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-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f5ef483caa0240adbbfeffbf134b4a0e | CC(C)(C)OC(=O)[C@@H]1CSC(Cc2ccccc2)N1C(=O)OC(C)(C)C>>CC(C)(C)OC(=O)[C@@H]1CSC(Cc2ccccc2)N1 | I[Si](C)(C)C.C(C)(C)(C)OC(=O)N1C(SC[C@H]1C(=O)OC(C)(C)C)CC1=CC=CC=C1.O>>C(C1=CC=CC=C1)C1SC[C@H](N1)C(=O)OC(C)(C)C | CC(C)(C)OC(=O)[N:19]1[C@H:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][S:10][CH:11]1[CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[C@@H:8]1[CH2:9][S:10][CH:11]([CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[NH:19]1 | CC(C)(C)OC(=O)[C@@H]1CSC(Cc2ccccc2)N1C(=O)OC(C)(C)C | CC(C)(C)OC(=O)[C@@H]1CSC(Cc2ccccc2)N1 | null | null | C(Cl)(Cl)Cl | Reduction | Boc amine deprotection | f43a6818a2dad1b74fffb8578c65ec32e6a9ffddc1d934cb7e8e04a9995976d0 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(CC2NCCS2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2](-[C:3])-[#16:4]-[C:5]-[C:6]-1-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[C;D1;H3:13]>>[C:3]-[C:2]1-[#16:4]-[C:5]-[C:6](-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[C;D1;H3:13])-[NH;D2;+0:1]-1 | 111.3 | [{"value": 111.3, "product": "C(C1=CC=CC=C1)C1SC[C@H](N1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | C tert-Butyl (2RS,4R)-2-benzyl-4-thiazolidinecarboxalate may be prepared in the following 11.8 cm3 of iodotrimethyl-silane are introduced slowly at a temperature in the region of 25° C. into a solution of 30.5 g of tert-butyl (4R)-3-tert-butoxycarbonyl-2-benzyl-4-thiazolidine-carboxylate (isomer A) in 250 cm3 of chloro... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CSC[NH]1 | C1CSCN1 | C1CSCN1.c1ccccc1 | HO- | C(Cl)(Cl)Cl | null | 1 | CC(C)(C)OC(=O)[C@@H]1CSC(Cc2ccccc2)N1C(=O)OC(C)(C)C>C(Cl)(Cl)Cl>CC(C)(C)OC(=O)[C@@H]1CSC(Cc2ccccc2)N1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-0864c7b521d14d7eb031a94545d74b0f | O=C(O)C1CSC(Cc2ccccc2)N1>>O=C(O)[C@@H]1CSC(Cc2ccccc2)N1 | C1(=CC=CC=C1)CC=O.C(C1=CC=CC=C1)C1SCC(N1)C(=O)O.N[C@@H](CS)C(=O)O>>C(C1=CC=CC=C1)C1SC[C@H](N1)C(=O)O | [O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][S:6][CH:7]([CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[NH:15]1>>[O:1]=[C:2]([OH:3])[C@@H:4]1[CH2:5][S:6][CH:7]([CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[NH:15]1 | O=C(O)C1CSC(Cc2ccccc2)N1 | O=C(O)[C@@H]1CSC(Cc2ccccc2)N1 | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc(CC2NCCS2)cc1 | null | null | [] | null | null | null | null | F (2RS, 4R) -2-Benzyl-4-thiazolidinecarboxylic acid may be prepared in a manner similar to that described in Example 1E, but starting with 53.7 g of L-cysteine and 56.5 g of phenylacetaldehyde. 75.8 g of (2RS,4R)-2-benzyl-4-thiazolidinecarboxylic acid, melting point 200° C., are thereby obtained.
Conditions: See reacti... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1CSCN1.c1ccccc1 | null | null | null | null | O=C(O)C1CSC(Cc2ccccc2)N1>>O=C(O)[C@@H]1CSC(Cc2ccccc2)N1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ffb54698da8d46458dc9823e743c6180 | CC(C)(C)OC(=O)[C@@H]1CSC(Cc2ccccc2)N1C(=O)CNC(=O)Nc1cccc(CC(=O)OCc2ccccc2)c1>>CC(C)(C)OC(=O)[C@@H]1CSC(Cc2ccccc2)N1C(=O)CNC(=O)Nc1cccc(CC(=O)O)c1 | C(C)(C)(C)OC(=O)[C@H]1N(C(SC1)CC1=CC=CC=C1)C(CNC(NC=1C=C(C=CC1)CC(=O)OCC1=CC=CC=C1)=O)=O.C(=O)[O-].[NH4+]>>C(C)(C)(C)OC(=O)[C@H]1N(C(SC1)CC1=CC=CC=C1)C(CNC(NC=1C=C(C=CC1)CC(=O)O)=O)=O | c1ccc(C[O:35][C:33]([CH2:32][c:31]2[cH:30][cH:29][cH:28][c:27]([NH:26][C:24]([NH:23][CH2:22][C:20]([N:19]3[C@H:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][S:10][CH:11]3[CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)=[O:21])=[O:25])[cH:36]2)=[O:34])cc1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7... | CC(C)(C)OC(=O)[C@@H]1CSC(Cc2ccccc2)N1C(=O)CNC(=O)Nc1cccc(CC(=O)OCc2ccccc2)c1 | CC(C)(C)OC(=O)[C@@H]1CSC(Cc2ccccc2)N1C(=O)CNC(=O)Nc1cccc(CC(=O)O)c1 | null | [Pd] | null | Deprotection | Ester saponification (alkyl deprotection) | 86a971d3e4f88009ab4c98512e9f1deb51b2f0ce5cbd068cc61ae878c1e58e2a | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(NCC(=O)N1CCSC1Cc1ccccc1)Nc1ccccc1 | [C:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-C-c1:c:c:c:c:c:1>>[C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4] | 48.3 | [{"value": 48.3, "product": "C(C)(C)(C)OC(=O)[C@H]1N(C(SC1)CC1=CC=CC=C1)C(CNC(NC=1C=C(C=CC1)CC(=O)O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure is similar to that described in Example 1, but starting with 2.58 g of benzyl (4R)-3-{3-[2-(4-tert-butoxycarbonyl-2-benzyl-3-thiazolidinyl)-2-oxoethyl]ureido}phenylacetate (isomer A) , 1.6 g of ammonium formate and 1.3 g of palladium on charcoal (10% Pd). 1.06 g of (4R) -3-{3-[2-(4-tert-butoxycarbonyl-2-b... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | c1ccccc1 | null | C1CSC[NH]1.c1ccccc1.c1ccccc1 | Other | [Pd] | null | null | CC(C)(C)OC(=O)[C@@H]1CSC(Cc2ccccc2)N1C(=O)CNC(=O)Nc1cccc(CC(=O)OCc2ccccc2)c1>[Pd]>CC(C)(C)OC(=O)[C@@H]1CSC(Cc2ccccc2)N1C(=O)CNC(=O)Nc1cccc(CC(=O)O)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e2c9b42b51d54157a9085a6f40b8120e | COC(=O)Cc1cccc(NC(=O)NCC(=O)N2C(C3CC4C=CC3C4)SC[C@H]2C(=O)OC(C)(C)C)c1>>CC(C)(C)OC(=O)[C@@H]1CSC(C2CC3C=CC2C3)N1C(=O)CNC(=O)Nc1cccc(CC(=O)O)c1 | C(C)(C)(C)OC(=O)[C@H]1N(C(SC1)C1C2C=CC(C1)C2)C(CNC(NC=2C=C(C=CC2)CC(=O)OC)=O)=O.[OH-].[K+]>>C(C)(C)(C)OC(=O)[C@H]1N(C(SC1)C1C2C=CC(C1)C2)C(CNC(NC=2C=C(C=CC2)CC(=O)O)=O)=O | C[O:35][C:33]([CH2:32][c:31]1[cH:30][cH:29][cH:28][c:27]([NH:26][C:24]([NH:23][CH2:22][C:20]([N:19]2[C@H:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][S:10][CH:11]2[CH:12]2[CH2:13][CH:14]3[CH:15]=[CH:16][CH:17]2[CH2:18]3)=[O:21])=[O:25])[cH:36]1)=[O:34]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[C@... | COC(=O)Cc1cccc(NC(=O)NCC(=O)N2C(C3CC4C=CC3C4)SC[C@H]2C(=O)OC(C)(C)C)c1 | CC(C)(C)OC(=O)[C@@H]1CSC(C2CC3C=CC2C3)N1C(=O)CNC(=O)Nc1cccc(CC(=O)O)c1 | null | null | null | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(NCC(=O)N1CCSC1C1CC2C=CC1C2)Nc1ccccc1 | 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] | 5.1 | [{"value": 5.1, "product": "C(C)(C)(C)OC(=O)[C@H]1N(C(SC1)C1C2C=CC(C1)C2)C(CNC(NC=2C=C(C=CC2)CC(=O)O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure is as in Example 4, but starting with 0.6 g of methyl (4R)-3-[3-{2-[4-tert-butoxycarbonyl-2-[(2RS)-5-norbornen-2-yl]-3-thiazolidinyl]-2-oxoethyl}ureido]phenylacetate (mixture of isomers C and D) and 0.074 g of potassium hydroxide. 0.03 g of (4R) -3- [3-{2-[4-tert-butoxycarbonyl-2-[(2RS) -5-norbornen-2-yl]... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CSC[NH]1.C1=CC2CCC1C2.c1ccccc1 | Other | null | null | null | COC(=O)Cc1cccc(NC(=O)NCC(=O)N2C(C3CC4C=CC3C4)SC[C@H]2C(=O)OC(C)(C)C)c1>>CC(C)(C)OC(=O)[C@@H]1CSC(C2CC3C=CC2C3)N1C(=O)CNC(=O)Nc1cccc(CC(=O)O)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-73543e7f76764526bdad67044d707af0 | CC(C)(C)OC(=O)NCC(=O)N1C(C2CC3C=CC2C3)SC[C@H]1C(=O)OC(C)(C)C>>CC(C)(C)OC(=O)[C@@H]1CSC(C2CC3C=CC2C3)N1C(=O)CN | C12C(CC(C=C1)C2)C2SCC(N2)C(=O)[O-].C(C)(C)(C)OC(=O)NCC(=O)N1C(SC[C@H]1C(=O)OC(C)(C)C)C1C2C=CC(C1)C2.I[Si](C)(C)C>>NCC(=O)N1C(SC[C@H]1C(=O)OC(C)(C)C)C1C2C=CC(C1)C2 | CC(C)(C)OC(=O)[NH:23][CH2:22][C:20]([N:19]1[C@H:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][S:10][CH:11]1[CH:12]1[CH2:13][CH:14]2[CH:15]=[CH:16][CH:17]1[CH2:18]2)=[O:21]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[C@@H:8]1[CH2:9][S:10][CH:11]([CH:12]2[CH2:13][CH:14]3[CH:15]=[CH:16][CH:17]2[CH2:18]... | CC(C)(C)OC(=O)NCC(=O)N1C(C2CC3C=CC2C3)SC[C@H]1C(=O)OC(C)(C)C | CC(C)(C)OC(=O)[C@@H]1CSC(C2CC3C=CC2C3)N1C(=O)CN | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | C1=CC2CC1CC2C1NCCS1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[#7:5](-[C:6]-[#16:7])-[C:8]-[C:9](-[#8:10])=[O;D1;H0:11]>>[#16:7]-[C:6]-[#7:5](-[C:3](=[O;D1;H0:4])-[C:2]-[NH2;D1;+0:1])-[C:8]-[C:9](-[#8:10])=[O;D1;H0:11] | 99.8 | [{"value": 99.8, "product": "NCC(=O)N1C(SC[C@H]1C(=O)OC(C)(C)C)C1C2C=CC(C1)C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | tert-Butyl (4R)-3-2-aminoacetyl)-2-[(2RS)-5-norbornen-2-yl]-4-thiazolidinecarboxylate (mixture of isomers C and D) may be prepared in a manner similar to that described in Example 1B, but starting with 1.0 g of tert-butyl (4R)-3-(2-tert-butoxycarbonylaminoacetyl)-2-[(2RS)-5-norbornen-2-yl]-4-thiazolidinecarboxylate (mi... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | C1CSC[NH]1.C1=CC2CCC1C2 | HO- | null | null | null | CC(C)(C)OC(=O)NCC(=O)N1C(C2CC3C=CC2C3)SC[C@H]1C(=O)OC(C)(C)C>>CC(C)(C)OC(=O)[C@@H]1CSC(C2CC3C=CC2C3)N1C(=O)CN |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e052a83f32a340ebb3ba8deb4770dd4e | CC(C)(C)OC(=O)[C@@H]1CSC(C2CC3C=CC2C3)N1C(=O)CNC(=O)Nc1cccc(CC(=O)OCc2ccccc2)c1>>CC(C)(C)OC(=O)[C@@H]1CSC(C2CC3CCC2C3)N1C(=O)CNC(=O)Nc1cccc(CC(=O)O)c1 | C(C)(C)(C)OC(=O)[C@H]1N(C(SC1)C1C2C=CC(C1)C2)C(CNC(NC=2C=C(C=CC2)CC(=O)OCC2=CC=CC=C2)=O)=O.C(=O)[O-].[NH4+]>>C(C)(C)(C)OC(=O)[C@H]1N(C(SC1)C1C2CCC(C1)C2)C(CNC(NC=2C=C(C=CC2)CC(=O)O)=O)=O | c1ccc(C[O:35][C:33]([CH2:32][c:31]2[cH:30][cH:29][cH:28][c:27]([NH:26][C:24]([NH:23][CH2:22][C:20]([N:19]3[C@H:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][S:10][CH:11]3[CH:12]3[CH2:13][CH:14]4[CH:15]=[CH:16][CH:17]3[CH2:18]4)=[O:21])=[O:25])[cH:36]2)=[O:34])cc1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](... | CC(C)(C)OC(=O)[C@@H]1CSC(C2CC3C=CC2C3)N1C(=O)CNC(=O)Nc1cccc(CC(=O)OCc2ccccc2)c1 | CC(C)(C)OC(=O)[C@@H]1CSC(C2CC3CCC2C3)N1C(=O)CNC(=O)Nc1cccc(CC(=O)O)c1 | null | [Pd] | null | Deprotection | OtherReaction | 751cb6466f215f44096f47e9cfe8ba7ab9f935cb00f844009e88b83819ca32d7 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(NCC(=O)N1CCSC1C1CC2CCC1C2)Nc1ccccc1 | [C:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-C-c1:c:c:c:c:c:1.[C:5]1-[C:6]-[C:7]2-[C:8]-[C:9]-1-[CH;D2;+0:10]=[CH;D2;+0:11]-2>>[C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4].[C:5]1-[C:6]-[C:7]2-[C:8]-[C:9]-1-[CH2;D2;+0:10]-[CH2;D2;+0:11]-2 | 41 | [{"value": 41.0, "product": "C(C)(C)(C)OC(=O)[C@H]1N(C(SC1)C1C2CCC(C1)C2)C(CNC(NC=2C=C(C=CC2)CC(=O)O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure is as in Example 1, but starting with 0.2 g of benzyl (4R)-3-[3-{2-[4-tert-butoxycarbonyl-2-[(2RS)-5-norbornen-2-yl]-3-thiazolidinyl]-2-oxoethyl}ureido]phenylacetate (mixture of isomers C and D), 0.13 g of Ammonium formate and 0.2 g of palladium on charcoal (10% Pd). 0.07 g of (4R)-3-[3-{2-[4-tert-butoxyc... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | C1=CC2CCC1C2.c1ccccc1 | C1CC2CCC1C2 | C1CSC[NH]1.C1CC2CCC1C2.c1ccccc1 | Other | [Pd] | null | null | CC(C)(C)OC(=O)[C@@H]1CSC(C2CC3C=CC2C3)N1C(=O)CNC(=O)Nc1cccc(CC(=O)OCc2ccccc2)c1>[Pd]>CC(C)(C)OC(=O)[C@@H]1CSC(C2CC3CCC2C3)N1C(=O)CNC(=O)Nc1cccc(CC(=O)O)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-4bc9a35c6a6d473b92f6f84258e723b3 | CCCCC1SC[C@@H](C(=O)OC(C)(C)C)N1C(=O)CN.Cc1cccc(N=C=O)c1>>CCCCC1SC[C@@H](C(=O)OC(C)(C)C)N1C(=O)CNC(=O)Nc1cccc(C)c1 | NCC(=O)N1C(SC[C@H]1C(=O)OC(C)(C)C)CCCC.CC=1C=C(C=CC1)N=C=O>>CC=1C=C(C=CC1)NC(NCC(=O)N1C(SC[C@H]1C(=O)OC(C)(C)C)CCCC)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[S:6][CH2:7][C@@H:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[N:16]1[C:17](=[O:18])[CH2:19][NH2:20].[C:21](=[O:22])=[N:23][c:24]1[cH:25][cH:26][cH:27][c:28]([CH3:29])[cH:30]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[S:6][CH2:7][C@@H:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([... | CCCCC1SC[C@@H](C(=O)OC(C)(C)C)N1C(=O)CN.Cc1cccc(N=C=O)c1 | CCCCC1SC[C@@H](C(=O)OC(C)(C)C)N1C(=O)CNC(=O)Nc1cccc(C)c1 | null | null | null | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCC(=O)N1CCSC1)Nc1ccccc1 | [#16:1]-[C:2]-[#7:3](-[C:4](=[O;D1;H0:5])-[C:6]-[NH2;D1;+0:7])-[C:8]-[C:9](-[#8:10])=[O;D1;H0:11].[O;D1;H0:12]=[C;H0;D2;+0:13]=[N;H0;D2;+0:14]-[c:15](:[c:16]):[c:17]>>[#16:1]-[C:2]-[#7:3](-[C:4](=[O;D1;H0:5])-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:13](=[O;D1;H0:12])-[NH;D2;+0:14]-[c:15](:[c:16]):[c:17])-[C:8]-[C:9](-[#8:10])=[... | 46.3 | [{"value": 46.3, "product": "CC=1C=C(C=CC1)NC(NCC(=O)N1C(SC[C@H]1C(=O)OC(C)(C)C)CCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure is similar to that described in Example 1A, but starting with 1.2 g of tert-butyl (4R)-3-(2-aminoacetyl)-2-butyl-4-thiazolidinecarboxylate (isomer A) and 0.53 g of 3-methylphenyl isocyanate. The crude product is purified by chromatography on silica [eluent: diisopropyl ether/ethyl acetate (95:5 by volume)... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | C1CSC[NH]1.c1ccccc1 | null | null | null | null | CCCCC1SC[C@@H](C(=O)OC(C)(C)C)N1C(=O)CN.Cc1cccc(N=C=O)c1>>CCCCC1SC[C@@H](C(=O)OC(C)(C)C)N1C(=O)CNC(=O)Nc1cccc(C)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e00d18b187a74148a66e17d1bf97c616 | CCCCC1SC[C@@H](C(=O)OC(C)(C)C)N1C(=O)CNC(=O)Nc1cccc(C(=O)OCc2ccccc2)c1>>CCCCC1SC[C@@H](C(=O)OC(C)(C)C)N1C(=O)CNC(=O)Nc1cccc(C(=O)O)c1 | C(C)(C)(C)OC(=O)[C@H]1N(C(SC1)CCCC)C(CNC(NC=1C=C(C(=O)OCC2=CC=CC=C2)C=CC1)=O)=O.C(=O)[O-].[NH4+]>>C(C)(C)(C)OC(=O)[C@H]1N(C(SC1)CCCC)C(CNC(NC=1C=C(C(=O)O)C=CC1)=O)=O | c1ccc(C[O:31][C:29]([c:28]2[cH:27][cH:26][cH:25][c:24]([NH:23][C:21]([NH:20][CH2:19][C:17]([N:16]3[CH:5]([CH2:4][CH2:3][CH2:2][CH3:1])[S:6][CH2:7][C@H:8]3[C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:18])=[O:22])[cH:32]2)=[O:30])cc1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[S:6][CH2:7][C@@H:8]([C:9](=[O:10])[O:... | CCCCC1SC[C@@H](C(=O)OC(C)(C)C)N1C(=O)CNC(=O)Nc1cccc(C(=O)OCc2ccccc2)c1 | CCCCC1SC[C@@H](C(=O)OC(C)(C)C)N1C(=O)CNC(=O)Nc1cccc(C(=O)O)c1 | null | [Pd] | CN(C)C=O | Deprotection | Ester saponification (alkyl deprotection) | 86a971d3e4f88009ab4c98512e9f1deb51b2f0ce5cbd068cc61ae878c1e58e2a | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(NCC(=O)N1CCSC1)Nc1ccccc1 | [O;D1;H0:1]=[C:2](-[c:3])-[O;H0;D2;+0:4]-C-c1:c:c:c:c:c:1>>[O;D1;H0:1]=[C:2](-[OH;D1;+0:4])-[c:3] | 25.3 | [{"value": 25.3, "product": "C(C)(C)(C)OC(=O)[C@H]1N(C(SC1)CCCC)C(CNC(NC=1C=C(C(=O)O)C=CC1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure is similar to that described in Example 1, but starting with 1.18 g of benzyl (4R)-3-{3-[2-(4-tert-butoxycarbonyl-2-butyl-3-thiazolidinyl)-2-oxoethyl]ureido}benzoate (isomer A), 0.8 g of ammonium formate and 1.2 g of palladium on charcoal (10% Pd). 0.25 g of (4R) -3-{3- [2- (4-tert-butoxycarbonyl-2-butyl-... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | c1ccccc1 | null | C1CSC[NH]1.c1ccccc1 | Other | [Pd].CN(C)C=O | null | null | CCCCC1SC[C@@H](C(=O)OC(C)(C)C)N1C(=O)CNC(=O)Nc1cccc(C(=O)OCc2ccccc2)c1>[Pd].CN(C)C=O>CCCCC1SC[C@@H](C(=O)OC(C)(C)C)N1C(=O)CNC(=O)Nc1cccc(C(=O)O)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b47779451583489f80b26bac401c4f5d | CC(C)(C)OC(=O)[C@@H]1CS[C@H](c2ccccc2-c2ccccc2)N1C(=O)CNC(=O)Nc1cccc(CC(=O)OCc2ccccc2)c1>>CC(C)(C)OC(=O)[C@@H]1CS[C@H](c2ccccc2-c2ccccc2)N1C(=O)CNC(=O)Nc1cccc(CC(=O)O)c1 | C(C)(C)(C)OC(=O)[C@H]1N([C@H](SC1)C1=C(C=CC=C1)C1=CC=CC=C1)C(CNC(NC=1C=C(C=CC1)CC(=O)OCC1=CC=CC=C1)=O)=O.C(=O)[O-].[NH4+]>>C(C)(C)(C)OC(=O)[C@H]1N([C@H](SC1)C1=C(C=CC=C1)C1=CC=CC=C1)C(CNC(NC=1C=C(C=CC1)CC(=O)O)=O)=O | c1ccc(C[O:40][C:38]([CH2:37][c:36]2[cH:35][cH:34][cH:33][c:32]([NH:31][C:29]([NH:28][CH2:27][C:25]([N:24]3[C@H:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][S:10][C@@H:11]3[c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3-[c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)=[O:26])=[O:30])[cH:41]2)=[O:39])cc1>>[CH3:1][C... | CC(C)(C)OC(=O)[C@@H]1CS[C@H](c2ccccc2-c2ccccc2)N1C(=O)CNC(=O)Nc1cccc(CC(=O)OCc2ccccc2)c1 | CC(C)(C)OC(=O)[C@@H]1CS[C@H](c2ccccc2-c2ccccc2)N1C(=O)CNC(=O)Nc1cccc(CC(=O)O)c1 | null | [Pd] | null | Deprotection | Ester saponification (alkyl deprotection) | 86a971d3e4f88009ab4c98512e9f1deb51b2f0ce5cbd068cc61ae878c1e58e2a | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(NCC(=O)N1CCS[C@@H]1c1ccccc1-c1ccccc1)Nc1ccccc1 | [C:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-C-c1:c:c:c:c:c:1>>[C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4] | 21.3 | [{"value": 21.3, "product": "C(C)(C)(C)OC(=O)[C@H]1N([C@H](SC1)C1=C(C=CC=C1)C1=CC=CC=C1)C(CNC(NC=1C=C(C=CC1)CC(=O)O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure is similar to that described in Example 1, but starting with 1.36 g of benzyl (2R,4R)-3-[3-{2-[4-tert-butoxycarbonyl-2-(2-phenylphenyl)-3-thiazolidinyl]-2-oxoethyl}ureido]phenylacetate, 0.44 g of ammonium formate and 0.6 g of palladium on charcoal (10% Pd). 0.25 g of (2R,4R)-3-[3-{2-[4-tert-butoxycarbonyl... