dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e61a7047de7f4e138a9e806ad1918640 | CCOC(=O)c1cn2c(C)nnc2c(Cl)c1Nc1ccc(Br)cc1Cl>>Cc1nnc2c(Cl)c(Nc3ccc(Br)cc3Cl)c(C(=O)O)cn12 | [OH-].[Na+].C(C)OC(=O)C=1C(=C(C=2N(C1)C(=NN2)C)Cl)NC2=C(C=C(C=C2)Br)Cl.C1CCOC1.Cl>>BrC1=CC(=C(C=C1)NC1=C(C=2N(C=C1C(=O)O)C(=NN2)C)Cl)Cl | CC[O:21][C:19]([c:18]1[c:8]([NH:9][c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][c:16]2[Cl:17])[c:6]([Cl:7])[c:5]2[n:4][n:3][c:2]([CH3:1])[n:23]2[cH:22]1)=[O:20]>>[CH3:1][c:2]1[n:3][n:4][c:5]2[c:6]([Cl:7])[c:8]([NH:9][c:10]3[cH:11][cH:12][c:13]([Br:14])[cH:15][c:16]3[Cl:17])[c:18]([C:19](=[O:20])[OH:21])[cH:22][n:23]12 | CCOC(=O)c1cn2c(C)nnc2c(Cl)c1Nc1ccc(Br)cc1Cl | Cc1nnc2c(Cl)c(Nc3ccc(Br)cc3Cl)c(C(=O)O)cn12 | null | null | O.[Cl-].[Na+].O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Nc2ccn3cnnc3c2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | 16 | HOUR | Sodium hydroxide (715 μL of a 1 M solution) was added to a solution of 7-(4-bromo-2-chlorophenylamino)-8-chloro-3-methyl-[1,2,4]triazolo[4,3-a]pyridine-6-carboxylic acid ethyl ester (51a) (79 mg, 179 mmol) in 3:1 THF:water (4.5 mL). After 16 hours, the reaction mixture was poured into a separatory funnel, diluted with ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccn2cnnc2c1.c1ccccc1 | Other | O.[Cl-].[Na+].O | null | 16 | CCOC(=O)c1cn2c(C)nnc2c(Cl)c1Nc1ccc(Br)cc1Cl>O.[Cl-].[Na+].O>Cc1nnc2c(Cl)c(Nc3ccc(Br)cc3Cl)c(C(=O)O)cn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b8f7129a11664ebdbf36985da2e2fa2e | CCOC(=O)c1cnc(NN)c(Cl)c1Nc1ccc(Br)cc1Cl.O=C(Cl)Cc1ccccc1>>COC(=O)c1cn2c(Cc3ccccc3)nnc2c(Cl)c1Nc1ccc(Br)cc1Cl | C1(=CC=CC=C1)CC(=O)Cl.C1(=CC=CC=C1)CC(=O)Cl.C(C)OC(C1=CN=C(C(=C1NC1=C(C=C(C=C1)Br)Cl)Cl)NN)=O.C(C)N(CC)CC.O=P(Cl)(Cl)Cl>>COC(=O)C=1C(=C(C=2N(C1)C(=NN2)CC2=CC=CC=C2)Cl)NC2=C(C=C(C=C2)Br)Cl | C[CH2:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7][c:18]([NH:17][NH2:16])[c:19]([Cl:20])[c:21]1[NH:22][c:23]1[cH:24][cH:25][c:26]([Br:27])[cH:28][c:29]1[Cl:30].O=[C:8](Cl)[CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7]2[c:8]([CH2:9][c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[n:1... | CCOC(=O)c1cnc(NN)c(Cl)c1Nc1ccc(Br)cc1Cl.O=C(Cl)Cc1ccccc1 | COC(=O)c1cn2c(Cc3ccccc3)nnc2c(Cl)c1Nc1ccc(Br)cc1Cl | null | null | C(CCl)Cl.C(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | 06ab74c60ce8ef6b39033ec039502ec63eb866bdf2ff8953b25e03708212c9f6 | 1cacea87a450fad028c3559617d303476857f6994646fcc16cab567f4ef1481c | c1ccc(Cc2nnc3cc(Nc4ccccc4)ccn23)cc1 | C-[CH2;D2;+0:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6]:[n;H0;D2;+0:7]:[c:8](-[NH;D2;+0:9]-[NH2;D1;+0:10]):[c:11].Cl-[C;H0;D3;+0:12](=O)-[C:13]-[c:14]>>[CH3;D1;+0:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6]:[n;H0;D3;+0:7]1:[c:8](:[c:11]):[n;H0;D2;+0:9]:[n;H0;D2;+0:10]:[c;H0;D3;+0:12]:1-[C:13]-[c:14] | 33.4 | [{"value": 30.0, "product": "COC(=O)C=1C(=C(C=2N(C1)C(=NN2)CC2=CC=CC=C2)Cl)NC2=C(C=C(C=C2)Br)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 33.4, "product": "COC(=O)C=1C(=C(C=2N(C1)C(=NN2)CC2=CC=CC=C2)Cl)NC2=C(C=C(C=C2)Br)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | Phenylacetyl chloride (152 μL, 1.148 mmol) was added to a solution of 4-(4-bromo-2-chlorophenylamino)-5-chloro-6-hydrazinonicotinic acid methyl ester (49) (0.233 g, 0.574 mmol) and triethylamine (160 μL, 1.148 mmol) in CH2Cl2 (5.7 mL) at 0° C. After warming to room temperature, an additional 75 μL phenylacetyl chloride... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Hydrazine.Ester | Ester | c1ccncc1 | c1ccn2cnnc2c1 | c1ccccc1.c1ccn2cnnc2c1.c1ccccc1 | HCl | C(CCl)Cl.C(Cl)Cl | null | 6 | CCOC(=O)c1cnc(NN)c(Cl)c1Nc1ccc(Br)cc1Cl.O=C(Cl)Cc1ccccc1>C(CCl)Cl.C(Cl)Cl>COC(=O)c1cn2c(Cc3ccccc3)nnc2c(Cl)c1Nc1ccc(Br)cc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-db32bc23350740f1abb6cc7cce0f9309 | COC(=O)c1cc(C(C)=O)c(F)c(F)c1Nc1ccccc1Cl>>COC(=O)c1cc2c(C)onc2c(F)c1Nc1ccccc1Cl | [N-]=[N+]=[N-].[Na+].COC(C1=C(C(=C(C(=C1)C(C)=O)F)F)NC1=C(C=CC=C1)Cl)=O.CC(=O)C>>COC(=O)C1=CC=2C(=NOC2C)C(=C1NC1=C(C=CC=C1)Cl)F | F[c:12]1[c:7]([C:8]([CH3:9])=[O:10])[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:15]([NH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2[Cl:23])[c:13]1[F:14]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[c:8]([CH3:9])[o:10][n:11][c:12]2[c:13]([F:14])[c:15]1[NH:16][c:17]1[cH:18][cH:19][cH:20][cH:21][c:22]1[Cl:23] | COC(=O)c1cc(C(C)=O)c(F)c(F)c1Nc1ccccc1Cl | COC(=O)c1cc2c(C)onc2c(F)c1Nc1ccccc1Cl | null | null | O.CCOC(=O)C | Aromatic Heterocycle Formation | OtherReaction | e5744ec146e9700a0e2ef8f4d6f9eca44bb1bfe137990d90f1ff3a1b5ad172fa | d7a14902b3a6abdab109b69c987d4859648c171877b79e6c5d2b5477595da891 | c1ccc(Nc2ccc3conc3c2)cc1 | F-[c;H0;D3;+0:1](:[c:2](-[F;D1;H0:3]):[c:4]):[c:5](-[C;H0;D3;+0:6](-[C;D1;H3:7])=[O;H0;D1;+0:8]):[c:9]>>[C;D1;H3:7]-[c;H0;D3;+0:6]1:[o;H0;D2;+0:8]:[#7;a:10]:[c;H0;D3;+0:1](:[c:2](-[F;D1;H0:3]):[c:4]):[c:5]:1:[c:9] | 77 | [{"value": 77.0, "product": "COC(=O)C1=CC=2C(=NOC2C)C(=C1NC1=C(C=CC=C1)Cl)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.0, "product": "COC(=O)C1=CC=2C(=NOC2C)C(=C1NC1=C(C=CC=C1)Cl)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Sodium azide (128 mg, 1.95 mmol) was added to a mixture of 5-acetyl-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid methyl ester (6) (601 mg, 1.59 mmol) in 3:1 acetone:water (16 ml) and heated to reflux. After 16 hours, the reaction mixture was cooled to room temperature, and diluted with EtOAc and water. The organic ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | null | c1ccccc1 | c1ccc2nocc2c1 | c1ccc2nocc2c1.c1ccccc1 | null | O.CCOC(=O)C | null | 16 | COC(=O)c1cc(C(C)=O)c(F)c(F)c1Nc1ccccc1Cl>O.CCOC(=O)C>COC(=O)c1cc2c(C)onc2c(F)c1Nc1ccccc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cf6cf0cac0364cd59ba5c9d1ff16e067 | COC(=O)c1cc2c(C)onc2c(F)c1Nc1ccccc1Cl>>Cc1onc2c(F)c(Nc3ccccc3Cl)c(C(=O)O)cc12 | COC(=O)C1=CC=2C(=NOC2C)C(=C1NC1=C(C=CC=C1)Cl)F.C1CCOC1.[Li+].[OH-].Cl>>ClC1=C(C=CC=C1)NC=1C(=CC=2C(=NOC2C)C1F)C(=O)O | C[O:20][C:18]([c:17]1[c:8]([NH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[Cl:16])[c:6]([F:7])[c:5]2[n:4][o:3][c:2]([CH3:1])[c:22]2[cH:21]1)=[O:19]>>[CH3:1][c:2]1[o:3][n:4][c:5]2[c:6]([F:7])[c:8]([NH:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[Cl:16])[c:17]([C:18](=[O:19])[OH:20])[cH:21][c:22]12 | COC(=O)c1cc2c(C)onc2c(F)c1Nc1ccccc1Cl | Cc1onc2c(F)c(Nc3ccccc3Cl)c(C(=O)O)cc12 | null | null | O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Nc2ccc3conc3c2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 91 | [{"value": 91.0, "product": "ClC1=C(C=CC=C1)NC=1C(=CC=2C(=NOC2C)C1F)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.7, "product": "ClC1=C(C=CC=C1)NC=1C(=CC=2C(=NOC2C)C1F)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 6-(2-chlorophenylamino)-7-fluoro-3-methyl-benzo[c]-isoxazole-5-carboxylic acid methyl ester (55) (100 mg, 0.299 mmol) in 6:1 THF:water (3.5 mL) was added LiOH (0.60 ml of a 1 M solution in water). After 1 hour, the reaction was acidified to pH 1 with 1 N HCl, diluted with water and extracted with EtOAc... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2nocc2c1.c1ccccc1 | Other | O | null | 1 | COC(=O)c1cc2c(C)onc2c(F)c1Nc1ccccc1Cl>O>Cc1onc2c(F)c(Nc3ccccc3Cl)c(C(=O)O)cc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-07174ae39d004ca9a3623e64f59c121c | COC(=O)c1cnc(N)c(Cl)c1Nc1ccc(Br)cc1Cl.O=CC(Cl)C=O>>COC(=O)c1cn2c(C=O)cnc2c(Cl)c1Nc1ccc(Br)cc1Cl | COC(C1=CN=C(C(=C1NC1=C(C=C(C=C1)Br)Cl)Cl)N)=O.ClC(C=O)C=O>>COC(=O)C=1C(=C(C=2N(C1)C(=CN2)C=O)Cl)NC2=C(C=C(C=C2)Br)Cl | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7][c:13]([NH2:12])[c:14]([Cl:15])[c:16]1[NH:17][c:18]1[cH:19][cH:20][c:21]([Br:22])[cH:23][c:24]1[Cl:25].O=[CH:11][CH:8](Cl)[CH:9]=[O:10]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7]2[c:8]([CH:9]=[O:10])[cH:11][n:12][c:13]2[c:14]([Cl:15])[c:16]1[NH:17][c:18]1[cH:19][cH:20][c:21]([... | COC(=O)c1cnc(N)c(Cl)c1Nc1ccc(Br)cc1Cl.O=CC(Cl)C=O | COC(=O)c1cn2c(C=O)cnc2c(Cl)c1Nc1ccc(Br)cc1Cl | null | null | null | Aromatic Heterocycle Formation | OtherReaction | aa2630788ad7f4b98b88a0bb6ce6643b41a4745823fcca8f38118ef044e276ec | 777cfb7a0a90e330de341575c7c413a37b4b63909c3b8d37339ba538f80763a2 | c1ccc(Nc2ccn3ccnc3c2)cc1 | Cl-[CH;D3;+0:1](-[C:2]=[O;D1;H0:3])-[CH;D2;+0:4]=O.[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9]:[n;H0;D2;+0:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9]:[n;H0;D3;+0:10]1:[c:11](:[c:13]):[n;H0;D2;+0:12]:[cH;D2;+0:4]:[c;H0;D3;+0:1]:1-[C:2]=[O;D1;H0:3] | null | [] | 80 | CELSIUS | null | null | A suspension of 6-amino-4-(4-bromo-2-chlorophenylamino)-5-chloro-nicotinic acid methyl ester (28) (1.06 g, 2.72 mmol) and 2-chloro-malonaldehyde (587 mg, 5.43 mmol) was heated to 80° C. for 45 minutes. The solution was allowed to cool to room temperature, and then washed with saturated aqueous NaHCO3, and brine. The or... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aldehyde.Aldehyde.Primary amine | Aldehyde | c1ccncc1 | c1ccn2ccnc2c1 | c1ccn2ccnc2c1.c1ccccc1 | HCl | null | 80 | null | COC(=O)c1cnc(N)c(Cl)c1Nc1ccc(Br)cc1Cl.O=CC(Cl)C=O>>COC(=O)c1cn2c(C=O)cnc2c(Cl)c1Nc1ccc(Br)cc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e60f1ee7c4654e0094c366fbd38ba4d6 | CN.COC(=O)c1cn2c(C=O)cnc2c(Cl)c1Nc1ccc(Br)cc1Cl>>CNCc1cnc2c(Cl)c(Nc3ccc(Br)cc3Cl)c(C(=O)OC)cn12 | C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+].COC(=O)C=1C(=C(C=2N(C1)C(=CN2)C=O)Cl)NC2=C(C=C(C=C2)Br)Cl.C(C)(=O)O.CN>>COC(=O)C=1C(=C(C=2N(C1)C(=CN2)CNC)Cl)NC2=C(C=C(C=C2)Br)Cl | [CH3:1][NH2:2].O=[CH:3][c:4]1[cH:5][n:6][c:7]2[c:8]([Cl:9])[c:10]([NH:11][c:12]3[cH:13][cH:14][c:15]([Br:16])[cH:17][c:18]3[Cl:19])[c:20]([C:21](=[O:22])[O:23][CH3:24])[cH:25][n:26]12>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][n:6][c:7]2[c:8]([Cl:9])[c:10]([NH:11][c:12]3[cH:13][cH:14][c:15]([Br:16])[cH:17][c:18]3[Cl:19])[c:20](... | CN.COC(=O)c1cn2c(C=O)cnc2c(Cl)c1Nc1ccc(Br)cc1Cl | CNCc1cnc2c(Cl)c(Nc3ccc(Br)cc3Cl)c(C(=O)OC)cn12 | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(Nc2ccn3ccnc3c2)cc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:1:[c:7].[C;D1;H3:8]-[NH2;D1;+0:9]>>[C;D1;H3:8]-[NH;D2;+0:9]-[CH2;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:1:[c:7] | 46.8 | [{"value": 46.0, "product": "COC(=O)C=1C(=C(C=2N(C1)C(=CN2)CNC)Cl)NC2=C(C=C(C=C2)Br)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.8, "product": "COC(=O)C=1C(=C(C=2N(C1)C(=CN2)CNC)Cl)NC2=C(C=C(C=C2)Br)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | A suspension of 7-(4-bromo-2-chlorophenylamino)-8-chloro-3-formylimidazo[1,2-a]pyridine-6-carboxylic acid methyl ester (58) (25 mg, 0.056 mmol), acetic acid (7 μL, 0.11 mmol), and methylamine (2.0 M solution in THF, 56 μL, 0.11 mmol) was stirred for 0.5 hours. Sodium triacetoxyborohydride (36 mg, 0.17 mmol) was added a... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccn2ccnc2c1.c1ccccc1 | Other | null | null | 0.5 | CN.COC(=O)c1cn2c(C=O)cnc2c(Cl)c1Nc1ccc(Br)cc1Cl>>CNCc1cnc2c(Cl)c(Nc3ccc(Br)cc3Cl)c(C(=O)OC)cn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-effd8d1109d7499cbf3f109d0ae3e676 | COC(=O)c1cn2c(CNCC(=O)OC(C)(C)C)cnc2c(Cl)c1Nc1ccc(Br)cc1Cl>>CN(Cc1cnc2c(Cl)c(Nc3ccc(Br)cc3Cl)c(C(=O)O)cn12)C(=O)OC(C)(C)C | Cl.[OH-].[Na+].COC(=O)C=1C(=C(C=2N(C1)C(=CN2)CNCC(=O)OC(C)(C)C)Cl)NC2=C(C=C(C=C2)Br)Cl.CO.O>>BrC1=CC(=C(C=C1)NC1=C(C=2N(C=C1C(=O)O)C(=CN2)CN(C)C(=O)OC(C)(C)C)Cl)Cl | C[O:23][C:21]([c:20]1[c:10]([NH:11][c:12]2[cH:13][cH:14][c:15]([Br:16])[cH:17][c:18]2[Cl:19])[c:8]([Cl:9])[c:7]2[n:6][cH:5][c:4]([CH2:3][NH:2][CH2:1][C:26](=[O:27])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32])[n:25]2[cH:24]1)=[O:22]>>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][n:6][c:7]2[c:8]([Cl:9])[c:10]([NH:11][c:12]3[cH:13][cH:14... | COC(=O)c1cn2c(CNCC(=O)OC(C)(C)C)cnc2c(Cl)c1Nc1ccc(Br)cc1Cl | CN(Cc1cnc2c(Cl)c(Nc3ccc(Br)cc3Cl)c(C(=O)O)cn12)C(=O)OC(C)(C)C | null | null | O | Miscellaneous | OtherReaction | 1f73acab89b4d49cffa12bdd335b5b82dfc806de7b0f860018ca332cbad703ed | c69b5024139c8869fe89052e88181621aa4ee60a9d90514e6e13e7f94cbaf123 | c1ccc(Nc2ccn3ccnc3c2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]:[c:7](-[C:8]-[NH;D2;+0:9]-[CH2;D2;+0:10]-[C;H0;D3;+0:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C;D1;H3:17]):[c:18]:[#7;a:19]>>[#7;a:19]:[c:18]:[c:7](-[C:8]-[N;H0;D3;+0:9](-[CH3;D1;+0:10])-[C;H0;D3;+0:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D... | 84 | [{"value": 84.0, "product": "BrC1=CC(=C(C=C1)NC1=C(C=2N(C=C1C(=O)O)C(=CN2)CN(C)C(=O)OC(C)(C)C)Cl)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Sodium hydroxide (1.0 M aqueous solution, 0.16 mL, 0.16 mmol) is added to a solution of 7-(4-bromo-2-chlorophenylamino)-3-[(tert-butoxycarbonylmethylamino)-methyl]-8-chloroimidazo[1,2-a]pyridine-6-carboxylic acid methyl ester (60) (15 mg, 0.026 mmol) in 4:1 MeOH/water (5 mL). When the reaction was complete, the solutio... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Secondary amine | Carbamic ester.Carboxylic acid.Ether.Boc | null | null | c1ccn2ccnc2c1.c1ccccc1 | Other | O | null | null | COC(=O)c1cn2c(CNCC(=O)OC(C)(C)C)cnc2c(Cl)c1Nc1ccc(Br)cc1Cl>O>CN(Cc1cnc2c(Cl)c(Nc3ccc(Br)cc3Cl)c(C(=O)O)cn12)C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-20dc90001c9a415da8c5a6b5eb7186bb | CC(C)(C)OC(=O)CNCc1cnc2c(Cl)c(Nc3ccc(Br)cc3Cl)c(C(=O)O)cn12.NOCC1CC1>>CN(Cc1cnc2c(Cl)c(Nc3ccc(Br)cc3Cl)c(C(=O)NOCC3CC3)cn12)C(=O)OC(C)(C)C | C(C)(=O)OCC.CCN=C=NCCCN(C)C.Cl.C=1C=CC2=C(C1)N=NN2O.BrC1=CC(=C(C=C1)NC1=C(C=2N(C=C1C(=O)O)C(=CN2)CNCC(=O)OC(C)(C)C)Cl)Cl.C1(CC1)CON.C(C)N(CC)CC>>C(C)(C)(C)OC(N(C)CC1=CN=C2N1C=C(C(=C2Cl)NC2=C(C=C(C=C2)Br)Cl)C(NOCC2CC2)=O)=O | O[C:21]([c:20]1[c:10]([NH:11][c:12]2[cH:13][cH:14][c:15]([Br:16])[cH:17][c:18]2[Cl:19])[c:8]([Cl:9])[c:7]2[n:6][cH:5][c:4]([CH2:3][NH:2][CH2:1][C:31](=[O:32])[O:33][C:34]([CH3:35])([CH3:36])[CH3:37])[n:30]2[cH:29]1)=[O:22].[NH2:23][O:24][CH2:25][CH:26]1[CH2:27][CH2:28]1>>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][n:6][c:7]2[c:8]... | CC(C)(C)OC(=O)CNCc1cnc2c(Cl)c(Nc3ccc(Br)cc3Cl)c(C(=O)O)cn12.NOCC1CC1 | CN(Cc1cnc2c(Cl)c(Nc3ccc(Br)cc3Cl)c(C(=O)NOCC3CC3)cn12)C(=O)OC(C)(C)C | null | null | CC(=O)N(C)C | Protection | OtherReaction | f1f1a0875c88a2b344cba15f2f501db951c6ebccf2691778c30417c6be5a4b11 | 6b150a32efa368c46804b091268c9a58239514c23099ef222410a1a27a975dff | O=C(NOCC1CC1)c1cn2ccnc2cc1Nc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]1:[c:7]:[#7;a:8]:[c:9]:[c:10]:1-[C:11]-[NH;D2;+0:12]-[CH2;D2;+0:13]-[C;H0;D3;+0:14](=[O;D1;H0:15])-[#8:16]-[C:17](-[C;D1;H3:18])(-[C;D1;H3:19])-[C;D1;H3:20].[C:21]-[#8:22]-[NH2;D1;+0:23]>>[C:21]-[#8:22]-[NH;D2;+0:23]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[... | 85 | [{"value": 85.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | EDCl (6 mg, 0.033 mmol) and HOBt (5 mg, 0.033 mmol) were added to a solution of 7-(4-bromo-2-chlorophenylamino)-3-[(tert-butoxycarbonylmethylamino)-methyl]-8-chloro-imidazo[1,2-a]pyridine-6-carboxylic acid (61) in dimethylacetamide (0.4 mL). The yellow solution was allowed to stir at room temperature for 0.5 hours afte... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester.Primary amine.Secondary amine | Carbamic ester.Ether.Secondary amide.Boc | null | null | c1ccn2ccnc2c1.c1ccccc1.C1CC1 | HO- | CC(=O)N(C)C | null | 8 | CC(C)(C)OC(=O)CNCc1cnc2c(Cl)c(Nc3ccc(Br)cc3Cl)c(C(=O)O)cn12.NOCC1CC1>CC(=O)N(C)C>CN(Cc1cnc2c(Cl)c(Nc3ccc(Br)cc3Cl)c(C(=O)NOCC3CC3)cn12)C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2c93b4d4fd2a452f83f81f842a2239f5 | CN(Cc1cnc2c(Cl)c(Nc3ccc(Br)cc3Cl)c(C(=O)NOCC3CC3)cn12)C(=O)OC(C)(C)C>>CNCc1cnc2c(Cl)c(Nc3ccc(Br)cc3Cl)c(C(=O)NOCC3CC3)cn12 | C(C)(C)(C)OC(N(C)CC1=CN=C2N1C=C(C(=C2Cl)NC2=C(C=C(C=C2)Br)Cl)C(NOCC2CC2)=O)=O.ClCCl.FC(C(=O)O)(F)F>>C1(CC1)CONC(=O)C=1C(=C(C=2N(C1)C(=CN2)CNC)Cl)NC2=C(C=C(C=C2)Br)Cl | CC(C)(C)OC(=O)[N:2]([CH3:1])[CH2:3][c:4]1[cH:5][n:6][c:7]2[c:8]([Cl:9])[c:10]([NH:11][c:12]3[cH:13][cH:14][c:15]([Br:16])[cH:17][c:18]3[Cl:19])[c:20]([C:21](=[O:22])[NH:23][O:24][CH2:25][CH:26]3[CH2:27][CH2:28]3)[cH:29][n:30]12>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][n:6][c:7]2[c:8]([Cl:9])[c:10]([NH:11][c:12]3[cH:13][cH:14]... | CN(Cc1cnc2c(Cl)c(Nc3ccc(Br)cc3Cl)c(C(=O)NOCC3CC3)cn12)C(=O)OC(C)(C)C | CNCc1cnc2c(Cl)c(Nc3ccc(Br)cc3Cl)c(C(=O)NOCC3CC3)cn12 | null | null | null | Reduction | Boc amine deprotection | bbda4640db5f48af4538caded12fdadd56eacd6d4e5f7aefe46282d665df167e | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=C(NOCC1CC1)c1cn2ccnc2cc1Nc1ccccc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[c:4](:[#7;a:5]):[c:6]:[#7;a:7]>>[#7;a:5]:[c:4](-[C:3]-[NH;D2;+0:1]-[C;D1;H3:2]):[c:6]:[#7;a:7] | 83 | [{"value": 83.0, "product": "C1(CC1)CONC(=O)C=1C(=C(C=2N(C1)C(=CN2)CNC)Cl)NC2=C(C=C(C=C2)Br)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of [7-(4-bromo-2-chlorophenylamino)-8-chloro-6-cyclopropylmethoxy-carbamoyl-imidazo[1,2-a]pyridin-3-ylmethyl]-methyl-carbamic acid tert-butyl ester (62) in 1:1 dichloromethane/trifluoroacetic acid was stirred for two hours. Solvent was removed under reduced pressure and the residue redissolved into ethyl ace... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | null | null | c1ccn2ccnc2c1.c1ccccc1.C1CC1 | HO- | null | null | null | CN(Cc1cnc2c(Cl)c(Nc3ccc(Br)cc3Cl)c(C(=O)NOCC3CC3)cn12)C(=O)OC(C)(C)C>>CNCc1cnc2c(Cl)c(Nc3ccc(Br)cc3Cl)c(C(=O)NOCC3CC3)cn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4b9b6301407645a58c102b5f0a106557 | CC(Cl)OC(=O)Cl.CCS>>CCSC(=O)OC(C)Cl | C(C)S.C(C)N(CC)CC.ClC(=O)OC(C)Cl>>C(OC(C)Cl)(SCC)=O | Cl[C:4](=[O:5])[O:6][CH:7]([CH3:8])[Cl:9].[CH3:1][CH2:2][SH:3]>>[CH3:1][CH2:2][S:3][C:4](=[O:5])[O:6][CH:7]([CH3:8])[Cl:9] | CC(Cl)OC(=O)Cl.CCS | CCSC(=O)OC(C)Cl | null | null | C(C)OCC | Acylation | thioether_nucl_sub | 1e64d85185df227b30688cc91a7b5599fda55eef4d97baad42542d292c60862f | e25f8f686987a3d16d381c43fb269bbfe997b12f392a7cb69c3f21b45e42c5a6 | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C;D1;H3:5]-[C:6]-[SH;D1;+0:7]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[S;H0;D2;+0:7]-[C:6]-[C;D1;H3:5] | 89 | [{"value": 89.0, "product": "C(OC(C)Cl)(SCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.9, "product": "C(OC(C)Cl)(SCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A solution of 1-chloroethyl chloroformate (71.5 g, 0.5 mol) in diethyl ether (600 mL) was cooled to 0-4° C. in an ice-water bath and a solution of ethanethiol (37 mL, 0.5 mol) and triethylamine (69.3 mL, 0.5 mol) in diethyl ether (200 mL) was added dropwise over 1 h. The reaction mixture was removed from the ice bath a... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Aliphatic thiol | Ether.Monosulfide | null | null | null | HCl | C(C)OCC | null | 4 | CC(Cl)OC(=O)Cl.CCS>C(C)OCC>CCSC(=O)OC(C)Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aa1b1be5baa64a728d09278a5bd0313e | CC(C)(C)S.CC(Cl)OC(=O)Cl>>CC(Cl)OC(=O)SC(C)(C)C | C(C)(C)(C)S.ClC(=O)OC(C)Cl.CN1CCOCC1>>C(OC(C)Cl)(SC(C)(C)C)=O | [SH:7][C:8]([CH3:9])([CH3:10])[CH3:11].Cl[C:5]([O:4][CH:2]([CH3:1])[Cl:3])=[O:6]>>[CH3:1][CH:2]([Cl:3])[O:4][C:5](=[O:6])[S:7][C:8]([CH3:9])([CH3:10])[CH3:11] | CC(C)(C)S.CC(Cl)OC(=O)Cl | CC(Cl)OC(=O)SC(C)(C)C | null | null | C(Cl)Cl | Acylation | thioether_nucl_sub | 1e64d85185df227b30688cc91a7b5599fda55eef4d97baad42542d292c60862f | e25f8f686987a3d16d381c43fb269bbfe997b12f392a7cb69c3f21b45e42c5a6 | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C;D1;H3:5]-[C:6](-[C;D1;H3:7])(-[C;D1;H3:8])-[SH;D1;+0:9]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[S;H0;D2;+0:9]-[C:6](-[C;D1;H3:5])(-[C;D1;H3:7])-[C;D1;H3:8] | 89 | [{"value": 89.0, "product": "C(OC(C)Cl)(SC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.0, "product": "C(OC(C)Cl)(SC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A solution of tert-butyl thiol (180 g, 2 mol) and 1-chloroethyl chloroformate (284 g, 2 mol) in CH2Cl2 (1 L) was cooled to 0° C. in an ice-water bath. N-Methylmorpholine (212.1 g, 2.1 mol) was added dropwise over a period of 1 h and the reaction mixture was allowed to stir at room temperature for 16 h. The reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Aliphatic thiol | Ether.Monosulfide | null | null | null | HCl | C(Cl)Cl | null | 16 | CC(C)(C)S.CC(Cl)OC(=O)Cl>C(Cl)Cl>CC(Cl)OC(=O)SC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-097361bcf40b442c8d2dc604cdc92baa | CC(Cl)OC(=O)Cl.Sc1ccccc1>>CC(Cl)OC(=O)Sc1ccccc1 | C(C)N(CC)CC.C1(=CC=CC=C1)S.ClC(=O)OC(C)Cl>>C(OC(C)Cl)(SC1=CC=CC=C1)=O | Cl[C:5]([O:4][CH:2]([CH3:1])[Cl:3])=[O:6].[SH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[CH3:1][CH:2]([Cl:3])[O:4][C:5](=[O:6])[S:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1 | CC(Cl)OC(=O)Cl.Sc1ccccc1 | CC(Cl)OC(=O)Sc1ccccc1 | null | null | ClCCl.C(Cl)Cl | Acylation | thioether_nucl_sub | 3978f308f3250c89cbea32ce9713e8965cfa8792f1874ce54efdfd509c4dabe9 | 519bfe74e906772b61515a2291874fa5bdecca6886fffcbb6424325ea7e98e27 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[SH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[S;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | 98.5 | [{"value": 98.5, "product": "C(OC(C)Cl)(SC1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.5, "product": "C(OC(C)Cl)(SC1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | A solution of benzenethiol (50 g, 450 mmol) and 1-chloroethyl chloroformate (65 g, 450 mmol) in CH2Cl2 (300 mL) was cooled to 0-4° C. in an ice-water bath. To the mixture was added a solution of triethylamine (450 mmol) in dichloromethane (200 mL) dropwise over 30 min. The reaction was removed from the ice bath and sti... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Aromatic thiol | Ether.Monosulfide | null | null | c1ccccc1 | HCl | ClCCl.C(Cl)Cl | null | 12 | CC(Cl)OC(=O)Cl.Sc1ccccc1>ClCCl.C(Cl)Cl>CC(Cl)OC(=O)Sc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-78195199e32d4abaa861ba5154e7b4ae | CC(C)C(=O)O>>CC(C)C(=O)[O-] | [OH-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C(C)C)(=O)O>>C(C(C)C)(=O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC | [CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[OH:6]>>[CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[O-:6] | CC(C)C(=O)O | CC(C)C(=O)[O-] | null | null | O | Oxidation | Carboxylic acid to carboxylate | af9382a4a3fca177895c8a400271aa22025197fc08b983f9d71150044c1e6777 | b3097057beeca787f1d4960a7ee432572ee7aecad541233195b0dbbc0f674e9c | null | [C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4]>>[C:1]-[C:2](-[O-;H0;D1:4])=[O;D1;H0:3] | null | [] | null | null | null | null | A 40 wt % solution of tetrabutylammonium hydroxide in water (250 mL, 99 g, 382 mmol), water (300 mL) and isobutyric acid (33.8 g, 382 mmol) was stirred at ambient temperature for 30 min. The solvent was removed in vacuo to afford the title compound (5) as a waxy solid, which was used without further purification.
