | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Cc1cc2cc(O)ccc2[nH]1>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCN(C)CC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C.OC=1C=C2C=C(NC2=CC1)C>>COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C)OC=1C=C2C=C(NC2=CC1)C | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:23]([O:24][CH2:25][CH:26]3[CH2:27][CH2:28][N:29]([CH3:30])[CH2:31][CH2:32]3)[cH:22][c:21]2[n:20][cH:19][n:18]1.[OH:7][c:8]1[cH:9][cH:10][c:11]2[nH:12][c:13]([CH3:14])[cH:15][c:16]2[cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[nH:12][c:13]([CH3:14... | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Cc1cc2cc(O)ccc2[nH]1 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCN(C)CC1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCC3CCNCC3)cc2n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[O;H0;D2;+0:9]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 79.2 | [{"value": 79.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C)OC=1C=C2C=C(NC2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.2, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C)OC=1C=C2C=C(NC2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using a procedure analogous to that described for Example 9, 4-chloro-6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazoline (0.13 g, 0.4 mmol), (prepared as described for the starting material in Example 10), was reacted with 5-hydroxy-2-methylindole (74 mg, 0.5 mol) to give 6-methoxy-4-(2-methylindol-5-yloxy)-7-((1... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]CC1 | HCl | null | null | null | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Cc1cc2cc(O)ccc2[nH]1>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e69b470660054ac7b140a6bbb2387121 | COc1cc2c(Cl)ncnc2cc1OCC1CCN(CCS(C)(=O)=O)CC1.Oc1ccc2cccnc2c1>>COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1OCC1CCN(CCS(C)(=O)=O)CC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)CCS(=O)(=O)C.OC1=CC=C2C=CC=NC2=C1.C([O-])([O-])=O.[K+].[K+]>>COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)CCS(=O)(=O)C)OC1=CC=C2C=CC=NC2=C1 | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:23]([O:24][CH2:25][CH:26]3[CH2:27][CH2:28][N:29]([CH2:30][CH2:31][S:32]([CH3:33])(=[O:34])=[O:35])[CH2:36][CH2:37]3)[cH:22][c:21]2[n:20][cH:19][n:18]1.[OH:7][c:8]1[cH:9][cH:10][c:11]2[cH:12][cH:13][cH:14][n:15][c:16]2[cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:... | COc1cc2c(Cl)ncnc2cc1OCC1CCN(CCS(C)(=O)=O)CC1.Oc1ccc2cccnc2c1 | COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1OCC1CCN(CCS(C)(=O)=O)CC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1cnc2cc(Oc3ncnc4cc(OCC5CCNCC5)ccc34)ccc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#7;a:9]:[c:10]:[c:11]:[c:12](-[OH;D1;+0:13]):[c:14]>>[#7;a:9]:[c:10]:[c:11]:[c:12](-[O;H0;D2;+0:13]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:14] | 76 | [{"value": 76.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)CCS(=O)(=O)C)OC1=CC=C2C=CC=NC2=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.2, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)CCS(=O)(=O)C)OC1=CC=C2C=CC=NC2=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 2 | HOUR | To a solution of 4-chloro-6-methoxy-7-((1-(2-methylsulphonylethyl)piperidin-4-yl)methoxy)quinazoline (115 mg, 0.28 mmol) and 7-hydroxyquinoline (50 mg, 0.33 mmol) in DMF (1.5 ml) was added potassium carbonate (60 mg, 0.42 mmol). The mixture was stirred for 2 hours at 100° C. After cooling, and removal of the volatiles ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncccc2c1.c1ccc2ncncc2c1.C1CC[NH]CC1 | HCl | CN(C)C=O | 100 | 2 | COc1cc2c(Cl)ncnc2cc1OCC1CCN(CCS(C)(=O)=O)CC1.Oc1ccc2cccnc2c1>CN(C)C=O>COc1cc2c(Oc3ccc4cccnc4c3)ncnc2cc1OCC1CCN(CCS(C)(=O)=O)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4c6833833a84432693784735392fb8a4 | CC(C)(C)C(=O)OCCl.COc1cc2c(=O)[nH]cnc2cc1OCc1ccccc1>>COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCc1ccccc1 | C(C(C)(C)C)(=O)OCCl.[H-].[Na+].C(C1=CC=CC=C1)OC1=C(C=C2C(NC=NC2=C1)=O)OC.Cl>>C(C1=CC=CC=C1)OC1=C(C=C2C(N(C=NC2=C1)COC(C(C)(C)C)=O)=O)OC | Cl[CH2:9][O:10][C:11](=[O:12])[C:13]([CH3:14])([CH3:15])[CH3:16].