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | c1ccccc1 | null | C1CSC[NH]1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | [Pd] | null | null | CC(C)(C)OC(=O)[C@@H]1CS[C@H](c2ccccc2-c2ccccc2)N1C(=O)CNC(=O)Nc1cccc(CC(=O)OCc2ccccc2)c1>[Pd]>CC(C)(C)OC(=O)[C@@H]1CS[C@H](c2ccccc2-c2ccccc2)N1C(=O)CNC(=O)Nc1cccc(CC(=O)O)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-acb9658cde0548e0a200ac19f404869d | CC(C)(C)OC(=O)C(N)C(=O)N1[C@@H](c2ccccc2-c2ccccc2)SC[C@H]1C(=O)OC(C)(C)C.CC(C)(C)OC(=O)NCC(=O)O>>CC(C)(C)OC(=O)NCC(=O)N1[C@@H](c2ccccc2-c2ccccc2)SC[C@H]1C(=O)OC(C)(C)C | C1(CCCCC1)N=C=NC1CCCCC1.C(C)(C)(C)OC(=O)C(C(=O)N1[C@H](SC[C@H]1C(=O)OC(C)(C)C)C1=C(C=CC=C1)C1=CC=CC=C1)N.C1(=CC=CC=C1)C1=C(C=CC=C1)C1SC[C@H](N1)C(=O)OC(C)(C)C.C(C)(C)(C)OC(=O)NCC(=O)O>>C(C)(C)(C)OC(=O)NCC(=O)N1[C@H](SC[C@H]1C(=O)OC(C)(C)C)C1=C(C=CC=C1)C1=CC=CC=C1 | CC(C)(C)OC(=O)[CH:9]([NH2:8])[C:10](=[O:11])[N:12]1[C@@H:13]([c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2-[c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[S:26][CH2:27][C@H:28]1[C:29](=[O:30])[O:31][C:32]([CH3:33])([CH3:34])[CH3:35].O=C(O)CN[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5]... | CC(C)(C)OC(=O)C(N)C(=O)N1[C@@H](c2ccccc2-c2ccccc2)SC[C@H]1C(=O)OC(C)(C)C.CC(C)(C)OC(=O)NCC(=O)O | CC(C)(C)OC(=O)NCC(=O)N1[C@@H](c2ccccc2-c2ccccc2)SC[C@H]1C(=O)OC(C)(C)C | null | null | null | Protection | OtherReaction | 35d42f1e7ecc8f0be03450644bb70a362f1e1038fcc33f290b2cccc629937aca | fd660e5850eedebb186615721848051bbc41c15a8337b192fa3ead00371112ac | c1ccc(-c2ccccc2[C@@H]2NCCS2)cc1 | C-C(-C)(-C)-O-C(=O)-[CH;D3;+0:1](-[NH2;D1;+0:2])-[C:3](=[O;D1;H0:4])-[#7:5](-[C:6]-[#16:7])-[C:8]-[C:9](-[#8:10])=[O;D1;H0:11].O-C(=O)-C-N-[C;H0;D3;+0:12](=[O;D1;H0:13])-[#8:14]-[C:15](-[C;D1;H3:16])(-[C;D1;H3:17])-[C;D1;H3:18]>>[#16:7]-[C:6]-[#7:5](-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:1]-[NH;D2;+0:2]-[C;H0;D3;+0:12](=[O;D1... | null | [] | null | null | null | null | C tert-Butyl (2R,4R)-3-(2-tert-butoxycarbonyl-aminoacetyl)-2-(2-phenylphenyl)-4-thiazolidinecarboxylate may be prepared in a manner similar to that described in Example 1C, but starting with 5.44 g of tert-butyl (2RS,4R)-2-(2-phenylphenyl)-4-thiazolidinecarboxylate, 2.8 g of 2-tert-butoxycarbonylaminoacetic acid and 3.... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ester.Ether.Primary amine.Boc.Boc | Carbamic ester.Ether.Boc | null | null | C1CSC[NH]1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CC(C)(C)OC(=O)C(N)C(=O)N1[C@@H](c2ccccc2-c2ccccc2)SC[C@H]1C(=O)OC(C)(C)C.CC(C)(C)OC(=O)NCC(=O)O>>CC(C)(C)OC(=O)NCC(=O)N1[C@@H](c2ccccc2-c2ccccc2)SC[C@H]1C(=O)OC(C)(C)C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e580b3e86a874597a7a65767dd4dd35e | CC(C)(C)OC(=O)[C@@H]1CS[C@H](c2ccccc2-c2ccccc2)N1C(=O)CN.Cc1cccc(N=C=O)c1>>Cc1cccc(NC(=O)NCC(=O)N2[C@@H](c3ccccc3-c3ccccc3)SC[C@H]2C(=O)OC(C)(C)C)c1 | NCC(=O)N1[C@H](SC[C@H]1C(=O)OC(C)(C)C)C1=C(C=CC=C1)C1=CC=CC=C1.CC=1C=C(C=CC1)N=C=O>>CC=1C=C(C=CC1)NC(NCC(=O)N1[C@H](SC[C@H]1C(=O)OC(C)(C)C)C1=C(C=CC=C1)C1=CC=CC=C1)=O | [NH2:10][CH2:11][C:12](=[O:13])[N:14]1[C@@H:15]([c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2-[c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[S:28][CH2:29][C@H:30]1[C:31](=[O:32])[O:33][C:34]([CH3:35])([CH3:36])[CH3:37].[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([N:7]=[C:8]=[O:9])[cH:38]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:... | CC(C)(C)OC(=O)[C@@H]1CS[C@H](c2ccccc2-c2ccccc2)N1C(=O)CN.Cc1cccc(N=C=O)c1 | Cc1cccc(NC(=O)NCC(=O)N2[C@@H](c3ccccc3-c3ccccc3)SC[C@H]2C(=O)OC(C)(C)C)c1 | null | null | null | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCC(=O)N1CCS[C@@H]1c1ccccc1-c1ccccc1)Nc1ccccc1 | [#16:1]-[C:2]-[#7:3](-[C:4](=[O;D1;H0:5])-[C:6]-[NH2;D1;+0:7])-[C:8]-[C:9](-[#8:10])=[O;D1;H0:11].[O;D1;H0:12]=[C;H0;D2;+0:13]=[N;H0;D2;+0:14]-[c:15](:[c:16]):[c:17]>>[#16:1]-[C:2]-[#7:3](-[C:4](=[O;D1;H0:5])-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:13](=[O;D1;H0:12])-[NH;D2;+0:14]-[c:15](:[c:16]):[c:17])-[C:8]-[C:9](-[#8:10])=[... | 12.5 | [{"value": 12.5, "product": "CC=1C=C(C=CC1)NC(NCC(=O)N1[C@H](SC[C@H]1C(=O)OC(C)(C)C)C1=C(C=CC=C1)C1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The procedure is similar to that described in Example 1A, but starting with 1.32 g of tert-butyl (2R,4R)-3-(2-aminoacetyl)-2-(2-phenylphenyl)-4-thiazolidinecarboxylate and 0.47 g of 3-methylphenyl isocyanate. The crude product is purified by chromatography on silica [eluent: methylene chloride/ethyl acetate (90:10 by v... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CSC[NH]1 | null | null | null | null | CC(C)(C)OC(=O)[C@@H]1CS[C@H](c2ccccc2-c2ccccc2)N1C(=O)CN.Cc1cccc(N=C=O)c1>>Cc1cccc(NC(=O)NCC(=O)N2[C@@H](c3ccccc3-c3ccccc3)SC[C@H]2C(=O)OC(C)(C)C)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-5ea1469a8e4446d8bece6f8a474dd542 | CON=C(C(=O)OC)c1ccccc1/C=C(\Cl)C(=O)OC(C)(C)C>>CON=C(C(=O)OC)c1ccccc1/C=C(\Cl)C(=O)O | CON=C(C(=O)OC)C1=C(C=CC=C1)\C=C(\C(=O)OC(C)(C)C)/Cl.C([O-])([O-])=O.[Na+].[Na+].C(C)(C)(C)OC>>CON=C(C(=O)OC)C1=C(C=CC=C1)\C=C(\C(=O)O)/Cl | CC(C)(C)[O:20][C:18](/[C:16](=[CH:15]/[c:14]1[c:9]([C:4](=[N:3][O:2][CH3:1])[C:5](=[O:6])[O:7][CH3:8])[cH:10][cH:11][cH:12][cH:13]1)[Cl:17])=[O:19]>>[CH3:1][O:2][N:3]=[C:4]([C:5](=[O:6])[O:7][CH3:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1/[CH:15]=[C:16](\[Cl:17])[C:18](=[O:19])[OH:20] | CON=C(C(=O)OC)c1ccccc1/C=C(\Cl)C(=O)OC(C)(C)C | CON=C(C(=O)OC)c1ccccc1/C=C(\Cl)C(=O)O | null | null | ClCCl.FC(C(=O)O)(F)F | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | c1ccccc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])/[C:4](-[Cl;D1;H0:5])=[C:6]/[c:7]>>[Cl;D1;H0:5]/[C:4](=[C:6]\[c:7])-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 82 | [{"value": 82.0, "product": "CON=C(C(=O)OC)C1=C(C=CC=C1)\\C=C(\\C(=O)O)/Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 29 g of methyl 2-methoxyimino-2-{2-[2-chloro-2-tert-butyloxycarbonyl-(Z)-ethenyl]phenyl}acetate from Example 3 are stirred in a mixture of 40 ml of trifluoroacetic acid and 160 ml of dichloromethane for 2.5 hours at room temperature. The dark solution is then stirred into 500 ml of saturated sodium carbonate solution (... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | c1ccccc1 | Other | ClCCl.FC(C(=O)O)(F)F | null | null | CON=C(C(=O)OC)c1ccccc1/C=C(\Cl)C(=O)OC(C)(C)C>ClCCl.FC(C(=O)O)(F)F>CON=C(C(=O)OC)c1ccccc1/C=C(\Cl)C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d3d3361c405f4232a9008dac1542cd34 | COC(=O)CN=[N+]=[N-].O=Cc1ccc2c(c1)CCO2>>COC(=O)C(=Cc1ccc2c(c1)CCO2)N=[N+]=[N-] | CC(C)([O-])C.[K+].O1CCC2=C1C=CC(=C2)C=O.N(=[N+]=[N-])CC(=O)OC>>COC(C(=CC=1C=CC2=C(CCO2)C1)N=[N+]=[N-])=O | [CH3:1][O:2][C:3](=[O:4])[CH2:5][N:16]=[N+:17]=[N-:18].O=[CH:6][c:7]1[cH:8][cH:9][c:10]2[c:11]([cH:12]1)[CH2:13][CH2:14][O:15]2>>[CH3:1][O:2][C:3](=[O:4])[C:5](=[CH:6][c:7]1[cH:8][cH:9][c:10]2[c:11]([cH:12]1)[CH2:13][CH2:14][O:15]2)[N:16]=[N+:17]=[N-:18] | COC(=O)CN=[N+]=[N-].O=Cc1ccc2c(c1)CCO2 | COC(=O)C(=Cc1ccc2c(c1)CCO2)N=[N+]=[N-] | null | null | CO | C-C Coupling | Aldol condensation | a86984aeb4a9963534e0b081b0ecca18455fda1775f36ce168d1ca4cf966df3e | 203dd34a20dceaf1737adbf20e01b43c2424e4e4b1722d942d1a796d895396e6 | c1ccc2c(c1)CCO2 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH2;D2;+0:9]-[#7:10]=[#7;+:11]=[N;-;D1;H0:12]>>[C;D1;H3:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C;H0;D3;+0:9](-[#7:10]=[#7;+:11]=[N;-;D1;H0:12])=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 94.2 | [{"value": 94.2, "product": "COC(C(=CC=1C=CC2=C(CCO2)C1)N=[N+]=[N-])=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -10 | CELSIUS | 1 | HOUR | To a cold (-10° C.) stirred solution of potassium tert-butoxide (6.06 g) in dry methanol (40 ml) was added dropwise a mixture of 2,3-dihydrobenzofuran-5-carboxaldehyde (2 g) and methyl azidoacetate (6.21 g). The mixture was stirred for 1 h at -10° C. and then stored at 0° C. for 18 h. The resulting pale yellow microcry... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Ester | null | null | c1ccc2c(c1)CCO2 | HO- | CO | -10 | 1 | COC(=O)CN=[N+]=[N-].O=Cc1ccc2c(c1)CCO2>CO>COC(=O)C(=Cc1ccc2c(c1)CCO2)N=[N+]=[N-] |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-327e2608ec0144c2b599ca59201375d2 | CCOC(CBr)OCC.Nc1cccc2c1CCCO2>>CCOC(CNc1cccc2c1CCCO2)OCC | C(C)OC(CBr)OCC.O1CCCC2=C(C=CC=C12)N.C([O-])([O-])=O.[K+].[K+]>>O1CCCC2=C(C=CC=C12)NCC(OCC)OCC | Br[CH2:5][CH:4]([O:3][CH2:2][CH3:1])[O:17][CH2:18][CH3:19].[NH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[CH2:13][CH2:14][CH2:15][O:16]2>>[CH3:1][CH2:2][O:3][CH:4]([CH2:5][NH:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[CH2:13][CH2:14][CH2:15][O:16]2)[O:17][CH2:18][CH3:19] | CCOC(CBr)OCC.Nc1cccc2c1CCCO2 | CCOC(CNc1cccc2c1CCCO2)OCC | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc2c(c1)CCCO2 | Br-[CH2;D2;+0:1]-[C:2](-[#8:3])-[#8:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[#8:3]-[C:2](-[#8:4])-[CH2;D2;+0:1]-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | 100 | CELSIUS | null | null | Bromoacetaldehyde diethyl acetal (11.8 ml) was added to a mixture of chroman-5-yl-amine (5.85 g) (prepared according to J. Heterocyclic Chem., (1973), Vol 10 (4) page 623), and potassium carbonate (10.84 g) in dry DMF (70 ml) at room temperature under N2. The mixture was heated at 100° C. for 60 h. The cooled mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccc2c(c1)CCCO2 | HBr | CN(C)C=O | 100 | null | CCOC(CBr)OCC.Nc1cccc2c1CCCO2>CN(C)C=O>CCOC(CNc1cccc2c1CCCO2)OCC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-83e005a4175642fe9afc52764d88855b | CCOC(CBr)OCC.Nc1cccc2c1CCO2>>CCOC(CNc1cccc2c1CCO2)OCC | O1CCC2=C1C=CC=C2N.C([O-])([O-])=O.[K+].[K+].C(C)OC(CBr)OCC>>C(C)OC(CNC1=CC=CC2=C1CCO2)OCC | Br[CH2:5][CH:4]([O:3][CH2:2][CH3:1])[O:16][CH2:17][CH3:18].[NH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[CH2:13][CH2:14][O:15]2>>[CH3:1][CH2:2][O:3][CH:4]([CH2:5][NH:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[CH2:13][CH2:14][O:15]2)[O:16][CH2:17][CH3:18] | CCOC(CBr)OCC.Nc1cccc2c1CCO2 | CCOC(CNc1cccc2c1CCO2)OCC | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc2c(c1)CCO2 | Br-[CH2;D2;+0:1]-[C:2](-[#8:3])-[#8:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[#8:3]-[C:2](-[#8:4])-[CH2;D2;+0:1]-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | 100 | CELSIUS | null | null | A mixture of 2,3-dihydro-benzofuran-4-ylamine (preparation. J. Hetereocyclic Chem., 18, 1333 (1980)) (4.34 g), potassium carbonate (8.87 g) and bromo acetaldehyde diethyl acetal (9.7 ml) in dry DMF (60 ml) was heated to 100° C. for 2 days under. The mixture was cooled and was partitioned between water and ethyl acetate... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccc2c(c1)CCO2 | HBr | CN(C)C=O | 100 | null | CCOC(CBr)OCC.Nc1cccc2c1CCO2>CN(C)C=O>CCOC(CNc1cccc2c1CCO2)OCC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-369807e9e22041ffb2a801a6f750a115 | CC(=O)OC(C)=O.c1cc2ccc3c(c2[nH]1)CCO3>>CC(=O)NCCN1CCc2ccc3c(c21)CCO3 | C(C)(=O)OC(C)=O.N1C=CC2=CC=C3C(=C12)CCO3.N1=CC=CC=C1>>N1(CCC2=CC=C3C(=C12)CCO3)CCNC(C)=O | CC(=O)O[C:2]([CH3:1])=[O:3].[cH:6]1[nH:7][c:15]2[c:10]([cH:9]1)[cH:11][cH:12][c:13]1[c:14]2[CH2:16][CH2:17][O:18]1>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][c:10]2[cH:11][cH:12][c:13]3[c:14]([c:15]21)[CH2:16][CH2:17][O:18]3 | CC(=O)OC(C)=O.c1cc2ccc3c(c2[nH]1)CCO3 | CC(=O)NCCN1CCc2ccc3c(c21)CCO3 | null | null | C1CCOC1 | Acylation | OtherReaction | 43dbdc8998fd15afdab1b5d3332fcf7dcf4e1cd3bef06be9df6ebe43daa7c853 | a1f7403337b0cb17f86436f8a329ecbaeddd4f0fb6dc049f1812ab8355b89185 | c1cc2c(c3c1CCN3)CCO2 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[c:4]:[c:5]1:[cH;D2;+0:6]:[cH;D2;+0:7]:[nH;D2;+0:8]:[c:9]:1:[c:10]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[#7:11]-[C:12]-[CH2;D2;+0:7]-[N;H0;D3;+0:8]1-[C:13]-[CH2;D2;+0:6]-[c:5](:[c:4]):[c:9]-1:[c:10] | null | [] | null | null | null | null | To a stirred solution of Intermediate 7 (77 mg) in dry THF (5 ml) containing pyridine (0.09 ml) was added acetic anhydride (0.06 ml). After 18 h at 20° C. the mixture was partitioned between 2N Na2CO3 (30 ml) and EtOAc (2×30 ml). The dried extracts were evaporated and the residue chromatographed on silica gel (20 g). E... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | Secondary amide.Tertiary amine | c1cc2ccc3c(c2[nH]1)CCO3 | c1cc2c(c3c1CC[NH]3)CCO2 | c1cc2c(c3c1CC[NH]3)CCO2 | Other | C1CCOC1 | null | null | CC(=O)OC(C)=O.c1cc2ccc3c(c2[nH]1)CCO3>C1CCOC1>CC(=O)NCCN1CCc2ccc3c(c21)CCO3 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6f742d84ff9d4b8e8717082162d207dc | Cl>>Cl | N1(CCC2=CC=C3C(=C12)CCO3)CCNC(C)=O.Cl>>Cl.N1(CCC2=CC=C3C(=C12)CCO3)CCNC(C)=O | [ClH:19]>>[ClH:19] | Cl | Cl | null | null | C(C)(=O)OCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | 2 | HOUR | The title compound of Example 3 (334 mg) was dissolved in ethyl acetate (20 ml) and was treated with ethereal HCl (1.35 ml). This was stirred at room temperature for 2 h and then the solvent was evaporated to give the title compound as a pale green powder (383 mg), m.p. 152°-154° C.
Conditions: See reaction.notes.proce... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)(=O)OCC | null | 2 | Cl>C(C)(=O)OCC>Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-dd274f47e9044758accf665671201e6c | CC(=O)NCCCl.CC(C)=O.Nc1cccc2c1CCCO2>>CC(=O)NCCN1CCc2ccc3c(c21)CCO3 | O1CCCC2=C(C=CC=C12)N.[I-].[K+].ClCCNC(C)=O.CC(=O)C>>N1(CCC2=CC=C3C(=C12)CCO3)CCNC(C)=O | Cl[CH2:6][CH2:5][NH:4][C:2]([CH3:1])=[O:3].CC(=O)[CH3:8].[NH2:7][c:15]1[cH:10][cH:11][cH:12][c:13]2[c:14]1[CH2:9][CH2:16][CH2:17][O:18]2>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][c:10]2[cH:11][cH:12][c:13]3[c:14]([c:15]21)[CH2:16][CH2:17][O:18]3 | CC(=O)NCCCl.CC(C)=O.Nc1cccc2c1CCCO2 | CC(=O)NCCN1CCc2ccc3c(c21)CCO3 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 95ab9d697bba91fc1ac3efad48a78c7aefd69c2f6b85a7733edd521a24d73e6b | fedc0382ba58f6b119b2623cb03d1ba36f77720ea27e54609811232a45a383e6 | c1cc2c(c3c1CCN3)CCO2 | C-C(=O)-[CH3;D1;+0:1].Cl-[CH2;D2;+0:2]-[C:3]-[#7:4]-[C:5](-[C;D1;H3:6])=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9]1:[cH;D2;+0:10]:[c:11]:[c:12]:[c:13]2:[c;H0;D3;+0:14]:1-[CH2;D2;+0:15]-[CH2;D2;+0:16]-[C:17]-[#8:18]-2>>[C;D1;H3:6]-[C:5](=[O;D1;H0:7])-[#7:4]-[C:3]-[CH2;D2;+0:2]-[N;H0;D3;+0:8]1-[CH2;D2;+0:1]-[CH2;D2;+0:15]-[c;H0;D3;... | null | [] | null | null | null | null | A mixture of Intermediate 4 (50 mg), potassium iodide (1 g) and N-(2-chloroethyl)acetamide (96 mg) in acetone (5 ml) was heated to reflux for 2 days. The cooled mixture was partitioned between water and ethyl acetate. The extracts were dried, and evaporated, and the residue chromatographed on silica gel. Elution with C... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Primary amine | Tertiary amine | c1ccc2c(c1)CCCO2 | c1cc2c(c3c1CC[NH]3)CCO2 | c1cc2c(c3c1CC[NH]3)CCO2 | HCl | null | null | null | CC(=O)NCCCl.CC(C)=O.Nc1cccc2c1CCCO2>>CC(=O)NCCN1CCc2ccc3c(c21)CCO3 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-cd36f8dd6fc646be8d7824e16eaca0f5 | CCCN(CCC)C1CC2CN(C(=O)c3ccccc3)C3=C2C(C1)C(Br)C=C3>>CCCN(CCC)C1Cc2c(C#N)ccc3c2C(C1)CN3C(=O)c1ccccc1 | C(C1=CC=CC=C1)(=O)N1CC2C=3C(C(C=CC13)Br)CC(C2)N(CCC)CCC.C(#N)[Cu]>>C(C1=CC=CC=C1)(=O)N1CC2C=3C(=C(C=CC13)C#N)CC(C2)N(CCC)CCC | Br[CH:11]1[CH:14]=[CH:15][C:16]2=[C:17]3[CH:10]([CH2:9][CH:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])[CH2:19][CH:18]13)[CH2:20][N:21]2[C:22](=[O:23])[c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[CH:8]1[CH2:9][c:10]2[c:11]([C:12]#[N:13])[cH:14][cH:15][c:16]3[c:... | CCCN(CCC)C1CC2CN(C(=O)c3ccccc3)C3=C2C(C1)C(Br)C=C3 | CCCN(CCC)C1Cc2c(C#N)ccc3c2C(C1)CN3C(=O)c1ccccc1 | null | [Cu]I | O.CN(C)C=O.C(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | b1b7d399944a8d47a218d4a804f2d01edbc5dfec2a79dc868f640aafe591af24 | 13bad28d5b0a0a6678ff3c47616bbe6f1ca115a480d3e72288190f082dcfe4ee | O=C(c1ccccc1)N1CC2CCCc3cccc1c32 | Br-[CH;D3;+0:1]1-[CH;D2;+0:2]=[CH;D2;+0:3]-[C;H0;D3;+0:4]2=[C;H0;D3;+0:5]3-[CH;D3;+0:6](-[C:7]-[C:8]-[C:9]-[CH;D3;+0:10]-3-1)-[CH2;D2;+0:11]-[#7:12]-2-[C:13](=[O;D1;H0:14])-[c:15]>>[N;D1;H0:16]#[C:17]-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[cH;D2;+0:3]:[c;H0;D3;+0:4]2:[c;H0;D3;+0:5]3:[c;H0;D3;+0:6]:1-[C:7]-[C:8]-[C:9]-[CH;D3;+0:... | 82.6 | [{"value": 82.6, "product": "C(C1=CC=CC=C1)(=O)N1CC2C=3C(=C(C=CC13)C#N)CC(C2)N(CCC)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 6 | HOUR | To a solution of (±)-1-benzoyl-6-bromo-4-(di-n-propylamino)hexahydrobenz[cd]indole (5.5 g, 12.5 mmol) in DMF (100 mL) under a N2 atmosphere was added 3.4 g (37.5 mmol) of CuCN and 7.1 g (37.5 mmol) of CuI. The reaction mixture was then stirred at 140° C. for 6 hr. The reaction mixture was poured onto ice, diluted with ... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Secondary halide | Nitrile | C1=CC2=C3C(C1)CCCC3C[NH]2 | c1cc2c3c(c1)[NH]CC3CCC2 | c1cc2c3c(c1)[NH]CC3CCC2.c1ccccc1 | HBr | [Cu]I.O.CN(C)C=O.C(Cl)Cl | 140 | 6 | CCCN(CCC)C1CC2CN(C(=O)c3ccccc3)C3=C2C(C1)C(Br)C=C3>[Cu]I.O.CN(C)C=O.C(Cl)Cl>CCCN(CCC)C1Cc2c(C#N)ccc3c2C(C1)CN3C(=O)c1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-90bc15899b3542d1bd25e6cafd9e8880 | CCCN(CCC)C1Cc2c(C#N)ccc3c2C(C1)CN3C(=O)c1ccccc1>>CCCN(CCC)C1Cc2c(C#N)ccc3c2C(CN3)C1 | Cl.C(CCC)[Li].C(C1=CC=CC=C1)(=O)N1CC2C=3C(=C(C=CC13)C#N)CC(C2)N(CCC)CCC>>C(#N)C1=C2C=3C(CNC3C=C1)CC(C2)N(CCC)CCC | O=C(c1ccccc1)[N:20]1[c:16]2[cH:15][cH:14][c:11]([C:12]#[N:13])[c:10]3[c:17]2[CH:18]([CH2:19]1)[CH2:21][CH:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])[CH2:9]3>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[CH:8]1[CH2:9][c:10]2[c:11]([C:12]#[N:13])[cH:14][cH:15][c:16]3[c:17]2[CH:18]([CH2:19][NH:20]3)[CH2:21... | CCCN(CCC)C1Cc2c(C#N)ccc3c2C(C1)CN3C(=O)c1ccccc1 | CCCN(CCC)C1Cc2c(C#N)ccc3c2C(CN3)C1 | null | null | CCCCCC.C1CCOC1 | Reduction | Hydrogenolysis of tertiary amines | 99f0a6dc5611581d1d7a71900cee1ca5de3aaa1efd3b5fccc3b6d24420f211d3 | 62cf08a8ae6315067a063b5b3495125ccbdaff6b2340ce1d3e1c7b6cde962ae4 | c1cc2c3c(c1)NCC3CCC2 | O=C(-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[c:4]:[c:5]-1:[c:6])-c1:c:c:c:c:c:1>>[c:6]:[c:5]1:[c:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1 | 113.8 | [{"value": 113.8, "product": "C(#N)C1=C2C=3C(CNC3C=C1)CC(C2)N(CCC)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 30 | MINUTE | To a stirred solution of 4.8 g (0.0124 mol) of (±)-1-benzoyl-6-cyano-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole in 200 mL of THF cooled to -78° C. under a N2 atmosphere were added 16 mL (0.025 mol) of a 1.6M solution of n-butyl lithium in hexane. The reaction mixture was stirred at -78° C. for 30 minutes... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Secondary amine | c1ccccc1.c1cc2c3c(c1)[NH]CC3CCC2 | c1cc2c3c(c1)NCC3CCC2 | c1cc2c3c(c1)NCC3CCC2 | HO- | CCCCCC.C1CCOC1 | -78 | 0.5 | CCCN(CCC)C1Cc2c(C#N)ccc3c2C(C1)CN3C(=O)c1ccccc1>CCCCCC.C1CCOC1>CCCN(CCC)C1Cc2c(C#N)ccc3c2C(CN3)C1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-4da5a68747f9476cb34b56f4b3dcbceb | CCCN(CCC)C1Cc2c(C#N)ccc3c2C(CN3)C1>>CCCN(CCC)C1Cc2c(C(C)=O)ccc3c2C(CN3)C1 | C(#N)C1=C2C=3C(CNC3C=C1)CC(C2)N(CCC)CCC.C[Mg]Br.C(C)OCC.[NH4+].[Cl-]>>C(C)(=O)C1=C2C=3C(CNC3C=C1)CC(C2)N(CCC)CCC | N#[C:12][c:11]1[c:10]2[c:18]3[c:17]([cH:16][cH:15]1)[NH:21][CH2:20][CH:19]3[CH2:22][CH:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])[CH2:9]2>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[CH:8]1[CH2:9][c:10]2[c:11]([C:12]([CH3:13])=[O:14])[cH:15][cH:16][c:17]3[c:18]2[CH:19]([CH2:20][NH:21]3)[CH2:22]1 | CCCN(CCC)C1Cc2c(C#N)ccc3c2C(CN3)C1 | CCCN(CCC)C1Cc2c(C(C)=O)ccc3c2C(CN3)C1 | null | null | C1=CC=CC=C1 | Miscellaneous | OtherReaction | 54622de249eb9a5622e28710a02d261b08e09c3ee957106ef84a0e4751ccb30f | 957d5e0aaa82a4f5b73d699040cb2acd7f615417c9e400cbb7a63fa4c133449a | c1cc2c3c(c1)NCC3CCC2 | N#[C;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[C;D1;H3:5]-[C;H0;D3;+0:1](=[O;D1;H0:6])-[c:2](:[c:3]):[c:4] | null | [] | null | null | 30 | MINUTE | A solution of 0.5 g (1.8 mmol) of (±)-6-cyano-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole in 75 mL of benzene was treated with 5 mL of 2.0M methylmagnesium bromide in diethyl ether. The reaction mixture was refluxed for 2 days. The reaction mixture was cooled and excess Grignard reagent was decomposed wit... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Ketone | null | null | c1cc2c3c(c1)NCC3CCC2 | null | C1=CC=CC=C1 | null | 0.5 | CCCN(CCC)C1Cc2c(C#N)ccc3c2C(CN3)C1>C1=CC=CC=C1>CCCN(CCC)C1Cc2c(C(C)=O)ccc3c2C(CN3)C1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-4c6265efbbae45d2a4a86f843d116b35 | CCCN(CCC)C1Cc2c(C(C)=O)ccc3c2C(CN3)C1.O=C(Cl)OCC(Cl)(Cl)Cl>>NC(=O)N1CCc2ccccc21 | C(C)(=O)C1=C2C=3C(CNC3C=C1)CC(C2)N(CCC)CCC.C(C)N(CC)CC.ClC(=O)OCC(Cl)(Cl)Cl>>C(N)(=O)N1CCC2=CC=CC=C12 | CCCN(CCC)C1C[CH:6]2[CH2:5][NH:4][c:12]3[c:7]2[c:8]([c:9](C(C)=O)[cH:10][cH:11]3)C1.ClC(Cl)(Cl)CO[C:2](Cl)=[O:3]>>[NH2:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]21 | CCCN(CCC)C1Cc2c(C(C)=O)ccc3c2C(CN3)C1.O=C(Cl)OCC(Cl)(Cl)Cl | NC(=O)N1CCc2ccccc21 | null | null | C(Cl)Cl | Acylation | OtherReaction | 6a9ab0c72d3ef4f5776b87b216245ab6ebe0245f6ae66f5b216d5863946ee678 | 1fea30f316824198e233dc7d7d5f0ed1a4a322c4c89c24d4336ce38c6250dbb8 | c1ccc2c(c1)CCN2 | C-C-C-N(-C-C-C)-C1-C-[CH;D3;+0:1]2-[C:2]-[NH;D2;+0:3]-[c:4]3:[c:5]:[c:6]:[c;H0;D3;+0:7](-C(-C)=O):[c;H0;D3;+0:8](:[c:9]:3-2)-C-1.Cl-[C;H0;D3;+0:10](=[O;D1;H0:11])-O-C-C(-Cl)(-Cl)-Cl>>[N;D1;H2:12]-[C;H0;D3;+0:10](=[O;D1;H0:11])-[N;H0;D3;+0:3]1-[C:2]-[CH2;D2;+0:1]-[c:9]2:[cH;D2;+0:8]:[cH;D2;+0:7]:[c:6]:[c:5]:[c:4]:2-1 | null | [] | null | null | 1 | HOUR | To a solution of (±)-6-acetyl-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole (2.3 g, 7.7 mmol) and triethylamine (1.1 ml, 8 mmol) in 90 ml CH2Cl2 under N2 was added dropwise a solution of 2,2,2-trichloroethyl chloroformate. The reaction mixture was stirred at room temperature for 1 hr. The CH2Cl2 solution wa... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Trichloro group.Ketone.Ether.Secondary amine.Tertiary amine | Urea | c1cc2c3c(c1)NCC3CCC2 | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | HCl | C(Cl)Cl | null | 1 | CCCN(CCC)C1Cc2c(C(C)=O)ccc3c2C(CN3)C1.O=C(Cl)OCC(Cl)(Cl)Cl>C(Cl)Cl>NC(=O)N1CCc2ccccc21 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a9838402e244479d887e1b79c36d8441 | CCCN(CCC)[C@H]1Cc2c(C(C)=O)ccc3c2[C@@H](CN3)C1.O=C(Cl)OCC(Cl)(Cl)Cl>>NC(=O)N1CCc2ccccc21 | C(C)(=O)C1=C2C=3[C@@H](CNC3C=C1)C[C@H](C2)N(CCC)CCC.C(C)N(CC)CC.ClC(=O)OCC(Cl)(Cl)Cl>>C(N)(=O)N1CCC2=CC=CC=C12 | CCCN(CCC)[C@@H]1C[C@@H:6]2[CH2:5][NH:4][c:12]3[c:7]2[c:8]([c:9](C(C)=O)[cH:10][cH:11]3)C1.ClC(Cl)(Cl)CO[C:2](Cl)=[O:3]>>[NH2:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]21 | CCCN(CCC)[C@H]1Cc2c(C(C)=O)ccc3c2[C@@H](CN3)C1.O=C(Cl)OCC(Cl)(Cl)Cl | NC(=O)N1CCc2ccccc21 | null | null | C(Cl)Cl | Acylation | OtherReaction | 225a7c62dff362372b072d49673129934807b8d7bc79257f934cb235926ab1cb | 1fea30f316824198e233dc7d7d5f0ed1a4a322c4c89c24d4336ce38c6250dbb8 | c1ccc2c(c1)CCN2 | null | 270.4 | [{"value": 270.4, "product": "C(N)(=O)N1CCC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of (+)(2aS,4R)-6-acetyl-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole (1.7 g, 5.7 mmol) and triethylamine (0.8 ml, 6 mmol) in 90 ml CH2Cl2 was added dropwise a solution of 2,2,2-trichloroethyl chloroformate (1.3 g, 6 mmol) in 10 ml CH2Cl2. The reaction mixture was stirred at room temperature f... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Trichloro group.Ketone.Ether.Secondary amine.Tertiary amine | Urea | c1cc2c3c(c1)NC[C@H]3CCC2 | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | HCl | C(Cl)Cl | null | 1 | CCCN(CCC)[C@H]1Cc2c(C(C)=O)ccc3c2[C@@H](CN3)C1.O=C(Cl)OCC(Cl)(Cl)Cl>C(Cl)Cl>NC(=O)N1CCc2ccccc21 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-06c509707e6944338237e366af75ab71 | CCCN(CCC)[C@@H]1Cc2c(I)ccc3c2[C@@H](C1)CN3C(=O)c1ccccc1.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ncco1>>CCCN(CCC)[C@@H]1Cc2c(-c3ncco3)ccc3c2[C@@H](C1)CN3C(=O)c1ccccc1 | C(CCC)[Sn](C=1OC=CN1)(CCCC)CCCC.C(C1=CC=CC=C1)(=O)N1C[C@H]2C=3C(=C(C=CC13)I)C[C@H](C2)N(CCC)CCC>>C(C1=CC=CC=C1)(=O)N1C[C@H]2C=3C(=C(C=CC13)C=1OC=CN1)C[C@H](C2)N(CCC)CCC | I[c:11]1[c:10]2[c:20]3[c:19]([cH:18][cH:17]1)[N:24]([C:25](=[O:26])[c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1)[CH2:23][C@@H:21]3[CH2:22][C@H:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])[CH2:9]2.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:12]1[n:13][cH:14][cH:15][o:16]1>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7]... | CCCN(CCC)[C@@H]1Cc2c(I)ccc3c2[C@@H](C1)CN3C(=O)c1ccccc1.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ncco1 | CCCN(CCC)[C@@H]1Cc2c(-c3ncco3)ccc3c2[C@@H](C1)CN3C(=O)c1ccccc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C1(=CC=CC=C1)C | C-C Coupling | Stille reaction_aryl | 42596528f1dffb674d4997eac8515a130029c7feafaf2f052b8fa314683b7946 | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | O=C(c1ccccc1)N1C[C@@H]2CCCc3c(-c4ncco4)ccc1c32 | C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#8;a:5]:1.I-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](:[c:10])-[C:11]>>[C:11]-[c:9](:[c:10]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#8;a:5]:1):[c:7]:[c:8] | 67.5 | [{"value": 67.5, "product": "C(C1=CC=CC=C1)(=O)N1C[C@H]2C=3C(=C(C=CC13)C=1OC=CN1)C[C@H](C2)N(CCC)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 5.0 g (13.8 mmol) of the crude 2-tributylstannyloxazole prepared above and 6.8 g (13.9 mmol) of (+)(2aR,4S)-1-benzoyl-6-iodo-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole in 100 ml of toluene was treated with 0.7 g (0.6 mmol) of tetrakis(triphenylphosphine)palladium then refluxed under nitroge... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1cc2c3c(c1)[NH]C[C@@H]3CCC2.c1cocn1 | c1cocn1.c1cc2c3c(c1)[NH]C[C@@H]3CCC2 | c1cocn1.c1cc2c3c(c1)[NH]C[C@@H]3CCC2.c1ccccc1 | HI.Sn | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C | null | null | CCCN(CCC)[C@@H]1Cc2c(I)ccc3c2[C@@H](C1)CN3C(=O)c1ccccc1.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ncco1>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>CCCN(CCC)[C@@H]1Cc2c(-c3ncco3)ccc3c2... |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ac7194da57c94ba59ea021918cf5a3f6 | CC(=O)c1ccc2c3c1C[C@@H](N(CC1CC1)CC1CC1)C[C@H]3CN2.O=C(Cl)OCC(Cl)(Cl)Cl>>NC(=O)N1CCc2ccccc21 | C(C)(=O)C1=C2C=3[C@H](CNC3C=C1)C[C@@H](C2)N(CC2CC2)CC2CC2.C(C)N(CC)CC.ClC(COC(=O)Cl)(Cl)Cl>>C(N)(=O)N1CCC2=CC=CC=C12 | CC(=O)[c:9]1[c:8]2[c:7]3[c:12]([cH:11][cH:10]1)[NH:4][CH2:5][C@@H:6]3C[C@H](N(CC1CC1)CC1CC1)C2.ClC(Cl)(Cl)CO[C:2](Cl)=[O:3]>>[NH2:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]21 | CC(=O)c1ccc2c3c1C[C@@H](N(CC1CC1)CC1CC1)C[C@H]3CN2.O=C(Cl)OCC(Cl)(Cl)Cl | NC(=O)N1CCc2ccccc21 | null | null | C(Cl)Cl | Acylation | OtherReaction | cfef4e5e5fdae48f59ad6869f2f439a4028225831e19761cbc31175326d5e356 | 1fea30f316824198e233dc7d7d5f0ed1a4a322c4c89c24d4336ce38c6250dbb8 | c1ccc2c(c1)CCN2 | null | 248.2 | [{"value": 248.2, "product": "C(N)(=O)N1CCC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of (-)(2aR,4S)-6-acetyl-4-[di-(cyclopropylmethyl)amino]-1,2,2a, 3,4,5-hexahydrobenz-[cd]indole (2.5 g, 7.7 mmol) and triethylamine (1.1 ml, 8 mmol) in 90 ml CH2Cl2 was added dropwise a solution of 2,2,2-trichloroethylchloroformate (1.7 g, 8 mmol) in 10 ml CH2Cl2. The reaction mixture was stirred at room t... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Trichloro group.Ketone.Ether.Secondary amine.Tertiary amine | Urea | c1cc2c3c(c1)NC[C@@H]3CCC2.C1CC1.C1CC1 | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | HCl | C(Cl)Cl | null | 1 | CC(=O)c1ccc2c3c1C[C@@H](N(CC1CC1)CC1CC1)C[C@H]3CN2.O=C(Cl)OCC(Cl)(Cl)Cl>C(Cl)Cl>NC(=O)N1CCc2ccccc21 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-967d5eaacb4f4440a0cdf06e4362297a | CCCN(CCC)[C@@H]1Cc2c(Br)ccc3c2[C@@H](C1)CN3C(=O)c1ccccc1>>CCCN(CCC)[C@@H]1Cc2c(Br)ccc3c2[C@H](CN3)C1 | Cl.C(CCC)[Li].C(C1=CC=CC=C1)(=O)N1C[C@H]2C=3C(=C(C=CC13)Br)C[C@H](C2)N(CCC)CCC>>BrC1=C2C=3[C@H](CNC3C=C1)C[C@@H](C2)N(CCC)CCC | O=C(c1ccccc1)[N:19]1[c:15]2[cH:14][cH:13][c:11]([Br:12])[c:10]3[c:16]2[C@H:17]([CH2:18]1)[CH2:20][C@H:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])[CH2:9]3>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[C@@H:8]1[CH2:9][c:10]2[c:11]([Br:12])[cH:13][cH:14][c:15]3[c:16]2[C@H:17]([CH2:18][NH:19]3)[CH2:20]1 | CCCN(CCC)[C@@H]1Cc2c(Br)ccc3c2[C@@H](C1)CN3C(=O)c1ccccc1 | CCCN(CCC)[C@@H]1Cc2c(Br)ccc3c2[C@H](CN3)C1 | null | null | O1CCCC1.CCCCCC | Reduction | Hydrogenolysis of tertiary amines | f45e448ff068294d2c8d3a9f528f91025783a450ab56031bb2e90a884f88ae9e | 62cf08a8ae6315067a063b5b3495125ccbdaff6b2340ce1d3e1c7b6cde962ae4 | c1cc2c3c(c1)NC[C@@H]3CCC2 | O=C(-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[c:4]:[c:5]-1:[c:6])-c1:c:c:c:c:c:1>>[c:6]:[c:5]1:[c:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1 | 98.1 | [{"value": 98.1, "product": "BrC1=C2C=3[C@H](CNC3C=C1)C[C@@H](C2)N(CCC)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 30 | MINUTE | To a stirred solution of 12.8 g (29 mmol) of (+)(2aR,4S)-1-benzoyl-6-bromo-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole in 200 ml of tetrahydrofuran cooled to -78° C. under a nitrogen atmosphere was added 20 ml (32 mmol) of a 1.6M solution of n-butyllithium in hexane. The reaction mixture was stirred at -7... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Secondary amine | c1ccccc1.c1cc2c3c(c1)[NH]C[C@@H]3CCC2 | c1cc2c3c(c1)NC[C@@H]3CCC2 | c1cc2c3c(c1)NC[C@@H]3CCC2 | HO- | O1CCCC1.CCCCCC | -78 | 0.5 | CCCN(CCC)[C@@H]1Cc2c(Br)ccc3c2[C@@H](C1)CN3C(=O)c1ccccc1>O1CCCC1.CCCCCC>CCCN(CCC)[C@@H]1Cc2c(Br)ccc3c2[C@H](CN3)C1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ceac2350ec8e4ed58bf37324a62946d8 | CCCN(CCC)[C@@H]1Cc2c(Br)ccc3c2[C@@H](C1)CN3C(c1ccccc1)(c1ccccc1)c1ccccc1.CN(C)C=O>>CCCN(CCC)[C@@H]1Cc2c(C=O)ccc3c2[C@@H](C1)CN3C(c1ccccc1)(c1ccccc1)c1ccccc1 | CN(C=O)C.C(CCC)[Li].BrC1=C2C=3[C@H](CN(C3C=C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C[C@@H](C2)N(CCC)CCC>>C(=O)C1=C2C=3[C@H](CN(C3C=C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C[C@@H](C2)N(CCC)CCC | Br[c:11]1[c:10]2[c:17]3[c:16]([cH:15][cH:14]1)[N:21]([C:22]([c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1)([c:29]1[cH:30][cH:31][cH:32][cH:33][cH:34]1)[c:35]1[cH:36][cH:37][cH:38][cH:39][cH:40]1)[CH2:20][C@@H:18]3[CH2:19][C@H:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])[CH2:9]2.CN(C)[CH:12]=[O:13]>>[CH3:1][CH2:2... | CCCN(CCC)[C@@H]1Cc2c(Br)ccc3c2[C@@H](C1)CN3C(c1ccccc1)(c1ccccc1)c1ccccc1.CN(C)C=O | CCCN(CCC)[C@@H]1Cc2c(C=O)ccc3c2[C@@H](C1)CN3C(c1ccccc1)(c1ccccc1)c1ccccc1 | null | null | O1CCCC1.CCCCCC | C-C Coupling | Bouveault aldehyde synthesis | a9aba44afaf7ca85d37196ef805393b43ce7e6c47fe83d78da3f1131444f7a27 | afd09ced98f25d311f21cc04ba6a50fe7e5516de47e17484683ded13d323b1b2 | c1ccc(C(c2ccccc2)(c2ccccc2)N2C[C@@H]3CCCc4cccc2c43)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5])-[C:6].C-N(-C)-[CH;D2;+0:7]=[O;D1;H0:8]>>[C:6]-[c:4](:[c:5]):[c;H0;D3;+0:1](-[CH;D2;+0:7]=[O;D1;H0:8]):[c:2]:[c:3] | null | [] | -78 | CELSIUS | 1 | HOUR | To a solution of (-)(2aR,4S)-6-bromo-1-trityl-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole (6.8 g, 12 mmol) in 100 ml of tetrahydrofuran cooled to -78° C. under a nitrogen atmosphere was added dropwise a 1.6M solution of n-butyllithium in hexane. The reaction mixture was stirred at -78° C. for 1 hour. Dime... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amide | Aldehyde | c1cc2c3c(c1)[NH]C[C@@H]3CCC2 | c1cc2c3c(c1)[NH]C[C@@H]3CCC2 | c1cc2c3c(c1)[NH]C[C@@H]3CCC2.c1ccccc1.c1ccccc1.c1ccccc1 | HBr | O1CCCC1.CCCCCC | -78 | 1 | CCCN(CCC)[C@@H]1Cc2c(Br)ccc3c2[C@@H](C1)CN3C(c1ccccc1)(c1ccccc1)c1ccccc1.CN(C)C=O>O1CCCC1.CCCCCC>CCCN(CCC)[C@@H]1Cc2c(C=O)ccc3c2[C@@H](C1)CN3C(c1ccccc1)(c1ccccc1)c1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d7e915c839664651bb5e7f91dffd18da | CCCN(CCC)[C@@H]1Cc2c(C=O)ccc3c2[C@@H](C1)CN3C(c1ccccc1)(c1ccccc1)c1ccccc1.[C-]#[N+]CS(=O)(=O)c1ccc(C)cc1>>CCCN(CCC)[C@@H]1Cc2c(-c3cnco3)ccc3c2[C@H](CN3)C1 | C(=O)C1=C2C=3[C@H](CN(C3C=C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C[C@@H](C2)N(CCC)CCC.S(=O)(=O)(C1=CC=C(C)C=C1)C[N+]#[C-].C([O-])([O-])=O.[K+].[K+]>>O1C=NC=C1C1=C2C=3[C@H](CNC3C=C1)C[C@@H](C2)N(CCC)CCC | c1ccc(C(c2ccccc2)(c2ccccc2)[N:23]2[c:19]3[cH:18][cH:17][c:11]([CH:12]=[O:16])[c:10]4[c:20]3[C@H:21]([CH2:22]2)[CH2:24][C@H:8]([N:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])[CH2:9]4)cc1.Cc1ccc(S(=O)(=O)[CH2:13][N+:14]#[C-:15])cc1>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[C@@H:8]1[CH2:9][c:10]2[c:11](-[c:12]... | CCCN(CCC)[C@@H]1Cc2c(C=O)ccc3c2[C@@H](C1)CN3C(c1ccccc1)(c1ccccc1)c1ccccc1.[C-]#[N+]CS(=O)(=O)c1ccc(C)cc1 | CCCN(CCC)[C@@H]1Cc2c(-c3cnco3)ccc3c2[C@H](CN3)C1 | null | null | CO | Functional Group Interconversion | OtherReaction | a52408565944c7a3d1c1a7743313d56487f881a8ffbe35500dfc713845dcf304 | 81799e45ca88af47fd09bd6e38a4dacf267ea894a887436deadef53d6689f76a | c1ncc(-c2ccc3c4c2CCC[C@H]4CN3)o1 | C-c1:c:c:c(-S(=O)(=O)-[CH2;D2;+0:1]-[N+;H0;D2:2]#[C-;H0;D1:3]):c:c:1.