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-03f5875dd8004e5d8769e7b6f33d3805 | COC(=O)c1cc(Br)ccc1O.OB(O)c1ccc(F)c(Cl)c1>>COC(=O)c1cc(-c2ccc(F)c(Cl)c2)ccc1O | COC(C1=C(C=CC(=C1)Br)O)=O.ClC=1C=C(C=CC1F)B(O)O.C(C1=CC=CC=C1)(=O)OC.[Li+].[OH-].O.C1CCOC1.C(C)O>>COC(=O)C=1C=C(C=CC1O)C1=CC(=C(C=C1)F)Cl | Br[c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:18]([OH:19])[cH:17][cH:16]1.OB(O)[c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([Cl:14])[cH:15]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[c:13]([Cl:14])[cH:15]2)[cH:16][cH:17][c:18]1[OH:19] | COC(=O)c1cc(Br)ccc1O.OB(O)c1ccc(F)c(Cl)c1 | COC(=O)c1cc(-c2ccc(F)c(Cl)c2)ccc1O | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]-[C:6](-[#8:7])=[O;D1;H0:8].O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[#8:7]-[C:6](=[O;D1;H0:8])-[c:5]:[c:4]:[c;H0;D3;+0:1](-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]):[c:2]:[c:3] | null | [] | null | null | null | null | The resin-bound 3′-chloro-4′-fluoro-4-hydroxy-biphenyl-3-carboxylic acid methyl ester was prepared with 1.0 g (3.0 mmol) of above resin-bound 5-bromo-2-hydroxy-benzoic acid methyl ester and 1.6 g (9.0 mmol) of 3-chloro-4-fluoro-phenylboronic acid as described in Procedure K. The resulting resin-bound methyl benzoate wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | HBr.B | null | null | null | COC(=O)c1cc(Br)ccc1O.OB(O)c1ccc(F)c(Cl)c1>>COC(=O)c1cc(-c2ccc(F)c(Cl)c2)ccc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-17f2b40259684ceeaa4d720cb6a5b410 | COC(=O)[C@H](Cc1ccc(Br)cc1)NC(=O)c1cc(-c2ccc(F)c(Cl)c2)ccc1O.OB(O)c1cccc(C(F)(F)F)c1>>O=C(N[C@@H](Cc1ccc(-c2cccc(C(F)(F)F)c2)cc1)C(=O)O)c1cc(-c2ccc(F)c(Cl)c2)ccc1O | [Li+].[OH-].O.C1CCOC1.CO.COC([C@H](CC1=CC=C(C=C1)Br)NC(=O)C=1C=C(C=CC1O)C1=CC(=C(C=C1)F)Cl)=O.FC(C=1C=C(C=CC1)B(O)O)(F)F>>ClC=1C=C(C=CC1F)C1=CC(=C(C=C1)O)C(=O)N[C@H](C(=O)O)CC1=CC=C(C=C1)C1=CC(=CC=C1)C(F)(F)F | C[O:24][C:22]([C@@H:4]([NH:3][C:2](=[O:1])[c:25]1[cH:26][c:27](-[c:28]2[cH:29][cH:30][c:31]([F:32])[c:33]([Cl:34])[cH:35]2)[cH:36][cH:37][c:38]1[OH:39])[CH2:5][c:6]1[cH:7][cH:8][c:9](Br)[cH:20][cH:21]1)=[O:23].OB(O)[c:10]1[cH:11][cH:12][cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19]1>>[O:1]=[C:2]([NH:3][C@@H:4]([CH2... | COC(=O)[C@H](Cc1ccc(Br)cc1)NC(=O)c1cc(-c2ccc(F)c(Cl)c2)ccc1O.OB(O)c1cccc(C(F)(F)F)c1 | O=C(N[C@@H](Cc1ccc(-c2cccc(C(F)(F)F)c2)cc1)C(=O)O)c1cc(-c2ccc(F)c(Cl)c2)ccc1O | null | null | null | C-C Coupling | OtherReaction | 04157bef51d5543c035526858b11d2af2b78e75d38cd85edf56b617e6aebc946 | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | O=C(NCCc1ccc(-c2ccccc2)cc1)c1cccc(-c2ccccc2)c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-[O;H0;D2;+0:6]-[C:7](-[C:8])=[O;D1;H0:9].O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[C:8]-[C:7](=[O;D1;H0:9])-[OH;D1;+0:6].[c:12]:[c:11]:[c;H0;D3;+0:10](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:13]:[c:14] | 44.8 | [{"value": 44.8, "product": "ClC=1C=C(C=CC1F)C1=CC(=C(C=C1)O)C(=O)N[C@H](C(=O)O)CC1=CC=C(C=C1)C1=CC(=CC=C1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | The resin-bound 3-(4-bromo-phenyl)-(2S)-2-[(3′-chloro-4′-fluoro -4-hydroxy-biphenyl-3-carbonyl)-amino]-propionic acid methyl ester (100 mg, 0.3 mmol) was reacted with 3-trifluoromethyl-phenylboronic acid (285 mg, 1.5 mmol) by following Procedure K. The resulting resin-bound methyl ester was hydrolyzed with LiOH/H2O/THF... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HBr.B | null | null | 4 | COC(=O)[C@H](Cc1ccc(Br)cc1)NC(=O)c1cc(-c2ccc(F)c(Cl)c2)ccc1O.OB(O)c1cccc(C(F)(F)F)c1>>O=C(N[C@@H](Cc1ccc(-c2cccc(C(F)(F)F)c2)cc1)C(=O)O)c1cc(-c2ccc(F)c(Cl)c2)ccc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-700ce5cf756c4b6ab432a032d6163755 | COC(=O)[C@H](Cc1ccc(OCc2ccccc2)cc1)NC(=O)c1cc(Br)ccc1O>>COC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)c1ccccc1O | COC([C@H](CC1=CC=C(C=C1)OCC1=CC=CC=C1)NC(C1=C(C=CC(=C1)Br)O)=O)=O>>COC([C@H](CC1=CC=C(C=C1)O)NC(C1=C(C=CC=C1)O)=O)=O | Br[c:19]1[cH:18][c:17]([C:15]([NH:14][C@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][c:7]2[cH:8][cH:9][c:10]([O:11]Cc3ccccc3)[cH:12][cH:13]2)=[O:16])[c:22]([OH:23])[cH:21][cH:20]1>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([OH:11])[cH:12][cH:13]1)[NH:14][C:15](=[O:16])[c:17]1[cH:18][cH:19][cH:20][cH:21... | COC(=O)[C@H](Cc1ccc(OCc2ccccc2)cc1)NC(=O)c1cc(Br)ccc1O | COC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)c1ccccc1O | null | [Pd] | CO | Deprotection | OtherReaction | b1b20b42cb0d6fd067ddc6e11bbcc0911523eab0c979fafe4369acbfdb3a3465 | 64cf28b8f3773c757185e0477276172ed8a5be9160b075bae11336054ecc2128 | O=C(NCCc1ccccc1)c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](-[#7:5])=[O;D1;H0:6]):[c:7]:[c:8].[c:9]:[c:10](-[O;H0;D2;+0:11]-C-c1:c:c:c:c:c:1):[c:12]>>[#7:5]-[C:4](=[O;D1;H0:6])-[c:3]:[c:2]:[cH;D2;+0:1]:[c:7]:[c:8].[OH;D1;+0:11]-[c:10](:[c:9]):[c:12] | 86.5 | [{"value": 86.5, "product": "COC([C@H](CC1=CC=C(C=C1)O)NC(C1=C(C=CC=C1)O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | (S)-3-(4-benzyloxy-phenyl)-2-(5-bromo-2-hydroxy-benzoylamino)-propionic acid methyl ester (750 mg, 1.5 mmol) was dissolved in 30 mL of MeOH, 100 mg of 10% Pd/C added, and the mixture stirred for 2.5 h under 40 psi of H2. The mixture was filtered and solvent evaporated. The resulting residue was dissolved in DCM, washed... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether | Aromatic alcohol | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HBr | [Pd].CO | null | 2.5 | COC(=O)[C@H](Cc1ccc(OCc2ccccc2)cc1)NC(=O)c1cc(Br)ccc1O>[Pd].CO>COC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)c1ccccc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2991820b48824e2fa11ba09428139f6b | COC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)c1ccccc1O.ClCc1ccc(-c2ccccc2)cc1>>COC(=O)[C@H](Cc1ccc(OCc2ccc(-c3ccccc3)cc2)cc1)NC(=O)c1ccccc1OCc1ccc(-c2ccccc2)cc1 | COC([C@H](CC1=CC=C(C=C1)O)NC(C1=C(C=CC=C1)O)=O)=O.C1=CC=C(C=C1)C2=CC=C(C=C2)CCl.C(=O)([O-])[O-].[K+].[K+]>>COC([C@H](CC1=CC=C(C=C1)OCC1=CC=C(C=C1)C1=CC=CC=C1)NC(C1=C(C=CC=C1)OCC1=CC=C(C=C1)C1=CC=CC=C1)=O)=O | [CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([OH:11])[cH:25][cH:26]1)[NH:27][C:28](=[O:29])[c:30]1[cH:31][cH:32][cH:33][cH:34][c:35]1[OH:36].Cl[CH2:12][c:13]1[cH:14][cH:15][c:16](-[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[cH:23][cH:24]1>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][... | COC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)c1ccccc1O.ClCc1ccc(-c2ccccc2)cc1 | COC(=O)[C@H](Cc1ccc(OCc2ccc(-c3ccccc3)cc2)cc1)NC(=O)c1ccccc1OCc1ccc(-c2ccccc2)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 278380532f1978c5f7adb55019f7f960fc4cd1f008ed3b8c94ccb3a2453bcc72 | 48ecde0a4a88c9b68b73d941f841bdf9f3ce2ff14ceddfc880d07f50176b90cb | O=C(NCCc1ccc(OCc2ccc(-c3ccccc3)cc2)cc1)c1ccccc1OCc1ccc(-c2ccccc2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[OH;D1;+0:10]):[c:11].[OH;D1;+0:12]-[c:13](:[c:14]):[c:15]>>[#7:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[O;H0;D2;+0:10]-[C:16]-[c:17]):[c:11].[c:3]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:12]-[c:13](:[c:14]):[c:15]):[c:4] | 13.5 | [{"value": 13.5, "product": "COC([C@H](CC1=CC=C(C=C1)OCC1=CC=C(C=C1)C1=CC=CC=C1)NC(C1=C(C=CC=C1)OCC1=CC=C(C=C1)C1=CC=CC=C1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | (S)-2-[2-(biphenyl4-ylmethoxy)-benzoylamino]-3-[4-(biphenyl-4-ylmethoxy)-phenyl]-propionic acid methyl ester (48 mg) was prepared from (S)-2-(2-hydroxy-benzoylamino)-3-(4-hydroxy-phenyl)-propionic acid methyl ester (175 mg, 0.55 mmol) and 4-biphenylmethyl chloride (240 mg, 1.2 mmol) with K2CO3 (306 mg, 2.2 mmol) as des... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol.Aromatic alcohol | Ether.Ether | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | null | null | null | COC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)c1ccccc1O.ClCc1ccc(-c2ccccc2)cc1>>COC(=O)[C@H](Cc1ccc(OCc2ccc(-c3ccccc3)cc2)cc1)NC(=O)c1ccccc1OCc1ccc(-c2ccccc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d365ed09cedf475a99efb78cc739170f | COC(=O)[C@H](Cc1ccc(OCc2ccc(-c3ccccc3)cc2)cc1)NC(=O)c1ccccc1OCc1ccc(-c2ccccc2)cc1>>O=C(N[C@@H](Cc1ccc(OCc2ccc(-c3ccccc3)cc2)cc1)C(=O)O)c1ccccc1OCc1ccc(-c2ccccc2)cc1 | COC([C@H](CC1=CC=C(C=C1)OCC1=CC=C(C=C1)C1=CC=CC=C1)NC(C1=C(C=CC=C1)OCC1=CC=C(C=C1)C1=CC=CC=C1)=O)=O.[Li+].[OH-].[Li+].[OH-]>>C1(=CC=C(C=C1)COC1=C(C(=O)N[C@H](C(=O)O)CC2=CC=C(C=C2)OCC2=CC=C(C=C2)C2=CC=CC=C2)C=CC=C1)C1=CC=CC=C1 | C[O:28][C:26]([C@@H:4]([NH:3][C:2](=[O:1])[c:29]1[cH:30][cH:31][cH:32][cH:33][c:34]1[O:35][CH2:36][c:37]1[cH:38][cH:39][c:40](-[c:41]2[cH:42][cH:43][cH:44][cH:45][cH:46]2)[cH:47][cH:48]1)[CH2:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][c:15](-[c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[cH:22][cH:23]2... | COC(=O)[C@H](Cc1ccc(OCc2ccc(-c3ccccc3)cc2)cc1)NC(=O)c1ccccc1OCc1ccc(-c2ccccc2)cc1 | O=C(N[C@@H](Cc1ccc(OCc2ccc(-c3ccccc3)cc2)cc1)C(=O)O)c1ccccc1OCc1ccc(-c2ccccc2)cc1 | null | null | C1CCOC1.CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(NCCc1ccc(OCc2ccc(-c3ccccc3)cc2)cc1)c1ccccc1OCc1ccc(-c2ccccc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 59.4 | [{"value": 59.4, "product": "C1(=CC=C(C=C1)COC1=C(C(=O)N[C@H](C(=O)O)CC2=CC=C(C=C2)OCC2=CC=C(C=C2)C2=CC=CC=C2)C=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | (S)-2-[2-(biphenyl-4-ylmethoxy)-benzoylamino]-3-[4-(biphenyl-4-ylmethoxy)-phenyl]-propionic acid methyl ester (50 mg, 0.077 mmol) was dissolved in 5 mL of THF-MeOH (4-1), cooled to 0° C. and 1.1 equiv of 2 N LiOH added. After 30 minutes, 3.2 additional equiv of 2N LiOH was added and the reaction stirred for 30 minutes.... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | C1CCOC1.CO | 0 | 0.5 | COC(=O)[C@H](Cc1ccc(OCc2ccc(-c3ccccc3)cc2)cc1)NC(=O)c1ccccc1OCc1ccc(-c2ccccc2)cc1>C1CCOC1.CO>O=C(N[C@@H](Cc1ccc(OCc2ccc(-c3ccccc3)cc2)cc1)C(=O)O)c1ccccc1OCc1ccc(-c2ccccc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e5d7414a5d9c457a8edcfadd5d7db4b6 | CC(C)(C)c1ccc(CBr)cc1.COC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)OC(C)(C)C>>COC(=O)[C@H](Cc1ccc(OCc2ccc(C(C)(C)C)cc2)cc1)NC(=O)OC(C)(C)C | COC([C@H](CC1=CC=C(C=C1)O)NC(=O)OC(C)(C)C)=O.C(C)(C)(C)C1=CC=C(CBr)C=C1.C(=O)([O-])[O-].[K+].[K+]>>COC([C@H](CC1=CC=C(C=C1)OCC1=CC=C(C=C1)C(C)(C)C)NC(=O)OC(C)(C)C)=O | Br[CH2:12][c:13]1[cH:14][cH:15][c:16]([C:17]([CH3:18])([CH3:19])[CH3:20])[cH:21][cH:22]1.[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([OH:11])[cH:23][cH:24]1)[NH:25][C:26](=[O:27])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32]>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([O:11][CH2:12... | CC(C)(C)c1ccc(CBr)cc1.COC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)OC(C)(C)C | COC(=O)[C@H](Cc1ccc(OCc2ccc(C(C)(C)C)cc2)cc1)NC(=O)OC(C)(C)C | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(COc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | 46.9 | [{"value": 46.9, "product": "COC([C@H](CC1=CC=C(C=C1)OCC1=CC=C(C=C1)C(C)(C)C)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | (S)-2-Tert-butoxycarbonylamino-3-[4-(4-tert-butyl-benzyloxy)-phenyl]-propionic acid methyl ester (290 mg) was prepared from (S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionic acid methyl ester (425 mg, 1.4 mmol) and 4-tert-butylbenzyl bromide (1.6 mmol) with K2CO3 (398 mg, 2.9 mmol) as described in Procedure... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HBr | null | null | null | CC(C)(C)c1ccc(CBr)cc1.COC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)OC(C)(C)C>>COC(=O)[C@H](Cc1ccc(OCc2ccc(C(C)(C)C)cc2)cc1)NC(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ecb8d9f7750b4a1a8f7c582587ef1cf5 | COC(=O)[C@H](Cc1ccc(OCc2ccc(C(C)(C)C)cc2)cc1)NC(=O)OC(C)(C)C>>COC(=O)[C@@H](N)Cc1ccc(OCc2ccc(C(C)(C)C)cc2)cc1 | COC([C@H](CC1=CC=C(C=C1)OCC1=CC=C(C=C1)C(C)(C)C)NC(=O)OC(C)(C)C)=O.Cl>>Cl.COC([C@H](CC1=CC=C(C=C1)OCC1=CC=C(C=C1)C(C)(C)C)N)=O | CC(C)(C)OC(=O)[NH:6][C@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:7][c:8]1[cH:9][cH:10][c:11]([O:12][CH2:13][c:14]2[cH:15][cH:16][c:17]([C:18]([CH3:19])([CH3:20])[CH3:21])[cH:22][cH:23]2)[cH:24][cH:25]1>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]([NH2:6])[CH2:7][c:8]1[cH:9][cH:10][c:11]([O:12][CH2:13][c:14]2[cH:15][cH:16][c:17]([C:18]... | COC(=O)[C@H](Cc1ccc(OCc2ccc(C(C)(C)C)cc2)cc1)NC(=O)OC(C)(C)C | COC(=O)[C@@H](N)Cc1ccc(OCc2ccc(C(C)(C)C)cc2)cc1 | null | null | O1CCOCC1 | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc(COc2ccccc2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#8:6]-[C;D1;H3:7]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4](=[O;D1;H0:5])-[#8:6]-[C;D1;H3:7] | null | [] | null | null | null | null | (S)-2-Tert-butoxycarbonylamino-3-[4-(4-tert-butyl-benzyloxy)-phenyl]-propionic acid methyl ester (290 mg, 0.66 mmol) was treated with 4 mL of 4N HCl in dioxane for 1 h at room temperature. The solvent was evaporated and the remaining solid triturated with diethyl ether to give (S)-2-amino-3-[4-(4-tert-butyl-benzyloxy)-... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ccccc1 | HO- | O1CCOCC1 | null | null | COC(=O)[C@H](Cc1ccc(OCc2ccc(C(C)(C)C)cc2)cc1)NC(=O)OC(C)(C)C>O1CCOCC1>COC(=O)[C@@H](N)Cc1ccc(OCc2ccc(C(C)(C)C)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6e660cb4b004408b8e9d605c0420d374 | COC(=O)[C@@H](N)Cc1ccc(OCc2ccc(C(C)(C)C)cc2)cc1.Nc1ccc(Cl)cc1C(=O)O>>COC(=O)[C@H](Cc1ccc(OCc2ccc(C(C)(C)C)cc2)cc1)NC(=O)c1cc(Cl)ccc1N | Cl.COC([C@H](CC1=CC=C(C=C1)OCC1=CC=C(C=C1)C(C)(C)C)N)=O.NC1=C(C(=O)O)C=C(C=C1)Cl.Cl>>COC([C@H](CC1=CC=C(C=C1)OCC1=CC=C(C=C1)C(C)(C)C)NC(C1=C(C=CC(=C1)Cl)N)=O)=O | [CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([O:11][CH2:12][c:13]2[cH:14][cH:15][c:16]([C:17]([CH3:18])([CH3:19])[CH3:20])[cH:21][cH:22]2)[cH:23][cH:24]1)[NH2:25].O[C:26](=[O:27])[c:28]1[cH:29][c:30]([Cl:31])[cH:32][cH:33][c:34]1[NH2:35]>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][c:... | COC(=O)[C@@H](N)Cc1ccc(OCc2ccc(C(C)(C)C)cc2)cc1.Nc1ccc(Cl)cc1C(=O)O | COC(=O)[C@H](Cc1ccc(OCc2ccc(C(C)(C)C)cc2)cc1)NC(=O)c1cc(Cl)ccc1N | null | null | CCOC(=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCc1ccc(OCc2ccccc2)cc1)c1ccccc1 | 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:9](=[O;D1;H0:10])-[#8:11]-[C;D1;H3:12]>>[C:6]-[C:7](-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:9](=[O;D1;H0:10])-[#8:11]-[C;D1;H3:12] | 62 | [{"value": 62.0, "product": "COC([C@H](CC1=CC=C(C=C1)OCC1=CC=C(C=C1)C(C)(C)C)NC(C1=C(C=CC(=C1)Cl)N)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | (S)-2-(2-Amino-5-chloro-benzoylamino)-3-[4-(4-tert-butyl-benzyloxy)-phenyl]-propionic acid methyl ester (175 mg) was prepared from (S)-2-amino-3-[4-(4-tert-butyl-benzyloxy)-phenyl]-propionic acid methyl ester-hydrochloride (214 mg, 0.57 mmol) and 2-amino-5-chloro-benzoic acid (101 mg) as described in Procedure A, excep... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | CCOC(=O)C | null | null | COC(=O)[C@@H](N)Cc1ccc(OCc2ccc(C(C)(C)C)cc2)cc1.Nc1ccc(Cl)cc1C(=O)O>CCOC(=O)C>COC(=O)[C@H](Cc1ccc(OCc2ccc(C(C)(C)C)cc2)cc1)NC(=O)c1cc(Cl)ccc1N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3bd66c13161a4af8b37653f5d9c3b71b | COC(=O)[C@H](Cc1ccc(Br)cc1)NC(=O)c1cc(Cl)ccc1N.O=Cc1cccc2ccccc12>>COC(=O)[C@H](Cc1ccc(Br)cc1)NC(=O)c1cc(Cl)ccc1NCc1cccc2ccccc12 | COC([C@H](CC1=CC=C(C=C1)Br)NC(C1=C(C=CC(=C1)Cl)N)=O)=O.C1(=CC=CC2=CC=CC=C12)C=O>>COC([C@H](CC1=CC=C(C=C1)Br)NC(C1=C(C=CC(=C1)Cl)NCC1=CC=CC2=CC=CC=C12)=O)=O | [CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]1)[NH:14][C:15](=[O:16])[c:17]1[cH:18][c:19]([Cl:20])[cH:21][cH:22][c:23]1[NH2:24].O=[CH:25][c:26]1[cH:27][cH:28][cH:29][c:30]2[cH:31][cH:32][cH:33][cH:34][c:35]12>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([Br... | COC(=O)[C@H](Cc1ccc(Br)cc1)NC(=O)c1cc(Cl)ccc1N.O=Cc1cccc2ccccc12 | COC(=O)[C@H](Cc1ccc(Br)cc1)NC(=O)c1cc(Cl)ccc1NCc1cccc2ccccc12 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | O=C(NCCc1ccccc1)c1ccccc1NCc1cccc2ccccc12 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[NH2;D1;+0:10]):[c:11]>>[#7:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[NH;D2;+0:10]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:11] | null | [] | null | null | null | null | (S)-3-(4-Bromo-phenyl)-2-{5-chloro-2-[(naphthalen-1-ylmethyl)-amino]-benzoylamino}-propionic acid methyl ester was prepared from (S)-2-(2-amino-5-chloro-benzoylamino)-3-(4-bromo-phenyl)-propionic acid methyl ester (2.5 g, 6.07 mmol) and 1-naphthaldehyde (2.0 g, 13.3 mmol) according to Procedure G, except for the follow... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1ccc2ccccc2c1 | Other | C(Cl)Cl | null | null | COC(=O)[C@H](Cc1ccc(Br)cc1)NC(=O)c1cc(Cl)ccc1N.O=Cc1cccc2ccccc12>C(Cl)Cl>COC(=O)[C@H](Cc1ccc(Br)cc1)NC(=O)c1cc(Cl)ccc1NCc1cccc2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-99513236d4c84c22b8b4e88da40b7cd7 | COC(=O)[C@H](Cc1ccc(Br)cc1)NC(=O)c1cc(Cl)ccc1NCc1cccc2ccccc12.OB(O)c1ccc(Oc2ccccc2)cc1>>O=C(N[C@@H](Cc1ccc(-c2ccc(Oc3ccccc3)cc2)cc1)C(=O)O)c1cc(Cl)ccc1NCc1cccc2ccccc12 | COC([C@H](CC1=CC=C(C=C1)Br)NC(C1=C(C=CC(=C1)Cl)NCC1=CC=CC2=CC=CC=C12)=O)=O.O(C1=CC=CC=C1)C1=CC=C(C=C1)B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>>ClC=1C=CC(=C(C(=O)N[C@H](C(=O)O)CC2=CC=C(C=C2)C2=CC=C(C=C2)OC2=CC=CC=C2)C1)NCC1=CC=CC2=CC=CC=C12 | C[O:27][C:25]([C@@H:4]([NH:3][C:2](=[O:1])[c:28]1[cH:29][c:30]([Cl:31])[cH:32][cH:33][c:34]1[NH:35][CH2:36][c:37]1[cH:38][cH:39][cH:40][c:41]2[cH:42][cH:43][cH:44][cH:45][c:46]12)[CH2:5][c:6]1[cH:7][cH:8][c:9](Br)[cH:23][cH:24]1)=[O:26].OB(O)[c:10]1[cH:11][cH:12][c:13]([O:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)... | COC(=O)[C@H](Cc1ccc(Br)cc1)NC(=O)c1cc(Cl)ccc1NCc1cccc2ccccc12.OB(O)c1ccc(Oc2ccccc2)cc1 | O=C(N[C@@H](Cc1ccc(-c2ccc(Oc3ccccc3)cc2)cc1)C(=O)O)c1cc(Cl)ccc1NCc1cccc2ccccc12 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C1(=CC=CC=C1)C.C(Cl)Cl | C-C Coupling | OtherReaction | 04157bef51d5543c035526858b11d2af2b78e75d38cd85edf56b617e6aebc946 | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | O=C(NCCc1ccc(-c2ccc(Oc3ccccc3)cc2)cc1)c1ccccc1NCc1cccc2ccccc12 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-[O;H0;D2;+0:6]-[C:7](-[C:8])=[O;D1;H0:9].O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[C:8]-[C:7](=[O;D1;H0:9])-[OH;D1;+0:6].[c:12]:[c:11]:[c;H0;D3;+0:10](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:13]:[c:14] | 52.3 | [{"value": 52.3, "product": "ClC=1C=CC(=C(C(=O)N[C@H](C(=O)O)CC2=CC=C(C=C2)C2=CC=C(C=C2)OC2=CC=CC=C2)C1)NCC1=CC=CC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | (S)-3-(4-Bromo-phenyl)-2-{5-chloro-2-[(naphthalen-1-ylmethyl)-amino]-benzoylamino}-propionic acid methyl ester (150 mg, 0.36 mmol), Pd (PPh3)4 (84 mg, 0.072 mmol), and 4-phenoxyphenylboronic acid (233 mg, 1.09 mmol) were dissolved in 5 mL of toluene, a 1M Na2CO3 solution (0.9 mL, 0.91 mmol) added and the mixture heated... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2ccccc2c1 | 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.C1(=CC=CC=C1)C.C(Cl)Cl | 80 | null | COC(=O)[C@H](Cc1ccc(Br)cc1)NC(=O)c1cc(Cl)ccc1NCc1cccc2ccccc12.OB(O)c1ccc(Oc2ccccc2)cc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C.C(Cl)Cl>O=C(N[C@@H](Cc1ccc(-c2ccc(Oc3ccccc3)cc2... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-95f10ea146fa4dd798c4b19d25e814d7 | COC(=O)[C@@H](N)Cc1ccc(Br)cc1.Nc1ccc(Cl)c(C(=O)O)c1>>COC(=O)[C@H](Cc1ccc(Br)cc1)NC(=O)c1cc(N)ccc1Cl | Cl.COC([C@H](CC1=CC=C(C=C1)Br)N)=O.NC=1C=CC(=C(C(=O)O)C1)Cl.Cl>>COC([C@H](CC1=CC=C(C=C1)Br)NC(C1=C(C=CC(=C1)N)Cl)=O)=O | [CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]1)[NH2:14].O[C:15](=[O:16])[c:17]1[cH:18][c:19]([NH2:20])[cH:21][cH:22][c:23]1[Cl:24]>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]1)[NH:14][C:15](=[O:16])[c:17]1[cH:18][c:19]([NH2:20])[cH:2... | COC(=O)[C@@H](N)Cc1ccc(Br)cc1.Nc1ccc(Cl)c(C(=O)O)c1 | COC(=O)[C@H](Cc1ccc(Br)cc1)NC(=O)c1cc(N)ccc1Cl | null | null | CCOC(=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCc1ccccc1)c1ccccc1 | 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:9](=[O;D1;H0:10])-[#8:11]-[C;D1;H3:12]>>[C:6]-[C:7](-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:9](=[O;D1;H0:10])-[#8:11]-[C;D1;H3:12] | 15.1 | [{"value": 15.1, "product": "COC([C@H](CC1=CC=C(C=C1)Br)NC(C1=C(C=CC(=C1)N)Cl)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | (S)-2-(5-Amino-2-chloro-benzoylamino)-3-(4-bromo-phenyl)-propionic acid methyl ester (316 mg) was prepared from (S)-2-Amino-3-(4-bromo-phenyl)-propionic acid methyl ester-hydrochloride (1.5 g, 5.1 mmol) and 5-amino-2-chloro-benzoic acid (909 mg, 5.1 mmol) as described in Procedure A, except for an adapted work-up. Afte... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | CCOC(=O)C | null | null | COC(=O)[C@@H](N)Cc1ccc(Br)cc1.Nc1ccc(Cl)c(C(=O)O)c1>CCOC(=O)C>COC(=O)[C@H](Cc1ccc(Br)cc1)NC(=O)c1cc(N)ccc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-86e11b55b99c44259c73f074def85c89 | COC(=O)[C@H](Cc1ccc(Br)cc1)NC(=O)c1cc(N)ccc1Cl.O=Cc1cccc2ccccc12>>COC(=O)[C@H](Cc1ccc(Br)cc1)NC(=O)c1cc(NCc2cccc3ccccc23)ccc1Cl | C(Cl)Cl.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+].COC([C@H](CC1=CC=C(C=C1)Br)NC(C1=C(C=CC(=C1)N)Cl)=O)=O.C1(=CC=CC2=CC=CC=C12)C=O>>COC([C@H](CC1=CC=C(C=C1)Br)NC(C1=C(C=CC(=C1)NCC1=CC=CC2=CC=CC=C12)Cl)=O)=O | [CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]1)[NH:14][C:15](=[O:16])[c:17]1[cH:18][c:19]([NH2:20])[cH:32][cH:33][c:34]1[Cl:35].O=[CH:21][c:22]1[cH:23][cH:24][cH:25][c:26]2[cH:27][cH:28][cH:29][cH:30][c:31]12>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([Br... | COC(=O)[C@H](Cc1ccc(Br)cc1)NC(=O)c1cc(N)ccc1Cl.O=Cc1cccc2ccccc12 | COC(=O)[C@H](Cc1ccc(Br)cc1)NC(=O)c1cc(NCc2cccc3ccccc23)ccc1Cl | null | null | ClCCCl.C1CCOC1 | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | O=C(NCCc1ccccc1)c1cccc(NCc2cccc3ccccc23)c1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[NH;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8] | 62.1 | [{"value": 62.1, "product": "COC([C@H](CC1=CC=C(C=C1)Br)NC(C1=C(C=CC(=C1)NCC1=CC=CC2=CC=CC=C12)Cl)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | (S)-3-(4-Bromo-phenyl)-2-{2-chloro-5-[(naphthalen-1-ylmethyl)-amino]-benzoylamino}-propionic acid methyl ester (264 mg) was prepared from (S)-2-(5-amino-2-chloro-benzoylamino)-3-(4-bromo-phenyl)-propionic acid methyl ester (316 mg, 0.77 mmol) and 1-naphthaldehyde (0.231 mL, 1.7 mmol) according to Procedure G, except fo... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1ccc2ccccc2c1 | Other | ClCCCl.C1CCOC1 | null | null | COC(=O)[C@H](Cc1ccc(Br)cc1)NC(=O)c1cc(N)ccc1Cl.O=Cc1cccc2ccccc12>ClCCCl.C1CCOC1>COC(=O)[C@H](Cc1ccc(Br)cc1)NC(=O)c1cc(NCc2cccc3ccccc23)ccc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-23962f4af22d4674b91c857de759d1cc | COC(=O)[C@@H](N)Cc1ccc(Br)cc1.Nc1ccc(C(=O)O)cc1>>COC(=O)[C@H](Cc1ccc(Br)cc1)NC(=O)c1ccc(N)cc1 | Cl.COC([C@H](CC1=CC=C(C=C1)Br)N)=O.NC1=CC=C(C(=O)O)C=C1.Cl>>COC([C@H](CC1=CC=C(C=C1)Br)NC(C1=CC=C(C=C1)N)=O)=O | [CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]1)[NH2:14].O[C:15](=[O:16])[c:17]1[cH:18][cH:19][c:20]([NH2:21])[cH:22][cH:23]1>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]1)[NH:14][C:15](=[O:16])[c:17]1[cH:18][cH:19][c:20]([NH2:21])[cH:... | COC(=O)[C@@H](N)Cc1ccc(Br)cc1.Nc1ccc(C(=O)O)cc1 | COC(=O)[C@H](Cc1ccc(Br)cc1)NC(=O)c1ccc(N)cc1 | null | null | CCOC(=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCc1ccccc1)c1ccccc1 | 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:9](=[O;D1;H0:10])-[#8:11]-[C;D1;H3:12]>>[C:6]-[C:7](-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:9](=[O;D1;H0:10])-[#8:11]-[C;D1;H3:12] | 21.6 | [{"value": 21.6, "product": "COC([C@H](CC1=CC=C(C=C1)Br)NC(C1=CC=C(C=C1)N)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | (S)-2-(4-Amino-benzoylamino)-3-(4-bromo-phenyl)-propionic acid methyl ester (415 mg) was prepared from (S)-2-amino-3-(4-bromo-phenyl)-propionic acid methyl ester-hydrochloride (1.5 g, 5.1 mmol) and 4-amino-benzoic acid (698 mg, 5.1 mmol) as described in Procedure A, except for an adapted work-up. After reaction complet... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | CCOC(=O)C | null | null | COC(=O)[C@@H](N)Cc1ccc(Br)cc1.Nc1ccc(C(=O)O)cc1>CCOC(=O)C>COC(=O)[C@H](Cc1ccc(Br)cc1)NC(=O)c1ccc(N)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e2ac4afce6ba4e8f952e9cac82745271 | COC(=O)[C@H](Cc1ccc(Br)cc1)NC(=O)c1ccc(N)cc1.O=Cc1cccc2ccccc12>>COC(=O)[C@H](Cc1ccc(Br)cc1)NC(=O)c1ccc(NCc2cccc3ccccc23)cc1 | [BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+].COC([C@H](CC1=CC=C(C=C1)Br)NC(C1=CC=C(C=C1)N)=O)=O.C1(=CC=CC2=CC=CC=C12)C=O.C(Cl)Cl>>COC([C@H](CC1=CC=C(C=C1)Br)NC(C1=CC=C(C=C1)NCC1=CC=CC2=CC=CC=C12)=O)=O | [CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]1)[NH:14][C:15](=[O:16])[c:17]1[cH:18][cH:19][c:20]([NH2:21])[cH:33][cH:34]1.O=[CH:22][c:23]1[cH:24][cH:25][cH:26][c:27]2[cH:28][cH:29][cH:30][cH:31][c:32]12>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([Br:11])[... | COC(=O)[C@H](Cc1ccc(Br)cc1)NC(=O)c1ccc(N)cc1.O=Cc1cccc2ccccc12 | COC(=O)[C@H](Cc1ccc(Br)cc1)NC(=O)c1ccc(NCc2cccc3ccccc23)cc1 | null | null | ClCCCl.C1CCOC1 | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | O=C(NCCc1ccccc1)c1ccc(NCc2cccc3ccccc23)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[NH;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8] | 48 | [{"value": 48.0, "product": "COC([C@H](CC1=CC=C(C=C1)Br)NC(C1=CC=C(C=C1)NCC1=CC=CC2=CC=CC=C12)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | (S)-3-(4-Bromo-phenyl)-2-{4-[(naphthalen-1-ylmethyl)-amino]-benzoylamino}-propionic acid methyl ester (273 mg) was prepared from (S)-2-(4-amino-benzoylamino)-3-(4-bromo-phenyl)-propionic acid methyl ester (415 mg, 1.1 mmol) and 1-naphthaldehyde (0.331 mL, 2.4 mmol) according to Procedure G, except for the following: th... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1ccc2ccccc2c1 | Other | ClCCCl.C1CCOC1 | null | null | COC(=O)[C@H](Cc1ccc(Br)cc1)NC(=O)c1ccc(N)cc1.O=Cc1cccc2ccccc12>ClCCCl.C1CCOC1>COC(=O)[C@H](Cc1ccc(Br)cc1)NC(=O)c1ccc(NCc2cccc3ccccc23)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ec6e09a7ec42436d89a4275b9ece9d8d | COC(=O)[C@H](Cc1ccc(Br)cc1)NC(=O)c1ccc(NCc2cccc3ccccc23)cc1.OB(O)c1ccc(Oc2ccccc2)cc1>>COC(=O)[C@H](Cc1ccc(-c2ccc(Oc3ccccc3)cc2)cc1)NC(=O)c1ccc(NCc2cccc3ccccc23)cc1 | COC([C@H](CC1=CC=C(C=C1)Br)NC(C1=CC=C(C=C1)NCC1=CC=CC2=CC=CC=C12)=O)=O.O(C1=CC=CC=C1)C1=CC=C(C=C1)B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>>COC([C@H](CC1=CC=C(C=C1)C1=CC=C(C=C1)OC1=CC=CC=C1)NC(C1=CC=C(C=C1)NCC1=CC=CC2=CC=CC=C12)=O)=O | Br[c:10]1[cH:9][cH:8][c:7]([CH2:6][C@@H:5]([C:3]([O:2][CH3:1])=[O:4])[NH:26][C:27](=[O:28])[c:29]2[cH:30][cH:31][c:32]([NH:33][CH2:34][c:35]3[cH:36][cH:37][cH:38][c:39]4[cH:40][cH:41][cH:42][cH:43][c:44]34)[cH:45][cH:46]2)[cH:25][cH:24]1.OB(O)[c:11]1[cH:12][cH:13][c:14]([O:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2... | COC(=O)[C@H](Cc1ccc(Br)cc1)NC(=O)c1ccc(NCc2cccc3ccccc23)cc1.OB(O)c1ccc(Oc2ccccc2)cc1 | COC(=O)[C@H](Cc1ccc(-c2ccc(Oc3ccccc3)cc2)cc1)NC(=O)c1ccc(NCc2cccc3ccccc23)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 | C1(=CC=CC=C1)C | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(NCCc1ccc(-c2ccc(Oc3ccccc3)cc2)cc1)c1ccc(NCc2cccc3ccccc23)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:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9]:[c:10] | 33.3 | [{"value": 33.3, "product": "COC([C@H](CC1=CC=C(C=C1)C1=CC=C(C=C1)OC1=CC=CC=C1)NC(C1=CC=C(C=C1)NCC1=CC=CC2=CC=CC=C12)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | (S)-3-(4-Bromo-phenyl)-2-{4-[(naphthalen-1-ylmethyl)-amino]-benzoylamino}-propionic acid methyl ester (273 mg, 0.53 mmol), Pd (PPh3)4 (96 mg, 0.11 mmol), and 4-phenoxyphenylboronic acid (226 mg, 1.1 mmol) were dissolved in 5 mL of toluene, a 1M Na2CO3 solution (1.3 mL, 1.3 mmol) added and the mixture heated at 80° C. f... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2ccccc2c1 | 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.C1(=CC=CC=C1)C | 80 | null | COC(=O)[C@H](Cc1ccc(Br)cc1)NC(=O)c1ccc(NCc2cccc3ccccc23)cc1.OB(O)c1ccc(Oc2ccccc2)cc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C>COC(=O)[C@H](Cc1ccc(-c2ccc(Oc3ccccc3)cc2)cc1)NC(=... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a838c7ab372f470eb621f8cafa8982f4 | COC(=O)[C@@H](N)Cc1ccc(-c2ccc(Oc3ccccc3)cc2)cc1.Nc1ccc(Cl)cc1C(=O)O>>COC(=O)[C@H](Cc1ccc(-c2ccc(Oc3ccccc3)cc2)cc1)NC(=O)c1cc(Cl)ccc1N | CN(C)C(=[N+](C)C)ON1C2=C(C=CC=C2)N=N1.F[P-](F)(F)(F)(F)F.NC1=C(C(=O)O)C=C(C=C1)Cl.CCN(C(C)C)C(C)C.COC([C@H](CC1=CC=C(C=C1)C1=CC=C(C=C1)OC1=CC=CC=C1)N)=O>>COC([C@H](CC1=CC=C(C=C1)C1=CC=C(C=C1)OC1=CC=CC=C1)NC(C1=C(C=CC(=C1)Cl)N)=O)=O | [CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][c:10](-[c:11]2[cH:12][cH:13][c:14]([O:15][c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[cH:22][cH:23]2)[cH:24][cH:25]1)[NH2:26].O[C:27](=[O:28])[c:29]1[cH:30][c:31]([Cl:32])[cH:33][cH:34][c:35]1[NH2:36]>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][... | COC(=O)[C@@H](N)Cc1ccc(-c2ccc(Oc3ccccc3)cc2)cc1.Nc1ccc(Cl)cc1C(=O)O | COC(=O)[C@H](Cc1ccc(-c2ccc(Oc3ccccc3)cc2)cc1)NC(=O)c1cc(Cl)ccc1N | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCc1ccc(-c2ccc(Oc3ccccc3)cc2)cc1)c1ccccc1 | 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:9](=[O;D1;H0:10])-[#8:11]-[C;D1;H3:12]>>[C:6]-[C:7](-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:9](=[O;D1;H0:10])-[#8:11]-[C;D1;H3:12] | 92.7 | [{"value": 92.7, "product": null, "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | (S)-2-(2-amino-5-chloro-benzoylamino)-3-(4′-phenoxy-biphenyl-4-yl)-propionic acid methyl ester was prepared following Procedure A using 2-amino-5-chloro-benzoic acid (1.23 g, 7 mmol), (S)-2-amino-3-(4′-phenoxy-biphenyl-4-yl)propionic acid methyl ester (2.43 g, 7 mmol), HBTU (3.19 g, 8.4 mmol) and DIEA (2.46 mL, 14 mmol... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | CN(C)C=O | null | null | COC(=O)[C@@H](N)Cc1ccc(-c2ccc(Oc3ccccc3)cc2)cc1.Nc1ccc(Cl)cc1C(=O)O>CN(C)C=O>COC(=O)[C@H](Cc1ccc(-c2ccc(Oc3ccccc3)cc2)cc1)NC(=O)c1cc(Cl)ccc1N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d32bbcb522a34146bf012ecb64b58430 | COC(=O)CCCCC=O.COC(=O)[C@H](Cc1ccc(-c2ccc(Oc3ccccc3)cc2)cc1)NC(=O)c1cc(Cl)ccc1N>>COC(=O)CCCCCNc1ccc(Cl)cc1C(=O)N[C@@H](Cc1ccc(-c2ccc(Oc3ccccc3)cc2)cc1)C(=O)OC | C(C)(=O)O.COC([C@H](CC1=CC=C(C=C1)C1=CC=C(C=C1)OC1=CC=CC=C1)NC(C1=C(C=CC(=C1)Cl)N)=O)=O.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+].COC(CCCCC=O)=O>>COC(CCCCCNC1=C(C=C(C=C1)Cl)C(N[C@@H](CC1=CC=C(C=C1)C1=CC=C(C=C1)OC1=CC=CC=C1)C(=O)OC)=O)=O | O=[CH:9][CH2:8][CH2:7][CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4].[NH2:10][c:11]1[cH:12][cH:13][c:14]([Cl:15])[cH:16][c:17]1[C:18](=[O:19])[NH:20][C@@H:21]([CH2:22][c:23]1[cH:24][cH:25][c:26](-[c:27]2[cH:28][cH:29][c:30]([O:31][c:32]3[cH:33][cH:34][cH:35][cH:36][cH:37]3)[cH:38][cH:39]2)[cH:40][cH:41]1)[C:42](=[O:43])[O:44]... | COC(=O)CCCCC=O.COC(=O)[C@H](Cc1ccc(-c2ccc(Oc3ccccc3)cc2)cc1)NC(=O)c1cc(Cl)ccc1N | COC(=O)CCCCCNc1ccc(Cl)cc1C(=O)N[C@@H](Cc1ccc(-c2ccc(Oc3ccccc3)cc2)cc1)C(=O)OC | null | null | ClCCCl | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | O=C(NCCc1ccc(-c2ccc(Oc3ccccc3)cc2)cc1)c1ccccc1 | O=[CH;D2;+0:1]-[C:2]-[C:3].[#7:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[NH2;D1;+0:9]):[c:10]>>[#7:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[NH;D2;+0:9]-[CH2;D2;+0:1]-[C:2]-[C:3]):[c:10] | null | [] | null | null | null | null | (S)-6-{4-Chloro-2-[1-methoxycarbonyl-2-(4′-phenoxy-biphenyl-4-yl)-ethylcarbamoyl]-phenylamino}-hexanoic acid methyl ester was prepared following Procedure G using (S)-2-(2-amino-5-chloro-benzoylamino)-3-(4′-phenoxy-biphenyl-4-yl)propionic acid methyl ester (401 mg, 0.8 mmol), 6-oxo-hexanoic acid methyl ester (231 mg, 1... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | ClCCCl | null | null | COC(=O)CCCCC=O.COC(=O)[C@H](Cc1ccc(-c2ccc(Oc3ccccc3)cc2)cc1)NC(=O)c1cc(Cl)ccc1N>ClCCCl>COC(=O)CCCCCNc1ccc(Cl)cc1C(=O)N[C@@H](Cc1ccc(-c2ccc(Oc3ccccc3)cc2)cc1)C(=O)OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b130170f2b6845db8a0421cbc4f1be3d | CN(C)c1cccc2c(S(=O)(=O)Cl)cccc12.COC(=O)[C@H](Cc1ccc(-c2ccccc2Oc2ccccc2)cc1)NC(=O)c1cc(Cl)ccc1N>>COC(=O)[C@H](Cc1ccc(-c2ccccc2Oc2ccccc2)cc1)NC(=O)c1cc(Cl)ccc1NS(=O)(=O)c1cccc2c(N(C)C)cccc12 | COC([C@H](CC1=CC=C(C=C1)C1=C(C=CC=C1)OC1=CC=CC=C1)NC(C1=C(C=CC(=C1)Cl)N)=O)=O.N1=CC=CC=C1.CN(C1=C2C=CC=C(C2=CC=C1)S(=O)(=O)Cl)C>>COC([C@H](CC1=CC=C(C=C1)C1=C(C=CC=C1)OC1=CC=CC=C1)NC(C1=C(C=CC(=C1)Cl)NS(=O)(=O)C1=CC=CC2=C(C=CC=C12)N(C)C)=O)=O | Cl[S:37](=[O:38])(=[O:39])[c:40]1[cH:41][cH:42][cH:43][c:44]2[c:45]([N:46]([CH3:47])[CH3:48])[cH:49][cH:50][cH:51][c:52]12.[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[O:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[cH:24][cH:25]1)[NH:26][C:27](=[O:28])[... | CN(C)c1cccc2c(S(=O)(=O)Cl)cccc12.COC(=O)[C@H](Cc1ccc(-c2ccccc2Oc2ccccc2)cc1)NC(=O)c1cc(Cl)ccc1N | COC(=O)[C@H](Cc1ccc(-c2ccccc2Oc2ccccc2)cc1)NC(=O)c1cc(Cl)ccc1NS(=O)(=O)c1cccc2c(N(C)C)cccc12 | null | null | C(Cl)Cl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C(NCCc1ccc(-c2ccccc2Oc2ccccc2)cc1)c1ccccc1NS(=O)(=O)c1cccc2ccccc12 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[#7:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#7:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[NH;D2;+0:12]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]):[c:13] | 68.1 | [{"value": 68.1, "product": "COC([C@H](CC1=CC=C(C=C1)C1=C(C=CC=C1)OC1=CC=CC=C1)NC(C1=C(C=CC(=C1)Cl)NS(=O)(=O)C1=CC=CC2=C(C=CC=C12)N(C)C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a stirring solution of (S)-2(2-amino-5-chloro-benzoylamino)-3-(2′-phenoxy-biphenyl-4-yl)propionic acid methyl ester (100 mg, 0.2 mmol) prepared above dissolved in DCM containing pyridine (31.6 mg, 0.4 mmol), was added 5-Dimethylamino-naphthalene-1-sulfonyl chloride (59.1 mg, 0.0.22 mmol) at 0° C. The reaction mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2ccccc2c1 | HCl | C(Cl)Cl | null | 3 | CN(C)c1cccc2c(S(=O)(=O)Cl)cccc12.COC(=O)[C@H](Cc1ccc(-c2ccccc2Oc2ccccc2)cc1)NC(=O)c1cc(Cl)ccc1N>C(Cl)Cl>COC(=O)[C@H](Cc1ccc(-c2ccccc2Oc2ccccc2)cc1)NC(=O)c1cc(Cl)ccc1NS(=O)(=O)c1cccc2c(N(C)C)cccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3caad9211a7240708ab6639c302eda31 | CCC(C)C=O.Nc1ccc(Cl)cc1C(=O)O>>CCC(C)CNc1ccc(Cl)cc1C(=O)O | NC1=C(C(=O)O)C=C(C=C1)Cl.CC(C=O)CC.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>ClC=1C=CC(=C(C(=O)O)C1)NCC(CC)C | O=[CH:5][CH:3]([CH2:2][CH3:1])[CH3:4].[NH2:6][c:7]1[cH:8][cH:9][c:10]([Cl:11])[cH:12][c:13]1[C:14](=[O:15])[OH:16]>>[CH3:1][CH2:2][CH:3]([CH3:4])[CH2:5][NH:6][c:7]1[cH:8][cH:9][c:10]([Cl:11])[cH:12][c:13]1[C:14](=[O:15])[OH:16] | CCC(C)C=O.Nc1ccc(Cl)cc1C(=O)O | CCC(C)CNc1ccc(Cl)cc1C(=O)O | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccccc1 | O=[CH;D2;+0:1]-[C:2](-[C:3])-[C;D1;H3:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]-[C:9](=[O;D1;H0:10])-[O;D1;H1:11]>>[C:3]-[C:2](-[C;D1;H3:4])-[CH2;D2;+0:1]-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8]-[C:9](=[O;D1;H0:10])-[O;D1;H1:11] | null | [] | null | null | null | null | 5-chloro-2-(2-methyl-butylamino)-benzoic acid was prepared from 2-amino-5-chloro-benzoic acid (23.31 mmol, 4.0 g) and 2-methylbutyraldehyde (23.31 mmol, 2.0 g) with sodium triacetoxyborohydride (96.62 mmol, 9.88 g) as per Procedure G (5.0 g).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1 | Other | null | null | null | CCC(C)C=O.Nc1ccc(Cl)cc1C(=O)O>>CCC(C)CNc1ccc(Cl)cc1C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2c39351245f74f4aae94dd654876cde5 | CCC(C)CNc1ccc(Cl)cc1C(=O)O.COC(=O)[C@@H](N)Cc1ccc(Br)cc1>>CCC(C)CNc1ccc(Cl)cc1C(=O)N[C@@H](Cc1ccc(Br)cc1)C(=O)OC | ClC=1C=CC(=C(C(=O)O)C1)NCC(CC)C.Cl.COC([C@H](CC1=CC=C(C=C1)Br)N)=O.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=C2)N=N1.F[P-](F)(F)(F)(F)F.C(C)(C)N(CC)C(C)C>>COC([C@H](CC1=CC=C(C=C1)Br)NC(C1=C(C=CC(=C1)Cl)NCC(CC)C)=O)=O | O[C:14]([c:13]1[c:7]([NH:6][CH2:5][CH:3]([CH2:2][CH3:1])[CH3:4])[cH:8][cH:9][c:10]([Cl:11])[cH:12]1)=[O:15].[NH2:16][C@@H:17]([CH2:18][c:19]1[cH:20][cH:21][c:22]([Br:23])[cH:24][cH:25]1)[C:26](=[O:27])[O:28][CH3:29]>>[CH3:1][CH2:2][CH:3]([CH3:4])[CH2:5][NH:6][c:7]1[cH:8][cH:9][c:10]([Cl:11])[cH:12][c:13]1[C:14](=[O:15]... | CCC(C)CNc1ccc(Cl)cc1C(=O)O.COC(=O)[C@@H](N)Cc1ccc(Br)cc1 | CCC(C)CNc1ccc(Cl)cc1C(=O)N[C@@H](Cc1ccc(Br)cc1)C(=O)OC | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCc1ccccc1)c1ccccc1 | 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:9](=[O;D1;H0:10])-[#8:11]-[C;D1;H3:12]>>[C:6]-[C:7](-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:9](=[O;D1;H0:10])-[#8:11]-[C;D1;H3:12] | 75 | [{"value": 75.0, "product": "COC([C@H](CC1=CC=C(C=C1)Br)NC(C1=C(C=CC(=C1)Cl)NCC(CC)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As per Procedure A, 5-chloro-2-(2-methyl-butylamino)-benzoic acid (12.44 mmol, 3 g) was treated with (2S)-amino-3-(4-bromo-phenyl)-propionic acid methyl ester hydrochloride (12.44 mmol, 3.66 g), HBTU (14.92 mmol, 5.66 g) and diisopropylethylamine (37.32 mmol, 4.82 g) to yield 3-(4-bromo-phenyl)-(2S)-[5-chloro-2-(2-meth... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | CCC(C)CNc1ccc(Cl)cc1C(=O)O.COC(=O)[C@@H](N)Cc1ccc(Br)cc1>>CCC(C)CNc1ccc(Cl)cc1C(=O)N[C@@H](Cc1ccc(Br)cc1)C(=O)OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d0936e14042a432d8d096e61ad02b1e7 | CCC(C)CNc1ccc(Cl)cc1C(=O)N[C@@H](Cc1ccc(Br)cc1)C(=O)OC.OB(O)c1ccccc1OCc1ccccc1>>CCC(C)CNc1ccc(Cl)cc1C(=O)N[C@@H](Cc1ccc(-c2ccccc2OCc2ccccc2)cc1)C(=O)O | C(=O)([O-])[O-].[Na+].[Na+].COC([C@H](CC1=CC=C(C=C1)Br)NC(C1=C(C=CC(=C1)Cl)NCC(CC)C)=O)=O.C(C1=CC=CC=C1)OC1=C(C=CC=C1)B(O)O.COC(C(CC1=CC=C(C=C1)C1=C(C=CC=C1)OCC1=CC=CC=C1)NC(C1=C(C=CC(=C1)Cl)NCC(CC)C)=O)=O>>C(C1=CC=CC=C1)OC1=C(C=CC=C1)C1=CC=C(C=C1)C[C@@H](C(=O)O)NC(C1=C(C=CC(=C1)Cl)NCC(CC)C)=O | C[O:41][C:39]([C@@H:17]([NH:16][C:14]([c:13]1[c:7]([NH:6][CH2:5][CH:3]([CH2:2][CH3:1])[CH3:4])[cH:8][cH:9][c:10]([Cl:11])[cH:12]1)=[O:15])[CH2:18][c:19]1[cH:20][cH:21][c:22](Br)[cH:37][cH:38]1)=[O:40].OB(O)[c:23]1[cH:24][cH:25][cH:26][cH:27][c:28]1[O:29][CH2:30][c:31]1[cH:32][cH:33][cH:34][cH:35][cH:36]1>>[CH3:1][CH2:2... | CCC(C)CNc1ccc(Cl)cc1C(=O)N[C@@H](Cc1ccc(Br)cc1)C(=O)OC.OB(O)c1ccccc1OCc1ccccc1 | CCC(C)CNc1ccc(Cl)cc1C(=O)N[C@@H](Cc1ccc(-c2ccccc2OCc2ccccc2)cc1)C(=O)O | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | C-C Coupling | OtherReaction | 04157bef51d5543c035526858b11d2af2b78e75d38cd85edf56b617e6aebc946 | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | O=C(NCCc1ccc(-c2ccccc2OCc2ccccc2)cc1)c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-[O;H0;D2;+0:6]-[C:7](-[C:8])=[O;D1;H0:9].O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13](-[#8:14]):[c:15]>>[#8:14]-[c:13](:[c:15]):[c;H0;D3;+0:10](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:11]:[c:12].[C:8]-[C:7](=[O;D1;H0:9])-[OH;D1;+0:6] | 95.3 | [{"value": 95.3, "product": "C(C1=CC=CC=C1)OC1=C(C=CC=C1)C1=CC=C(C=C1)C[C@@H](C(=O)O)NC(C1=C(C=CC(=C1)Cl)NCC(CC)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The methyl ester of the title compound was prepared by coupling of the 3-(4-bromo-phenyl)-(2S)-[5-chloro-2-(2-methyl-butylamino)-benzoylamino]-propionic acid methyl ester (1.24 mmol, 0.600 g) and 2-benzyloxyphenyl boronic acid (2.48 mmol, 0.567 g) with Pd (PPh3)4 (0.124 mmol, 0.143 g) as catalyst and Na2CO3 (3.732 mmol... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.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 | null | null | CCC(C)CNc1ccc(Cl)cc1C(=O)N[C@@H](Cc1ccc(Br)cc1)C(=O)OC.OB(O)c1ccccc1OCc1ccccc1>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>CCC(C)CNc1ccc(Cl)cc1C(=O)N[C@@H](Cc1ccc(-c2ccccc2OCc2ccccc2)cc1)C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a422ca6c7e6c47689f57d8e9e9a95543 | Cc1ccc([N+](=O)[O-])c(F)c1.[O]=[Mn](=[O])(=[O])[O-]>>O=C(O)c1ccc([N+](=O)[O-])c(F)c1 | FC=1C=C(C=CC1[N+](=O)[O-])C.[Mn](=O)(=O)(=O)[O-].[K+].O>>FC=1C=C(C(=O)O)C=CC1[N+](=O)[O-] | [CH3:2][c:4]1[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[c:11]([F:12])[cH:13]1.[O]=[Mn](=[O])(=[O:1])[O-:3]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[c:11]([F:12])[cH:13]1 | Cc1ccc([N+](=O)[O-])c(F)c1.[O]=[Mn](=[O])(=[O])[O-] | O=C(O)c1ccc([N+](=O)[O-])c(F)c1 | null | null | null | Acylation | OtherReaction | 7769a4cd09a67e270ac2d1d32df6b7a59b468ff590f9c59723b72ba3c8deb342 | 903e48d04e4504a4fe6977f5e5582144adff237d0488a4542a1907161cf0134c | c1ccccc1 | [CH3;D1;+0:1]-[c:2](:[c:3]):[c:4].[O-;H0;D1:5]-[Mn](=[O;H0;D1;+0:6])(=[O])=[O]>>[O;H0;D1;+0:6]=[C;H0;D3;+0:1](-[OH;D1;+0:5])-[c:2](:[c:3]):[c:4] | 58 | [{"value": 58.0, "product": "FC=1C=C(C(=O)O)C=CC1[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-fluoro-4-nitrotoluene (10 g, 1 eq) and potassium permanganate (25.5 g, 2.5 eq) in water (1 L) is heated under reflux for 6 hours then cooled down to ambient temperature. The mixture is filtered on celite and the aqueous phase is washed twice with diethyl ether (2×300 ml). The aqueous phase is acidified, ... | 10.6084/m9.figshare.5104873.v1 | null | null | Carboxylic acid | null | null | c1ccccc1 | HO- | null | null | null | Cc1ccc([N+](=O)[O-])c(F)c1.[O]=[Mn](=[O])(=[O])[O-]>>O=C(O)c1ccc([N+](=O)[O-])c(F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-deb9f052a4ef441e844061d7b1220537 | CC(C)CCNCCC(C)C.O=C(O)c1ccc([N+](=O)[O-])c(F)c1>>CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(F)c1 | C(CC(C)C)NCCC(C)C.Cl.CN(CCCN=C=NCC)C.ON1N=NC2=C1C=CC=C2.FC=1C=C(C(=O)O)C=CC1[N+](=O)[O-]>>FC=1C=C(C(=O)N(CCC(C)C)CCC(C)C)C=CC1[N+](=O)[O-] | [CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][NH:6][CH2:7][CH2:8][CH:9]([CH3:10])[CH3:11].O[C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[c:21]([F:22])[cH:23]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][N:6]([CH2:7][CH2:8][CH:9]([CH3:10])[CH3:11])[C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20]... | CC(C)CCNCCC(C)C.O=C(O)c1ccc([N+](=O)[O-])c(F)c1 | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(F)c1 | null | null | C(Cl)(Cl)Cl.C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[C:9]-[C:10])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 65 | [{"value": 65.0, "product": "FC=1C=C(C(=O)N(CCC(C)C)CCC(C)C)C=CC1[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 1 | HOUR | 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (4.4 g, 1.1 eq) in solution in chloroform (25 ml) and 1-hydroxybenzotriazole (HOBt) (3.05 g, 1.1 eq) in solution in THF (40 ml) are added successively to 3-fluoro-4-nitrobenzoic acid (3.8 g, 1 eq) in solution in anhydrous THF (30 ml). The mixture is stir... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccccc1 | HO- | C(Cl)(Cl)Cl.C1CCOC1 | 20 | 1 | CC(C)CCNCCC(C)C.O=C(O)c1ccc([N+](=O)[O-])c(F)c1>C(Cl)(Cl)Cl.C1CCOC1>CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-09f7d3f1aee54d4cb0ccc3329cffd28b | CC(C)(C)OC(=O)NCCCN.CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(F)c1>>CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(NCCCNC(=O)OC(C)(C)C)c1 | FC=1C=C(C(=O)N(CCC(C)C)CCC(C)C)C=CC1[N+](=O)[O-].C(=O)(OC(C)(C)C)NCCCN.C([O-])([O-])=O.[K+].[K+]>>CC(CCN(C(=O)C=1C=CC(=C(C1)NCCCNC(OC(C)(C)C)=O)[N+](=O)[O-])CCC(C)C)C | [NH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33].F[c:21]1[c:17]([N+:18](=[O:19])[O-:20])[cH:16][cH:15][c:14]([C:12]([N:6]([CH2:5][CH2:4][CH:2]([CH3:1])[CH3:3])[CH2:7][CH2:8][CH:9]([CH3:10])[CH3:11])=[O:13])[cH:34]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][N:6]([CH2:7][CH2:8][C... | CC(C)(C)OC(=O)NCCCN.CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(F)c1 | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(NCCCNC(=O)OC(C)(C)C)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](-[#7:5])=[O;D1;H0:6]):[c:7](-[#7;+:8]):[c:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[#7:5]-[C:4](=[O;D1;H0:6])-[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:12]-[C:11]-[C:10]):[c:7](-[#7;+:8]):[c:9] | 96 | [{"value": 96.0, "product": "CC(CCN(C(=O)C=1C=CC(=C(C1)NCCCNC(OC(C)(C)C)=O)[N+](=O)[O-])CCC(C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-fluoro-N,N-bis(3-methylbutyl)-4-nitrobenzamide (1.6 g, 1 eq), N-Boc-1,3-diaminopropane (0.9 g, 1.2 eq) and potassium carbonate (1.35 g, 2 eq) in acetonitrile (80 ml) is heated under reflux for 5 hours then concentrated under reduced pressure at 40° C. The residue is taken up in dichloromethane (100 ml) a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | C(C)#N | null | null | CC(C)(C)OC(=O)NCCCN.CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(F)c1>C(C)#N>CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(NCCCNC(=O)OC(C)(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-510cdf6f60cd4e7a9602914299f33781 | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(NCCCNC(=O)OC(C)(C)C)c1>>CC(C)CCN(CCC(C)C)C(=O)c1ccc(N)c(NCCCNC(=O)OC(C)(C)C)c1 | CC(CCN(C(=O)C=1C=CC(=C(C1)NCCCNC(OC(C)(C)C)=O)[N+](=O)[O-])CCC(C)C)C>>NC1=C(C=C(C=C1)C(=O)N(CCC(C)C)CCC(C)C)NCCCNC(OC(C)(C)C)=O | O=[N+:18]([O-])[c:17]1[cH:16][cH:15][c:14]([C:12]([N:6]([CH2:5][CH2:4][CH:2]([CH3:1])[CH3:3])[CH2:7][CH2:8][CH:9]([CH3:10])[CH3:11])=[O:13])[cH:32][c:19]1[NH:20][CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31]>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][N:6]([CH2:7][CH2:8][CH:9]([CH3:10]... | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(NCCCNC(=O)OC(C)(C)C)c1 | CC(C)CCN(CCC(C)C)C(=O)c1ccc(N)c(NCCCNC(=O)OC(C)(C)C)c1 | null | [Pd] | C(C)(=O)OCC.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] | 89 | [{"value": 89.0, "product": "NC1=C(C=C(C=C1)C(=O)N(CCC(C)C)CCC(C)C)NCCCNC(OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 3 | HOUR | Tert-butyl 3-[(5-{[bis (3-methylbutyl)amino]carbonyl}-2-nitrophenyl)amino]propylcarbamate (1.65 g) in solution in a mixture of ethyl acetate/ethanol 2:1 (130 ml), and 10% palladium on carbon (165 mg) are introduced into an autoclave. After stirring for 3 hours under a hydrogen atmosphere (3 bar) at a temperature of app... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Pd].C(C)(=O)OCC.C(C)O | 20 | 3 | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(NCCCNC(=O)OC(C)(C)C)c1>[Pd].C(C)(=O)OCC.C(C)O>CC(C)CCN(CCC(C)C)C(=O)c1ccc(N)c(NCCCNC(=O)OC(C)(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fc8de8111f194d8c9532cad28e293438 | CC(C)CCN(CCC(C)C)C(=O)c1ccc(N)c(NCCCNC(=O)OC(C)(C)C)c1.COC(=O)c1ccc(N=C=S)cc1>>COC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCCNC(=O)OC(C)(C)C)cc1 | COC(=O)C1=CC=C(C=C1)N=C=S.C(C)(C)(C)OC(NCCCNC1=C(C=CC(=C1)C(=O)N(CCC(C)C)CCC(C)C)N)=O>>CC(CCN(C(=O)C=1C=CC2=C(N(C(=N2)NC2=CC=C(C(=O)OC)C=C2)CCCNC(=O)OC(C)(C)C)C1)CCC(C)C)C | [NH2:11][c:12]1[cH:13][cH:14][c:15]([C:16](=[O:17])[N:18]([CH2:19][CH2:20][CH:21]([CH3:22])[CH3:23])[CH2:24][CH2:25][CH:26]([CH3:27])[CH3:28])[cH:29][c:30]1[NH:31][CH2:32][CH2:33][CH2:34][NH:35][C:36](=[O:37])[O:38][C:39]([CH3:40])([CH3:41])[CH3:42].S=[C:10]=[N:9][c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:44... | CC(C)CCN(CCC(C)C)C(=O)c1ccc(N)c(NCCCNC(=O)OC(C)(C)C)c1.COC(=O)c1ccc(N=C=S)cc1 | COC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCCNC(=O)OC(C)(C)C)cc1 | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | 4b3e260fa6094641dfa114b35f3471079a338332f41031b31ba4b7bb465b4139 | c2745d0d96944794048cb0a435469fb3c0efa689f6d5e8d4fd6447372cabc5f8 | c1ccc(Nc2nc3ccccc3[nH]2)cc1 | S=[C;H0;D2;+0:1]=[N;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11](-[NH2;D1;+0:12]):[c:13]>>[C:6]-[C:7]-[n;H0;D3;+0:8]1:[c:9](:[c:10]):[c:11](:[c:13]):[n;H0;D2;+0:12]:[c;H0;D3;+0:1]:1-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5] | 60 | [{"value": 60.0, "product": "CC(CCN(C(=O)C=1C=CC2=C(N(C(=N2)NC2=CC=C(C(=O)OC)C=C2)CCCNC(=O)OC(C)(C)C)C1)CCC(C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | 4-methoxycarbonylphenyl isothiocyanate (327 mg, 1.5 eq) and N-methylcyclohexylcarbodiimide-N-methyl-polystyrene resin (acquired from Novabiochem; charge 1.9 mmol/g; 1.75 g, 3 eq) are added successively to a solution of tert-butyl-3-[(2-amino-5-{[bis(3-methylbutyl)amino]carbonyl}phenyl)amino]propylcarbamate (500 mg, 1 e... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine.Isothiocyanate | Secondary amine | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccccc1.c1ccc2[nH]cnc2c1 | Other | O1CCCC1 | null | 4 | CC(C)CCN(CCC(C)C)C(=O)c1ccc(N)c(NCCCNC(=O)OC(C)(C)C)c1.COC(=O)c1ccc(N=C=S)cc1>O1CCCC1>COC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCCNC(=O)OC(C)(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-31e8348712204ffbb3517d151923c82d | COC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCCNC(=O)OC(C)(C)C)cc1>>COC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCCN)cc1.Cl | Cl.CC(CCN(C(=O)C=1C=CC2=C(N(C(=N2)NC2=CC=C(C(=O)OC)C=C2)CCCNC(=O)OC(C)(C)C)C1)CCC(C)C)C>>Cl.Cl.NCCCN1C(=NC2=C1C=C(C=C2)C(=O)N(CCC(C)C)CCC(C)C)NC2=CC=C(C(=O)OC)C=C2 | CC(C)(C)OC(=O)[NH:35][CH2:34][CH2:33][CH2:32][n:31]1[c:10]([NH:9][c:8]2[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:37][cH:36]2)[n:11][c:12]2[cH:13][cH:14][c:15]([C:16](=[O:17])[N:18]([CH2:19][CH2:20][CH:21]([CH3:22])[CH3:23])[CH2:24][CH2:25][CH:26]([CH3:27])[CH3:28])[cH:29][c:30]21>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[... | COC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCCNC(=O)OC(C)(C)C)cc1 | COC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCCN)cc1.Cl | null | null | O1CCOCC1.C(C)(=O)OCC | Miscellaneous | Hydrogenolysis of amides/imides/carbamates | 4812e39fa209f57a5a2564677791e5e37790c829f5742d8c7df33806c5ba4ce0 | d7ecc2e7a68b8c20d378ac6004c3fdfc3efd09bbbd9efd577186f69427135737 | c1ccc(Nc2nc3ccccc3[nH]2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | 96 | [{"value": 96.0, "product": "Cl.Cl.NCCCN1C(=NC2=C1C=C(C=C2)C(=O)N(CCC(C)C)CCC(C)C)NC2=CC=C(C(=O)OC)C=C2", "details": "PERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 1 | HOUR | A solution of hydrochloric acid in dioxane (4N, 2 ml) is added to a solution of methyl 4-[(6-{[bis(3-methylbutyl)amino]carbonyl}-1-{3-[(tert-butoxycarbonyl)amino]propyl}-1H-benzimidazol-2-yl)amino]benzoate (180 mg) in ethyl acetate (2 ml). After stirring for 1 hour at a temperature of approximately 20° C., the mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ccc2[nH]cnc2c1 | HO- | O1CCOCC1.C(C)(=O)OCC | 20 | 1 | COC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCCNC(=O)OC(C)(C)C)cc1>O1CCOCC1.C(C)(=O)OCC>COC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCCN)cc1.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4c860cc4d2c9450a8016f21b48a21c1b | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(F)c1.NCCCN1CCCCC1>>CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(NCCCN2CCCCC2)c1 | FC=1C=C(C(=O)N(CCC(C)C)CCC(C)C)C=CC1[N+](=O)[O-].N1(CCCCC1)CCCN.C([O-])([O-])=O.[K+].[K+]>>CC(CCN(C(C1=CC(=C(C=C1)[N+](=O)[O-])NCCCN1CCCCC1)=O)CCC(C)C)C | F[c:21]1[c:17]([N+:18](=[O:19])[O-:20])[cH:16][cH:15][c:14]([C:12]([N:6]([CH2:5][CH2:4][CH:2]([CH3:1])[CH3:3])[CH2:7][CH2:8][CH:9]([CH3:10])[CH3:11])=[O:13])[cH:32]1.[NH2:22][CH2:23][CH2:24][CH2:25][N:26]1[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][N:6]([CH2:7][CH2:8][CH:9]([CH3:10])... | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(F)c1.NCCCN1CCCCC1 | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(NCCCN2CCCCC2)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(NCCCN2CCCCC2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](-[#7:5])=[O;D1;H0:6]):[c:7](-[#7;+:8]):[c:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[#7:5]-[C:4](=[O;D1;H0:6])-[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:12]-[C:11]-[C:10]):[c:7](-[#7;+:8]):[c:9] | 78 | [{"value": 78.0, "product": "CC(CCN(C(C1=CC(=C(C=C1)[N+](=O)[O-])NCCCN1CCCCC1)=O)CCC(C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-fluoro-N,N-bis(3-methylbutyl)-4-nitrobenzamide (430 mg, 1 eq, prepared according to Example A1), 3-piperidino-propylamine (212 mg, 1.1 eq) and potassium carbonate (365 mg, 2 eq) in acetonitrile (10 ml) is heated under reflux for 3 hours then concentrated under reduced pressure at 40° C. The residue is ta... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CC[NH]CC1 | HF | C(C)#N | null | null | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(F)c1.NCCCN1CCCCC1>C(C)#N>CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(NCCCN2CCCCC2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2a692e45e1de47b292bd69fefe7aa0ac | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(F)c1.CCN(CC)CCCN>>CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(NCCCN(C)C)c1 | FC=1C=C(C(=O)N(CCC(C)C)CCC(C)C)C=CC1[N+](=O)[O-].C(C)N(CCCN)CC.C([O-])([O-])=O.[K+].[K+]>>CN(CCCNC=1C=C(C(=O)N(CCC(C)C)CCC(C)C)C=CC1[N+](=O)[O-])C | F[c:21]1[c:17]([N+:18](=[O:19])[O-:20])[cH:16][cH:15][c:14]([C:12]([N:6]([CH2:5][CH2:4][CH:2]([CH3:1])[CH3:3])[CH2:7][CH2:8][CH:9]([CH3:10])[CH3:11])=[O:13])[cH:29]1.C[CH2:27][N:26]([CH2:25][CH2:24][CH2:23][NH2:22])[CH2:28]C>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][N:6]([CH2:7][CH2:8][CH:9]([CH3:10])[CH3:11])[C:12](=[O:13... | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(F)c1.CCN(CC)CCCN | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(NCCCN(C)C)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccccc1 | C-[CH2;D2;+0:1]-[#7:2](-[C:3]-[C:4]-[C:5]-[NH2;D1;+0:6])-[CH2;D2;+0:7]-C.F-[c;H0;D3;+0:8](:[c:9]:[c:10]-[C:11](-[#7:12])=[O;D1;H0:13]):[c:14](-[#7;+:15]):[c:16]>>[#7:12]-[C:11](=[O;D1;H0:13])-[c:10]:[c:9]:[c;H0;D3;+0:8](-[NH;D2;+0:6]-[C:5]-[C:4]-[C:3]-[#7:2](-[CH3;D1;+0:1])-[CH3;D1;+0:7]):[c:14](-[#7;+:15]):[c:16] | 68 | [{"value": 68.0, "product": "CN(CCCNC=1C=C(C(=O)N(CCC(C)C)CCC(C)C)C=CC1[N+](=O)[O-])C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-fluoro-N,N-bis(3-methylbutyl)-4-nitrobenzamide (2.5 g, 1 eq, prepared according to Example A1), 3-diethylamino-propylamine (877 mg, 1.1 eq) and potassium carbonate (2.13 g, 2 eq) in acetonitrile (80 ml) is heated under reflux for hours then concentrated under reduced pressure at 40° C. The residue is tak... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | C(C)#N | null | null | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(F)c1.CCN(CC)CCCN>C(C)#N>CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(NCCCN(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2de8ee03c280411cbc49ee75ebf58a1a | CC(C)(C)OC(=O)Nc1ccc(N)cc1.CON>>CONC(=O)Nc1ccc(NC(=O)OC(C)(C)C)cc1 | Cl.CON.C(O)([O-])=O.[Na+].C(=O)(C=1NC=CN1)C=1NC=CN1.NC1=CC=C(C=C1)NC(OC(C)(C)C)=O.C(C)N(CC)CC>>CONC(=O)NC1=CC=C(C=C1)NC(OC(C)(C)C)=O | [NH2:6][c:7]1[cH:8][cH:9][c:10]([NH:11][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[cH:19][cH:20]1.[CH3:1][O:2][NH2:3]>>[CH3:1][O:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][cH:9][c:10]([NH:11][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[cH:19][cH:20]1 | CC(C)(C)OC(=O)Nc1ccc(N)cc1.CON | CONC(=O)Nc1ccc(NC(=O)OC(C)(C)C)cc1 | null | null | ClCCl.O.C(Cl)(Cl)Cl | Acylation | OtherReaction | 0803607fba0d95b5aa54f50a0ea365a82edda165361e01ad9e7ff57568bb8df0 | 4ff96020857e85930fbee987c7fa4ef615e45b2ea39cff27ceaec8f9174d5b6f | c1ccccc1 | [C;D1;H3:1]-[#8:2]-[NH2;D1;+0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:1]-[#8:2]-[NH;D2;+0:3]-[C:8](=[O;D1;H0:9])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 94.7 | [{"value": 94.7, "product": "CONC(=O)NC1=CC=C(C=C1)NC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 15 | HOUR | Carbonyl-di-imidazole (1.62 g, 2 eq) is added to a solution cooled down to 0° C., of tert-butyl 4-aminophenylcarbamate (1.04 g) in anhydrous dichloromethane (100 ml). The mixture is taken to a temperature of 20° C. and is stirred at this temperature for 15 hours. Triethylamine (7 ml, 10 eq) followed by O-methylhydroxyl... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine | Urea | null | null | c1ccccc1 | Other | ClCCl.O.C(Cl)(Cl)Cl | 0 | 15 | CC(C)(C)OC(=O)Nc1ccc(N)cc1.CON>ClCCl.O.C(Cl)(Cl)Cl>CONC(=O)Nc1ccc(NC(=O)OC(C)(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f70cbf7a67da443888280460bc8b1bea | CONC(=O)Nc1ccc(N)cc1.S=C(Cl)Cl>>CONC(=O)Nc1ccc(N=C=S)cc1 | Cl.NC1=CC=C(C=C1)NC(=O)NOC.C(C)N(CC)CC.C(=S)(Cl)Cl.O>>N(=C=S)C1=CC=C(C=C1)NC(=O)NOC | [CH3:1][O:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][cH:9][c:10]([NH2:11])[cH:14][cH:15]1.Cl[C:12](Cl)=[S:13]>>[CH3:1][O:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][cH:9][c:10]([N:11]=[C:12]=[S:13])[cH:14][cH:15]1 | CONC(=O)Nc1ccc(N)cc1.S=C(Cl)Cl | CONC(=O)Nc1ccc(N=C=S)cc1 | null | null | O1CCCC1.C(C)OCC | Heteroatom Alkylation and Arylation | Amine and thiophosgene to isothiocyanate | 1226380c52141f79542a4f85564c11e38ca245efc80be1557b635219a638388c | e5752ca9983a57ab07a0b76a5c8a57a6667ab2cd460616b960134623ec0fce31 | c1ccccc1 | Cl-[C;H0;D3;+0:1](-Cl)=[S;D1;H0:2].[NH2;D1;+0:3]-[c:4](:[c:5]):[c:6]>>[S;D1;H0:2]=[C;H0;D2;+0:1]=[N;H0;D2;+0:3]-[c:4](:[c:5]):[c:6] | 62 | [{"value": 62.0, "product": "N(=C=S)C1=CC=C(C=C1)NC(=O)NOC", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 15 | MINUTE | Thiophosgene (0.38 ml, 1.1 eq) is added dropwise to a solution cooled down to 0° C., of N-(4-aminophenyl)-N′-methoxyurea hydrochloride (1 g) and triethylamine (3.2 ml, 5 eq) in tetrahydrofuran (90 ml). The mixture is stirred for 15 min at 0° C. then water and diethyl ether are added. After decantation and extractions, ... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Alkenyl halide.Primary amine | Isothiocyanate | null | null | c1ccccc1 | HCl | O1CCCC1.C(C)OCC | 0 | 0.25 | CONC(=O)Nc1ccc(N)cc1.S=C(Cl)Cl>O1CCCC1.C(C)OCC>CONC(=O)Nc1ccc(N=C=S)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ffcd27c13af2459bb65a0f9ff902e5f1 | COC(=O)c1ccc(C(=O)Cl)cc1.N#C[S-]>>COC(=O)c1ccc(C(=O)N=C=S)cc1 | [S-]C#N.[K+].ClC(=O)C1=CC=C(C(=O)OC)C=C1>>N(=C=S)C(=O)C1=CC=C(C(=O)OC)C=C1 | Cl[C:9]([c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:15][cH:14]1)=[O:10].[N:11]#[C:12][S-:13]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[N:11]=[C:12]=[S:13])[cH:14][cH:15]1 | COC(=O)c1ccc(C(=O)Cl)cc1.N#C[S-] | COC(=O)c1ccc(C(=O)N=C=S)cc1 | null | null | C(C)#N | Acylation | OtherReaction | c7e68a1fa6ac27c3709bff81e45d4a7a4c0739b1f7c19440be50a653bd0f64cf | 424f8e293ba0b1403ae5b768e3028ff5c90d55f9a9629c56f4dcf4b5b2a529b7 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[N;H0;D1;+0:6]#[C;H0;D2;+0:7]-[S-;H0;D1:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D2;+0:6]=[C;H0;D2;+0:7]=[S;H0;D1;+0:8])-[c:3](:[c:4]):[c:5] | 95 | [{"value": 95.0, "product": "N(=C=S)C(=O)C1=CC=C(C(=O)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.3, "product": "N(=C=S)C(=O)C1=CC=C(C(=O)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 1 | HOUR | Potassium thiocyanate (1.08 g) is added to a solution of methyl 4-chlorocarbonylbenzoate (2 g) in acetonitrile (30 ml). After stirring for 1 hour at approximately 20° C., the mixture is filtered and the filtrate is concentrated under reduced pressure at 40° C. The solid obtained is purified by flash chromatography on s... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Nitrile | Isothiocyanate | null | null | c1ccccc1 | Other | C(C)#N | 20 | 1 | COC(=O)c1ccc(C(=O)Cl)cc1.N#C[S-]>C(C)#N>COC(=O)c1ccc(C(=O)N=C=S)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9d1aad5b96d74c4b8570f2681439c8f4 | C[Si](C)(C)C=[N+]=[N-].O=C(O)c1ccc([N+](=O)[O-])c(F)c1>>COC(=O)c1ccc([N+](=O)[O-])c(F)c1 | C[Si](C)(C)C=[N+]=[N-].FC=1C=C(C(=O)O)C=CC1[N+](=O)[O-]>>FC=1C=C(C(=O)OC)C=CC1[N+](=O)[O-] | C[Si](C)(C)[CH:1]=[N+]=[N-].[OH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[c:12]([F:13])[cH:14]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[c:12]([F:13])[cH:14]1 | C[Si](C)(C)C=[N+]=[N-].O=C(O)c1ccc([N+](=O)[O-])c(F)c1 | COC(=O)c1ccc([N+](=O)[O-])c(F)c1 | null | null | CO | Heteroatom Alkylation and Arylation | O-alkylation of carboxylic acids with diazo compounds | 39589be0e9a30df66714fe618d22a8ac0fb24901dbf2ead1ab33e31556c7ac64 | 8b539baf7aeb5ab868833e33306bad77200a853d562904197e13de2e27e229d7 | c1ccccc1 | C-[Si](-C)(-C)-[CH;D2;+0:1]=[N+]=[N-].[O;D1;H0:2]=[C:3](-[OH;D1;+0:4])-[c:5]>>[CH3;D1;+0:1]-[O;H0;D2;+0:4]-[C:3](=[O;D1;H0:2])-[c:5] | 87 | [{"value": 87.0, "product": "FC=1C=C(C(=O)OC)C=CC1[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of trimethylsilyldiazomethane (2M in hexane, 50 ml, 4 eq) is slowly added to a solution of 3-fluoro-4-nitrobenzoic acid (4.7 g, 1 eq) in methanol (70 ml) until the gas evolution ceases. The excess trimethylsilyldiazomethane is consumed by the dropwise addition of acetic acid until the solution becomes discol... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Diazo.Silyl protective group | Ester | null | null | c1ccccc1 | Other | CO | null | null | C[Si](C)(C)C=[N+]=[N-].O=C(O)c1ccc([N+](=O)[O-])c(F)c1>CO>COC(=O)c1ccc([N+](=O)[O-])c(F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5dca9ab7fbeb4f2f8efd5f4ab45c5a74 | CC(C)(C)OC(=O)NCCCN.COC(=O)c1ccc([N+](=O)[O-])c(F)c1>>COC(=O)c1ccc([N+](=O)[O-])c(NCCCNC(=O)OC(C)(C)C)c1 | FC=1C=C(C(=O)OC)C=CC1[N+](=O)[O-].C(=O)(OC(C)(C)C)NCCCN.C([O-])([O-])=O.[K+].[K+]>>C(C)(C)(C)OC(=O)NCCCNC=1C=C(C(=O)OC)C=CC1[N+](=O)[O-] | [NH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24].F[c:12]1[c:8]([N+:9](=[O:10])[O-:11])[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:25]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[c:12]([NH:13][CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:19])[O... | CC(C)(C)OC(=O)NCCCN.COC(=O)c1ccc([N+](=O)[O-])c(F)c1 | COC(=O)c1ccc([N+](=O)[O-])c(NCCCNC(=O)OC(C)(C)C)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](-[#8:5])=[O;D1;H0:6]):[c:7](-[#7;+:8]):[c:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[#7;+:8]-[c:7](:[c:9]):[c;H0;D3;+0:1](-[NH;D2;+0:12]-[C:11]-[C:10]):[c:2]:[c:3]-[C:4](-[#8:5])=[O;D1;H0:6] | 99 | [{"value": 99.0, "product": "C(C)(C)(C)OC(=O)NCCCNC=1C=C(C(=O)OC)C=CC1[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of methyl 3-fluoro-4-nitrobenzoate (5.8 g, 1 eq), N-Boc-1,3-diaminopropane (5.75 g, 1.1 eq) and potassium carbonate (8.04 g, 2 eq) in acetonitrile (200 ml) is heated under reflux for 2 hours then concentrated under reduced pressure at 40° C. The residue is taken up in dichloromethane (200 ml) and water (100 m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | C(C)#N | null | null | CC(C)(C)OC(=O)NCCCN.COC(=O)c1ccc([N+](=O)[O-])c(F)c1>C(C)#N>COC(=O)c1ccc([N+](=O)[O-])c(NCCCNC(=O)OC(C)(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-180b2a43ee394760afc364e4b59248bb | COC(=O)c1ccc([N+](=O)[O-])c(NCCCNC(=O)OC(C)(C)C)c1>>COC(=O)c1ccc(N)c(NCCCNC(=O)OC(C)(C)C)c1 | C(C)(C)(C)OC(=O)NCCCNC=1C=C(C(=O)OC)C=CC1[N+](=O)[O-]>>NC1=C(C=C(C(=O)OC)C=C1)NCCCNC(=O)OC(C)(C)C | O=[N+:9]([O-])[c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:23][c:10]1[NH:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[c:10]([NH:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21... | COC(=O)c1ccc([N+](=O)[O-])c(NCCCNC(=O)OC(C)(C)C)c1 | COC(=O)c1ccc(N)c(NCCCNC(=O)OC(C)(C)C)c1 | null | [Pd] | C(C)(=O)OCC.CO | 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] | 83 | [{"value": 83.0, "product": "NC1=C(C=C(C(=O)OC)C=C1)NCCCNC(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 4 | HOUR | Methyl 3-({3-[(tert-butoxycarbonyl)amino]propyl}amino)-4-nitrobenzoate (10.2 g) in solution in a mixture of ethyl acetate/methanol 3:1 (300 ml), and 10% palladium on carbon (1.02 g) are introduced into an autoclave. After stirring for 4 hours under a hydrogen atmosphere (3 bar) at a temperature of approximately 20° C.,... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Pd].C(C)(=O)OCC.CO | 20 | 4 | COC(=O)c1ccc([N+](=O)[O-])c(NCCCNC(=O)OC(C)(C)C)c1>[Pd].C(C)(=O)OCC.CO>COC(=O)c1ccc(N)c(NCCCNC(=O)OC(C)(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1cc8f634dcac4421aae6a72f64e53a53 | COC(=O)c1ccc(N)c(NCCCNC(=O)OC(C)(C)C)c1.COc1cc(N=C=S)cc(OC)c1OC>>COC(=O)c1ccc2nc(Nc3cc(OC)c(OC)c(OC)c3)n(CCCNC(=O)OC(C)(C)C)c2c1 | COC=1C=C(C=C(C1OC)OC)N=C=S.C(C)(C)N=C=NC(C)C.NC1=C(C=C(C(=O)OC)C=C1)NCCCNC(=O)OC(C)(C)C>>C(C)(C)(C)OC(=O)NCCCN1C(=NC2=C1C=C(C=C2)C(=O)OC)NC2=CC(=C(C(=C2)OC)OC)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[c:36]([NH:24][CH2:25][CH2:26][CH2:27][NH:28][C:29](=[O:30])[O:31][C:32]([CH3:33])([CH3:34])[CH3:35])[cH:37]1.S=[C:10]=[N:11][c:12]1[cH:13][c:14]([O:15][CH3:16])[c:17]([O:18][CH3:19])[c:20]([O:21][CH3:22])[cH:23]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]... | COC(=O)c1ccc(N)c(NCCCNC(=O)OC(C)(C)C)c1.COc1cc(N=C=S)cc(OC)c1OC | COC(=O)c1ccc2nc(Nc3cc(OC)c(OC)c(OC)c3)n(CCCNC(=O)OC(C)(C)C)c2c1 | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | 4b3e260fa6094641dfa114b35f3471079a338332f41031b31ba4b7bb465b4139 | c2745d0d96944794048cb0a435469fb3c0efa689f6d5e8d4fd6447372cabc5f8 | c1ccc(Nc2nc3ccccc3[nH]2)cc1 | S=[C;H0;D2;+0:1]=[N;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11](-[NH2;D1;+0:12]):[c:13]>>[C:6]-[C:7]-[n;H0;D3;+0:8]1:[c:9](:[c:10]):[c:11](:[c:13]):[n;H0;D2;+0:12]:[c;H0;D3;+0:1]:1-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | 3,4,5-trimethoxyphenyl isothiocyanate (6.6 g, 1.2 eq) and diisopropylcarbodiimide (9.1 g, 3 eq) are successively added to a solution of methyl 4-amino-3-({3-[(tert-butoxycarbonyl)amino]propyl}amino)benzoate (7.75 g, 1 eq) in tetrahydrofuran (130 ml). The mixture is heated under reflux for 16 hours then cooled down to a... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine.Isothiocyanate | Secondary amine | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1.c1ccccc1 | Other | O1CCCC1 | null | null | COC(=O)c1ccc(N)c(NCCCNC(=O)OC(C)(C)C)c1.COc1cc(N=C=S)cc(OC)c1OC>O1CCCC1>COC(=O)c1ccc2nc(Nc3cc(OC)c(OC)c(OC)c3)n(CCCNC(=O)OC(C)(C)C)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3e10157676b043fcab1fd29762e827c7 | COC(=O)c1ccc2nc(Nc3cc(OC)c(OC)c(OC)c3)n(CCCNC(=O)OC(C)(C)C)c2c1>>COc1cc(Nc2nc3ccc(C(=O)O)cc3n2CCCNC(=O)OC(C)(C)C)cc(OC)c1OC | [OH-].[Li+].C(C)(C)(C)OC(=O)NCCCN1C(=NC2=C1C=C(C=C2)C(=O)OC)NC2=CC(=C(C(=C2)OC)OC)OC>>C(C)(C)(C)OC(=O)NCCCN1C(=NC2=C1C=C(C=C2)C(=O)O)NC2=CC(=C(C(=C2)OC)OC)OC | C[O:15][C:13]([c:12]1[cH:11][cH:10][c:9]2[n:8][c:7]([NH:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:34]([O:35][CH3:36])[c:31]([O:32][CH3:33])[cH:30]3)[n:18]([CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[c:17]2[cH:16]1)=[O:14]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[n:8][c:9]3[cH:10... | COC(=O)c1ccc2nc(Nc3cc(OC)c(OC)c(OC)c3)n(CCCNC(=O)OC(C)(C)C)c2c1 | COc1cc(Nc2nc3ccc(C(=O)O)cc3n2CCCNC(=O)OC(C)(C)C)cc(OC)c1OC | null | null | O1CCCC1.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Nc2nc3ccccc3[nH]2)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] | null | [] | null | null | null | null | Lithium hydroxide (2.18 g, 6 eq) is added to a solution of methyl 1-{3-[(tert-butoxycarbonyl)amino]propyl}-2-[(3,4,5-trimethoxyphenyl)amino]-1H-benzimidazole-6-carboxylate (4.4 g, 1 eq) in a mixture of tetrahydrofuran (40 ml) and water (30 ml). The mixture is heated under reflux for 18 hours then cooled down to ambient... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccc2[nH]cnc2c1 | Other | O1CCCC1.O | null | null | COC(=O)c1ccc2nc(Nc3cc(OC)c(OC)c(OC)c3)n(CCCNC(=O)OC(C)(C)C)c2c1>O1CCCC1.O>COc1cc(Nc2nc3ccc(C(=O)O)cc3n2CCCNC(=O)OC(C)(C)C)cc(OC)c1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-19fe0008457441a79b7b1921281ee2f8 | C1CCNCC1.COc1cc(Nc2nc3ccc(C(=O)O)cc3n2CCCNC(=O)OC(C)(C)C)cc(OC)c1OC>>COc1cc(Nc2nc3ccc(C(=O)N4CCCCC4)cc3n2CCCN)cc(OC)c1OC.Cl | N1CCCCC1.Cl.C(=O)(N1C=NC=C1)N1C=NC=C1.C(C)(C)(C)OC(=O)NCCCN1C(=NC2=C1C=C(C=C2)C(=O)O)NC2=CC(=C(C(=C2)OC)OC)OC>>Cl.Cl.NCCCN1C(=NC2=C1C=C(C=C2)C(=O)N2CCCCC2)NC2=CC(=C(C(=C2)OC)OC)OC | [NH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1.CC(C)(C)OC(=O)[NH:27][CH2:26][CH2:25][CH2:24][n:23]1[c:7]([NH:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:32]([O:33][CH3:34])[c:29]([O:30][CH3:31])[cH:28]2)[n:8][c:9]2[cH:10][cH:11][c:12]([C:13](O)=[O:14])[cH:21][c:22]21>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[n:8][c:9]3[cH... | C1CCNCC1.COc1cc(Nc2nc3ccc(C(=O)O)cc3n2CCCNC(=O)OC(C)(C)C)cc(OC)c1OC | COc1cc(Nc2nc3ccc(C(=O)N4CCCCC4)cc3n2CCCN)cc(OC)c1OC.Cl | null | null | ClCCl.C(C)(=O)OCC.C(Cl)(Cl)Cl.O1CCCC1.CN(C=O)C | Acylation | OtherReaction | 4f8ccca95d869c8d3dcac786a435dba99d995a07df815bae744f7a819bbe3617 | 9cd01fe9ee5cb03a85922f937adad468b1a7e7d55c326a442ab91fc46e4b1c78 | O=C(c1ccc2nc(Nc3ccccc3)[nH]c2c1)N1CCCCC1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3].O-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6](:[c:7]):[c:8]:[c:9]:[#7;a:10].[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]>>[#7;a:10]:[c:9]:[c:8]:[c:6](-[C;H0;D3;+0:4](=[O;D1;H0:5])-[N;H0;D3;+0:13](-[C:12]-[C:11])-[C:14]-[C:15]):[c:7].