Condi... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | null | null | null | null | O | null | null | CC(C)C(=O)O>O>CC(C)C(=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-55b291c8e2044046a869b5ae58a39430 | CC(C)C(=O)O>>CC(C)C(=O)[O-] | [OH-].C(CCC)[N+](CCCC)(CCCC)CCCC.CO.C(C(C)C)(=O)O>>C(C(C)C)(=O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC | [CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[OH:6]>>[CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[O-:6] | CC(C)C(=O)O | CC(C)C(=O)[O-] | null | null | null | Oxidation | Carboxylic acid to carboxylate | af9382a4a3fca177895c8a400271aa22025197fc08b983f9d71150044c1e6777 | b3097057beeca787f1d4960a7ee432572ee7aecad541233195b0dbbc0f674e9c | null | [C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4]>>[C:1]-[C:2](-[O-;H0;D1:4])=[O;D1;H0:3] | null | [] | null | null | null | null | Alternatively, a 1M solution of tetrabutylammonium hydroxide in methanol (1 L, 1 mol) and isobutyric acid (88.5 g, 1 mol) was stirred at ambient temperature for 30 min. The solvent was removed in vacuo to afford the title compound (5) as a waxy solid, which was used without further purification.
Conditions: See reactio... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | null | null | null | null | null | null | null | CC(C)C(=O)O>>CC(C)C(=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e5fa1c7500d9466d82c7315eebd7857c | CC(C)C(=O)O.CSC(=O)OC(C)Cl>>CSC(=O)OC(C)OC(=O)C(C)C | C(OC(C)Cl)(SC)=O.C(C(C)C)(=O)O.C(C(C)C)(=O)O.C(C)(C)N(CC)C(C)C>>C(OC(C)OC(C(C)C)=O)(SC)=O | [OH:8][C:9](=[O:10])[CH:11]([CH3:12])[CH3:13].Cl[CH:6]([O:5][C:3]([S:2][CH3:1])=[O:4])[CH3:7]>>[CH3:1][S:2][C:3](=[O:4])[O:5][CH:6]([CH3:7])[O:8][C:9](=[O:10])[CH:11]([CH3:12])[CH3:13] | CC(C)C(=O)O.CSC(=O)OC(C)Cl | CSC(=O)OC(C)OC(=O)C(C)C | null | null | CCOCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a1c78245a699a2d7f32afead5a272e9f9c3376384617cf46d1f41528c07c62a0 | 24a9dd2a1f5258889ba19b94426efe6fc90f5f9d7c761574387c6d65581f3783 | null | Cl-[CH;D3;+0:1](-[C;D1;H3:2])-[#8:3]-[C:4](-[#16:5])=[O;D1;H0:6].[C:7]-[C:8](=[O;D1;H0:9])-[OH;D1;+0:10]>>[#16:5]-[C:4](=[O;D1;H0:6])-[#8:3]-[CH;D3;+0:1](-[C;D1;H3:2])-[O;H0;D2;+0:10]-[C:8](-[C:7])=[O;D1;H0:9] | 97 | [{"value": 97.0, "product": "C(OC(C)OC(C(C)C)=O)(SC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.0, "product": "C(OC(C)OC(C(C)C)=O)(SC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 55 | CELSIUS | null | null | Compound (1) (308 mg, 2 mmol) was dissolved in isobutyric acid (264 mg, 3 mmol). This mixture was slowly added to a pre-mixed solution of isobutyric acid (264 mg, 3 mmol) and diisopropylethylamine (387 mg, 3 mmol) and the reaction mixture heated to 55° C. for 16 h, diluted with ether (50 mL), washed with water (2×10 mL... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Carboxylic acid | Ester | null | null | null | HCl | CCOCC | 55 | null | CC(C)C(=O)O.CSC(=O)OC(C)Cl>CCOCC>CSC(=O)OC(C)OC(=O)C(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-28d3cce3be494893a4b299149ed1ce0e | CC(C)C(=O)[O-].CCSC(=O)OC(C)Cl>>CCSC(=O)OC(C)OC(=O)C(C)C | C(C(C)C)(=O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(OC(C)Cl)(SCC)=O>>C(OC(C)OC(C(C)C)=O)(SCC)=O | [O-:9][C:10](=[O:11])[CH:12]([CH3:13])[CH3:14].Cl[CH:7]([O:6][C:4]([S:3][CH2:2][CH3:1])=[O:5])[CH3:8]>>[CH3:1][CH2:2][S:3][C:4](=[O:5])[O:6][CH:7]([CH3:8])[O:9][C:10](=[O:11])[CH:12]([CH3:13])[CH3:14] | CC(C)C(=O)[O-].CCSC(=O)OC(C)Cl | CCSC(=O)OC(C)OC(=O)C(C)C | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | c4b9f8f0e97e27b0b79018d7a91e67cd98aea96bf160fdfec2f05850d4093366 | db536d01d4fbc476192b447c783c57fc0acdaf23478d7e09bd5fdb80ddf79bc8 | null | Cl-[CH;D3;+0:1](-[C;D1;H3:2])-[#8:3]-[C:4](-[#16:5])=[O;D1;H0:6].[C:7]-[C:8](-[O-;H0;D1:9])=[O;D1;H0:10]>>[#16:5]-[C:4](=[O;D1;H0:6])-[#8:3]-[CH;D3;+0:1](-[C;D1;H3:2])-[O;H0;D2;+0:9]-[C:8](-[C:7])=[O;D1;H0:10] | 63 | [{"value": 63.0, "product": "C(OC(C)OC(C(C)C)=O)(SCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.0, "product": "C(OC(C)OC(C(C)C)=O)(SCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of tetrabutylammonium isobutyrate (5) (382 mmol) in tetrahydrofuran (500 mL) was added compound (2) (49 g, 288 mmol). The mixture was stirred at ambient temperature for 16 h then the solvent removed in vacuo. The residue was dissolved in diethyl ether (600 mL), washed with water (3×300 mL) and the organic... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ether | Ester | null | null | null | Other | O1CCCC1 | null | 16 | CC(C)C(=O)[O-].CCSC(=O)OC(C)Cl>O1CCCC1>CCSC(=O)OC(C)OC(=O)C(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3bc65132c3dd477fa6d38a8141dd2485 | CC(C)C(=O)O.CC(Cl)OC(=O)SC(C)(C)C>>CC(OC(=O)SC(C)(C)C)OC(=O)C(C)C | C(OC(C)Cl)(SC(C)(C)C)=O.C(C(C)C)(=O)O.C(C(C)C)(=O)O.C(C)(C)N(CC)C(C)C>>C(OC(C)OC(C(C)C)=O)(SC(C)(C)C)=O | [OH:11][C:12](=[O:13])[CH:14]([CH3:15])[CH3:16].Cl[CH:2]([CH3:1])[O:3][C:4](=[O:5])[S:6][C:7]([CH3:8])([CH3:9])[CH3:10]>>[CH3:1][CH:2]([O:3][C:4](=[O:5])[S:6][C:7]([CH3:8])([CH3:9])[CH3:10])[O:11][C:12](=[O:13])[CH:14]([CH3:15])[CH3:16] | CC(C)C(=O)O.CC(Cl)OC(=O)SC(C)(C)C | CC(OC(=O)SC(C)(C)C)OC(=O)C(C)C | null | null | CCOCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a1c78245a699a2d7f32afead5a272e9f9c3376384617cf46d1f41528c07c62a0 | 24a9dd2a1f5258889ba19b94426efe6fc90f5f9d7c761574387c6d65581f3783 | null | Cl-[CH;D3;+0:1](-[C;D1;H3:2])-[#8:3]-[C:4](-[#16:5])=[O;D1;H0:6].[C:7]-[C:8](=[O;D1;H0:9])-[OH;D1;+0:10]>>[#16:5]-[C:4](=[O;D1;H0:6])-[#8:3]-[CH;D3;+0:1](-[C;D1;H3:2])-[O;H0;D2;+0:10]-[C:8](-[C:7])=[O;D1;H0:9] | 90.6 | [{"value": 90.0, "product": "C(OC(C)OC(C(C)C)=O)(SC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.6, "product": "C(OC(C)OC(C(C)C)=O)(SC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 55 | CELSIUS | null | null | Compound (3) (392 mg, 2 mmol) was dissolved in isobutyric acid (264 mg, 3 mmol) and the solution was slowly added to a pre-mixed solution of isobutyric acid (264 mg, 3 mmol) and diisopropylethylamine (387 mg, 3 mmol). The reaction mixture was heated to 55° C. for 16 h, then diluted with ether (50 mL), washed with water... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Carboxylic acid | Ester | null | null | null | HCl | CCOCC | 55 | null | CC(C)C(=O)O.CC(Cl)OC(=O)SC(C)(C)C>CCOCC>CC(OC(=O)SC(C)(C)C)OC(=O)C(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9a51be63b2354a1997c8f41ee5285522 | CC(C)C(=O)O.CC(Cl)OC(=O)Sc1ccccc1>>CC(OC(=O)Sc1ccccc1)OC(=O)C(C)C | C(OC(C)Cl)(SC1=CC=CC=C1)=O.C(C(C)C)(=O)O.C(C)N(CC)CC.[I-].[Na+]>>C(OC(C)OC(C(C)C)=O)(SC1=CC=CC=C1)=O | [OH:13][C:14](=[O:15])[CH:16]([CH3:17])[CH3:18].Cl[CH:2]([CH3:1])[O:3][C:4](=[O:5])[S:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[CH3:1][CH:2]([O:3][C:4](=[O:5])[S:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[O:13][C:14](=[O:15])[CH:16]([CH3:17])[CH3:18] | CC(C)C(=O)O.CC(Cl)OC(=O)Sc1ccccc1 | CC(OC(=O)Sc1ccccc1)OC(=O)C(C)C | null | null | C(C)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a1c78245a699a2d7f32afead5a272e9f9c3376384617cf46d1f41528c07c62a0 | 24a9dd2a1f5258889ba19b94426efe6fc90f5f9d7c761574387c6d65581f3783 | c1ccccc1 | Cl-[CH;D3;+0:1](-[C;D1;H3:2])-[#8:3]-[C:4](-[#16:5])=[O;D1;H0:6].[C:7]-[C:8](=[O;D1;H0:9])-[OH;D1;+0:10]>>[#16:5]-[C:4](=[O;D1;H0:6])-[#8:3]-[CH;D3;+0:1](-[C;D1;H3:2])-[O;H0;D2;+0:10]-[C:8](-[C:7])=[O;D1;H0:9] | 97 | [{"value": 97.0, "product": "C(OC(C)OC(C(C)C)=O)(SC1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | A mixture of compound (4) (10 g, 46 mmol), isobutyric acid (30 mL), triethylamine (30 mL) and sodium iodide (2 g) was stirred and heated in an oil bath at 50° C. for 3 days. The reaction mixture was diluted with diethyl ether (200 mL) and washed successively with water (3×100 mL), saturated aqueous sodium bicarbonate (... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Carboxylic acid | Ester | null | null | c1ccccc1 | HCl | C(C)OCC | 50 | null | CC(C)C(=O)O.CC(Cl)OC(=O)Sc1ccccc1>C(C)OCC>CC(OC(=O)Sc1ccccc1)OC(=O)C(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f5fdf094fbf64e4bbfad7efc41a84f83 | CSC(=O)OC(C)OC(=O)C(C)C.O=C1CCC(=O)N1O>>CC(OC(=O)OC1CC(=O)NC1=O)OC(=O)C(C)C | C(OC(C)OC(C(C)C)=O)(SC)=O.ON1C(CCC1=O)=O.C(C)(=O)OO.C(C)(=O)O>>C(C(C)C)(=O)OC(C)OC(=O)OC1C(=O)NC(C1)=O | CS[C:4]([O:3][CH:2]([CH3:1])[O:14][C:15](=[O:16])[CH:17]([CH3:18])[CH3:19])=[O:5].[OH:6][N:11]1[C:9](=[O:10])[CH2:8][CH2:7][C:12]1=[O:13]>>[CH3:1][CH:2]([O:3][C:4](=[O:5])[O:6][CH:7]1[CH2:8][C:9](=[O:10])[NH:11][C:12]1=[O:13])[O:14][C:15](=[O:16])[CH:17]([CH3:18])[CH3:19] | CSC(=O)OC(C)OC(=O)C(C)C.O=C1CCC(=O)N1O | CC(OC(=O)OC1CC(=O)NC1=O)OC(=O)C(C)C | null | null | CCOCC.C(Cl)Cl | Acylation | OtherReaction | 02135880cabf0520fe2823574725f3f8fc1c0bab0f84cd32266c3754d4ddc08a | acc814d6ee5ed8d60fec2d5fd5dfb0e09a3cffb805a07d7522f5fdeb2116a253 | O=C1CCC(=O)N1 | C-S-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[O;D1;H0:5]=[C:6]1-[C:7]-[CH2;D2;+0:8]-[C:9](=[O;D1;H0:10])-[N;H0;D3;+0:11]-1-[OH;D1;+0:12]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:12]-[CH;D3;+0:8]1-[C:7]-[C:6](=[O;D1;H0:5])-[NH;D2;+0:11]-[C:9]-1=[O;D1;H0:10] | 77 | [{"value": 77.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 3 | HOUR | To a solution of compound (6) (1 g, 4.8 mmol) in CH2Cl2 (10 mL) was added N-hydroxysuccinimide (1.1 g, 9.5 mmol) and the reaction mixture cooled to 0° C. A solution of 32% (v/v) peracetic acid in acetic acid (3.4 mL, 1.1 g, 14.4 mmol) was added dropwise over a period of 10 mm, then the solution allowed to stir at room ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Tertiary amide.Tertiary amide.Monosulfide | Carbonic Ester.Unsubstituted dicarboximide | C1CC[NH]C1 | C1CCNC1 | C1CCNC1 | Other | CCOCC.C(Cl)Cl | 0 | 3 | CSC(=O)OC(C)OC(=O)C(C)C.O=C1CCC(=O)N1O>CCOCC.C(Cl)Cl>CC(OC(=O)OC1CC(=O)NC1=O)OC(=O)C(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6d57c681b8834e76a2f56295c05a4671 | O=C(OO)c1cccc(Cl)c1>>O=C(O)c1cccc(Cl)c1 | C(C(C)C)(=O)OC(C)OC(=O)OC1C(=O)NC(C1)=O.ON1C(CCC1=O)=O.C(OC(C)OC(C(C)C)=O)(SC)=O.ClC1=CC(=CC=C1)C(=O)OO>>C(C(C)C)(=O)OC(C)OC(=O)OC1C(=O)NC(C1)=O.ClC=1C=C(C(=O)O)C=CC1 | O[O:22][C:21](=[O:20])[c:23]1[cH:24][cH:25][cH:26][c:27]([Cl:28])[cH:29]1>>[O:20]=[C:21]([OH:22])[c:23]1[cH:24][cH:25][cH:26][c:27]([Cl:28])[cH:29]1 | O=C(OO)c1cccc(Cl)c1 | O=C(O)c1cccc(Cl)c1 | null | null | CCOCC.C(Cl)Cl | Reduction | OtherReaction | a3a34f0a79d3ff42abf92863db20ba6c8958620c1c833b03092f42d83ad97bb6 | 531425a5a0d611c60dd4e710b59e4cf8c0bfa2d891e7bd03ed5bc1f943ee1b47 | c1ccccc1 | O-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | 16 | HOUR | In an alternative synthesis of (10), N-hydroxysuccinimide (558 mg, 4.8 mmol) was added to a solution of compound (6) (500 mg, 2.4 mmol) in CH2Cl2 (10 mL) and the reaction mixture cooled to 0° C. m-Chloroperbenzoic acid (1.62 g, 7.2 mmol, commercial grade: 77% in water) was added over a period of 10 min and the mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide | Carboxylic acid | null | null | c1ccccc1 | Other | CCOCC.C(Cl)Cl | null | 16 | O=C(OO)c1cccc(Cl)c1>CCOCC.C(Cl)Cl>O=C(O)c1cccc(Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5fd108b919624c62b4cb2d0c9160888a | O=C(OO)c1cccc(Cl)c1>>O=C(O)c1cccc(Cl)c1 | C(C(C)C)(=O)OC(C)OC(=O)OC1C(=O)NC(C1)=O.ON1C(CCC1=O)=O.C(OC(C)OC(C(C)C)=O)(SC(C)(C)C)=O.ClC1=CC(=CC=C1)C(=O)OO>>C(C(C)C)(=O)OC(C)OC(=O)OC1C(=O)NC(C1)=O.ClC=1C=C(C(=O)O)C=CC1 | O[O:22][C:21](=[O:20])[c:23]1[cH:24][cH:25][cH:26][c:27]([Cl:28])[cH:29]1>>[O:20]=[C:21]([OH:22])[c:23]1[cH:24][cH:25][cH:26][c:27]([Cl:28])[cH:29]1 | O=C(OO)c1cccc(Cl)c1 | O=C(O)c1cccc(Cl)c1 | null | null | CCOCC.C(Cl)Cl | Reduction | OtherReaction | a3a34f0a79d3ff42abf92863db20ba6c8958620c1c833b03092f42d83ad97bb6 | 531425a5a0d611c60dd4e710b59e4cf8c0bfa2d891e7bd03ed5bc1f943ee1b47 | c1ccccc1 | O-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | 16 | HOUR | In still another alternative synthesis of (10), N-hydroxysuccinimide (230 mg, 2 mmol) was added to a solution of compound (8) (248 mg, 1 mmol) in CH2Cl2 (10 mL) was added and the reaction mixture cooled to 0° C. m-Chloroperbenzoic acid (670 mg, 3 mmol, commercial grade: 77% in water) was added over a period of 10 min a... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide | Carboxylic acid | null | null | c1ccccc1 | Other | CCOCC.C(Cl)Cl | null | 16 | O=C(OO)c1cccc(Cl)c1>CCOCC.C(Cl)Cl>O=C(O)c1cccc(Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1934a0cf8729432495ba28b3d6194cc7 | NCC1(CC(=O)O)CCCCC1>>NCC1(CC(=O)[O-])CCCCC1 | C1CCC(CC1)(CC(=O)O)CN.[OH-].C(CCC)[N+](CCCC)(CCCC)CCCC>>NCC1(CCCCC1)CC(=O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC | [NH2:18][CH2:19][C:20]1([CH2:21][C:22](=[O:23])[OH:24])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1>>[NH2:18][CH2:19][C:20]1([CH2:21][C:22](=[O:23])[O-:24])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1 | NCC1(CC(=O)O)CCCCC1 | NCC1(CC(=O)[O-])CCCCC1 | null | null | CO | Oxidation | Carboxylic acid to carboxylate | af9382a4a3fca177895c8a400271aa22025197fc08b983f9d71150044c1e6777 | b3097057beeca787f1d4960a7ee432572ee7aecad541233195b0dbbc0f674e9c | C1CCCCC1 | [C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4]>>[C:1]-[C:2](-[O-;H0;D1:4])=[O;D1;H0:3] | null | [] | null | null | null | null | A solution containing gabapentin (34.4 g, 200 mmol), a 1 M solution of tetrabutylammonium hydroxide in methanol (200 mL, 200 mmol), and additional methanol (200 mL) was stirred at ambient temperature for 14 h. The solvent was removed in vacuo, then toluene (200 mL) was added and evaporated under reduced pressure two ti... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | null | null | C1CCCCC1 | null | CO | null | null | NCC1(CC(=O)O)CCCCC1>CO>NCC1(CC(=O)[O-])CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cc9be9edf1b94d39b0517d0002587328 | CC(OC(=O)OC1CC(=O)NC1=O)OC(=O)C(C)C.NCC1(CC(=O)O)CCCCC1>>CC(OC(=O)NCC1(CC(=O)O)CCCCC1)OC(=O)C(C)C | C1CCC(CC1)(CC(=O)O)CN.C([O-])(O)=O.[Na+].C(C(C)C)(=O)OC(C)OC(=O)OC1C(=O)NC(C1)=O>>C(C(C)C)(=O)OC(C)OC(=O)NCC1(CCCCC1)CC(=O)O | O=C1CC(O[C:4]([O:3][CH:2]([CH3:1])[O:18][C:19](=[O:20])[CH:21]([CH3:22])[CH3:23])=[O:5])C(=O)N1.[NH2:6][CH2:7][C:8]1([CH2:9][C:10](=[O:11])[OH:12])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1>>[CH3:1][CH:2]([O:3][C:4](=[O:5])[NH:6][CH2:7][C:8]1([CH2:9][C:10](=[O:11])[OH:12])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1)[O:18]... | CC(OC(=O)OC1CC(=O)NC1=O)OC(=O)C(C)C.NCC1(CC(=O)O)CCCCC1 | CC(OC(=O)NCC1(CC(=O)O)CCCCC1)OC(=O)C(C)C | null | null | O.C(C)#N.C(C)OCC | Protection | OtherReaction | 027d0fd8b951a171e70b3921f7d92c4a6800c5ef2d7b1bbadde0aa86898a31fc | f74d614cf84bcf20f6c6c1e8fa6e086089c89520408e8edf2b8e31f12242190c | C1CCCCC1 | O=C1-C-C(-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4])-C(=O)-N-1.[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6]-[C:5] | 96 | [{"value": 96.0, "product": "C(C(C)C)(=O)OC(C)OC(=O)NCC1(CCCCC1)CC(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.0, "product": "C(C(C)C)(=O)OC(C)OC(=O)NCC1(CCCCC1)CC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of gabapentin (1.7 g, 10 mmol) and sodium bicarbonate (20 mmol) in water (40 mL) was added a solution of compound (10) (2.73 g, 10 mmol) in acetonitrile (20 mL) over 1 min. The reaction was stirred at ambient temperature for 16 h. The reaction mixture was diluted with diethyl ether (100 mL) and washed wit... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Unsubstituted dicarboximide.Primary amine | Carbamic ester | C1CCNC1 | null | C1CCCCC1 | HO- | O.C(C)#N.C(C)OCC | null | 16 | CC(OC(=O)OC1CC(=O)NC1=O)OC(=O)C(C)C.NCC1(CC(=O)O)CCCCC1>O.C(C)#N.C(C)OCC>CC(OC(=O)NCC1(CC(=O)O)CCCCC1)OC(=O)C(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8aa22913bcad4306a3b567bf0203466f | CC(C)C(=O)O>>CC(C)C(=O)[O-] | C(C(C)C)(=O)O.[OH-].C[N+](C)(C)C>>C(C(C)C)(=O)[O-].C[N+](C)(C)C | [CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[OH:6]>>[CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[O-:6] | CC(C)C(=O)O | CC(C)C(=O)[O-] | null | null | null | Oxidation | Carboxylic acid to carboxylate | af9382a4a3fca177895c8a400271aa22025197fc08b983f9d71150044c1e6777 | b3097057beeca787f1d4960a7ee432572ee7aecad541233195b0dbbc0f674e9c | null | [C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4]>>[C:1]-[C:2](-[O-;H0;D1:4])=[O;D1;H0:3] | null | [] | null | null | null | null | To a 20 L round bottom flask was added isobutyric acid (1300 mL, 14 mol), and an aqueous solution of 25% tetramethylammonium hydroxide (5 L, 14 mol). The water was removed under reduced pressure, and azeotroped with toluene (2×2 L) to leave the product (15) as an amber liquid, which was used without further purificatio... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | null | null | null | null | null | null | null | CC(C)C(=O)O>>CC(C)C(=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-777faa7e89874a9282d528ed3c9f7d49 | CC(C)C(=O)O.CSC(=O)OOC(Cl)C(C)C>>CSC(=O)OOC(OC(=O)C(C)C)C(C)C | C(C(C)C)(=O)[O-].C[N+](C)(C)C.C(C(C)C)(=O)O.C(OOC(C(C)C)Cl)(SC)=O>>C(OOC(C(C)C)OC(C(C)C)=O)(SC)=O | [OH:8][C:9](=[O:10])[CH:11]([CH3:12])[CH3:13].Cl[CH:7]([O:6][O:5][C:3]([S:2][CH3:1])=[O:4])[CH:14]([CH3:15])[CH3:16]>>[CH3:1][S:2][C:3](=[O:4])[O:5][O:6][CH:7]([O:8][C:9](=[O:10])[CH:11]([CH3:12])[CH3:13])[CH:14]([CH3:15])[CH3:16] | CC(C)C(=O)O.CSC(=O)OOC(Cl)C(C)C | CSC(=O)OOC(OC(=O)C(C)C)C(C)C | null | null | CCOC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a1c78245a699a2d7f32afead5a272e9f9c3376384617cf46d1f41528c07c62a0 | 24a9dd2a1f5258889ba19b94426efe6fc90f5f9d7c761574387c6d65581f3783 | null | Cl-[CH;D3;+0:1](-[#8:2]-[#8:3]-[C:4]=[O;D1;H0:5])-[C:6](-[C;D1;H3:7])-[C;D1;H3:8].