[C:4]-[c:5]1:[c:6]2:[c:7](:[c:8]:[c:9]:[c;H0;D3;+0:10]:1-[CH;D2;+0:11]=[O;H0;D1;+0:12])-[N;H0;D3;+0:13](-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1)-[C:14]-[C:15]-2>>[C:4]-[c:5]1:[c:6]2:[c:7](:[c:8]:[c:9]:[c;H0;D3;+0:10]:1-[c;H0;D3;+0:11]1:[cH... | 153.6 | [{"value": 153.6, "product": "O1C=NC=C1C1=C2C=3[C@H](CNC3C=C1)C[C@@H](C2)N(CCC)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A reaction mixture of (-)(2aR,4S)-6-formyl-1-trityl-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole (1.06 g, 2 mmol), tosylmethyl isocyanide (390 mg, 2 mmol) and potassium carbonate (304 mg, 2.2 imnol) in 100 ml of methanol was stirred at reflux temperature under a nitrogen atomosphere for 16 hours. The react... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Aldehyde.Isocyanide.Tertiary amine | Secondary amine | c1ccccc1.c1ccccc1.c1ccccc1.c1cc2c3c(c1)[NH]C[C@@H]3CCC2.c1ccccc1 | c1cocn1.c1cc2c3c(c1)NC[C@@H]3CCC2 | c1cocn1.c1cc2c3c(c1)NC[C@@H]3CCC2 | TsOH.HO- | CO | null | null | CCCN(CCC)[C@@H]1Cc2c(C=O)ccc3c2[C@@H](C1)CN3C(c1ccccc1)(c1ccccc1)c1ccccc1.[C-]#[N+]CS(=O)(=O)c1ccc(C)cc1>CO>CCCN(CCC)[C@@H]1Cc2c(-c3cnco3)ccc3c2[C@H](CN3)C1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ed13c97cbeb948bda6aee994a95925f6 | Brc1cccnc1>>OB(O)c1cccnc1 | BrC=1C=NC=CC1.COB(OC)OC.C(C)(C)(C)[Li]>>N1=CC(=CC=C1)B(O)O | Br[c:4]1[cH:5][cH:6][cH:7][n:8][cH:9]1>>[OH:1][B:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][n:8][cH:9]1 | Brc1cccnc1 | OB(O)c1cccnc1 | null | null | CCCCC.C(C)OCC | Functional Group Interconversion | Preparation of boronic acids without boronic ether | 3924fd76fbdecc276cb0ec82b47a9205afc0daae8b87f757779433597cbd5b83 | 3c67ef5cce82b121a680ae296eb1f6d78abe8f9494b62ca3b872477b7553bcfd | c1ccncc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1>>[O;D1;H1:7]-[#5:8](-[O;D1;H1:9])-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1 | null | [] | null | null | null | null | A solution of 4.0 ml (6.56 g, 42 mmol) of 3-bromopyridine and 9 ml (8 mmol) of trimethylborate in 100 ml of diethyl ether was cooled to -70° C. then treated slowly with 33 ml (83.8 mmol) of a 2.54M tert-butyllithium in pentane solution. After allowing the resulting slurry to warm to room temperature the solvents were e... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Boronic acid | c1ccncc1 | c1ccncc1 | c1ccncc1 | Br- | CCCCC.C(C)OCC | null | null | Brc1cccnc1>CCCCC.C(C)OCC>OB(O)c1cccnc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-122a417cbb4b4aedbca3470d47e02bd4 | CCCCC[C@@H]1CC[C@@H](C(=O)O)CC1.C[C@@H](O)[C@@H](N)C(=O)O>>CCCCC[C@@H]1CC[C@@H](C(=O)N[C@@H](C(=O)O)[C@@H](C)O)CC1 | C(CCCC)[C@@H]1CC[C@H](CC1)C(=O)O.C(C(=O)Cl)(=O)Cl.N[C@H]([C@H](O)C)C(=O)O.[OH-].[Na+]>>C(CCCC)[C@@H]1CC[C@H](CC1)C(=O)N[C@H]([C@H](O)C)C(=O)O | O[C:10]([C@H:9]1[CH2:8][CH2:7][C@H:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[CH2:21][CH2:20]1)=[O:11].[NH2:12][C@@H:13]([C:14](=[O:15])[OH:16])[C@@H:17]([CH3:18])[OH:19]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]1[CH2:7][CH2:8][C@H:9]([C:10](=[O:11])[NH:12][C@@H:13]([C:14](=[O:15])[OH:16])[C@@H:17]([CH3:18])[OH:19])[CH2... | CCCCC[C@@H]1CC[C@@H](C(=O)O)CC1.C[C@@H](O)[C@@H](N)C(=O)O | CCCCC[C@@H]1CC[C@@H](C(=O)N[C@@H](C(=O)O)[C@@H](C)O)CC1 | null | null | C(C)#N.C1(=CC=CC=C1)C.C1CCOC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | 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])-[O;D1;H1:11]>>[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])-[O;D1;H1:11] | null | [] | null | null | 1 | HOUR | A solution of trans-4-pentylcyclohexane carboxylic acid (198 mg, 1.0 mmol) in dry toluene (1 mL) is treated with oxalyl chloride (760 mg, 5.9 mmol) at 0° C. and the mixture is stirred for 2 h at the same temperature and 1 h at room temperature. Excess reagent is removed in vacuo. A solution of the crude acid chloride i... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CCCCC1 | HO- | C(C)#N.C1(=CC=CC=C1)C.C1CCOC1 | null | 1 | CCCCC[C@@H]1CC[C@@H](C(=O)O)CC1.C[C@@H](O)[C@@H](N)C(=O)O>C(C)#N.C1(=CC=CC=C1)C.C1CCOC1>CCCCC[C@@H]1CC[C@@H](C(=O)N[C@@H](C(=O)O)[C@@H](C)O)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f4490b4e928e4b9d9dcb6defa9a6ab99 | CCCCOc1ccc(CC(=O)O)cc1.C[C@@H](O)[C@@H](N)C(=O)O>>CCCCOc1ccc(CC(=O)N[C@@H](C(=O)O)[C@@H](C)O)cc1 | C(CCC)OC1=CC=C(C=C1)CC(=O)O.N[C@H]([C@H](O)C)C(=O)O>>C(CCC)OC1=CC=C(C=C1)CC(=O)N[C@H]([C@H](O)C)C(=O)O | O[C:11]([CH2:10][c:9]1[cH:8][cH:7][c:6]([O:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:22][cH:21]1)=[O:12].[NH2:13][C@@H:14]([C:15](=[O:16])[OH:17])[C@@H:18]([CH3:19])[OH:20]>>[CH3:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([CH2:10][C:11](=[O:12])[NH:13][C@@H:14]([C:15](=[O:16])[OH:17])[C@@H:18]([CH3:19])[OH:20])[cH:21... | CCCCOc1ccc(CC(=O)O)cc1.C[C@@H](O)[C@@H](N)C(=O)O | CCCCOc1ccc(CC(=O)N[C@@H](C(=O)O)[C@@H](C)O)cc1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[C:5]-[C:6](-[NH2;D1;+0:7])-[C:8](=[O;D1;H0:9])-[O;D1;H1:10]>>[C:5]-[C:6](-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4])-[C:8](=[O;D1;H0:9])-[O;D1;H1:10] | null | [] | null | null | null | null | 4-Butoxyphenylacetic acid (288 mg, 1.38 mmol) is converted to the acid chloride and added to D-allo-Thr (150 mg, 1.26 mmol) to get 2c-9, following the procedure described in Example 6. The crude product is purified by chromatography (2.5×18 cm column, gradient 4% CH3OH and 0.3% HOAc in CH2Cl2): NMR δ 0.96 (t, J=7.4, 3 ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | null | null | null | CCCCOc1ccc(CC(=O)O)cc1.C[C@@H](O)[C@@H](N)C(=O)O>>CCCCOc1ccc(CC(=O)N[C@@H](C(=O)O)[C@@H](C)O)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-fab0c7f6479240acbdfc8fbbda591dda | COC(=O)C(CCC[C@@H](NC(=O)OC(C)(C)C)C(=O)N[C@H](C)C(=O)OCc1ccc([N+](=O)[O-])cc1)NC(=O)OCc1ccccc1.OCc1ccccc1>>C[C@@H](NC(=O)[C@@H](CCCC(NC(=O)OCc1ccccc1)C(=O)OCc1ccccc1)NC(=O)OC(C)(C)C)C(=O)OCc1ccccc1 | [N+](=O)([O-])C1=CC=C(C=C1)COC([C@H](NC([C@H](NC(=O)OC(C)(C)C)CCCC(NC(=O)OCC1=CC=CC=C1)C(=O)OC)=O)C)=O.C(C1=CC=CC=C1)O>>C1(=CC=CC=C1)COC([C@H](NC([C@H](NC(=O)OC(C)(C)C)CCCC(NC(=O)OCC1=CC=CC=C1)C(=O)OCC1=CC=CC=C1)=O)C)=O | CO[C:22]([CH:10]([CH2:9][CH2:8][CH2:7][C@H:6]([C:4]([NH:3][C@H:2]([CH3:1])[C:40](=[O:41])[O:42][CH2:43][c:44]1[cH:45][cH:46][c:47]([N+](=O)[O-])[cH:48][cH:49]1)=[O:5])[NH:32][C:33](=[O:34])[O:35][C:36]([CH3:37])([CH3:38])[CH3:39])[NH:11][C:12](=[O:13])[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)=[O:23].[O... | COC(=O)C(CCC[C@@H](NC(=O)OC(C)(C)C)C(=O)N[C@H](C)C(=O)OCc1ccc([N+](=O)[O-])cc1)NC(=O)OCc1ccccc1.OCc1ccccc1 | C[C@@H](NC(=O)[C@@H](CCCC(NC(=O)OCc1ccccc1)C(=O)OCc1ccccc1)NC(=O)OC(C)(C)C)C(=O)OCc1ccccc1 | null | CC([O-])C.[Ti+4].CC([O-])C.CC([O-])C.CC([O-])C | C1CCOC1 | Acylation | OtherReaction | 67a2521538f1cf3882205adfab927bff9f52a980468c3c6e198dddc2fc57a40d | 8028bfd6e276cc9541453e1ce714c6ecfffcc714d2893f27985288769ccd7d51 | O=C(CCCCC(NC(=O)OCc1ccccc1)C(=O)OCc1ccccc1)NCC(=O)OCc1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7].O=[N+](-[O-])-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12].[OH;D1;+0:13]-[C:14]-[c:15]>>[C:4]-[C:3](-[#7:5]-[C:6]=[O;D1;H0:7])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:13]-[C:14]-[c:15].[c:10]:[c:9]:[cH;D2;+0:8]:[c:11]:[c:12] | 88.4 | [{"value": 88.0, "product": "C1(=CC=CC=C1)COC([C@H](NC([C@H](NC(=O)OC(C)(C)C)CCCC(NC(=O)OCC1=CC=CC=C1)C(=O)OCC1=CC=CC=C1)=O)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.4, "product": "C1(=CC=CC=C1)COC([C@H](NC([C@H](NC(=O)OC(C)(C)C)CCCC(NC(=O)OCC1=CC=CC=C1)C(=O)OCC1=CC=CC=C1)=O)C)=O", "details":... | null | null | 30 | MINUTE | A mixture of N-[N2 -[(1,1-dimethylethoxy)carbonyl]-N6-[(phenylmethoxy)-carbonyl]-(R)-6-[(methoxy)carbonyl]-L-lysyl]-D-alanine 4-nitrophenylmethyl ester (40a, Kolodziejczyk, et. al., Int. J. Pept. Prot. Res., 1992, 39, 382; 683 mg, 1.06 mmol), 4-- molecular sieves (2.15 g, crushed), THF (10.5 mL), and benzyl alcohol (11... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Nitro group.Primary alcohol | Ester | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | CC([O-])C.[Ti+4].CC([O-])C.CC([O-])C.CC([O-])C.C1CCOC1 | null | 0.5 | COC(=O)C(CCC[C@@H](NC(=O)OC(C)(C)C)C(=O)N[C@H](C)C(=O)OCc1ccc([N+](=O)[O-])cc1)NC(=O)OCc1ccccc1.OCc1ccccc1>CC([O-])C.[Ti+4].CC([O-])C.CC([O-])C.CC([O-])C.C1CCOC1>C[C@@H](NC(=O)[C@@H](CCCC(NC(=O)OCc1ccccc1)C(=O)OCc1ccccc1)NC(=O)OC(C)(C)C)C(=O)OCc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a7bbe3157e2343b29b5ae2259a7f0280 | C[C@@H](NC(=O)[C@@H](CCCC(NC(=O)OCc1ccccc1)C(=O)OCc1ccccc1)NC(=O)OC(C)(C)C)C(=O)OCc1ccccc1>>C[C@@H](NC(=O)[C@H](N)CCCC(NC(=O)OCc1ccccc1)C(=O)OCc1ccccc1)C(=O)OCc1ccccc1 | C1(=CC=CC=C1)COC([C@H](NC([C@H](NC(=O)OC(C)(C)C)CCCC(NC(=O)OCC1=CC=CC=C1)C(=O)OCC1=CC=CC=C1)=O)C)=O>>C1(=CC=CC=C1)COC([C@H](NC([C@H](N)CCCC(NC(=O)OCC1=CC=CC=C1)C(=O)OCC1=CC=CC=C1)=O)C)=O | CC(C)(C)OC(=O)[NH:7][C@@H:6]([C:4]([NH:3][C@H:2]([CH3:1])[C:33](=[O:34])[O:35][CH2:36][c:37]1[cH:38][cH:39][cH:40][cH:41][cH:42]1)=[O:5])[CH2:8][CH2:9][CH2:10][CH:11]([NH:12][C:13](=[O:14])[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[C:23](=[O:24])[O:25][CH2:26][c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1>... | C[C@@H](NC(=O)[C@@H](CCCC(NC(=O)OCc1ccccc1)C(=O)OCc1ccccc1)NC(=O)OC(C)(C)C)C(=O)OCc1ccccc1 | C[C@@H](NC(=O)[C@H](N)CCCC(NC(=O)OCc1ccccc1)C(=O)OCc1ccccc1)C(=O)OCc1ccccc1 | null | null | C(=O)(C(F)(F)F)O | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C(CCCCC(NC(=O)OCc1ccccc1)C(=O)OCc1ccccc1)NCC(=O)OCc1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#7:6]-[C:7]-[C:8](-[#8:9])=[O;D1;H0:10]>>[#8:9]-[C:8](=[O;D1;H0:10])-[C:7]-[#7:6]-[C:4](=[O;D1;H0:5])-[C:2](-[C:3])-[NH2;D1;+0:1] | 105.6 | [{"value": 105.6, "product": "C1(=CC=CC=C1)COC([C@H](NC([C@H](N)CCCC(NC(=O)OCC1=CC=CC=C1)C(=O)OCC1=CC=CC=C1)=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 40b (251 mg, 0.37 mmol) in TFA (870 μl) is stirred for 30 min at 0° C. The TFA is removed and the oil is taken up in EtOAc and washed with saturated NaHCO3 solution. Drying and removal of the solvent gives 3b (225 mg, slight excess) which is used in subsequent reactions without further handling: NMR δ 1.3... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C(=O)(C(F)(F)F)O | null | null | C[C@@H](NC(=O)[C@@H](CCCC(NC(=O)OCc1ccccc1)C(=O)OCc1ccccc1)NC(=O)OC(C)(C)C)C(=O)OCc1ccccc1>C(=O)(C(F)(F)F)O>C[C@@H](NC(=O)[C@H](N)CCCC(NC(=O)OCc1ccccc1)C(=O)OCc1ccccc1)C(=O)OCc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d896f7bdfcab4970950d4d3e8a62ba2c | CCCCCCC(=O)N[C@@H](C(=O)OCc1ccccc1)[C@@H](C)O.C[C@@H](NC(=O)[C@H](N)CCCC(NC(=O)OCc1ccccc1)C(=O)OCc1ccccc1)C(=O)OCc1ccccc1.O=C(Cl)Cl>>CCCCCCC(=O)NC(C(=O)OCc1ccccc1)C(C)OC(=O)N[C@H](CCCC(NC(=O)OCc1ccccc1)C(=O)OCc1ccccc1)C(=O)N[C@H](C)C(=O)OCc1ccccc1 | C1(=CC=CC=C1)COC([C@H](NC(CCCCCC)=O)[C@H](O)C)=O.C(=O)(Cl)Cl.C1(=CC=CC=C1)COC([C@H](NC([C@H](N)CCCC(NC(=O)OCC1=CC=CC=C1)C(=O)OCC1=CC=CC=C1)=O)C)=O>>C1(=CC=CC=C1)COC([C@H](NC([C@H](NC(=O)OC(C(C(OCC1=CC=CC=C1)=O)NC(CCCCCC)=O)C)CCCC(NC(=O)OCC1=CC=CC=C1)C(=O)OCC1=CC=CC=C1)=O)C)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7](=[O:8])[NH:9][C@@H:10]([C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[C@@H:21]([CH3:22])[OH:23].[NH2:26][C@H:27]([CH2:28][CH2:29][CH2:30][CH:31]([NH:32][C:33](=[O:34])[O:35][CH2:36][c:37]1[cH:38][cH:39][cH:40][cH:41][cH:42]1)[C:43](=[O:44])[O:45... | CCCCCCC(=O)N[C@@H](C(=O)OCc1ccccc1)[C@@H](C)O.C[C@@H](NC(=O)[C@H](N)CCCC(NC(=O)OCc1ccccc1)C(=O)OCc1ccccc1)C(=O)OCc1ccccc1.O=C(Cl)Cl | CCCCCCC(=O)NC(C(=O)OCc1ccccc1)C(C)OC(=O)N[C@H](CCCC(NC(=O)OCc1ccccc1)C(=O)OCc1ccccc1)C(=O)N[C@H](C)C(=O)OCc1ccccc1 | null | null | CCOC(=O)C.O.CC#N.C1CCOC1 | Protection | OtherReaction | 3d68f0bb52b2df855222c8931b2a71f964865ce2ec96df1e3152c2a869e9cad1 | c63e4fd0e0f3664367af6bef32d20900630deacde56a2d0fc4d3ba46b7f4728b | O=C(CCOC(=O)N[C@H](CCCC(NC(=O)OCc1ccccc1)C(=O)OCc1ccccc1)C(=O)NCC(=O)OCc1ccccc1)OCc1ccccc1 | Cl-[C;H0;D3;+0:1](-Cl)=[O;D1;H0:2].[#8:3]-[C:4](=[O;D1;H0:5])-[C:6]-[#7:7]-[C:8](=[O;D1;H0:9])-[C:10](-[C:11])-[NH2;D1;+0:12].[C:13]-[#8:14]-[C:15](=[O;D1;H0:16])-[C:17](-[#7:18]-[C:19]=[O;D1;H0:20])-[C@@H;D3;+0:21](-[C;D1;H3:22])-[OH;D1;+0:23]>>[#8:3]-[C:4](=[O;D1;H0:5])-[C:6]-[#7:7]-[C:8](=[O;D1;H0:9])-[C:10](-[C:11]... | null | [] | null | null | 5 | HOUR | A solution of 2e-1 (173.6 mg, 0.54 mmol) in THF (Sure/Seal solvent redried over 3--MS, 1.45 mL) is added to excess cold phosgene (1.92M solution in toluene; 1.40 mL, 2.63 mmol), alternately with TEA (81 μl, 0.58 mmol) over a period of 15 min at 0° C. The resulting milky mixture is stirred for an addition 15 min at the ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Secondary alcohol.Primary amine | Carbamic ester | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HCl | CCOC(=O)C.O.CC#N.C1CCOC1 | null | 5 | CCCCCCC(=O)N[C@@H](C(=O)OCc1ccccc1)[C@@H](C)O.C[C@@H](NC(=O)[C@H](N)CCCC(NC(=O)OCc1ccccc1)C(=O)OCc1ccccc1)C(=O)OCc1ccccc1.O=C(Cl)Cl>CCOC(=O)C.O.CC#N.C1CCOC1>CCCCCCC(=O)NC(C(=O)OCc1ccccc1)C(C)OC(=O)N[C@H](CCCC(NC(=O)OCc1ccccc1)C(=O)OCc1ccccc1)C(=O)N[C@H](C)C(=O)OCc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-47bad7a88d7c419c9e60e8abe49c3d77 | CCCCCCC(=O)NC(C(=O)OCc1ccccc1)C(C)OC(=O)N[C@H](CCCC(NC(=O)OCc1ccccc1)C(=O)OCc1ccccc1)C(=O)N[C@H](C)C(=O)OCc1ccccc1>>CCCCCCC(=O)NC(C(=O)O)C(C)OC(=O)N[C@H](CCCC(N)C(=O)O)C(=O)N[C@H](C)C(=O)O | C1(=CC=CC=C1)COC([C@H](NC([C@H](NC(=O)OC(C(C(OCC1=CC=CC=C1)=O)NC(CCCCCC)=O)C)CCCC(NC(=O)OCC1=CC=CC=C1)C(=O)OCC1=CC=CC=C1)=O)C)=O>>C(=O)(O)C(CCC[C@@H](NC(=O)OC(C(NC(CCCCCC)=O)C(=O)O)C)C(=O)N[C@H](C)C(=O)O)N | O=C(OCc1ccccc1)[NH:25][CH:24]([CH2:23][CH2:22][CH2:21][C@@H:20]([NH:19][C:17]([O:16][CH:14]([CH:10]([NH:9][C:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:8])[C:11](=[O:12])[O:13]Cc1ccccc1)[CH3:15])=[O:18])[C:29](=[O:30])[NH:31][C@H:32]([CH3:33])[C:34](=[O:35])[O:36]Cc1ccccc1)[C:26](=[O:27])[O:28]Cc1ccccc1>>[CH3:1]... | CCCCCCC(=O)NC(C(=O)OCc1ccccc1)C(C)OC(=O)N[C@H](CCCC(NC(=O)OCc1ccccc1)C(=O)OCc1ccccc1)C(=O)N[C@H](C)C(=O)OCc1ccccc1 | CCCCCCC(=O)NC(C(=O)O)C(C)OC(=O)N[C@H](CCCC(N)C(=O)O)C(=O)N[C@H](C)C(=O)O | null | [OH-].[OH-].[Pd+2] | CCOC(=O)C.CCO | Reduction | OtherReaction | 93f12f53ec8755e6497c80a0567af4871fd2a985c1b630f3d409d24de7706e58 | f7527cac2ca4830281723fda6ba4921ecc42f4fadea8f894a8ccad6b4c927d07 | null | O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-C-c1:c:c:c:c:c:1.[C:7]-[C:8](=[O;D1;H0:9])-[O;H0;D2;+0:10]-C-c1:c:c:c:c:c:1.[C:11]-[C:12](=[O;D1;H0:13])-[O;H0;D2;+0:14]-C-c1:c:c:c:c:c:1>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6].[C:7]-[C:8](=[O;D1;H0:9])-[OH;D1;... | null | [] | null | null | 5.5 | HOUR | A solution of 1a-1 (140 mg, 0.15 mmol) in EtOAc/EtOH (5 mL:15 mL) is hydrogenated over Pd(OH)2 (Pearlman's catalyst, 20% on C, 100 mg) using a Parr apparatus at an initial pressure of 70 psi. After 5.5 h, filtration and evaporation gives a colorless glass. The latter is triturated with ether and the sides of the flask ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ester.Ester.Ether | Carboxylic acid.Carboxylic acid.Carboxylic acid.Primary amine | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | null | HO- | [OH-].[OH-].[Pd+2].CCOC(=O)C.CCO | null | 5.5 | CCCCCCC(=O)NC(C(=O)OCc1ccccc1)C(C)OC(=O)N[C@H](CCCC(NC(=O)OCc1ccccc1)C(=O)OCc1ccccc1)C(=O)N[C@H](C)C(=O)OCc1ccccc1>[OH-].[OH-].[Pd+2].CCOC(=O)C.CCO>CCCCCCC(=O)NC(C(=O)O)C(C)OC(=O)N[C@H](CCCC(N)C(=O)O)C(=O)N[C@H](C)C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-fc79242360f14622a6a0957e5c6bd892 | CCCCCC.CCCCCCC(=O)N[C@@H](CO)C(=O)OC.CCOC(C)=O>>CCCCCCC(=O)N1[C@H](C(=O)OC)COC1(C)C | COC([C@@H](NC(CCCCCC)=O)CO)=O.CC=1C=CC(=CC1)S(=O)(=O)O.CCCCCC.CCOC(=O)C.C(=O)([O-])[O-].[K+].[K+]>>COC(=O)[C@H]1N(C(OC1)(C)C)C(CCCCCC)=O | CCCCC[CH3:19].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7](=[O:8])[NH:9][C@H:10]([C:11](=[O:12])[O:13][CH3:14])[CH2:15][OH:16].CCO[C:17](=O)[CH3:18]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7](=[O:8])[N:9]1[C@H:10]([C:11](=[O:12])[O:13][CH3:14])[CH2:15][O:16][C:17]1([CH3:18])[CH3:19] | CCCCCC.CCCCCCC(=O)N[C@@H](CO)C(=O)OC.CCOC(C)=O | CCCCCCC(=O)N1[C@H](C(=O)OC)COC1(C)C | null | null | CC(=O)C.COC(C)(C)OC | Heteroatom Alkylation and Arylation | OtherReaction | 710a85dd6a91fbf39b6013ce9cdafa1daab72f8b8adcb5ec399f373d14fe75f9 | 567a9783e07a178d793aef6ce57238f12658c3c2aa08cc932125383868d3d685 | C1COCN1 | C-C-C-C-C-[CH3;D1;+0:1].C-C-O-[C;H0;D3;+0:2](=O)-[C;D1;H3:3].