[C:3]-[C:2]-[NH2;D1;+0:1] | 65 | [{"value": 65.0, "product": "Cl.Cl.NCCCN1C(=NC2=C1C=C(C=C2)C(=O)N2CCCCC2)NC2=CC(=C(C(=C2)OC)OC)OC", "details": "PERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 16 | HOUR | A solution of carbonyldiimidazole (CDI) (18 mg, 1.1 eq) in chloroform (0.2 ml) is added to a solution of 1-{3-[(tert-butoxycarbonyl)amino]propyl}-2-[(3,4,5-trimethoxyphenyl)amino]-1H-benzimidazole-6-carboxylic acid (50 mg, 1 eq) in tetrahydrofuran (0.45 ml) and dimethylformamide (0.05 ml). The mixture is stirred for 16... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Secondary amine.Boc | Tertiary amide.Primary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.c1ccc2[nH]cnc2c1.C1CC[NH]CC1 | HO- | ClCCl.C(C)(=O)OCC.C(Cl)(Cl)Cl.O1CCCC1.CN(C=O)C | 20 | 16 | C1CCNCC1.COc1cc(Nc2nc3ccc(C(=O)O)cc3n2CCCNC(=O)OC(C)(C)C)cc(OC)c1OC>ClCCl.C(C)(=O)OCC.C(Cl)(Cl)Cl.O1CCCC1.CN(C=O)C>COc1cc(Nc2nc3ccc(C(=O)N4CCCCC4)cc3n2CCCN)cc(OC)c1OC.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a9485a3a19294f69b497b8d94a3cf48f | CC(C)(C)C=O.COc1cc(Nc2nc3ccc(C(=O)N(CC(C)C)CC(C)C)cc3n2CCCN)cc(OC)c1OC.ClCCl.ClCCl>>COc1cc(Nc2nc3ccc(C(=O)N(CC(C)C)CC(C)C)cc3n2CCCNCC(C)(C)C)cc(OC)c1OC.Cl.Cl | NCCCN1C(=NC2=C1C=C(C=C2)C(=O)N(CC(C)C)CC(C)C)NC2=CC(=C(C(=C2)OC)OC)OC.CC(C=O)(C)C.ClCCl.C(O)([O-])=O.[Na+].ClCCl.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>Cl.Cl.C(C(C)C)N(C(=O)C=1C=CC2=C(N(C(=N2)NC2=CC(=C(C(=C2)OC)OC)OC)CCCNCC(C)(C)C)C1)CC(C)C | O=[CH:31][C:32]([CH3:33])([CH3:34])[CH3:35].[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[n:8][c:9]3[cH:10][cH:11][c:12]([C:13](=[O:14])[N:15]([CH2:16][CH:17]([CH3:18])[CH3:19])[CH2:20][CH:21]([CH3:22])[CH3:23])[cH:24][c:25]3[n:26]2[CH2:27][CH2:28][CH2:29][NH2:30])[cH:36][c:37]([O:38][CH3:39])[c:40]1[O:41][CH3:42].ClC[Cl:... | CC(C)(C)C=O.COc1cc(Nc2nc3ccc(C(=O)N(CC(C)C)CC(C)C)cc3n2CCCN)cc(OC)c1OC.ClCCl.ClCCl | COc1cc(Nc2nc3ccc(C(=O)N(CC(C)C)CC(C)C)cc3n2CCCNCC(C)(C)C)cc(OC)c1OC.Cl.Cl | null | null | O.CO | Heteroatom Alkylation and Arylation | OtherReaction | 016c9849d927236ad312c4a1ada4bb312217ef63df13cd653676c1c8436029c1 | a6638cc6afd7e4d9005f7b96ad12e3d567dce3969c1c4003fb4b0c32cc0506ba | c1ccc(Nc2nc3ccccc3[nH]2)cc1 | Cl-C-[Cl;H0;D1;+0:1].Cl-C-[Cl;H0;D1;+0:2].O=[CH;D2;+0:3]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[C:8]-[C:9]-[NH2;D1;+0:10]>>[C:8]-[C:9]-[NH;D2;+0:10]-[CH2;D2;+0:3]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[ClH;D0;+0:1].[ClH;D0;+0:2] | null | [] | null | null | null | null | A solution of 1-(3-aminopropyl)-N,N-diisobutyl-2-[(3,4,5-trimethoxyphenyl)amino]-1H-benzimidazole-6-carboxamide (100 mg, 1 eq) and trimethylacetaldehyde (25 mg, 1.5 eq) in dichloromethane (1 ml) is stirred for 4 hours at a temperature of approximately 20° C. The mixture is diluted with methanol (1 ml) then sodium triac... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Primary halide.Primary halide.Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccc2[nH]cnc2c1 | HCl | O.CO | null | null | CC(C)(C)C=O.COc1cc(Nc2nc3ccc(C(=O)N(CC(C)C)CC(C)C)cc3n2CCCN)cc(OC)c1OC.ClCCl.ClCCl>O.CO>COc1cc(Nc2nc3ccc(C(=O)N(CC(C)C)CC(C)C)cc3n2CCCNCC(C)(C)C)cc(OC)c1OC.Cl.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f7774b1580534680a4b78f29a99fddb0 | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(F)c1.NCCC1OCCO1>>CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(NCCC2OCCO2)c1 | C([O-])([O-])=O.[K+].[K+].FC=1C=C(C(=O)N(CCC(C)C)CCC(C)C)C=CC1[N+](=O)[O-].NCCC1OCCO1>>O1C(OCC1)CCNC=1C=C(C(=O)N(CCC(C)C)CCC(C)C)C=CC1[N+](=O)[O-] | F[c:21]1[c:17]([N+:18](=[O:19])[O-:20])[cH:16][cH:15][c:14]([C:12]([N:6]([CH2:5][CH2:4][CH:2]([CH3:1])[CH3:3])[CH2:7][CH2:8][CH:9]([CH3:10])[CH3:11])=[O:13])[cH:30]1.[NH2:22][CH2:23][CH2:24][CH:25]1[O:26][CH2:27][CH2:28][O:29]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][N:6]([CH2:7][CH2:8][CH:9]([CH3:10])[CH3:11])[C:12](=[O... | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(F)c1.NCCC1OCCO1 | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(NCCC2OCCO2)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(NCCC2OCCO2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](-[#7:5])=[O;D1;H0:6]):[c:7](-[#7;+:8]):[c:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[#7:5]-[C:4](=[O;D1;H0:6])-[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:12]-[C:11]-[C:10]):[c:7](-[#7;+:8]):[c:9] | 98 | [{"value": 98.0, "product": "O1C(OCC1)CCNC=1C=C(C(=O)N(CCC(C)C)CCC(C)C)C=CC1[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-fluoro-N,N-bis(3-methylbutyl)-4-nitrobenzamide prepared according to Example A1 (1.86 g, 1 eq), 2-(2-aminoethyl)-1,3-dioxolane (0.8 g, 1.2 eq) and potassium carbonate (1.58 g, 2 eq) in acetonitrile (150 ml) is heated under reflux for 3 hours then concentrated under reduced pressure at 40° C. The residue ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.C1COCO1 | HF | C(C)#N | null | null | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(F)c1.NCCC1OCCO1>C(C)#N>CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(NCCC2OCCO2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e087c53a4ba54515a9918cef10627267 | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(NCCC2OCCO2)c1>>CC(C)CCN(CCC(C)C)C(=O)c1ccc(N)c(NCCC2OCCO2)c1 | O1C(OCC1)CCNC=1C=C(C(=O)N(CCC(C)C)CCC(C)C)C=CC1[N+](=O)[O-]>>NC1=C(C=C(C(=O)N(CCC(C)C)CCC(C)C)C=C1)NCCC1OCCO1 | O=[N+:18]([O-])[c:17]1[cH:16][cH:15][c:14]([C:12]([N:6]([CH2:5][CH2:4][CH:2]([CH3:1])[CH3:3])[CH2:7][CH2:8][CH:9]([CH3:10])[CH3:11])=[O:13])[cH:28][c:19]1[NH:20][CH2:21][CH2:22][CH:23]1[O:24][CH2:25][CH2:26][O:27]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][N:6]([CH2:7][CH2:8][CH:9]([CH3:10])[CH3:11])[C:12](=[O:13])[c:14]1[... | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(NCCC2OCCO2)c1 | CC(C)CCN(CCC(C)C)C(=O)c1ccc(N)c(NCCC2OCCO2)c1 | null | [Pd] | C(C)(=O)OCC.CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(NCCC2OCCO2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 89 | [{"value": 89.0, "product": "NC1=C(C=C(C(=O)N(CCC(C)C)CCC(C)C)C=C1)NCCC1OCCO1", "details": "PERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 4 | HOUR | 3-{[2-(1,3-dioxolan-2-yl)ethyl]amino}-N,N-bis(3-methylbutyl)-4-nitrobenzamide (2.4 g) in solution in a mixture of ethyl acetate/methanol 2:1 (100 ml), and 10% palladium on carbon (240 mg) are introduced into an autoclave. After stirring for 4 hours under a hydrogen atmosphere (3 bar) at a temperature of approximately 2... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.C1COCO1 | Other | [Pd].C(C)(=O)OCC.CO | 20 | 4 | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(NCCC2OCCO2)c1>[Pd].C(C)(=O)OCC.CO>CC(C)CCN(CCC(C)C)C(=O)c1ccc(N)c(NCCC2OCCO2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-72f0515c3875442381455f1f595d6186 | CC(=O)c1ccc(N=C=S)cc1.CC(C)CCN(CCC(C)C)C(=O)c1ccc(N)c(NCCC2OCCO2)c1>>CC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCC2OCCO2)cc1 | C(C)(=O)C1=CC=C(C=C1)N=C=S.C(C)(C)N=C=NC(C)C.NC1=C(C=C(C(=O)N(CCC(C)C)CCC(C)C)C=C1)NCCC1OCCO1>>C(C)(=O)C1=CC=C(C=C1)NC1=NC2=C(N1CCC1OCCO1)C=C(C=C2)C(=O)N(CCC(C)C)CCC(C)C | S=[C:9]=[N:8][c:7]1[cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:39][cH:38]1.[NH2:10][c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[N:17]([CH2:18][CH2:19][CH:20]([CH3:21])[CH3:22])[CH2:23][CH2:24][CH:25]([CH3:26])[CH3:27])[cH:28][c:29]1[NH:30][CH2:31][CH2:32][CH:33]1[O:34][CH2:35][CH2:36][O:37]1>>[CH3:1][C:2](=[O:3])[c:4]1[c... | CC(=O)c1ccc(N=C=S)cc1.CC(C)CCN(CCC(C)C)C(=O)c1ccc(N)c(NCCC2OCCO2)c1 | CC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCC2OCCO2)cc1 | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | 4b3e260fa6094641dfa114b35f3471079a338332f41031b31ba4b7bb465b4139 | c2745d0d96944794048cb0a435469fb3c0efa689f6d5e8d4fd6447372cabc5f8 | c1ccc(Nc2nc3ccccc3n2CCC2OCCO2)cc1 | S=[C;H0;D2;+0:1]=[N;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11](-[NH2;D1;+0:12]):[c:13]>>[C:6]-[C:7]-[n;H0;D3;+0:8]1:[c:9](:[c:10]):[c:11](:[c:13]):[n;H0;D2;+0:12]:[c;H0;D3;+0:1]:1-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5] | 66 | [{"value": 66.0, "product": "C(C)(=O)C1=CC=C(C=C1)NC1=NC2=C(N1CCC1OCCO1)C=C(C=C2)C(=O)N(CCC(C)C)CCC(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-acetylphenyl isothiocyanate (1.1 g, 1.2 eq) and diisopropylcarbodiimide (1.95 g, 3 eq) are successively added to a solution of 4-amino-3-{[2-(1,3-dioxolan-2-yl)ethyl]amino}-N,N-bis(3-methylbutyl)benzamide (2 g, 1 eq) in tetrahydrofuran (50 ml). The mixture is heated under reflux for 18 hours then cooled down to ambie... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine.Isothiocyanate | Secondary amine | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccccc1.c1ccc2[nH]cnc2c1.C1COCO1 | Other | O1CCCC1 | null | null | CC(=O)c1ccc(N=C=S)cc1.CC(C)CCN(CCC(C)C)C(=O)c1ccc(N)c(NCCC2OCCO2)c1>O1CCCC1>CC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCC2OCCO2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-adaca465f3b34baa90aecfc36bc9ebaf | CC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCC2OCCO2)cc1>>CC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCC=O)cc1 | C(C)(=O)C1=CC=C(C=C1)NC1=NC2=C(N1CCC1OCCO1)C=C(C=C2)C(=O)N(CCC(C)C)CCC(C)C.Cl>>C(C)(=O)C1=CC=C(C=C1)NC1=NC2=C(N1CCC=O)C=C(C=C2)C(=O)N(CCC(C)C)CCC(C)C | C1C[O:34][CH:33]([CH2:32][CH2:31][n:30]2[c:9]([NH:8][c:7]3[cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:36][cH:35]3)[n:10][c:11]3[cH:12][cH:13][c:14]([C:15](=[O:16])[N:17]([CH2:18][CH2:19][CH:20]([CH3:21])[CH3:22])[CH2:23][CH2:24][CH:25]([CH3:26])[CH3:27])[cH:28][c:29]32)O1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([NH... | CC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCC2OCCO2)cc1 | CC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCC=O)cc1 | null | null | O1CCCC1 | Miscellaneous | Acetal hydrolysis to aldehyde | f12636b09f9df336ccc8fe82b927db0e267bccc7cae0970f1f91c7ceed085225 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | c1ccc(Nc2nc3ccccc3[nH]2)cc1 | [C:1]-[C:2]-[CH;D3;+0:3]1-O-C-C-[O;H0;D2;+0:4]-1>>[C:1]-[C:2]-[CH;D2;+0:3]=[O;H0;D1;+0:4] | 99 | [{"value": 99.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 18 | HOUR | A solution of 2-[(4-acetylphenyl)amino]-1-[2-(1,3-dioxolan-2-yl)ethyl]-N,N-bis(3-methylbutyl)-1H-benzimidazole-6-carboxamide (900 mg) in a mixture of tetrahydrofuran (30 ml) and aqueous hydrochloric acid (3N, 40 ml) is stirred for 18 hours at a temperature of approximately 20° C. then concentrated under reduced pressur... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | C1COCO1 | null | c1ccccc1.c1ccc2[nH]cnc2c1 | HO- | O1CCCC1 | 20 | 18 | CC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCC2OCCO2)cc1>O1CCCC1>CC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCC=O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7d61ddc1f48d47a79a996dd8e841e019 | CC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCC=O)cc1.ClCCl.NCC1CCCCC1>>CC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCCNCC2CCCCC2)cc1.Cl.Cl | C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+].C(O)([O-])=O.[Na+].ClCCl.C(C)(=O)C1=CC=C(C=C1)NC1=NC2=C(N1CCC=O)C=C(C=C2)C(=O)N(CCC(C)C)CCC(C)C.NCC1CCCCC1>>Cl.Cl.C(C)(=O)C1=CC=C(C=C1)NC1=NC2=C(N1CCCNCC1CCCCC1)C=C(C=C2)C(=O)N(CCC(C)C)CCC(C)C | O=[CH:33][CH2:32][CH2:31][n:30]1[c:9]([NH:8][c:7]2[cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:43][cH:42]2)[n:10][c:11]2[cH:12][cH:13][c:14]([C:15](=[O:16])[N:17]([CH2:18][CH2:19][CH:20]([CH3:21])[CH3:22])[CH2:23][CH2:24][CH:25]([CH3:26])[CH3:27])[cH:28][c:29]21.C([Cl:44])[Cl:45].[NH2:34][CH2:35][CH:36]1[CH2:37][CH2:38][... | CC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCC=O)cc1.ClCCl.NCC1CCCCC1 | CC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCCNCC2CCCCC2)cc1.Cl.Cl | null | C(C)(=O)O | O.CO | Heteroatom Alkylation and Arylation | OtherReaction | 05249243ec4191ae0a34b72c1c53354c09eacc7795ccf55b263c625934998bc2 | 455c7e514e9006c3d833834608f066f0831239d02bb6f07df9e21e0c16c49095 | c1ccc(Nc2nc3ccccc3n2CCCNCC2CCCCC2)cc1 | O=[CH;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH2;D1;+0:6].[Cl;H0;D1;+0:7]-C-[Cl;H0;D1;+0:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:6]-[C:5]-[C:4].[ClH;D0;+0:7].[ClH;D0;+0:8] | null | [] | null | null | null | null | A solution of 2-[(4-acetylphenyl)amino]-N,N-bis(3-methylbutyl)-1-(3-oxopropyl)-1H-benzimidazole-6-carboxamide (100 mg, 1 eq) and aminomethylcyclohexane (46 mg, 2 eq) is stirred for 4 hours at a temperature of approximately 20° C. The mixture is diluted with methanol (1 ml), then sodium triacetoxyborohydride (86 mg, 2 e... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccc2[nH]cnc2c1.C1CCCCC1 | Other | C(C)(=O)O.O.CO | null | null | CC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCC=O)cc1.ClCCl.NCC1CCCCC1>C(C)(=O)O.O.CO>CC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCCNCC2CCCCC2)cc1.Cl.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eb9cb91b266942fbad15c7a7196198ab | COC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCCNC(=O)OC(C)(C)C)cc1>>CC(C)CCN(CCC(C)C)C(=O)c1ccc2nc(Nc3ccc(C(=O)O)cc3)n(CCCNC(=O)OC(C)(C)C)c2c1 | [OH-].[Li+].CC(CCN(C(=O)C=1C=CC2=C(N(C(=N2)NC2=CC=C(C(=O)OC)C=C2)CCCNC(=O)OC(C)(C)C)C1)CCC(C)C)C>>CC(CCN(C(=O)C=1C=CC2=C(N(C(=N2)NC2=CC=C(C(=O)O)C=C2)CCCNC(=O)OC(C)(C)C)C1)CCC(C)C)C | C[O:27][C:25]([c:24]1[cH:23][cH:22][c:21]([NH:20][c:19]2[n:18][c:17]3[cH:16][cH:15][c:14]([C:12]([N:6]([CH2:5][CH2:4][CH:2]([CH3:1])[CH3:3])[CH2:7][CH2:8][CH:9]([CH3:10])[CH3:11])=[O:13])[cH:43][c:42]3[n:30]2[CH2:31][CH2:32][CH2:33][NH:34][C:35](=[O:36])[O:37][C:38]([CH3:39])([CH3:40])[CH3:41])[cH:29][cH:28]1)=[O:26]>>... | COC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCCNC(=O)OC(C)(C)C)cc1 | CC(C)CCN(CCC(C)C)C(=O)c1ccc2nc(Nc3ccc(C(=O)O)cc3)n(CCCNC(=O)OC(C)(C)C)c2c1 | null | null | O1CCCC1.O.C(C)OCC | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Nc2nc3ccccc3[nH]2)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] | 79 | [{"value": 79.0, "product": "CC(CCN(C(=O)C=1C=CC2=C(N(C(=N2)NC2=CC=C(C(=O)O)C=C2)CCCNC(=O)OC(C)(C)C)C1)CCC(C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Lithium hydroxide (141 mg, 5 eq) is added to methyl 4-[(6-{[bis(3-methylbutyl)amino]carbonyl}-1-{3-[(tert-butoxycarbonyl)amino]propyl}-1H-benzimidazol-2-yl)amino]benzoate prepared according to reaction diagram A, Example A1, (405 mg, 1 eq) in a mixture of tetrahydrofuran (4 ml) and water (3 ml). The mixture is heated u... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2[nH]cnc2c1.c1ccccc1 | Other | O1CCCC1.O.C(C)OCC | null | null | COC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCCNC(=O)OC(C)(C)C)cc1>O1CCCC1.O.C(C)OCC>CC(C)CCN(CCC(C)C)C(=O)c1ccc2nc(Nc3ccc(C(=O)O)cc3)n(CCCNC(=O)OC(C)(C)C)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-945288725eb04bb0bf87d19f90cc58a7 | CC(C)CCN(CCC(C)C)C(=O)c1ccc2nc(Nc3ccc(C(=O)O)cc3)n(CCCNC(=O)OC(C)(C)C)c2c1.CN.Cl>>CNC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCCN)cc1.Cl | Cl.CN(CCCN=C=NCC)C.ON1N=NC2=C1C=CC=C2.CC(CCN(C(=O)C=1C=CC2=C(N(C(=N2)NC2=CC=C(C(=O)O)C=C2)CCCNC(=O)OC(C)(C)C)C1)CCC(C)C)C.Cl.CN>>Cl.Cl.NCCCN1C(=NC2=C1C=C(C=C2)C(=O)N(CCC(C)C)CCC(C)C)NC2=CC=C(C=C2)C(=O)NC | CC(C)(C)OC(=O)[NH:35][CH2:34][CH2:33][CH2:32][n:31]1[c:10]([NH:9][c:8]2[cH:7][cH:6][c:5]([C:3](O)=[O:4])[cH:37][cH:36]2)[n:11][c:12]2[cH:13][cH:14][c:15]([C:16](=[O:17])[N:18]([CH2:19][CH2:20][CH:21]([CH3:22])[CH3:23])[CH2:24][CH2:25][CH:26]([CH3:27])[CH3:28])[cH:29][c:30]21.[CH3:1][NH2:2].[ClH:39]>>[CH3:1][NH:2][C:3](... | CC(C)CCN(CCC(C)C)C(=O)c1ccc2nc(Nc3ccc(C(=O)O)cc3)n(CCCNC(=O)OC(C)(C)C)c2c1.CN.Cl | CNC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCCN)cc1.Cl | null | null | C(C)(=O)OCC.C(Cl)(Cl)Cl.ClCCl.O1CCCC1.C1CCOC1 | Acylation | OtherReaction | b4c20342f55b434660078663f02be082076e2ff9b9068db91acc0b381022a32e | e525bb030a9f5f4a2fc47bce923bf921a3769ce3300b3fa2600575194671a3f3 | c1ccc(Nc2nc3ccccc3[nH]2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3].O-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6](:[c:7]):[c:8].[C;D1;H3:9]-[NH2;D1;+0:10]>>[C;D1;H3:9]-[NH;D2;+0:10]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6](:[c:7]):[c:8].[C:3]-[C:2]-[NH2;D1;+0:1] | 106.6 | [{"value": 60.0, "product": "Cl.Cl.NCCCN1C(=NC2=C1C=C(C=C2)C(=O)N(CCC(C)C)CCC(C)C)NC2=CC=C(C=C2)C(=O)NC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 106.6, "product": "Cl.Cl.NCCCN1C(=NC2=C1C=C(C=C2)C(=O)N(CCC(C)C)CCC(C)C)NC2=CC=C(C=C2)C(=O)NC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 1 | HOUR | A solution of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (18 mg, 1.1 eq) in chloroform (1 ml) and a solution of 1-hydroxybenzotriazole (HOBt) (13 mg, 1.1 eq) in tetrahydrofuran (1 ml) are successively added to 4-[(6-{[bis(3-methylbutyl)amino]carbonyl}-1-{3-[(tert-butoxycarbonyl)amino]propyl}-1H-b... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Primary amine.Boc | Secondary amide.Primary amine | null | null | c1ccccc1.c1ccc2[nH]cnc2c1 | HO- | C(C)(=O)OCC.C(Cl)(Cl)Cl.ClCCl.O1CCCC1.C1CCOC1 | 20 | 1 | CC(C)CCN(CCC(C)C)C(=O)c1ccc2nc(Nc3ccc(C(=O)O)cc3)n(CCCNC(=O)OC(C)(C)C)c2c1.CN.Cl>C(C)(=O)OCC.C(Cl)(Cl)Cl.ClCCl.O1CCCC1.C1CCOC1>CNC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCCN)cc1.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e8c40567d1ea4f2ea926a9fe37796534 | CC(C)CCN(CCC(C)C)C(=O)c1ccc(N)c(NCCCNC(=O)OC(C)(C)C)c1.O=[N+]([O-])c1ccc(N=C=S)cc1>>CC(C)CCN(CCC(C)C)C(=O)c1ccc2nc(Nc3ccc([N+](=O)[O-])cc3)n(CCCNC(=O)OC(C)(C)C)c2c1 | [N+](=O)([O-])C1=CC=C(C=C1)N=C=S.C(C)(C)(C)OC(NCCCNC1=C(C=CC(=C1)C(=O)N(CCC(C)C)CCC(C)C)N)=O>>CC(CCN(C(=O)C=1C=CC2=C(N(C(=N2)NC2=CC=C(C=C2)[N+](=O)[O-])CCCNC(OC(C)(C)C)=O)C1)CCC(C)C)C | [CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][N:6]([CH2:7][CH2:8][CH:9]([CH3:10])[CH3:11])[C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17]([NH2:18])[c:42]([NH:30][CH2:31][CH2:32][CH2:33][NH:34][C:35](=[O:36])[O:37][C:38]([CH3:39])([CH3:40])[CH3:41])[cH:43]1.S=[C:19]=[N:20][c:21]1[cH:22][cH:23][c:24]([N+:25](=[O:26])[O-:27])[cH:28][cH... | CC(C)CCN(CCC(C)C)C(=O)c1ccc(N)c(NCCCNC(=O)OC(C)(C)C)c1.O=[N+]([O-])c1ccc(N=C=S)cc1 | CC(C)CCN(CCC(C)C)C(=O)c1ccc2nc(Nc3ccc([N+](=O)[O-])cc3)n(CCCNC(=O)OC(C)(C)C)c2c1 | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | 4b3e260fa6094641dfa114b35f3471079a338332f41031b31ba4b7bb465b4139 | c2745d0d96944794048cb0a435469fb3c0efa689f6d5e8d4fd6447372cabc5f8 | c1ccc(Nc2nc3ccccc3[nH]2)cc1 | S=[C;H0;D2;+0:1]=[N;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11](-[NH2;D1;+0:12]):[c:13]>>[C:6]-[C:7]-[n;H0;D3;+0:8]1:[c:9](:[c:10]):[c:11](:[c:13]):[n;H0;D2;+0:12]:[c;H0;D3;+0:1]:1-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5] | 88 | [{"value": 88.0, "product": "CC(CCN(C(=O)C=1C=CC2=C(N(C(=N2)NC2=CC=C(C=C2)[N+](=O)[O-])CCCNC(OC(C)(C)C)=O)C1)CCC(C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-nitrophenyl isothiocyanate (305 mg, 1.5 eq) and N-methylcyclohexylcarbodiimide-N-methyl-polystyrene resin (acquired from Novabiochem; charge 1.9 mmol/g; 1.75 g, 3 eq) are successively added to a solution of tert-butyl-3-[(2-amino-5-{[bis(3-methylbutyl)amino]carbonyl}phenyl)amino]propylcarbamate prepared according to ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine.Isothiocyanate | Secondary amine | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1.c1ccccc1 | Other | O1CCCC1 | null | null | CC(C)CCN(CCC(C)C)C(=O)c1ccc(N)c(NCCCNC(=O)OC(C)(C)C)c1.O=[N+]([O-])c1ccc(N=C=S)cc1>O1CCCC1>CC(C)CCN(CCC(C)C)C(=O)c1ccc2nc(Nc3ccc([N+](=O)[O-])cc3)n(CCCNC(=O)OC(C)(C)C)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d9e1b833a7594cf48d317aff28221f26 | CC(C)CCN(CCC(C)C)C(=O)c1ccc2nc(Nc3ccc([N+](=O)[O-])cc3)n(CCCNC(=O)OC(C)(C)C)c2c1>>CC(C)CCN(CCC(C)C)C(=O)c1ccc2nc(Nc3ccc(N)cc3)n(CCCNC(=O)OC(C)(C)C)c2c1 | CC(CCN(C(=O)C=1C=CC2=C(N(C(=N2)NC2=CC=C(C=C2)[N+](=O)[O-])CCCNC(OC(C)(C)C)=O)C1)CCC(C)C)C>>NC1=CC=C(C=C1)NC1=NC2=C(N1CCCNC(OC(C)(C)C)=O)C=C(C=C2)C(=O)N(CCC(C)C)CCC(C)C | O=[N+:25]([O-])[c:24]1[cH:23][cH:22][c:21]([NH:20][c:19]2[n:18][c:17]3[cH:16][cH:15][c:14]([C:12]([N:6]([CH2:5][CH2:4][CH:2]([CH3:1])[CH3:3])[CH2:7][CH2:8][CH:9]([CH3:10])[CH3:11])=[O:13])[cH:41][c:40]3[n:28]2[CH2:29][CH2:30][CH2:31][NH:32][C:33](=[O:34])[O:35][C:36]([CH3:37])([CH3:38])[CH3:39])[cH:27][cH:26]1>>[CH3:1]... | CC(C)CCN(CCC(C)C)C(=O)c1ccc2nc(Nc3ccc([N+](=O)[O-])cc3)n(CCCNC(=O)OC(C)(C)C)c2c1 | CC(C)CCN(CCC(C)C)C(=O)c1ccc2nc(Nc3ccc(N)cc3)n(CCCNC(=O)OC(C)(C)C)c2c1 | null | [Pd] | C(C)(=O)OCC.CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(Nc2nc3ccccc3[nH]2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 87 | [{"value": 87.0, "product": "NC1=CC=C(C=C1)NC1=NC2=C(N1CCCNC(OC(C)(C)C)=O)C=C(C=C2)C(=O)N(CCC(C)C)CCC(C)C", "details": "PERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 15 | HOUR | Tert-butyl 3-{6-{[bis(3-methylbutyl)amino]carbonyl}-2-[(4-nitrophenyl)amino]-1H-benzimidazol-1-yl}propylcarbamate (580 mg) in solution in a mixture of ethyl acetate/methanol 3:1 (40 ml), and 10% palladium on carbon (58 mg) are introduced into an autoclave. After stirring for 15 hours under a hydrogen atmosphere (3 bar)... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2[nH]cnc2c1.c1ccccc1 | Other | [Pd].C(C)(=O)OCC.CO | 20 | 15 | CC(C)CCN(CCC(C)C)C(=O)c1ccc2nc(Nc3ccc([N+](=O)[O-])cc3)n(CCCNC(=O)OC(C)(C)C)c2c1>[Pd].C(C)(=O)OCC.CO>CC(C)CCN(CCC(C)C)C(=O)c1ccc2nc(Nc3ccc(N)cc3)n(CCCNC(=O)OC(C)(C)C)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e8b7f33682d344749e5faafab4a3ae4e | C1CCOC1.CCN(CC)CC>>CCN(C(C)C)C(C)C | C(C)N(CC)CC.ClCCl.O1CCCC1>>C(C)(C)N(CC)C(C)C | C1OC[CH2:9][CH2:5]1.[CH3:1][CH2:2][N:3]([CH2:4][CH3:6])[CH2:7][CH3:8]>>[CH3:1][CH2:2][N:3]([CH:4]([CH3:5])[CH3:6])[CH:7]([CH3:8])[CH3:9] | C1CCOC1.CCN(CC)CC | CCN(C(C)C)C(C)C | null | null | null | C-C Coupling | OtherReaction | f4c1d2f351d19986fdb53e5c3242a30777f8f4b37ce27cc541347a8a34a04c62 | a5693ad0ff37ba299a3384a72fcc8b66e16e2c53e1f48e2cc3e13008b4273e5a | null | C1-O-C-[CH2;D2;+0:1]-[CH2;D2;+0:2]-1.[C:3]-[#7:4](-[CH2;D2;+0:5]-[C;D1;H3:6])-[CH2;D2;+0:7]-[C;D1;H3:8]>>[C:3]-[#7:4](-[CH;D3;+0:5](-[C;D1;H3:6])-[CH3;D1;+0:2])-[CH;D3;+0:7](-[C;D1;H3:8])-[CH3;D1;+0:1] | null | [] | null | null | null | null | As described in diagram G, the derivative (26) can be alkylated in the presence of a strong base such as potassium tertbutylate, by an α-chloroester derivative, in an aprotic polar solvent such as dimethylformamide at a temperature of 0-20° C. for 0.5-2 hours, in order to produce compound (27). The derivative (27) can ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | null | C1CCOC1 | null | null | HO- | null | null | null | C1CCOC1.CCN(CC)CC>>CCN(C(C)C)C(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e1da31a0292b4552946a0d7a8d4f0a70 | CCOC(=O)C(C)Cl.O=[N+]([O-])c1ccccc1Cl>>CCOC(=O)C(C)c1ccc([N+](=O)[O-])c(Cl)c1 | ClC1=C(C=CC=C1)[N+](=O)[O-].ClC(C(=O)OCC)C.Cl.CC(C)(C)[O-].[K+]>>ClC=1C=C(C=CC1[N+](=O)[O-])C(C(=O)OCC)C | Cl[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH3:7].