[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6](=[O:7])[nH:8][cH:17][n:18][c:19]2[cH:20][c:21]1[O:22][CH2:23][c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6](=[O:7])[n:8]([CH2:9][O:10][C:11](=[O:12])[C:13]([CH3:14])([CH3:15])[CH3:16])[... | CC(C)(C)C(=O)OCCl.COc1cc2c(=O)[nH]cnc2cc1OCc1ccccc1 | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCc1ccccc1 | null | null | CN(C)C=O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 3356b731e3fd312a1caad9e7f3379edf1f464b4ff06052540679496363168d0d | 6007d70cc3173f3039a472489995dad2781e8d749be1f1aa209b0bf2f190a4b4 | O=c1[nH]cnc2cc(OCc3ccccc3)ccc12 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3](-[C:4])=[O;D1;H0:5].[O;D1;H0:6]=[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[nH;D2;+0:12]:1>>[C:4]-[C:3](=[O;D1;H0:5])-[#8:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:12]1:[c:11]:[#7;a:10]:[c:9]:[c:8]:[c:7]:1=[O;D1;H0:6] | 84.1 | [{"value": 84.0, "product": "C(C1=CC=CC=C1)OC1=C(C=C2C(N(C=NC2=C1)COC(C(C)(C)C)=O)=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.1, "product": "C(C1=CC=CC=C1)OC1=C(C=C2C(N(C=NC2=C1)COC(C(C)(C)C)=O)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | Sodium hydride (1.44 g of a 60% suspension in mineral oil, 36 mmol) was added in portions over 20 minutes to a solution of 7-benzyloxy-6-methoxy-3,4-dihydroquinazolin-4-one (8.46 g, 30 mmol), (prepared as described for the starting material in Example 1), in DMF (70 ml) and the mixture was stirred for 1.5 hours. Chloro... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccccc1 | HCl | CN(C)C=O.C(C)(=O)OCC | null | 1.5 | CC(C)(C)C(=O)OCCl.COc1cc2c(=O)[nH]cnc2cc1OCc1ccccc1>CN(C)C=O.C(C)(=O)OCC>COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-105dd76d5f2344198beb01fbd2071e55 | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCc1ccccc1>>COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1O | C(C1=CC=CC=C1)OC1=C(C=C2C(N(C=NC2=C1)COC(C(C)(C)C)=O)=O)OC>>OC1=C(C=C2C(N(C=NC2=C1)COC(C(C)(C)C)=O)=O)OC | c1ccc(C[O:22][c:21]2[c:3]([O:2][CH3:1])[cH:4][c:5]3[c:6](=[O:7])[n:8]([CH2:9][O:10][C:11](=[O:12])[C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17][n:18][c:19]3[cH:20]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6](=[O:7])[n:8]([CH2:9][O:10][C:11](=[O:12])[C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17][n:18][c:19]2[cH:20][c:21]1[OH:22] | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCc1ccccc1 | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1O | null | [Pd] | CO.C(C)(=O)O.CN(C)C=O.C(C)(=O)OCC | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=c1[nH]cnc2ccccc12 | [#7;a:1]:[c:2]:[c:3]:[c:4](-[O;H0;D2;+0:5]-C-c1:c:c:c:c:c:1):[c:6]>>[#7;a:1]:[c:2]:[c:3]:[c:4](-[OH;D1;+0:5]):[c:6] | 80.4 | [{"value": 80.0, "product": "OC1=C(C=C2C(N(C=NC2=C1)COC(C(C)(C)C)=O)=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.4, "product": "OC1=C(C=C2C(N(C=NC2=C1)COC(C(C)(C)C)=O)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 40 | MINUTE | A mixture of 7-benzyloxy-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (7 g, 17.7 mmol) and 10% palladium-on-charcoal catalyst (700 mg) in ethyl acetate (250 ml), DMF (50 ml), methanol (50 ml) and acetic acid (0.7 ml) was stirred under hydrogen at atmospheric pressure for 40 minutes. The catalyst was re... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccc2ncncc2c1 | Other | [Pd].CO.C(C)(=O)O.CN(C)C=O.C(C)(=O)OCC | null | 0.666667 | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCc1ccccc1>[Pd].CO.C(C)(=O)O.CN(C)C=O.C(C)(=O)OCC>COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8ccda9cb1d66403782b1f8739af8d082 | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1O.Cc1ccc(S(=O)(=O)OCC2CCN(C(=O)OC(C)(C)C)CC2)cc1>>COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCC1CCN(C(=O)OC(C)(C)C)CC1 | OC1=C(C=C2C(N(C=NC2=C1)COC(C(C)(C)C)=O)=O)OC.CC1=CC=C(C=C1)S(=O)(=O)OCC1CCN(CC1)C(=O)OC(C)(C)C.Cl>>COC=1C=C2C(N(C=NC2=CC1OCC1CCN(CC1)C(=O)OC(C)(C)C)COC(C(C)(C)C)=O)=O | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6](=[O:7])[n:8]([CH2:9][O:10][C:11](=[O:12])[C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17][n:18][c:19]2[cH:20][c:21]1[OH:22].Cc1ccc(S(=O)(=O)O[CH2:23][CH:24]2[CH2:25][CH2:26][N:27]([C:28](=[O:29])[O:30][C:31]([CH3:32])([CH3:33])[CH3:34])[CH2:35][CH2:36]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[... | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1O.Cc1ccc(S(=O)(=O)OCC2CCN(C(=O)OC(C)(C)C)CC2)cc1 | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCC1CCN(C(=O)OC(C)(C)C)CC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | b5213736859cf91483a02f350869986d9b7674724716adef8a5d7a4bbdb79574 | 3d107e624e135e10014c7bf413dd0be27e1e4488f039e545b94cb1680b764158 | O=c1[nH]cnc2cc(OCC3CCNCC3)ccc12 | C-c1:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4]):c:c:1.