[C:4]-[C:5](=[O;D1;H0:6])-[NH;D2;+0:7]-[C:8](-[C:9]-[OH;D1;+0:10])-[C:11](=[O;D1;H0:12])-[#8:13]-[C;D1;H3:14]>>[C:4]-[C:5](=[O;D1;H0:6])-[N;H0;D3;+0:7]1-[C:8](-[C:11](=[O;D1;H0:12])-[#8:13]-[C;D1;H3:14])-[C:9]-[O;H0;D2;+0:10]-[C;H0;D4;+0:2]-1(-[C;D1;H3:3])-[C... | null | [] | null | null | null | null | Compound 2j (320 mg, 1.38 mmol) and p-TSA (40 mg) are dissolved in dry acetone (2 ml) and 2,2-dimethoxypropane (2 ml). The resulting solution is heated overnight at reflux. Solid K2CO3 is added and the volatiles removed in vacuo to give a residue. Flash chromatography (2×21 cm column, 6:1 hexane/EtOAc) of the residue p... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amide.Primary alcohol | Ether.Tertiary amide | null | C1COC[NH]1 | C1COC[NH]1 | HO- | CC(=O)C.COC(C)(C)OC | null | null | CCCCCC.CCCCCCC(=O)N[C@@H](CO)C(=O)OC.CCOC(C)=O>CC(=O)C.COC(C)(C)OC>CCCCCCC(=O)N1[C@H](C(=O)OC)COC1(C)C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6be7cdeeabcd409597ffca3d172897d1 | CCCCCCC(=O)N1[C@H](C(=O)OC)COC1(C)C>>CCCCCCC(=O)N1[C@H](CO)COC1(C)C | COC(=O)[C@H]1N(C(OC1)(C)C)C(CCCCCC)=O.[BH4-].[Li+]>>CC1(OC[C@H](N1C(CCCCCC)=O)CO)C | CO[C:11]([C@H:10]1[N:9]([C:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:8])[C:15]([CH3:16])([CH3:17])[O:14][CH2:13]1)=[O:12]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7](=[O:8])[N:9]1[C@H:10]([CH2:11][OH:12])[CH2:13][O:14][C:15]1([CH3:16])[CH3:17] | CCCCCCC(=O)N1[C@H](C(=O)OC)COC1(C)C | CCCCCCC(=O)N1[C@H](CO)COC1(C)C | null | null | CCOCC | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | C1COCN1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]1-[C:4]-[#8:5]-[C:6]-[#7:7]-1-[C:8]=[O;D1;H0:9]>>[O;D1;H0:9]=[C:8]-[#7:7]1-[C:6]-[#8:5]-[C:4]-[C:3]-1-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | null | null | 3 | HOUR | A solution of 8a (296 mg, 1.09 mmol) in dry ether (1 mL) is treated with lithium borohydride (2M solution in THF, 0.55 mL, 1.09 meq) under an argon atmosphere. The mixture is stirred for 3 hr at reflux and 18 h at room temperature. The resulting mixture is diluted with ether and quenched with methanol. The volatiles ar... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1COC[NH]1 | Other | CCOCC | null | 3 | CCCCCCC(=O)N1[C@H](C(=O)OC)COC1(C)C>CCOCC>CCCCCCC(=O)N1[C@H](CO)COC1(C)C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-cd0d169049644f7aa72f8fc73856b15d | CCCCCCC(=O)N1[C@H](CO)COC1(C)C>>CCCCCCC(=O)N1[C@H](C=O)COC1(C)C | C(C)N(CC)CC.CC1(OC[C@H](N1C(CCCCCC)=O)CO)C.C(C(=O)Cl)(=O)Cl.CS(=O)C>>CC1(OC[C@H](N1C(CCCCCC)=O)C=O)C | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7](=[O:8])[N:9]1[C@H:10]([CH2:11][OH:12])[CH2:13][O:14][C:15]1([CH3:16])[CH3:17]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7](=[O:8])[N:9]1[C@H:10]([CH:11]=[O:12])[CH2:13][O:14][C:15]1([CH3:16])[CH3:17] | CCCCCCC(=O)N1[C@H](CO)COC1(C)C | CCCCCCC(=O)N1[C@H](C=O)COC1(C)C | null | null | O.C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | C1COCN1 | [O;D1;H0:1]=[C:2]-[#7:3]1-[C:4]-[#8:5]-[C:6]-[C:7]-1-[CH2;D2;+0:8]-[OH;D1;+0:9]>>[O;D1;H0:1]=[C:2]-[#7:3]1-[C:4]-[#8:5]-[C:6]-[C:7]-1-[CH;D2;+0:8]=[O;H0;D1;+0:9] | null | [] | -60 | CELSIUS | 15 | MINUTE | A solution of oxalyl chloride (105 μl, 1.23 mmol) in CH2Cl2 (2.75 mL) is cooled to -60° C. A solution of DMSO (192 μL) in CH2Cl2 (0.55 mL) is added over a period of 5 min. and the resulting milky mixture is stirred for 15 min at -60° C. The alcohol from Example 39 (133 mg., 0.55 mmol) in CH2Cl2 (0.55 ml) is added to th... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | C1COC[NH]1 | null | O.C(Cl)Cl | -60 | 0.25 | CCCCCCC(=O)N1[C@H](CO)COC1(C)C>O.C(Cl)Cl>CCCCCCC(=O)N1[C@H](C=O)COC1(C)C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ba83b90f82aa43f2bdb332b49d366c08 | CCCCCCC(=O)N1[C@H](C=O)COC1(C)C>>CCCCCCC(=O)N1[C@H](C(O)CC)COC1(C)C | CC1(OC[C@H](N1C(CCCCCC)=O)C=O)C.CC[Mg+].[Br-]>>C(C)C(O)[C@H]1N(C(OC1)(C)C)C(CCCCCC)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7](=[O:8])[N:9]1[C@H:10]([CH:11]=[O:12])[CH2:15][O:16][C:17]1([CH3:18])[CH3:19]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7](=[O:8])[N:9]1[C@H:10]([CH:11]([OH:12])[CH2:13][CH3:14])[CH2:15][O:16][C:17]1([CH3:18])[CH3:19] | CCCCCCC(=O)N1[C@H](C=O)COC1(C)C | CCCCCCC(=O)N1[C@H](C(O)CC)COC1(C)C | null | null | CCOCC | Miscellaneous | OtherReaction | 1ffaf80f172e20da969364a5d2977299bc51b204f2262675c45c8ec58ff36ac0 | e005d650d08e61fc67b766830eb53235a9bc084cc3667d2f8a73c2fb8bb34277 | C1COCN1 | [O;D1;H0:1]=[C:2]-[#7:3]1-[C:4]-[#8:5]-[C:6]-[C:7]-1-[CH;D2;+0:8]=[O;H0;D1;+0:9]>>[C;D1;H3:10]-[C:11]-[CH;D3;+0:8](-[OH;D1;+0:9])-[C:7]1-[C:6]-[#8:5]-[C:4]-[#7:3]-1-[C:2]=[O;D1;H0:1] | null | [] | null | null | 1.5 | HOUR | A solution of 9a (108 mg, 0.44 mmol) in ether (1 mL) is added dropwise to a cold (5°) solution of EtMgBr (3M in ether, 0.36 mL). The cold bath is removed, a crystal of iodine is added to the mixture and stirring is continued for 1.5 h at room temperature. The resulting mixture is diluted with EtOAc and washed with satu... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary alcohol | null | null | C1COC[NH]1 | Other | CCOCC | null | 1.5 | CCCCCCC(=O)N1[C@H](C=O)COC1(C)C>CCOCC>CCCCCCC(=O)N1[C@H](C(O)CC)COC1(C)C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-160aa4a07a0a4c1883d138198c5f37bd | CC(C)(C)[Si](C)(C)Cl.CCCCCCC(=O)NC(CO)C(C)O>>CCCCCCC(=O)NC(CO[Si](C)(C)C(C)(C)C)C(C)O | OC(C(CO)NC(CCCCCC)=O)C.[Si](C)(C)(C(C)(C)C)Cl.C(C)N(CC)CC>>CC(C)(C)[Si](OCC(C(C)O)NC(CCCCCC)=O)(C)C | Cl[Si:13]([CH3:14])([CH3:15])[C:16]([CH3:17])([CH3:18])[CH3:19].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7](=[O:8])[NH:9][CH:10]([CH2:11][OH:12])[CH:20]([CH3:21])[OH:22]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7](=[O:8])[NH:9][CH:10]([CH2:11][O:12][Si:13]([CH3:14])([CH3:15])[C:16]([CH3:17])([CH3:18])[CH3:19])... | CC(C)(C)[Si](C)(C)Cl.CCCCCCC(=O)NC(CO)C(C)O | CCCCCCC(=O)NC(CO[Si](C)(C)C(C)(C)C)C(C)O | null | CN(C1=CC=NC=C1)C | O.C(Cl)Cl | Protection | Alcohol protection with silyl ethers | 0085cd6629412592263fdf1537bdf8c19ef10dbeafe6f880807464d8107fa715 | d2a170d01b2f3ec57d6fac058519475050ba5531f5d304635fb42e153d5bb9b5 | null | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[C:8]-[C:9]-[OH;D1;+0:10]>>[C:8]-[C:9]-[O;H0;D2;+0:10]-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7] | 109.5 | [{"value": 109.5, "product": "CC(C)(C)[Si](OCC(C(C)O)NC(CCCCCC)=O)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A mixture of 11c, (1.945 g) of t-butyldimethylsilyl chloride, (1.4165 g) of triethylamine (951 mg, 1.31 mL), and 4-dimethylaminopyridine (42.76 mg) in 13 mL of methylene chloride is stirred under argon at room temperature for 18 h. The reaction mixture is diluted with methylene chloride and water added. The organic lay... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Silyl protective group | TMS ether protective group | null | null | null | HCl | CN(C1=CC=NC=C1)C.O.C(Cl)Cl | null | 18 | CC(C)(C)[Si](C)(C)Cl.CCCCCCC(=O)NC(CO)C(C)O>CN(C1=CC=NC=C1)C.O.C(Cl)Cl>CCCCCCC(=O)NC(CO[Si](C)(C)C(C)(C)C)C(C)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-2ac639f6a6d7446bbbb8b363582dbac2 | CCCCCCC(=O)NC(CO[Si](C)(C)C(C)(C)C)C(C)O>>CCCCCCC(=O)N[C@@H](CO[Si](C)(C)C(C)(C)C)C(C)=O | CC(C)(C)[Si](OCC(C(C)O)NC(CCCCCC)=O)(C)C.[Cr](=O)(=O)([O-])O[Cr](=O)(=O)[O-].[NH+]1=CC=CC=C1.[NH+]1=CC=CC=C1>>CC(C)(C)[Si](OC[C@@H](C(C)=O)NC(CCCCCC)=O)(C)C | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7](=[O:8])[NH:9][CH:10]([CH2:11][O:12][Si:13]([CH3:14])([CH3:15])[C:16]([CH3:17])([CH3:18])[CH3:19])[CH:20]([CH3:21])[OH:22]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7](=[O:8])[NH:9][C@@H:10]([CH2:11][O:12][Si:13]([CH3:14])([CH3:15])[C:16]([CH3:17])([CH3:18])[CH3:19])[C... | CCCCCCC(=O)NC(CO[Si](C)(C)C(C)(C)C)C(C)O | CCCCCCC(=O)N[C@@H](CO[Si](C)(C)C(C)(C)C)C(C)=O | null | null | O.CN(C=O)C | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | null | [#8:1]-[C:2]-[CH;D3;+0:3](-[#7:4]-[C:5](-[C:6])=[O;D1;H0:7])-[CH;D3;+0:8](-[C;D1;H3:9])-[OH;D1;+0:10]>>[#8:1]-[C:2]-[C@H;D3;+0:3](-[#7:4]-[C:5](-[C:6])=[O;D1;H0:7])-[C;H0;D3;+0:8](-[C;D1;H3:9])=[O;H0;D1;+0:10] | 81.8 | [{"value": 81.8, "product": "CC(C)(C)[Si](OC[C@@H](C(C)=O)NC(CCCCCC)=O)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A mixture of (10c), (2.30 g, 6.94 mmol) and pyridinium dichromate (10.62 g, 28.2 mmol) in 20 mL of N,N-dimethylformamide is stirred under argon for 18 h. The reaction mixture is diluted with 100 mL of water and extracted with ethyl acetate (3×40 mL). The organic layer is separated, washed with water and brine, dried an... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | null | null | O.CN(C=O)C | null | 18 | CCCCCCC(=O)NC(CO[Si](C)(C)C(C)(C)C)C(C)O>O.CN(C=O)C>CCCCCCC(=O)N[C@@H](CO[Si](C)(C)C(C)(C)C)C(C)=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-679238dd29464869b20e3dd2c6f6680b | O=C(O)CC[C@H]1C(=O)OCN1C(=O)OCc1ccccc1>>O=CCC[C@H]1C(=O)OCN1C(=O)OCc1ccccc1 | O=C1[C@@H](N(CO1)C(=O)OCC1=CC=CC=C1)CCC(=O)O.[Cr](=O)(=O)([O-])Cl.[NH+]1=CC=CC=C1>>O=C1[C@@H](N(CO1)C(=O)OCC1=CC=CC=C1)CCC=O | O[C:2](=[O:1])[CH2:3][CH2:4][C@H:5]1[C:6](=[O:7])[O:8][CH2:9][N:10]1[C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[O:1]=[CH:2][CH2:3][CH2:4][C@H:5]1[C:6](=[O:7])[O:8][CH2:9][N:10]1[C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | O=C(O)CC[C@H]1C(=O)OCN1C(=O)OCc1ccccc1 | O=CCC[C@H]1C(=O)OCN1C(=O)OCc1ccccc1 | null | null | C(Cl)Cl.C1CCOC1 | Reduction | OtherReaction | 78999da0d33b2c10ff8c3d41626c41ea14d2697ff6d1d7e5baf78453ec38592a | f41d7c101137b93550fdf296ceb4547d1ce640e4cbceb5b7b006723d153456c9 | O=C1CN(C(=O)OCc2ccccc2)CO1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]>>[C:4]-[C:3]-[CH;D2;+0:1]=[O;D1;H0:2] | 51.4 | [{"value": 51.4, "product": "O=C1[C@@H](N(CO1)C(=O)OCC1=CC=CC=C1)CCC=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | A solution of 27 g (92.7 mmol) of the crude acid (43c) in 200 mL of THF is cooled to 0° C. and 13 mL (10.7 g, 141 mmol) of borane-methyl sulfide complex is added dropwise via an addition funnel. The reaction is allowed to warm gradually to room temperature and stirred for 12 h. The resulting mixture is concentrated in ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Aldehyde | null | null | C1COC[NH]1.c1ccccc1 | Other | C(Cl)Cl.C1CCOC1 | null | 12 | O=C(O)CC[C@H]1C(=O)OCN1C(=O)OCc1ccccc1>C(Cl)Cl.C1CCOC1>O=CCC[C@H]1C(=O)OCN1C(=O)OCc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-26d5c56c33f14a27bcfc5293e42d4237 | COC(=O)C(=CCCC1C(=O)OCN1C(=O)OCc1ccccc1)NC(=O)OC(C)(C)C.COC(=O)[C@@H](C)N>>COC(=O)/C(=C/CC[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@H](C)C(=O)OC)NC(=O)OC(C)(C)C | COC([C@H](N)C)=O.C1(=CC=CC=C1)COC(=O)N1COC(C1CCC=C(C(=O)OC)NC(=O)OC(C)(C)C)=O.COC([C@H](N)C)=O>>COC([C@H](NC([C@@H](NC(=O)OCC1=CC=CC=C1)CC\C=C(/NC(=O)OC(C)(C)C)\C(=O)OC)=O)C)=O | C1O[C:21](=[O:22])[CH:9]([CH2:8][CH2:7][CH:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[NH:30][C:31](=[O:32])[O:33][C:34]([CH3:35])([CH3:36])[CH3:37])[N:10]1[C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1.[NH2:23][C@H:24]([CH3:25])[C:26](=[O:27])[O:28][CH3:29]>>[CH3:1][O:2][C:3](=[O:4])/[C:5](=[CH:6]/[C... | COC(=O)C(=CCCC1C(=O)OCN1C(=O)OCc1ccccc1)NC(=O)OC(C)(C)C.COC(=O)[C@@H](C)N | COC(=O)/C(=C/CC[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@H](C)C(=O)OC)NC(=O)OC(C)(C)C | null | null | null | Protection | Displacement of ethoxy group by primary amine | e66d38b79edbc67df95fcb4abe49f899502b76bda3019f3ed03a0713db3334de | ea4684e285b3bc93becd6db94f29982da7cfdb0828955af8ce9c5dd9c972430f | c1ccccc1 | [C;D1;H3:1]-[C:2](-[NH2;D1;+0:3])-[C:4](=[O;D1;H0:5])-[#8:6]-[C;D1;H3:7].[C:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[N;H0;D3;+0:12]1-C-O-[C;H0;D3;+0:13](=[O;D1;H0:14])-[CH;D3;+0:15]-1-[C:16]-[C:17]-[C:18]=[C:19]>>[C:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[NH;D2;+0:12]-[C@@H;D3;+0:15](-[C:16]-[C:17]/[C:18]=[C:19])-[C;H0;D3;+0:13](=[O;... | 70.2 | [{"value": 70.2, "product": "COC([C@H](NC([C@@H](NC(=O)OCC1=CC=CC=C1)CC\\C=C(/NC(=O)OC(C)(C)C)\\C(=O)OC)=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 10 | MINUTE | A mixture of 3.3 g of D-alanine methyl ester and 7.1 g of 46c is heated at 140° C. for 10 min, then another 1.6 g of D-alanine methyl ester is added. Heating is continued at 140° C. for an additional 10 min. After cooling to ambient temperature the crude product is chromatographed on silica gel using variable gradient ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Primary amine | Carbamic ester.Secondary amide | C1COC[NH]1 | null | c1ccccc1 | HO- | null | 140 | 0.166667 | COC(=O)C(=CCCC1C(=O)OCN1C(=O)OCc1ccccc1)NC(=O)OC(C)(C)C.COC(=O)[C@@H](C)N>>COC(=O)/C(=C/CC[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@H](C)C(=O)OC)NC(=O)OC(C)(C)C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-c10aac4f4a5d462eb61c169d6e23c1c5 | COC(=O)/C(=C/CC[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@H](C)C(=O)OC)NC(=O)OC(C)(C)C>>COC(=O)C(CCC[C@@H](NC(=O)OCc1ccccc1)C(=O)N[C@H](C)C(=O)OC)NC(=O)OC(C)(C)C | COC([C@H](NC([C@@H](NC(=O)OCC1=CC=CC=C1)CC\C=C(/NC(=O)OC(C)(C)C)\C(=O)OC)=O)C)=O.[H][H]>>COC([C@H](NC([C@H](NC(=O)OCC1=CC=CC=C1)CCCC(NC(=O)OC(C)(C)C)C(=O)OC)=O)C)=O | [CH3:1][O:2][C:3](=[O:4])/[C:5](=[CH:6]/[CH2:7][CH2:8][C@H:9]([NH:10][C:11](=[O:12])[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[C:21](=[O:22])[NH:23][C@H:24]([CH3:25])[C:26](=[O:27])[O:28][CH3:29])[NH:30][C:31](=[O:32])[O:33][C:34]([CH3:35])([CH3:36])[CH3:37]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][CH2:... | COC(=O)/C(=C/CC[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@H](C)C(=O)OC)NC(=O)OC(C)(C)C | COC(=O)C(CCC[C@@H](NC(=O)OCc1ccccc1)C(=O)N[C@H](C)C(=O)OC)NC(=O)OC(C)(C)C | null | Cl(=O)(=O)(=O)[O-].[Rh+] | C(C)(=O)O.C1CCOC1 | Reduction | Hydrogenation (double to single) | c5482e96d32f880dae9cdf88ceb576b12289d0a709a9745c321f8f5233d183f3 | b586296faf9080b398947dcba4825d3daf71a75997a309df19187f20bff3e49d | c1ccccc1 | [C:1]-[C:2]/[CH;D2;+0:3]=[C;H0;D3;+0:4](\[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C:13](=[O;D1;H0:14])-[#8:15]-[C;D1;H3:16]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[CH;D3;+0:4](-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C:13](=[O;D1;H0:14])-[#8:1... | 92.6 | [{"value": 92.6, "product": "COC([C@H](NC([C@H](NC(=O)OCC1=CC=CC=C1)CCCC(NC(=O)OC(C)(C)C)C(=O)OC)=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 8.5 g of 47c in 25 mL of acetic acid and 250 mL of THF is hydrogenated at 48 psi of hydrogen over 0.5 g of (bicyclo(2.2.1.)hepta-2,5-diene[2S,3S]bis(diphenylphosphino)butane)rhodium(I) perchlorate for 18 h. The reaction is filtered and evaporated to a residue. The residue is chromatographed using variable... | 10.6084/m9.figshare.5104873.v1 | null | Enamine | Ester | null | null | c1ccccc1 | null | Cl(=O)(=O)(=O)[O-].[Rh+].C(C)(=O)O.C1CCOC1 | null | null | COC(=O)/C(=C/CC[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@H](C)C(=O)OC)NC(=O)OC(C)(C)C>Cl(=O)(=O)(=O)[O-].[Rh+].C(C)(=O)O.C1CCOC1>COC(=O)C(CCC[C@@H](NC(=O)OCc1ccccc1)C(=O)N[C@H](C)C(=O)OC)NC(=O)OC(C)(C)C |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-fe2f4f1f21b644dbbc12c75cafdad403 | CCCCCCC(=O)NC(CNC(=O)N[C@@H](CCCC(NC(=O)OC(C)(C)C)C(=O)O)C(=O)N[C@H](C)C(=O)O)C(=O)O>>CCCCCCC(=O)NC(CNC(=O)N[C@@H](CCCC(N)C(=O)O)C(=O)N[C@H](C)C(=O)O)C(=O)O | C(=O)(O)C(CCC[C@H](NC(=O)NCC(NC(CCCCCC)=O)C(=O)O)C(=O)N[C@H](C)C(=O)O)NC(=O)OC(C)(C)C>>C(=O)(O)C(CCC[C@H](NC(=O)NCC(NC(CCCCCC)=O)C(=O)O)C(=O)N[C@H](C)C(=O)O)N | CC(C)(C)OC(=O)[NH:21][CH:20]([CH2:19][CH2:18][CH2:17][C@H:16]([NH:15][C:13]([NH:12][CH2:11][CH:10]([NH:9][C:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:8])[C:33](=[O:34])[OH:35])=[O:14])[C:25](=[O:26])[NH:27][C@H:28]([CH3:29])[C:30](=[O:31])[OH:32])[C:22](=[O:23])[OH:24]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6... | CCCCCCC(=O)NC(CNC(=O)N[C@@H](CCCC(NC(=O)OC(C)(C)C)C(=O)O)C(=O)N[C@H](C)C(=O)O)C(=O)O | CCCCCCC(=O)NC(CNC(=O)N[C@@H](CCCC(N)C(=O)O)C(=O)N[C@H](C)C(=O)O)C(=O)O | null | null | C(=O)(C(F)(F)F)O | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | null | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6] | null | [] | null | null | null | null | To 85.9 mg of 1b-5 under argon is treated with 500 μl of TFA according to Example 80. The volatiles are evaporated to a residue which is triturated with ether 3× and the ether is decanted. The residue is dried to give 77.9 mg of 1b-11 as a white solid. NMR (CD3OD) δ 0.80 (t, 3 H), 2.16 (t, 2 H), 3.22 (br s, 5 H), 3.58 ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | null | HO- | C(=O)(C(F)(F)F)O | null | null | CCCCCCC(=O)NC(CNC(=O)N[C@@H](CCCC(NC(=O)OC(C)(C)C)C(=O)O)C(=O)N[C@H](C)C(=O)O)C(=O)O>C(=O)(C(F)(F)F)O>CCCCCCC(=O)NC(CNC(=O)N[C@@H](CCCC(N)C(=O)O)C(=O)N[C@H](C)C(=O)O)C(=O)O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f65db27a2d674478893e33364067f34e | O=C1CC2(CCN(C(=O)c3ccccc3)CC2)Sc2sc([N+](=O)[O-])cc21>>O=C1CC2(CCNCC2)Sc2sc([N+](=O)[O-])cc21 | [N+](=O)([O-])C1=CC2=C(SC3(CC2=O)CCN(CC3)C(C3=CC=CC=C3)=O)S1.Cl>>Cl.