[cH:8]1[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[c:15]([Cl:16])[cH:17]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH3:7])[c:8]1[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[c:15]([Cl:16])[cH:17]1 | CCOC(=O)C(C)Cl.O=[N+]([O-])c1ccccc1Cl | CCOC(=O)C(C)c1ccc([N+](=O)[O-])c(Cl)c1 | null | null | CN(C)C=O.C(C)(=O)OCC | C-C Coupling | OtherReaction | 40ca321fe4047c56d3dec7ae738915164e802e06a6dc78b541aeb3597dd936df | ae23b78d8cc9afe1235c3056fa58900d3a27e232dc891dd767f4195ab4ddcbb6 | c1ccccc1 | Cl-[CH;D3;+0:1](-[C;D1;H3:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6].[c:7]:[c:8]:[cH;D2;+0:9]:[c:10]:[c:11]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:1](-[C;D1;H3:2])-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:8]:[c:7] | 64 | [{"value": 64.0, "product": "ClC=1C=C(C=CC1[N+](=O)[O-])C(C(=O)OCC)C", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | Potassium tert-butylate (11.22 g, 2 eq) is added to a solution of DMF (80 ml) cooled down to 0° C. A solution of 1-chloro-2-nitrobenzene (7.87 g, 1 eq) and ethyl 2-chloropropanoate (7 ml, 1.1 eq) is added dropwise over 45 minutes to the mixture whilst keeping the reaction temperature below 5° C. At the end of the addit... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ester | Ester | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | CN(C)C=O.C(C)(=O)OCC | 0 | null | CCOC(=O)C(C)Cl.O=[N+]([O-])c1ccccc1Cl>CN(C)C=O.C(C)(=O)OCC>CCOC(=O)C(C)c1ccc([N+](=O)[O-])c(Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2f46a242e6ff4a80b7af46d616394e43 | CCOC(=O)C(C)c1ccc([N+](=O)[O-])c(Cl)c1.CI>>CCOC(=O)C(C)(C)c1ccc([N+](=O)[O-])c(Cl)c1 | ClC=1C=C(C=CC1[N+](=O)[O-])C(C(=O)OCC)C.[H-].[Na+].C(O)([O-])=O.[Na+].CI>>ClC=1C=C(C=CC1[N+](=O)[O-])C(C(=O)OCC)(C)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH3:7])[c:9]1[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[c:16]([Cl:17])[cH:18]1.I[CH3:8]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH3:7])([CH3:8])[c:9]1[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[c:16]([Cl:17])[cH:18]1 | CCOC(=O)C(C)c1ccc([N+](=O)[O-])c(Cl)c1.CI | CCOC(=O)C(C)(C)c1ccc([N+](=O)[O-])c(Cl)c1 | null | null | O.CN(C)C=O.C(C)(=O)OCC | C-C Coupling | Methylation with MeI_tertiary | 4a52ebe9ffae5bdd307b0b4ac6a7069bc533ab8d42293ed2712c32b846010273 | 49d6f28766066d07dffbcc6f4da77792f6ba67b4de619800bad651525d6fe2e7 | c1ccccc1 | I-[CH3;D1;+0:1].[C:2]-[#8:3]-[C:4](=[O;D1;H0:5])-[CH;D3;+0:6](-[C;D1;H3:7])-[c:8](:[c:9]):[c:10]>>[C:2]-[#8:3]-[C:4](=[O;D1;H0:5])-[C;H0;D4;+0:6](-[C;D1;H3:7])(-[CH3;D1;+0:1])-[c:8](:[c:9]):[c:10] | 94 | [{"value": 94.0, "product": "ClC=1C=C(C=CC1[N+](=O)[O-])C(C(=O)OCC)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | A solution of ethyl 2-(3-chloro-4-nitrophenyl)propanoate (14.1 g) is added dropwise to a suspension of sodium hydride (60% in oil, 2.4 g, 1.1 eq) in DMF (15 ml), cooled down to 0° C. After stirring for 1 hour at this temperature, a solution of methyl iodide (3.72 ml, 1.1 eq) in DMF (40 ml) is added dropwise to the mixt... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | null | null | c1ccccc1 | HI | O.CN(C)C=O.C(C)(=O)OCC | 0 | 1 | CCOC(=O)C(C)c1ccc([N+](=O)[O-])c(Cl)c1.CI>O.CN(C)C=O.C(C)(=O)OCC>CCOC(=O)C(C)(C)c1ccc([N+](=O)[O-])c(Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0f97eae317ad40e49923b9a79730dad9 | CCOC(=O)C(C)(C)c1ccc([N+](=O)[O-])c(Cl)c1>>CC(C)(C(=O)O)c1ccc([N+](=O)[O-])c(Cl)c1 | [OH-].[K+].ClC=1C=C(C=CC1[N+](=O)[O-])C(C(=O)OCC)(C)C>>ClC=1C=C(C=CC1[N+](=O)[O-])C(C(=O)O)(C)C | CC[O:6][C:4]([C:2]([CH3:1])([CH3:3])[c:7]1[cH:8][cH:9][c:10]([N+:11](=[O:12])[O-:13])[c:14]([Cl:15])[cH:16]1)=[O:5]>>[CH3:1][C:2]([CH3:3])([C:4](=[O:5])[OH:6])[c:7]1[cH:8][cH:9][c:10]([N+:11](=[O:12])[O-:13])[c:14]([Cl:15])[cH:16]1 | CCOC(=O)C(C)(C)c1ccc([N+](=O)[O-])c(Cl)c1 | CC(C)(C(=O)O)c1ccc([N+](=O)[O-])c(Cl)c1 | null | null | CO | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 95 | [{"value": 95.0, "product": "ClC=1C=C(C=CC1[N+](=O)[O-])C(C(=O)O)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A 2N solution of potassium hydroxide (18 ml) is added at a temperature of approximately 20° C. to a solution of ethyl 2-(3-chloro-4-nitrophenyl)-2-methylpropanoate (1 g) in methanol (20 ml). The mixture is then heated at 80° C. for 1.5 hours then cooled down to ambient temperature. The methanol is evaporated by concent... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | CO | 80 | null | CCOC(=O)C(C)(C)c1ccc([N+](=O)[O-])c(Cl)c1>CO>CC(C)(C(=O)O)c1ccc([N+](=O)[O-])c(Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5af5511bc1d9402bae148a2a45a6c9f8 | CC(C)(C(=O)O)c1ccc([N+](=O)[O-])c(Cl)c1.CC(C)CNCC(C)C>>CC(C)CN(CC(C)C)C(=O)C(C)(C)c1ccc([N+](=O)[O-])c(Cl)c1 | S(=O)(Cl)Cl.ClC=1C=C(C=CC1[N+](=O)[O-])C(C(=O)O)(C)C.C(C)(C)N(CC)C(C)C.C(C(C)C)NCC(C)C>>ClC=1C=C(C=CC1[N+](=O)[O-])C(C(=O)N(CC(C)C)CC(C)C)(C)C | O[C:10](=[O:11])[C:12]([CH3:13])([CH3:14])[c:15]1[cH:16][cH:17][c:18]([N+:19](=[O:20])[O-:21])[c:22]([Cl:23])[cH:24]1.[CH3:1][CH:2]([CH3:3])[CH2:4][NH:5][CH2:6][CH:7]([CH3:8])[CH3:9]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]([CH2:6][CH:7]([CH3:8])[CH3:9])[C:10](=[O:11])[C:12]([CH3:13])([CH3:14])[c:15]1[cH:16][cH:17][c:18]([N... | CC(C)(C(=O)O)c1ccc([N+](=O)[O-])c(Cl)c1.CC(C)CNCC(C)C | CC(C)CN(CC(C)C)C(=O)C(C)(C)c1ccc([N+](=O)[O-])c(Cl)c1 | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[c:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[C:10]-[C:11])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[c:6] | 82 | [{"value": 82.0, "product": "ClC=1C=C(C=CC1[N+](=O)[O-])C(C(=O)N(CC(C)C)CC(C)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Thionyl chloride (0.54 ml, 4 eq) is added to a solution of 2-(3-chloro-4-nitrophenyl)-2-methylpropanoic acid (500 mg) in dichloromethane (1 ml). The mixture is heated under reflux for 16 hours then cooled down to ambient temperature. The solvent is evaporated off under reduced pressure at 40° C. (co-evaporation with to... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccccc1 | HO- | ClCCl | null | 3 | CC(C)(C(=O)O)c1ccc([N+](=O)[O-])c(Cl)c1.CC(C)CNCC(C)C>ClCCl>CC(C)CN(CC(C)C)C(=O)C(C)(C)c1ccc([N+](=O)[O-])c(Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-59f0064c8ebf419f84b5dee79e3f33b1 | CC(C)CN(CC(C)C)C(=O)C(C)(C)c1ccc([N+](=O)[O-])c(Cl)c1.CN(C)CCCN>>CC(C)CN(CC(C)C)C(=O)C(C)(C)c1ccc([N+](=O)[O-])c(NCCCN(C)C)c1 | ClC=1C=C(C=CC1[N+](=O)[O-])C(C(=O)N(CC(C)C)CC(C)C)(C)C.CN(CCCN)C.C([O-])([O-])=O.[K+].[K+]>>CN(CCCNC=1C=C(C=CC1[N+](=O)[O-])C(C(=O)N(CC(C)C)CC(C)C)(C)C)C | Cl[c:22]1[c:18]([N+:19](=[O:20])[O-:21])[cH:17][cH:16][c:15]([C:12]([C:10]([N:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[CH2:6][CH:7]([CH3:8])[CH3:9])=[O:11])([CH3:13])[CH3:14])[cH:30]1.[NH2:23][CH2:24][CH2:25][CH2:26][N:27]([CH3:28])[CH3:29]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]([CH2:6][CH:7]([CH3:8])[CH3:9])[C:10](=[O:11])[C:12... | CC(C)CN(CC(C)C)C(=O)C(C)(C)c1ccc([N+](=O)[O-])c(Cl)c1.CN(C)CCCN | CC(C)CN(CC(C)C)C(=O)C(C)(C)c1ccc([N+](=O)[O-])c(NCCCN(C)C)c1 | null | null | O.CN(C)C=O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccccc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[c:2]:[c:3] | 48 | [{"value": 48.0, "product": "CN(CCCNC=1C=C(C=CC1[N+](=O)[O-])C(C(=O)N(CC(C)C)CC(C)C)(C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-(3-chloro-4-nitrophenyl)-N,N-diisobutyl-2-methylpropanamide (78 mg, 1 eq), 3-dimethylaminopropylamine (45 mg, 2 eq) and potassium carbonate (62 mg, 2 eq) in DMF (2 ml) is heated under reflux for 3 hours then cooled down to ambient temperature. The residue is taken up in ethyl acetate (20 ml) and water (8... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | O.CN(C)C=O.C(C)(=O)OCC | null | null | CC(C)CN(CC(C)C)C(=O)C(C)(C)c1ccc([N+](=O)[O-])c(Cl)c1.CN(C)CCCN>O.CN(C)C=O.C(C)(=O)OCC>CC(C)CN(CC(C)C)C(=O)C(C)(C)c1ccc([N+](=O)[O-])c(NCCCN(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f7ba90e45e934de19c3c93de15db6255 | CC(C)CN(CC(C)C)C(=O)C(C)(C)c1ccc([N+](=O)[O-])c(NCCCN(C)C)c1>>CC(C)CN(CC(C)C)C(=O)C(C)(C)c1ccc(N)c(NCCCN(C)C)c1 | CN(CCCNC=1C=C(C=CC1[N+](=O)[O-])C(C(=O)N(CC(C)C)CC(C)C)(C)C)C>>NC1=C(C=C(C=C1)C(C(=O)N(CC(C)C)CC(C)C)(C)C)NCCCN(C)C | O=[N+:19]([O-])[c:18]1[cH:17][cH:16][c:15]([C:12]([C:10]([N:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[CH2:6][CH:7]([CH3:8])[CH3:9])=[O:11])([CH3:13])[CH3:14])[cH:28][c:20]1[NH:21][CH2:22][CH2:23][CH2:24][N:25]([CH3:26])[CH3:27]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]([CH2:6][CH:7]([CH3:8])[CH3:9])[C:10](=[O:11])[C:12]([CH3:13])([C... | CC(C)CN(CC(C)C)C(=O)C(C)(C)c1ccc([N+](=O)[O-])c(NCCCN(C)C)c1 | CC(C)CN(CC(C)C)C(=O)C(C)(C)c1ccc(N)c(NCCCN(C)C)c1 | null | [Pd] | C(C)(=O)OCC.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] | 95 | [{"value": 95.0, "product": "NC1=C(C=C(C=C1)C(C(=O)N(CC(C)C)CC(C)C)(C)C)NCCCN(C)C", "details": "PERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 4 | HOUR | 2-(3-{[3-(dimethylamino)propyl]amino}-4-nitrophenyl)-N,N-diisobutyl-2-methylpropanamide (44 mg) in solution in a mixture of ethyl acetate/ethanol 2:1 (3 ml), and 10% palladium on carbon (5 mg) are introduced into an autoclave. After stirring for 4 hours under a hydrogen atmosphere (3 bar) at a temperature of approximat... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Pd].C(C)(=O)OCC.C(C)O | 20 | 4 | CC(C)CN(CC(C)C)C(=O)C(C)(C)c1ccc([N+](=O)[O-])c(NCCCN(C)C)c1>[Pd].C(C)(=O)OCC.C(C)O>CC(C)CN(CC(C)C)C(=O)C(C)(C)c1ccc(N)c(NCCCN(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2a548b80b3df4b579cdecb96da60aa24 | Cc1ccc([N+](=O)[O-])c(F)c1.[O]=[Mn](=[O])(=[O])[O-]>>O=C(O)c1ccc([N+](=O)[O-])c(F)c1 | FC=1C=C(C=CC1[N+](=O)[O-])C.[Mn](=O)(=O)(=O)[O-].[K+].O>>FC=1C=C(C(=O)O)C=CC1[N+](=O)[O-] | [CH3:2][c:4]1[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[c:11]([F:12])[cH:13]1.[O]=[Mn](=[O])(=[O:1])[O-:3]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[c:11]([F:12])[cH:13]1 | Cc1ccc([N+](=O)[O-])c(F)c1.[O]=[Mn](=[O])(=[O])[O-] | O=C(O)c1ccc([N+](=O)[O-])c(F)c1 | null | null | null | Acylation | OtherReaction | 7769a4cd09a67e270ac2d1d32df6b7a59b468ff590f9c59723b72ba3c8deb342 | 903e48d04e4504a4fe6977f5e5582144adff237d0488a4542a1907161cf0134c | c1ccccc1 | [CH3;D1;+0:1]-[c:2](:[c:3]):[c:4].[O-;H0;D1:5]-[Mn](=[O;H0;D1;+0:6])(=[O])=[O]>>[O;H0;D1;+0:6]=[C;H0;D3;+0:1](-[OH;D1;+0:5])-[c:2](:[c:3]):[c:4] | 58 | [{"value": 58.0, "product": "FC=1C=C(C(=O)O)C=CC1[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-fluoro-4-nitrotoluene (10 g, 1 eq) and potassium permanganate (25.5 g, 2.5 eq) in water (1 L) is heated under reflux for 6 hours then cooled down to ambient temperature. The mixture is filtered on celite and the aqueous phase is washed twice with diethyl ether (2×300 ml). The aqueous phase is acidified, ... | 10.6084/m9.figshare.5104873.v1 | null | null | Carboxylic acid | null | null | c1ccccc1 | HO- | null | null | null | Cc1ccc([N+](=O)[O-])c(F)c1.[O]=[Mn](=[O])(=[O])[O-]>>O=C(O)c1ccc([N+](=O)[O-])c(F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-43d0fa93096142ada92f9e97e64044c8 | CC(C)CCNCCC(C)C.O=C(O)c1ccc([N+](=O)[O-])c(F)c1>>CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(F)c1 | C(CC(C)C)NCCC(C)C.Cl.CN(CCCN=C=NCC)C.ON1N=NC2=C1C=CC=C2.FC=1C=C(C(=O)O)C=CC1[N+](=O)[O-]>>FC=1C=C(C(=O)N(CCC(C)C)CCC(C)C)C=CC1[N+](=O)[O-] | [CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][NH:6][CH2:7][CH2:8][CH:9]([CH3:10])[CH3:11].O[C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20])[c:21]([F:22])[cH:23]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][N:6]([CH2:7][CH2:8][CH:9]([CH3:10])[CH3:11])[C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17]([N+:18](=[O:19])[O-:20]... | CC(C)CCNCCC(C)C.O=C(O)c1ccc([N+](=O)[O-])c(F)c1 | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(F)c1 | null | null | C(Cl)(Cl)Cl.C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[C:9]-[C:10])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 65 | [{"value": 65.0, "product": "FC=1C=C(C(=O)N(CCC(C)C)CCC(C)C)C=CC1[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 1 | HOUR | 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (4.4 g, 1.1 eq) in solution in chloroform (25 ml) and 1-hydroxybenzotriazole (HOBt) (3.05 g, 1.1 eq) in solution in THF (40 ml) are added successively to 3-fluoro-4-nitrobenzoic acid (3.8 g, 1 eq) in solution in anhydrous THF (30 ml). The mixture is stir... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccccc1 | HO- | C(Cl)(Cl)Cl.C1CCOC1 | 20 | 1 | CC(C)CCNCCC(C)C.O=C(O)c1ccc([N+](=O)[O-])c(F)c1>C(Cl)(Cl)Cl.C1CCOC1>CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-38eb5f54a0d64a3aa3aa1ffb2c8dfec8 | CC(C)(C)OC(=O)NCCCN.CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(F)c1>>CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(NCCCNC(=O)OC(C)(C)C)c1 | FC=1C=C(C(=O)N(CCC(C)C)CCC(C)C)C=CC1[N+](=O)[O-].C(=O)(OC(C)(C)C)NCCCN.C([O-])([O-])=O.[K+].[K+]>>CC(CCN(C(=O)C=1C=CC(=C(C1)NCCCNC(OC(C)(C)C)=O)[N+](=O)[O-])CCC(C)C)C | [NH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33].F[c:21]1[c:17]([N+:18](=[O:19])[O-:20])[cH:16][cH:15][c:14]([C:12]([N:6]([CH2:5][CH2:4][CH:2]([CH3:1])[CH3:3])[CH2:7][CH2:8][CH:9]([CH3:10])[CH3:11])=[O:13])[cH:34]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][N:6]([CH2:7][CH2:8][C... | CC(C)(C)OC(=O)NCCCN.CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(F)c1 | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(NCCCNC(=O)OC(C)(C)C)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](-[#7:5])=[O;D1;H0:6]):[c:7](-[#7;+:8]):[c:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[#7:5]-[C:4](=[O;D1;H0:6])-[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:12]-[C:11]-[C:10]):[c:7](-[#7;+:8]):[c:9] | 96 | [{"value": 96.0, "product": "CC(CCN(C(=O)C=1C=CC(=C(C1)NCCCNC(OC(C)(C)C)=O)[N+](=O)[O-])CCC(C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-fluoro-N,N-bis(3-methylbutyl)-4-nitrobenzamide (1.6 g, 1 eq), N-Boc-1,3-diaminopropane (0.9 g, 1.2 eq) and potassium carbonate (1.35 g, 2 eq) in acetonitrile (80 ml) is heated under reflux for 5 hours then concentrated under reduced pressure at 40° C. The residue is taken up in dichloromethane (100 ml) a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | C(C)#N | null | null | CC(C)(C)OC(=O)NCCCN.CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(F)c1>C(C)#N>CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(NCCCNC(=O)OC(C)(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1b53811f221247c1bb159882d41fbb18 | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(NCCCNC(=O)OC(C)(C)C)c1>>CC(C)CCN(CCC(C)C)C(=O)c1ccc(N)c(NCCCNC(=O)OC(C)(C)C)c1 | CC(CCN(C(=O)C=1C=CC(=C(C1)NCCCNC(OC(C)(C)C)=O)[N+](=O)[O-])CCC(C)C)C>>NC1=C(C=C(C=C1)C(=O)N(CCC(C)C)CCC(C)C)NCCCNC(OC(C)(C)C)=O | O=[N+:18]([O-])[c:17]1[cH:16][cH:15][c:14]([C:12]([N:6]([CH2:5][CH2:4][CH:2]([CH3:1])[CH3:3])[CH2:7][CH2:8][CH:9]([CH3:10])[CH3:11])=[O:13])[cH:32][c:19]1[NH:20][CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31]>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][N:6]([CH2:7][CH2:8][CH:9]([CH3:10]... | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(NCCCNC(=O)OC(C)(C)C)c1 | CC(C)CCN(CCC(C)C)C(=O)c1ccc(N)c(NCCCNC(=O)OC(C)(C)C)c1 | null | [Pd] | C(C)(=O)OCC.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] | 89 | [{"value": 89.0, "product": "NC1=C(C=C(C=C1)C(=O)N(CCC(C)C)CCC(C)C)NCCCNC(OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 3 | HOUR | Tert-butyl 3-[(5-{[bis(3-methylbutyl)amino]carbonyl}-2-nitrophenyl)amino]propylcarbamate (1.65 g) in solution in a mixture of ethyl acetate/ethanol 2:1 (130 ml), and 10% palladium on carbon (165 mg) are introduced into an autoclave. After stirring for 3 hours under a hydrogen atmosphere (3 bar) at a temperature of appr... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Pd].C(C)(=O)OCC.C(C)O | 20 | 3 | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(NCCCNC(=O)OC(C)(C)C)c1>[Pd].C(C)(=O)OCC.C(C)O>CC(C)CCN(CCC(C)C)C(=O)c1ccc(N)c(NCCCNC(=O)OC(C)(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9b536f278ba74500adca0b757b0a4ac4 | CC(C)CCN(CCC(C)C)C(=O)c1ccc(N)c(NCCCNC(=O)OC(C)(C)C)c1.COC(=O)c1ccc(N=C=S)cc1>>COC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCCNC(=O)OC(C)(C)C)cc1 | COC(=O)C1=CC=C(C=C1)N=C=S.C(C)(C)(C)OC(NCCCNC1=C(C=CC(=C1)C(=O)N(CCC(C)C)CCC(C)C)N)=O>>CC(CCN(C(=O)C=1C=CC2=C(N(C(=N2)NC2=CC=C(C(=O)OC)C=C2)CCCNC(=O)OC(C)(C)C)C1)CCC(C)C)C | [NH2:11][c:12]1[cH:13][cH:14][c:15]([C:16](=[O:17])[N:18]([CH2:19][CH2:20][CH:21]([CH3:22])[CH3:23])[CH2:24][CH2:25][CH:26]([CH3:27])[CH3:28])[cH:29][c:30]1[NH:31][CH2:32][CH2:33][CH2:34][NH:35][C:36](=[O:37])[O:38][C:39]([CH3:40])([CH3:41])[CH3:42].S=[C:10]=[N:9][c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:44... | CC(C)CCN(CCC(C)C)C(=O)c1ccc(N)c(NCCCNC(=O)OC(C)(C)C)c1.COC(=O)c1ccc(N=C=S)cc1 | COC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCCNC(=O)OC(C)(C)C)cc1 | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | 4b3e260fa6094641dfa114b35f3471079a338332f41031b31ba4b7bb465b4139 | c2745d0d96944794048cb0a435469fb3c0efa689f6d5e8d4fd6447372cabc5f8 | c1ccc(Nc2nc3ccccc3[nH]2)cc1 | S=[C;H0;D2;+0:1]=[N;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11](-[NH2;D1;+0:12]):[c:13]>>[C:6]-[C:7]-[n;H0;D3;+0:8]1:[c:9](:[c:10]):[c:11](:[c:13]):[n;H0;D2;+0:12]:[c;H0;D3;+0:1]:1-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5] | 60 | [{"value": 60.0, "product": "CC(CCN(C(=O)C=1C=CC2=C(N(C(=N2)NC2=CC=C(C(=O)OC)C=C2)CCCNC(=O)OC(C)(C)C)C1)CCC(C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | 4-methoxycarbonylphenyl isothiocyanate (327 mg, 1.5 eq) and N-methylcyclohexylcarbodiimide-N-methyl-polystyrene resin (acquired from Novabiochem; charge 1.9 mmol/g; 1.75 g, 3 eq) are added successively to a solution of tert-butyl-3-[(2-amino-5-{[bis(3-methylbutyl)amino]carbonyl}phenyl)amino]propylcarbamate (500 mg, 1 e... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine.Isothiocyanate | Secondary amine | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccccc1.c1ccc2[nH]cnc2c1 | Other | O1CCCC1 | null | 4 | CC(C)CCN(CCC(C)C)C(=O)c1ccc(N)c(NCCCNC(=O)OC(C)(C)C)c1.COC(=O)c1ccc(N=C=S)cc1>O1CCCC1>COC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCCNC(=O)OC(C)(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-af338b6ea7a84e98bda4f867f5c8755b | COC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCCNC(=O)OC(C)(C)C)cc1>>COC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCCN)cc1.Cl | Cl.CC(CCN(C(=O)C=1C=CC2=C(N(C(=N2)NC2=CC=C(C(=O)OC)C=C2)CCCNC(=O)OC(C)(C)C)C1)CCC(C)C)C>>Cl.Cl.NCCCN1C(=NC2=C1C=C(C=C2)C(=O)N(CCC(C)C)CCC(C)C)NC2=CC=C(C(=O)OC)C=C2 | CC(C)(C)OC(=O)[NH:35][CH2:34][CH2:33][CH2:32][n:31]1[c:10]([NH:9][c:8]2[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:37][cH:36]2)[n:11][c:12]2[cH:13][cH:14][c:15]([C:16](=[O:17])[N:18]([CH2:19][CH2:20][CH:21]([CH3:22])[CH3:23])[CH2:24][CH2:25][CH:26]([CH3:27])[CH3:28])[cH:29][c:30]21>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[... | COC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCCNC(=O)OC(C)(C)C)cc1 | COC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCCN)cc1.Cl | null | null | O1CCOCC1.C(C)(=O)OCC | Miscellaneous | Hydrogenolysis of amides/imides/carbamates | 4812e39fa209f57a5a2564677791e5e37790c829f5742d8c7df33806c5ba4ce0 | d7ecc2e7a68b8c20d378ac6004c3fdfc3efd09bbbd9efd577186f69427135737 | c1ccc(Nc2nc3ccccc3[nH]2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | 96 | [{"value": 96.0, "product": "Cl.Cl.NCCCN1C(=NC2=C1C=C(C=C2)C(=O)N(CCC(C)C)CCC(C)C)NC2=CC=C(C(=O)OC)C=C2", "details": "PERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 1 | HOUR | A solution of hydrochloric acid in dioxane (4N, 2 ml) is added to a solution of methyl 4-[(6-{[bis(3-methylbutyl)amino]carbonyl}-1-{3-[(tert-butoxycarbonyl)amino]propyl}-1H-benzimidazol-2-yl)amino]benzoate (180 mg) in ethyl acetate (2 ml). After stirring for 1 hour at a temperature of approximately 20° C., the mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ccc2[nH]cnc2c1 | HO- | O1CCOCC1.C(C)(=O)OCC | 20 | 1 | COC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCCNC(=O)OC(C)(C)C)cc1>O1CCOCC1.C(C)(=O)OCC>COC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCCN)cc1.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aa7fbbc0b74e41e08e72af0a129ce3ec | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(F)c1.NCCCN1CCCCC1>>CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(NCCCN2CCCCC2)c1 | FC=1C=C(C(=O)N(CCC(C)C)CCC(C)C)C=CC1[N+](=O)[O-].N1(CCCCC1)CCCN.C([O-])([O-])=O.[K+].[K+]>>CC(CCN(C(C1=CC(=C(C=C1)[N+](=O)[O-])NCCCN1CCCCC1)=O)CCC(C)C)C | F[c:21]1[c:17]([N+:18](=[O:19])[O-:20])[cH:16][cH:15][c:14]([C:12]([N:6]([CH2:5][CH2:4][CH:2]([CH3:1])[CH3:3])[CH2:7][CH2:8][CH:9]([CH3:10])[CH3:11])=[O:13])[cH:32]1.[NH2:22][CH2:23][CH2:24][CH2:25][N:26]1[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][N:6]([CH2:7][CH2:8][CH:9]([CH3:10])... | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(F)c1.NCCCN1CCCCC1 | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(NCCCN2CCCCC2)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(NCCCN2CCCCC2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](-[#7:5])=[O;D1;H0:6]):[c:7](-[#7;+:8]):[c:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[#7:5]-[C:4](=[O;D1;H0:6])-[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:12]-[C:11]-[C:10]):[c:7](-[#7;+:8]):[c:9] | 78 | [{"value": 78.0, "product": "CC(CCN(C(C1=CC(=C(C=C1)[N+](=O)[O-])NCCCN1CCCCC1)=O)CCC(C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-fluoro-N,N-bis(3-methylbutyl)-4-nitrobenzamide (430 mg, 1 eq, prepared according to Example A1), 3-piperidino-propylamine (212 mg, 1.1 eq) and potassium carbonate (365 mg, 2 eq) in acetonitrile (10 ml) is heated under reflux for 3 hours then concentrated under reduced pressure at 40° C. The residue is ta... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CC[NH]CC1 | HF | C(C)#N | null | null | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(F)c1.NCCCN1CCCCC1>C(C)#N>CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(NCCCN2CCCCC2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-77870a5cb73b458091e3a2a4e28b418f | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(F)c1.CCN(CC)CCCN>>CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(NCCCN(C)C)c1 | FC=1C=C(C(=O)N(CCC(C)C)CCC(C)C)C=CC1[N+](=O)[O-].C(C)N(CCCN)CC.C([O-])([O-])=O.[K+].