[#7;a:5]:[c:6]:[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[#7;a:5]:[c:6]:[c:7]:[c:8](-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4]):[c:10] | 78.5 | [{"value": 78.5, "product": "COC=1C=C2C(N(C=NC2=CC1OCC1CCN(CC1)C(=O)OC(C)(C)C)COC(C(C)(C)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.4, "product": "COC=1C=C2C(N(C=NC2=CC1OCC1CCN(CC1)C(=O)OC(C)(C)C)COC(C(C)(C)C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A suspension of 7-hydroxy-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (6.12 g, 20 mmol) potassium carbonate (5.52 g, 40 mmol) in DMF (60 ml) was stirred at ambient temperature for 30 minutes. 4-(4-Methylphenylsulphonyloxymethyl)-1-tert-butyloxycarbonylpiperidine (8.86 g, 24 mmol), (prepared as describ... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Aromatic alcohol | Ether | c1ccccc1 | null | c1ccc2ncncc2c1.C1CC[NH]CC1 | TsOH.HO- | CN(C)C=O | null | 0.5 | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1O.Cc1ccc(S(=O)(=O)OCC2CCN(C(=O)OC(C)(C)C)CC2)cc1>CN(C)C=O>COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCC1CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-95eea2a3d9644b2091926b32c1b9b868 | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCC1CCN(C(=O)OC(C)(C)C)CC1>>COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCC1CCNCC1 | COC=1C=C2C(N(C=NC2=CC1OCC1CCN(CC1)C(=O)OC(C)(C)C)COC(C(C)(C)C)=O)=O.Cl.CCOCC>>Cl.COC=1C=C2C(N(C=NC2=CC1OCC1CCNCC1)COC(C(C)(C)C)=O)=O | CC(C)(C)OC(=O)[N:27]1[CH2:26][CH2:25][CH:24]([CH2:23][O:22][c:21]2[c:3]([O:2][CH3:1])[cH:4][c:5]3[c:6](=[O:7])[n:8]([CH2:9][O:10][C:11](=[O:12])[C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17][n:18][c:19]3[cH:20]2)[CH2:29][CH2:28]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6](=[O:7])[n:8]([CH2:9][O:10][C:11](=[O:12])[C:13]([CH3:14])... | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCC1CCN(C(=O)OC(C)(C)C)CC1 | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCC1CCNCC1 | null | null | C(C)(C)O.C(Cl)Cl | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=c1[nH]cnc2cc(OCC3CCNCC3)ccc12 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 100 | [{"value": 100.0, "product": "Cl.COC=1C=C2C(N(C=NC2=CC1OCC1CCNCC1)COC(C(C)(C)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 6-methoxy-3-((pivaloyloxy)methyl)-7-((1-tert-butyloxycarbonylpiperidin-4-yl)methoxy)-3,4-dihydroquinazolin-4-one (7.9 g, 16 mmol) in methylene chloride (80 ml) containing 5.5M hydrogen chloride in isopropanol (80 ml) was stirred for 1 hour at ambient temperature. Ether was added and the solid was collecte... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccc2ncncc2c1.C1CCNCC1 | HO- | C(C)(C)O.C(Cl)Cl | null | 1 | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCC1CCN(C(=O)OC(C)(C)C)CC1>C(C)(C)O.C(Cl)Cl>COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCC1CCNCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e3beac8f71b2485eb4b26f8397efafc2 | C=CS(C)(=O)=O.COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCC1CCNCC1>>COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCC1CCN(CCS(C)(=O)=O)CC1 | Cl.COC=1C=C2C(N(C=NC2=CC1OCC1CCNCC1)COC(C(C)(C)C)=O)=O.C(C)N(CC)CC.C([O-])([O-])=O.[K+].[K+].C(=C)S(=O)(=O)C>>COC=1C=C2C(N(C=NC2=CC1OCC1CCN(CC1)CCS(=O)(=O)C)COC(C(C)(C)C)=O)=O | [CH2:28]=[CH:29][S:30]([CH3:31])(=[O:32])=[O:33].