[C:9]-[C:10](=[O;D1;H0:11])-[OH;D1;+0:12]>>[C:9]-[C:10](=[O;D1;H0:11])-[O;H0;D2;+0:12]-[CH;D3;+0:1](-[#8:2]-[#8:3]-[C:4]=[O;D1;H0:5])-[C:6](-[C;D1;H3:7])-[C;D1;H3:8] | 67.7 | [{"value": 65.0, "product": "C(OOC(C(C)C)OC(C(C)C)=O)(SC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.7, "product": "C(OOC(C(C)C)OC(C(C)C)=O)(SC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | To a 3 L three neck round bottom flask equipped with a mechanical stirrer and teflon-coated thermocouple was added (15) (1672 g, 9 mol), isobutyric acid (264 g, 1.5 mol), and (14) (1050 g, 5.76 mol). The reaction mixture was heated to 80° C. for 12 h, monitoring the reaction progress by 1H NMR. The reaction mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Carboxylic acid | Ester | null | null | null | HCl | CCOC(=O)C | 80 | null | CC(C)C(=O)O.CSC(=O)OOC(Cl)C(C)C>CCOC(=O)C>CSC(=O)OOC(OC(=O)C(C)C)C(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a1e5675904344e97b8bb7ba7e574b260 | CSC(=O)OOC(OC(=O)C(C)C)C(C)C.O=C(O[C@@H]1C(=O)N(O)C(=O)[C@H]1OC(=O)c1ccccc1)c1ccccc1>>CC(C)C(=O)O[C@H](OC(=O)ON1C(=O)[C@@H](OC(=O)c2ccccc2)[C@H](OC(=O)c2ccccc2)C1=O)C(C)C | ON1C([C@H]([C@@H](C1=O)OC(C1=CC=CC=C1)=O)OC(C1=CC=CC=C1)=O)=O.C(OOC(C(C)C)OC(C(C)C)=O)(SC)=O.C(C)(=O)OO.C(C)(=O)OO>>CC(C(=O)O[C@@H](C(C)C)OC(=O)ON1C([C@H]([C@@H](C1=O)OC(C1=CC=CC=C1)=O)OC(C1=CC=CC=C1)=O)=O)C | CS[C:9](O[O:8][CH:7]([O:6][C:4]([CH:2]([CH3:1])[CH3:3])=[O:5])[CH:37]([CH3:38])[CH3:39])=[O:10].[OH:11][N:12]1[C:13](=[O:14])[C@@H:15]([O:16][C:17](=[O:18])[c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[C@H:25]([O:26][C:27](=[O:28])[c:29]2[cH:30][cH:31][cH:32][cH:33][cH:34]2)[C:35]1=[O:36]>>[CH3:1][CH:2]([CH3:3])[C:4](=[... | CSC(=O)OOC(OC(=O)C(C)C)C(C)C.O=C(O[C@@H]1C(=O)N(O)C(=O)[C@H]1OC(=O)c1ccccc1)c1ccccc1 | CC(C)C(=O)O[C@H](OC(=O)ON1C(=O)[C@@H](OC(=O)c2ccccc2)[C@H](OC(=O)c2ccccc2)C1=O)C(C)C | null | null | ClCCl.C(C)(=O)O | Acylation | OtherReaction | 1a0d65d95c03f609c9ba14e788b1ef64da345e59cee201a8100967aef66d4c98 | b8c84c3e0ba8877f8793c358e95ebb320bfaabe7f65a860968c1a83a5d892903 | O=C(O[C@@H]1C(=O)NC(=O)[C@H]1OC(=O)c1ccccc1)c1ccccc1 | C-S-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-[O;H0;D2;+0:3]-[CH;D3;+0:4](-[#8:5]-[C:6](-[C:7])=[O;D1;H0:8])-[C:9](-[C;D1;H3:10])-[C;D1;H3:11].[O;D1;H0:12]=[C:13]1-[C:14]-[C:15]-[C:16](=[O;D1;H0:17])-[#7:18]-1-[OH;D1;+0:19]>>[C:7]-[C:6](=[O;D1;H0:8])-[#8:5]-[C@H;D3;+0:4](-[O;H0;D2;+0:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:19... | 25.7 | [{"value": 25.0, "product": "CC(C(=O)O[C@@H](C(C)C)OC(=O)ON1C([C@H]([C@@H](C1=O)OC(C1=CC=CC=C1)=O)OC(C1=CC=CC=C1)=O)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 25.7, "product": "CC(C(=O)O[C@@H](C(C)C)OC(=O)ON1C([C@H]([C@@H](C1=O)OC(C1=CC=CC=C1)=O)OC(C1=CC=CC=C1)=O)=O)C", "details": "CALCULATEDPERC... | null | null | 8 | HOUR | To a stirred solution of compound (18) (35 g, 98.6 mmol) and thiocarbonate (13) (34.6 g, 148 mmol) in dichloromethane at 0° C. was dropwise added a 32% solution of peracetic acid (300 mmol) in acetic acid over 2 h. The reaction temperature was kept below 35° C. during the addition of peracetic acid. After the addition ... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide.Monosulfide | Ether | null | null | C1CC[NH]C1.c1ccccc1.c1ccccc1 | Other | ClCCl.C(C)(=O)O | null | 8 | CSC(=O)OOC(OC(=O)C(C)C)C(C)C.O=C(O[C@@H]1C(=O)N(O)C(=O)[C@H]1OC(=O)c1ccccc1)c1ccccc1>ClCCl.C(C)(=O)O>CC(C)C(=O)O[C@H](OC(=O)ON1C(=O)[C@@H](OC(=O)c2ccccc2)[C@H](OC(=O)c2ccccc2)C1=O)C(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bec25c2af5d04244be0f509c18c823c6 | O=C(O[C@@H](C(=O)O)[C@@H](OC(=O)c1ccccc1)C(=O)O)c1ccccc1>>O=C(O[C@H]1C(=O)OC(=O)[C@@H]1OC(=O)c1ccccc1)c1ccccc1 | C1=CC=C(C=C1)C(=O)O[C@H]([C@H](C(=O)O)OC(=O)C2=CC=CC=C2)C(=O)O.C(C)(=O)OC(C)=O>>O=C1OC([C@@H]([C@H]1OC(C1=CC=CC=C1)=O)OC(C1=CC=CC=C1)=O)=O | O[C:5]([C@H:4]([O:3][C:2](=[O:1])[c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1)[C@H:10]([C:8]([OH:7])=[O:9])[O:11][C:12](=[O:13])[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)=[O:6]>>[O:1]=[C:2]([O:3][C@H:4]1[C:5](=[O:6])[O:7][C:8](=[O:9])[C@@H:10]1[O:11][C:12](=[O:13])[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)[c:20]1[cH... | O=C(O[C@@H](C(=O)O)[C@@H](OC(=O)c1ccccc1)C(=O)O)c1ccccc1 | O=C(O[C@H]1C(=O)OC(=O)[C@@H]1OC(=O)c1ccccc1)c1ccccc1 | null | null | null | Miscellaneous | OtherReaction | dfa11c0c8b4511b7073a013bc90c6b8429c487af9f4101a7fcdad6ab1a1fd93d | 22fb50577915472f1babb105381e408122dc09b3472eabb73e6e4daecfef90f6 | O=C(O[C@H]1C(=O)OC(=O)[C@@H]1OC(=O)c1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[#8:4]-[C:5]=[O;D1;H0:6])-[C:7]-[C:8](=[O;D1;H0:9])-[OH;D1;+0:10]>>[O;D1;H0:6]=[C:5]-[#8:4]-[C:3]1-[C:7]-[C:8](=[O;D1;H0:9])-[O;H0;D2;+0:10]-[C;H0;D3;+0:1]-1=[O;D1;H0:2] | null | [] | 85 | CELSIUS | null | null | To a 3-necked 5 L round bottom flask fitted with a mechanical stirrer and a teflon coated thermocouple was added (−)-2,3-dibenzoyl-L-tartaric acid (1000 g, 2.79 mol) followed by acetic anhydride (2 L). The suspension was stirred and heated to 85° C. for 2 h during which time the starting material gradually dissolved. A... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid | Anhydride | null | C1CCOC1 | C1CCOC1.c1ccccc1.c1ccccc1 | HO- | null | 85 | null | O=C(O[C@@H](C(=O)O)[C@@H](OC(=O)c1ccccc1)C(=O)O)c1ccccc1>>O=C(O[C@H]1C(=O)OC(=O)[C@@H]1OC(=O)c1ccccc1)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d01879c487774bae935d5be782b66a84 | NO.O=C(O[C@H]1C(=O)OC(=O)[C@@H]1OC(=O)c1ccccc1)c1ccccc1>>O=C(O[C@H]1C(=O)N(O)C(=O)[C@@H]1OC(=O)c1ccccc1)c1ccccc1 | NO.O.O=C1OC([C@@H]([C@H]1OC(C1=CC=CC=C1)=O)OC(C1=CC=CC=C1)=O)=O.C(C)#N>>ON1C([C@@H]([C@H](C1=O)OC(C1=CC=CC=C1)=O)OC(C1=CC=CC=C1)=O)=O | [NH2:7][OH:8].O1[C:5](=[O:6])[C@H:4]([O:3][C:2](=[O:1])[c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[C@@H:11]([O:12][C:13](=[O:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[C:9]1=[O:10]>>[O:1]=[C:2]([O:3][C@H:4]1[C:5](=[O:6])[N:7]([OH:8])[C:9](=[O:10])[C@@H:11]1[O:12][C:13](=[O:14])[c:15]1[cH:16][cH:17][cH:18][cH:19]... | NO.O=C(O[C@H]1C(=O)OC(=O)[C@@H]1OC(=O)c1ccccc1)c1ccccc1 | O=C(O[C@H]1C(=O)N(O)C(=O)[C@@H]1OC(=O)c1ccccc1)c1ccccc1 | null | null | C1(=CC=CC=C1)C | Acylation | OtherReaction | ac5f63bba60d4a1d0330a86ebe6d3207e2dd9014985e5a45540d3ddb5de76511 | f570959c6614f83205be0ddef7485420f00ece3dc52d54ad514eee7326c7fc88 | O=C(O[C@H]1C(=O)NC(=O)[C@@H]1OC(=O)c1ccccc1)c1ccccc1 | [NH2;D1;+0:1]-[O;D1;H1:2].[O;D1;H0:3]=[C;H0;D3;+0:4]1-O-[C;H0;D3;+0:5](=[O;D1;H0:6])-[C:7](-[#8:8]-[C:9]=[O;D1;H0:10])-[C:11]-1-[#8:12]-[C:13]=[O;D1;H0:14]>>[O;D1;H0:3]=[C;H0;D3;+0:4]1-[C:11](-[#8:12]-[C:13]=[O;D1;H0:14])-[C:7](-[#8:8]-[C:9]=[O;D1;H0:10])-[C;H0;D3;+0:5](=[O;D1;H0:6])-[N;H0;D3;+0:1]-1-[O;D1;H1:2] | 87.1 | [{"value": 87.0, "product": "ON1C([C@@H]([C@H](C1=O)OC(C1=CC=CC=C1)=O)OC(C1=CC=CC=C1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.1, "product": "ON1C([C@@H]([C@H](C1=O)OC(C1=CC=CC=C1)=O)OC(C1=CC=CC=C1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 4 | CELSIUS | 1 | HOUR | To a 3-neck 5 L round bottom flask fitted with a mechanical stirrer and a teflon coated temperature probe was added (22) (2.79 mol) followed by acetonitrile (2 L). The suspension was cooled in an ice bath to 4° C., followed by the addition of 50% aqueous hydroxylamine (180 mL, 2.93 mol) over 1 h. The starting material ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Tertiary amide.Tertiary amide | C1CCOC1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1.c1ccccc1 | HO- | C1(=CC=CC=C1)C | 4 | 1 | NO.O=C(O[C@H]1C(=O)OC(=O)[C@@H]1OC(=O)c1ccccc1)c1ccccc1>C1(=CC=CC=C1)C>O=C(O[C@H]1C(=O)N(O)C(=O)[C@@H]1OC(=O)c1ccccc1)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-152e443356ff434289acdc7b1da08d2d | CSC(=O)OOC(OC(=O)C(C)C)C(C)C.O=C(O[C@H]1C(=O)N(O)C(=O)[C@@H]1OC(=O)c1ccccc1)c1ccccc1>>CC(C)C(=O)O[C@@H](OC(=O)ON1C(=O)[C@H](OC(=O)c2ccccc2)[C@@H](OC(=O)c2ccccc2)C1=O)C(C)C | C(OOC(C(C)C)OC(C(C)C)=O)(SC)=O.ON1C([C@@H]([C@H](C1=O)OC(C1=CC=CC=C1)=O)OC(C1=CC=CC=C1)=O)=O.C(C)(=O)OO.C(C)(=O)O>>CC(C(=O)O[C@H](C(C)C)OC(=O)ON1C([C@@H]([C@H](C1=O)OC(C1=CC=CC=C1)=O)OC(C1=CC=CC=C1)=O)=O)C | CS[C:9](O[O:8][CH:7]([O:6][C:4]([CH:2]([CH3:1])[CH3:3])=[O:5])[CH:37]([CH3:38])[CH3:39])=[O:10].[OH:11][N:12]1[C:13](=[O:14])[C@H:15]([O:16][C:17](=[O:18])[c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[C@@H:25]([O:26][C:27](=[O:28])[c:29]2[cH:30][cH:31][cH:32][cH:33][cH:34]2)[C:35]1=[O:36]>>[CH3:1][CH:2]([CH3:3])[C:4](=[... | CSC(=O)OOC(OC(=O)C(C)C)C(C)C.O=C(O[C@H]1C(=O)N(O)C(=O)[C@@H]1OC(=O)c1ccccc1)c1ccccc1 | CC(C)C(=O)O[C@@H](OC(=O)ON1C(=O)[C@H](OC(=O)c2ccccc2)[C@@H](OC(=O)c2ccccc2)C1=O)C(C)C | null | null | ClCCCl | Acylation | OtherReaction | 1a0d65d95c03f609c9ba14e788b1ef64da345e59cee201a8100967aef66d4c98 | b8c84c3e0ba8877f8793c358e95ebb320bfaabe7f65a860968c1a83a5d892903 | O=C(O[C@H]1C(=O)NC(=O)[C@@H]1OC(=O)c1ccccc1)c1ccccc1 | C-S-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-[O;H0;D2;+0:3]-[CH;D3;+0:4](-[#8:5]-[C:6](-[C:7])=[O;D1;H0:8])-[C:9](-[C;D1;H3:10])-[C;D1;H3:11].[O;D1;H0:12]=[C:13]1-[C:14]-[C:15]-[C:16](=[O;D1;H0:17])-[#7:18]-1-[OH;D1;+0:19]>>[C:7]-[C:6](=[O;D1;H0:8])-[#8:5]-[C@@H;D3;+0:4](-[O;H0;D2;+0:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:1... | 25 | [{"value": 25.0, "product": "CC(C(=O)O[C@H](C(C)C)OC(=O)ON1C([C@@H]([C@H](C1=O)OC(C1=CC=CC=C1)=O)OC(C1=CC=CC=C1)=O)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | 15 | CELSIUS | null | null | A 3 L three necked round bottom flask fitted with a mechanical stirrer, teflon coated temperature probe and an addition funnel was charged with (13) (234 g, 1 mol), (23) (330 g, 0.95 mol), and 1,2-dichloroethane (2200 mL). The reaction mixture was cooled under a nitrogen atmosphere in an ice water bath to 15° C. To the... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide.Monosulfide | Ether | null | null | C1CC[NH]C1.c1ccccc1.c1ccccc1 | Other | ClCCCl | 15 | null | CSC(=O)OOC(OC(=O)C(C)C)C(C)C.O=C(O[C@H]1C(=O)N(O)C(=O)[C@@H]1OC(=O)c1ccccc1)c1ccccc1>ClCCCl>CC(C)C(=O)O[C@@H](OC(=O)ON1C(=O)[C@H](OC(=O)c2ccccc2)[C@@H](OC(=O)c2ccccc2)C1=O)C(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bc9f4510ccde47d884e6fab83b6a1ae2 | CC(C)C(=O)Cl.O=C(O)[C@H](O)[C@@H](O)C(=O)O>>CC(C)C(=O)O[C@H]1C(=O)OC(=O)[C@@H]1OC(=O)C(C)C | C([C@H](O)[C@@H](O)C(=O)O)(=O)O.C(C(C)C)(=O)Cl>>O=C1OC([C@@H]([C@H]1OC(C(C)C)=O)OC(C(C)C)=O)=O | Cl[C:4]([CH:2]([CH3:1])[CH3:3])=[O:5].[OH:6][C@@H:19]([C:7](=[O:9])[OH:10])[C@@H:17]([OH:12])[C:15]([OH:14])=[O:16]>>[CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[O:6][C@H:7]1[C:8](=[O:9])[O:10][C:11](=[O:12])[C@@H:13]1[O:14][C:15](=[O:16])[CH:17]([CH3:18])[CH3:19] | CC(C)C(=O)Cl.O=C(O)[C@H](O)[C@@H](O)C(=O)O | CC(C)C(=O)O[C@H]1C(=O)OC(=O)[C@@H]1OC(=O)C(C)C | null | null | CCCCCC.CCOCC.C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 97e945862434d253355980141463740476b1aa5c4b8db8c31d16a34baf59ec6b | e0cfefbc9524ccf2e9a1480627bd015eb0fec489618391d800bcffef29909ee4 | O=C1CCC(=O)O1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[C;D1;H3:5].[O;D1;H0:6]=[C:7](-[OH;D1;+0:8])-[C@H;D3;+0:9](-[OH;D1;+0:10])-[C@@H;D3;+0:11](-[OH;D1;+0:12])-[C;H0;D3;+0:13](=[O;H0;D1;+0:14])-[OH;D1;+0:15]>>[C;D1;H3:16]-[CH;D3;+0:9](-[CH3;D1;+0:11])-[C:7](=[O;D1;H0:6])-[O;H0;D2;+0:8]-[C:17]1-[C:18](=[O;H0;D1;+0:10])-[... | 71 | [{"value": 71.0, "product": "O=C1OC([C@@H]([C@H]1OC(C(C)C)=O)OC(C(C)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.6, "product": "O=C1OC([C@@H]([C@H]1OC(C(C)C)=O)OC(C(C)C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 22 | HOUR | To a suspension of L-tartaric acid (5.0 g, 33.3 mmol) in toluene (60 mL) was added isobutyryl chloride (11.3 mL, 107 mmol). The resulting suspension was heated to reflux and stirred for 22 h at reflux temperature. The reaction mixture was then concentrated in vacuo to afford a crystalline solid, which was suspended in ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Carboxylic acid.Carboxylic acid.Secondary alcohol.Secondary alcohol | Anhydride.Ester.Ester | null | C1CCOC1 | C1CCOC1 | null | CCCCCC.CCOCC.C1(=CC=CC=C1)C | null | 22 | CC(C)C(=O)Cl.O=C(O)[C@H](O)[C@@H](O)C(=O)O>CCCCCC.CCOCC.C1(=CC=CC=C1)C>CC(C)C(=O)O[C@H]1C(=O)OC(=O)[C@@H]1OC(=O)C(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6e46d3d6429541e5b8d2ad8aa41254d4 | CC(C)C(=O)O[C@H]1C(=O)OC(=O)[C@@H]1OC(=O)C(C)C.NO>>CC(C)C(=O)O[C@H]1C(=O)N(O)C(=O)[C@@H]1OC(=O)C(C)C | O=C1OC([C@@H]([C@H]1OC(C(C)C)=O)OC(C(C)C)=O)=O.NO>>ON1C([C@@H]([C@H](C1=O)OC(C(C)C)=O)OC(C(C)C)=O)=O | O1[C:8](=[O:9])[C@H:7]([O:6][C:4]([CH:2]([CH3:1])[CH3:3])=[O:5])[C@@H:14]([O:15][C:16](=[O:17])[CH:18]([CH3:19])[CH3:20])[C:12]1=[O:13].[NH2:10][OH:11]>>[CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[O:6][C@H:7]1[C:8](=[O:9])[N:10]([OH:11])[C:12](=[O:13])[C@@H:14]1[O:15][C:16](=[O:17])[CH:18]([CH3:19])[CH3:20] | CC(C)C(=O)O[C@H]1C(=O)OC(=O)[C@@H]1OC(=O)C(C)C.NO | CC(C)C(=O)O[C@H]1C(=O)N(O)C(=O)[C@@H]1OC(=O)C(C)C | null | null | C(C)(=O)OCC | Acylation | OtherReaction | ac5f63bba60d4a1d0330a86ebe6d3207e2dd9014985e5a45540d3ddb5de76511 | f570959c6614f83205be0ddef7485420f00ece3dc52d54ad514eee7326c7fc88 | O=C1CCC(=O)N1 | [NH2;D1;+0:1]-[O;D1;H1:2].[O;D1;H0:3]=[C;H0;D3;+0:4]1-O-[C;H0;D3;+0:5](=[O;D1;H0:6])-[C:7](-[#8:8]-[C:9]=[O;D1;H0:10])-[C:11]-1-[#8:12]-[C:13]=[O;D1;H0:14]>>[O;D1;H0:3]=[C;H0;D3;+0:4]1-[C:11](-[#8:12]-[C:13]=[O;D1;H0:14])-[C:7](-[#8:8]-[C:9]=[O;D1;H0:10])-[C;H0;D3;+0:5](=[O;D1;H0:6])-[N;H0;D3;+0:1]-1-[O;D1;H1:2] | 99.7 | [{"value": 99.7, "product": "ON1C([C@@H]([C@H](C1=O)OC(C(C)C)=O)OC(C(C)C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a stirred solution of compound (27) (5.98 g, 22 mmol) in ethyl acetate (50 mL) at 0° C. was added a 50% aqueous solution of hydroxylamine (1.75 g, 26.4 mmol). The resulting mixture was stirred at room temperature for 3 h and washed successively with aqueous citric acid solution and brine, then dried over anhydrous s... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Tertiary amide.Tertiary amide | C1CCOC1 | C1CC[NH]C1 | C1CC[NH]C1 | HO- | C(C)(=O)OCC | null | 3 | CC(C)C(=O)O[C@H]1C(=O)OC(=O)[C@@H]1OC(=O)C(C)C.NO>C(C)(=O)OCC>CC(C)C(=O)O[C@H]1C(=O)N(O)C(=O)[C@@H]1OC(=O)C(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4c6e1195c4934a40a35ac509c0a478ad | CC(C)C(=O)Cl.O=C(O)[C@@H](O)[C@H](O)C(=O)O>>CC(C)C(=O)O[C@@H]1C(=O)OC(=O)[C@H]1OC(=O)C(C)C | C([C@@H](O)[C@H](O)C(=O)O)(=O)O.C(C(C)C)(=O)Cl>>O=C1OC([C@H]([C@@H]1OC(C(C)C)=O)OC(C(C)C)=O)=O | Cl[C:4]([CH:2]([CH3:1])[CH3:8])=[O:5].[OH:6][C@@H:17]([C@@H:13]([C:11]([OH:10])=[O:12])[OH:14])[C:15](=[O:9])[OH:16]>>[CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[O:6][C@@H:7]1[C:8](=[O:9])[O:10][C:11](=[O:12])[C@H:13]1[O:14][C:15](=[O:16])[CH:17]([CH3:18])[CH3:19] | CC(C)C(=O)Cl.O=C(O)[C@@H](O)[C@H](O)C(=O)O | CC(C)C(=O)O[C@@H]1C(=O)OC(=O)[C@H]1OC(=O)C(C)C | null | null | CCCCCC.CCOCC.C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 97e945862434d253355980141463740476b1aa5c4b8db8c31d16a34baf59ec6b | e0cfefbc9524ccf2e9a1480627bd015eb0fec489618391d800bcffef29909ee4 | O=C1CCC(=O)O1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3](-[C;D1;H3:4])-[CH3;D1;+0:5].[O;D1;H0:6]=[C:7](-[OH;D1;+0:8])-[C@@H;D3;+0:9](-[OH;D1;+0:10])-[C@H;D3;+0:11](-[OH;D1;+0:12])-[C;H0;D3;+0:13](=[O;H0;D1;+0:14])-[OH;D1;+0:15]>>[C;D1;H3:16]-[CH;D3;+0:11](-[C;D1;H3:17])-[C;H0;D3;+0:13](=[O;H0;D1;+0:15])-[O;H0;D2;+0:10]-[C@@H;D3;+0... | 71 | [{"value": 71.0, "product": "O=C1OC([C@H]([C@@H]1OC(C(C)C)=O)OC(C(C)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.6, "product": "O=C1OC([C@H]([C@@H]1OC(C(C)C)=O)OC(C(C)C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 22 | HOUR | To a suspension of D-tartaric acid (5.0 g, 33.3 mmol) in toluene (60 mL) was added isobutyryl chloride (11.3 mL, 107 mmol). The resulting suspension was heated to reflux and stirred for 22 h at reflux temperature. The reaction mixture was then concentrated in vacuo to afford a crystalline solid, which was suspended in ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Carboxylic acid.Carboxylic acid.Secondary alcohol.Secondary alcohol | Anhydride.Ester.Ester | null | C1CCOC1 | C1CCOC1 | null | CCCCCC.CCOCC.C1(=CC=CC=C1)C | null | 22 | CC(C)C(=O)Cl.O=C(O)[C@@H](O)[C@H](O)C(=O)O>CCCCCC.CCOCC.C1(=CC=CC=C1)C>CC(C)C(=O)O[C@@H]1C(=O)OC(=O)[C@H]1OC(=O)C(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0ff82f6f7829463cb3550f7d496a4e54 | CC(C)C(=O)O[C@@H]1C(=O)OC(=O)[C@H]1OC(=O)C(C)C.NO>>CC(C)C(=O)O[C@H]1C(=O)N(O)C(=O)[C@@H]1OC(=O)C(C)C | O=C1OC([C@H]([C@@H]1OC(C(C)C)=O)OC(C(C)C)=O)=O.NO>>ON1C([C@@H]([C@H](C1=O)OC(C(C)C)=O)OC(C(C)C)=O)=O | O1[C:8](=[O:9])[C@@H:7]([O:6][C:4]([CH:2]([CH3:1])[CH3:3])=[O:5])[C@H:14]([O:15][C:16](=[O:17])[CH:18]([CH3:19])[CH3:20])[C:12]1=[O:13].[NH2:10][OH:11]>>[CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[O:6][C@H:7]1[C:8](=[O:9])[N:10]([OH:11])[C:12](=[O:13])[C@@H:14]1[O:15][C:16](=[O:17])[CH:18]([CH3:19])[CH3:20] | CC(C)C(=O)O[C@@H]1C(=O)OC(=O)[C@H]1OC(=O)C(C)C.NO | CC(C)C(=O)O[C@H]1C(=O)N(O)C(=O)[C@@H]1OC(=O)C(C)C | null | null | C(C)(=O)OCC | Acylation | OtherReaction | ac5f63bba60d4a1d0330a86ebe6d3207e2dd9014985e5a45540d3ddb5de76511 | f570959c6614f83205be0ddef7485420f00ece3dc52d54ad514eee7326c7fc88 | O=C1CCC(=O)N1 | [NH2;D1;+0:1]-[O;D1;H1:2].[O;D1;H0:3]=[C;H0;D3;+0:4]1-O-[C;H0;D3;+0:5](=[O;D1;H0:6])-[C:7](-[#8:8]-[C:9]=[O;D1;H0:10])-[C:11]-1-[#8:12]-[C:13]=[O;D1;H0:14]>>[O;D1;H0:3]=[C;H0;D3;+0:4]1-[C:11](-[#8:12]-[C:13]=[O;D1;H0:14])-[C:7](-[#8:8]-[C:9]=[O;D1;H0:10])-[C;H0;D3;+0:5](=[O;D1;H0:6])-[N;H0;D3;+0:1]-1-[O;D1;H1:2] | 99.7 | [{"value": 99.7, "product": "ON1C([C@@H]([C@H](C1=O)OC(C(C)C)=O)OC(C(C)C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a stirred solution of compound (30) (5.98 g, 22 mmol) in ethyl acetate (50 mL) at 0° C. was added a 50% aqueous solution of hydroxylamine (1.75 g, 26.4 mmol). The resulting mixture was stirred at room temperature for 3 h and washed successively with aqueous citric acid solution and brine, then dried over anhydrous s... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Tertiary amide.Tertiary amide | C1CCOC1 | C1CC[NH]C1 | C1CC[NH]C1 | HO- | C(C)(=O)OCC | null | 3 | CC(C)C(=O)O[C@@H]1C(=O)OC(=O)[C@H]1OC(=O)C(C)C.NO>C(C)(=O)OCC>CC(C)C(=O)O[C@H]1C(=O)N(O)C(=O)[C@@H]1OC(=O)C(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-68d18f1c220342eb93c6beaf327191d9 | CC(C)(C)OC(=O)N(CCCl)CCCl.N#CCc1ccc(Br)cc1>>CC(C)(C)OC(=O)N1CCC(C#N)(c2ccc(Br)cc2)CC1 | C(C)(C)(C)OC(N(CCCl)CCCl)=O.BrC1=CC=C(C=C1)CC#N.[OH-].[Na+]>>C(C)(C)(C)OC(=O)N1CCC(CC1)(C#N)C1=CC=C(C=C1)Br | Cl[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:22][CH2:21]Cl.[CH2:11]([C:12]#[N:13])[c:14]1[cH:15][cH:16][c:17]([Br:18])[cH:19][cH:20]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11]([C:12]#[N:13])([c:14]2[cH:15][cH:16][c:17]([Br:18])[cH:19][cH:20]2)[CH2:21][C... | CC(C)(C)OC(=O)N(CCCl)CCCl.N#CCc1ccc(Br)cc1 | CC(C)(C)OC(=O)N1CCC(C#N)(c2ccc(Br)cc2)CC1 | null | [Br-].C(CCCCCCCCCCCCCCC)[P+](CCCC)(CCCC)CCCC | O.C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 43554b849de36f518831bb4a87fa13a0a0525fa0929a0f498da9e7a024251318 | 7b68950fc1047c59bb49c25e850f5a51cbe91a99bb87839c4547aec123110e4b | c1ccc(C2CCNCC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3](-[C:4]-[CH2;D2;+0:5]-Cl)-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12].[N;D1;H0:13]#[C:14]-[CH2;D2;+0:15]-[c:16](:[c:17]):[c:18]>>[C;D1;H3:10]-[C:9](-[C;D1;H3:11])(-[C;D1;H3:12])-[#8:8]-[C:6](=[O;D1;H0:7])-[#7:3]1-[C:4]-[CH2;D2;+0:5]-[C;H0;D4;+0:15](-[C:14]#[N... | 51.7 | [{"value": 51.7, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)(C#N)C1=CC=C(C=C1)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | null | null | To a mixture of bis-(2-chloro-ethyl)-carbamic acid tert-butyl ester from Step 1 (7.26 g, 30 mmol, 1 eq) and 4-bromophenylacetonitrile (5.88 g, 30 mmol, 1 eq) in 38 mL of toluene and 76 mL of H2O was added NaOH (45.6 g, 114 mmol, 10M solution) followed by hexadecyltributylphosphonium bromide (3.0 g, 6.0 mmol, 0.2 eq). T... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide | null | null | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1 | HCl | [Br-].C(CCCCCCCCCCCCCCC)[P+](CCCC)(CCCC)CCCC.O.C1(=CC=CC=C1)C | 110 | null | CC(C)(C)OC(=O)N(CCCl)CCCl.N#CCc1ccc(Br)cc1>[Br-].C(CCCCCCCCCCCCCCC)[P+](CCCC)(CCCC)CCCC.O.C1(=CC=CC=C1)C>CC(C)(C)OC(=O)N1CCC(C#N)(c2ccc(Br)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-26a28e9c09a047ae98dac8af6f50f05b | CC(C)(C)OC(=O)N1CCC(C#N)(c2ccc(Br)cc2)CC1.CO>>CC(C)(C)OC(=O)N1CCC(CC=O)(c2ccc(Br)cc2)CC1 | CO.C(C)(C)(C)OC(=O)N1CCC(CC1)(C#N)C1=CC=C(C=C1)Br.CC(C)C[AlH]CC(C)C>>C(C)(C)(C)OC(=O)N1CCC(CC1)(CC=O)C1=CC=C(C=C1)Br | N#[C:12][C:11]1([c:15]2[cH:16][cH:17][c:18]([Br:19])[cH:20][cH:21]2)[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:23][CH2:22]1.[CH3:13][OH:14]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11]([CH2:12][CH:13]=[O:14])([c:15]2[cH:16][cH:17][c:18]([Br:19])[cH:20][cH:... | CC(C)(C)OC(=O)N1CCC(C#N)(c2ccc(Br)cc2)CC1.CO | CC(C)(C)OC(=O)N1CCC(CC=O)(c2ccc(Br)cc2)CC1 | null | null | ClCCl | Acylation | OtherReaction | 45f1c96b0d061e9d88e0edbdf02ce532f16c290d610672bf6fe832ab076c9bba | 1c846c445000d2e843d2685c5a5c58e2e39afe4a0a6abbc76e5e576879a32701 | c1ccc(C2CCNCC2)cc1 | N#[C;H0;D2;+0:1]-[C:2](-[c:3])(-[C:4])-[C:5].[CH3;D1;+0:6]-[OH;D1;+0:7]>>[C:4]-[C:2](-[c:3])(-[CH2;D2;+0:1]-[CH;D2;+0:6]=[O;H0;D1;+0:7])-[C:5] | null | [] | null | null | 20 | HOUR | To a solution of 4-(4-bromo-phenyl)-4-cyano-piperidine-1-carboxylic acid tert-butyl ester from Step 2 (5.67 g, 15.57 mmol, 1 eq) in 60 mL of dichloromethane was add a solution of DIBAL-H (1M in toluene, 23.36 mL, 23.36 mmol, 1.5 eq) in a drop-wise fashion. The resulting mixture was stirred at room temperature for 20 h ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Methanol | Aldehyde | null | null | C1CC[NH]CC1.c1ccccc1 | Other | ClCCl | null | 20 | CC(C)(C)OC(=O)N1CCC(C#N)(c2ccc(Br)cc2)CC1.CO>ClCCl>CC(C)(C)OC(=O)N1CCC(CC=O)(c2ccc(Br)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5eb68b1997cb44899342858bcb169ea0 | CC(C)(C)OC(=O)N1CCC(CC=O)(c2ccc(Br)cc2)CC1>>CC(C)(C)OC(=O)N1CCC(CO)(c2ccc(Br)cc2)CC1 | C(C)(C)(C)OC(=O)N1CCC(CC1)(CC=O)C1=CC=C(C=C1)Br.[BH4-].[Na+].C(C)(C)O>>C(C)(C)(C)OC(=O)N1CCC(CC1)(CO)C1=CC=C(C=C1)Br | C([CH2:12][C:11]1([c:14]2[cH:15][cH:16][c:17]([Br:18])[cH:19][cH:20]2)[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:22][CH2:21]1)=[O:13]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11]([CH2:12][OH:13])([c:14]2[cH:15][cH:16][c:17]([Br:18])[cH:19][cH:20]2)[CH2:21]... | CC(C)(C)OC(=O)N1CCC(CC=O)(c2ccc(Br)cc2)CC1 | CC(C)(C)OC(=O)N1CCC(CO)(c2ccc(Br)cc2)CC1 | null | null | null | Miscellaneous | OtherReaction | 165ea33990c9cff6d94955cdaafab084da8c9def01a31e920214b7759117f6ff | 43cf4997d6e2488d8c69ca8bc684124ace6515563d3e08dcc47ef2a56dd17cc0 | c1ccc(C2CCNCC2)cc1 | [C:1]-[C:2](-[c:3])(-[CH2;D2;+0:4]-C=[O;H0;D1;+0:5])-[C:6]>>[C:1]-[C:2](-[c:3])(-[CH2;D2;+0:4]-[OH;D1;+0:5])-[C:6] | null | [] | null | null | 20 | HOUR | To a solution of 1.78 g of 4-(4-bromo-phenyl)-4-hydroxymethyl-piperidine-1-carboxylic acid tert-butyl ester from Step 3 (4.85 mmol, 1 eq) in 25 mL of isopropanol was added NaBH4 (0.201 g, 5.33 mmol, 1.1 eq). The mixture was stirred at room temperature for 20 h and then quenched by the addition of aqueous HCl (20 mL) to... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | C1CC[NH]CC1.c1ccccc1 | Other | null | null | 20 | CC(C)(C)OC(=O)N1CCC(CC=O)(c2ccc(Br)cc2)CC1>>CC(C)(C)OC(=O)N1CCC(CO)(c2ccc(Br)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e63f3163b5de49a88ff24da4241e7ea5 | CC(C)(C)OC(=O)N1CCC(c2ccc(Br)cc2)(C(COCC[Si](C)(C)C)Oc2nc3cc(Cl)c(Cl)cc3[nH]2)CC1.N#Cc1cccc(B(O)O)c1>>CC(C)(C)OC(=O)N1CCC(c2ccc(-c3cccc(C#N)c3)cc2)(C(COCC[Si](C)(C)C)Oc2nc3cc(Cl)c(Cl)cc3[nH]2)CC1 | C(C)(C)(C)OC(=O)N1CCC(CC1)(C(COCC[Si](C)(C)C)OC1=NC2=C(N1)C=C(C(=C2)Cl)Cl)C2=CC=C(C=C2)Br.C(#N)C=1C=C(C=CC1)B(O)O.C1(=CC=CC=C1)C.C(=O)([O-])[O-].[Na+].[Na+]>>C(C)(C)(C)OC(=O)N1CCC(CC1)(C(COCC[Si](C)(C)C)OC1=NC2=C(N1)C=C(C(=C2)Cl)Cl)C2=CC=C(C=C2)C2=CC(=CC=C2)C#N | Br[c:15]1[cH:14][cH:13][c:12]([C:11]2([CH:26]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:32])([CH3:33])[CH3:34])[O:35][c:36]3[n:37][c:38]4[cH:39][c:40]([Cl:41])[c:42]([Cl:43])[cH:44][c:45]4[nH:46]3)[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:48][CH2:47]2)[cH:25][cH:24]1.OB(O)[c:16]1[cH:17... | CC(C)(C)OC(=O)N1CCC(c2ccc(Br)cc2)(C(COCC[Si](C)(C)C)Oc2nc3cc(Cl)c(Cl)cc3[nH]2)CC1.N#Cc1cccc(B(O)O)c1 | CC(C)(C)OC(=O)N1CCC(c2ccc(-c3cccc(C#N)c3)cc2)(C(COCC[Si](C)(C)C)Oc2nc3cc(Cl)c(Cl)cc3[nH]2)CC1 | 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 | C(C)(=O)OCC.C(C)O | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc(C3(COc4nc5ccccc5[nH]4)CCNCC3)cc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 79.5 | [{"value": 79.5, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)(C(COCC[Si](C)(C)C)OC1=NC2=C(N1)C=C(C(=C2)Cl)Cl)C2=CC=C(C=C2)C2=CC(=CC=C2)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A mixture of 0.105 g of 4-(4-bromo-phenyl)-4-[5,6-dichloro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-yloxymethyl]-piperidine-1-carboxylic acid tert-butyl ester 51 (0.144 mmol, 1 eq), 0.024 g of 3-cyanophenyl boronic acid (0.16 mmol, 1.1 eq), and 0.034 g of Pd(PPh3)4 (0.03 mmol, 20 mol %) was mixed with 3 m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | C1CC[NH]CC1.c1ccccc1.c1ccccc1.c1ccc2[nH]cnc2c1 | 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.C(C)(=O)OCC.C(C)O | 80 | null | CC(C)(C)OC(=O)N1CCC(c2ccc(Br)cc2)(C(COCC[Si](C)(C)C)Oc2nc3cc(Cl)c(Cl)cc3[nH]2)CC1.N#Cc1cccc(B(O)O)c1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C(C)(=O)OCC.C(C)O>CC(C)(C)OC(=O)N1CCC(c2ccc(-c3c... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-488c2532ff4e4cd5b0402a9995a20f8e | CC(C)(C)OC(=O)N1CCC(c2ccc(-c3cccc(C#N)c3)cc2)(C(COCC[Si](C)(C)C)Oc2nc3cc(Cl)c(Cl)cc3[nH]2)CC1>>CC(C)(C)OC(=O)N1CCC(COc2nc3cc(Cl)c(Cl)cc3[nH]2)(c2ccc(-c3cccc(C#N)c3)cc2)CC1 | C(C)(C)(C)OC(=O)N1CCC(CC1)(C(COCC[Si](C)(C)C)OC1=NC2=C(N1)C=C(C(=C2)Cl)Cl)C2=CC=C(C=C2)C2=CC(=CC=C2)C#N.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>C(C)(C)(C)OC(=O)N1CCC(CC1)(COC1=NC2=C(N1)C=C(C(=C2)Cl)Cl)C2=CC=C(C=C2)C2=CC(=CC=C2)C#N | C[Si](C)(C)CCOC[CH:12]([C:11]1([c:25]2[cH:26][cH:27][c:28](-[c:29]3[cH:30][cH:31][cH:32][c:33]([C:34]#[N:35])[cH:36]3)[cH:37][cH:38]2)[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:40][CH2:39]1)[O:13][c:14]1[n:15][c:16]2[cH:17][c:18]([Cl:19])[c:20]([Cl:21])[cH:22][c:23]2[nH:24]1>>[CH3:1][C:2... | CC(C)(C)OC(=O)N1CCC(c2ccc(-c3cccc(C#N)c3)cc2)(C(COCC[Si](C)(C)C)Oc2nc3cc(Cl)c(Cl)cc3[nH]2)CC1 | CC(C)(C)OC(=O)N1CCC(COc2nc3cc(Cl)c(Cl)cc3[nH]2)(c2ccc(-c3cccc(C#N)c3)cc2)CC1 | null | null | O1CCCC1 | Reduction | OtherReaction | d69c6d61640e32f10824c7c1514f3119c2d4874c1389751d2577a99972bf959d | 9abd1fd0aee638213302f50e544d5b4119741bd519771ef99d13ceeb790018fc | c1ccc(-c2ccc(C3(COc4nc5ccccc5[nH]4)CCNCC3)cc2)cc1 | C-[Si](-C)(-C)-C-C-O-C-[CH;D3;+0:1](-[#8:2]-[c:3](:[#7;a:4]):[#7;a:5])-[C:6](-[c:7])(-[C:8])-[C:9]>>[#7;a:4]:[c:3](-[#8:2]-[CH2;D2;+0:1]-[C:6](-[c:7])(-[C:8])-[C:9]):[#7;a:5] | 52.7 | [{"value": 52.7, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)(COC1=NC2=C(N1)C=C(C(=C2)Cl)Cl)C2=CC=C(C=C2)C2=CC(=CC=C2)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | To a solution of 0.081 g of 4-(3′-cyano-biphenyl-4-yl)-4-[5,6-dichloro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-yloxymethyl]-piperidine-1-carboxylic acid tert-butyl ester 52 (0.115 mmol) in 5 mL of tetrahydrofuran at room temperature was added 0.23 mL of a solution of TBAF (1M in THF, 0.23 mmol, 2 eq). Th... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Silyl protective group | Ether | null | null | C1CC[NH]CC1.c1ccc2[nH]cnc2c1.c1ccccc1.c1ccccc1 | HO- | O1CCCC1 | 60 | null | CC(C)(C)OC(=O)N1CCC(c2ccc(-c3cccc(C#N)c3)cc2)(C(COCC[Si](C)(C)C)Oc2nc3cc(Cl)c(Cl)cc3[nH]2)CC1>O1CCCC1>CC(C)(C)OC(=O)N1CCC(COc2nc3cc(Cl)c(Cl)cc3[nH]2)(c2ccc(-c3cccc(C#N)c3)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-833505e716b6420083758a04c4baeb6d | CC(C)(C)OC(=O)N1CCC(COc2nc3cc(Cl)c(Cl)cc3[nH]2)(c2ccc(-c3cccc(C#N)c3)cc2)CC1>>N#Cc1cccc(-c2ccc(C3(COc4nc5cc(Cl)c(Cl)cc5[nH]4)CCNCC3)cc2)c1 | C(C)(C)(C)OC(=O)N1CCC(CC1)(COC1=NC2=C(N1)C=C(C(=C2)Cl)Cl)C2=CC=C(C=C2)C2=CC(=CC=C2)C#N.FC(C(=O)O)(F)F>>ClC1=CC2=C(NC(=N2)OCC2(CCNCC2)C2=CC=C(C=C2)C2=CC(=CC=C2)C#N)C=C1Cl | CC(C)(C)OC(=O)[N:28]1[CH2:27][CH2:26][C:12]([c:11]2[cH:10][cH:9][c:8](-[c:7]3[cH:6][cH:5][cH:4][c:3]([C:2]#[N:1])[cH:33]3)[cH:32][cH:31]2)([CH2:13][O:14][c:15]2[n:16][c:17]3[cH:18][c:19]([Cl:20])[c:21]([Cl:22])[cH:23][c:24]3[nH:25]2)[CH2:30][CH2:29]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11](... | CC(C)(C)OC(=O)N1CCC(COc2nc3cc(Cl)c(Cl)cc3[nH]2)(c2ccc(-c3cccc(C#N)c3)cc2)CC1 | N#Cc1cccc(-c2ccc(C3(COc4nc5cc(Cl)c(Cl)cc5[nH]4)CCNCC3)cc2)c1 | null | null | ClCCl.C1(=CC=CC=C1)C | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(-c2ccc(C3(COc4nc5ccccc5[nH]4)CCNCC3)cc2)cc1 | 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] | 91 | [{"value": 91.0, "product": "ClC1=CC2=C(NC(=N2)OCC2(CCNCC2)C2=CC=C(C=C2)C2=CC(=CC=C2)C#N)C=C1Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | To a solution of 0.015 g of 4-(3′-cyano-biphenyl-4-yl)-4-(5,6-dichloro-1H-benzoimidazol-2-yloxymethyl)-piperidine-1-carboxylic acid tert-butyl ester 53 (0.026 mmol) in 3 mL of dichloromethane at 0° C. was added 1 mL of trifluoroacetic acid. The mixture was stirred at 0° C. for 2 h then diluted with 10 mL of toluene and... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccccc1.c1ccccc1.c1ccc2[nH]cnc2c1.C1CCNCC1 | HO- | ClCCl.C1(=CC=CC=C1)C | 0 | 2 | CC(C)(C)OC(=O)N1CCC(COc2nc3cc(Cl)c(Cl)cc3[nH]2)(c2ccc(-c3cccc(C#N)c3)cc2)CC1>ClCCl.C1(=CC=CC=C1)C>N#Cc1cccc(-c2ccc(C3(COc4nc5cc(Cl)c(Cl)cc5[nH]4)CCNCC3)cc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1b2ab63d2f4d41b7b48473b6d268090e | CS(=O)(=O)Cl.C[Si](C)(C)CCOCC(Oc1nc2cc(Cl)c(Cl)cc2[nH]1)C1(c2ccc(-c3cccc(C#N)c3)cc2)CCNCC1>>C[Si](C)(C)CCOCC(Oc1nc2cc(Cl)c(Cl)cc2[nH]1)C1(c2ccc(-c3cccc(C#N)c3)cc2)CCN(S(C)(=O)=O)CC1 | ClC1=CC2=C(NC(=N2)OC(COCC[Si](C)(C)C)C2(CCNCC2)C2=CC=C(C=C2)C2=CC(=CC=C2)C#N)C=C1Cl.CS(=O)(=O)Cl.CCN(C(C)C)C(C)C>>ClC1=CC2=C(NC(=N2)OC(COCC[Si](C)(C)C)C2(CCN(CC2)S(=O)(=O)C)C2=CC=C(C=C2)C2=CC(=CC=C2)C#N)C=C1Cl | Cl[S:40]([CH3:41])(=[O:42])=[O:43].[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][O:7][CH2:8][CH:9]([O:10][c:11]1[n:12][c:13]2[cH:14][c:15]([Cl:16])[c:17]([Cl:18])[cH:19][c:20]2[nH:21]1)[C:22]1([c:23]2[cH:24][cH:25][c:26](-[c:27]3[cH:28][cH:29][cH:30][c:31]([C:32]#[N:33])[cH:34]3)[cH:35][cH:36]2)[CH2:37][CH2:38][NH:39][... | CS(=O)(=O)Cl.C[Si](C)(C)CCOCC(Oc1nc2cc(Cl)c(Cl)cc2[nH]1)C1(c2ccc(-c3cccc(C#N)c3)cc2)CCNCC1 | C[Si](C)(C)CCOCC(Oc1nc2cc(Cl)c(Cl)cc2[nH]1)C1(c2ccc(-c3cccc(C#N)c3)cc2)CCN(S(C)(=O)=O)CC1 | null | null | ClCCl.C(C)(=O)OCC | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | d63e07b47df62aebedb35134f6d0504cfcbed5ccfdec31c2c42bba6875c15fe7 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | c1ccc(-c2ccc(C3(COc4nc5ccccc5[nH]4)CCNCC3)cc2)cc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4])-[C:8]-[C:9] | 128.3 | [{"value": 128.3, "product": "ClC1=CC2=C(NC(=N2)OC(COCC[Si](C)(C)C)C2(CCN(CC2)S(=O)(=O)C)C2=CC=C(C=C2)C2=CC(=CC=C2)C#N)C=C1Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of 0.030 g of 4′-{4-[5,6-dichloro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-yloxymethyl]-piperidin-4-yl}-biphenyl-3-carbonitrile (0.05 mmol) 55 in 1 mL of dichloromethane was added methanesulfonyl chloride (0.005 mL, 0.053 mmol, 1.1 eq) and DIEA (0.011 mL, 0.06 mmol, 1.2 eq). The resulting mi... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccc2[nH]cnc2c1.c1ccccc1.c1ccccc1.C1CC[NH]CC1 | HCl | ClCCl.C(C)(=O)OCC | null | 16 | CS(=O)(=O)Cl.C[Si](C)(C)CCOCC(Oc1nc2cc(Cl)c(Cl)cc2[nH]1)C1(c2ccc(-c3cccc(C#N)c3)cc2)CCNCC1>ClCCl.C(C)(=O)OCC>C[Si](C)(C)CCOCC(Oc1nc2cc(Cl)c(Cl)cc2[nH]1)C1(c2ccc(-c3cccc(C#N)c3)cc2)CCN(S(C)(=O)=O)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fb978749489047c8a4be6a0bfb025eb6 | C[Si](C)(C)CCOCC(Oc1nc2cc(Cl)c(Cl)cc2[nH]1)C1(c2ccc(-c3cccc(C#N)c3)cc2)CCN(S(C)(=O)=O)CC1>>CS(=O)(=O)N1CCC(COc2nc3cc(Cl)c(Cl)cc3[nH]2)(c2ccc(-c3cccc(C#N)c3)cc2)CC1 | ClC1=CC2=C(NC(=N2)OC(COCC[Si](C)(C)C)C2(CCN(CC2)S(=O)(=O)C)C2=CC=C(C=C2)C2=CC(=CC=C2)C#N)C=C1Cl.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>ClC1=CC2=C(NC(=N2)OCC2(CCN(CC2)S(=O)(=O)C)C2=CC=C(C=C2)C2=CC(=CC=C2)C#N)C=C1Cl | C[Si](C)(C)CCOC[CH:9]([C:8]1([c:22]2[cH:23][cH:24][c:25](-[c:26]3[cH:27][cH:28][cH:29][c:30]([C:31]#[N:32])[cH:33]3)[cH:34][cH:35]2)[CH2:7][CH2:6][N:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH2:37][CH2:36]1)[O:10][c:11]1[n:12][c:13]2[cH:14][c:15]([Cl:16])[c:17]([Cl:18])[cH:19][c:20]2[nH:21]1>>[CH3:1][S:2](=[O:3])(=[O:4])[N:5]1... | C[Si](C)(C)CCOCC(Oc1nc2cc(Cl)c(Cl)cc2[nH]1)C1(c2ccc(-c3cccc(C#N)c3)cc2)CCN(S(C)(=O)=O)CC1 | CS(=O)(=O)N1CCC(COc2nc3cc(Cl)c(Cl)cc3[nH]2)(c2ccc(-c3cccc(C#N)c3)cc2)CC1 | null | null | O1CCCC1.C(C)(=O)OCC | Reduction | OtherReaction | d69c6d61640e32f10824c7c1514f3119c2d4874c1389751d2577a99972bf959d | 9abd1fd0aee638213302f50e544d5b4119741bd519771ef99d13ceeb790018fc | c1ccc(-c2ccc(C3(COc4nc5ccccc5[nH]4)CCNCC3)cc2)cc1 | C-[Si](-C)(-C)-C-C-O-C-[CH;D3;+0:1](-[#8:2]-[c:3](:[#7;a:4]):[#7;a:5])-[C:6](-[c:7])(-[C:8])-[C:9]>>[#7;a:4]:[c:3](-[#8:2]-[CH2;D2;+0:1]-[C:6](-[c:7])(-[C:8])-[C:9]):[#7;a:5] | 44.9 | [{"value": 44.9, "product": "ClC1=CC2=C(NC(=N2)OCC2(CCN(CC2)S(=O)(=O)C)C2=CC=C(C=C2)C2=CC(=CC=C2)C#N)C=C1Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | To a solution of 0.044 g of crude 4′-{4-[5,6-dichloro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-yloxymethyl]-1-methanesulfonyl-piperidin-4-yl}-biphenyl-3-carbonitrile from the previous step (˜0.05 mmol) in 2 mL of tetrahydrofuran was added tetrabutylammonium fluoride (1M in THF, 0.1 mL, 0.1 mmol, 2 eq) and... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Silyl protective group | Ether | null | null | C1CC[NH]CC1.c1ccc2[nH]cnc2c1.c1ccccc1.c1ccccc1 | HO- | O1CCCC1.C(C)(=O)OCC | 60 | null | C[Si](C)(C)CCOCC(Oc1nc2cc(Cl)c(Cl)cc2[nH]1)C1(c2ccc(-c3cccc(C#N)c3)cc2)CCN(S(C)(=O)=O)CC1>O1CCCC1.C(C)(=O)OCC>CS(=O)(=O)N1CCC(COc2nc3cc(Cl)c(Cl)cc3[nH]2)(c2ccc(-c3cccc(C#N)c3)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-964e54fb5eef4dc182fd8e148150cfcc | C[Si](C)(C)CCOCC(Oc1nc2cc(Cl)c(Cl)cc2[nH]1)C1(c2ccc(-c3cccc(C#N)c3)cc2)CCNCC1.O=CC1CC1>>N#Cc1cccc(-c2ccc(C3(COc4nc5cc(Cl)c(Cl)cc5[nH]4)CCN(CC4CC4)CC3)cc2)c1 | [F-].C(CCC)[N+](CCCC)(CCCC)CCCC.ClC1=CC2=C(NC(=N2)OC(COCC[Si](C)(C)C)C2(CCNCC2)C2=CC=C(C=C2)C2=CC(=CC=C2)C#N)C=C1Cl.C1(CC1)C=O.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]>>C1(CC1)CN1CCC(CC1)(COC1=NC2=C(N1)C=C(C(=C2)Cl)Cl)C2=CC=C(C=C2)C2=CC(=CC=C2)C#N | C[Si](C)(C)CCOC[CH:13]([C:12]1([c:11]2[cH:10][cH:9][c:8](-[c:7]3[cH:6][cH:5][cH:4][c:3]([C:2]#[N:1])[cH:37]3)[cH:36][cH:35]2)[CH2:26][CH2:27][NH:28][CH2:33][CH2:34]1)[O:14][c:15]1[n:16][c:17]2[cH:18][c:19]([Cl:20])[c:21]([Cl:22])[cH:23][c:24]2[nH:25]1.O=[CH:29][CH:30]1[CH2:31][CH2:32]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH... | C[Si](C)(C)CCOCC(Oc1nc2cc(Cl)c(Cl)cc2[nH]1)C1(c2ccc(-c3cccc(C#N)c3)cc2)CCNCC1.O=CC1CC1 | N#Cc1cccc(-c2ccc(C3(COc4nc5cc(Cl)c(Cl)cc5[nH]4)CCN(CC4CC4)CC3)cc2)c1 | null | null | O1CCCC1.C(C)(=O)O.ClCCCl | Heteroatom Alkylation and Arylation | OtherReaction | e0f1d8750a019670f4994afcb1f27f4754623b9b5337e7e6204abafbfacdbec3 | b742e0f5cea8d7b3d9fda93d9d894c14daa01ac5e15c5823be8f1ecad641ca82 | c1ccc(-c2ccc(C3(COc4nc5ccccc5[nH]4)CCN(CC4CC4)CC3)cc2)cc1 | C-[Si](-C)(-C)-C-C-O-C-[CH;D3;+0:1](-[#8:2]-[c:3](:[#7;a:4]):[#7;a:5])-[C:6]1(-[c:7])-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1.O=[CH;D2;+0:13]-[C:14]1-[C:15]-[C:16]-1>>[#7;a:4]:[c:3](-[#8:2]-[CH2;D2;+0:1]-[C:6]1(-[c:7])-[C:8]-[C:9]-[N;H0;D3;+0:10](-[CH2;D2;+0:13]-[C:14]2-[C:15]-[C:16]-2)-[C:11]-[C:12]-1):[#7;a:5] | 18 | [{"value": 18.0, "product": "C1(CC1)CN1CCC(CC1)(COC1=NC2=C(N1)C=C(C(=C2)Cl)Cl)C2=CC=C(C=C2)C2=CC(=CC=C2)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 0.045 g of 4′-{4-[5,6-dichloro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-yloxymethyl]-piperidin-4-yl}-biphenyl-3-carbonitrile 55 (0.073 mmol, 1 eq) in 0.5 mL of 1,2-dichloroethane at room temperature was added 6.6 μL of cyclopropanecarboxaldehyde (0.088 mmol, 1.2 eq) and acetic acid (0.005... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ether.Ether.Secondary amine.Silyl protective group | Ether.Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.c1ccccc1.c1ccc2[nH]cnc2c1.C1CC[NH]CC1.C1CC1 | HO- | O1CCCC1.C(C)(=O)O.ClCCCl | null | 1 | C[Si](C)(C)CCOCC(Oc1nc2cc(Cl)c(Cl)cc2[nH]1)C1(c2ccc(-c3cccc(C#N)c3)cc2)CCNCC1.O=CC1CC1>O1CCCC1.C(C)(=O)O.ClCCCl>N#Cc1cccc(-c2ccc(C3(COc4nc5cc(Cl)c(Cl)cc5[nH]4)CCN(CC4CC4)CC3)cc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-63d2c51d78ef4c92b9fdbf9eed4b7d71 | CCN=C=O.C[Si](C)(C)CCOCC(Oc1nc2cc(Cl)c(Cl)cc2[nH]1)C1(c2ccc(-c3cccc(C#N)c3)cc2)CCNCC1>>CCNC(=O)N1CCC(c2ccc(-c3cccc(C#N)c3)cc2)(C(COCC[Si](C)(C)C)Oc2nc3cc(Cl)c(Cl)cc3[nH]2)CC1 | ClC1=CC2=C(NC(=N2)OC(COCC[Si](C)(C)C)C2(CCNCC2)C2=CC=C(C=C2)C2=CC(=CC=C2)C#N)C=C1Cl.C(C)N=C=O.C(C)(C)N(CC)C(C)C>>C(C)NC(=O)N1CCC(CC1)(C(COCC[Si](C)(C)C)OC1=NC2=C(N1)C=C(C(=C2)Cl)Cl)C2=CC=C(C=C2)C2=CC(=CC=C2)C#N | [CH3:1][CH2:2][N:3]=[C:4]=[O:5].[NH:6]1[CH2:7][CH2:8][C:9]([c:10]2[cH:11][cH:12][c:13](-[c:14]3[cH:15][cH:16][cH:17][c:18]([C:19]#[N:20])[cH:21]3)[cH:22][cH:23]2)([CH:24]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:30])([CH3:31])[CH3:32])[O:33][c:34]2[n:35][c:36]3[cH:37][c:38]([Cl:39])[c:40]([Cl:41])[cH:42][c:43]3[nH:44... | CCN=C=O.C[Si](C)(C)CCOCC(Oc1nc2cc(Cl)c(Cl)cc2[nH]1)C1(c2ccc(-c3cccc(C#N)c3)cc2)CCNCC1 | CCNC(=O)N1CCC(c2ccc(-c3cccc(C#N)c3)cc2)(C(COCC[Si](C)(C)C)Oc2nc3cc(Cl)c(Cl)cc3[nH]2)CC1 | null | null | ClCCl | Acylation | Urea synthesis via isocyanate and secondary amine | 6a88f2fb12498f30b6ca536d46572ea3e28c2b70ddb4a5e5b0a05fe1e5e9bb8d | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | c1ccc(-c2ccc(C3(COc4nc5ccccc5[nH]4)CCNCC3)cc2)cc1 | [C;D1;H3:1]-[C:2]-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:3]-[C:2]-[C;D1;H3:1])-[C:9]-[C:10] | 60.5 | [{"value": 60.5, "product": "C(C)NC(=O)N1CCC(CC1)(C(COCC[Si](C)(C)C)OC1=NC2=C(N1)C=C(C(=C2)Cl)Cl)C2=CC=C(C=C2)C2=CC(=CC=C2)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of 0.045 g of 4′-{4-[5,6-dichloro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-yloxymethyl]-piperidin-4-yl}-biphenyl-3-carbonitrile (0.073 mmol, 1 eq) in 0.7 mL of dichloromethane was added ethyl isocyanate (6.5 μL, 0.088 mmol, 1.2 eq) and 15.4 μL of diisopropylethyl amine (0.088 mmol, 1.2 eq) a... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.c1ccccc1.c1ccc2[nH]cnc2c1 | null | ClCCl | null | 16 | CCN=C=O.C[Si](C)(C)CCOCC(Oc1nc2cc(Cl)c(Cl)cc2[nH]1)C1(c2ccc(-c3cccc(C#N)c3)cc2)CCNCC1>ClCCl>CCNC(=O)N1CCC(c2ccc(-c3cccc(C#N)c3)cc2)(C(COCC[Si](C)(C)C)Oc2nc3cc(Cl)c(Cl)cc3[nH]2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aa810b331fbb4e18a986c0027bc5c8c1 | Nc1ccc(F)c(F)c1N.O=C(O)CCl>>Fc1cc2nc(CCl)[nH]c2cc1F | FC=1C(=C(C=CC1F)N)N.ClCC(=O)O.[NH4+].[OH-]>>ClCC1=NC2=C(N1)C=C(C(=C2)F)F | [F:1][c:2]1[cH:3][cH:4][c:10]([NH2:9])[c:11]([NH2:5])[c:12]1[F:13].O=[C:6](O)[CH2:7][Cl:8]>>[F:1][c:2]1[cH:3][c:4]2[n:5][c:6]([CH2:7][Cl:8])[nH:9][c:10]2[cH:11][c:12]1[F:13] | Nc1ccc(F)c(F)c1N.O=C(O)CCl | Fc1cc2nc(CCl)[nH]c2cc1F | null | null | Cl | Aromatic Heterocycle Formation | OtherReaction | 8409c8c0d4e4ea3a5ac4d357a90931cd25bdeaf070f3095e8e16fa38a40808ca | 7e1f92e04d2c8ce23daa6dd33c69b56cfa9feb423ec9a3444bfeb568a99ef87e | c1ccc2[nH]cnc2c1 | O-[C;H0;D3;+0:1](=O)-[C:2]-[Cl;D1;H0:3].[F;D1;H0:4]-[c:5]1:[c:6]:[c:7]:[cH;D2;+0:8]:[c:9](-[NH2;D1;+0:10]):[c;H0;D3;+0:11]:1-[NH2;D1;+0:12]>>[Cl;D1;H0:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:12]:[c;H0;D3;+0:8]2:[c:7]:[c:6]:[c:5](-[F;D1;H0:4]):[cH;D2;+0:11]:[c:9]:2:[nH;D2;+0:10]:1 | null | [] | 100 | CELSIUS | null | null | A mixture of 1 g of 3,4-difluoro-1,2-phenylenediamine (6.94 mmol) and 0.983 g of chloro-acetic acid (10.41 mmol, 1.5 eq) in 13 mL of 4N aqueous HCl was heated to 100° C. for 3 h. The mixture was poured onto ice (10 g), neutralized by the addition of NH4OH and extracted with three 30 mL portions of ethyl acetate. The or... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine.Primary amine | null | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | HO- | Cl | 100 | null | Nc1ccc(F)c(F)c1N.O=C(O)CCl>Cl>Fc1cc2nc(CCl)[nH]c2cc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-55e345f3f73544e9a35091cfc8780b6a | CC(C)(C)OC(=O)N1CCC(OCc2nc3cc(F)c(F)cc3n2COCC[Si](C)(C)C)(c2ccc(Br)cc2)CC1.N#Cc1cccc(B(O)O)c1>>CC(C)(C)OC(=O)N1CCC(OCc2nc3cc(F)c(F)cc3n2COCC[Si](C)(C)C)(c2ccc(-c3cccc(C#N)c3)cc2)CC1 | C(C)(C)(C)OC(=O)N1CCC(CC1)(OCC1=NC2=C(N1COCC[Si](C)(C)C)C=C(C(=C2)F)F)C2=CC=C(C=C2)Br.C(#N)C=1C=C(C=CC1)B(O)O.C1(=CC=CC=C1)C.C(=O)([O-])[O-].[Na+].[Na+]>>C(C)(C)(C)OC(=O)N1CCC(CC1)(OCC1=NC2=C(N1COCC[Si](C)(C)C)C=C(C(=C2)F)F)C2=CC=C(C=C2)C2=CC(=CC=C2)C#N | Br[c:36]1[cH:35][cH:34][c:33]([C:11]2([O:12][CH2:13][c:14]3[n:15][c:16]4[cH:17][c:18]([F:19])[c:20]([F:21])[cH:22][c:23]4[n:24]3[CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:30])([CH3:31])[CH3:32])[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:48][CH2:47]2)[cH:46][cH:45]1.OB(O)[c:37]1[cH:38][cH... | CC(C)(C)OC(=O)N1CCC(OCc2nc3cc(F)c(F)cc3n2COCC[Si](C)(C)C)(c2ccc(Br)cc2)CC1.N#Cc1cccc(B(O)O)c1 | CC(C)(C)OC(=O)N1CCC(OCc2nc3cc(F)c(F)cc3n2COCC[Si](C)(C)C)(c2ccc(-c3cccc(C#N)c3)cc2)CC1 | 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 | C(C)(=O)OCC.C(C)O | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc(C3(OCc4nc5ccccc5[nH]4)CCNCC3)cc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 34.6 | [{"value": 34.6, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)(OCC1=NC2=C(N1COCC[Si](C)(C)C)C=C(C(=C2)F)F)C2=CC=C(C=C2)C2=CC(=CC=C2)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A mixture of 0.116 g of 4-(4-bromo-phenyl)-4-[5,6-difluoro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-ylmethoxy]-piperidine-1-carboxylic acid tert-butyl ester 61 (˜0.18 mmol, 1 eq), 0.032 g of 3-cyanophenylboronic acid (0.215 mmol, 1.2 eq), and 0.040 g of Pd(PPh3)4 (0.036 mmol, 20 mol %) with 3 mL of toluen... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | C1CC[NH]CC1.c1ccc2[nH]cnc2c1.c1ccccc1.c1ccccc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C(C)(=O)OCC.C(C)O | 80 | null | CC(C)(C)OC(=O)N1CCC(OCc2nc3cc(F)c(F)cc3n2COCC[Si](C)(C)C)(c2ccc(Br)cc2)CC1.N#Cc1cccc(B(O)O)c1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C(C)(=O)OCC.C(C)O>CC(C)(C)OC(=O)N1CCC(OCc2nc3cc(F)c(F)c... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7a22537c5391467097cb0b6136ff66c5 | CC(C)(C)OC(=O)N1CCC(OCc2nc3cc(F)c(F)cc3n2COCC[Si](C)(C)C)(c2ccc(-c3cccc(C#N)c3)cc2)CC1>>CC(C)(C)OC(=O)N1CCC(OCc2nc3cc(F)c(F)cc3[nH]2)(c2ccc(-c3cccc(C#N)c3)cc2)CC1 | C(C)(C)(C)OC(=O)N1CCC(CC1)(OCC1=NC2=C(N1COCC[Si](C)(C)C)C=C(C(=C2)F)F)C2=CC=C(C=C2)C2=CC(=CC=C2)C#N.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>C(C)(C)(C)OC(=O)N1CCC(CC1)(OCC1=NC2=C(N1)C=C(C(=C2)F)F)C2=CC=C(C=C2)C2=CC(=CC=C2)C#N | C[Si](C)(C)CCOC[n:24]1[c:14]([CH2:13][O:12][C:11]2([c:25]3[cH:26][cH:27][c:28](-[c:29]4[cH:30][cH:31][cH:32][c:33]([C:34]#[N:35])[cH:36]4)[cH:37][cH:38]3)[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:40][CH2:39]2)[n:15][c:16]2[cH:17][c:18]([F:19])[c:20]([F:21])[cH:22][c:23]21>>[CH3:1][C:2](... | CC(C)(C)OC(=O)N1CCC(OCc2nc3cc(F)c(F)cc3n2COCC[Si](C)(C)C)(c2ccc(-c3cccc(C#N)c3)cc2)CC1 | CC(C)(C)OC(=O)N1CCC(OCc2nc3cc(F)c(F)cc3[nH]2)(c2ccc(-c3cccc(C#N)c3)cc2)CC1 | null | null | O1CCCC1 | Reduction | OtherReaction | 8ce938c26df2ac3f48612e5a6fef893f0e283c99585c8225bd849efe3babbf31 | d646edd3b1165ce8eea24b0587d24c565cf6371928b4879100704e7b3cd85ed9 | c1ccc(-c2ccc(C3(OCc4nc5ccccc5[nH]4)CCNCC3)cc2)cc1 | C-[Si](-C)(-C)-C-C-O-C-[n;H0;D3;+0:1]1:[c:2](-[C:3]):[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]>>[C:3]-[c:2]1:[#7;a:4]:[c:5](:[c:6]):[c:7](:[c:8]):[nH;D2;+0:1]:1 | 91.8 | [{"value": 91.8, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)(OCC1=NC2=C(N1)C=C(C(=C2)F)F)C2=CC=C(C=C2)C2=CC(=CC=C2)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | To a solution of 0.033 g of 4-(3′-cyano-biphenyl-4-yl)-4-[5,6-difluoro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-ylmethoxy]-piperidine-1-carboxylic acid tert-butyl ester 62 (0.05 mmol, 1 eq) in 2.5 mL of tetrahydrofuran was added 0.10 mL tetrabutylammonium fluoride (1M in THF, 0.1 mmol, 2 eq). The reaction... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Silyl protective group | null | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | C1CC[NH]CC1.c1ccc2[nH]cnc2c1.c1ccccc1.c1ccccc1 | HO- | O1CCCC1 | null | 20 | CC(C)(C)OC(=O)N1CCC(OCc2nc3cc(F)c(F)cc3n2COCC[Si](C)(C)C)(c2ccc(-c3cccc(C#N)c3)cc2)CC1>O1CCCC1>CC(C)(C)OC(=O)N1CCC(OCc2nc3cc(F)c(F)cc3[nH]2)(c2ccc(-c3cccc(C#N)c3)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-931b01742a32446eb694fb362358701e | CN(C)C(=O)Nc1ccc(Cl)c(Cl)c1>>c1ccc2[nH]cnc2c1 | [Na+].[Cl-].CN(C)C(=O)NC1=CC(=C(C=C1)Cl)Cl>>N1=CNC2=C1C=CC=C2 | C[N:7](C)[C:6](=O)[NH:5][c:4]1[cH:3][cH:2][c:1](Cl)[c:9](Cl)[cH:8]1>>[cH:1]1[cH:2][cH:3][c:4]2[nH:5][cH:6][n:7][c:8]2[cH:9]1 | CN(C)C(=O)Nc1ccc(Cl)c(Cl)c1 | c1ccc2[nH]cnc2c1 | null | null | C1CN(CCN1CCO)CCS(=O)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 4b372c4c7c90bef11a8b0c0147525f09ed44e0119c81816cf4f8dc873965ec8d | dca93e981fd4c868d915c45e7b938878dd6a6445868958886d6ebf14ffc0aeb1 | c1ccc2[nH]cnc2c1 | C-[N;H0;D3;+0:1](-C)-[C;H0;D3;+0:2](=O)-[NH;D2;+0:3]-[c:4]1:[c:5]:[c:6]:[c;H0;D3;+0:7](-Cl):[c;H0;D3;+0:8](-Cl):[cH;D2;+0:9]:1>>[c:6]1:[c:5]:[c:4]2:[nH;D2;+0:3]:[cH;D2;+0:2]:[n;H0;D2;+0:1]:[c;H0;D3;+0:9]:2:[cH;D2;+0:8]:[cH;D2;+0:7]:1 | null | [] | null | null | 2 | HOUR | Membranes from CHO cells expressing the MCH receptor were prepared by lysing cells with 5 mM HEPES for 15 min at 4C. Cell lysates were centrifuged (12.5000×g, 15 min) and the pellet was resuspended in 5 mM HEPES. For each 96-well plate (Microlite, Dynex Technologies), 1 mg of cell membranes were incubated with 10 mg of... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Urea | null | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1 | HCl | C1CN(CCN1CCO)CCS(=O)(=O)O | null | 2 | CN(C)C(=O)Nc1ccc(Cl)c(Cl)c1>C1CN(CCN1CCO)CCS(=O)(=O)O>c1ccc2[nH]cnc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6d5bfc90160043f68888851e29fd8bec | COc1cccc([N+](=O)[O-])c1C>>COc1cccc(N)c1C | CC#N.O.CC1=C(C=CC=C1[N+](=O)[O-])OC.C(=O)(C(F)(F)F)O>>CC1=C(N)C=CC=C1OC | O=[N+:8]([O-])[c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[c:9]1[CH3:10]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH2:8])[c:9]1[CH3:10] | COc1cccc([N+](=O)[O-])c1C | COc1cccc(N)c1C | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 98 | [{"value": 98.0, "product": "CC1=C(N)C=CC=C1OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2-methyl-3-nitro anisole which is commercially available (1a1) (5.1 g; 30.33 mmol; requires ˜30 min. to dissolve) in absolute ethanol (85 mL) was added 10% Pd/C catalyst (500 mg). The solution was hydrogenated under a hydrogen filled balloon at atmospheric pressure and room temperature for 19 h. The re... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Pd].C(C)O | null | null | COc1cccc([N+](=O)[O-])c1C>[Pd].C(C)O>COc1cccc(N)c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-74e9c1b9605a44ce85afd682f94646e1 | Br.Nc1c(O)cccc1[N+](=O)[O-]>>O=[N+]([O-])c1cccc(O)c1Br | Br.NC1=C(C=CC=C1[N+](=O)[O-])O.Br.N(=O)[O-].[Na+]>>BrC1=C(C=CC=C1[N+](=O)[O-])O | [BrH:11].N[c:10]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][cH:6][cH:7][c:8]1[OH:9]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([OH:9])[c:10]1[Br:11] | Br.Nc1c(O)cccc1[N+](=O)[O-] | O=[N+]([O-])c1cccc(O)c1Br | null | null | O1CCOCC1.O | Miscellaneous | OtherReaction | 976fb3f0996203ccf639edc3dd63ebf792dabe502fe07eb66206f5ee630d746b | 1129c10513c603d2647e51dd9713063aaf10bd8a364ed275b9b93c32624e3ba4 | c1ccccc1 | N-[c;H0;D3;+0:1](:[c:2](-[#7;+:3]):[c:4]):[c:5](-[O;D1;H1:6]):[c:7].[BrH;D0;+0:8]>>[#7;+:3]-[c:2](:[c:4]):[c;H0;D3;+0:1](-[Br;H0;D1;+0:8]):[c:5](-[O;D1;H1:6]):[c:7] | null | [] | 0 | CELSIUS | 15 | MINUTE | 2-Amino-3-nitrophenol 1b1 (5 g; 32.4 mmol) was dissolved in H2O (29.5 mL) and 1,4-dioxane (14.7 mL). The mixture was heated to reflux and hydrobromic acid (48%; 16.7 mL; 147 mmol) was added dropwise over a period of 20 min. Upon completion of the addition, the reflux was maintained an additional 15 min. The reaction wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | O1CCOCC1.O | 0 | 0.25 | Br.Nc1c(O)cccc1[N+](=O)[O-]>O1CCOCC1.O>O=[N+]([O-])c1cccc(O)c1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e9c9feaad4304b79a1b09618d00f1190 | COc1cccc([N+](=O)[O-])c1Br>>COc1cccc(N)c1Br | BrC1=C(C=CC=C1[N+](=O)[O-])OC.C(=O)([O-])[O-].[Na+].[Na+]>>BrC1=C(N)C=CC=C1OC | O=[N+:8]([O-])[c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[c:9]1[Br:10]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH2:8])[c:9]1[Br:10] | COc1cccc([N+](=O)[O-])c1Br | COc1cccc(N)c1Br | null | [Fe] | O.C(C)(=O)O.C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | 2-Bromo-3-nitroanisole 1b3 (1.00 g; 4.31 mmol) was dissolved in glacial acetic acid (11.0 mL)/ethanol (11.0 mL) and to the solution was added iron powder (0.98 g; 17.5 mmol). The mixture was stirred at reflux for 3.5 hr and worked up. The reaction mixture was diluted with water (35 mL), neutralized with solid Na2CO3 an... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Fe].O.C(C)(=O)O.C(C)O | null | null | COc1cccc([N+](=O)[O-])c1Br>[Fe].O.C(C)(=O)O.C(C)O>COc1cccc(N)c1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-894bea510080468f9d16eb64479f5a58 | Cl.Nc1c(O)cccc1[N+](=O)[O-]>>O=[N+]([O-])c1cccc(O)c1Cl | Cl.N(=O)[O-].[Na+].NC1=C(C=CC=C1[N+](=O)[O-])O.Cl>>ClC1=C(C=CC=C1[N+](=O)[O-])O | [ClH:11].N[c:10]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][cH:6][cH:7][c:8]1[OH:9]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([OH:9])[c:10]1[Cl:11] | Cl.Nc1c(O)cccc1[N+](=O)[O-] | O=[N+]([O-])c1cccc(O)c1Cl | null | null | O1CCOCC1.O | Miscellaneous | OtherReaction | 976fb3f0996203ccf639edc3dd63ebf792dabe502fe07eb66206f5ee630d746b | 1129c10513c603d2647e51dd9713063aaf10bd8a364ed275b9b93c32624e3ba4 | c1ccccc1 | N-[c;H0;D3;+0:1](:[c:2](-[#7;+:3]):[c:4]):[c:5](-[O;D1;H1:6]):[c:7].[ClH;D0;+0:8]>>[#7;+:3]-[c:2](:[c:4]):[c;H0;D3;+0:1](-[Cl;H0;D1;+0:8]):[c:5](-[O;D1;H1:6]):[c:7] | null | [] | 70 | CELSIUS | 15 | MINUTE | 2-Amino-3-nitrophenol 1b1 (5 g; 32.4 mmol) was dissolved in concentrated HCl (75 mL) and 1,4-dioxane (14.7 mL). The mixture was heated to 70° C. until most of the solids were in solution. The reaction mixture was cooled to 0° C. (ice bath), and sodium nitrite (2.23 g; 32.3 mmol) in H2O (5.4 mL) was added over a period ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | O1CCOCC1.O | 70 | 0.25 | Cl.Nc1c(O)cccc1[N+](=O)[O-]>O1CCOCC1.O>O=[N+]([O-])c1cccc(O)c1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aee28bb42b424147965b597279f35827 | COc1cccc([N+](=O)[O-])c1Cl>>COc1cccc(N)c1Cl | ClC1=C(C=CC=C1[N+](=O)[O-])OC.C(=O)([O-])[O-].[Na+].[Na+]>>ClC1=C(N)C=CC=C1OC | O=[N+:8]([O-])[c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[c:9]1[Cl:10]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH2:8])[c:9]1[Cl:10] | COc1cccc([N+](=O)[O-])c1Cl | COc1cccc(N)c1Cl | null | [Fe] | O.C(C)(=O)O.C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 103.5 | [{"value": 100.0, "product": "ClC1=C(N)C=CC=C1OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 103.5, "product": "ClC1=C(N)C=CC=C1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Chloro-3-nitroanisole 1c2 (1.38 g; 7.36 mmol) was dissolved in a mixture of glacial acetic acid (19 mL)/ethanol (19 mL). To this solution was added iron powder (1.64 g; 29.4 mmol). The mixture was stirred at reflux for 3.5 hr and worked up. The reaction mixture was diluted with water (70 mL), neutralized with solid N... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Fe].O.C(C)(=O)O.C(C)O | null | null | COc1cccc([N+](=O)[O-])c1Cl>[Fe].O.C(C)(=O)O.C(C)O>COc1cccc(N)c1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cb8575a7b29d4316add54ada91f35189 | CCOC(C)=O.Nc1ccccc1.c1ccc(Oc2ccccc2)cc1>>COc1ccc2c(O)ccnc2c1C | C1(=CC=CC=C1)OC1=CC=CC=C1.NC1=CC=CC=C1.CCCCCC.CCOC(=O)C>>OC1=CC=NC2=C(C(=CC=C12)OC)C | [CH2:1]([O:2][C:3]([CH3:4])=[O:8])[CH3:14].[cH:5]1[cH:6][c:12]([NH2:11])[cH:13][cH:7][cH:9]1.c1ccc(Oc2cc[cH:10]cc2)cc1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([OH:8])[cH:9][cH:10][n:11][c:12]2[c:13]1[CH3:14] | CCOC(C)=O.Nc1ccccc1.c1ccc(Oc2ccccc2)cc1 | COc1ccc2c(O)ccnc2c1C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | cef090c5bd97e780cab2d3ed8ad5652b8c9f5cec6204eb129e076255d355df89 | dc0517de81a68d30734570298cb2d349ee8945c6caff5b6a241025d7c6c8628c | c1ccc2ncccc2c1 | O(-c1:c:c:[cH;D2;+0:1]:c:c:1)-c1:c:c:c:c:c:1.[CH3;D1;+0:2]-[CH2;D2;+0:3]-[#8:4]-[C;H0;D3;+0:5](-[CH3;D1;+0:6])=[O;H0;D1;+0:7].[NH2;D1;+0:8]-[c:9]1:[cH;D2;+0:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[cH;D2;+0:13]:[cH;D2;+0:14]:1>>[CH3;D1;+0:2]-[c;H0;D3;+0:10]1:[c:9]2:[n;H0;D2;+0:8]:[cH;D2;+0:1]:[cH;D2;+0:12]:[c;H0;D3;+0:11](-[OH... | null | [] | 300 | CELSIUS | 20 | MINUTE | A three-neck flask containing diphenyl ether (1.9 mL; 11.75 mmol) was placed into a preheated sand bath heated to ˜300° C. and the sand bath allowed to slowly heat further to ˜330° C. so as the internal temperature was between 245-250° C. The aniline derivative 1s1 was added portion-wise (immediately seeing gas evoluti... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Primary amine | Ether.Aromatic alcohol | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HO- | null | 300 | 0.333333 | CCOC(C)=O.Nc1ccccc1.c1ccc(Oc2ccccc2)cc1>>COc1ccc2c(O)ccnc2c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a1acb0651e9f4126819cd5ea323804fc | CC(C)[C@H](N)C(=O)O>>CC(C)C(N)C(=O)[O-] | N[C@@H](C(C)C)C(=O)O.[OH-].[Na+]>>NC(C(=O)[O-])C(C)C.[Na+] | [CH3:1][CH:2]([CH3:3])[C@H:4]([NH2:5])[C:6](=[O:7])[OH:8]>>[CH3:1][CH:2]([CH3:3])[CH:4]([NH2:5])[C:6](=[O:7])[O-:8] | CC(C)[C@H](N)C(=O)O | CC(C)C(N)C(=O)[O-] | null | null | O | Oxidation | Carboxylic acid to carboxylate | af9382a4a3fca177895c8a400271aa22025197fc08b983f9d71150044c1e6777 | b3097057beeca787f1d4960a7ee432572ee7aecad541233195b0dbbc0f674e9c | null | [C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4]>>[C:1]-[C:2](-[O-;H0;D1:4])=[O;D1;H0:3] | null | [] | null | null | null | null | Separately, in a single-necked, round bottomed flask, equipped with a magnetic stirrer, 5.86 g (50 mmol) of Valine is dissolved in 200 ml of water. To this is added 55 ml of 1M sodium hydroxide with vigorous stirring, until heat production ceases. At this point the water is removed by evaporation to yield the carboxyla... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | null | null | null | null | O | null | null | CC(C)[C@H](N)C(=O)O>O>CC(C)C(N)C(=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e1d22e3799a5420585632407023d90b9 | CC(C)C(N)C(=O)[O-].CCCC(=O)Cl>>CCCC(=O)OC(=O)C(N)C(C)C | C(CCC)(=O)Cl.NC(C(=O)[O-])C(C)C.[Na+].C(CCC)(=O)Cl>>C(CCC)(=O)OC(C(C(C)C)N)=O | [O-:6][C:7](=[O:8])[CH:9]([NH2:10])[CH:11]([CH3:12])[CH3:13].Cl[C:4]([CH2:3][CH2:2][CH3:1])=[O:5]>>[CH3:1][CH2:2][CH2:3][C:4](=[O:5])[O:6][C:7](=[O:8])[CH:9]([NH2:10])[CH:11]([CH3:12])[CH3:13] | CC(C)C(N)C(=O)[O-].CCCC(=O)Cl | CCCC(=O)OC(=O)C(N)C(C)C | null | null | null | Acylation | OtherReaction | a277333969c51673a7c4bc3b7a1d27397572756db5225daff581114d737437ec | 5fefc881dc234269fd51d1840a72dd88a62ba4ed6b7c2dfd03e5f64e328bf825 | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6](-[O-;H0;D1:7])=[O;D1;H0:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C:6](-[C:5])=[O;D1;H0:8] | null | [] | null | null | null | null | Finally, in a dry 2-necked, round bottomed flask, fixed with a separatory funnel, containing 6.39 g (60 mmol) of the prepared butyryl chloride, and side arm water condenser fixed with a dry receiving flask, is placed 9.18 g (66 mmol) of sodium 2-amino-3-methylbutanoate. The round bottomed flask is placed in an ice bath... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Anhydride | null | null | null | Other | null | null | null | CC(C)C(N)C(=O)[O-].CCCC(=O)Cl>>CCCC(=O)OC(=O)C(N)C(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7aa9ab214c114f08b80f4d34aebbfee4 | CC[C@H](C)[C@H](N)C(=O)O>>CCC(C)C(N)C(=O)[O-] | N[C@@H]([C@@H](C)CC)C(=O)O.[OH-].[Na+]>>NC(C(=O)[O-])C(CC)C.[Na+] | [CH3:1][CH2:2][C@H:3]([CH3:4])[C@H:5]([NH2:6])[C:7](=[O:8])[OH:9]>>[CH3:1][CH2:2][CH:3]([CH3:4])[CH:5]([NH2:6])[C:7](=[O:8])[O-:9] | CC[C@H](C)[C@H](N)C(=O)O | CCC(C)C(N)C(=O)[O-] | null | null | O | Oxidation | Carboxylic acid to carboxylate | af9382a4a3fca177895c8a400271aa22025197fc08b983f9d71150044c1e6777 | b3097057beeca787f1d4960a7ee432572ee7aecad541233195b0dbbc0f674e9c | null | [C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4]>>[C:1]-[C:2](-[O-;H0;D1:4])=[O;D1;H0:3] | null | [] | null | null | null | null | Separately, in a single-necked, round bottomed flask, equipped with a magnetic stirrer, 6.56 g (50 mmol) of Isoleucine is dissolved in 200 ml of water. To this is added 55 ml of 1M sodium hydroxide with vigorous stirring, until heat production ceases. At this point the water is removed by evaporation to yield the carbo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | null | null | null | null | O | null | null | CC[C@H](C)[C@H](N)C(=O)O>O>CCC(C)C(N)C(=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-06008332fead487594dfab2b7e8eb607 | CCC(C)C(N)C(=O)[O-].CCCCCC(=O)Br>>CCCCCC(=O)OC(=O)C(N)C(C)CC | C(CCCCC)(=O)Br.NC(C(=O)[O-])C(CC)C.[Na+].C(CCCCC)(=O)Br>>C(CCCCC)(=O)OC(C(C(CC)C)N)=O | [O-:8][C:9](=[O:10])[CH:11]([NH2:12])[CH:13]([CH3:14])[CH2:15][CH3:16].Br[C:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:7]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6](=[O:7])[O:8][C:9](=[O:10])[CH:11]([NH2:12])[CH:13]([CH3:14])[CH2:15][CH3:16] | CCC(C)C(N)C(=O)[O-].CCCCCC(=O)Br | CCCCCC(=O)OC(=O)C(N)C(C)CC | null | null | null | Acylation | OtherReaction | a277333969c51673a7c4bc3b7a1d27397572756db5225daff581114d737437ec | 5fefc881dc234269fd51d1840a72dd88a62ba4ed6b7c2dfd03e5f64e328bf825 | null | Br-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6](-[O-;H0;D1:7])=[O;D1;H0:8]>>[C:5]-[C:6](=[O;D1;H0:8])-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | null | [] | null | null | null | null | Finally, in a dry 2-necked, round bottomed flask, fixed with a separatory funnel, containing 10.81 g (60 mmol) of the prepared hexanoyl bromide, and side arm water condenser fixed with a dry receiving flask, is placed 11.03 g (72 mmol) of sodium 2-amino-3-methylpentanoate. The round bottomed flask is placed in an ice b... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Anhydride | null | null | null | Br- | null | null | null | CCC(C)C(N)C(=O)[O-].CCCCCC(=O)Br>>CCCCCC(=O)OC(=O)C(N)C(C)CC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e74882c81c994186b3a5b592a2f17355 | CCCCCCCCCCCC(=O)O.O=S(Cl)Cl>>CCCCCCCCCCCC(=O)Cl | S(=O)(Cl)Cl.S(=O)(Cl)Cl.S(=O)(Cl)Cl.C(CCCCCCCCCCC)(=O)O>>C(CCCCCCCCCCC)(=O)Cl | O[C:12]([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:13].O=S(Cl)[Cl:14]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[O:13])[Cl:14] | CCCCCCCCCCCC(=O)O.O=S(Cl)Cl | CCCCCCCCCCCC(=O)Cl | null | null | O | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | null | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3] | null | [] | 45 | CELSIUS | 50 | MINUTE | In a dry 2-necked, round bottomed flask, equipped with a magnetic stirrer and fixed with a separatory funnel, containing 5.85 ml (80 mmol) of thionyl chloride, and a water condenser, is placed 10.02 g (50 mmol) of dodecanoic acid. Addition of the thionyl chloride is completed with heating to about 45° C. over the cours... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | null | HCl | O | 45 | 0.833333 | CCCCCCCCCCCC(=O)O.O=S(Cl)Cl>O>CCCCCCCCCCCC(=O)Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-deb832ac8bfe4632baf579b126449788 | N=C(N)NCCC[C@H](N)C(=O)O>>N=C(N)NCCCC(N)C(=O)[O-] | N[C@@H](CCCNC(N)=N)C(=O)O.[OH-].[NH4+]>>NC(C(=O)[O-])CCCNC(=N)N.