[K+]>>CN(CCCNC=1C=C(C(=O)N(CCC(C)C)CCC(C)C)C=CC1[N+](=O)[O-])C | F[c:21]1[c:17]([N+:18](=[O:19])[O-:20])[cH:16][cH:15][c:14]([C:12]([N:6]([CH2:5][CH2:4][CH:2]([CH3:1])[CH3:3])[CH2:7][CH2:8][CH:9]([CH3:10])[CH3:11])=[O:13])[cH:29]1.C[CH2:27][N:26]([CH2:25][CH2:24][CH2:23][NH2:22])[CH2:28]C>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][N:6]([CH2:7][CH2:8][CH:9]([CH3:10])[CH3:11])[C:12](=[O:13... | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(F)c1.CCN(CC)CCCN | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(NCCCN(C)C)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccccc1 | C-[CH2;D2;+0:1]-[#7:2](-[C:3]-[C:4]-[C:5]-[NH2;D1;+0:6])-[CH2;D2;+0:7]-C.F-[c;H0;D3;+0:8](:[c:9]:[c:10]-[C:11](-[#7:12])=[O;D1;H0:13]):[c:14](-[#7;+:15]):[c:16]>>[#7:12]-[C:11](=[O;D1;H0:13])-[c:10]:[c:9]:[c;H0;D3;+0:8](-[NH;D2;+0:6]-[C:5]-[C:4]-[C:3]-[#7:2](-[CH3;D1;+0:1])-[CH3;D1;+0:7]):[c:14](-[#7;+:15]):[c:16] | 68 | [{"value": 68.0, "product": "CN(CCCNC=1C=C(C(=O)N(CCC(C)C)CCC(C)C)C=CC1[N+](=O)[O-])C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-fluoro-N,N-bis(3-methylbutyl)-4-nitrobenzamide (2.5 g, 1 eq, prepared according to Example A1), 3-diethylamino-propylamine (877 mg, 1.1 eq) and potassium carbonate (2.13 g, 2 eq) in acetonitrile (80 ml) is heated under reflux for 5 hours then concentrated under reduced pressure at 40° C. The residue is t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | C(C)#N | null | null | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(F)c1.CCN(CC)CCCN>C(C)#N>CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(NCCCN(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bbfc9ae511c84bba8eda624ccf6a6a0a | CC(C)(C)OC(=O)Nc1ccc(N)cc1.CON>>CONC(=O)Nc1ccc(NC(=O)OC(C)(C)C)cc1 | Cl.CON.C(O)([O-])=O.[Na+].C(=O)(C=1NC=CN1)C=1NC=CN1.NC1=CC=C(C=C1)NC(OC(C)(C)C)=O.C(C)N(CC)CC>>CONC(=O)NC1=CC=C(C=C1)NC(OC(C)(C)C)=O | [NH2:6][c:7]1[cH:8][cH:9][c:10]([NH:11][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[cH:19][cH:20]1.[CH3:1][O:2][NH2:3]>>[CH3:1][O:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][cH:9][c:10]([NH:11][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[cH:19][cH:20]1 | CC(C)(C)OC(=O)Nc1ccc(N)cc1.CON | CONC(=O)Nc1ccc(NC(=O)OC(C)(C)C)cc1 | null | null | ClCCl.O.C(Cl)(Cl)Cl | Acylation | OtherReaction | 0803607fba0d95b5aa54f50a0ea365a82edda165361e01ad9e7ff57568bb8df0 | 4ff96020857e85930fbee987c7fa4ef615e45b2ea39cff27ceaec8f9174d5b6f | c1ccccc1 | [C;D1;H3:1]-[#8:2]-[NH2;D1;+0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:1]-[#8:2]-[NH;D2;+0:3]-[C:8](=[O;D1;H0:9])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 94.7 | [{"value": 94.7, "product": "CONC(=O)NC1=CC=C(C=C1)NC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 15 | HOUR | Carbonyl-di-imidazole (1.62 g, 2 eq) is added to a solution cooled down to 0° C., of tert-butyl 4-aminophenylcarbamate (1.04 g) in anhydrous dichloromethane (100 ml). The mixture is taken to a temperature of 20° C. and is stirred at this temperature for 15 hours. Triethylamine (7 ml, 10 eq) followed by O-methylhydroxyl... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine | Urea | null | null | c1ccccc1 | Other | ClCCl.O.C(Cl)(Cl)Cl | 0 | 15 | CC(C)(C)OC(=O)Nc1ccc(N)cc1.CON>ClCCl.O.C(Cl)(Cl)Cl>CONC(=O)Nc1ccc(NC(=O)OC(C)(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-95374fdb77d4406c9c89a46824690303 | CONC(=O)Nc1ccc(N)cc1.S=C(Cl)Cl>>CONC(=O)Nc1ccc(N=C=S)cc1 | Cl.NC1=CC=C(C=C1)NC(=O)NOC.C(C)N(CC)CC.C(=S)(Cl)Cl.O>>N(=C=S)C1=CC=C(C=C1)NC(=O)NOC | [CH3:1][O:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][cH:9][c:10]([NH2:11])[cH:14][cH:15]1.Cl[C:12](Cl)=[S:13]>>[CH3:1][O:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][cH:9][c:10]([N:11]=[C:12]=[S:13])[cH:14][cH:15]1 | CONC(=O)Nc1ccc(N)cc1.S=C(Cl)Cl | CONC(=O)Nc1ccc(N=C=S)cc1 | null | null | O1CCCC1.C(C)OCC | Heteroatom Alkylation and Arylation | Amine and thiophosgene to isothiocyanate | 1226380c52141f79542a4f85564c11e38ca245efc80be1557b635219a638388c | e5752ca9983a57ab07a0b76a5c8a57a6667ab2cd460616b960134623ec0fce31 | c1ccccc1 | Cl-[C;H0;D3;+0:1](-Cl)=[S;D1;H0:2].[NH2;D1;+0:3]-[c:4](:[c:5]):[c:6]>>[S;D1;H0:2]=[C;H0;D2;+0:1]=[N;H0;D2;+0:3]-[c:4](:[c:5]):[c:6] | 62 | [{"value": 62.0, "product": "N(=C=S)C1=CC=C(C=C1)NC(=O)NOC", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 15 | MINUTE | Thiophosgene (0.38 ml, 1.1 eq) is added dropwise to a solution cooled down to 0° C., of N-(4-aminophenyl)-N′-methoxyurea hydrochloride (1 g) and triethylamine (3.2 ml, 5 eq) in tetrahydrofuran (90 ml). The mixture is stirred for 15 min at 0° C. then water and diethyl ether are added. After decantation and extractions, ... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Alkenyl halide.Primary amine | Isothiocyanate | null | null | c1ccccc1 | HCl | O1CCCC1.C(C)OCC | 0 | 0.25 | CONC(=O)Nc1ccc(N)cc1.S=C(Cl)Cl>O1CCCC1.C(C)OCC>CONC(=O)Nc1ccc(N=C=S)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-efb82e1de57f472ca65c6ad072d41877 | COC(=O)c1ccc(C(=O)Cl)cc1.N#C[S-]>>COC(=O)c1ccc(C(=O)N=C=S)cc1 | [S-]C#N.[K+].ClC(=O)C1=CC=C(C(=O)OC)C=C1>>N(=C=S)C(=O)C1=CC=C(C(=O)OC)C=C1 | Cl[C:9]([c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:15][cH:14]1)=[O:10].[N:11]#[C:12][S-:13]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[N:11]=[C:12]=[S:13])[cH:14][cH:15]1 | COC(=O)c1ccc(C(=O)Cl)cc1.N#C[S-] | COC(=O)c1ccc(C(=O)N=C=S)cc1 | null | null | C(C)#N | Acylation | OtherReaction | c7e68a1fa6ac27c3709bff81e45d4a7a4c0739b1f7c19440be50a653bd0f64cf | 424f8e293ba0b1403ae5b768e3028ff5c90d55f9a9629c56f4dcf4b5b2a529b7 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[N;H0;D1;+0:6]#[C;H0;D2;+0:7]-[S-;H0;D1:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D2;+0:6]=[C;H0;D2;+0:7]=[S;H0;D1;+0:8])-[c:3](:[c:4]):[c:5] | 95 | [{"value": 95.0, "product": "N(=C=S)C(=O)C1=CC=C(C(=O)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.3, "product": "N(=C=S)C(=O)C1=CC=C(C(=O)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 1 | HOUR | Potassium thiocyanate (1.08 g) is added to a solution of methyl 4-chlorocarbonylbenzoate (2 g) in acetonitrile (30 ml). After stirring for 1 hour at approximately 20° C., the mixture is filtered and the filtrate is concentrated under reduced pressure at 40° C. The solid obtained is purified by flash chromatography on s... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Nitrile | Isothiocyanate | null | null | c1ccccc1 | Other | C(C)#N | 20 | 1 | COC(=O)c1ccc(C(=O)Cl)cc1.N#C[S-]>C(C)#N>COC(=O)c1ccc(C(=O)N=C=S)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9ce81bb4aa734f1a91760dbecdba343c | C[Si](C)(C)C=[N+]=[N-].O=C(O)c1ccc([N+](=O)[O-])c(F)c1>>COC(=O)c1ccc([N+](=O)[O-])c(F)c1 | C[Si](C)(C)C=[N+]=[N-].FC=1C=C(C(=O)O)C=CC1[N+](=O)[O-]>>FC=1C=C(C(=O)OC)C=CC1[N+](=O)[O-] | C[Si](C)(C)[CH:1]=[N+]=[N-].[OH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[c:12]([F:13])[cH:14]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[c:12]([F:13])[cH:14]1 | C[Si](C)(C)C=[N+]=[N-].O=C(O)c1ccc([N+](=O)[O-])c(F)c1 | COC(=O)c1ccc([N+](=O)[O-])c(F)c1 | null | null | CO | Heteroatom Alkylation and Arylation | O-alkylation of carboxylic acids with diazo compounds | 39589be0e9a30df66714fe618d22a8ac0fb24901dbf2ead1ab33e31556c7ac64 | 8b539baf7aeb5ab868833e33306bad77200a853d562904197e13de2e27e229d7 | c1ccccc1 | C-[Si](-C)(-C)-[CH;D2;+0:1]=[N+]=[N-].[O;D1;H0:2]=[C:3](-[OH;D1;+0:4])-[c:5]>>[CH3;D1;+0:1]-[O;H0;D2;+0:4]-[C:3](=[O;D1;H0:2])-[c:5] | 87 | [{"value": 87.0, "product": "FC=1C=C(C(=O)OC)C=CC1[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of trimethylsilyldiazomethane (2M in hexane, 50 ml, 4 eq) is slowly added to a solution of 3-fluoro-4-nitrobenzoic acid (4.7 g, 1 eq) in methanol (70 ml) until the gas evolution ceases. The excess trimethylsilyldiazomethane is consumed by the dropwise addition of acetic acid until the solution becomes discol... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Diazo.Silyl protective group | Ester | null | null | c1ccccc1 | Other | CO | null | null | C[Si](C)(C)C=[N+]=[N-].O=C(O)c1ccc([N+](=O)[O-])c(F)c1>CO>COC(=O)c1ccc([N+](=O)[O-])c(F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-def1084f0c3b4f64b72985ba2b88a4e8 | CC(C)(C)OC(=O)NCCCN.COC(=O)c1ccc([N+](=O)[O-])c(F)c1>>COC(=O)c1ccc([N+](=O)[O-])c(NCCCNC(=O)OC(C)(C)C)c1 | FC=1C=C(C(=O)OC)C=CC1[N+](=O)[O-].C(=O)(OC(C)(C)C)NCCCN.C([O-])([O-])=O.[K+].[K+]>>C(C)(C)(C)OC(=O)NCCCNC=1C=C(C(=O)OC)C=CC1[N+](=O)[O-] | [NH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24].F[c:12]1[c:8]([N+:9](=[O:10])[O-:11])[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:25]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[c:12]([NH:13][CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:19])[O... | CC(C)(C)OC(=O)NCCCN.COC(=O)c1ccc([N+](=O)[O-])c(F)c1 | COC(=O)c1ccc([N+](=O)[O-])c(NCCCNC(=O)OC(C)(C)C)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](-[#8:5])=[O;D1;H0:6]):[c:7](-[#7;+:8]):[c:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[#7;+:8]-[c:7](:[c:9]):[c;H0;D3;+0:1](-[NH;D2;+0:12]-[C:11]-[C:10]):[c:2]:[c:3]-[C:4](-[#8:5])=[O;D1;H0:6] | 99 | [{"value": 99.0, "product": "C(C)(C)(C)OC(=O)NCCCNC=1C=C(C(=O)OC)C=CC1[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of methyl 3-fluoro-4-nitrobenzoate (5.8 g, 1 eq), N-Boc-1,3-diaminopropane (5.75 g, 1.1 eq) and potassium carbonate (8.04 g, 2 eq) in acetonitrile (200 ml) is heated under reflux for 2 hours then concentrated under reduced pressure at 40° C. The residue is taken up in dichloromethane (200 ml) and water (100 m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | C(C)#N | null | null | CC(C)(C)OC(=O)NCCCN.COC(=O)c1ccc([N+](=O)[O-])c(F)c1>C(C)#N>COC(=O)c1ccc([N+](=O)[O-])c(NCCCNC(=O)OC(C)(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-738362d4b1254d849c6196150c37dc39 | COC(=O)c1ccc([N+](=O)[O-])c(NCCCNC(=O)OC(C)(C)C)c1>>COC(=O)c1ccc(N)c(NCCCNC(=O)OC(C)(C)C)c1 | C(C)(C)(C)OC(=O)NCCCNC=1C=C(C(=O)OC)C=CC1[N+](=O)[O-]>>NC1=C(C=C(C(=O)OC)C=C1)NCCCNC(=O)OC(C)(C)C | O=[N+:9]([O-])[c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:23][c:10]1[NH:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[c:10]([NH:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21... | COC(=O)c1ccc([N+](=O)[O-])c(NCCCNC(=O)OC(C)(C)C)c1 | COC(=O)c1ccc(N)c(NCCCNC(=O)OC(C)(C)C)c1 | null | [Pd] | C(C)(=O)OCC.CO | 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] | 83 | [{"value": 83.0, "product": "NC1=C(C=C(C(=O)OC)C=C1)NCCCNC(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 4 | HOUR | Methyl 3-({3-[(tert-butoxycarbonyl)amino]propyl}amino)-4-nitrobenzoate (10.2 g) in solution in a mixture of ethyl acetate/methanol 3:1 (300 ml), and 10% palladium on carbon (1.02 g) are introduced into an autoclave. After stirring for 4 hours under a hydrogen atmosphere (3 bar) at a temperature of approximately 20° C.,... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Pd].C(C)(=O)OCC.CO | 20 | 4 | COC(=O)c1ccc([N+](=O)[O-])c(NCCCNC(=O)OC(C)(C)C)c1>[Pd].C(C)(=O)OCC.CO>COC(=O)c1ccc(N)c(NCCCNC(=O)OC(C)(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-42067fc6e84247f4918deb5357125a06 | COC(=O)c1ccc(N)c(NCCCNC(=O)OC(C)(C)C)c1.COc1cc(N=C=S)cc(OC)c1OC>>COC(=O)c1ccc2nc(Nc3cc(OC)c(OC)c(OC)c3)n(CCCNC(=O)OC(C)(C)C)c2c1 | COC=1C=C(C=C(C1OC)OC)N=C=S.C(C)(C)N=C=NC(C)C.NC1=C(C=C(C(=O)OC)C=C1)NCCCNC(=O)OC(C)(C)C>>C(C)(C)(C)OC(=O)NCCCN1C(=NC2=C1C=C(C=C2)C(=O)OC)NC2=CC(=C(C(=C2)OC)OC)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[c:36]([NH:24][CH2:25][CH2:26][CH2:27][NH:28][C:29](=[O:30])[O:31][C:32]([CH3:33])([CH3:34])[CH3:35])[cH:37]1.S=[C:10]=[N:11][c:12]1[cH:13][c:14]([O:15][CH3:16])[c:17]([O:18][CH3:19])[c:20]([O:21][CH3:22])[cH:23]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]... | COC(=O)c1ccc(N)c(NCCCNC(=O)OC(C)(C)C)c1.COc1cc(N=C=S)cc(OC)c1OC | COC(=O)c1ccc2nc(Nc3cc(OC)c(OC)c(OC)c3)n(CCCNC(=O)OC(C)(C)C)c2c1 | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | 4b3e260fa6094641dfa114b35f3471079a338332f41031b31ba4b7bb465b4139 | c2745d0d96944794048cb0a435469fb3c0efa689f6d5e8d4fd6447372cabc5f8 | c1ccc(Nc2nc3ccccc3[nH]2)cc1 | S=[C;H0;D2;+0:1]=[N;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11](-[NH2;D1;+0:12]):[c:13]>>[C:6]-[C:7]-[n;H0;D3;+0:8]1:[c:9](:[c:10]):[c:11](:[c:13]):[n;H0;D2;+0:12]:[c;H0;D3;+0:1]:1-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5] | 36 | [{"value": 36.0, "product": "C(C)(C)(C)OC(=O)NCCCN1C(=NC2=C1C=C(C=C2)C(=O)OC)NC2=CC(=C(C(=C2)OC)OC)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 3,4,5-trimethoxyphenyl isothiocyanate (6.6 g, 1.2 eq) and diisopropylcarbodiimide (9.1 g, 3 eq) are successively added to a solution of methyl 4-amino-3-({3-[(tert-butoxycarbonyl)amino]propyl}amino)benzoate (7.75 g, 1 eq) in tetrahydrofuran (130 ml). The mixture is heated under reflux for 16 hours then cooled down to a... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine.Isothiocyanate | Secondary amine | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1.c1ccccc1 | Other | O1CCCC1 | null | null | COC(=O)c1ccc(N)c(NCCCNC(=O)OC(C)(C)C)c1.COc1cc(N=C=S)cc(OC)c1OC>O1CCCC1>COC(=O)c1ccc2nc(Nc3cc(OC)c(OC)c(OC)c3)n(CCCNC(=O)OC(C)(C)C)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f0068efb9ed942a5b8e5833afdaf3f83 | COC(=O)c1ccc2nc(Nc3cc(OC)c(OC)c(OC)c3)n(CCCNC(=O)OC(C)(C)C)c2c1>>COc1cc(Nc2nc3ccc(C(=O)O)cc3n2CCCNC(=O)OC(C)(C)C)cc(OC)c1OC | [OH-].[Li+].C(C)(C)(C)OC(=O)NCCCN1C(=NC2=C1C=C(C=C2)C(=O)OC)NC2=CC(=C(C(=C2)OC)OC)OC>>C(C)(C)(C)OC(=O)NCCCN1C(=NC2=C1C=C(C=C2)C(=O)O)NC2=CC(=C(C(=C2)OC)OC)OC | C[O:15][C:13]([c:12]1[cH:11][cH:10][c:9]2[n:8][c:7]([NH:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:34]([O:35][CH3:36])[c:31]([O:32][CH3:33])[cH:30]3)[n:18]([CH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[c:17]2[cH:16]1)=[O:14]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[n:8][c:9]3[cH:10... | COC(=O)c1ccc2nc(Nc3cc(OC)c(OC)c(OC)c3)n(CCCNC(=O)OC(C)(C)C)c2c1 | COc1cc(Nc2nc3ccc(C(=O)O)cc3n2CCCNC(=O)OC(C)(C)C)cc(OC)c1OC | null | null | O1CCCC1.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Nc2nc3ccccc3[nH]2)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] | null | [] | null | null | null | null | Lithium hydroxide (2.18 g, 6 eq) is added to a solution of methyl 1-{3-[(tert-butoxycarbonyl)amino]propyl}-2-[(3,4,5-trimethoxyphenyl)amino]-1H-benzimidazole-6-carboxylate (4.4 g, 1 eq) in a mixture of tetrahydrofuran (40 ml) and water (30 ml). The mixture is heated under reflux for 18 hours then cooled down to ambient... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccc2[nH]cnc2c1 | Other | O1CCCC1.O | null | null | COC(=O)c1ccc2nc(Nc3cc(OC)c(OC)c(OC)c3)n(CCCNC(=O)OC(C)(C)C)c2c1>O1CCCC1.O>COc1cc(Nc2nc3ccc(C(=O)O)cc3n2CCCNC(=O)OC(C)(C)C)cc(OC)c1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2ad6c828d4044c0f9d1af4755a0e3721 | C1CCNCC1.COc1cc(Nc2nc3ccc(C(=O)O)cc3n2CCCNC(=O)OC(C)(C)C)cc(OC)c1OC>>COc1cc(Nc2nc3ccc(C(=O)N4CCCCC4)cc3n2CCCN)cc(OC)c1OC.Cl | N1CCCCC1.Cl.C(=O)(N1C=NC=C1)N1C=NC=C1.C(C)(C)(C)OC(=O)NCCCN1C(=NC2=C1C=C(C=C2)C(=O)O)NC2=CC(=C(C(=C2)OC)OC)OC>>Cl.Cl.NCCCN1C(=NC2=C1C=C(C=C2)C(=O)N2CCCCC2)NC2=CC(=C(C(=C2)OC)OC)OC | [NH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1.CC(C)(C)OC(=O)[NH:27][CH2:26][CH2:25][CH2:24][n:23]1[c:7]([NH:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:32]([O:33][CH3:34])[c:29]([O:30][CH3:31])[cH:28]2)[n:8][c:9]2[cH:10][cH:11][c:12]([C:13](O)=[O:14])[cH:21][c:22]21>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[n:8][c:9]3[cH... | C1CCNCC1.COc1cc(Nc2nc3ccc(C(=O)O)cc3n2CCCNC(=O)OC(C)(C)C)cc(OC)c1OC | COc1cc(Nc2nc3ccc(C(=O)N4CCCCC4)cc3n2CCCN)cc(OC)c1OC.Cl | null | null | ClCCl.C(C)(=O)OCC.C(Cl)(Cl)Cl.O1CCCC1.CN(C=O)C | Acylation | OtherReaction | 4f8ccca95d869c8d3dcac786a435dba99d995a07df815bae744f7a819bbe3617 | 9cd01fe9ee5cb03a85922f937adad468b1a7e7d55c326a442ab91fc46e4b1c78 | O=C(c1ccc2nc(Nc3ccccc3)[nH]c2c1)N1CCCCC1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3].O-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6](:[c:7]):[c:8]:[c:9]:[#7;a:10].[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]>>[#7;a:10]:[c:9]:[c:8]:[c:6](-[C;H0;D3;+0:4](=[O;D1;H0:5])-[N;H0;D3;+0:13](-[C:12]-[C:11])-[C:14]-[C:15]):[c:7].[C:3]-[C:2]-[NH2;D1;+0:1] | 65 | [{"value": 65.0, "product": "Cl.Cl.NCCCN1C(=NC2=C1C=C(C=C2)C(=O)N2CCCCC2)NC2=CC(=C(C(=C2)OC)OC)OC", "details": "PERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 16 | HOUR | A solution of carbonyldiimidazole (CDI) (18 mg, 1.1 eq) in chloroform (0.2 ml) is added to a solution of 1-{3-[(tert-butoxycarbonyl)amino]propyl}-2-[(3,4,5-trimethoxyphenyl)amino]-1H-benzimidazole-6-carboxylic acid (50 mg, 1 eq) in tetrahydrofuran (0.45 ml) and dimethylformamide (0.05 ml). The mixture is stirred for 16... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Secondary amine.Boc | Tertiary amide.Primary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.c1ccc2[nH]cnc2c1.C1CC[NH]CC1 | HO- | ClCCl.C(C)(=O)OCC.C(Cl)(Cl)Cl.O1CCCC1.CN(C=O)C | 20 | 16 | C1CCNCC1.COc1cc(Nc2nc3ccc(C(=O)O)cc3n2CCCNC(=O)OC(C)(C)C)cc(OC)c1OC>ClCCl.C(C)(=O)OCC.C(Cl)(Cl)Cl.O1CCCC1.CN(C=O)C>COc1cc(Nc2nc3ccc(C(=O)N4CCCCC4)cc3n2CCCN)cc(OC)c1OC.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-049292afe56345638c2bf9e2e857b4f2 | CC(C)(C)C=O.COc1cc(Nc2nc3ccc(C(=O)N(CC(C)C)CC(C)C)cc3n2CCCN)cc(OC)c1OC.ClCCl.ClCCl>>COc1cc(Nc2nc3ccc(C(=O)N(CC(C)C)CC(C)C)cc3n2CCCNCC(C)(C)C)cc(OC)c1OC.Cl.Cl | NCCCN1C(=NC2=C1C=C(C=C2)C(=O)N(CC(C)C)CC(C)C)NC2=CC(=C(C(=C2)OC)OC)OC.CC(C=O)(C)C.ClCCl.C(O)([O-])=O.[Na+].ClCCl.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>Cl.Cl.C(C(C)C)N(C(=O)C=1C=CC2=C(N(C(=N2)NC2=CC(=C(C(=C2)OC)OC)OC)CCCNCC(C)(C)C)C1)CC(C)C | O=[CH:31][C:32]([CH3:33])([CH3:34])[CH3:35].[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[n:8][c:9]3[cH:10][cH:11][c:12]([C:13](=[O:14])[N:15]([CH2:16][CH:17]([CH3:18])[CH3:19])[CH2:20][CH:21]([CH3:22])[CH3:23])[cH:24][c:25]3[n:26]2[CH2:27][CH2:28][CH2:29][NH2:30])[cH:36][c:37]([O:38][CH3:39])[c:40]1[O:41][CH3:42].ClC[Cl:... | CC(C)(C)C=O.COc1cc(Nc2nc3ccc(C(=O)N(CC(C)C)CC(C)C)cc3n2CCCN)cc(OC)c1OC.ClCCl.ClCCl | COc1cc(Nc2nc3ccc(C(=O)N(CC(C)C)CC(C)C)cc3n2CCCNCC(C)(C)C)cc(OC)c1OC.Cl.Cl | null | null | O.CO | Heteroatom Alkylation and Arylation | OtherReaction | 016c9849d927236ad312c4a1ada4bb312217ef63df13cd653676c1c8436029c1 | a6638cc6afd7e4d9005f7b96ad12e3d567dce3969c1c4003fb4b0c32cc0506ba | c1ccc(Nc2nc3ccccc3[nH]2)cc1 | Cl-C-[Cl;H0;D1;+0:1].Cl-C-[Cl;H0;D1;+0:2].O=[CH;D2;+0:3]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[C:8]-[C:9]-[NH2;D1;+0:10]>>[C:8]-[C:9]-[NH;D2;+0:10]-[CH2;D2;+0:3]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[ClH;D0;+0:1].[ClH;D0;+0:2] | null | [] | null | null | null | null | A solution of 1-(3-aminopropyl)-N,N-diisobutyl-2-[(3,4,5-trimethoxyphenyl)amino]-1H-benzimidazole-6-carboxamide (100 mg, 1 eq) and trimethylacetaldehyde (25 mg, 1.5 eq) in dichloromethane (1 ml) is stirred for 4 hours at a temperature of approximately 20° C. The mixture is diluted with methanol (1 ml) then sodium triac... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Primary halide.Primary halide.Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccc2[nH]cnc2c1 | HCl | O.CO | null | null | CC(C)(C)C=O.COc1cc(Nc2nc3ccc(C(=O)N(CC(C)C)CC(C)C)cc3n2CCCN)cc(OC)c1OC.ClCCl.ClCCl>O.CO>COc1cc(Nc2nc3ccc(C(=O)N(CC(C)C)CC(C)C)cc3n2CCCNCC(C)(C)C)cc(OC)c1OC.Cl.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-68f011eb7d1a4559999ee8341aa65466 | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(F)c1.NCCC1OCCO1>>CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(NCCC2OCCO2)c1 | C([O-])([O-])=O.[K+].[K+].FC=1C=C(C(=O)N(CCC(C)C)CCC(C)C)C=CC1[N+](=O)[O-].NCCC1OCCO1>>O1C(OCC1)CCNC=1C=C(C(=O)N(CCC(C)C)CCC(C)C)C=CC1[N+](=O)[O-] | F[c:21]1[c:17]([N+:18](=[O:19])[O-:20])[cH:16][cH:15][c:14]([C:12]([N:6]([CH2:5][CH2:4][CH:2]([CH3:1])[CH3:3])[CH2:7][CH2:8][CH:9]([CH3:10])[CH3:11])=[O:13])[cH:30]1.[NH2:22][CH2:23][CH2:24][CH:25]1[O:26][CH2:27][CH2:28][O:29]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][N:6]([CH2:7][CH2:8][CH:9]([CH3:10])[CH3:11])[C:12](=[O... | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(F)c1.NCCC1OCCO1 | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(NCCC2OCCO2)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(NCCC2OCCO2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](-[#7:5])=[O;D1;H0:6]):[c:7](-[#7;+:8]):[c:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[#7:5]-[C:4](=[O;D1;H0:6])-[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:12]-[C:11]-[C:10]):[c:7](-[#7;+:8]):[c:9] | 98 | [{"value": 98.0, "product": "O1C(OCC1)CCNC=1C=C(C(=O)N(CCC(C)C)CCC(C)C)C=CC1[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-fluoro-N,N-bis(3-methylbutyl)-4-nitrobenzamide prepared according to Example A1 (1.86 g, 1 eq), 2-(2-aminoethyl)-1,3-dioxolane (0.8 g, 1.2 eq) and potassium carbonate (1.58 g, 2 eq) in acetonitrile (150 ml) is heated under reflux for 3 hours then concentrated under reduced pressure at 40° C. The residue ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.C1COCO1 | HF | C(C)#N | null | null | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(F)c1.NCCC1OCCO1>C(C)#N>CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(NCCC2OCCO2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-58db6ddf78ff4261a60c1722e3a80ef6 | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(NCCC2OCCO2)c1>>CC(C)CCN(CCC(C)C)C(=O)c1ccc(N)c(NCCC2OCCO2)c1 | O1C(OCC1)CCNC=1C=C(C(=O)N(CCC(C)C)CCC(C)C)C=CC1[N+](=O)[O-]>>NC1=C(C=C(C(=O)N(CCC(C)C)CCC(C)C)C=C1)NCCC1OCCO1 | O=[N+:18]([O-])[c:17]1[cH:16][cH:15][c:14]([C:12]([N:6]([CH2:5][CH2:4][CH:2]([CH3:1])[CH3:3])[CH2:7][CH2:8][CH:9]([CH3:10])[CH3:11])=[O:13])[cH:28][c:19]1[NH:20][CH2:21][CH2:22][CH:23]1[O:24][CH2:25][CH2:26][O:27]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][N:6]([CH2:7][CH2:8][CH:9]([CH3:10])[CH3:11])[C:12](=[O:13])[c:14]1[... | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(NCCC2OCCO2)c1 | CC(C)CCN(CCC(C)C)C(=O)c1ccc(N)c(NCCC2OCCO2)c1 | null | [Pd] | C(C)(=O)OCC.CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(NCCC2OCCO2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 89 | [{"value": 89.0, "product": "NC1=C(C=C(C(=O)N(CCC(C)C)CCC(C)C)C=C1)NCCC1OCCO1", "details": "PERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 4 | HOUR | 3-{[2-(1,3-dioxolan-2-yl)ethyl]amino}-N,N-bis(3-methylbutyl)-4-nitrobenzamide (2.4 g) in solution in a mixture of ethyl acetate/methanol 2:1 (100 ml), and 10% palladium on carbon (240 mg) are introduced into an autoclave. After stirring for 4 hours under a hydrogen atmosphere (3 bar) at a temperature of approximately 2... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.C1COCO1 | Other | [Pd].C(C)(=O)OCC.CO | 20 | 4 | CC(C)CCN(CCC(C)C)C(=O)c1ccc([N+](=O)[O-])c(NCCC2OCCO2)c1>[Pd].C(C)(=O)OCC.CO>CC(C)CCN(CCC(C)C)C(=O)c1ccc(N)c(NCCC2OCCO2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5d98e5e0bf7c435689749e9524e0a37d | CC(=O)c1ccc(N=C=S)cc1.CC(C)CCN(CCC(C)C)C(=O)c1ccc(N)c(NCCC2OCCO2)c1>>CC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCC2OCCO2)cc1 | C(C)(=O)C1=CC=C(C=C1)N=C=S.C(C)(C)N=C=NC(C)C.NC1=C(C=C(C(=O)N(CCC(C)C)CCC(C)C)C=C1)NCCC1OCCO1>>C(C)(=O)C1=CC=C(C=C1)NC1=NC2=C(N1CCC1OCCO1)C=C(C=C2)C(=O)N(CCC(C)C)CCC(C)C | S=[C:9]=[N:8][c:7]1[cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:39][cH:38]1.