[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6](=[O:7])[n:8]([CH2:9][O:10][C:11](=[O:12])[C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17][n:18][c:19]2[cH:20][c:21]1[O:22][CH2:23][CH:24]1[CH2:25][CH2:26][NH:27][CH2:34][CH2:35]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6](=[O:7])[n:8]([CH2:9][O:10... | C=CS(C)(=O)=O.COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCC1CCNCC1 | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCC1CCN(CCS(C)(=O)=O)CC1 | null | null | C(Cl)Cl.CO | Heteroatom Alkylation and Arylation | aza-Michael addition secondary | d3e8cc768c824777b70742851768dcb27bf5f461c310912ac3f5a7abd08f6975 | 828fcbb87adfef9f22c9a1e52b43c3df76cb2e49bfe62b57e8b79965772a2bed | O=c1[nH]cnc2cc(OCC3CCNCC3)ccc12 | [C;D1;H3:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[CH;D2;+0:5]=[CH2;D1;+0:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[CH2;D2;+0:6]-[CH2;D2;+0:5]-[#16:2](-[C;D1;H3:1])(=[O;D1;H0:3])=[O;D1;H0:4])-[C:10]-[C:11] | 54 | [{"value": 54.0, "product": "COC=1C=C2C(N(C=NC2=CC1OCC1CCN(CC1)CCS(=O)(=O)C)COC(C(C)(C)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.0, "product": "COC=1C=C2C(N(C=NC2=CC1OCC1CCN(CC1)CCS(=O)(=O)C)COC(C(C)(C)C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 6-methoxy-7-((piperidin-4-yl)methoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one hydrochloride (0.88 g, 2 mmol) and triethylamine (0.3 ml, 2.1 mmol) in methanol (10 ml) and methylene chloride (10 ml) was added potassium carbonate (280 mg, 2 mmol) and methyl vinyl sulfone (0.4 ml, 2.1 mmol). Af... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Vinyl | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccc2ncncc2c1.C1CC[NH]CC1 | null | C(Cl)Cl.CO | null | 2 | C=CS(C)(=O)=O.COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCC1CCNCC1>C(Cl)Cl.CO>COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCC1CCN(CCS(C)(=O)=O)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c855e264da9645dab49f60f7290300d3 | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCC1CCN(CCS(C)(=O)=O)CC1>>COc1cc2c(=O)[nH]cnc2cc1OCC1CCN(CCS(C)(=O)=O)CC1 | Cl.[OH-].[Na+].COC=1C=C2C(N(C=NC2=CC1OCC1CCN(CC1)CCS(=O)(=O)C)COC(C(C)(C)C)=O)=O.CC1=CC=C(C=C1)COC(=O)NNC(=O)C2=NC=CN=C2>>COC=1C=C2C(NC=NC2=CC1OCC1CCN(CC1)CCS(=O)(=O)C)=O | CC(C)(C)C(=O)OC[n:8]1[c:6](=[O:7])[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:13]([O:14][CH2:15][CH:16]3[CH2:17][CH2:18][N:19]([CH2:20][CH2:21][S:22]([CH3:23])(=[O:24])=[O:25])[CH2:26][CH2:27]3)[cH:12][c:11]2[n:10][cH:9]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6](=[O:7])[nH:8][cH:9][n:10][c:11]2[cH:12][c:13]1[O:14][CH2:15][CH:16]1[CH... | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCC1CCN(CCS(C)(=O)=O)CC1 | COc1cc2c(=O)[nH]cnc2cc1OCC1CCN(CCS(C)(=O)=O)CC1 | null | null | CO | Reduction | OtherReaction | 9f6991089c15fc054898797f1d3a42b158e517f125611bc103acfc00878b3b20 | b8e5da8ea19c403a2e974791a9cf591400749acb6b71151717aaece4f3b22bef | O=c1[nH]cnc2cc(OCC3CCNCC3)ccc12 | C-C(-C)(-C)-C(=O)-O-C-[n;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1=[O;D1;H0:7]>>[O;D1;H0:7]=[c:6]1:[c:5]:[c:4]:[#7;a:3]:[c:2]:[nH;D2;+0:1]:1 | 79 | [{"value": 79.0, "product": "COC=1C=C2C(NC=NC2=CC1OCC1CCN(CC1)CCS(=O)(=O)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.3, "product": "COC=1C=C2C(NC=NC2=CC1OCC1CCN(CC1)CCS(=O)(=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a suspension of 6-methoxy-7-((1-(2-methylsulphonylethyl)piperidin-4-yl)methoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (90 mg, 0.18 mmol) in methanol (3 ml) was added 2M aqueous sodium hydroxide (180 μl, 0.35 mmol). After stirring for 2 hours at ambient temperature, the mixture was adjusted to pH10 with... | 10.6084/m9.figshare.5104873.v1 | null | Ester | null | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1CC[NH]CC1 | HO- | CO | null | 2 | COc1cc2c(=O)n(COC(=O)C(C)(C)C)cnc2cc1OCC1CCN(CCS(C)(=O)=O)CC1>CO>COc1cc2c(=O)[nH]cnc2cc1OCC1CCN(CCS(C)(=O)=O)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f47b2f24d0d24ae8bfeb5a625660c16e | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Cc1ccnc2cc(O)ccc12>>COc1cc2c(Oc3ccc4c(C)ccnc4c3)ncnc2cc1OCC1CCN(C)CC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C.CC1=CC=NC2=CC(=CC=C12)O>>COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C)OC1=CC=C2C(=CC=NC2=C1)C | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:24]([O:25][CH2:26][CH:27]3[CH2:28][CH2:29][N:30]([CH3:31])[CH2:32][CH2:33]3)[cH:23][c:22]2[n:21][cH:20][n:19]1.