[NH4+] | [NH:1]=[C:2]([NH2:3])[NH:4][CH2:5][CH2:6][CH2:7][C@H:8]([NH2:9])[C:10](=[O:11])[OH:12]>>[NH:1]=[C:2]([NH2:3])[NH:4][CH2:5][CH2:6][CH2:7][CH:8]([NH2:9])[C:10](=[O:11])[O-:12] | N=C(N)NCCC[C@H](N)C(=O)O | N=C(N)NCCCC(N)C(=O)[O-] | null | null | O | Oxidation | Carboxylic acid to carboxylate | af9382a4a3fca177895c8a400271aa22025197fc08b983f9d71150044c1e6777 | b3097057beeca787f1d4960a7ee432572ee7aecad541233195b0dbbc0f674e9c | null | [C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4]>>[C:1]-[C:2](-[O-;H0;D1:4])=[O;D1;H0:3] | null | [] | null | null | null | null | Separately, in a single-necked, round bottomed flask, equipped with a magnetic stirrer, 10.45 g (60 mmol) of Arginine is dissolved in 300 ml of water. To this is added 78 ml of 1M ammonium hydroxide with vigorous stirring, until heat production ceases. At this point the water is removed by evaporation to yield the carb... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | null | null | null | null | O | null | null | N=C(N)NCCC[C@H](N)C(=O)O>O>N=C(N)NCCCC(N)C(=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5aeff84d06644da698fd1cedbb4780e1 | CCCCCCCCCCCC(=O)Cl.N=C(N)NCCCC(N)C(=O)[O-]>>CCCCCCCCCCCC(=O)OC(=O)C(N)CCCNC(=N)N | C(CCCCCCCCCCC)(=O)Cl.NC(C(=O)[O-])CCCNC(=N)N.[NH4+].C(CCCCCCCCCCC)(=O)Cl>>C(CCCCCCCCCCC)(=O)OC(C(CCCNC(=N)N)N)=O | Cl[C:12]([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:13].[O-:14][C:15](=[O:16])[CH:17]([NH2:18])[CH2:19][CH2:20][CH2:21][NH:22][C:23](=[NH:24])[NH2:25]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[O:13])[O:14][C:15](=[O:16])[CH:17]([NH2... | CCCCCCCCCCCC(=O)Cl.N=C(N)NCCCC(N)C(=O)[O-] | CCCCCCCCCCCC(=O)OC(=O)C(N)CCCNC(=N)N | null | null | null | Protection | OtherReaction | 28c2e4e4e899b53f47f26c928dd1e31ebef90e8fc1b5afe08cb871bc47f95bd3 | d9986b0eedf845fc44f27353fb210fb36c2b2eb27a1b7c079579aaba5d804c30 | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6](-[O-;H0;D1:7])=[O;D1;H0:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C:6](-[C:5])=[O;D1;H0:8] | null | [] | null | null | null | null | Finally, in a dry 2-necked, round bottomed flask, fixed with a separatory funnel, containing 15.31 g (70 mmol) of the prepared dodecanoyl chloride, and side arm water condenser fixed with a dry receiving flask, is placed 16.06 g (84 mmol) of ammonium 2-amino-5-guanidinopentanoate. The round bottomed flask is placed in ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Anhydride | null | null | null | Other | null | null | null | CCCCCCCCCCCC(=O)Cl.N=C(N)NCCCC(N)C(=O)[O-]>>CCCCCCCCCCCC(=O)OC(=O)C(N)CCCNC(=N)N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5d9ed55cfb244fc980f4735fb78cfebb | CCCCCCCCCCCCCCCCCC(=O)O.O=S(Cl)Cl>>CCCCCCCCCCCCCCCCCC(=O)Cl | S(=O)(Cl)Cl.S(=O)(Cl)Cl.S(=O)(Cl)Cl.C(CCCCCCCCCCCCCCCCC)(=O)O>>C(CCCCCCCCCCCCCCCCC)(=O)Cl | O[C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:19].O=S(Cl)[Cl:20]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[Cl:20] | CCCCCCCCCCCCCCCCCC(=O)O.O=S(Cl)Cl | CCCCCCCCCCCCCCCCCC(=O)Cl | null | null | O | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | null | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3] | null | [] | 45 | CELSIUS | 45 | MINUTE | In a dry 2-necked, round bottomed flask, equipped with a magnetic stirrer and fixed with a separatory funnel, containing 4.81 ml (66 mmol) of thionyl chloride, and a water condenser, is placed 15.65 g (55 mmol) of stearic acid. Addition of the thionyl chloride is completed with heating to about 45° C. over the course o... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | null | HCl | O | 45 | 0.75 | CCCCCCCCCCCCCCCCCC(=O)O.O=S(Cl)Cl>O>CCCCCCCCCCCCCCCCCC(=O)Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-345d0a27018043d1a770069557aa1330 | CC(C)C[C@H](N)C(=O)O>>CC(C)CC(N)C(=O)[O-] | N[C@@H](CC(C)C)C(=O)O.[OH-].[K+]>>NC(C(=O)[O-])CC(C)C.[K+] | [CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([NH2:6])[C:7](=[O:8])[OH:9]>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH:5]([NH2:6])[C:7](=[O:8])[O-:9] | CC(C)C[C@H](N)C(=O)O | CC(C)CC(N)C(=O)[O-] | null | null | O | Oxidation | Carboxylic acid to carboxylate | af9382a4a3fca177895c8a400271aa22025197fc08b983f9d71150044c1e6777 | b3097057beeca787f1d4960a7ee432572ee7aecad541233195b0dbbc0f674e9c | null | [C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4]>>[C:1]-[C:2](-[O-;H0;D1:4])=[O;D1;H0:3] | null | [] | null | null | null | null | Separately, in a single-necked, round bottomed flask, equipped with a magnetic stirrer, 7.87 g (60 mmol) of Leucine is dissolved in 300 ml of water. To this is added 72 ml of 1 M potassium hydroxide with vigorous stirring, until heat production ceases. At this point the water is removed by evaporation to yield the carb... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | null | null | null | null | O | null | null | CC(C)C[C@H](N)C(=O)O>O>CC(C)CC(N)C(=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-79d913cc7ac74a02967425c33d1b82fd | CC(C)CC(N)C(=O)[O-].CCCCCCCCCCCCCCCCCC(=O)Cl>>CCCCCCCCCCCCCCCCCC(=O)OC(=O)C(N)CC(C)C | C(CCCCCCCCCCCCCCCCC)(=O)Cl.NC(C(=O)[O-])CC(C)C.[K+].C(CCCCCCCCCCCCCCCCC)(=O)Cl>>C(CCCCCCCCCCCCCCCCC)(=O)OC(C(CC(C)C)N)=O | [O-:20][C:21](=[O:22])[CH:23]([NH2:24])[CH2:25][CH:26]([CH3:27])[CH3:28].Cl[C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:19]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:1... | CC(C)CC(N)C(=O)[O-].CCCCCCCCCCCCCCCCCC(=O)Cl | CCCCCCCCCCCCCCCCCC(=O)OC(=O)C(N)CC(C)C | null | null | null | Acylation | OtherReaction | a277333969c51673a7c4bc3b7a1d27397572756db5225daff581114d737437ec | 5fefc881dc234269fd51d1840a72dd88a62ba4ed6b7c2dfd03e5f64e328bf825 | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6](-[O-;H0;D1:7])=[O;D1;H0:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C:6](-[C:5])=[O;D1;H0:8] | null | [] | null | null | null | null | Finally, in a dry 2-necked, round bottomed flask, fixed with a separatory funnel, containing 21.27 g (70 mmol) of the prepared stearoyl chloride, and side arm water condenser fixed with a dry receiving flask, is placed 13.03 g (77 mmol) of potassium 2-amino-4-methylpentanoate. The round bottomed flask is placed in an i... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Anhydride | null | null | null | Other | null | null | null | CC(C)CC(N)C(=O)[O-].CCCCCCCCCCCCCCCCCC(=O)Cl>>CCCCCCCCCCCCCCCCCC(=O)OC(=O)C(N)CC(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-80af1d69e9954dfa913604ecbf08a2fe | CCCCC/C=C\C/C=C\CCCCCCCC(=O)O.O=S(Cl)Cl>>CCCCC/C=C\C/C=C\CCCCCCCC(=O)Cl | S(=O)(Cl)Cl.S(=O)(Cl)Cl.S(=O)(Cl)Cl.C(CCCCCCC\C=C/C\C=C/CCCCC)(=O)O>>C(CCCCCCC\C=C/C\C=C/CCCCC)(=O)Cl | O[C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]/[CH:10]=[CH:9]\[CH2:8]/[CH:7]=[CH:6]\[CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:19].O=S(Cl)[Cl:20]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[Cl:20] | CCCCC/C=C\C/C=C\CCCCCCCC(=O)O.O=S(Cl)Cl | CCCCC/C=C\C/C=C\CCCCCCCC(=O)Cl | null | null | O | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | null | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3] | null | [] | 40 | CELSIUS | 50 | MINUTE | In a dry 2-necked, round bottomed flask, equipped with a magnetic stirrer and fixed with a separatory funnel, containing 9.35 ml (128 mmol) of thionyl chloride, and a water condenser, is placed 24.90 ml (80 mmol) of linoleic acid. Addition of the thionyl chloride is completed with heating to about 40° C. over the cours... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | null | HCl | O | 40 | 0.833333 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)O.O=S(Cl)Cl>O>CCCCC/C=C\C/C=C\CCCCCCCC(=O)Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a4c3049184d5482a8a34391cdcb4880c | CC(N)C(=O)[O-].CCCCC/C=C\C/C=C\CCCCCCCC(=O)Cl.CCCCC/C=C\C/C=C\CCCCCCCC(=O)Cl>>CCCCC/C=C\C/C=C\CCCCCC(=O)OC(=O)CCCCC/C=C\C/C=C\CCCCC | C(CCCCCCC\C=C/C\C=C/CCCCC)(=O)Cl.NC(C(=O)[O-])C.[NH4+].C(CCCCCCC\C=C/C\C=C/CCCCC)(=O)Cl>>C(CCCCC\C=C/C\C=C/CCCCC)(=O)OC(CCCCC\C=C/C\C=C/CCCCC)=O | CC(N)C(=O)[O-:18].Cl[C:19](=[O:20])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]CC/[CH:10]=[CH:9]\[CH2:8]/[CH:7]=[CH:6]\[CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].Cl[C:16]([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]C[CH2:31]/[CH:30]=[CH:29]\[CH2:28]/[CH:27]=[CH:26]\C[CH2:32][CH2:33][CH2:34][CH3:35])=[O:17]>>[CH3:1][CH2:2][CH2:3][CH2:... | CC(N)C(=O)[O-].CCCCC/C=C\C/C=C\CCCCCCCC(=O)Cl.CCCCC/C=C\C/C=C\CCCCCCCC(=O)Cl | CCCCC/C=C\C/C=C\CCCCCC(=O)OC(=O)CCCCC/C=C\C/C=C\CCCCC | null | null | null | Acylation | OtherReaction | 76480b7bb72821d3e774726a37d831593401301f426e09495a7f10deb9c3aded | f6372bc3afaa901ffa5cb4a5801eb88e4a808f6822f7883e1c1262c45daa5921 | null | C-C(-N)-C(=O)-[O-;H0;D1:1].Cl-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]-[C:5]-[C:6]-[C:7]-[CH2;D2;+0:8]-C-C/[CH;D2;+0:9]=[C:10]\[C:11]/[C:12]=[C:13]\[C:14].Cl-[C;H0;D3;+0:15](=[O;D1;H0:16])-[C:17]-[C:18]-[C:19]-[C:20]-[CH2;D2;+0:21]-C-[CH2;D2;+0:22]/[C:23]=[C:24]\[C:25]/[C:26]=[CH;D2;+0:27]\C-[CH2;D2;+0:28]-[C:29]-[C:30]>>[C:... | null | [] | null | null | null | null | Finally, in a dry 2-necked, round bottomed flask, fixed with a separatory funnel, containing 17.93 g (60 mmol) of the prepared (9Z,12Z)-octadeca-9,12-dienoyl chloride, and side arm water condenser fixed with a dry receiving flask, is placed 7.64 g (72 mmol) of ammonium 2-aminopropanoate. The round bottomed flask is pla... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary amine | Anhydride | null | null | null | HCl | null | null | null | CC(N)C(=O)[O-].CCCCC/C=C\C/C=C\CCCCCCCC(=O)Cl.CCCCC/C=C\C/C=C\CCCCCCCC(=O)Cl>>CCCCC/C=C\C/C=C\CCCCCC(=O)OC(=O)CCCCC/C=C\C/C=C\CCCCC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-58ce9951f10842119d4e46869554f4a8 | CN(CC(=O)O)C(=N)N>>CN(CC(=O)[O-])C(=N)N | O=C(O)CN(C)C(N)=N.[OH-].[Na+]>>CN(C(=N)N)CC(=O)[O-].[Na+] | [CH3:1][N:2]([CH2:3][C:4](=[O:5])[OH:6])[C:7](=[NH:8])[NH2:9]>>[CH3:1][N:2]([CH2:3][C:4](=[O:5])[O-:6])[C:7](=[NH:8])[NH2:9] | CN(CC(=O)O)C(=N)N | CN(CC(=O)[O-])C(=N)N | null | null | O | Oxidation | Carboxylic acid to carboxylate | af9382a4a3fca177895c8a400271aa22025197fc08b983f9d71150044c1e6777 | b3097057beeca787f1d4960a7ee432572ee7aecad541233195b0dbbc0f674e9c | null | [C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4]>>[C:1]-[C:2](-[O-;H0;D1:4])=[O;D1;H0:3] | null | [] | null | null | null | null | Separately, in a single-necked, round bottomed flask, equipped with a magnetic stirrer, 6.56 g (50 mmol) of creatine is dissolved in 500 ml of water. To this is added 55 ml of 1M sodium hydroxide with vigorous stirring, until heat production ceases. At this point the water is removed by evaporation to yield the carboxy... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | null | null | null | null | O | null | null | CN(CC(=O)O)C(=N)N>O>CN(CC(=O)[O-])C(=N)N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f05d0779617340459ecd21e2d8bbbfea | CCCC(=O)Cl.CN(CC(=O)[O-])C(=N)N>>CN(CC(=O)OC(=O)CN(C)C(=N)N)C(=N)N | C(CCC)(=O)Cl.CN(C(=N)N)CC(=O)[O-].[Na+].C(CCC)(=O)Cl>>CN(C(=N)N)CC(=O)OC(CN(C(=N)N)C)=O | Cl[C:4]([CH2:3]C[CH3:1])=[O:5].[NH:2]=[C:12]([N:10]([CH2:9][C:7]([O-:6])=[O:8])[CH3:11])[NH2:17]>>[CH3:1][N:2]([CH2:3][C:4](=[O:5])[O:6][C:7](=[O:8])[CH2:9][N:10]([CH3:11])[C:12](=[NH:13])[NH2:14])[C:15](=[NH:16])[NH2:17] | CCCC(=O)Cl.CN(CC(=O)[O-])C(=N)N | CN(CC(=O)OC(=O)CN(C)C(=N)N)C(=N)N | null | null | null | Protection | OtherReaction | 4e8a377bb3b8a9ec9f325a7ae963a97901b55ab63a5f830c6388ca9a6aea2c28 | 5b33930ec8bab92a3e3bea9235df5aba8b45e7c85a07488cc536714dab18306d | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-C-[CH3;D1;+0:4].[C;D1;H3:5]-[#7:6](-[C:7]-[C:8](-[O-;H0;D1:9])=[O;D1;H0:10])-[C;H0;D3;+0:11](-[NH2;D1;+0:12])=[NH;D1;+0:13]>>[C;D1;H3:5]-[#7:6](-[C:7]-[C:8](=[O;D1;H0:10])-[O;H0;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[N;H0;D3;+0:13](-[CH3;D1;+0:4])-[C:14](=[N;D... | null | [] | null | null | null | null | Finally, in a dry 2-necked, round bottomed flask, fixed with a separatory funnel, containing 6.39 g (60 mmol) of the prepared butyryl chloride, and side arm water condenser fixed with a dry receiving flask, is placed 12.08 g (66 mmol) of sodium 2-(1-methylguanidino)acetate. The round bottomed flask is placed in an ice ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Anhydride.Primary amine.Primary amine.Tertiary amine | null | null | null | null | null | null | null | CCCC(=O)Cl.CN(CC(=O)[O-])C(=N)N>>CN(CC(=O)OC(=O)CN(C)C(=N)N)C(=N)N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3419abdcfbd8463c93153c2bc3328298 | CN(CC(=O)O)C(=N)N>>CN(CC(=O)[O-])C(=N)N | O=C(O)CN(C)C(N)=N.[OH-].[Na+]>>CN(C(=N)N)CC(=O)[O-].[Na+] | [CH3:1][N:2]([CH2:3][C:4](=[O:5])[OH:6])[C:7](=[NH:8])[NH2:9]>>[CH3:1][N:2]([CH2:3][C:4](=[O:5])[O-:6])[C:7](=[NH:8])[NH2:9] | CN(CC(=O)O)C(=N)N | CN(CC(=O)[O-])C(=N)N | null | null | O | Oxidation | Carboxylic acid to carboxylate | af9382a4a3fca177895c8a400271aa22025197fc08b983f9d71150044c1e6777 | b3097057beeca787f1d4960a7ee432572ee7aecad541233195b0dbbc0f674e9c | null | [C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4]>>[C:1]-[C:2](-[O-;H0;D1:4])=[O;D1;H0:3] | null | [] | null | null | null | null | Separately, in a single-necked, round bottomed flask, equipped with a magnetic stirrer, 6.56 g (50 mmol) of creatine is dissolved in 500 ml of water. To this is added 55 ml of 1M sodium hydroxide with vigorous stirring, until heat production ceases. At this point the water is removed by evaporation to yield the carboxy... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | null | null | null | null | O | null | null | CN(CC(=O)O)C(=N)N>O>CN(CC(=O)[O-])C(=N)N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8e672e2d6a704bb4adf23380a4afb362 | CCCCCC(=O)Br.CN(CC(=O)[O-])C(=N)N>>CN(CC(=O)OC(=O)CN(C)C(=N)N)C(=N)N | C(CCCCC)(=O)Br.CN(C(=N)N)CC(=O)[O-].[Na+].C(CCCCC)(=O)Br>>CN(C(=N)N)CC(=O)OC(CN(C(=N)N)C)=O | Br[C:4]([CH2:3]CCC[CH3:1])=[O:5].[NH2:2][C:12]([N:10]([CH2:9][C:7]([O-:6])=[O:8])[CH3:11])=[NH:13]>>[CH3:1][N:2]([CH2:3][C:4](=[O:5])[O:6][C:7](=[O:8])[CH2:9][N:10]([CH3:11])[C:12](=[NH:13])[NH2:14])[C:15](=[NH:16])[NH2:17] | CCCCCC(=O)Br.CN(CC(=O)[O-])C(=N)N | CN(CC(=O)OC(=O)CN(C)C(=N)N)C(=N)N | null | null | null | Protection | OtherReaction | 4e8a377bb3b8a9ec9f325a7ae963a97901b55ab63a5f830c6388ca9a6aea2c28 | 5b33930ec8bab92a3e3bea9235df5aba8b45e7c85a07488cc536714dab18306d | null | Br-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-C-C-C-[CH3;D1;+0:4].[C;D1;H3:5]-[#7:6](-[C:7]-[C:8](-[O-;H0;D1:9])=[O;D1;H0:10])-[C;H0;D3;+0:11](=[N;D1;H1:12])-[NH2;D1;+0:13]>>[C;D1;H3:5]-[#7:6](-[C:7]-[C:8](=[O;D1;H0:10])-[O;H0;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[N;H0;D3;+0:13](-[CH3;D1;+0:4])-[C:14](=[... | null | [] | null | null | null | null | Finally, in a dry 2-necked, round bottomed flask, fixed with a separatory funnel, containing 10.81 g (60 mmol) of the prepared hexanoyl bromide, and side arm water condenser fixed with a dry receiving flask, is placed 13.18 g (72 mmol) of sodium 2-(1-methylguanidino)acetate. The round bottomed flask is placed in an ice... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Anhydride.Primary amine.Primary amine.Tertiary amine | null | null | null | null | null | null | null | CCCCCC(=O)Br.CN(CC(=O)[O-])C(=N)N>>CN(CC(=O)OC(=O)CN(C)C(=N)N)C(=N)N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5c0a49985fdd4dd08228186d3b1aba59 | CCCCCCCCCCCC(=O)O.O=S(Cl)Cl>>CCCCCCCCCCCC(=O)Cl | S(=O)(Cl)Cl.S(=O)(Cl)Cl.S(=O)(Cl)Cl.C(CCCCCCCCCCC)(=O)O>>C(CCCCCCCCCCC)(=O)Cl | O[C:12]([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:13].O=S(Cl)[Cl:14]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[O:13])[Cl:14] | CCCCCCCCCCCC(=O)O.O=S(Cl)Cl | CCCCCCCCCCCC(=O)Cl | null | null | O | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | null | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3] | null | [] | 45 | CELSIUS | 50 | MINUTE | In a dry 2-necked, round bottomed flask, equipped with a magnetic stirrer and fixed with a separatory funnel, containing 5.85 ml (80 mmol) of thionyl chloride, and a water condenser, is placed 10.02 g (50 mmol) of dodecanoic acid. Addition of the thionyl chloride is completed with heating to about 45° C. over the cours... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | null | HCl | O | 45 | 0.833333 | CCCCCCCCCCCC(=O)O.O=S(Cl)Cl>O>CCCCCCCCCCCC(=O)Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6035ace7e84841c395d5c4d142ad3c75 | CN(CC(=O)O)C(=N)N>>CN(CC(=O)[O-])C(=N)N | O=C(O)CN(C)C(N)=N.[OH-].[NH4+]>>CN(C(=N)N)CC(=O)[O-].[NH4+] | [CH3:1][N:2]([CH2:3][C:4](=[O:5])[OH:6])[C:7](=[NH:8])[NH2:9]>>[CH3:1][N:2]([CH2:3][C:4](=[O:5])[O-:6])[C:7](=[NH:8])[NH2:9] | CN(CC(=O)O)C(=N)N | CN(CC(=O)[O-])C(=N)N | null | null | O | Oxidation | Carboxylic acid to carboxylate | af9382a4a3fca177895c8a400271aa22025197fc08b983f9d71150044c1e6777 | b3097057beeca787f1d4960a7ee432572ee7aecad541233195b0dbbc0f674e9c | null | [C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4]>>[C:1]-[C:2](-[O-;H0;D1:4])=[O;D1;H0:3] | null | [] | null | null | null | null | Separately, in a single-necked, round bottomed flask, equipped with a magnetic stirrer, 7.87 g (60 mmol) of creatine is dissolved in 600 ml of water. To this is added 78 ml of 1M ammonium hydroxide with vigorous stirring, until heat production ceases. At this point the water is removed by evaporation to yield the carbo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | null | null | null | null | O | null | null | CN(CC(=O)O)C(=N)N>O>CN(CC(=O)[O-])C(=N)N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e51685ad3b0e4bb78719ec30d7f5f84a | CCCCCCCCCCCCCCCCCC(=O)O.O=S(Cl)Cl>>CCCCCCCCCCCCCCCCCC(=O)Cl | S(=O)(Cl)Cl.S(=O)(Cl)Cl.S(=O)(Cl)Cl.C(CCCCCCCCCCCCCCCCC)(=O)O>>C(CCCCCCCCCCCCCCCCC)(=O)Cl | O[C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:19].O=S(Cl)[Cl:20]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[Cl:20] | CCCCCCCCCCCCCCCCCC(=O)O.O=S(Cl)Cl | CCCCCCCCCCCCCCCCCC(=O)Cl | null | null | O | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | null | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3] | null | [] | 45 | CELSIUS | 45 | MINUTE | In a dry 2-necked, round bottomed flask, equipped with a magnetic stirrer and fixed with a separatory funnel, containing 4.81 ml (66 mmol) of thionyl chloride, and a water condenser, is placed 15.65 g (55 mmol) of stearic acid. Addition of the thionyl chloride is completed with heating to about 45° C. over the course o... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | null | HCl | O | 45 | 0.75 | CCCCCCCCCCCCCCCCCC(=O)O.O=S(Cl)Cl>O>CCCCCCCCCCCCCCCCCC(=O)Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ac017f4279f9458d9339f09d79516c97 | CN(CC(=O)O)C(=N)N>>CN(CC(=O)[O-])C(=N)N | O=C(O)CN(C)C(N)=N.[OH-].[K+]>>CN(C(=N)N)CC(=O)[O-].[K+] | [CH3:1][N:2]([CH2:3][C:4](=[O:5])[OH:6])[C:7](=[NH:8])[NH2:9]>>[CH3:1][N:2]([CH2:3][C:4](=[O:5])[O-:6])[C:7](=[NH:8])[NH2:9] | CN(CC(=O)O)C(=N)N | CN(CC(=O)[O-])C(=N)N | null | null | O | Oxidation | Carboxylic acid to carboxylate | af9382a4a3fca177895c8a400271aa22025197fc08b983f9d71150044c1e6777 | b3097057beeca787f1d4960a7ee432572ee7aecad541233195b0dbbc0f674e9c | null | [C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4]>>[C:1]-[C:2](-[O-;H0;D1:4])=[O;D1;H0:3] | null | [] | null | null | null | null | Separately, in a single-necked, round bottomed flask, equipped with a magnetic stirrer, 7.87 g (60 mmol) of creatine is dissolved in 600 ml of water. To this is added 72 ml of 1M potassium hydroxide with vigorous stirring, until heat production ceases. At this point the water is removed by evaporation to yield the carb... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | null | null | null | null | O | null | null | CN(CC(=O)O)C(=N)N>O>CN(CC(=O)[O-])C(=N)N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1980a97a10944bc7b3ebae6466e12b97 | CCCCCCCCCCCCCCCCCC(=O)Cl.CN(CC(=O)[O-])C(=N)N>>CCCCCCCCCCCCCCCCCC(=O)OC(=O)CN(C)C(=N)N | C(CCCCCCCCCCCCCCCCC)(=O)Cl.CN(C(=N)N)CC(=O)[O-].[K+].C(CCCCCCCCCCCCCCCCC)(=O)Cl>>C(CCCCCCCCCCCCCCCCC)(=O)OC(CN(C(=N)N)C)=O | Cl[C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:19].