[NH2:10][c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[N:17]([CH2:18][CH2:19][CH:20]([CH3:21])[CH3:22])[CH2:23][CH2:24][CH:25]([CH3:26])[CH3:27])[cH:28][c:29]1[NH:30][CH2:31][CH2:32][CH:33]1[O:34][CH2:35][CH2:36][O:37]1>>[CH3:1][C:2](=[O:3])[c:4]1[c... | CC(=O)c1ccc(N=C=S)cc1.CC(C)CCN(CCC(C)C)C(=O)c1ccc(N)c(NCCC2OCCO2)c1 | CC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCC2OCCO2)cc1 | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | 4b3e260fa6094641dfa114b35f3471079a338332f41031b31ba4b7bb465b4139 | c2745d0d96944794048cb0a435469fb3c0efa689f6d5e8d4fd6447372cabc5f8 | c1ccc(Nc2nc3ccccc3n2CCC2OCCO2)cc1 | S=[C;H0;D2;+0:1]=[N;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11](-[NH2;D1;+0:12]):[c:13]>>[C:6]-[C:7]-[n;H0;D3;+0:8]1:[c:9](:[c:10]):[c:11](:[c:13]):[n;H0;D2;+0:12]:[c;H0;D3;+0:1]:1-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5] | 66 | [{"value": 66.0, "product": "C(C)(=O)C1=CC=C(C=C1)NC1=NC2=C(N1CCC1OCCO1)C=C(C=C2)C(=O)N(CCC(C)C)CCC(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-acetylphenyl isothiocyanate (1.1 g, 1.2 eq) and diisopropylcarbodiimide (1.95 g, 3 eq) are successively added to a solution of 4-amino-3-{[2-(1,3-dioxolan-2-yl)ethyl]amino}-N,N-bis(3-methylbutyl)benzamide (2 g, 1 eq) in tetrahydrofuran (50 ml). The mixture is heated under reflux for 18 hours then cooled down to ambie... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine.Isothiocyanate | Secondary amine | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccccc1.c1ccc2[nH]cnc2c1.C1COCO1 | Other | O1CCCC1 | null | null | CC(=O)c1ccc(N=C=S)cc1.CC(C)CCN(CCC(C)C)C(=O)c1ccc(N)c(NCCC2OCCO2)c1>O1CCCC1>CC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCC2OCCO2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ea252ab4b008481b8b31d7f3cb2bdcdc | CC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCC2OCCO2)cc1>>CC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCC=O)cc1 | C(C)(=O)C1=CC=C(C=C1)NC1=NC2=C(N1CCC1OCCO1)C=C(C=C2)C(=O)N(CCC(C)C)CCC(C)C.Cl>>C(C)(=O)C1=CC=C(C=C1)NC1=NC2=C(N1CCC=O)C=C(C=C2)C(=O)N(CCC(C)C)CCC(C)C | C1C[O:34][CH:33]([CH2:32][CH2:31][n:30]2[c:9]([NH:8][c:7]3[cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:36][cH:35]3)[n:10][c:11]3[cH:12][cH:13][c:14]([C:15](=[O:16])[N:17]([CH2:18][CH2:19][CH:20]([CH3:21])[CH3:22])[CH2:23][CH2:24][CH:25]([CH3:26])[CH3:27])[cH:28][c:29]32)O1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([NH... | CC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCC2OCCO2)cc1 | CC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCC=O)cc1 | null | null | O1CCCC1 | Miscellaneous | Acetal hydrolysis to aldehyde | f12636b09f9df336ccc8fe82b927db0e267bccc7cae0970f1f91c7ceed085225 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | c1ccc(Nc2nc3ccccc3[nH]2)cc1 | [C:1]-[C:2]-[CH;D3;+0:3]1-O-C-C-[O;H0;D2;+0:4]-1>>[C:1]-[C:2]-[CH;D2;+0:3]=[O;H0;D1;+0:4] | 99 | [{"value": 99.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 18 | HOUR | A solution of 2-[(4-acetylphenyl)amino]-1-[2-(1,3-dioxolan-2-yl)ethyl]-N,N-bis(3-methylbutyl)-1H-benzimidazole-6-carboxamide (900 mg) in a mixture of tetrahydrofuran (30 ml) and aqueous hydrochloric acid (3N, 40 ml) is stirred for 18 hours at a temperature of approximately 20° C. then concentrated under reduced pressur... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | C1COCO1 | null | c1ccccc1.c1ccc2[nH]cnc2c1 | HO- | O1CCCC1 | 20 | 18 | CC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCC2OCCO2)cc1>O1CCCC1>CC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCC=O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-947037de2df54a8593e4cba4f7f65a17 | CC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCC=O)cc1.ClCCl.NCC1CCCCC1>>CC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCCNCC2CCCCC2)cc1.Cl.Cl | C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+].C(O)([O-])=O.[Na+].ClCCl.C(C)(=O)C1=CC=C(C=C1)NC1=NC2=C(N1CCC=O)C=C(C=C2)C(=O)N(CCC(C)C)CCC(C)C.NCC1CCCCC1>>Cl.Cl.C(C)(=O)C1=CC=C(C=C1)NC1=NC2=C(N1CCCNCC1CCCCC1)C=C(C=C2)C(=O)N(CCC(C)C)CCC(C)C | O=[CH:33][CH2:32][CH2:31][n:30]1[c:9]([NH:8][c:7]2[cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:43][cH:42]2)[n:10][c:11]2[cH:12][cH:13][c:14]([C:15](=[O:16])[N:17]([CH2:18][CH2:19][CH:20]([CH3:21])[CH3:22])[CH2:23][CH2:24][CH:25]([CH3:26])[CH3:27])[cH:28][c:29]21.C([Cl:44])[Cl:45].[NH2:34][CH2:35][CH:36]1[CH2:37][CH2:38][... | CC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCC=O)cc1.ClCCl.NCC1CCCCC1 | CC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCCNCC2CCCCC2)cc1.Cl.Cl | null | C(C)(=O)O | O.CO | Heteroatom Alkylation and Arylation | OtherReaction | 05249243ec4191ae0a34b72c1c53354c09eacc7795ccf55b263c625934998bc2 | 455c7e514e9006c3d833834608f066f0831239d02bb6f07df9e21e0c16c49095 | c1ccc(Nc2nc3ccccc3n2CCCNCC2CCCCC2)cc1 | O=[CH;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH2;D1;+0:6].[Cl;H0;D1;+0:7]-C-[Cl;H0;D1;+0:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:6]-[C:5]-[C:4].[ClH;D0;+0:7].[ClH;D0;+0:8] | null | [] | null | null | null | null | A solution of 2-[(4-acetylphenyl)amino]-N,N-bis(3-methylbutyl)-1-(3-oxopropyl)-1H-benzimidazole-6-carboxamide (100 mg, 1 eq) and aminomethylcyclohexane (46 mg, 2 eq) is stirred for 4 hours at a temperature of approximately 20° C. The mixture is diluted with methanol (1 ml), then sodium triacetoxyborohydride (86 mg, 2 e... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccc2[nH]cnc2c1.C1CCCCC1 | Other | C(C)(=O)O.O.CO | null | null | CC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCC=O)cc1.ClCCl.NCC1CCCCC1>C(C)(=O)O.O.CO>CC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCCNCC2CCCCC2)cc1.Cl.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ff5fd7c600514d0a90e36840d81a472a | COC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCCNC(=O)OC(C)(C)C)cc1>>CC(C)CCN(CCC(C)C)C(=O)c1ccc2nc(Nc3ccc(C(=O)O)cc3)n(CCCNC(=O)OC(C)(C)C)c2c1 | [OH-].[Li+].CC(CCN(C(=O)C=1C=CC2=C(N(C(=N2)NC2=CC=C(C(=O)OC)C=C2)CCCNC(=O)OC(C)(C)C)C1)CCC(C)C)C>>CC(CCN(C(=O)C=1C=CC2=C(N(C(=N2)NC2=CC=C(C(=O)O)C=C2)CCCNC(=O)OC(C)(C)C)C1)CCC(C)C)C | C[O:27][C:25]([c:24]1[cH:23][cH:22][c:21]([NH:20][c:19]2[n:18][c:17]3[cH:16][cH:15][c:14]([C:12]([N:6]([CH2:5][CH2:4][CH:2]([CH3:1])[CH3:3])[CH2:7][CH2:8][CH:9]([CH3:10])[CH3:11])=[O:13])[cH:43][c:42]3[n:30]2[CH2:31][CH2:32][CH2:33][NH:34][C:35](=[O:36])[O:37][C:38]([CH3:39])([CH3:40])[CH3:41])[cH:29][cH:28]1)=[O:26]>>... | COC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCCNC(=O)OC(C)(C)C)cc1 | CC(C)CCN(CCC(C)C)C(=O)c1ccc2nc(Nc3ccc(C(=O)O)cc3)n(CCCNC(=O)OC(C)(C)C)c2c1 | null | null | O1CCCC1.O.C(C)OCC | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Nc2nc3ccccc3[nH]2)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] | 79 | [{"value": 79.0, "product": "CC(CCN(C(=O)C=1C=CC2=C(N(C(=N2)NC2=CC=C(C(=O)O)C=C2)CCCNC(=O)OC(C)(C)C)C1)CCC(C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Lithium hydroxide (141 mg, 5 eq) is added to methyl 4-[(6-{[bis(3-methylbutyl)amino]carbonyl}-1-{3-[(tert-butoxycarbonyl)amino]propyl}-1H-benzimidazol-2-yl)amino]benzoate prepared according to reaction diagram A, Example A1, (405 mg, 1 eq) in a mixture of tetrahydrofuran (4 ml) and water (3 ml). The mixture is heated u... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2[nH]cnc2c1.c1ccccc1 | Other | O1CCCC1.O.C(C)OCC | null | null | COC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCCNC(=O)OC(C)(C)C)cc1>O1CCCC1.O.C(C)OCC>CC(C)CCN(CCC(C)C)C(=O)c1ccc2nc(Nc3ccc(C(=O)O)cc3)n(CCCNC(=O)OC(C)(C)C)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7af147ecacb040298f209ac3bdca986c | CC(C)CCN(CCC(C)C)C(=O)c1ccc2nc(Nc3ccc(C(=O)O)cc3)n(CCCNC(=O)OC(C)(C)C)c2c1.CN.Cl>>CNC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCCN)cc1.Cl | Cl.CN(CCCN=C=NCC)C.ON1N=NC2=C1C=CC=C2.CC(CCN(C(=O)C=1C=CC2=C(N(C(=N2)NC2=CC=C(C(=O)O)C=C2)CCCNC(=O)OC(C)(C)C)C1)CCC(C)C)C.Cl.CN>>Cl.Cl.NCCCN1C(=NC2=C1C=C(C=C2)C(=O)N(CCC(C)C)CCC(C)C)NC2=CC=C(C=C2)C(=O)NC | CC(C)(C)OC(=O)[NH:35][CH2:34][CH2:33][CH2:32][n:31]1[c:10]([NH:9][c:8]2[cH:7][cH:6][c:5]([C:3](O)=[O:4])[cH:37][cH:36]2)[n:11][c:12]2[cH:13][cH:14][c:15]([C:16](=[O:17])[N:18]([CH2:19][CH2:20][CH:21]([CH3:22])[CH3:23])[CH2:24][CH2:25][CH:26]([CH3:27])[CH3:28])[cH:29][c:30]21.[CH3:1][NH2:2].[ClH:39]>>[CH3:1][NH:2][C:3](... | CC(C)CCN(CCC(C)C)C(=O)c1ccc2nc(Nc3ccc(C(=O)O)cc3)n(CCCNC(=O)OC(C)(C)C)c2c1.CN.Cl | CNC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCCN)cc1.Cl | null | null | C(C)(=O)OCC.C(Cl)(Cl)Cl.ClCCl.O1CCCC1.C1CCOC1 | Acylation | OtherReaction | b4c20342f55b434660078663f02be082076e2ff9b9068db91acc0b381022a32e | e525bb030a9f5f4a2fc47bce923bf921a3769ce3300b3fa2600575194671a3f3 | c1ccc(Nc2nc3ccccc3[nH]2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3].O-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6](:[c:7]):[c:8].[C;D1;H3:9]-[NH2;D1;+0:10]>>[C;D1;H3:9]-[NH;D2;+0:10]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6](:[c:7]):[c:8].[C:3]-[C:2]-[NH2;D1;+0:1] | 106.6 | [{"value": 60.0, "product": "Cl.Cl.NCCCN1C(=NC2=C1C=C(C=C2)C(=O)N(CCC(C)C)CCC(C)C)NC2=CC=C(C=C2)C(=O)NC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 106.6, "product": "Cl.Cl.NCCCN1C(=NC2=C1C=C(C=C2)C(=O)N(CCC(C)C)CCC(C)C)NC2=CC=C(C=C2)C(=O)NC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 1 | HOUR | A solution of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (18 mg, 1.1 eq) in chloroform (1 ml) and a solution of 1-hydroxybenzotriazole (HOBt) (13 mg, 1.1 eq) in tetrahydrofuran (1 ml) are successively added to 4-[(6-{[bis(3-methylbutyl)amino]carbonyl}-1-{3-[(tert-butoxycarbonyl)amino]propyl}-1H-b... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Primary amine.Boc | Secondary amide.Primary amine | null | null | c1ccccc1.c1ccc2[nH]cnc2c1 | HO- | C(C)(=O)OCC.C(Cl)(Cl)Cl.ClCCl.O1CCCC1.C1CCOC1 | 20 | 1 | CC(C)CCN(CCC(C)C)C(=O)c1ccc2nc(Nc3ccc(C(=O)O)cc3)n(CCCNC(=O)OC(C)(C)C)c2c1.CN.Cl>C(C)(=O)OCC.C(Cl)(Cl)Cl.ClCCl.O1CCCC1.C1CCOC1>CNC(=O)c1ccc(Nc2nc3ccc(C(=O)N(CCC(C)C)CCC(C)C)cc3n2CCCN)cc1.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8ed6c19ad03846bcacc519adee3dc643 | CC(C)CCN(CCC(C)C)C(=O)c1ccc(N)c(NCCCNC(=O)OC(C)(C)C)c1.O=[N+]([O-])c1ccc(N=C=S)cc1>>CC(C)CCN(CCC(C)C)C(=O)c1ccc2nc(Nc3ccc([N+](=O)[O-])cc3)n(CCCNC(=O)OC(C)(C)C)c2c1 | [N+](=O)([O-])C1=CC=C(C=C1)N=C=S.C(C)(C)(C)OC(NCCCNC1=C(C=CC(=C1)C(=O)N(CCC(C)C)CCC(C)C)N)=O>>CC(CCN(C(=O)C=1C=CC2=C(N(C(=N2)NC2=CC=C(C=C2)[N+](=O)[O-])CCCNC(OC(C)(C)C)=O)C1)CCC(C)C)C | [CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][N:6]([CH2:7][CH2:8][CH:9]([CH3:10])[CH3:11])[C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17]([NH2:18])[c:42]([NH:30][CH2:31][CH2:32][CH2:33][NH:34][C:35](=[O:36])[O:37][C:38]([CH3:39])([CH3:40])[CH3:41])[cH:43]1.S=[C:19]=[N:20][c:21]1[cH:22][cH:23][c:24]([N+:25](=[O:26])[O-:27])[cH:28][cH... | CC(C)CCN(CCC(C)C)C(=O)c1ccc(N)c(NCCCNC(=O)OC(C)(C)C)c1.O=[N+]([O-])c1ccc(N=C=S)cc1 | CC(C)CCN(CCC(C)C)C(=O)c1ccc2nc(Nc3ccc([N+](=O)[O-])cc3)n(CCCNC(=O)OC(C)(C)C)c2c1 | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | 4b3e260fa6094641dfa114b35f3471079a338332f41031b31ba4b7bb465b4139 | c2745d0d96944794048cb0a435469fb3c0efa689f6d5e8d4fd6447372cabc5f8 | c1ccc(Nc2nc3ccccc3[nH]2)cc1 | S=[C;H0;D2;+0:1]=[N;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11](-[NH2;D1;+0:12]):[c:13]>>[C:6]-[C:7]-[n;H0;D3;+0:8]1:[c:9](:[c:10]):[c:11](:[c:13]):[n;H0;D2;+0:12]:[c;H0;D3;+0:1]:1-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5] | 88 | [{"value": 88.0, "product": "CC(CCN(C(=O)C=1C=CC2=C(N(C(=N2)NC2=CC=C(C=C2)[N+](=O)[O-])CCCNC(OC(C)(C)C)=O)C1)CCC(C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-nitrophenyl isothiocyanate (305 mg, 1.5 eq) and N-methylcyclohexylcarbodiimide-N-methyl-polystyrene resin (acquired from Novabiochem; charge 1.9 mmol/g; 1.75 g, 3 eq) are successively added to a solution of tert-butyl-3-[(2-amino-5-{[bis(3-methylbutyl)amino]carbonyl}phenyl)amino]propylcarbamate prepared according to ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine.Isothiocyanate | Secondary amine | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1.c1ccccc1 | Other | O1CCCC1 | null | null | CC(C)CCN(CCC(C)C)C(=O)c1ccc(N)c(NCCCNC(=O)OC(C)(C)C)c1.O=[N+]([O-])c1ccc(N=C=S)cc1>O1CCCC1>CC(C)CCN(CCC(C)C)C(=O)c1ccc2nc(Nc3ccc([N+](=O)[O-])cc3)n(CCCNC(=O)OC(C)(C)C)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-92cc75313c9f4563914bdda9ed66a809 | CC(C)CCN(CCC(C)C)C(=O)c1ccc2nc(Nc3ccc([N+](=O)[O-])cc3)n(CCCNC(=O)OC(C)(C)C)c2c1>>CC(C)CCN(CCC(C)C)C(=O)c1ccc2nc(Nc3ccc(N)cc3)n(CCCNC(=O)OC(C)(C)C)c2c1 | CC(CCN(C(=O)C=1C=CC2=C(N(C(=N2)NC2=CC=C(C=C2)[N+](=O)[O-])CCCNC(OC(C)(C)C)=O)C1)CCC(C)C)C>>NC1=CC=C(C=C1)NC1=NC2=C(N1CCCNC(OC(C)(C)C)=O)C=C(C=C2)C(=O)N(CCC(C)C)CCC(C)C | O=[N+:25]([O-])[c:24]1[cH:23][cH:22][c:21]([NH:20][c:19]2[n:18][c:17]3[cH:16][cH:15][c:14]([C:12]([N:6]([CH2:5][CH2:4][CH:2]([CH3:1])[CH3:3])[CH2:7][CH2:8][CH:9]([CH3:10])[CH3:11])=[O:13])[cH:41][c:40]3[n:28]2[CH2:29][CH2:30][CH2:31][NH:32][C:33](=[O:34])[O:35][C:36]([CH3:37])([CH3:38])[CH3:39])[cH:27][cH:26]1>>[CH3:1]... | CC(C)CCN(CCC(C)C)C(=O)c1ccc2nc(Nc3ccc([N+](=O)[O-])cc3)n(CCCNC(=O)OC(C)(C)C)c2c1 | CC(C)CCN(CCC(C)C)C(=O)c1ccc2nc(Nc3ccc(N)cc3)n(CCCNC(=O)OC(C)(C)C)c2c1 | null | [Pd] | C(C)(=O)OCC.CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(Nc2nc3ccccc3[nH]2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 87 | [{"value": 87.0, "product": "NC1=CC=C(C=C1)NC1=NC2=C(N1CCCNC(OC(C)(C)C)=O)C=C(C=C2)C(=O)N(CCC(C)C)CCC(C)C", "details": "PERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 15 | HOUR | Tert-butyl 3-{6-{[bis(3-methylbutyl)amino]carbonyl}-2-[(4-nitrophenyl)amino]-1H-benzimidazol-1-yl}propylcarbamate (580 mg) in solution in a mixture of ethyl acetate/methanol 3:1 (40 ml), and 10% palladium on carbon (58 mg) are introduced into an autoclave. After stirring for 15 hours under a hydrogen atmosphere (3 bar)... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2[nH]cnc2c1.c1ccccc1 | Other | [Pd].C(C)(=O)OCC.CO | 20 | 15 | CC(C)CCN(CCC(C)C)C(=O)c1ccc2nc(Nc3ccc([N+](=O)[O-])cc3)n(CCCNC(=O)OC(C)(C)C)c2c1>[Pd].C(C)(=O)OCC.CO>CC(C)CCN(CCC(C)C)C(=O)c1ccc2nc(Nc3ccc(N)cc3)n(CCCNC(=O)OC(C)(C)C)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9cfe172dd41d410891604a2ccc917652 | C1CCOC1.CCN(CC)CC>>CCN(C(C)C)C(C)C | C(C)N(CC)CC.ClCCl.O1CCCC1>>C(C)(C)N(CC)C(C)C | C1OC[CH2:9][CH2:5]1.[CH3:1][CH2:2][N:3]([CH2:4][CH3:6])[CH2:7][CH3:8]>>[CH3:1][CH2:2][N:3]([CH:4]([CH3:5])[CH3:6])[CH:7]([CH3:8])[CH3:9] | C1CCOC1.CCN(CC)CC | CCN(C(C)C)C(C)C | null | null | null | C-C Coupling | OtherReaction | f4c1d2f351d19986fdb53e5c3242a30777f8f4b37ce27cc541347a8a34a04c62 | a5693ad0ff37ba299a3384a72fcc8b66e16e2c53e1f48e2cc3e13008b4273e5a | null | C1-O-C-[CH2;D2;+0:1]-[CH2;D2;+0:2]-1.[C:3]-[#7:4](-[CH2;D2;+0:5]-[C;D1;H3:6])-[CH2;D2;+0:7]-[C;D1;H3:8]>>[C:3]-[#7:4](-[CH;D3;+0:5](-[C;D1;H3:6])-[CH3;D1;+0:2])-[CH;D3;+0:7](-[C;D1;H3:8])-[CH3;D1;+0:1] | null | [] | null | null | null | null | As described in diagram G, the derivative (26) can be alkylated in the presence of a strong base such as potassium tertbutylate, by an α-chloroester derivative, in an aprotic polar solvent such as dimethylformamide at a temperature of 0-20° C. for 0.5-2 hours, in order to produce compound (27). The derivative (27) can ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | null | C1CCOC1 | null | null | HO- | null | null | null | C1CCOC1.CCN(CC)CC>>CCN(C(C)C)C(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4366ed6912c4479593a0abab16c524e8 | CCOC(=O)C(C)Cl.O=[N+]([O-])c1ccccc1Cl>>CCOC(=O)C(C)c1ccc([N+](=O)[O-])c(Cl)c1 | ClC1=C(C=CC=C1)[N+](=O)[O-].ClC(C(=O)OCC)C.Cl.CC(C)(C)[O-].[K+]>>ClC=1C=C(C=CC1[N+](=O)[O-])C(C(=O)OCC)C | Cl[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH3:7].[cH:8]1[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[c:15]([Cl:16])[cH:17]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH3:7])[c:8]1[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[c:15]([Cl:16])[cH:17]1 | CCOC(=O)C(C)Cl.O=[N+]([O-])c1ccccc1Cl | CCOC(=O)C(C)c1ccc([N+](=O)[O-])c(Cl)c1 | null | null | CN(C)C=O.C(C)(=O)OCC | C-C Coupling | OtherReaction | 40ca321fe4047c56d3dec7ae738915164e802e06a6dc78b541aeb3597dd936df | ae23b78d8cc9afe1235c3056fa58900d3a27e232dc891dd767f4195ab4ddcbb6 | c1ccccc1 | Cl-[CH;D3;+0:1](-[C;D1;H3:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6].[c:7]:[c:8]:[cH;D2;+0:9]:[c:10]:[c:11]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:1](-[C;D1;H3:2])-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:8]:[c:7] | 64 | [{"value": 64.0, "product": "ClC=1C=C(C=CC1[N+](=O)[O-])C(C(=O)OCC)C", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | Potassium tert-butylate (11.22 g, 2 eq) is added to a solution of DMF (80 ml) cooled down to 0° C. A solution of 1-chloro-2-nitrobenzene (7.87 g, 1 eq) and ethyl 2-chloropropanoate (7 ml, 1.1 eq) is added dropwise over 45 minutes to the mixture whilst keeping the reaction temperature below 5° C. At the end of the addit... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ester | Ester | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | CN(C)C=O.C(C)(=O)OCC | 0 | null | CCOC(=O)C(C)Cl.O=[N+]([O-])c1ccccc1Cl>CN(C)C=O.C(C)(=O)OCC>CCOC(=O)C(C)c1ccc([N+](=O)[O-])c(Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0166efd653fb481392f5e56021c292a9 | CCOC(=O)C(C)c1ccc([N+](=O)[O-])c(Cl)c1.CI>>CCOC(=O)C(C)(C)c1ccc([N+](=O)[O-])c(Cl)c1 | ClC=1C=C(C=CC1[N+](=O)[O-])C(C(=O)OCC)C.[H-].[Na+].C(O)([O-])=O.[Na+].CI>>ClC=1C=C(C=CC1[N+](=O)[O-])C(C(=O)OCC)(C)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH3:7])[c:9]1[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[c:16]([Cl:17])[cH:18]1.I[CH3:8]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH3:7])([CH3:8])[c:9]1[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[c:16]([Cl:17])[cH:18]1 | CCOC(=O)C(C)c1ccc([N+](=O)[O-])c(Cl)c1.CI | CCOC(=O)C(C)(C)c1ccc([N+](=O)[O-])c(Cl)c1 | null | null | O.CN(C)C=O.C(C)(=O)OCC | C-C Coupling | Methylation with MeI_tertiary | 4a52ebe9ffae5bdd307b0b4ac6a7069bc533ab8d42293ed2712c32b846010273 | 49d6f28766066d07dffbcc6f4da77792f6ba67b4de619800bad651525d6fe2e7 | c1ccccc1 | I-[CH3;D1;+0:1].[C:2]-[#8:3]-[C:4](=[O;D1;H0:5])-[CH;D3;+0:6](-[C;D1;H3:7])-[c:8](:[c:9]):[c:10]>>[C:2]-[#8:3]-[C:4](=[O;D1;H0:5])-[C;H0;D4;+0:6](-[C;D1;H3:7])(-[CH3;D1;+0:1])-[c:8](:[c:9]):[c:10] | 94 | [{"value": 94.0, "product": "ClC=1C=C(C=CC1[N+](=O)[O-])C(C(=O)OCC)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | A solution of ethyl 2-(3-chloro-4-nitrophenyl)propanoate (14.1 g) is added dropwise to a suspension of sodium hydride (60% in oil, 2.4 g, 1.1 eq) in DMF (15 ml), cooled down to 0° C. After stirring for 1 hour at this temperature, a solution of methyl iodide (3.72 ml, 1.1 eq) in DMF (40 ml) is added dropwise to the mixt... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | null | null | c1ccccc1 | HI | O.CN(C)C=O.C(C)(=O)OCC | 0 | 1 | CCOC(=O)C(C)c1ccc([N+](=O)[O-])c(Cl)c1.CI>O.CN(C)C=O.C(C)(=O)OCC>CCOC(=O)C(C)(C)c1ccc([N+](=O)[O-])c(Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-827176e1ff9e4f1bbdb24ad944e0fab4 | CCOC(=O)C(C)(C)c1ccc([N+](=O)[O-])c(Cl)c1>>CC(C)(C(=O)O)c1ccc([N+](=O)[O-])c(Cl)c1 | [OH-].[K+].ClC=1C=C(C=CC1[N+](=O)[O-])C(C(=O)OCC)(C)C>>ClC=1C=C(C=CC1[N+](=O)[O-])C(C(=O)O)(C)C | CC[O:6][C:4]([C:2]([CH3:1])([CH3:3])[c:7]1[cH:8][cH:9][c:10]([N+:11](=[O:12])[O-:13])[c:14]([Cl:15])[cH:16]1)=[O:5]>>[CH3:1][C:2]([CH3:3])([C:4](=[O:5])[OH:6])[c:7]1[cH:8][cH:9][c:10]([N+:11](=[O:12])[O-:13])[c:14]([Cl:15])[cH:16]1 | CCOC(=O)C(C)(C)c1ccc([N+](=O)[O-])c(Cl)c1 | CC(C)(C(=O)O)c1ccc([N+](=O)[O-])c(Cl)c1 | null | null | CO | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 95 | [{"value": 95.0, "product": "ClC=1C=C(C=CC1[N+](=O)[O-])C(C(=O)O)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A 2N solution of potassium hydroxide (18 ml) is added at a temperature of approximately 20° C. to a solution of ethyl 2-(3-chloro-4-nitrophenyl)-2-methylpropanoate (1 g) in methanol (20 ml). The mixture is then heated at 80° C. for 1.5 hours then cooled down to ambient temperature. The methanol is evaporated by concent... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | CO | 80 | null | CCOC(=O)C(C)(C)c1ccc([N+](=O)[O-])c(Cl)c1>CO>CC(C)(C(=O)O)c1ccc([N+](=O)[O-])c(Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a67b869a08784a34a876df49a6c97e47 | CC(C)(C(=O)O)c1ccc([N+](=O)[O-])c(Cl)c1.CC(C)CNCC(C)C>>CC(C)CN(CC(C)C)C(=O)C(C)(C)c1ccc([N+](=O)[O-])c(Cl)c1 | S(=O)(Cl)Cl.ClC=1C=C(C=CC1[N+](=O)[O-])C(C(=O)O)(C)C.C(C)(C)N(CC)C(C)C.C(C(C)C)NCC(C)C>>ClC=1C=C(C=CC1[N+](=O)[O-])C(C(=O)N(CC(C)C)CC(C)C)(C)C | O[C:10](=[O:11])[C:12]([CH3:13])([CH3:14])[c:15]1[cH:16][cH:17][c:18]([N+:19](=[O:20])[O-:21])[c:22]([Cl:23])[cH:24]1.[CH3:1][CH:2]([CH3:3])[CH2:4][NH:5][CH2:6][CH:7]([CH3:8])[CH3:9]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]([CH2:6][CH:7]([CH3:8])[CH3:9])[C:10](=[O:11])[C:12]([CH3:13])([CH3:14])[c:15]1[cH:16][cH:17][c:18]([N... | CC(C)(C(=O)O)c1ccc([N+](=O)[O-])c(Cl)c1.CC(C)CNCC(C)C | CC(C)CN(CC(C)C)C(=O)C(C)(C)c1ccc([N+](=O)[O-])c(Cl)c1 | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[c:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[C:10]-[C:11])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[c:6] | 82 | [{"value": 82.0, "product": "ClC=1C=C(C=CC1[N+](=O)[O-])C(C(=O)N(CC(C)C)CC(C)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Thionyl chloride (0.54 ml, 4 eq) is added to a solution of 2-(3-chloro-4-nitrophenyl)-2-methylpropanoic acid (500 mg) in dichloromethane (1 ml). The mixture is heated under reflux for 16 hours then cooled down to ambient temperature. The solvent is evaporated off under reduced pressure at 40° C. (co-evaporation with to... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccccc1 | HO- | ClCCl | null | 3 | CC(C)(C(=O)O)c1ccc([N+](=O)[O-])c(Cl)c1.CC(C)CNCC(C)C>ClCCl>CC(C)CN(CC(C)C)C(=O)C(C)(C)c1ccc([N+](=O)[O-])c(Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f16aebf03a824d07846dc4911392ba5c | CC(C)CN(CC(C)C)C(=O)C(C)(C)c1ccc([N+](=O)[O-])c(Cl)c1.CN(C)CCCN>>CC(C)CN(CC(C)C)C(=O)C(C)(C)c1ccc([N+](=O)[O-])c(NCCCN(C)C)c1 | ClC=1C=C(C=CC1[N+](=O)[O-])C(C(=O)N(CC(C)C)CC(C)C)(C)C.CN(CCCN)C.C([O-])([O-])=O.[K+].[K+]>>CN(CCCNC=1C=C(C=CC1[N+](=O)[O-])C(C(=O)N(CC(C)C)CC(C)C)(C)C)C | Cl[c:22]1[c:18]([N+:19](=[O:20])[O-:21])[cH:17][cH:16][c:15]([C:12]([C:10]([N:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[CH2:6][CH:7]([CH3:8])[CH3:9])=[O:11])([CH3:13])[CH3:14])[cH:30]1.