[OH:7][c:8]1[cH:9][cH:10][c:11]2[c:12]([CH3:13])[cH:14][cH:15][n:16][c:17]2[cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[c:12]([CH3:13]... | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Cc1ccnc2cc(O)ccc12 | COc1cc2c(Oc3ccc4c(C)ccnc4c3)ncnc2cc1OCC1CCN(C)CC1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1cnc2cc(Oc3ncnc4cc(OCC5CCNCC5)ccc34)ccc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#7;a:9]:[c:10]:[c:11]:[c:12](-[OH;D1;+0:13]):[c:14]>>[#7;a:9]:[c:10]:[c:11]:[c:12](-[O;H0;D2;+0:13]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:14] | 90 | [{"value": 90.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C)OC1=CC=C2C(=CC=NC2=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C)OC1=CC=C2C(=CC=NC2=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using a procedure analogous to that described for Example 10, 4-chloro-6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazoline (130 mg, 0.4 mmol), (prepared as described for the starting material in Example 10), was reacted with 4-methyl-7-hydroxyquinoline (80 mg, 0.5 mol), (Chem. Ber. 1967, 100, 2077), to give 6-meth... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncccc2c1.c1ccc2ncncc2c1.C1CC[NH]CC1 | HCl | null | null | null | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Cc1ccnc2cc(O)ccc12>>COc1cc2c(Oc3ccc4c(C)ccnc4c3)ncnc2cc1OCC1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-00698d5f0e3b424b91f30a1c746a1b8d | COc1cc2c(Cl)ncnc2cc1OCC1CCN(CCS(C)(=O)=O)CC1.Cc1cc2cc(O)ccc2[nH]1>>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCN(CCS(C)(=O)=O)CC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)CCS(=O)(=O)C.OC=1C=C2C=C(NC2=CC1)C.C([O-])([O-])=O.[K+].[K+]>>COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)CCS(=O)(=O)C)OC=1C=C2C=C(NC2=CC1)C | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:23]([O:24][CH2:25][CH:26]3[CH2:27][CH2:28][N:29]([CH2:30][CH2:31][S:32]([CH3:33])(=[O:34])=[O:35])[CH2:36][CH2:37]3)[cH:22][c:21]2[n:20][cH:19][n:18]1.[OH:7][c:8]1[cH:9][cH:10][c:11]2[nH:12][c:13]([CH3:14])[cH:15][c:16]2[cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[... | COc1cc2c(Cl)ncnc2cc1OCC1CCN(CCS(C)(=O)=O)CC1.Cc1cc2cc(O)ccc2[nH]1 | COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCN(CCS(C)(=O)=O)CC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1nc(Oc2ccc3[nH]ccc3c2)c2ccc(OCC3CCNCC3)cc2n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[O;H0;D2;+0:9]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 41 | [{"value": 41.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)CCS(=O)(=O)C)OC=1C=C2C=C(NC2=CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.8, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)CCS(=O)(=O)C)OC=1C=C2C=C(NC2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 2 | HOUR | A solution of 4-chloro-6-methoxy-7-((1-(2-methylsulphonylethyl)piperidin-4-yl)methoxy)quinazoline (115 mg, 0.28 mmol), (prepared as described for the starting material in Example 12), 5-hydroxy-2-methylindole (50 mg, 0.33 mmol) and potassium carbonate (60 mg, 0.42 mmol) in DMF (1.5 ml) was stirred at 100° C. for 2 hour... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2[nH]ccc2c1.c1ccc2ncncc2c1.C1CC[NH]CC1 | HCl | CN(C)C=O | 100 | 2 | COc1cc2c(Cl)ncnc2cc1OCC1CCN(CCS(C)(=O)=O)CC1.Cc1cc2cc(O)ccc2[nH]1>CN(C)C=O>COc1cc2c(Oc3ccc4[nH]c(C)cc4c3)ncnc2cc1OCC1CCN(CCS(C)(=O)=O)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-01a9ce6cc8a944af8a778180893ea3e8 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Cc1ccnc2cc(O)ccc12>>COc1cc2c(Oc3ccc4c(C)ccnc4c3)ncnc2cc1OCCCN1CCCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1.OC1=CC=C2C(=CC=NC2=C1)C>>COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCC1)OC1=CC=C2C(=CC=NC2=C1)C | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:24]([O:25][CH2:26][CH2:27][CH2:28][N:29]3[CH2:30][CH2:31][CH2:32][CH2:33]3)[cH:23][c:22]2[n:21][cH:20][n:19]1.[OH:7][c:8]1[cH:9][cH:10][c:11]2[c:12]([CH3:13])[cH:14][cH:15][n:16][c:17]2[cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[c:12]([CH3:13])... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Cc1ccnc2cc(O)ccc12 | COc1cc2c(Oc3ccc4c(C)ccnc4c3)ncnc2cc1OCCCN1CCCC1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1cnc2cc(Oc3ncnc4cc(OCCCN5CCCC5)ccc34)ccc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#7;a:9]:[c:10]:[c:11]:[c:12](-[OH;D1;+0:13]):[c:14]>>[#7;a:9]:[c:10]:[c:11]:[c:12](-[O;H0;D2;+0:13]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:14] | 87.2 | [{"value": 87.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCC1)OC1=CC=C2C(=CC=NC2=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.2, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCC1)OC1=CC=C2C(=CC=NC2=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using a procedure analogous to that described for Example 9, 4-chloro-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline (0.13 g, 0.4 mmol), (prepared as described for the starting material in Example 9), was reacted with 7-hydroxy-4-methylquinoline (80 mg, 0.5 mol), (Chem. Berich. 1967, 100, 2077), to give 6-methoxy-... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncccc2c1.c1ccc2ncncc2c1.C1CC[NH]C1 | HCl | null | null | null | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.Cc1ccnc2cc(O)ccc12>>COc1cc2c(Oc3ccc4c(C)ccnc4c3)ncnc2cc1OCCCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7cc1b1fbb9924b418ed5c2868d74e86d | CC1=CC(C)(C)Nc2ccc(O)cc21.COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1>>COc1cc2c(Oc3ccc4c(c3)C(C)=CC(C)(C)N4)ncnc2cc1OCCCN1CCCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1.CC1(NC2=CC=C(C=C2C(=C1)C)O)C>>COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCC1)OC=1C=C2C(=CC(NC2=CC1)(C)C)C | [OH:7][c:8]1[cH:9][cH:10][c:11]2[c:12]([cH:13]1)[C:14]([CH3:15])=[CH:16][C:17]([CH3:18])([CH3:19])[NH:20]2.Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:26]([O:27][CH2:28][CH2:29][CH2:30][N:31]3[CH2:32][CH2:33][CH2:34][CH2:35]3)[cH:25][c:24]2[n:23][cH:22][n:21]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10]... | CC1=CC(C)(C)Nc2ccc(O)cc21.COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1 | COc1cc2c(Oc3ccc4c(c3)C(C)=CC(C)(C)N4)ncnc2cc1OCCCN1CCCC1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | C1=Cc2cc(Oc3ncnc4cc(OCCCN5CCCC5)ccc34)ccc2NC1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[O;H0;D2;+0:9]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 47.4 | [{"value": 47.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCC1)OC=1C=C2C(=CC(NC2=CC1)(C)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.4, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCC1)OC=1C=C2C(=CC(NC2=CC1)(C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using a procedure analogous to that described for Example 9, 4-chloro-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline (0.13 g, 0.4 mmol), (prepared as described for the starting material in Example 9), was reacted with 2,2,4-trimethyl-1,2-dihydroquinolin-6-ol (95 mg, 0.5 mmol), (IZV. ACAD. NAVK. SSSR. Ser. Khim. 19... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | C1=Cc2ccccc2NC1.c1ccc2ncncc2c1.C1CC[NH]C1 | HCl | null | null | null | CC1=CC(C)(C)Nc2ccc(O)cc21.COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1>>COc1cc2c(Oc3ccc4c(c3)C(C)=CC(C)(C)N4)ncnc2cc1OCCCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-04c6877b345344b1a4dc437ccebfe1b6 | CC1=CC(C)(C)Nc2ccc(O)cc21.COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1>>COc1cc2c(Oc3ccc4c(c3)C(C)=CC(C)(C)N4)ncnc2cc1OCC1CCN(C)CC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C.CC1(NC2=CC=C(C=C2C(=C1)C)O)C>>COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C)OC=1C=C2C(=CC(NC2=CC1)(C)C)C | [OH:7][c:8]1[cH:9][cH:10][c:11]2[c:12]([cH:13]1)[C:14]([CH3:15])=[CH:16][C:17]([CH3:18])([CH3:19])[NH:20]2.Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:26]([O:27][CH2:28][CH:29]3[CH2:30][CH2:31][N:32]([CH3:33])[CH2:34][CH2:35]3)[cH:25][c:24]2[n:23][cH:22][n:21]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10... | CC1=CC(C)(C)Nc2ccc(O)cc21.COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1 | COc1cc2c(Oc3ccc4c(c3)C(C)=CC(C)(C)N4)ncnc2cc1OCC1CCN(C)CC1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | C1=Cc2cc(Oc3ncnc4cc(OCC5CCNCC5)ccc34)ccc2NC1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[O;H0;D2;+0:9]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 74 | [{"value": 74.