[N+](=O)([O-])C1=CC2=C(SC3(CC2=O)CCNCC3)S1 | O=C(c1ccccc1)[N:8]1[CH2:7][CH2:6][C:5]2([CH2:4][C:3](=[O:2])[c:19]3[c:12]([s:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18]3)[S:11]2)[CH2:10][CH2:9]1>>[O:2]=[C:3]1[CH2:4][C:5]2([CH2:6][CH2:7][NH:8][CH2:9][CH2:10]2)[S:11][c:12]2[s:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][c:19]21 | O=C1CC2(CCN(C(=O)c3ccccc3)CC2)Sc2sc([N+](=O)[O-])cc21 | O=C1CC2(CCNCC2)Sc2sc([N+](=O)[O-])cc21 | null | null | CO | Reduction | Hydrogenolysis of tertiary amines | 061972243e5df2c50b2abe297b51515d793d6e04c114daffd44fd3c09d1f35a1 | 62cf08a8ae6315067a063b5b3495125ccbdaff6b2340ce1d3e1c7b6cde962ae4 | O=C1CC2(CCNCC2)Sc2sccc21 | O=C(-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5])-c1:c:c:c:c:c:1>>[C:5]-[C:4]-[NH;D2;+0:1]-[C:2]-[C:3] | 73 | [{"value": 73.0, "product": "Cl.[N+](=O)([O-])C1=CC2=C(SC3(CC2=O)CCNCC3)S1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of 1.1 g (2.9 mmol) Of 2'-nitro-1-(benzoyl)spiro(piperidine-4,6'-(6H)thieno[2,3-b]thiopyran)-4'(5'H)-one in 25 mL methanol was treated with 25 ml of 6N HCl and heated to reflux for 3 days. The reaction was cooled to ambient temperature and the solid collected and dried in vacuo, to give 680 mg (73%) of the... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Secondary amine | c1ccccc1.c1cc2c(s1)SC1(CC[NH]CC1)CC2 | c1cc2c(s1)SC1(CCNCC1)CC2 | c1cc2c(s1)SC1(CCNCC1)CC2 | HO- | CO | null | null | O=C1CC2(CCN(C(=O)c3ccccc3)CC2)Sc2sc([N+](=O)[O-])cc21>CO>O=C1CC2(CCNCC2)Sc2sc([N+](=O)[O-])cc21 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ec57176989cf4ac985f33c1e593bb213 | O=C1CC2(CCN(C(=O)c3ccccc3)CC2)Sc2sccc21>>O=C1CC2(CCNCC2)Sc2sccc21 | C(C1=CC=CC=C1)(=O)N1CCC2(CC(C3=C(S2)SC=C3)=O)CC1.Cl>>Cl.S1C=CC2=C1SC1(CC2=O)CCNCC1 | O=C(c1ccccc1)[N:8]1[CH2:7][CH2:6][C:5]2([CH2:4][C:3](=[O:2])[c:16]3[c:12]([s:13][cH:14][cH:15]3)[S:11]2)[CH2:10][CH2:9]1>>[O:2]=[C:3]1[CH2:4][C:5]2([CH2:6][CH2:7][NH:8][CH2:9][CH2:10]2)[S:11][c:12]2[s:13][cH:14][cH:15][c:16]21 | O=C1CC2(CCN(C(=O)c3ccccc3)CC2)Sc2sccc21 | O=C1CC2(CCNCC2)Sc2sccc21 | null | null | C(C)O | Reduction | Hydrogenolysis of tertiary amines | 061972243e5df2c50b2abe297b51515d793d6e04c114daffd44fd3c09d1f35a1 | 62cf08a8ae6315067a063b5b3495125ccbdaff6b2340ce1d3e1c7b6cde962ae4 | O=C1CC2(CCNCC2)Sc2sccc21 | O=C(-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5])-c1:c:c:c:c:c:1>>[C:5]-[C:4]-[NH;D2;+0:1]-[C:2]-[C:3] | null | [] | null | null | null | null | A solution of 14 g (40.99 mmol) of 1-benzoylspiro(piperidine-4,6'-(6H)thieno[2,3-b]thiopyran)-4'-(5'H)-one in 150 ml of ethanol was treated with 50 ml of 6N HCl and heated at reflux for 2 days. The reaction was cooled to room temperature and the solid collected by filtration. The solid was dried overnight in vacuo to g... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Secondary amine | c1ccccc1.c1cc2c(s1)SC1(CC[NH]CC1)CC2 | c1cc2c(s1)SC1(CCNCC1)CC2 | c1cc2c(s1)SC1(CCNCC1)CC2 | HO- | C(C)O | null | null | O=C1CC2(CCN(C(=O)c3ccccc3)CC2)Sc2sccc21>C(C)O>O=C1CC2(CCNCC2)Sc2sccc21 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ed27f126b77d43e6a1c1da3462a9297f | Cl.O=C1CC2(CCN(CCc3ccc([N+](=O)[O-])cc3)CC2)Sc2sccc21>>Cl.Cl.Cl.Nc1ccc(CCN2CCC3(CC2)CC(=O)c2ccsc2S3)cc1.Nc1ccc(CCN2CCC3(CC2)CC(=O)c2ccsc2S3)cc1.O | [OH-].[Na+].Cl.[N+](=O)([O-])C1=CC=C(C=C1)CCN1CCC2(CC(C3=C(S2)SC=C3)=O)CC1.Cl.C([O-])(O)=O.[Na+]>>O.Cl.Cl.NC1=CC=C(C=C1)CCN1CCC2(CC(C3=C(S2)SC=C3)=O)CC1.NC1=CC=C(C=C1)CCN1CCC3(CC(C2=C(S3)SC=C2)=O)CC1.Cl.Cl | [ClH:4].[O-][N+:5]([c:6]1[cH:28][cH:32][c:33]([CH2:34][CH2:35][N:36]2[CH2:7][CH2:14][C:15]3([CH2:18][C:19](=[O:20])[c:21]4[cH:22][cH:47][s:48][c:25]4[S:24]3)[CH2:38][CH2:37]2)[cH:51][cH:52]1)=[O:53]>>[ClH:2].[ClH:3].[ClH:4].[NH2:5][c:6]1[cH:7][cH:8][c:9]([CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][C:15]3([CH2:16][CH2:17]2)... | Cl.O=C1CC2(CCN(CCc3ccc([N+](=O)[O-])cc3)CC2)Sc2sccc21 | Cl.Cl.Cl.Nc1ccc(CCN2CCC3(CC2)CC(=O)c2ccsc2S3)cc1.Nc1ccc(CCN2CCC3(CC2)CC(=O)c2ccsc2S3)cc1.O | null | null | O.C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | c56dd5904255ec4f258ab23d7047a9b77ea93071792ad667135d8c6cd39478ca | 2bf816a2e72d2b6a7215a1d0134bbb0cd11b5ceb8cd441ecbc869f832ce16ff5 | O=C1CC2(CCN(CCc3ccccc3)CC2)Sc2sccc21.O=C1CC2(CCN(CCc3ccccc3)CC2)Sc2sccc21 | [O-]-[N+;H0;D3:1](=[O;H0;D1;+0:2])-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[cH;D2;+0:5]:[c:6](-[C:7]-[C:8]-[N;H0;D3;+0:9]2-[C:10]-[CH2;D2;+0:11]-[C;H0;D4;+0:12]3(-[C:13]-[C:14](=[O;D1;H0:15])-[c:16]4:[cH;D2;+0:17]:[cH;D2;+0:18]:[s;H0;D2;+0:19]:[c;H0;D3;+0:20]:4-[S;H0;D2;+0:21]-3)-[CH2;D2;+0:22]-[CH2;D2;+0:23]-2):[c:24]:[cH;D2;+0:... | null | [] | null | null | 45 | MINUTE | A solution Of 1.1 g (2.8 mmoles) of 1-(2-(p-nitrophenyl)ethyl)spiro(piperidine-4,6'-(6H)-thieno-[2,3-b]thiopyran)-4'(5'H)-one in 15 mL acetic acid and 20 mL H2O was treated with 15 mL of a solution of 15% TiCl3 in 20% HCl. The dark purple reaction mixture was stirred at room temperature for 45 minutes and poured into 2... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Tertiary amine.Monosulfide | Ketone.Primary amine.Primary amine.Tertiary amine.Tertiary amine.Monosulfide.Monosulfide | c1ccccc1.c1cc2c(s1)SC1(CC[NH]CC1)CC2 | c1ccccc1.c1cc2c(s1)SC1(CC[NH]CC1)CC2.c1ccccc1.c1cc2c(s1)SC1(CC[NH]CC1)CC2 | c1ccccc1.c1cc2c(s1)SC1(CC[NH]CC1)CC2.c1ccccc1.c1cc2c(s1)SC1(CC[NH]CC1)CC2 | null | O.C(C)(=O)O | null | 0.75 | Cl.O=C1CC2(CCN(CCc3ccc([N+](=O)[O-])cc3)CC2)Sc2sccc21>O.C(C)(=O)O>Cl.Cl.Cl.Nc1ccc(CCN2CCC3(CC2)CC(=O)c2ccsc2S3)cc1.Nc1ccc(CCN2CCC3(CC2)CC(=O)c2ccsc2S3)cc1.O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-2436bfb999cc4109bb710634b257b137 | BrCc1ccccc1.CCOC(=O)C1CCN(C(=O)c2ccccc2)CC1>>CCOC(=O)C1(Cc2ccccc2)CCN(C(=O)c2ccccc2)CC1 | C(C1=CC=CC=C1)Br.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].C(C1=CC=CC=C1)(=O)N1CCC(CC1)C(=O)OCC>>C(C)OC(=O)C1(CCN(CC1)C(C1=CC=CC=C1)=O)CC1=CC=CC=C1 | Br[CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:14][CH2:15][N:16]([C:17](=[O:18])[c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[CH2:25][CH2:26]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1([CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[CH2:14][CH2:15][N:16]([C:17](=[O:18])[c:... | BrCc1ccccc1.CCOC(=O)C1CCN(C(=O)c2ccccc2)CC1 | CCOC(=O)C1(Cc2ccccc2)CCN(C(=O)c2ccccc2)CC1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | cc17dfd0def644ca87e815e637357310f207eb90d8b3273b51858e3602d79eca | 0061a06af9fc64155952582b91b574e4abd8908ca14244f15179c2400b24dd08 | O=C(c1ccccc1)N1CCC(Cc2ccccc2)CC1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH;D3;+0:9]1-[C:10]-[C:11]-[#7:12]-[C:13]-[C:14]-1>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C;H0;D4;+0:9]1(-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:10]-[C:11]-[#7:12]-[C:13]-[C:14]-1 | 118.6 | [{"value": 118.6, "product": "C(C)OC(=O)C1(CCN(CC1)C(C1=CC=CC=C1)=O)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 7.84 g (30.0 mmoles) ethyl 1-benzoyl-4-piperidinecarboxylate (G. R. Clemo and E. Hoggarth, J. Chem. Soc., 41, (1941) in 60 ml dry. tetrahydrofuran at -78° C. under argon was added dropwise over 10 minutes 33.0 ml (33.0 mmoles) lithium bis(trimethylsilyl)amide in tetrahydrofuran and the resulting soluti... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | C1CC[NH]CC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | HBr | O1CCCC1 | null | 0.5 | BrCc1ccccc1.CCOC(=O)C1CCN(C(=O)c2ccccc2)CC1>O1CCCC1>CCOC(=O)C1(Cc2ccccc2)CCN(C(=O)c2ccccc2)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-503ce7328877430c83c2dad8690e18c2 | CCOC(=O)C1(Cc2ccccc2)CCN(C(=O)c2ccccc2)CC1>>O=C(c1ccccc1)N1CCC(Cc2ccccc2)(C(=O)O)CC1 | Cl.C(C1=CC=CC=C1)(=O)N1CCC(CC1)(C(=O)OCC)CC1=CC=CC=C1.CC(C)([O-])C.[K+]>>C(C1=CC=CC=C1)(=O)N1CCC(CC1)(C(=O)O)CC1=CC=CC=C1 | CC[O:22][C:20]([C:12]1([CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[CH2:11][CH2:10][N:9]([C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][cH:8]2)[CH2:24][CH2:23]1)=[O:21]>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[N:9]1[CH2:10][CH2:11][C:12]([CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)([C:20](=[O:21... | CCOC(=O)C1(Cc2ccccc2)CCN(C(=O)c2ccccc2)CC1 | O=C(c1ccccc1)N1CCC(Cc2ccccc2)(C(=O)O)CC1 | null | null | CS(=O)C | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(c1ccccc1)N1CCC(Cc2ccccc2)CC1 | 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] | 78.9 | [{"value": 75.0, "product": "C(C1=CC=CC=C1)(=O)N1CCC(CC1)(C(=O)O)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.9, "product": "C(C1=CC=CC=C1)(=O)N1CCC(CC1)(C(=O)O)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To 10.7 g (26 mmoles) crude ethyl 1-benzoyl-4-(phenylmethyl)-4-piperidinecarboxylate was added a solution of 14.6 g (130 mmoles) potassium tert-butoxide in 130 ml dimethyl sulfoxide. The resulting purple solution was stirred 2 hours to give a dark orange solution. The solution was poured into 500 ml rapidly stirred ice... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | Other | CS(=O)C | null | 2 | CCOC(=O)C1(Cc2ccccc2)CCN(C(=O)c2ccccc2)CC1>CS(=O)C>O=C(c1ccccc1)N1CCC(Cc2ccccc2)(C(=O)O)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-912fda52d8fa431a8028fa3907b7ca92 | O=C(c1ccccc1)N1CCC(Cc2ccccc2)(C(=O)O)CC1>>O=C(c1ccccc1)N1CCC2(CC1)Cc1ccccc1C2=O | C(C1=CC=CC=C1)(=O)N1CCC(CC1)(C(=O)O)CC1=CC=CC=C1>>C(C1=CC=CC=C1)(=O)N1CCC2(CC1)C(C1=CC=CC=C1C2)=O | O[C:22]([C:12]1([CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[CH2:11][CH2:10][N:9]([C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][cH:8]2)[CH2:14][CH2:13]1)=[O:23]>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[N:9]1[CH2:10][CH2:11][C:12]2([CH2:13][CH2:14]1)[CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][c:21]1[C:2... | O=C(c1ccccc1)N1CCC(Cc2ccccc2)(C(=O)O)CC1 | O=C(c1ccccc1)N1CCC2(CC1)Cc1ccccc1C2=O | null | null | O | Functional Group Interconversion | OtherReaction | 787ba820e569522607c2c82759edd12708de635414a7ad7ece07bc54eae6a030 | 6a71bb5a71b59feeb4f6a39b1b66fa450a058b64b0a3909e1a51c22473a141c5 | O=C(c1ccccc1)N1CCC2(CC1)Cc1ccccc1C2=O | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9])(-[C:10])-[C:11]>>[C:10]-[C:3]1(-[C:11])-[C:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](:[c:8]:[c:9])-[C;H0;D3;+0:1]-1=[O;D1;H0:2] | 62.2 | [{"value": 62.0, "product": "C(C1=CC=CC=C1)(=O)N1CCC2(CC1)C(C1=CC=CC=C1C2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.2, "product": "C(C1=CC=CC=C1)(=O)N1CCC2(CC1)C(C1=CC=CC=C1C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A solution of 6.14 g (19.0 mmoles) 1-benzoyl-4-(phenylmethyl)-4-piperidinecarboxylic acid in 61 ml concentrated sulfuzic acid was stirred 18 hours at room temperature to give a deep red solution. The solution was carefully diluted with ice-bath cooling with 300 ml H2O and extracted with 3×300 ml ethyl acetate. The extr... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ketone | c1ccccc1 | c1ccc2c(c1)CC1(CC[NH]CC1)C2 | c1ccccc1.c1ccc2c(c1)CC1(CC[NH]CC1)C2 | HO- | O | null | 18 | O=C(c1ccccc1)N1CCC(Cc2ccccc2)(C(=O)O)CC1>O>O=C(c1ccccc1)N1CCC2(CC1)Cc1ccccc1C2=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-81b58828189c480a90bc85d00cc71504 | O=C(c1ccccc1)N1CCC2(CC1)Cc1ccccc1C2=O>>O=C1c2ccccc2CC12CCNCC2 | C(C1=CC=CC=C1)(=O)N1CCC2(CC1)C(C1=CC=CC=C1C2)=O>>O=C1C2=CC=CC=C2CC12CCNCC2 | O=C(c1ccccc1)[N:13]1[CH2:12][CH2:11][C:10]2([C:2](=[O:1])[c:3]3[cH:4][cH:5][cH:6][cH:7][c:8]3[CH2:9]2)[CH2:15][CH2:14]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[CH2:9][C:10]12[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]2 | O=C(c1ccccc1)N1CCC2(CC1)Cc1ccccc1C2=O | O=C1c2ccccc2CC12CCNCC2 | null | null | Cl.C(C)O | Reduction | Hydrogenolysis of tertiary amines | 20ff99edc06d17eb1c5ccc5ceb37a19d52a788336a8df7f05fa1526dc6598528 | 62cf08a8ae6315067a063b5b3495125ccbdaff6b2340ce1d3e1c7b6cde962ae4 | O=C1c2ccccc2CC12CCNCC2 | O=C(-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5])-c1:c:c:c:c:c:1>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 77.4 | [{"value": 77.0, "product": "O=C1C2=CC=CC=C2CC12CCNCC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.4, "product": "O=C1C2=CC=CC=C2CC12CCNCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3.66 g (12.0 mmoles) 1'-benzoyl-1,3-dihydro-1-oxospiro-[2H-indene-2,4'-piperidine] in 90 ml ethanol and 30 ml 6N hydrochloric acid was heated at reflux for 42 hours. An additional 10 ml 6N hydrochloric acid was added and the solution was heated at reflux for 6 hours. The cooled solution was concentrated i... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Secondary amine | c1ccccc1.c1ccc2c(c1)CC1(CC[NH]CC1)C2 | c1ccc2c(c1)CC1(CCNCC1)C2 | c1ccc2c(c1)CC1(CCNCC1)C2 | HO- | Cl.C(C)O | null | null | O=C(c1ccccc1)N1CCC2(CC1)Cc1ccccc1C2=O>Cl.C(C)O>O=C1c2ccccc2CC12CCNCC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-605cac8cff47459890dbd04581014144 | O=C1c2ccccc2CC12CCNCC2.O=[N+]([O-])c1ccc(CCBr)cc1>>O=C1c2ccccc2CC12CCN(CCc1ccc([N+](=O)[O-])cc1)CC2 | O=C1C2=CC=CC=C2CC12CCNCC2.[N+](=O)([O-])C1=CC=C(CCBr)C=C1.C([O-])(O)=O.[Na+]>>O=C1C2=CC=CC=C2CC12CCN(CC2)CCC2=CC=C(C=C2)[N+](=O)[O-] | [O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[CH2:9][C:10]12[CH2:11][CH2:12][NH:13][CH2:25][CH2:26]2.Br[CH2:14][CH2:15][c:16]1[cH:17][cH:18][c:19]([N+:20](=[O:21])[O-:22])[cH:23][cH:24]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[CH2:9][C:10]12[CH2:11][CH2:12][N:13]([CH2:14][CH2:15][c:16]1[cH:17][cH:18][c:19]... | O=C1c2ccccc2CC12CCNCC2.O=[N+]([O-])c1ccc(CCBr)cc1 | O=C1c2ccccc2CC12CCN(CCc1ccc([N+](=O)[O-])cc1)CC2 | null | null | C(C)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b98f25b7f7ba26359793785ecff3964b918e34394e910ff6139ef5763b458f9f | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1c2ccccc2CC12CCN(CCc1ccccc1)CC2 | Br-[CH2;D2;+0:1]-[C:2]-[c:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]-[c:3])-[C:7]-[C:8] | 58 | [{"value": 58.0, "product": "O=C1C2=CC=CC=C2CC12CCN(CC2)CCC2=CC=C(C=C2)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.2, "product": "O=C1C2=CC=CC=C2CC12CCN(CC2)CCC2=CC=C(C=C2)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 0.60 g (3.0 moles) 1,3-dihydro-1-oxospiro[2H-indene-2,4'-piperidine], 0.71 g (3.1 mmoles) 4-nitrophenethyl bromide, and 0.28 g (3.3 mmoles) sodium bicarbonate in 3 ml ethanol was heated at reflux for 6 hours. The solvent was removed in vacuo and the residue was partitioned between 20 ml ethyl acetate and 5... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1ccc2c(c1)CC1(CCNCC1)C2 | c1ccc2c(c1)CC1(CC[NH]CC1)C2 | c1ccc2c(c1)CC1(CC[NH]CC1)C2.c1ccccc1 | HBr | C(C)O | null | null | O=C1c2ccccc2CC12CCNCC2.O=[N+]([O-])c1ccc(CCBr)cc1>C(C)O>O=C1c2ccccc2CC12CCN(CCc1ccc([N+](=O)[O-])cc1)CC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-5dfbaed87b85463b84e1def719b9b3e4 | CC(=O)N1CCC2(CC1)Cc1ccc([N+](=O)[O-])cc1C2=O>>O=C1c2cc([N+](=O)[O-])ccc2CC12CCNCC2 | C(C)(=O)N1CCC2(CC1)C(C1=CC(=CC=C1C2)[N+](=O)[O-])=O.Cl.Cl>>Cl.[N+](=O)([O-])C1=CC=C2CC3(CCNCC3)C(C2=C1)=O | CC(=O)[N:17]1[CH2:16][CH2:15][C:14]2([C:3](=[O:2])[c:4]3[cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11][c:12]3[CH2:13]2)[CH2:19][CH2:18]1>>[O:2]=[C:3]1[c:4]2[cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11][c:12]2[CH2:13][C:14]12[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]2 | CC(=O)N1CCC2(CC1)Cc1ccc([N+](=O)[O-])cc1C2=O | O=C1c2cc([N+](=O)[O-])ccc2CC12CCNCC2 | null | null | C(C)O | Reduction | Hydrogenolysis of tertiary amines | b1cb52270d580532affb153faf9496db8bc0156ff196af48791beb9b6968e4c4 | 62cf08a8ae6315067a063b5b3495125ccbdaff6b2340ce1d3e1c7b6cde962ae4 | O=C1c2ccccc2CC12CCNCC2 | C-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 74.5 | [{"value": 74.0, "product": "Cl.[N+](=O)([O-])C1=CC=C2CC3(CCNCC3)C(C2=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.5, "product": "Cl.