[NH2:23][CH2:24][CH2:25][CH2:26][N:27]([CH3:28])[CH3:29]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]([CH2:6][CH:7]([CH3:8])[CH3:9])[C:10](=[O:11])[C:12... | CC(C)CN(CC(C)C)C(=O)C(C)(C)c1ccc([N+](=O)[O-])c(Cl)c1.CN(C)CCCN | CC(C)CN(CC(C)C)C(=O)C(C)(C)c1ccc([N+](=O)[O-])c(NCCCN(C)C)c1 | null | null | O.CN(C)C=O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccccc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[c:2]:[c:3] | 48 | [{"value": 48.0, "product": "CN(CCCNC=1C=C(C=CC1[N+](=O)[O-])C(C(=O)N(CC(C)C)CC(C)C)(C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-(3-chloro-4-nitrophenyl)-N,N-diisobutyl-2-methylpropanamide (78 mg, 1 eq), 3-dimethylaminopropylamine (45 mg, 2 eq) and potassium carbonate (62 mg, 2 eq) in DMF (2 ml) is heated under reflux for 3 hours then cooled down to ambient temperature. The residue is taken up in ethyl acetate (20 ml) and water (8... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | O.CN(C)C=O.C(C)(=O)OCC | null | null | CC(C)CN(CC(C)C)C(=O)C(C)(C)c1ccc([N+](=O)[O-])c(Cl)c1.CN(C)CCCN>O.CN(C)C=O.C(C)(=O)OCC>CC(C)CN(CC(C)C)C(=O)C(C)(C)c1ccc([N+](=O)[O-])c(NCCCN(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9261c4e1f3794937949ea4a425d4a58d | CC(C)CN(CC(C)C)C(=O)C(C)(C)c1ccc([N+](=O)[O-])c(NCCCN(C)C)c1>>CC(C)CN(CC(C)C)C(=O)C(C)(C)c1ccc(N)c(NCCCN(C)C)c1 | CN(CCCNC=1C=C(C=CC1[N+](=O)[O-])C(C(=O)N(CC(C)C)CC(C)C)(C)C)C>>NC1=C(C=C(C=C1)C(C(=O)N(CC(C)C)CC(C)C)(C)C)NCCCN(C)C | O=[N+:19]([O-])[c:18]1[cH:17][cH:16][c:15]([C:12]([C:10]([N:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[CH2:6][CH:7]([CH3:8])[CH3:9])=[O:11])([CH3:13])[CH3:14])[cH:28][c:20]1[NH:21][CH2:22][CH2:23][CH2:24][N:25]([CH3:26])[CH3:27]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]([CH2:6][CH:7]([CH3:8])[CH3:9])[C:10](=[O:11])[C:12]([CH3:13])([C... | CC(C)CN(CC(C)C)C(=O)C(C)(C)c1ccc([N+](=O)[O-])c(NCCCN(C)C)c1 | CC(C)CN(CC(C)C)C(=O)C(C)(C)c1ccc(N)c(NCCCN(C)C)c1 | null | [Pd] | C(C)(=O)OCC.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] | 95 | [{"value": 95.0, "product": "NC1=C(C=C(C=C1)C(C(=O)N(CC(C)C)CC(C)C)(C)C)NCCCN(C)C", "details": "PERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 4 | HOUR | 2-(3-{[3-(dimethylamino)propyl]amino}-4-nitrophenyl)-N,N-diisobutyl-2-methylpropanamide (44 mg) in solution in a mixture of ethyl acetate/ethanol 2:1 (3 ml), and 10% palladium on carbon (5 mg) are introduced into an autoclave. After stirring for 4 hours under a hydrogen atmosphere (3 bar) at a temperature of approximat... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Pd].C(C)(=O)OCC.C(C)O | 20 | 4 | CC(C)CN(CC(C)C)C(=O)C(C)(C)c1ccc([N+](=O)[O-])c(NCCCN(C)C)c1>[Pd].C(C)(=O)OCC.C(C)O>CC(C)CN(CC(C)C)C(=O)C(C)(C)c1ccc(N)c(NCCCN(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9dedbdb954234bc38901e15b106bf77a | CC(C)(C#N)N=NC(C)(C)C#N.CC1(C)CCCC(C)(C)N1[O].O=C1C=CC(=O)O1>>C=CC(=O)OCCCC.C=Cc1ccccc1 | C1(\C=C/C(=O)O1)=O.CC1(CCCC(N1[O])(C)C)C.CC(C)(C#N)N=NC(C)(C)C#N.C1(\C=C/C(=O)O1)=O>>C=CC1=CC=CC=C1.C(CCC)OC(C=C)=O | CC(C#N)(N=N[C:8](C)([C:7]#N)[CH3:10])[CH3:9].C[C:12]1([CH3:11])N([O])[C:14](C)([CH3:13])[CH2:15][CH2:16][CH2:17]1.O=[C:6]1[CH:1]=[CH:2][C:3](=[O:4])[O:5]1>>[CH2:1]=[CH:2][C:3](=[O:4])[O:5][CH2:6][CH2:7][CH2:8][CH3:9].[CH2:10]=[CH:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | CC(C)(C#N)N=NC(C)(C)C#N.CC1(C)CCCC(C)(C)N1[O].O=C1C=CC(=O)O1 | C=CC(=O)OCCCC.C=Cc1ccccc1 | null | null | C=CC1=CC=CC=C1.C(CCC)OC(C=C)=O | C-C Coupling | OtherReaction | fcac0dc2f8789f75ae63b0f2c11c7cf93a0b9a9ff4f12b95a91e90b7737e0820 | 85fd3307a3b96f5aaa701b422307122b849f0a118e9a328013d3ea17cd6e1d1c | c1ccccc1 | C-C(-[CH3;D1;+0:1])(-C#N)-N=N-[C;H0;D4;+0:2](-C)(-[CH3;D1;+0:3])-[C;H0;D2;+0:4]#N.C-[C;H0;D4;+0:5]1(-[CH3;D1;+0:6])-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[C;H0;D4;+0:10](-C)(-[CH3;D1;+0:11])-N-1-[O].O=[C;H0;D3;+0:12]1-[#8:13]-[C:14](=[O;D1;H0:15])-[C:16]=[CH;D2;+0:17]-1>>[CH2;D1;+0:3]=[CH;D2;+0:6]-[c;H0;D3;+0:5]1:[... | null | [] | 135 | CELSIUS | 30 | MINUTE | Incorporation of maleic anhydride into an emulsion aggregation particle at the bulk polymerization step. A stock solution of styrene (390 mL) and butylacrylate (110 ml) was prepared and to 400 ml was added TEMPO (3.12 g, 0.02 mole) and vazo 64 initiator (2.0 g, 0.0125 mole). This was heated under a nitrogen atmosphere ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Diazene.Nitrile.Nitrile.Tertiary amine | Ester.Vinyl.Vinyl | C1CCNCC1.C1=CCOC1 | c1ccccc1 | c1ccccc1 | HO- | C=CC1=CC=CC=C1.C(CCC)OC(C=C)=O | 135 | 0.5 | CC(C)(C#N)N=NC(C)(C)C#N.CC1(C)CCCC(C)(C)N1[O].O=C1C=CC(=O)O1>C=CC1=CC=CC=C1.C(CCC)OC(C=C)=O>C=CC(=O)OCCCC.C=Cc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8fc42ccc4923492b92e3b384212187a5 | NNc1ccc(F)cc1.c1ccc2[nH]ccc2c1>>Fc1ccc2[nH]ccc2c1 | Cl.FC1=CC=C(C=C1)NN.CC(C(C)=O)C.N1C=CC2=CC=CC=C12>>FC=1C=C2C=CNC2=CC1 | NNc1cc[c:2]([F:1])[cH:3]c1.c1c[cH:10][c:9]2[c:5]([cH:4]1)[nH:6][cH:7][cH:8]2>>[F:1][c:2]1[cH:3][cH:4][c:5]2[nH:6][cH:7][cH:8][c:9]2[cH:10]1 | NNc1ccc(F)cc1.c1ccc2[nH]ccc2c1 | Fc1ccc2[nH]ccc2c1 | null | null | C(C)(=O)O | Miscellaneous | OtherReaction | c7316a6e49c198c5b6eb864d13f3e8770cf7438fc17309820bf3b22bc37850db | b5fb865f2648435aa40090d05ac327c82ecb3300512ab6afa7415a6f0fdd5442 | c1ccc2[nH]ccc2c1 | N-N-c1:c:[cH;D2;+0:1]:[c;H0;D3;+0:2](-[F;D1;H0:3]):c:c:1.[#7;a:4]1:[c:5]:[c:6]:[c:7]2:[cH;D2;+0:8]:c:c:[cH;D2;+0:9]:[c:10]:1:2>>[F;D1;H0:3]-[c;H0;D3;+0:2]1:[cH;D2;+0:8]:[c:7]2:[c:6]:[c:5]:[#7;a:4]:[c:10]:2:[cH;D2;+0:9]:[cH;D2;+0:1]:1 | 99.9 | [{"value": 76.0, "product": "FC=1C=C2C=CNC2=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.9, "product": "FC=1C=C2C=CNC2=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 130 | CELSIUS | 30 | MINUTE | A mixture containing 4-Fluorophenylhydrazine hydrochloride (5.0 g; 30.75 mmol; ALDRICH), 3-methyl-2-butanone (3.7 g; 43 mmol; ALDRICH) and acetic acid (30 ml) was stirred for 30 min. under nitrogen to obtain the clear solution. The mixture was then refluxed at 130° C. The appearance of UV-Vis Abs. Max at 255 nm and the... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Aromatic halide | Aromatic halide | c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | Other | C(C)(=O)O | 130 | 0.5 | NNc1ccc(F)cc1.c1ccc2[nH]ccc2c1>C(C)(=O)O>Fc1ccc2[nH]ccc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a931cab23a544901b816ee4fd39fbe7f | CC(=O)C(CO)CO.CC1=Nc2ccc(CC(=O)O)cc2C1(C)C>>CC1=Nc2ccc(CC(=O)O)cc2C1(CO)CO | Cl.C(=O)(O)CC1=CC=C(C=C1)NN.OCC(C(C)=O)CO.OC=1NC2=CC=CC=C2C1.CC1=NC2=CC=C(C=C2C1(C)C)CC(=O)O>>OCC1(C(=NC2=CC=C(C=C12)CC(=O)O)C)CO | CC(=O)C(C[OH:18])[CH2:15][OH:16].C[C:14]1([CH3:17])[C:2]([CH3:1])=[N:3][c:4]2[cH:5][cH:6][c:7]([CH2:8][C:9](=[O:10])[OH:11])[cH:12][c:13]21>>[CH3:1][C:2]1=[N:3][c:4]2[cH:5][cH:6][c:7]([CH2:8][C:9](=[O:10])[OH:11])[cH:12][c:13]2[C:14]1([CH2:15][OH:16])[CH2:17][OH:18] | CC(=O)C(CO)CO.CC1=Nc2ccc(CC(=O)O)cc2C1(C)C | CC1=Nc2ccc(CC(=O)O)cc2C1(CO)CO | null | null | C(C)(=O)O | Heteroatom Alkylation and Arylation | OtherReaction | c0bf8559cd0361fe49e1a3aac05a98a56db30e061e1edc4dcc2c3624afe1e237 | eb3748cc6ce4cece71ed2b5d70393616746afd774bc4ece9d922633e34f6f105 | C1=Nc2ccccc2C1 | C-C(=O)-C(-C-[OH;D1;+0:1])-[CH2;D2;+0:2]-[O;D1;H1:3].C-[C;H0;D4;+0:4]1(-[CH3;D1;+0:5])-[C:6](-[C;D1;H3:7])=[#7:8]-[c:9]:[c:10]-1:[c:11]>>[C;D1;H3:7]-[C:6]1=[#7:8]-[c:9]:[c:10](:[c:11])-[C;H0;D4;+0:4]-1(-[CH2;D2;+0:2]-[O;D1;H1:3])-[CH2;D2;+0:5]-[OH;D1;+0:1] | null | [] | null | null | null | null | The hydroxy-indole compound is readily prepared by a known method (P. L. Southwick, et al., One pot Fischer synthesis of (2,3,3-trimethyl-3-H-indol-5-yl)-acetic acid derivatives as intermediates for fluorescent biolabels. Org. Prep. Proced. Int. Briefs, 1988, 20(3), 279-284). Reaction of p-carboxymethylphenylhydrazine ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary alcohol.Primary alcohol | Primary alcohol.Primary alcohol | C1=Nc2ccccc2C1 | C1=Nc2ccccc2C1 | C1=Nc2ccccc2C1 | HO- | C(C)(=O)O | null | null | CC(=O)C(CO)CO.CC1=Nc2ccc(CC(=O)O)cc2C1(C)C>C(C)(=O)O>CC1=Nc2ccc(CC(=O)O)cc2C1(CO)CO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-301eb002e0b2450a8bb78e57dd21f193 | Cc1cc(C)c(C(=O)P(=O)(C(=O)c2c(C)cc(C)cc2C)c2ccccc2)c(C)c1.O=C(c1ccccc1)C1(O)CCCCC1>>Cc1cc(C)c(C(=O)P(=O)(c2ccccc2)c2ccccc2)c(C)c1 | C1(=CC=CC=C1)C(=O)C1(CCCCC1)O.COC(C(=O)C1=C(C=CC=C1)OC)C1=CC=CC=C1.C(C1=CC=CC=C1)C(C(=O)C1=CC=C(C=C1)N1CCOCC1)(CC)N(C)C.COC1=C(C(=O)P(CC(CC(C)(C)C)C)(C(C2=C(C=CC=C2OC)OC)=O)=O)C(=CC=C1)OC.OC1(CCCCC1)C1=C(C=CC=C1)C(=O)C1=C(C=CC=C1)C1(CCCCC1)O.CC1=C(C(=O)P(C2=CC=CC=C2)(C(C2=C(C=C(C=C2C)C)C)=O)=O)C(=CC(=C1)C)C>>C1(=CC=CC=... | Cc1cc(C)c(C(=O)[P:9]([C:7]([c:6]2[c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:25][c:23]2[CH3:24])=[O:8])(=[O:10])[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)c(C)c1.O=C(C1(O)CCCCC1)[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([C:7](=[O:8])[P:9](=[O:10])([c:11]2[cH:12][cH:13][cH:14][cH:15]... | Cc1cc(C)c(C(=O)P(=O)(C(=O)c2c(C)cc(C)cc2C)c2ccccc2)c(C)c1.O=C(c1ccccc1)C1(O)CCCCC1 | Cc1cc(C)c(C(=O)P(=O)(c2ccccc2)c2ccccc2)c(C)c1 | null | null | null | Miscellaneous | OtherReaction | 82b689e57d937419b1dd354f4127918b368e892b25a656f2c6e0ebcd77d4a391 | 69d3e3d2380e56677c1e31e4ce1ccde799c18afe53006f5fea39876f7f8b8218 | O=C(c1ccccc1)P(=O)(c1ccccc1)c1ccccc1 | C-c1:c:c(-C):c(-C(=O)-[P;H0;D4;+0:1](=[O;D1;H0:2])(-[C:3](=[O;D1;H0:4])-[c:5])-[c:6](:[c:7]):[c:8]):c(-C):c:1.O-C1(-C(=O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13])-C-C-C-C-C-1>>[O;D1;H0:2]=[P;H0;D4;+0:1](-[C:3](=[O;D1;H0:4])-[c:5])(-[c:6](:[c:7]):[c:8])-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13] | null | [] | null | null | null | null | 1-hydroxycyclohexyl phenyl ketone; bis (2,4,6-trimethylbenzoyl)-phenylphosphine oxide such as Irgacure 819 from BASF; 2,2′-dimethoxy-2-phenylacetophenone; 2-benzyl-2-(dimethylamino)-1-[4-(4-morpholinyl)phenyl]-1-butanone; 2-methyl-1-(4(methylthio)phenyl)-2-moropholino-1-propane; bis (2,6-dimethoxybenzoyl)-2,4,4-trimeth... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Tertiary alcohol | null | c1ccccc1.C1CCCCC1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | null | null | null | Cc1cc(C)c(C(=O)P(=O)(C(=O)c2c(C)cc(C)cc2C)c2ccccc2)c(C)c1.O=C(c1ccccc1)C1(O)CCCCC1>>Cc1cc(C)c(C(=O)P(=O)(c2ccccc2)c2ccccc2)c(C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4e06c0a69767424b81c686ac68d95663 | C=Cc1ccc(OC(C)=O)cc1>>C=Cc1ccc(OC(C)=O)cc1 | COC=1C=C(C=C)C=CC1OC(C)=O.C(C)(=O)OC1=CC=C(C=C)C=C1.N(=NC(C(=O)OC)(C)C)C(C(=O)OC)(C)C>>C(C)(=O)OC1=CC=C(C=C)C=C1.COC=1C=C(C=C)C=CC1OC(C)=O | [CH2:15]=[CH:16][c:17]1[cH:18][cH:19][c:20]([O:21][C:22]([CH3:23])=[O:24])[cH:25][cH:26]1>>[CH2:15]=[CH:16][c:17]1[cH:18][cH:19][c:20]([O:21][C:22]([CH3:23])=[O:24])[cH:25][cH:26]1 | C=Cc1ccc(OC(C)=O)cc1 | C=Cc1ccc(OC(C)=O)cc1 | null | null | O1CCCC1.CCCCCC.CC(=O)C | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccccc1 | null | 170 | [{"value": 170.0, "product": "C(C)(=O)OC1=CC=C(C=C)C=C1.COC=1C=C(C=C)C=CC1OC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | null | null | In a reaction vessel, 96.1 g (0.5 mol) of 3-methoxy-4-acetoxystyrene (produced by Honshu Chemical Industry Co., Ltd.) and 81.1 g (0.5 mol) of 4-acetoxystyrene (produced by Honshu Chemical Industry Co., Ltd.) were dissolved in 400 ml of tetrahydrofuran. While stirring the resulting solution, a nitrogen gas was passed in... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | O1CCCC1.CCCCCC.CC(=O)C | 65 | null | C=Cc1ccc(OC(C)=O)cc1>O1CCCC1.CCCCCC.CC(=O)C>C=Cc1ccc(OC(C)=O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2978a0369c104991a56a0422e78377f2 | C=Cc1ccc(OC(C)OCC)cc1>>C=Cc1ccc(OC(C)OCC)cc1 | COC=1C=C(C=C)C=CC1OC(C)OCC.C(C)OC(C)OC1=CC=C(C=C)C=C1>>C(C)OC(C)OC1=CC=C(C=C)C=C1.COC=1C=C(C=C)C=CC1OC(C)OCC | [CH2:17]=[CH:18][c:19]1[cH:20][cH:21][c:22]([O:23][CH:24]([CH3:25])[O:26][CH2:27][CH3:28])[cH:29][cH:30]1>>[CH2:17]=[CH:18][c:19]1[cH:20][cH:21][c:22]([O:23][CH:24]([CH3:25])[O:26][CH2:27][CH3:28])[cH:29][cH:30]1 | C=Cc1ccc(OC(C)OCC)cc1 | C=Cc1ccc(OC(C)OCC)cc1 | null | C(CCC)[Li] | O1CCCC1.CC(=O)C.CO | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccccc1 | null | 148 | [{"value": 148.0, "product": "C(C)OC(C)OC1=CC=C(C=C)C=C1.COC=1C=C(C=C)C=CC1OC(C)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | null | null | In a reaction vessel, 111.2 g (0.5 mol) of 3-methoxy-4-(1-ethoxyethoxy)styrene purified by distillation and 96.1 g (0.5 mol) of 4-(1-ethoxyethoxy)styrene (produced by Tosoh Corp.) were dissolved in 500 ml of dehydrated tetrahydrofuran. While stirring the resulting solution, a nitrogen gas was passed into the system and... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | C(CCC)[Li].O1CCCC1.CC(=O)C.CO | -78 | null | C=Cc1ccc(OC(C)OCC)cc1>C(CCC)[Li].O1CCCC1.CC(=O)C.CO>C=Cc1ccc(OC(C)OCC)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-754682a7a8f443a6b5e6a05cf8a29108 | BrCc1ccccc1.Brc1ccc2[nH]c3ccc(Br)cc3c2c1>>Brc1ccc2c(c1)c1cc(Br)ccc1n2Cc1ccccc1 | O.BrC=1C=CC=2NC3=CC=C(C=C3C2C1)Br.[H-].[Na+].C(C1=CC=CC=C1)Br>>C(C1=CC=CC=C1)N1C2=CC=C(C=C2C=2C=C(C=CC12)Br)Br | Br[CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.[Br:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[c:8]1[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]1[nH:15]2>>[Br:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[c:8]1[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]1[n:15]2[CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1 | BrCc1ccccc1.Brc1ccc2[nH]c3ccc(Br)cc3c2c1 | Brc1ccc2c(c1)c1cc(Br)ccc1n2Cc1ccccc1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | df80d1938e751b5a2f242c465b00cf6e2a34a88255e6650094c05596f91512d9 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cn2c3ccccc3c3ccccc32)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[c:5]:[c:6]1:[c:7]:[c:8]:[c:9](:[c:10]):[nH;D2;+0:11]:1>>[c:5]:[c:6]1:[c:7]:[c:8]:[c:9](:[c:10]):[n;H0;D3;+0:11]:1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 61 | [{"value": 61.0, "product": "C(C1=CC=CC=C1)N1C2=CC=C(C=C2C=2C=C(C=CC12)Br)Br", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Under a nitrogen atmosphere, 3,6-dibromocarbazole (9.75 g, 30 mmol) was slowly added to a suspension of sodium hydride (45 mmol) in dried THF (100 mL), and then stirred for 30 minutes at room temperature. Benzylbromide (6.72 g, 40 mmol) was dropped into the reaction mixture to be stirred for 20 hours. After addition of... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2c(c1)[nH]c1ccccc12 | c1ccc2[nH]c3ccccc3c2c1 | c1ccccc1.c1ccc2[nH]c3ccccc3c2c1 | HBr | C1CCOC1 | null | 0.5 | BrCc1ccccc1.Brc1ccc2[nH]c3ccc(Br)cc3c2c1>C1CCOC1>Brc1ccc2c(c1)c1cc(Br)ccc1n2Cc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b8fd5a045a774095917e7a6e7df679dd | Brc1ccc2c(c1)c1cc(Br)ccc1n2Cc1ccccc1.CCn1c2ccc(Br)cc2c2cc(Br)ccc21.c1ccc2c(c1)[nH]c1ccccc12>>c1ccc(Cn2c3ccc(-n4c5ccccc5c5ccccc54)cc3c3cc(-n4c5ccccc5c5ccccc54)ccc32)cc1 | C(C1=CC=CC=C1)N1C2=CC=C(C=C2C=2C=C(C=CC12)Br)Br.C1=CC=CC=2C3=CC=CC=C3NC12.C(C)N1C2=CC=C(C=C2C=2C=C(C=CC12)Br)Br>>C(C1=CC=CC=C1)N1C2=CC=C(C=C2C=2C=C(C=CC12)N1C2=CC=CC=C2C=2C=CC=CC12)N1C2=CC=CC=C2C=2C=CC=CC12 | Br[c:20]1[cH:19][c:18]2[c:23]([n:6]([CH2:5][c:4]3[cH:3][cH:2][cH:1][cH:46][cH:45]3)[c:44]3[c:26]2[cH:27][c:28](Br)[cH:42][cH:43]3)[cH:22][cH:21]1.CC[n:11]1[c:7]2[cH:8][cH:9][c:10](Br)[cH:24][c:25]2[c:17]2[c:12]1[cH:13][cH:14][c:15](Br)[cH:16]2.[nH:29]1[c:30]2[cH:31][cH:32][cH:33][cH:34][c:35]2[c:36]2[cH:37][cH:38][cH:3... | Brc1ccc2c(c1)c1cc(Br)ccc1n2Cc1ccccc1.CCn1c2ccc(Br)cc2c2cc(Br)ccc21.c1ccc2c(c1)[nH]c1ccccc12 | c1ccc(Cn2c3ccc(-n4c5ccccc5c5ccccc54)cc3c3cc(-n4c5ccccc5c5ccccc54)ccc32)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | a6634442574cbcd0e6b982233524f2c21ad036f5e44040fb38d16f9692126c20 | cc78ad17de37d36395f9e0651dd12cd2067f91a035d2585d52dc1969a1f710b5 | c1ccc(Cn2c3ccc(-n4c5ccccc5c5ccccc54)cc3c3cc(-n4c5ccccc5c5ccccc54)ccc32)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c;H0;D3;+0:3]2:[c;H0;D3;+0:4](:[c:5]:[c:6]:1):[n;H0;D3;+0:7](-[C:8]-[c:9]):[c:10]1:[c:11]:[c:12]:[c;H0;D3;+0:13](-Br):[c:14]:[c;H0;D3;+0:15]:1:2.Br-[c;H0;D3;+0:16]1:[c:17]:[c;H0;D3;+0:18]2:[c;H0;D3;+0:19]3:[c:20]:[c;H0;D3;+0:21](-Br):[c:22]:[c:23]:[c:24]:3:[n;H0;D3;+0:25](-C-C):[c;H0;D3;+0:26]... | 70 | [{"value": 70.0, "product": "C(C1=CC=CC=C1)N1C2=CC=C(C=C2C=2C=C(C=CC12)N1C2=CC=CC=C2C=2C=CC=CC12)N1C2=CC=CC=C2C=2C=CC=CC12", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The obtained N-benzyl-3,6-dibromocarbazole was allowed to couple with carbazole in the same manner as described in synthesis of N-ethyl-3,6-dibromocarbazole (Embodiment 1) to give N-benzyl-3,6-di(N-carbazolyl)carbazole. The yield was 70%.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide | null | c1ccc2[nH]c3ccccc3c2c1.c1ccc2[nH]c3ccccc3c2c1.c1ccc2c(c1)[nH]c1ccccc12 | c1ccc2[nH]c3ccccc3c2c1.c1ccc2c(c1)[nH]c1ccccc12.c1ccc2c(c1)[nH]c1ccccc12 | c1ccccc1.c1ccc2[nH]c3ccccc3c2c1.c1ccc2c(c1)[nH]c1ccccc12.c1ccc2c(c1)[nH]c1ccccc12 | HBr | null | null | null | Brc1ccc2c(c1)c1cc(Br)ccc1n2Cc1ccccc1.CCn1c2ccc(Br)cc2c2cc(Br)ccc21.c1ccc2c(c1)[nH]c1ccccc12>>c1ccc(Cn2c3ccc(-n4c5ccccc5c5ccccc54)cc3c3cc(-n4c5ccccc5c5ccccc54)ccc32)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ccd31ce8c37c4c539d85f1eb1d376fda | c1ccc(Cn2c3ccc(-n4c5ccccc5c5ccccc54)cc3c3cc(-n4c5ccccc5c5ccccc54)ccc32)cc1>>c1ccc2c(c1)c1ccccc1n2-c1ccc2[nH]c3ccc(-n4c5ccccc5c5ccccc54)cc3c2c1 | C(C1=CC=CC=C1)N1C2=CC=C(C=C2C=2C=C(C=CC12)N1C2=CC=CC=C2C=2C=CC=CC12)N1C2=CC=CC=C2C=2C=CC=CC12.C(C1=CC=CC=C1)=NC1=CC=CC=C1.CC(C)(C)[O-].[K+].CN(C)C=O>>C1=CC=CC=2C3=CC=CC=C3N(C12)C=1C=CC=2NC3=CC=C(C=C3C2C1)N1C2=CC=CC=C2C=2C=CC=CC12 | c1ccc(C[n:18]2[c:17]3[cH:16][cH:15][c:14](-[n:13]4[c:4]5[cH:3][cH:2][cH:1][cH:6][c:5]5[c:7]5[cH:8][cH:9][cH:10][cH:11][c:12]54)[cH:39][c:38]3[c:37]3[c:19]2[cH:20][cH:21][c:22](-[n:23]2[c:24]4[cH:25][cH:26][cH:27][cH:28][c:29]4[c:30]4[cH:31][cH:32][cH:33][cH:34][c:35]24)[cH:36]3)cc1>>[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6... | c1ccc(Cn2c3ccc(-n4c5ccccc5c5ccccc54)cc3c3cc(-n4c5ccccc5c5ccccc54)ccc32)cc1 | c1ccc2c(c1)c1ccccc1n2-c1ccc2[nH]c3ccc(-n4c5ccccc5c5ccccc54)cc3c2c1 | null | null | O | Deprotection | OtherReaction | 7beaeb5e8d544e73acb5549656e8ff8555d9056c662a5379e0672bee29630470 | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | c1ccc2c(c1)c1ccccc1n2-c1ccc2[nH]c3ccc(-n4c5ccccc5c5ccccc54)cc3c2c1 | [c:1]:[c:2]1:[c:3]:[c:4]:[c:5](:[c:6]):[n;H0;D3;+0:7]:1-C-c1:c:c:c:c:c:1>>[c:1]:[c:2]1:[c:3]:[c:4]:[c:5](:[c:6]):[nH;D2;+0:7]:1 | 29 | [{"value": 29.0, "product": "C1=CC=CC=2C3=CC=CC=C3N(C12)C=1C=CC=2NC3=CC=C(C=C3C2C1)N1C2=CC=CC=C2C=2C=CC=CC12", "details": "PERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 4 | HOUR | Under a nitrogen atmosphere, a suspension of N-benzyl-3,6-di(N-carbazolyl)carbazole (2.06 g, 3.5 mmol), benzylideneaniline (1.27 g, 7.0 mmol) and t-BuOK (5.06 g, 50 mmol) in a dried DMF (30 mL) was stirred at 75° C. for 4 hours. Water (about 150 mL) was added and black tar precipitated was filtrated. The tar-like mater... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccc2[nH]c3ccccc3c2c1 | c1ccc2c(c1)[nH]c1ccccc12 | c1ccc2c(c1)[nH]c1ccccc12.c1ccc2c(c1)[nH]c1ccccc12.c1ccc2c(c1)[nH]c1ccccc12 | Other | O | 75 | 4 | c1ccc(Cn2c3ccc(-n4c5ccccc5c5ccccc54)cc3c3cc(-n4c5ccccc5c5ccccc54)ccc32)cc1>O>c1ccc2c(c1)c1ccccc1n2-c1ccc2[nH]c3ccc(-n4c5ccccc5c5ccccc54)cc3c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-74595d644a4844adad19f7fb8c738d76 | Cc1cc(CO)c(O)c(CO)c1.O=Cc1ccccc1O.O=P(O)(O)O>>Cc1cc(Cc2ccc(O)c(C=O)c2)c(O)c(Cc2ccc(O)c(C=O)c2)c1 | OCC1=C(C(=CC(=C1)C)CO)O.C(C=1C(O)=CC=CC1)=O.P(O)(O)(O)=O>>C(=O)C=1C=C(C=CC1O)CC=1C(=C(C=C(C1)C)CC=1C=CC(=C(C=O)C1)O)O | O[CH2:5][c:4]1[cH:3][c:2]([CH3:1])[cH:28][c:17]([CH2:18][OH:26])[c:15]1[OH:16].[cH:6]1[cH:7][cH:8][c:9]([OH:10])[c:11]([CH:12]=[O:13])[cH:14]1.O=P(O)(O)[OH:23]>>[CH3:1][c:2]1[cH:3][c:4]([CH2:5][c:6]2[cH:7][cH:8][c:9]([OH:10])[c:11]([CH:12]=[O:13])[cH:14]2)[c:15]([OH:16])[c:17]([CH2:18][c:19]2[cH:20][cH:21][c:22]([OH:23... | Cc1cc(CO)c(O)c(CO)c1.O=Cc1ccccc1O.O=P(O)(O)O | Cc1cc(Cc2ccc(O)c(C=O)c2)c(O)c(Cc2ccc(O)c(C=O)c2)c1 | null | null | C(C(C)C)C(=O)C | Aromatic Heterocycle Formation | OtherReaction | a0fa87174406fa2748864dc1882f82ea0817d0bf550bca63e97cce6c339a8765 | 663472b104eb80269572ac046949a2005a065bc8a80774ef43e5e73c537ab953 | c1ccc(Cc2cccc(Cc3ccccc3)c2)cc1 | O-P(-O)(=O)-[OH;D1;+0:1].O-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]:[c:6](-[CH2;D2;+0:7]-[OH;D1;+0:8]):[c:9].[O;D1;H0:10]=[C:11]-[c:12]:[c:13]:[cH;D2;+0:14]:[c:15]:[c:16]>>[O;D1;H0:10]=[C:11]-[c:12]:[c:13]:[c;H0;D3;+0:14](-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]:[c:6](-[CH2;D2;+0:7]-[c:17]1:[c:18]:[c:19]:[c:20](-[OH;D1;+0:1]):[c:21... | 47.7 | [{"value": 47.7, "product": "C(=O)C=1C=C(C=CC1O)CC=1C(=C(C=C(C1)C)CC=1C=CC(=C(C=O)C1)O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Under an atmosphere of nitrogen, 244.0 g (2.0 mol) of salicylaldehyde was weighed into a four-neck flask with a capacity of 1 liter fitted with a reflux condenser, a thermometer and a stirrer, and 244.0 g of a 75% aqueous solution of phosphoric acid was then added dropwise to the flask over a period of 30 minutes and s... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Primary alcohol | Aldehyde.Aromatic alcohol | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C(C(C)C)C(=O)C | null | null | Cc1cc(CO)c(O)c(CO)c1.O=Cc1ccccc1O.O=P(O)(O)O>C(C(C)C)C(=O)C>Cc1cc(Cc2ccc(O)c(C=O)c2)c(O)c(Cc2ccc(O)c(C=O)c2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4dfb463b99444444863b23ce4c1004a4 | O=C(O)c1ccccc1C(=O)O.Oc1ccc(Br)c(O)c1>>O=C(O)c1ccccc1C(=O)c1cc(Br)c(O)cc1O | [Cl-].[Al+3].[Cl-].[Cl-].C1(C=2C(C(=O)O1)=CC=CC2)=O.C(C=1C(C(=O)O)=CC=CC1)(=O)O.BrC1=C(C=C(O)C=C1)O>>BrC=1C(=CC(=C(C(=O)C2=C(C(=O)O)C=CC=C2)C1)O)O | O[C:10]([c:9]1[c:4]([C:2](=[O:1])[OH:3])[cH:5][cH:6][cH:7][cH:8]1)=[O:11].[cH:12]1[cH:13][c:14]([Br:15])[c:16]([OH:17])[cH:18][c:19]1[OH:20]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[C:10](=[O:11])[c:12]1[cH:13][c:14]([Br:15])[c:16]([OH:17])[cH:18][c:19]1[OH:20] | O=C(O)c1ccccc1C(=O)O.Oc1ccc(Br)c(O)c1 | O=C(O)c1ccccc1C(=O)c1cc(Br)c(O)cc1O | null | null | ClCCl.ClCC(Cl)(Cl)Cl.C(C)(=O)OCC.[N+](=O)([O-])C | C-C Coupling | Friedel-Crafts acylation | c192095061656f3fd26b35f75625f8f38ff1c48733635e4bb5643912a6b658c7 | a49756d2995b35bf1c4b6840928f031562470ef5bd676447fb43ce2575147daa | O=C(c1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]-[C:6](=[O;D1;H0:7])-[O;D1;H1:8].[O;D1;H1:9]-[c:10](:[c:11]):[cH;D2;+0:12]:[c:13]:[c:14]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[c:3](:[c:4]):[c:5]-[C:6](=[O;D1;H0:7])-[O;D1;H1:8])-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:10](-[O;D1;H1:9]):[c:11] | null | [] | null | null | 2 | HOUR | Aluminum chloride (8.48 g, 64 mmol) was added to a stirring suspension of phthalic anhydride (2.36 g, 16 mmol) in tetrachloroethane (40 mL) under nitrogen. Nitromethane (6 mL) was added to dissolve the reactants. 4-Bromoresorcinol (3 g, 16 mmol) was added and the mixture continued to stir under nitrogen. The reaction w... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | ClCCl.ClCC(Cl)(Cl)Cl.C(C)(=O)OCC.[N+](=O)([O-])C | null | 2 | O=C(O)c1ccccc1C(=O)O.Oc1ccc(Br)c(O)c1>ClCCl.ClCC(Cl)(Cl)Cl.C(C)(=O)OCC.[N+](=O)([O-])C>O=C(O)c1ccccc1C(=O)c1cc(Br)c(O)cc1O |
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