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C)OC=1C=C2C(=CC(NC2=CC1)(C)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.7, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C)OC=1C=C2C(=CC(NC2=CC1)(C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using a procedure analogous to that described for Example 9, 4-chloro-6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazoline (0.13 g, 0.4 mmol), (prepared as described for the starting material in Example 10), was reacted with 2,2,4-trimethyl-1,2-dihydroquinolin-6-ol (95 mg, 0.5 mmol), (IZV. ACAD. NAVK. SSSR. Ser. Kh... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | C1=Cc2ccccc2NC1.c1ccc2ncncc2c1.C1CC[NH]CC1 | HCl | null | null | null | CC1=CC(C)(C)Nc2ccc(O)cc21.COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1>>COc1cc2c(Oc3ccc4c(c3)C(C)=CC(C)(C)N4)ncnc2cc1OCC1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-03499002c4e144409125c00cc7f18366 | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Cc1cc(C)c2ccc(O)cc2n1>>COc1cc2c(Oc3ccc4c(C)cc(C)nc4c3)ncnc2cc1OCC1CCN(C)CC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C.CC1=NC2=CC(=CC=C2C(=C1)C)O>>CC1=NC2=CC(=CC=C2C(=C1)C)OC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:25]([O:26][CH2:27][CH:28]3[CH2:29][CH2:30][N:31]([CH3:32])[CH2:33][CH2:34]3)[cH:24][c:23]2[n:22][cH:21][n:20]1.[OH:7][c:8]1[cH:9][cH:10][c:11]2[c:12]([CH3:13])[cH:14][c:15]([CH3:16])[n:17][c:18]2[cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[c:12]... | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Cc1cc(C)c2ccc(O)cc2n1 | COc1cc2c(Oc3ccc4c(C)cc(C)nc4c3)ncnc2cc1OCC1CCN(C)CC1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1cnc2cc(Oc3ncnc4cc(OCC5CCNCC5)ccc34)ccc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#7;a:9]:[c:10]:[c:11]:[c:12](-[OH;D1;+0:13]):[c:14]>>[#7;a:9]:[c:10]:[c:11]:[c:12](-[O;H0;D2;+0:13]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:14] | 33.3 | [{"value": 33.0, "product": "CC1=NC2=CC(=CC=C2C(=C1)C)OC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 33.3, "product": "CC1=NC2=CC(=CC=C2C(=C1)C)OC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using a procedure analogous to that described for Example 9, 4-chloro-6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazoline (0.13 g, 0.4 mmol), (prepared as described for the starting material in Example 10), was reacted with 2,4-dimethyl-7-hydroxyquinoline (87 mg, 0.5 mmol), (Chem. Berichte, 1903, 36, 4016), to giv... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncccc2c1.c1ccc2ncncc2c1.C1CC[NH]CC1 | HCl | null | null | null | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Cc1cc(C)c2ccc(O)cc2n1>>COc1cc2c(Oc3ccc4c(C)cc(C)nc4c3)ncnc2cc1OCC1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5a514b9975c547d895e0fc229b7da49d | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.O=C1COc2ccc(O)cc2N1>>COc1cc2c(Oc3ccc4c(c3)NC(=O)CO4)ncnc2cc1OCC1CCN(C)CC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C.OC=1C=CC2=C(NC(CO2)=O)C1>>COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C)OC=1C=CC2=C(NC(CO2)=O)C1 | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:24]([O:25][CH2:26][CH:27]3[CH2:28][CH2:29][N:30]([CH3:31])[CH2:32][CH2:33]3)[cH:23][c:22]2[n:21][cH:20][n:19]1.[OH:7][c:8]1[cH:9][cH:10][c:11]2[c:12]([cH:13]1)[NH:14][C:15](=[O:16])[CH2:17][O:18]2>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[c:12]([cH:13... | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.O=C1COc2ccc(O)cc2N1 | COc1cc2c(Oc3ccc4c(c3)NC(=O)CO4)ncnc2cc1OCC1CCN(C)CC1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | O=C1COc2ccc(Oc3ncnc4cc(OCC5CCNCC5)ccc34)cc2N1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[O;H0;D2;+0:9]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 88 | [{"value": 88.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C)OC=1C=CC2=C(NC(CO2)=O)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.7, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C)OC=1C=CC2=C(NC(CO2)=O)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using a procedure analogous to that described for Example 9, 4-chloro-6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazoline (0.13 g, 0.4 mmol), (prepared as described for the starting material in Example 10), was reacted with 6-hydroxy-2H-4H-1,4-benzoxazin-3-one (83 mg, 0.5 mmol), (J. Chem. Soc. C, 1971, 2696), to g... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2c(c1)NCCO2.c1ccc2ncncc2c1.C1CC[NH]CC1 | HCl | null | null | null | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.O=C1COc2ccc(O)cc2N1>>COc1cc2c(Oc3ccc4c(c3)NC(=O)CO4)ncnc2cc1OCC1CCN(C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-45e1fb03180e465799ca19177569b4db | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.O=C1COc2ccc(O)cc2N1>>COc1cc2c(Oc3ccc4c(c3)NC(=O)CO4)ncnc2cc1OCCCN1CCCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCCC1.OC=1C=CC2=C(NC(CO2)=O)C1>>COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCC1)OC=1C=CC2=C(NC(CO2)=O)C1 | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:24]([O:25][CH2:26][CH2:27][CH2:28][N:29]3[CH2:30][CH2:31][CH2:32][CH2:33]3)[cH:23][c:22]2[n:21][cH:20][n:19]1.[OH:7][c:8]1[cH:9][cH:10][c:11]2[c:12]([cH:13]1)[NH:14][C:15](=[O:16])[CH2:17][O:18]2>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[c:12]([cH:13]... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.O=C1COc2ccc(O)cc2N1 | COc1cc2c(Oc3ccc4c(c3)NC(=O)CO4)ncnc2cc1OCCCN1CCCC1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | O=C1COc2ccc(Oc3ncnc4cc(OCCCN5CCCC5)ccc34)cc2N1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[O;H0;D2;+0:9]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 94.3 | [{"value": 94.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCC1)OC=1C=CC2=C(NC(CO2)=O)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.3, "product": "COC=1C=C2C(=NC=NC2=CC1OCCCN1CCCC1)OC=1C=CC2=C(NC(CO2)=O)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using a procedure analogous to that described for Example 9, 4-chloro-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline (0.13 g, 0.4 mmol), (prepared as described for the (starting material in Example 9), was reacted with 6-hydroxy-2H-4H-1,4-benzoxazin-3-one (83 mg, 0.5 mmol), (J. Chem. Soc. C, 1971, 2696), to give 6... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2c(c1)NCCO2.c1ccc2ncncc2c1.C1CC[NH]C1 | HCl | null | null | null | COc1cc2c(Cl)ncnc2cc1OCCCN1CCCC1.O=C1COc2ccc(O)cc2N1>>COc1cc2c(Oc3ccc4c(c3)NC(=O)CO4)ncnc2cc1OCCCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0529c424f3af499ab2e54e6225574c9a | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Oc1ccc2ncccc2c1>>COc1cc2c(Oc3ccc4ncccc4c3)ncnc2cc1OCC1CCN(C)CC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C.OC=1C=C2C=CC=NC2=CC1>>COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C)OC=1C=C2C=CC=NC2=CC1 | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:23]([O:24][CH2:25][CH:26]3[CH2:27][CH2:28][N:29]([CH3:30])[CH2:31][CH2:32]3)[cH:22][c:21]2[n:20][cH:19][n:18]1.[OH:7][c:8]1[cH:9][cH:10][c:11]2[n:12][cH:13][cH:14][cH:15][c:16]2[cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]4[n:12][cH:13][cH:14][cH:... | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Oc1ccc2ncccc2c1 | COc1cc2c(Oc3ccc4ncccc4c3)ncnc2cc1OCC1CCN(C)CC1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1cnc2ccc(Oc3ncnc4cc(OCC5CCNCC5)ccc34)cc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[O;H0;D2;+0:9]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 94 | [{"value": 94.0, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C)OC=1C=C2C=CC=NC2=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.9, "product": "COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C)OC=1C=C2C=CC=NC2=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using a procedure analogous to that described for Example 10, 4-chloro-6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazoline (74 mg, 0.23 mmol), (prepared as described for the starting material in Example 10), was reacted with 6-hydroxyquinoline (41 mg, 0.28 mol) to give 6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncccc2c1.c1ccc2ncncc2c1.C1CC[NH]CC1 | HCl | null | null | null | COc1cc2c(Cl)ncnc2cc1OCC1CCN(C)CC1.Oc1ccc2ncccc2c1>>COc1cc2c(Oc3ccc4ncccc4c3)ncnc2cc1OCC1CCN(C)CC1 |
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