[O-:20][C:21](=[O:22])[CH2:23][N:24]([CH3:25])[C:26](=[NH:27])[NH2:28]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]... | CCCCCCCCCCCCCCCCCC(=O)Cl.CN(CC(=O)[O-])C(=N)N | CCCCCCCCCCCCCCCCCC(=O)OC(=O)CN(C)C(=N)N | null | null | null | Protection | OtherReaction | 28c2e4e4e899b53f47f26c928dd1e31ebef90e8fc1b5afe08cb871bc47f95bd3 | d9986b0eedf845fc44f27353fb210fb36c2b2eb27a1b7c079579aaba5d804c30 | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6](-[O-;H0;D1:7])=[O;D1;H0:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[C:6](-[C:5])=[O;D1;H0:8] | null | [] | null | null | null | null | Finally, in a dry 2-necked, round bottomed flask, fixed with a separatory funnel, containing 21.27 g (70 mmol) of the prepared stearoyl chloride, and side arm water condenser fixed with a dry receiving flask, is placed 23.40 g (77 mmol) of potassium 2-(1-methylguanidino)acetate. The round bottomed flask is placed in an... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Anhydride | null | null | null | Other | null | null | null | CCCCCCCCCCCCCCCCCC(=O)Cl.CN(CC(=O)[O-])C(=N)N>>CCCCCCCCCCCCCCCCCC(=O)OC(=O)CN(C)C(=N)N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0bcb3d1cf9254d19a95a3cdda43b531b | CCCCC/C=C\C/C=C\CCCCCCCC(=O)O.O=S(Cl)Cl>>CCCCC/C=C\C/C=C\CCCCCCCC(=O)Cl | S(=O)(Cl)Cl.S(=O)(Cl)Cl.S(=O)(Cl)Cl.C(CCCCCCC\C=C/C\C=C/CCCCC)(=O)O>>C(CCCCCCC\C=C/C\C=C/CCCCC)(=O)Cl | O[C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]/[CH:10]=[CH:9]\[CH2:8]/[CH:7]=[CH:6]\[CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:19].O=S(Cl)[Cl:20]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[Cl:20] | CCCCC/C=C\C/C=C\CCCCCCCC(=O)O.O=S(Cl)Cl | CCCCC/C=C\C/C=C\CCCCCCCC(=O)Cl | null | null | O | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | null | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3] | null | [] | 40 | CELSIUS | 50 | MINUTE | In a dry 2-necked, round bottomed flask, equipped with a magnetic stirrer and fixed with a separatory funnel, containing 9.35 ml (128 mmol) of thionyl chloride, and a water condenser, is placed 24.90 ml (80 mmol) of linoleic acid. Addition of the thionyl chloride is completed with heating to about 40° C. over the cours... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | null | HCl | O | 40 | 0.833333 | CCCCC/C=C\C/C=C\CCCCCCCC(=O)O.O=S(Cl)Cl>O>CCCCC/C=C\C/C=C\CCCCCCCC(=O)Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-738c7e9edb764a9ab8ad87a2e28f310a | CN(CC(=O)O)C(=N)N>>CN(CC(=O)[O-])C(=N)N | O=C(O)CN(C)C(N)=N.[OH-].[NH4+]>>CN(C(=N)N)CC(=O)[O-].[NH4+] | [CH3:1][N:2]([CH2:3][C:4](=[O:5])[OH:6])[C:7](=[NH:8])[NH2:9]>>[CH3:1][N:2]([CH2:3][C:4](=[O:5])[O-:6])[C:7](=[NH:8])[NH2:9] | CN(CC(=O)O)C(=N)N | CN(CC(=O)[O-])C(=N)N | null | null | O | Oxidation | Carboxylic acid to carboxylate | af9382a4a3fca177895c8a400271aa22025197fc08b983f9d71150044c1e6777 | b3097057beeca787f1d4960a7ee432572ee7aecad541233195b0dbbc0f674e9c | null | [C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4]>>[C:1]-[C:2](-[O-;H0;D1:4])=[O;D1;H0:3] | null | [] | null | null | null | null | Separately, in a single-necked, round bottomed flask, equipped with a magnetic stirrer, 7.87 g (60 mmol) of creatine is dissolved in 600 ml of water. To this is added 78 ml of 1M ammonium hydroxide with vigorous stirring, until heat production ceases. At this point the water is removed by evaporation to yield the carbo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | null | null | null | null | null | O | null | null | CN(CC(=O)O)C(=N)N>O>CN(CC(=O)[O-])C(=N)N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ec3c00d00aa44b628bdbec3d60bafcbe | CCCCCCCC(=O)O.O=S(Br)Br>>CCCCCCCC(=O)Br | S(=O)(Br)Br.S(=O)(Br)Br.S(=O)(Br)Br.C(CCCCCCC)(=O)O>>C(CCCCCCC)(=O)Br | O[C:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:9].O=S(Br)[Br:10]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:9])[Br:10] | CCCCCCCC(=O)O.O=S(Br)Br | CCCCCCCC(=O)Br | null | null | O | Functional Group Interconversion | OtherReaction | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | null | Br-S(=O)-[Br;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]-[C:5]>>[Br;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]-[C:5] | null | [] | 50 | CELSIUS | null | null | In a dry 2-necked, round bottomed flask, equipped with a magnetic stirrer and fixed with a separatory funnel, containing 10.07 ml (130 mmol) of thionyl bromide, and a water condenser, is placed 10.30 ml (65 mmol) of octanoic acid. Addition of the thionyl bromide is completed with heating to about 50° C. over the course... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | null | HBr | O | 50 | null | CCCCCCCC(=O)O.O=S(Br)Br>O>CCCCCCCC(=O)Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-81defff891a547b3a96824b36a52363b | CCCCCCCC(=O)Br.CN(CC(=O)O)C(=N)N>>CCCCCCCC(=O)NC(=N)N(C)CC(=O)O | C(CCCCCCC)(=O)Br.N1=CC=CC=C1.C(CCCCCCC)(=O)Br.O=C(O)CN(C)C(N)=N.C(CCCCCCC)(=O)Br.C(=O)=O.C(CCCCCCC)(=O)Br>>CN(C(=N)NC(CCCCCCC)=O)CC(=O)O | Br[C:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:9].[NH2:10][C:11](=[NH:12])[N:13]([CH3:14])[CH2:15][C:16](=[O:17])[OH:18]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:9])[NH:10][C:11](=[NH:12])[N:13]([CH3:14])[CH2:15][C:16](=[O:17])[OH:18] | CCCCCCCC(=O)Br.CN(CC(=O)O)C(=N)N | CCCCCCCC(=O)NC(=N)N(C)CC(=O)O | null | null | ClCCl.CC(=O)C | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | null | Br-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[#7:5]-[C:6](=[N;D1;H1:7])-[NH2;D1;+0:8]>>[#7:5]-[C:6](=[N;D1;H1:7])-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | null | [] | null | null | null | null | In a dry 3-necked, round bottomed flask, equipped with a magnetic stirrer, a thermometer, a nitrogen inlet tube and the dropping funnel containing the octanoyl bromide solution, 7.08 g (54 mmol) of creatine is suspended, with stirring, in 50 ml of dry dichloromethane. To this suspension a catalytic amount (0.1 mmol) of... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | null | HBr | ClCCl.CC(=O)C | null | null | CCCCCCCC(=O)Br.CN(CC(=O)O)C(=N)N>ClCCl.CC(=O)C>CCCCCCCC(=O)NC(=N)N(C)CC(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-19ddd728dc474a718f53529edd1d687b | CCCCCCCCCCCC(=O)O.O=S(Cl)Cl>>CCCCCCCCCCCC(=O)Cl | S(=O)(Cl)Cl.S(=O)(Cl)Cl.S(=O)(Cl)Cl.C(CCCCCCCCCCC)(=O)O>>C(CCCCCCCCCCC)(=O)Cl | O[C:12]([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:13].O=S(Cl)[Cl:14]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[O:13])[Cl:14] | CCCCCCCCCCCC(=O)O.O=S(Cl)Cl | CCCCCCCCCCCC(=O)Cl | null | null | O | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | null | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3] | null | [] | 45 | CELSIUS | 45 | MINUTE | In a dry 2-necked, round bottomed flask, equipped with a magnetic stirrer and fixed with a separatory funnel, containing 13.13 ml (180 mmol) of thionyl chloride, and a water condenser, is placed 20.03 g (100 mmol) of dodecanoic acid. Addition of the thionyl chloride is completed with heating to about 45° C. over the co... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | null | HCl | O | 45 | 0.75 | CCCCCCCCCCCC(=O)O.O=S(Cl)Cl>O>CCCCCCCCCCCC(=O)Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f97a24765fae4e6bb2fa83918acd3402 | CCCCCCCCCCCC(=O)Cl.CN(CC(=O)O)C(=N)N>>CCCCCCCCCCCC(=O)NC(=N)N(C)CC(=O)O | C(CCCCCCCCCCC)(=O)Cl.N1=CC=CC=C1.C(CCCCCCCCCCC)(=O)Cl.O=C(O)CN(C)C(N)=N.C(CCCCCCCCCCC)(=O)Cl.C(=O)=O.C(CCCCCCCCCCC)(=O)Cl>>C(CCCCCCCCCCC)(=O)NC(N(C)CC(=O)O)=N | Cl[C:12]([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:13].[NH2:14][C:15](=[NH:16])[N:17]([CH3:18])[CH2:19][C:20](=[O:21])[OH:22]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[O:13])[NH:14][C:15](=[NH:16])[N:17]([CH3:18])[CH2:19][C:20](=[O... | CCCCCCCCCCCC(=O)Cl.CN(CC(=O)O)C(=N)N | CCCCCCCCCCCC(=O)NC(=N)N(C)CC(=O)O | null | null | ClCCl.CC(=O)C | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[#7:5]-[C:6](=[N;D1;H1:7])-[NH2;D1;+0:8]>>[#7:5]-[C:6](=[N;D1;H1:7])-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | null | [] | null | null | null | null | In a dry 3-necked, round bottomed flask, equipped with a magnetic stirrer, a thermometer, a nitrogen inlet tube and the dropping funnel containing the dodecanoyl chloride solution, 7.34 g (56 mmol) of creatine is suspended, with stirring, in 50 ml of dry dichloromethane. To this suspension a catalytic amount (0.1 mmol)... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | null | HCl | ClCCl.CC(=O)C | null | null | CCCCCCCCCCCC(=O)Cl.CN(CC(=O)O)C(=N)N>ClCCl.CC(=O)C>CCCCCCCCCCCC(=O)NC(=N)N(C)CC(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c4dff51e1d564cf88832a0296a2750b7 | CCCCCCCCCCCCCCCC(=O)O.O=S(Br)Br>>CCCCCCCCCCCCCCCC(=O)Br | S(=O)(Br)Br.S(=O)(Br)Br.S(=O)(Br)Br.C(CCCCCCCCCCCCCCC)(=O)O>>C(CCCCCCCCCCCCCCC)(=O)Br | O[C:16]([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:17].O=S(Br)[Br:18]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16](=[O:17])[Br:18] | CCCCCCCCCCCCCCCC(=O)O.O=S(Br)Br | CCCCCCCCCCCCCCCC(=O)Br | null | null | O | Functional Group Interconversion | OtherReaction | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | null | Br-S(=O)-[Br;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]-[C:5]>>[Br;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]-[C:5] | null | [] | 50 | CELSIUS | null | null | In a dry 2-necked, round bottomed flask, equipped with a magnetic stirrer and fixed with a separatory funnel, containing 7.75 ml (100 mmol) of thionyl bromide, and a water condenser, is placed 12.82 g (50 mmol) of palmitic acid. Addition of the thionyl bromide is completed with heating to about 50° C. over the course o... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | null | HBr | O | 50 | null | CCCCCCCCCCCCCCCC(=O)O.O=S(Br)Br>O>CCCCCCCCCCCCCCCC(=O)Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c7baff985f1c4b459347dff42e8198b7 | CCCCCCCCCCCCCCCC(=O)Br.CN(CC(=O)O)C(=N)N>>CCCCCCCCCCCCCCCC(=O)NC(=N)N(C)CC(=O)O | C(CCCCCCCCCCCCCCC)(=O)Br.N1=CC=CC=C1.C(CCCCCCCCCCCCCCC)(=O)Br.O=C(O)CN(C)C(N)=N.C(CCCCCCCCCCCCCCC)(=O)Br.C(=O)=O.C(CCCCCCCCCCCCCCC)(=O)Br>>CN(C(=N)NC(CCCCCCCCCCCCCCC)=O)CC(=O)O | Br[C:16]([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:17].[NH2:18][C:19](=[NH:20])[N:21]([CH3:22])[CH2:23][C:24](=[O:25])[OH:26]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16](=... | CCCCCCCCCCCCCCCC(=O)Br.CN(CC(=O)O)C(=N)N | CCCCCCCCCCCCCCCC(=O)NC(=N)N(C)CC(=O)O | null | null | ClCCl.CC(=O)C | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | null | Br-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[#7:5]-[C:6](=[N;D1;H1:7])-[NH2;D1;+0:8]>>[#7:5]-[C:6](=[N;D1;H1:7])-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | null | [] | null | null | null | null | In a dry 3-necked, round bottomed flask, equipped with a magnetic stirrer, a thermometer, a nitrogen inlet tube and the dropping funnel containing the palmitoyl bromide solution, 10.99 g (60 mmol) of creatine is suspended, with stirring, in 100 ml of dry dichloromethane. To this suspension a catalytic amount (0.1 mmol)... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | null | HBr | ClCCl.CC(=O)C | null | null | CCCCCCCCCCCCCCCC(=O)Br.CN(CC(=O)O)C(=N)N>ClCCl.CC(=O)C>CCCCCCCCCCCCCCCC(=O)NC(=N)N(C)CC(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-010e4c3b4b894d4f82a7584883310830 | CCCCCCCCCCCCCCCCCCCCCC(=O)O.O=S(Cl)Cl>>CCCCCCCCCCCCCCCCCCCCCC(=O)Cl | S(=O)(Cl)Cl.S(=O)(Cl)Cl.S(=O)(Cl)Cl.C(CCCCCCCCCCCCCCCCCCCCC)(=O)O>>C(CCCCCCCCCCCCCCCCCCCCC)(=O)Cl | O[C:22]([CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:23].O=S(Cl)[Cl:24]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][... | CCCCCCCCCCCCCCCCCCCCCC(=O)O.O=S(Cl)Cl | CCCCCCCCCCCCCCCCCCCCCC(=O)Cl | null | null | O | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | null | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3] | null | [] | 45 | CELSIUS | 70 | MINUTE | In a dry 2-necked, round bottomed flask, equipped with a magnetic stirrer and fixed with a separatory funnel, containing 7.88 ml (108 mmol) of thionyl chloride, and a water condenser, is placed 20.44 g (60 mmol) of docosanoic acid. Addition of the thionyl chloride is completed with heating to about 45° C. over the cour... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | null | HCl | O | 45 | 1.166667 | CCCCCCCCCCCCCCCCCCCCCC(=O)O.O=S(Cl)Cl>O>CCCCCCCCCCCCCCCCCCCCCC(=O)Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f510a0453e704f45b9eea93c4e2fb61b | CCCCCCCCCCCCCCCCCCCCCC(=O)Cl.CN(CC(=O)O)C(=N)N>>CCCCCCCCCCCC(=O)NC(=N)N(C)CC(=O)O | C(CCCCCCCCCCCCCCCCCCCCC)(=O)Cl.N1=CC=CC=C1.C(CCCCCCCCCCCCCCCCCCCCC)(=O)Cl.O=C(O)CN(C)C(N)=N.C(CCCCCCCCCCCCCCCCCCCCC)(=O)Cl.C(=O)=O.C(CCCCCCCCCCCCCCCCCCCCC)(=O)Cl>>C(CCCCCCCCCCC)(=O)NC(N(C)CC(=O)O)=N | CCCCCCCCCC[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](Cl)=[O:13].[NH2:14][C:15](=[NH:16])[N:17]([CH3:18])[CH2:19][C:20](=[O:21])[OH:22]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[O:13])[NH:14][C:15](=[NH:16])[N:17]([CH3:18])[CH2:19]... | CCCCCCCCCCCCCCCCCCCCCC(=O)Cl.CN(CC(=O)O)C(=N)N | CCCCCCCCCCCC(=O)NC(=N)N(C)CC(=O)O | null | null | ClCCl.CC(=O)C | Acylation | OtherReaction | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | null | C-C-C-C-C-C-C-C-C-C-[CH2;D2;+0:1]-[C:2]-[C:3].Cl-[C;H0;D3;+0:4](=[O;D1;H0:5])-[C:6]-[C:7].[#7:8]-[C:9](=[N;D1;H1:10])-[NH2;D1;+0:11]>>[#7:8]-[C:9](=[N;D1;H1:10])-[NH;D2;+0:11]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[C:6]-[C:7].[C:3]-[C:2]-[CH3;D1;+0:1] | null | [] | null | null | null | null | In a dry 3-necked, round bottomed flask, equipped with a magnetic stirrer, a thermometer, a nitrogen inlet tube and the dropping funnel containing the docosanoyl chloride solution, 12.59 g (96 mmol) of creatine is suspended, with stirring, in 100 ml of dry dichloromethane. To this suspension a catalytic amount (0.1 mmo... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | null | HCl | ClCCl.CC(=O)C | null | null | CCCCCCCCCCCCCCCCCCCCCC(=O)Cl.CN(CC(=O)O)C(=N)N>ClCCl.CC(=O)C>CCCCCCCCCCCC(=O)NC(=N)N(C)CC(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f633fdfc486c446da53f2012bb61b1c9 | CCCCCC/C=C\CCCCCCCC(=O)O.O=S(Cl)Cl>>CCCCCC/C=C\CCCCCCCC(=O)Cl | S(=O)(Cl)Cl.S(=O)(Cl)Cl.S(=O)(Cl)Cl.C(CCCCCCC\C=C/CCCCCC)(=O)O>>C(CCCCCCC\C=C/CCCCCC)(=O)Cl | O[C:16]([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]/[CH:8]=[CH:7]\[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:17].O=S(Cl)[Cl:18]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]\[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16](=[O:17])[Cl:18] | CCCCCC/C=C\CCCCCCCC(=O)O.O=S(Cl)Cl | CCCCCC/C=C\CCCCCCCC(=O)Cl | null | null | O | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | null | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3] | null | [] | 40 | CELSIUS | 55 | MINUTE | In a dry 2-necked, round bottomed flask, equipped with a magnetic stirrer and fixed with a separatory funnel, containing 13.15 ml (180 mmol) of thionyl chloride, and a water condenser, is placed 28.45 ml (100 mmol) of palmitoleic acid. Addition of the thionyl chloride is completed with heating to about 40° C. over the ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | null | HCl | O | 40 | 0.916667 | CCCCCC/C=C\CCCCCCCC(=O)O.O=S(Cl)Cl>O>CCCCCC/C=C\CCCCCCCC(=O)Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-34c2f1a97cd04a1eb04c0d7754254a54 | NN=C(c1ccccc1)c1ccccc1.O=C(Cl)CCCCl>>O=C(CCCCl)NN=C(c1ccccc1)c1ccccc1 | O.ClCCCC(=O)Cl.C(C1=CC=CC=C1)(C1=CC=CC=C1)=NN.N1=CC=CC=C1>>C(C1=CC=CC=C1)(C1=CC=CC=C1)=NNC(CCCCl)=O | [NH2:7][N:8]=[C:9]([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1.Cl[C:2](=[O:1])[CH2:3][CH2:4][CH2:5][Cl:6]>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][Cl:6])[NH:7][N:8]=[C:9]([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | NN=C(c1ccccc1)c1ccccc1.O=C(Cl)CCCCl | O=C(CCCCl)NN=C(c1ccccc1)c1ccccc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | e1e032c84f30f6c93cf688039f3cc62747a034583f6175d60f7a0e21b27b6064 | 863011cce7fa0c660ac34aaac93028d203ff6ffc4b5a2233660e564db26255d2 | N=C(c1ccccc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[#7:6]=[C:7](-[c:8])-[c:9]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[#7:6]=[C:7](-[c:8])-[c:9] | null | [] | null | null | 0.5 | HOUR | 4-Chlorobutyryl chloride (57 mL, 510 mmol) is added to a solution of benzophenone hydrazone (100 g, 510 mmol) and pyridine (41 mL, 510 mmol) in anhydrous CH2Cl2 (520 mL) under nitrogen at a rate that maintained a gentle reflux throughout the addition. The mixture is stirred for 0.5 h and poured into water (1 L). The la... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Hydrazone | Hydrazone amide | null | null | c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | null | 0.5 | NN=C(c1ccccc1)c1ccccc1.O=C(Cl)CCCCl>C(Cl)Cl>O=C(CCCCl)NN=C(c1ccccc1)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cf9535f6b3cf4b6b98d9b139abe041d0 | CO.Cc1cccc(C(=O)O)n1>>COC(=O)c1cccc(C)n1 | CC1=CC=CC(=N1)C(=O)O.CO.C(CCl)Cl>>COC(=O)C1=NC(=CC=C1)C | O[CH3:1].[OH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([CH3:10])[n:11]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([CH3:10])[n:11]1 | CO.Cc1cccc(C(=O)O)n1 | COC(=O)c1cccc(C)n1 | null | CN(C1=CC=NC=C1)C | C(Cl)Cl | Heteroatom Alkylation and Arylation | Esterification of Carboxylic Acids | 961bfcd5802efbb4a2d5a1e38cbfb6654b5b78f769c3570df49b858a6f105ab6 | 0a622556a49b258b9020bd3a5bdd1fa9237e7093cf9b09de3a6b575ffe935dcd | c1ccncc1 | O-[CH3;D1;+0:1].[#7;a:2]:[c:3]-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6]>>[#7;a:2]:[c:3]-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-[CH3;D1;+0:1] | null | [] | 0 | CELSIUS | 6 | HOUR | To a suspension of 6-methyl-pyridine-2-carboxylic Acid (10 g, 72.9 mmol) in CH2Cl2 (200 mL) cooled to 0° C. is added MeOH (10 mL), 4-dimethylaminopyridine (11.6 g, 94.8 mmol), and EDC (18.2 g, 94.8 mmol). The mixture is stirred at RT for 6 h, washed with water and brine, and dried over Na2SO4. The mixture is filtered a... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccncc1 | HO- | CN(C1=CC=NC=C1)C.C(Cl)Cl | 0 | 6 | CO.Cc1cccc(C(=O)O)n1>CN(C1=CC=NC=C1)C.C(Cl)Cl>COC(=O)c1cccc(C)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8f57fa29e9ac49ff89af3b6a105da1ce | C=CC(C)=O.Nc1cccc(Br)c1>>Cc1ccnc2cc(Br)ccc12 | C(=C)C(=O)C.OS(=O)(=O)O.BrC=1C=C(N)C=CC1>>BrC1=CC=C2C(=CC=NC2=C1)C | O=[C:2]([CH3:1])[CH:3]=[CH2:4].[NH2:5][c:6]1[cH:7][c:8]([Br:9])[cH:10][cH:11][cH:12]1>>[CH3:1][c:2]1[cH:3][cH:4][n:5][c:6]2[cH:7][c:8]([Br:9])[cH:10][cH:11][c:12]12 | C=CC(C)=O.Nc1cccc(Br)c1 | Cc1ccnc2cc(Br)ccc12 | null | null | O1CCOCC1 | Aromatic Heterocycle Formation | OtherReaction | 7d164ccd2a961120aaa0574a88528d2776564b1fb1b3cf378b67e98287524e77 | e8439cfe055023d9132dc0595e690b94c7d2d437ab1f19554009dc0b9bd47b59 | c1ccc2ncccc2c1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH;D2;+0:3]=[CH2;D1;+0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10]>>[C;D1;H3:2]-[c;H0;D3;+0:1]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[n;H0;D2;+0:5]:[c:6](:[c:7]):[c;H0;D3;+0:8]:1:[c:9]:[c:10] | null | [] | null | null | 1 | HOUR | H2SO4 (14.4 mL, 270 mmol) is added to a solution of 3-bromoaniline (Aldrich, 30.0 g, 174 mmol) in 1,4-dioxane (1 L) at RT. The mixture is heated to reflux and treated with methyl vinyl ketone (Aldrich, 19.5 mL, 270 mmol) in 1,4-dioxane (50 mL) dropwise over 3 h. Heating is continued for 1 h after the addition, followed... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine.Vinyl | null | c1ccccc1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HO- | O1CCOCC1 | null | 1 | C=CC(C)=O.Nc1cccc(Br)c1>O1CCOCC1>Cc1ccnc2cc(Br)ccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d53f2e58c9774e8984be8aeaf795a267 | CO.O=C(O)CCc1ccc(-c2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)cc1>>COC(=O)CCc1ccc(-c2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)cc1 | N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC(=CC=C21)C2=CC=C(C=C2)CCC(=O)O.Cl.CO>>COC(CCC1=CC=C(C=C1)C1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC=CC=C1)CCC2)=O | [CH3:1][OH:2].O[C:3](=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10](-[c:11]2[cH:12][cH:13][c:14]3[c:15](-[c:16]4[c:17](-[c:18]5[cH:19][cH:20][cH:21][cH:22][n:23]5)[n:24][n:25]5[c:26]4[CH2:27][CH2:28][CH2:29]5)[cH:30][cH:31][n:32][c:33]3[cH:34]2)[cH:35][cH:36]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][cH:9][c... | CO.O=C(O)CCc1ccc(-c2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)cc1 | COC(=O)CCc1ccc(-c2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)cc1 | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccc(-c2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C;D1;H3:5]-[OH;D1;+0:6]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:6]-[C;D1;H3:5] | null | [] | null | null | null | null | Into a 100 mL roundbottom flask is placed 3-{4-[4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)quinolin-7-yl]phenyl}propionic Acid (Example 30 before reverse phase purification) (160 mg, 0.35 mmol), 20 mL of MeOH, and 1.5 mL of conc HCl solution. The mixture is refluxed 3 h, and solvent removed under reduc... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1.c1ccncc1.c1cc2n(n1)CCC2.c1ccc2ncccc2c1 | HO- | null | null | null | CO.O=C(O)CCc1ccc(-c2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)cc1>>COC(=O)CCc1ccc(-c2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9c29f6f8319341f29ceb15208efbf7dd | O=S(=O)(OCC(F)(F)F)C(F)(F)F.Oc1ccc(-c2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)cc1>>FC(F)(F)COc1ccc(-c2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)cc1.O=C(O)C(F)(F)F | [H-].[Na+].N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC(=CC=C21)C2=CC=C(C=C2)O.FC(COS(=O)(=O)C(F)(F)F)(F)F>>FC(C(=O)O)(F)F.N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC(=CC=C21)C2=CC=C(C=C2)OCC(F)(F)F | O=S(=[O:37])([O:39][CH2:5][C:2]([F:1])([F:3])[F:4])[C:40]([F:41])([F:42])[F:43].[OH:6][c:7]1[cH:8][cH:9][c:10](-[c:11]2[cH:12][cH:13][c:14]3[c:15](-[c:16]4[c:17](-[c:18]5[cH:19][cH:20][cH:21][cH:22][n:23]5)[n:24][n:25]5[c:26]4[CH2:27][CH2:28][CH2:29]5)[cH:30][cH:31][n:32][c:33]3[cH:34]2)[cH:35][cH:36]1>>[F:1][C:2]([F:3... | O=S(=O)(OCC(F)(F)F)C(F)(F)F.Oc1ccc(-c2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)cc1 | FC(F)(F)COc1ccc(-c2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)cc1.O=C(O)C(F)(F)F | null | null | CN(C)C=O | Acylation | OtherReaction | 2d3fe6bfc9e5d1c85305db82870e16e2eb4a5b7417da03f96414efa97cc8afe5 | 7e6d092a6a905cf2ea3fa6e2722443d9dc2b97b08244e142b4e8ebcd7bcd451f | c1ccc(-c2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)cc1 | O=S(=[O;H0;D1;+0:1])(-[O;H0;D2;+0:2]-[CH2;D2;+0:3]-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[F;D1;H0:7])-[C;H0;D4;+0:8](-[F;D1;H0:9])(-[F;D1;H0:10])-[F;D1;H0:11].[OH;D1;+0:12]-[c:13](:[c:14]):[c:15]>>[F;D1;H0:9]-[C;H0;D4;+0:8](-[F;D1;H0:10])(-[F;D1;H0:11])-[C:16](=[O;H0;D1;+0:1])-[OH;D1;+0:2].[F;D1;H0:5]-[C:4](-[F;D1;H0:6])(-... | null | [] | 70 | CELSIUS | null | null | Into a 25 mL glass pressure tube fitted with Teflon screw cap and magnetic bar is placed 4-[4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)quinolin-7-yl]phenol (Example 7 before reverse phase HPLC purification); 0.100 g, 0.25 mmol), DMF (2 mL), trifluoro-methanesulfonic acid 2,2,2-trifluoroethyl ester (0.0... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Aromatic alcohol | Trifluoro group.Carboxylic acid.Ether | null | null | c1ccccc1.c1ccncc1.c1cc2n(n1)CCC2.c1ccc2ncccc2c1 | Other | CN(C)C=O | 70 | null | O=S(=O)(OCC(F)(F)F)C(F)(F)F.Oc1ccc(-c2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)cc1>CN(C)C=O>FC(F)(F)COc1ccc(-c2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)cc1.O=C(O)C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f998128849b945c88d02b7863ec5f63c | CC(C)(C)OC(=O)NCCN.O=C(O)c1ccc(-c2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)cc1>>CC(C)(C)OC(=O)NCCNC(=O)c1ccc(-c2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)cc1 | N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC(=CC=C21)C2=CC=C(C(=O)O)C=C2.C(C)(C)(C)OC(NCCN)=O.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=C2)N=N1.F[P-](F)(F)(F)(F)F>>C(C)(C)(C)OC(NCCNC(C1=CC=C(C=C1)C1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC=CC=C1)CCC2)=O)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][NH2:11].O[C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17](-[c:18]2[cH:19][cH:20][c:21]3[c:22](-[c:23]4[c:24](-[c:25]5[cH:26][cH:27][cH:28][cH:29][n:30]5)[n:31][n:32]5[c:33]4[CH2:34][CH2:35][CH2:36]5)[cH:37][cH:38][n:39][c:40]3[cH:41]2)[cH:42][cH:43]1>>[CH3... | CC(C)(C)OC(=O)NCCN.O=C(O)c1ccc(-c2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)cc1 | CC(C)(C)OC(=O)NCCNC(=O)c1ccc(-c2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)cc1 | null | null | CN(C)C=O.CCOC(=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(-c2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 8 | HOUR | 4-[4-(2-Pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-yl]-benzoic acid (Example 41 before reverse phase chromatography, 0.08 g, 0.185 mmol), (2-aminoethyl)-carbamic acid tert-butyl ester (0.036 g, 0.2 mmol), N—N-Diisopropylethylamine (0.08 mL, 0.46 mmol) and HBTU (0.076 g, 0.2 mmol) are mixed in 10... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccncc1.c1cc2n(n1)CCC2.c1ccc2ncccc2c1 | HO- | CN(C)C=O.CCOC(=O)C | null | 8 | CC(C)(C)OC(=O)NCCN.O=C(O)c1ccc(-c2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)cc1>CN(C)C=O.CCOC(=O)C>CC(C)(C)OC(=O)NCCNC(=O)c1ccc(-c2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fb29c5481180486292375ef17481b9f6 | CCCCCCCCCCCC(=O)c1ccc2cc(O)ccc2c1.CN>>CCCCCCCCCCCC(=O)c1ccc2cc(NC)ccc2c1 | CN.Cl.OC1=CC2=CC=C(C=C2C=C1)C(CCCCCCCCCCC)=O.[OH-].[Na+]>>C(CCCCCCCCCCC)(=O)C=1C=C2C=CC(=CC2=CC1)NC | O[c:19]1[cH:18][c:17]2[cH:16][cH:15][c:14]([C:12]([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:13])[cH:25][c:24]2[cH:23][cH:22]1.[NH2:20][CH3:21]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17]2[cH:18][c:19... | CCCCCCCCCCCC(=O)c1ccc2cc(O)ccc2c1.CN | CCCCCCCCCCCC(=O)c1ccc2cc(NC)ccc2c1 | null | null | O | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | de3f59587802c5fbb12e4a6a2c857c24b6ffebe3ab2996064124a48d15e13249 | d1ce63afd91e9f43d522aac919284b7f154a7b1ed206dc2b146286d54897dcb1 | c1ccc2ccccc2c1 | O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[NH2;D1;+0:7]>>[C;D1;H3:6]-[NH;D2;+0:7]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 67 | [{"value": 67.0, "product": "C(CCCCCCCCCCC)(=O)C=1C=C2C=CC(=CC2=CC1)NC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.0, "product": "C(CCCCCCCCCCC)(=O)C=1C=C2C=CC(=CC2=CC1)NC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 48 | HOUR | MeNH2.HCl (11.0 g, 0.13 mol) was added to a mixture of 2-hydroxy-6-dodecanoylnaphthalene (8.0 g, 25 mmol), Na2S2O5 (12 g, 61 mmol), NaOH (5.2 g, 0.13 mol) and water (100 ml) in a high-pressure tube. The resulting mixture was stirred at 140° C. for 48 hours, followed by filtration to collect a solid. The solid was suffi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Primary amine | Secondary amine | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | HO- | O | 140 | 48 | CCCCCCCCCCCC(=O)c1ccc2cc(O)ccc2c1.CN>O>CCCCCCCCCCCC(=O)c1ccc2cc(NC)ccc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a91725a931084092b21bc00e3cae7e72 | CNc1ccc2cc(Br)ccc2c1>>CNc1ccc2cc(C#N)ccc2c1 | BrC=1C=C2C=CC(=CC2=CC1)NC.[Cu]C#N>>CNC=1C=C2C=CC(=CC2=CC1)C#N | Br[c:8]1[cH:7][c:6]2[cH:5][cH:4][c:3]([NH:2][CH3:1])[cH:14][c:13]2[cH:12][cH:11]1>>[CH3:1][NH:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][c:8]([C:9]#[N:10])[cH:11][cH:12][c:13]2[cH:14]1 | CNc1ccc2cc(Br)ccc2c1 | CNc1ccc2cc(C#N)ccc2c1 | null | null | N1=CC=CC=C1 | Miscellaneous | OtherReaction | 6b2e76ea725bec0f478425d10a420e3873896604ae33af70efc4c0461fad2cf4 | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | c1ccc2ccccc2c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]>>[N;D1;H0:6]#[C:7]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 71 | [{"value": 71.0, "product": "CNC=1C=C2C=CC(=CC2=CC1)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.0, "product": "CNC=1C=C2C=CC(=CC2=CC1)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 220 | CELSIUS | 4 | HOUR | A solution of 6-bromo-N-methyl-2-naphthylamine (2.0 g, 8.5 mmol) in pyridine (50 ml) was added to copper (I) cyanide (1.1 g, 12.3 mmol). The mixture was stirred at 220° C. for 4 hours. The reaction mixture was allowed to cool to room temperature, extracted with dichloromethane, washed with an aqueous solution of hethyl... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | Br- | N1=CC=CC=C1 | 220 | 4 | CNc1ccc2cc(Br)ccc2c1>N1=CC=CC=C1>CNc1ccc2cc(C#N)ccc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2e260b1673e6470d921969f0b18aab52 | CNc1ccc2cc(C#N)ccc2c1.O=S(=O)(O)O>>CNc1ccc2cc(C=O)ccc2c1 | S(O)(O)(=O)=O.[H-].C(C(C)C)[Al+]CC(C)C.CNC=1C=C2C=CC(=CC2=CC1)C#N.[Cl-].[NH4+]>>C(=O)C=1C=C2C=CC(=CC2=CC1)NC | N#[C:9][c:8]1[cH:7][c:6]2[cH:5][cH:4][c:3]([NH:2][CH3:1])[cH:14][c:13]2[cH:12][cH:11]1.O=S(O)(O)=[O:10]>>[CH3:1][NH:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][c:8]([CH:9]=[O:10])[cH:11][cH:12][c:13]2[cH:14]1 | CNc1ccc2cc(C#N)ccc2c1.O=S(=O)(O)O | CNc1ccc2cc(C=O)ccc2c1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 26082e4725cd2a7c1eb6362fc44981286c2087c015aba2f1b570103659ffb41e | e783d65987caa6ceae095ff666413e4c8d25ead96c003eb4f99d66fc68c0b0bb | c1ccc2ccccc2c1 | N#[C;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].O-S(-O)(=O)=[O;H0;D1;+0:5]>>[O;H0;D1;+0:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 89 | [{"value": 89.0, "product": "C(=O)C=1C=C2C=CC(=CC2=CC1)NC", "details": "PERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 4 | HOUR | A solution of 6-methylamino-2-naphthonitrile (0.84 g, 4.6 mmol) prepared above in toluene (50 ml) was mixed with diisobutylaluminum hydride (9 ml, 1.0M (in toluene)) under a nitrogen atmosphere at −70° C. The mixture was stirred at −78° C. for 30 minutes and at room temperature for 4 hours. The mixture was added to a s... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Aldehyde | null | null | c1ccc2ccccc2c1 | HO- | C1(=CC=CC=C1)C | -78 | 4 | CNc1ccc2cc(C#N)ccc2c1.O=S(=O)(O)O>C1(=CC=CC=C1)C>CNc1ccc2cc(C=O)ccc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-29af8fcf6b5d4a7ebf5b3ffd1d149c60 | CCCCCCCCCCCCCl.COc1ccc2ccccc2c1.O=[N+]([O-])c1ccccc1>>CCCCCCCCCCCC(=O)c1ccc2cc(OC)ccc2c1 | Cl.COC1=CC2=CC=CC=C2C=C1.[Cl-].[Al+3].[Cl-].[Cl-].[N+](=O)([O-])C1=CC=CC=C1.C(CCCCCCCCCCC)Cl>>COC1=CC2=CC=C(C=C2C=C1)C(CCCCCCCCCCC)=O | Cl[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].[cH:14]1[cH:15][cH:16][c:17]2[cH:18][c:19]([O:20][CH3:21])[cH:22][cH:23][c:24]2[cH:25]1.[O-][N+](c1ccccc1)=[O:13]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[O:13])[c:14]1[cH:15][cH:16]... | CCCCCCCCCCCCCl.COc1ccc2ccccc2c1.O=[N+]([O-])c1ccccc1 | CCCCCCCCCCCC(=O)c1ccc2cc(OC)ccc2c1 | null | null | null | Functional Group Interconversion | OtherReaction | a9128a0af2a4286c9286039fe20650f14721e9388d501c4cbd9e7e604a639916 | 70f17c63a4b7105b0ea445fe2f2d68b2827b89eef89e402d0e06628e53d5c930 | c1ccc2ccccc2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[O-]-[N+](=[O;H0;D1;+0:4])-c1:c:c:c:c:c:1.[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[C:3]-[C:2]-[C;H0;D3;+0:1](=[O;H0;D1;+0:4])-[c;H0;D3;+0:7](:[c:6]:[c:5]):[c:8]:[c:9] | 64.2 | [{"value": 64.2, "product": "COC1=CC2=CC=C(C=C2C=C1)C(CCCCCCCCCCC)=O", "details": "PERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | 12 | HOUR | 2-Methoxynaphthalene (30.1 g, 0.19 mol) was added to a solution of aluminum chloride (32.9 g, 0.25 mol) in anhydrous nitrobenzene under a nitrogen atmosphere. To the mixture was slowly added dropwise lauryl chloride (41.6 g, 0.19 mol) at 10-13° C. over 15 minutes. The resulting mixture was stirred at 5° C. for 2 hours ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Nitro group | Ketone | c1ccc2ccccc2c1.c1ccccc1 | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | HCl | null | 5 | 12 | CCCCCCCCCCCCCl.COc1ccc2ccccc2c1.O=[N+]([O-])c1ccccc1>>CCCCCCCCCCCC(=O)c1ccc2cc(OC)ccc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a0f61b78c625438bb6a9ed18d1ebb3d2 | CCCCCCCCCCCC(=O)c1ccc2cc(OC)ccc2c1.CNC>>CCCCCCCCCCCC(=O)c1ccc2cc(N(C)C)ccc2c1 | CNC.CN(C)P(=O)(N(C)C)N(C)C.COC1=CC2=CC=C(C=C2C=C1)C(CCCCCCCCCCC)=O>>CCCCCCCCCCCC(=O)C1=CC2=C(C=C1)C=C(C=C2)N(C)C | CO[c:19]1[cH:18][c:17]2[cH:16][cH:15][c:14]([C:12]([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:13])[cH:26][c:25]2[cH:24][cH:23]1.[NH:20]([CH3:21])[CH3:22]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17]2[c... | CCCCCCCCCCCC(=O)c1ccc2cc(OC)ccc2c1.CNC | CCCCCCCCCCCC(=O)c1ccc2cc(N(C)C)ccc2c1 | null | null | C1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Displacement of ethoxy group by secondary amine | 6326e1db93c48a78fa64ccca67243ca05322ff7c1916e72f48454573b2cf23b4 | f41a0ac1ece338534be38b696cb3541e6003cebbbc2e76e91361a568e6946ab0 | c1ccc2ccccc2c1 | C-O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[NH;D2;+0:7]-[C;D1;H3:8]>>[C;D1;H3:6]-[N;H0;D3;+0:7](-[C;D1;H3:8])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 66 | [{"value": 66.0, "product": "CCCCCCCCCCCC(=O)C1=CC2=C(C=C1)C=C(C=C2)N(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Li (0.5 g, 70 mmol) was added to HMPA (20 ml) and benzene (30 ml), and then dimethylamine (3.5 g, 78 mmol) was added dropwise thereto. The mixture was violently stirred for one hour. To the resulting mixture was added 2-methoxy-6-dodecanoylnaphthalene (7.3 g, 22 mmol) prepared in Comparative Example 1-(1) all at one ti... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Tertiary amine | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | HO- | C1=CC=CC=C1 | null | 1 | CCCCCCCCCCCC(=O)c1ccc2cc(OC)ccc2c1.CNC>C1=CC=CC=C1>CCCCCCCCCCCC(=O)c1ccc2cc(N(C)C)ccc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-69b8d738db8e4760bc17caad85c5f98d | Cc1ccc(Cl)cc1.Cc1ccc(S(=O)c2ccc(C)cc2)cc1>>Cc1ccc([S+](c2ccc(C)cc2)c2ccc(C)cc2)cc1.[Cl-] | CC1=CC=C(C=C1)S(=O)C1=CC=C(C=C1)C.ClC1=CC=C(C=C1)C>>[Cl-].CC1=CC=C(C=C1)[S+](C1=CC=C(C=C1)C)C1=CC=C(C=C1)C | [c:14]1([Cl:23])[cH:15][cH:16][c:17]([CH3:18])[cH:19][cH:20]1.O=[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:22][cH:21]1)[c:7]1[cH:8][cH:9][c:10]([CH3:11])[cH:12][cH:13]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S+:6]([c:7]2[cH:8][cH:9][c:10]([CH3:11])[cH:12][cH:13]2)[c:14]2[cH:15][cH:16][c:17]([CH3:18])[cH:19][cH:20]2)[cH:21][cH... | Cc1ccc(Cl)cc1.Cc1ccc(S(=O)c2ccc(C)cc2)cc1 | Cc1ccc([S+](c2ccc(C)cc2)c2ccc(C)cc2)cc1.[Cl-] | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | b7fca8eeb731d381e222beb473d8e55fa6d5f2f0a2f48cd3a0fb40a9c5698a75 | 31d32474c31cc1c196190b139dce413ab579369dcdb12c0b32f09d6175566440 | c1ccc([S+](c2ccccc2)c2ccccc2)cc1 | O=[S;H0;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7].[Cl;H0;D1;+0:8]-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[Cl-;H0;D0:8].[c:6]:[c:5](-[S+;H0;D3:1](-[c:2](:[c:3]):[c:4])-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]):[c:7] | null | [] | null | null | null | null | The target compound was obtained by following the procedure of Synthesis Example 1 aside from using bis(4-methylphenyl)sulfoxide instead of the diphenyl sulfoxide and 4-chlorotoluene instead of the chlorobenzene in Synthesis Example 1, and increasing the amount of water for extraction.
Conditions: See reaction.notes.pr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Sulfoxide | null | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | Other | O | null | null | Cc1ccc(Cl)cc1.Cc1ccc(S(=O)c2ccc(C)cc2)cc1>O>Cc1ccc([S+](c2ccc(C)cc2)c2ccc(C)cc2)cc1.[Cl-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-952cf908abad47d3bc945c1b45e936dc | CC(C)(C)c1ccc(Br)cc1.CC(C)(C)c1ccc(S(=O)c2ccc(C(C)(C)C)cc2)cc1>>CC(C)(C)c1ccc([S+](c2ccc(C(C)(C)C)cc2)c2ccc(C(C)(C)C)cc2)cc1.[Br-] | C(C)(C)(C)C1=CC=C(C=C1)S(=O)C1=CC=C(C=C1)C(C)(C)C.C(C)(C)(C)C1=CC=C(C=C1)Br>>[Br-].C(C)(C)(C)C1=CC=C(C=C1)[S+](C1=CC=C(C=C1)C(C)(C)C)C1=CC=C(C=C1)C(C)(C)C | [c:10]1([Br:32])[cH:11][cH:12][c:13]([C:14]([CH3:15])([CH3:16])[CH3:17])[cH:18][cH:19]1.O=[S:9]([c:8]1[cH:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:31][cH:30]1)[c:20]1[cH:21][cH:22][c:23]([C:24]([CH3:25])([CH3:26])[CH3:27])[cH:28][cH:29]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([S+:9]([c:10]2[cH:1... | CC(C)(C)c1ccc(Br)cc1.CC(C)(C)c1ccc(S(=O)c2ccc(C(C)(C)C)cc2)cc1 | CC(C)(C)c1ccc([S+](c2ccc(C(C)(C)C)cc2)c2ccc(C(C)(C)C)cc2)cc1.[Br-] | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | b7fca8eeb731d381e222beb473d8e55fa6d5f2f0a2f48cd3a0fb40a9c5698a75 | 31d32474c31cc1c196190b139dce413ab579369dcdb12c0b32f09d6175566440 | c1ccc([S+](c2ccccc2)c2ccccc2)cc1 | O=[S;H0;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7].[Br;H0;D1;+0:8]-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[Br-;H0;D0:8].[c:11]:[c:10]:[c;H0;D3;+0:9](-[S+;H0;D3:1](-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7]):[c:12]:[c:13] | null | [] | null | null | null | null | The target compound was obtained by following the procedure of Synthesis Example 1 aside from using bis(4-tert-butylphenyl)sulfoxide instead of the diphenyl sulfoxide and 4-tert-butylbromobenzene instead of the chlorobenzene in Synthesis Example 1, and increasing the amount of water for extraction.
Conditions: See reac... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Sulfoxide | null | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | Other | O | null | null | CC(C)(C)c1ccc(Br)cc1.CC(C)(C)c1ccc(S(=O)c2ccc(C(C)(C)C)cc2)cc1>O>CC(C)(C)c1ccc([S+](c2ccc(C(C)(C)C)cc2)c2ccc(C(C)(C)C)cc2)cc1.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-49dfe19fd3e547f8a63a6c386e43abce | C1CCSC1.O=C(CBr)c1ccccc1>>O=C(C[S+]1CCCC1)c1ccccc1.[Br-] | C(C(=O)C1=CC=CC=C1)Br.S1CCCC1.O.C(C)OCC>>[Br-].C(C(=O)C1=CC=CC=C1)[S+]1CCCC1 | [S:4]1[CH2:5][CH2:6][CH2:7][CH2:8]1.[O:1]=[C:2]([CH2:3][Br:15])[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[O:1]=[C:2]([CH2:3][S+:4]1[CH2:5][CH2:6][CH2:7][CH2:8]1)[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[Br-:15] | C1CCSC1.O=C(CBr)c1ccccc1 | O=C(C[S+]1CCCC1)c1ccccc1.[Br-] | null | null | [N+](=O)([O-])C | Functional Group Interconversion | OtherReaction | 85f24012cc235dcc2174546a7acc1a27fcb95f75402893a368fc99d3ab479d23 | 243e6d69a1ef4217446cfc3f9974b61aa23bfb74648883a134f35ef9c12f90f1 | O=C(C[S+]1CCCC1)c1ccccc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3](=[O;D1;H0:4])-[c:5].[C:6]1-[C:7]-[C:8]-[C:9]-[S;H0;D2;+0:10]-1>>[Br-;H0;D0:1].[O;D1;H0:4]=[C:3](-[c:5])-[CH2;D2;+0:2]-[S+;H0;D3:10]1-[C:6]-[C:7]-[C:8]-[C:9]-1 | null | [] | null | null | 4 | HOUR | 88.2 g (0.44 mole) of phenacyl bromide and 39.1 g (0.44 mole) of tetrahydrothiophene were dissolved in 220 g of nitromethane, which was stirred for 4 hours at room temperature. 800 g of water and 400 g of diethyl ether were added to the reaction solution whereupon the mixture separated into two layers. The aqueous laye... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Monosulfide | Ketone | C1CCSC1 | C1CC[S+]C1 | C1CC[S+]C1.c1ccccc1 | null | [N+](=O)([O-])C | null | 4 | C1CCSC1.O=C(CBr)c1ccccc1>[N+](=O)([O-])C>O=C(C[S+]1CCCC1)c1ccccc1.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d3b0e7f48d424e0781af1e3bf1e69ea3 | COS(=O)(=O)OC.CSc1ccccc1>>C[S+](C)c1ccccc1.O=S(=O)([O-])O | C1(=CC=CC=C1)SC.S(=O)(=O)(OC)OC.O>>S(=O)(=O)(O)[O-].C[S+](C1=CC=CC=C1)C | C[O:13][S:11](=[O:10])(=[O:12])[O:14][CH3:3].[CH3:1][S:2][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1>>[CH3:1][S+:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1.[O:10]=[S:11](=[O:12])([O-:13])[OH:14] | COS(=O)(=O)OC.CSc1ccccc1 | C[S+](C)c1ccccc1.O=S(=O)([O-])O | null | null | C(C)OCC | Protection | OtherReaction | a27abd92746860a3a2d8385da23c5a6d6da58ebae8a1f56d03eb57f286c2ced2 | fd6f5097e6b4b848368a6acbac5c2fc1c3716ca071296766b72a424c32f5899c | c1ccccc1 | C-[O;H0;D2;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[O;H0;D2;+0:5]-[CH3;D1;+0:6].[C;D1;H3:7]-[S;H0;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[C;D1;H3:7]-[S+;H0;D3:8](-[CH3;D1;+0:6])-[c:9](:[c:10]):[c:11].[O-;H0;D1:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[OH;D1;+0:5] | null | [] | null | null | null | null | 6.2 g (0.05 mole) of thioanisole and 6.9 g (0.055 mole) of dimethyl sulfate were stirred for 12 hours at room temperature. 100 g of water and 50 ml of diethyl ether were added to the reaction solution whereupon the mixture separated into two layers. The aqueous layer was taken out, which was an aqueous solution of the ... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | null | null | null | c1ccccc1 | Other | C(C)OCC | null | null | COS(=O)(=O)OC.CSc1ccccc1>C(C)OCC>C[S+](C)c1ccccc1.O=S(=O)([O-])O |
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