[N+](=O)([O-])C1=CC=C2CC3(CCNCC3)C(C2=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 0.216 g (0.75 mmol) 1'-acetyl-1,3-dihydro-1-oxo-6-nitrospiro[2H-indene-2,4'-piperidine] and 2 ml (6 mmol) 3N hydrochloric acid in 6 ml ethanol was heated at reflux for 18 hours. Another 0.2 ml (0.6 mmol) 3N hydrochloric acid was added and the solution was heated at reflux for 4 hours, then cooled to room ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Secondary amine | c1ccc2c(c1)CC1(CC[NH]CC1)C2 | c1ccc2c(c1)CC1(CCNCC1)C2 | c1ccc2c(c1)CC1(CCNCC1)C2 | HO- | C(C)O | null | null | CC(=O)N1CCC2(CC1)Cc1ccc([N+](=O)[O-])cc1C2=O>C(C)O>O=C1c2cc([N+](=O)[O-])ccc2CC12CCNCC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-55054c5686e74d75b17896bf1ce5c7ef | CC(=O)N1CCC2(CC1)Cc1ccc([N+](=O)[O-])cc1C2=O>>CC(=O)N1CCC2(CC1)Cc1ccc(N)cc1C2=O | C([O-])(O)=O.[Na+].C(C)(=O)N1CCC2(CC1)C(C1=CC(=CC=C1C2)[N+](=O)[O-])=O.[OH-].[Na+]>>C(C)(=O)N1CCC2(CC1)C(C1=CC(=CC=C1C2)N)=O | O=[N+:15]([O-])[c:14]1[cH:13][cH:12][c:11]2[c:17]([cH:16]1)[C:18](=[O:19])[C:7]1([CH2:6][CH2:5][N:4]([C:2]([CH3:1])=[O:3])[CH2:9][CH2:8]1)[CH2:10]2>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][C:7]2([CH2:8][CH2:9]1)[CH2:10][c:11]1[cH:12][cH:13][c:14]([NH2:15])[cH:16][c:17]1[C:18]2=[O:19] | CC(=O)N1CCC2(CC1)Cc1ccc([N+](=O)[O-])cc1C2=O | CC(=O)N1CCC2(CC1)Cc1ccc(N)cc1C2=O | null | [Cl-].[Ti+3].[Cl-].[Cl-] | Cl.O.C(C)(=O)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C1c2ccccc2CC12CCNCC2 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 112.3 | [{"value": 112.3, "product": "C(C)(=O)N1CCC2(CC1)C(C1=CC(=CC=C1C2)N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 0.29 g (1.0 mmole) 1'-acetyl-1,3-dihydro-6-nitro-1-oxospiro[2H-indene-2,4'-piperidine] in 4 ml acetic acid was added 3.75 ml (4.3 mmoles) of 15% titanium (III) chloride solution in 20-30% aqueous hydrochloric acid dropwise and portionwise over 2 hours. The reaction mixture was made basic (pH 10) with s... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2c(c1)CC1(CC[NH]CC1)C2 | Other | [Cl-].[Ti+3].[Cl-].[Cl-].Cl.O.C(C)(=O)O | null | 2 | CC(=O)N1CCC2(CC1)Cc1ccc([N+](=O)[O-])cc1C2=O>[Cl-].[Ti+3].[Cl-].[Cl-].Cl.O.C(C)(=O)O>CC(=O)N1CCC2(CC1)Cc1ccc(N)cc1C2=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-35cf24df8bd9426d8ecf4c4423920048 | CCOC(=O)N(CCBr)CCBr.O=C1CCCc2ccccc21>>CCOC(=O)N1CCC2(CCc3ccccc3C2=O)CC1 | C1(CCCC2=CC=CC=C12)=O.BrCCN(C(OCC)=O)CCBr.[H-].[Na+]>>C(C)OC(=O)N1CCC2(CC1)C(C1=CC=CC=C1CC2)=O | Br[CH2:8][CH2:7][N:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:20][CH2:21]Br.[CH2:9]1[CH2:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[C:18]1=[O:19]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[C:18]2=[O:19])[CH2:20][CH2:21]1 | CCOC(=O)N(CCBr)CCBr.O=C1CCCc2ccccc21 | CCOC(=O)N1CCC2(CCc3ccccc3C2=O)CC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 174cb1ade1a683a04eb358fc59febf7c715b90f9543d7ee4978ea7230242efd8 | fc480cd11c4523824dc79fb530b6fe43274a09b2c3c6b9d6ec28ea3488f5f252 | O=C1c2ccccc2CCC12CCNCC2 | Br-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[N;H0;D3;+0:3](-[C:4]-[CH2;D2;+0:5]-Br)-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9].[C:10]-[C:11]-[CH2;D2;+0:12]-[C:13](=[O;D1;H0:14])-[c:15]>>[C:10]-[C:11]-[C;H0;D4;+0:12]1(-[CH2;D2;+0:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:3](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9])-[C:4]-[CH2;D2;+0:5]-1)-[C:13](=[O;D1;H0:14])-[c... | 26 | [{"value": 26.0, "product": "C(C)OC(=O)N1CCC2(CC1)C(C1=CC=CC=C1CC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 25.6, "product": "C(C)OC(=O)N1CCC2(CC1)C(C1=CC=CC=C1CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 14 | HOUR | To a solution of 2.92 g (20.0 mmoles) 1-tetralone and 9.0 g (30.0 mmoles) ethyl bis(2-bromoethyl)carbamate (S. Huybuchts and G. J. Hoornaert, Synth. Commum., 11, 17 (1981) in 20 ml dry dimethylformamide heated to 50° C. under argon was added in portions 2.00 g (50.0 mmol) of 60% sodium hydride dispersion is mineral oil... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Carbamic ester.Ketone | Carbamic ester.Ketone | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCC1(CC[NH]CC1)C2 | c1ccc2c(c1)CCC1(CC[NH]CC1)C2 | HBr | CN(C=O)C | 50 | 14 | CCOC(=O)N(CCBr)CCBr.O=C1CCCc2ccccc21>CN(C=O)C>CCOC(=O)N1CCC2(CCc3ccccc3C2=O)CC1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-1235741b27ab474a8d96b42ef5a69254 | CCN1CCC2(CCc3ccccc3C2=O)CC1>>O=C1c2ccccc2CCC12CCNCC2 | C(C)N1CCC2(CC1)C(C1=CC=CC=C1CC2)=O>>O=C1C2=CC=CC=C2CCC12CCNCC2 | CC[N:14]1[CH2:13][CH2:12][C:11]2([C:2](=[O:1])[c:3]3[cH:4][cH:5][cH:6][cH:7][c:8]3[CH2:9][CH2:10]2)[CH2:16][CH2:15]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[CH2:9][CH2:10][C:11]12[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]2 | CCN1CCC2(CCc3ccccc3C2=O)CC1 | O=C1c2ccccc2CCC12CCNCC2 | null | null | [OH-].[K+].C(C)O | Deprotection | Hydrogenolysis of tertiary amines | 57f31c421a16f46cceb8712fcca8a76ec9121c3c7e079834fb51cccafc97fdfe | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | O=C1c2ccccc2CCC12CCNCC2 | C-C-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 78 | [{"value": 78.0, "product": "O=C1C2=CC=CC=C2CCC12CCNCC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.7, "product": "O=C1C2=CC=CC=C2CCC12CCNCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 1.84 g (6.4 mmoles) ethyl 3,4-dihydro-1-oxospiro[naphthalene-2(1H),4'piperidine] in 32 ml ethanol and 16 ml of 50% potassium hydroxide solution was heated at reflux for 18 hours. The solution was concentrated in vacuo to remove ethanol and the aqueous residue was extracted with 3×40 ml ether. The combined... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccc2c(c1)CCC1(CC[NH]CC1)C2 | c1ccc2c(c1)CCC1(CCNCC1)C2 | c1ccc2c(c1)CCC1(CCNCC1)C2 | Other | [OH-].[K+].C(C)O | null | null | CCN1CCC2(CCc3ccccc3C2=O)CC1>[OH-].[K+].C(C)O>O=C1c2ccccc2CCC12CCNCC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-76aa8d7938414f228e1d6142199342a2 | CC(=O)N1CCC2(CCc3ccc(NS(C)(=O)=O)cc3C2=O)CC1>>CS(=O)(=O)Nc1ccc2c(c1)C(=O)C1(CCNCC1)CC2 | Cl.C(C)(=O)N1CCC2(CC1)C(C1=CC(=CC=C1CC2)NS(=O)(=O)C)=O.Cl>>Cl.CS(=O)(=O)NC1=CC=C2CCC3(CCNCC3)C(C2=C1)=O | CC(=O)[N:17]1[CH2:16][CH2:15][C:14]2([C:12](=[O:13])[c:10]3[c:9]([cH:8][cH:7][c:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])[cH:11]3)[CH2:21][CH2:20]2)[CH2:19][CH2:18]1>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[C:12](=[O:13])[C:14]1([CH2:15][CH2:16][NH:17][CH2:18][CH2:19]1)[CH2:20][CH2:21]2 | CC(=O)N1CCC2(CCc3ccc(NS(C)(=O)=O)cc3C2=O)CC1 | CS(=O)(=O)Nc1ccc2c(c1)C(=O)C1(CCNCC1)CC2 | null | null | C(C)O | Reduction | Hydrogenolysis of tertiary amines | 9225235603486c1bf83e27f088d5a1b189d6acdd2949a4da12907d46f5e44d14 | 62cf08a8ae6315067a063b5b3495125ccbdaff6b2340ce1d3e1c7b6cde962ae4 | O=C1c2ccccc2CCC12CCNCC2 | C-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 67 | [{"value": 67.0, "product": "Cl.CS(=O)(=O)NC1=CC=C2CCC3(CCNCC3)C(C2=C1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 0.53 g (1.5 mmoles) 1'-acetyl-3,4-dihydro-7-methanesulfonamido-1-oxospiro[naphthalene-2(1H),4'-piperidine] in 15 ml ethanol and 5 ml 3N hydrochloric acid was heated at reflux for 18 hours. An additional 10 ml 3N hydrochloric acid was added and the solution was heatea at reflux for 5 hours, then cooled to ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Secondary amine | c1ccc2c(c1)CCC1(CC[NH]CC1)C2 | c1ccc2c(c1)CCC1(CCNCC1)C2 | c1ccc2c(c1)CCC1(CCNCC1)C2 | HO- | C(C)O | null | null | CC(=O)N1CCC2(CCc3ccc(NS(C)(=O)=O)cc3C2=O)CC1>C(C)O>CS(=O)(=O)Nc1ccc2c(c1)C(=O)C1(CCNCC1)CC2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-497ce0dac18148448d14e82b382fc215 | c1ccc(CN2CCCC3(Cc4ccccc4O3)C2)cc1>>c1ccc2c(c1)CC1(CCCNC1)O2 | C(C1=CC=CC=C1)N1CC2(CCC1)OC1=C(C2)C=CC=C1.ClC(C)OC(=O)Cl>>N1CC2(CCC1)OC1=C(C2)C=CC=C1 | c1ccc(C[N:12]2[CH2:11][CH2:10][CH2:9][C:8]3([CH2:7][c:5]4[c:4]([cH:3][cH:2][cH:1][cH:6]4)[O:14]3)[CH2:13]2)cc1>>[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[CH2:7][C:8]1([CH2:9][CH2:10][CH2:11][NH:12][CH2:13]1)[O:14]2 | c1ccc(CN2CCCC3(Cc4ccccc4O3)C2)cc1 | c1ccc2c(c1)CC1(CCCNC1)O2 | null | null | ClC(C)Cl | Deprotection | Hydrogenolysis of tertiary amines | 1026015d984d7b2d2f7382796918788fa1ecd79e4b2ec66ef8b8a45af2877fa7 | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | c1ccc2c(c1)CC1(CCCNC1)O2 | [#8:1]-[C:2]-[C:3]-[N;H0;D3;+0:4](-C-c1:c:c:c:c:c:1)-[C:5]-[C:6]>>[#8:1]-[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6] | 94.2 | [{"value": 94.2, "product": "N1CC2(CCC1)OC1=C(C2)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 13 g (46 mmole) of 1'-benzyl-2,3-dihydrospiro(benzofuran-2,3'-piperidine) in 100 mL dichloroethane was treated with 7.31 g (5.2 mL, 51 mmoles) of 1-chloroethylchloroformate at room temperature for 1/2 hour. The reaction mixture was concentrated and the residue dissolved in CH3OH and heated to reflux for 1... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.c1ccc2c(c1)CC1(CCC[NH]C1)O2 | c1ccc2c(c1)CC1(CCCNC1)O2 | c1ccc2c(c1)CC1(CCCNC1)O2 | Other | ClC(C)Cl | null | null | c1ccc(CN2CCCC3(Cc4ccccc4O3)C2)cc1>ClC(C)Cl>c1ccc2c(c1)CC1(CCCNC1)O2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-898d32e6ca3b42fd8dca89c85c0414f7 | CC(=O)N1CCCC2(Cc3cc(NS(C)(=O)=O)ccc3O2)C1>>CS(=O)(=O)Nc1ccc2c(c1)CC1(CCCNC1)O2 | C(C)(=O)N1CC2(CCC1)OC1=C(C2)C=C(C=C1)NS(=O)(=O)C.Cl>>Cl.CS(=O)(=O)NC=1C=CC2=C(CC3(CNCCC3)O2)C1 | CC(=O)[N:17]1[CH2:16][CH2:15][CH2:14][C:13]2([CH2:12][c:10]3[c:9]([cH:8][cH:7][c:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])[cH:11]3)[O:19]2)[CH2:18]1>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[CH2:12][C:13]1([CH2:14][CH2:15][CH2:16][NH:17][CH2:18]1)[O:19]2 | CC(=O)N1CCCC2(Cc3cc(NS(C)(=O)=O)ccc3O2)C1 | CS(=O)(=O)Nc1ccc2c(c1)CC1(CCCNC1)O2 | null | null | C(C)O | Reduction | Hydrogenolysis of tertiary amines | 1dd4a4692504beab3ace65d954d95be83e12049235aae9a5a01d0ed1c877d2f6 | 62cf08a8ae6315067a063b5b3495125ccbdaff6b2340ce1d3e1c7b6cde962ae4 | c1ccc2c(c1)CC1(CCCNC1)O2 | C-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]-[#8:6]>>[#8:6]-[C:5]-[C:4]-[NH;D2;+0:1]-[C:2]-[C:3] | null | [] | null | null | null | null | A solution of 3.6 g (11.09 mmole) of 1'-Acetyl-2,3-dihydro-5-methanesulfonamidospiro(benzofuran-2,3'-piperidine) in 100 mL ethanol was treated with 50 mL 6 N hydrochloric acid and heated to reflux for 18 hours. The reaction was concentrated to dryness and the residue crystallized from ethanol to give 2.77 g of products... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Secondary amine | c1ccc2c(c1)CC1(CCC[NH]C1)O2 | c1ccc2c(c1)CC1(CCCNC1)O2 | c1ccc2c(c1)CC1(CCCNC1)O2 | HO- | C(C)O | null | null | CC(=O)N1CCCC2(Cc3cc(NS(C)(=O)=O)ccc3O2)C1>C(C)O>CS(=O)(=O)Nc1ccc2c(c1)CC1(CCCNC1)O2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-65ca1e4e59264f35b5d4a1e71549ea75 | CS(=O)(=O)Nc1ccc(CCOS(C)(=O)=O)cc1.O=C1CC2(CCCNC2)Oc2ccccc21>>CS(=O)(=O)Nc1ccc(CCN2CCCC3(CC(=O)c4ccccc4O3)C2)cc1 | C([O-])(O)=O.[Na+].C(C(=O)O)(=O)O.N1CC2(CCC1)OC1=C(C(C2)=O)C=CC=C1.S(C)(=O)(=O)OCCC1=CC=C(C=C1)NS(=O)(=O)C.C([O-])(O)=O.[Na+]>>C(C(=O)O)(=O)O.CS(=O)(=O)NC1=CC=C(C=C1)CCN1CC2(CCC1)OC1=C(C(C2)=O)C=CC=C1 | CS(=O)(=O)O[CH2:11][CH2:10][c:9]1[cH:8][cH:7][c:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])[cH:29][cH:28]1.[NH:12]1[CH2:13][CH2:14][CH2:15][C:16]2([CH2:17][C:18](=[O:19])[c:20]3[cH:21][cH:22][cH:23][cH:24][c:25]3[O:26]2)[CH2:27]1>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([CH2:10][CH2:11][N:12]2[CH2:13][CH2:... | CS(=O)(=O)Nc1ccc(CCOS(C)(=O)=O)cc1.O=C1CC2(CCCNC2)Oc2ccccc21 | CS(=O)(=O)Nc1ccc(CCN2CCCC3(CC(=O)c4ccccc4O3)C2)cc1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | Alkylation of amines | c07f3c636c847819d4f9c223819232dae13e0870974641de199c668de8a7ed5a | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=C1CC2(CCCN(CCc3ccccc3)C2)Oc2ccccc21 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[c:3].[#8:4]-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[#8:4]-[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[C:2]-[c:3])-[C:8]-[C:9] | null | [] | null | null | null | null | A solution of 560 mg (258 mmole) of 3,4-dihydrospiro-[(2H)-1-benzopyran-2,3'-piperidine]4-one in 20 mL ethanol was treated with 880 mg (3 mmoles) of 2-(4-methanesulfonamidophenyl)ethyl mesylate and 0.5 g sodium bicarbonate and heated to reflux for 48 hours. The reaction was cooled to room temperature, poured into satur... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | c1ccc2c(c1)CCC1(CCCNC1)O2 | c1ccc2c(c1)CCC1(CCC[NH]C1)O2 | c1ccccc1.c1ccc2c(c1)CCC1(CCC[NH]C1)O2 | MsOH.HO- | C(C)O | null | null | CS(=O)(=O)Nc1ccc(CCOS(C)(=O)=O)cc1.O=C1CC2(CCCNC2)Oc2ccccc21>C(C)O>CS(=O)(=O)Nc1ccc(CCN2CCCC3(CC(=O)c4ccccc4O3)C2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6aeb04d026c546f9b1095e74fc25312b | CC(Cl)OC(=O)Cl.CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCCN(Cc3ccccc3)C1)O2>>CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCCNC1)O2.Cl | C([O-])(O)=O.[Na+].CS(=O)(=O)NC=1C=CC2=C(C(CC3(CN(CCC3)CC3=CC=CC=C3)O2)=O)C1.C(C)(C)N(CC)C(C)C.ClC(=O)OC(C)Cl>>Cl.CS(=O)(=O)NC=1C=CC2=C(C(CC3(CNCCC3)O2)=O)C1 | CC(Cl)OC(=O)[Cl:22].c1ccc(C[N:19]2[CH2:18][CH2:17][CH2:16][C:15]3([CH2:14][C:12](=[O:13])[c:10]4[c:9]([cH:8][cH:7][c:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])[cH:11]4)[O:21]3)[CH2:20]2)cc1>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[C:12](=[O:13])[CH2:14][C:15]1([CH2:16][CH2:17][CH2:18][NH:... | CC(Cl)OC(=O)Cl.CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCCN(Cc3ccccc3)C1)O2 | CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCCNC1)O2.Cl | null | null | ClC(C)Cl | Miscellaneous | OtherReaction | 275fd43c0f08bde74a8898d2475fc1fe25be078812dabd4b8248cda02e1ce012 | 8680972761abf0bd12e62e23250487041204d99e9f76a29275e470fb95a71c86 | O=C1CC2(CCCNC2)Oc2ccccc21 | C-C(-Cl)-O-C(=O)-[Cl;H0;D1;+0:1].[#8:2]-[C:3]-[C:4]-[N;H0;D3;+0:5](-C-c1:c:c:c:c:c:1)-[C:6]-[C:7]>>[#8:2]-[C:3]-[C:4]-[NH;D2;+0:5]-[C:6]-[C:7].[ClH;D0;+0:1] | 67.7 | [{"value": 67.7, "product": "Cl.CS(=O)(=O)NC=1C=CC2=C(C(CC3(CNCCC3)O2)=O)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | A solution of 7 g (17.47 mmols) of 6-methanesulfonamido-1'-benzyl-3,4-dihydrospiro-[(2H)-1-benzopyran-2,3'-piperidine]-4-one in 250 mL dichloroethane was treated with 5.6 g (43.7 mmole) of diisopropylethylamine, and 6.24 g (43.7 mmoles) of 1-chloroethyl chloroformate. The reaction was stirred at room temperature for 24... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary halide.Ether.Tertiary amine | Secondary amine | c1ccccc1.c1ccc2c(c1)CCC1(CCC[NH]C1)O2 | c1ccc2c(c1)CCC1(CCCNC1)O2 | c1ccc2c(c1)CCC1(CCCNC1)O2 | HCl | ClC(C)Cl | null | 24 | CC(Cl)OC(=O)Cl.CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCCN(Cc3ccccc3)C1)O2>ClC(C)Cl>CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCCNC1)O2.Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-929bcdee11ce49d59e2a83b23d640eb8 | CC(Cl)OC(=O)Cl.CN1CCC2(CC1)Cc1ccc(NS(C)(=O)=O)cc1CO2>>CS(=O)(=O)Nc1ccc2c(c1)COC1(CCNCC1)C2.Cl | CN1CCC2(CC1)OCC1=C(C2)C=CC(=C1)NS(=O)(=O)C.CN(C1=CC=CC2=CC=CC(=C12)N(C)C)C.ClC(=O)OC(C)Cl>>Cl.CS(=O)(=O)NC1=CC2=C(CC3(CCNCC3)OC2)C=C1 | CC(Cl)OC(=O)[Cl:21].C[N:17]1[CH2:16][CH2:15][C:14]2([O:13][CH2:12][c:10]3[c:9]([cH:8][cH:7][c:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])[cH:11]3)[CH2:20]2)[CH2:19][CH2:18]1>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[CH2:12][O:13][C:14]1([CH2:15][CH2:16][NH:17][CH2:18][CH2:19]1)[CH2:20]2.[Cl... | CC(Cl)OC(=O)Cl.CN1CCC2(CC1)Cc1ccc(NS(C)(=O)=O)cc1CO2 | CS(=O)(=O)Nc1ccc2c(c1)COC1(CCNCC1)C2.Cl | null | null | ClC(C)Cl | Miscellaneous | OtherReaction | 77ac135b0fa246a6fefda7e08ae112cceb419f1d60863dd6eb2ea9e92853875f | 8680972761abf0bd12e62e23250487041204d99e9f76a29275e470fb95a71c86 | c1ccc2c(c1)COC1(CCNCC1)C2 | C-C(-Cl)-O-C(=O)-[Cl;H0;D1;+0:1].C-[N;H0;D3;+0:2](-[C:3]-[C:4])-[C:5]-[C:6]>>[C:4]-[C:3]-[NH;D2;+0:2]-[C:5]-[C:6].[ClH;D0;+0:1] | null | [] | null | null | null | null | To a solution of 1,4-dihydro-1'-methyl-7-methanesulfonamido-spiro[(3H)-2-benzopyran-3,4'-piperidine](0.575 g) and N,N,N',N'-tetramethyl-1,8-napthalenediamine (proton sponge) (0.6 g) in dichloroethane under nitrogen at 0° C. was added 1-chloroethyl chloroformate (0.613 ml). The mixture was stirred at reflux for 2 hours,... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary halide.Ether.Tertiary amine | Secondary amine | c1ccc2c(c1)COC1(CC[NH]CC1)C2 | c1ccc2c(c1)COC1(CCNCC1)C2 | c1ccc2c(c1)COC1(CCNCC1)C2 | HCl | ClC(C)Cl | null | null | CC(Cl)OC(=O)Cl.CN1CCC2(CC1)Cc1ccc(NS(C)(=O)=O)cc1CO2>ClC(C)Cl>CS(=O)(=O)Nc1ccc2c(c1)COC1(CCNCC1)C2.Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-11292f8d3ee3493ab3e125d923f45655 | CC(=O)c1ccccc1O.O=C1CCN(C(=O)c2ccccc2)CC1>>O=C1CC2(CCN(C(=O)c3ccccc3)CC2)Oc2ccccc21 | C(C)(=O)C1=C(C=CC=C1)O.C(C1=CC=CC=C1)(=O)N1CCC(CC1)=O.N1CCCC1>>C(C1=CC=CC=C1)(=O)N1CCC2(CC1)OC1=C(C(C2)=O)C=CC=C1 | [O:1]=[C:2]([CH3:3])[c:24]1[c:19]([OH:18])[cH:20][cH:21][cH:22][cH:23]1.O=[C:4]1[CH2:5][CH2:6][N:7]([C:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16][CH2:17]1>>[O:1]=[C:2]1[CH2:3][C:4]2([CH2:5][CH2:6][N:7]([C:8](=[O:9])[c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[CH2:16][CH2:17]2)[O:18][c:19]2[cH:20][cH... | CC(=O)c1ccccc1O.O=C1CCN(C(=O)c2ccccc2)CC1 | O=C1CC2(CCN(C(=O)c3ccccc3)CC2)Oc2ccccc21 | null | null | CO | Heteroatom Alkylation and Arylation | spiro-chromanone | 516e17e36e6da47114ec867780566e28862277ef4db6e563ed68fe6015ca5775 | 2b19ddad93f276f7cba72518a5f5b44fb4fd6e49b358f1173e7b2c08a31b3f60 | O=C1CC2(CCN(C(=O)c3ccccc3)CC2)Oc2ccccc21 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[CH3;D1;+0:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[OH;D1;+0:12]):[c:13]>>[O;D1;H0:9]=[C:8]1-[CH2;D2;+0:7]-[C;H0;D4;+0:1]2(-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-2)-[O;H0;D2;+0:12]-[c:11](:[c:13]):[c:10]-1 | 68,961.6 | [{"value": 68961.6, "product": "C(C1=CC=CC=C1)(=O)N1CCC2(CC1)OC1=C(C(C2)=O)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-acetylphenol (5 g, 0.037 mmol), 1-benzoyl-4-piperidone (7.5 g, 0.037 mmol), pyrrolidine (2.6 g, 0.037 mol) and CH3OH (50 ml) was heated at reflux for 8 hours. After cooling to room temperature overnight, the solid was filtered to yield 8.2 g of 1'-benzoyl-3,4-dihydro-spiro[(2H)-1-benzopyran-2,4'-piperid... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Aromatic alcohol | Ketone.Ether | C1CC[NH]CC1 | c1ccc2c(c1)CCC1(CC[NH]CC1)O2 | c1ccccc1.c1ccc2c(c1)CCC1(CC[NH]CC1)O2 | HO- | CO | null | null | CC(=O)c1ccccc1O.O=C1CCN(C(=O)c2ccccc2)CC1>CO>O=C1CC2(CCN(C(=O)c3ccccc3)CC2)Oc2ccccc21 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f5952f2d3c1a47b8a5eff37ecec2b712 | CN1CCC2(CC1)CC(=O)c1ccccc1O2.O=[N+]([O-])O>>CN1CCC2(CC1)CC(=O)c1cc([N+](=O)[O-])ccc1O2 | C(C)(=O)OCC.C([O-])(O)=O.[Na+].CN1CCC2(CC1)OC1=C(C(C2)=O)C=CC=C1.[N+](=O)(O)[O-].[N+](=O)(O)[O-]>>CN1CCC2(CC1)OC1=C(C(C2)=O)C=C(C=C1)[N+](=O)[O-] | [CH3:1][N:2]1[CH2:3][CH2:4][C:5]2([CH2:6][CH2:7]1)[CH2:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][cH:17][cH:18][c:19]1[O:20]2.O[N+:14](=[O:15])[O-:16]>>[CH3:1][N:2]1[CH2:3][CH2:4][C:5]2([CH2:6][CH2:7]1)[CH2:8][C:9](=[O:10])[c:11]1[cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18][c:19]1[O:20]2 | CN1CCC2(CC1)CC(=O)c1ccccc1O2.O=[N+]([O-])O | CN1CCC2(CC1)CC(=O)c1cc([N+](=O)[O-])ccc1O2 | null | null | S(O)(O)(=O)=O | Functional Group Addition | Aromatic nitration with HNO3 | 3e8bba8cfd479ea26838cd4df10d0b1719e48d1515854da8f965d36d40f55885 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | O=C1CC2(CCNCC2)Oc2ccccc21 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[O;D1;H0:4]=[C:5]-[c:6]:[c:7]:[cH;D2;+0:8]:[c:9]:[c:10]>>[O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[c;H0;D3;+0:8](:[c:7]:[c:6]-[C:5]=[O;D1;H0:4]):[c:9]:[c:10] | 77 | [{"value": 77.0, "product": "CN1CCC2(CC1)OC1=C(C(C2)=O)C=C(C=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.7, "product": "CN1CCC2(CC1)OC1=C(C(C2)=O)C=C(C=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | Sulfuric acid (55 ml) was cooled to 0° C. and was stirred as 3,4-dihydro-1'-methyl-spiro[2H-1-benzopyran-2,4'-piperidin]-4-one (11.56 g, 0.05 mol) was added over 20 minutes. Some gum separated. A solution of 90% nitric acid (2.5 ml, 0.0525 mol) in sulfuric acid (5 ml) was added over 20 minutes. The mixture was stirred ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccc2c(c1)CCC1(CC[NH]CC1)O2 | c1ccc2c(c1)CCC1(CC[NH]CC1)O2 | c1ccc2c(c1)CCC1(CC[NH]CC1)O2 | HO- | S(O)(O)(=O)=O | 0 | 2 | CN1CCC2(CC1)CC(=O)c1ccccc1O2.O=[N+]([O-])O>S(O)(O)(=O)=O>CN1CCC2(CC1)CC(=O)c1cc([N+](=O)[O-])ccc1O2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b71bc264b15d49928dd81de121d205e8 | CN1CCC2(CC1)CC(=O)c1cc([N+](=O)[O-])ccc1O2>>CN1CCC2(CC1)CC(=O)c1cc(N)ccc1O2 | CN1CCC2(CC1)OC1=C(C(C2)=O)C=C(C=C1)[N+](=O)[O-]>>NC=1C=CC2=C(C(CC3(CCN(CC3)C)O2)=O)C1 | O=[N+:14]([O-])[c:13]1[cH:12][c:11]2[c:17]([cH:16][cH:15]1)[O:18][C:5]1([CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]1)[CH2:8][C:9]2=[O:10]>>[CH3:1][N:2]1[CH2:3][CH2:4][C:5]2([CH2:6][CH2:7]1)[CH2:8][C:9](=[O:10])[c:11]1[cH:12][c:13]([NH2:14])[cH:15][cH:16][c:17]1[O:18]2 | CN1CCC2(CC1)CC(=O)c1cc([N+](=O)[O-])ccc1O2 | CN1CCC2(CC1)CC(=O)c1cc(N)ccc1O2 | null | [Ni] | C(C)(=O)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C1CC2(CCNCC2)Oc2ccccc21 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 75.1 | [{"value": 75.0, "product": "NC=1C=CC2=C(C(CC3(CCN(CC3)C)O2)=O)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.1, "product": "NC=1C=CC2=C(C(CC3(CCN(CC3)C)O2)=O)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The 3,4-dihydro-1'-methyl-6-nitro-spiro[2H-1-benzopyran-2,4'-piperdin]-4-one (11.2 g, 0.04 mol) was dissolved in acetic acid (200 ml) and was hydrogenated using two "lab spoon" spatulas of Raney nickel catalyst in a Parr shaker. The theoretical amount of hydrogen was absorbed in 4 hours. The reaction mixture was filter... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2c(c1)CCC1(CC[NH]CC1)O2 | Other | [Ni].C(C)(=O)O | null | null | CN1CCC2(CC1)CC(=O)c1cc([N+](=O)[O-])ccc1O2>[Ni].C(C)(=O)O>CN1CCC2(CC1)CC(=O)c1cc(N)ccc1O2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6c24fe13f1134a09b0896f1b0f8ba6a0 | CN1CCC2(CC1)CC(=O)c1cc(N)ccc1O2.CS(=O)(=O)Cl>>CN1CCC2(CC1)CC(=O)c1cc(NS(C)(=O)=O)ccc1O2 | NC=1C=CC2=C(C(CC3(CCN(CC3)C)O2)=O)C1.N1=CC=CC=C1.CS(=O)(=O)Cl>>CS(=O)(=O)NC=1C=CC2=C(C(CC3(CCN(CC3)C)O2)=O)C1 | [CH3:1][N:2]1[CH2:3][CH2:4][C:5]2([CH2:6][CH2:7]1)[CH2:8][C:9](=[O:10])[c:11]1[cH:12][c:13]([NH2:14])[cH:19][cH:20][c:21]1[O:22]2.Cl[S:15]([CH3:16])(=[O:17])=[O:18]>>[CH3:1][N:2]1[CH2:3][CH2:4][C:5]2([CH2:6][CH2:7]1)[CH2:8][C:9](=[O:10])[c:11]1[cH:12][c:13]([NH:14][S:15]([CH3:16])(=[O:17])=[O:18])[cH:19][cH:20][c:21]1[... | CN1CCC2(CC1)CC(=O)c1cc(N)ccc1O2.CS(=O)(=O)Cl | CN1CCC2(CC1)CC(=O)c1cc(NS(C)(=O)=O)ccc1O2 | null | null | C(Cl)Cl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C1CC2(CCNCC2)Oc2ccccc21 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 419 | [{"value": 50.0, "product": "CS(=O)(=O)NC=1C=CC2=C(C(CC3(CCN(CC3)C)O2)=O)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 419.0, "product": "CS(=O)(=O)NC=1C=CC2=C(C(CC3(CCN(CC3)C)O2)=O)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | 3,4-Dihydro-6-amino-1'-methyl-spiro[2H-1-benzopyran-2,4'-piperidin]-4-one (5.6 g, 0.0027 mol) was stirred in methylene chloride (50 ml) and pyridine (16 ml) at room temperature under a nitrogen atmosphere as methanesulfonyl chloride (2.7 ml, 0.035 mol) was added dropwise over several minutes. Some gum separated so addi... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccc2c(c1)CCC1(CC[NH]CC1)O2 | HCl | C(Cl)Cl | null | 16 | CN1CCC2(CC1)CC(=O)c1cc(N)ccc1O2.CS(=O)(=O)Cl>C(Cl)Cl>CN1CCC2(CC1)CC(=O)c1cc(NS(C)(=O)=O)ccc1O2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-442301e70e88430aba7d194beb8dd46d | COC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=C1CCN(C(=O)c2ccccc2)CC1>>O=P(c1ccccc1)(c1ccccc1)c1ccccc1 | C(C1=CC=CC=C1)(=O)N1CCC(CC1)=O.COC(=O)C=P(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3>>C1(=CC=CC=C1)P(C1=CC=CC=C1)(C1=CC=CC=C1)=O | COC(=O)C=[P:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)([c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1.O=C1CCN(C(c2ccccc2)=[O:1])CC1>>[O:1]=[P:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)([c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | COC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=C1CCN(C(=O)c2ccccc2)CC1 | O=P(c1ccccc1)(c1ccccc1)c1ccccc1 | null | null | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | b2358a42b6497fe7f75dece333a35a7d4e164eab9b78bc1466d704ff9aa32ca2 | ed6b3c2c64f30232911a85c601dabf2ab8cc0203e565c0f182ba92f19c27f5b0 | O=P(c1ccccc1)(c1ccccc1)c1ccccc1 | C-O-C(=O)-C=[P;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10].O=C1-C-C-N(-C(=[O;H0;D1;+0:11])-c2:c:c:c:c:c:2)-C-C-1>>[O;H0;D1;+0:11]=[P;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10] | 100 | [{"value": 100.0, "product": "C1(=CC=CC=C1)P(C1=CC=CC=C1)(C1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.9, "product": "C1(=CC=CC=C1)P(C1=CC=CC=C1)(C1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Under N2, a mixture of 1-benzoyl-4-piperidone (10.2 g, 0.05 mol), methyl (triphenylphosphoranylidene) acetate (25 g. 0.074 mol) in toluene (100 ml) was heated at reflux for 7 hours. After stirring at room temperature overnight, the solid was filtered off to yield 13.9 g (100%) of triphenylphosphine oxide. The mother li... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Tertiary amide | null | C1CCNCC1.c1ccccc1 | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C1(=CC=CC=C1)C | null | 8 | COC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=C1CCN(C(=O)c2ccccc2)CC1>C1(=CC=CC=C1)C>O=P(c1ccccc1)(c1ccccc1)c1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-16fafd1fac294152bba99cdec776ba37 | O=C1CC2(CCN(C(=O)c3ccccc3)CC2)Sc2ccccc21>>O=C1CC2(CCNCC2)Sc2ccccc21 | C(C1=CC=CC=C1)(=O)N1CCC2(CC1)SC1=C(C(C2)=O)C=CC=C1.Cl>>N1CCC2(CC1)SC1=C(C(C2)=O)C=CC=C1.Cl | O=C(c1ccccc1)[N:8]1[CH2:7][CH2:6][C:5]2([CH2:4][C:3](=[O:2])[c:17]3[c:12]([cH:13][cH:14][cH:15][cH:16]3)[S:11]2)[CH2:10][CH2:9]1>>[O:2]=[C:3]1[CH2:4][C:5]2([CH2:6][CH2:7][NH:8][CH2:9][CH2:10]2)[S:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]21 | O=C1CC2(CCN(C(=O)c3ccccc3)CC2)Sc2ccccc21 | O=C1CC2(CCNCC2)Sc2ccccc21 | null | null | C(C)O | Reduction | Hydrogenolysis of tertiary amines | d1ebdb22415b26584cd851599e266cb438c3b635953aed3fef73bc2af0a7785e | 62cf08a8ae6315067a063b5b3495125ccbdaff6b2340ce1d3e1c7b6cde962ae4 | O=C1CC2(CCNCC2)Sc2ccccc21 | O=C(-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5])-c1:c:c:c:c:c:1>>[C:5]-[C:4]-[NH;D2;+0:1]-[C:2]-[C:3] | 92 | [{"value": 92.0, "product": "N1CCC2(CC1)SC1=C(C(C2)=O)C=CC=C1.Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A solution of product from Step C (3.2 g, 0.0095 mol) in ethanol (50 ml) and 6 N HCl (50 ml) was heated at reflux. After 18 hours, the reaction was concentrated to dryness and the residue crystallized from ethanol to yield 2.9 g (92%) of product.
Conditions: See reaction.notes.procedure_details.
Workup: at reflux; the ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Secondary amine | c1ccccc1.c1ccc2c(c1)CCC1(CC[NH]CC1)S2 | c1ccc2c(c1)CCC1(CCNCC1)S2 | c1ccc2c(c1)CCC1(CCNCC1)S2 | HO- | C(C)O | null | 18 | O=C1CC2(CCN(C(=O)c3ccccc3)CC2)Sc2ccccc21>C(C)O>O=C1CC2(CCNCC2)Sc2ccccc21 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a4e3b11bcb904ad0ac7556437318ff19 | O=C1CCN(C(=O)c2ccccc2)CC1.Sc1ccccc1S>>O=C(c1ccccc1)N1CCC2(CC1)Sc1ccccc1S2 | [O-]S(=O)(=O)[O-].[Na+].[Na+].SC1=C(C=CC=C1)S.C(C1=CC=CC=C1)(=O)N1CCC(CC1)=O.Cl>>C(C1=CC=CC=C1)(=O)N1CCC2(CC1)SC1=C(S2)C=CC=C1 | O=[C:12]1[CH2:11][CH2:10][N:9]([C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][cH:8]2)[CH2:14][CH2:13]1.[SH:15][c:16]1[cH:17][cH:18][cH:19][cH:20][c:21]1[SH:22]>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[N:9]1[CH2:10][CH2:11][C:12]2([CH2:13][CH2:14]1)[S:15][c:16]1[cH:17][cH:18][cH:19][cH:20][c:21]1[S:22]2 | O=C1CCN(C(=O)c2ccccc2)CC1.Sc1ccccc1S | O=C(c1ccccc1)N1CCC2(CC1)Sc1ccccc1S2 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 0d3b18413d76e6e4f42668a3203734c6ab13511bbbeed5b7442e4129cf2c9c7f | 1d9d6ee9d77442dc1bde18cc35949be811ff28784f0810fab70dac59f3531b1b | O=C(c1ccccc1)N1CCC2(CC1)Sc1ccccc1S2 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[SH;D1;+0:7]-[c:8](:[c:9]):[c:10](-[SH;D1;+0:11]):[c:12]>>[c:9]:[c:8]1:[c:10](:[c:12])-[S;H0;D2;+0:11]-[C;H0;D4;+0:1]2(-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-2)-[S;H0;D2;+0:7]-1 | null | [] | null | null | 15 | HOUR | 500 mgs (3.52 mmol) of 1,2-dimercaptobenzene and 610 mgs (3.00 mmol) of N-benzoyl-4-piperidone were stirred in CH2Cl2 while anhydrous HCl gas was introduced Na2SO4 (2 grams) was added and the mixture stirred 15 hours. The mixture was diluted with CH2Cl2 filtered and washed with H2O, and 10% NaOH. The organics were drie... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Aromatic thiol.Aromatic thiol | Monosulfide.Monosulfide | C1CC[NH]CC1 | c1ccc2c(c1)SC1(CC[NH]CC1)S2 | c1ccccc1.c1ccc2c(c1)SC1(CC[NH]CC1)S2 | HO- | C(Cl)Cl | null | 15 | O=C1CCN(C(=O)c2ccccc2)CC1.Sc1ccccc1S>C(Cl)Cl>O=C(c1ccccc1)N1CCC2(CC1)Sc1ccccc1S2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-25efeb1467b543d6aa08ef96cec87305 | O=C(c1ccccc1)N1CCC2(CC1)Sc1ccc([N+](=O)[O-])cc1S2>>O=[N+]([O-])c1ccc2c(c1)SC1(CCNCC1)S2 | [N+](=O)([O-])C1=CC2=C(SC3(CCN(CC3)C(C3=CC=CC=C3)=O)S2)C=C1.[OH-].[Na+]>>[N+](=O)([O-])C1=CC2=C(SC3(CCNCC3)S2)C=C1 | O=C(c1ccccc1)[N:14]1[CH2:13][CH2:12][C:11]2([S:10][c:8]3[c:7]([cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:9]3)[S:17]2)[CH2:16][CH2:15]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[S:10][C:11]1([CH2:12][CH2:13][NH:14][CH2:15][CH2:16]1)[S:17]2 | O=C(c1ccccc1)N1CCC2(CC1)Sc1ccc([N+](=O)[O-])cc1S2 | O=[N+]([O-])c1ccc2c(c1)SC1(CCNCC1)S2 | null | null | O.C(C)O | Reduction | Hydrogenolysis of tertiary amines | 7a4d431ad2c3398f8b9b7205e7987bcd97785cc9e17c383f46bf55db87ca5662 | 62cf08a8ae6315067a063b5b3495125ccbdaff6b2340ce1d3e1c7b6cde962ae4 | c1ccc2c(c1)SC1(CCNCC1)S2 | O=C(-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5])-c1:c:c:c:c:c:1>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | null | [] | 70 | CELSIUS | null | null | 1.20 grams of the nitro dithioacetal from Step B in 46 mL of ethanol was treated with 18 mL of 40% aqueous NaOH and heated to 70° C. for 8 hours. The solution was diluted with water and extracted with CH2Cl2. The organics were combined, washed with water, saturated aqueous sodium carbonate, brine, dried (Na2SO4) and co... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Secondary amine | c1ccccc1.c1ccc2c(c1)SC1(CC[NH]CC1)S2 | c1ccc2c(c1)SC1(CCNCC1)S2 | c1ccc2c(c1)SC1(CCNCC1)S2 | HO- | O.C(C)O | 70 | null | O=C(c1ccccc1)N1CCC2(CC1)Sc1ccc([N+](=O)[O-])cc1S2>O.C(C)O>O=[N+]([O-])c1ccc2c(c1)SC1(CCNCC1)S2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-31cfffa70224479c92ad749173c818db | O=[N+]([O-])c1ccc(CCBr)cc1.c1ccc2c(c1)CSC1(CCNCC1)S2>>O=[N+]([O-])c1ccc(CC[SH]2c3ccccc3CSC23CCNCC3)cc1 | N1CCC2(CC1)SC1=C(CS2)C=CC=C1.C([O-])(O)=O.[Na+].[N+](=O)([O-])C1=CC=C(C=C1)CCBr>>[N+](=O)([O-])C1=CC=C(C=C1)CCS1C2=C(CSC13CCNCC3)C=CC=C2 | Br[CH2:9][CH2:8][c:7]1[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:26][cH:25]1.[S:10]1[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[CH2:17][S:18][C:19]12[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]2>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][CH2:9][SH:10]2[c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[CH2:17][S:18][C:19]23... | O=[N+]([O-])c1ccc(CCBr)cc1.c1ccc2c(c1)CSC1(CCNCC1)S2 | O=[N+]([O-])c1ccc(CC[SH]2c3ccccc3CSC23CCNCC3)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | a51cb16fe989549697d0fa051a0b9360266beb43e42e8c0dd6050e627f0ceccf | 1e6339d75322cc45c770cf1fc8fe9638f88f9eff36385ca6e4f82c8cab3a96f8 | c1ccc(CC[SH]2c3ccccc3CSC23CCNCC3)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[c:3].[C:4]-[C:5]1(-[C:6])-[#16:7]-[C:8]-[c:9]:[c:10](:[c:11])-[S;H0;D2;+0:12]-1>>[C:4]-[C:5]1(-[C:6])-[#16:7]-[C:8]-[c:9]:[c:10](:[c:11])-[SH;D3;+0:12]-1-[CH2;D2;+0:1]-[C:2]-[c:3] | null | [] | null | null | null | null | To 111 mgs (0.47 mmol) of dithioketal from Step A in 1 mL of methanol was added 157 mgs of sodium bicarbonate and 118 mg (0.54 mmol) of 2-(4-nitrophenyl)ethyl bromide. The reaction was refluxed for 6 hrs and then concentrated at reduced pressure. The residue was chromotographed (silica gel, 2.5% CH3OH/CH2Cl2) to give a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Monosulfide | null | c1ccc2c(c1)CSC1(CCNCC1)S2 | c1ccc2c(c1)CSC1(CCNCC1)[SH]2 | c1ccccc1.c1ccc2c(c1)CSC1(CCNCC1)[SH]2 | Br- | CO | null | null | O=[N+]([O-])c1ccc(CCBr)cc1.c1ccc2c(c1)CSC1(CCNCC1)S2>CO>O=[N+]([O-])c1ccc(CC[SH]2c3ccccc3CSC23CCNCC3)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-21f4820d09ec43eea37f1383b4e918e9 | O=C1CCNC(CCc2ccccn2)C1.O=[N+]([O-])c1ccc(S)c(CO)c1>>O=[N+]([O-])c1ccc2c(c1)COC1(CCN(CCc3ccccn3)CC1)S2 | SC1=C(CO)C=C(C=C1)[N+](=O)[O-].N1=C(C=CC=C1)CCC1NCCC(C1)=O>>[N+](=O)([O-])C=1C=CC2=C(COC3(CCN(CC3)CCC3=NC=CC=C3)S2)C1 | O=[C:12]1[CH2:13][CH2:14][NH:15][CH:24]([CH2:16][CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][n:23]2)[CH2:25]1.[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([SH:26])[c:8]([CH2:10][OH:11])[cH:9]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[CH2:10][O:11][C:12]1([CH2:13][CH2:14][N:15]([CH2:16][CH2:17][c:18]3[c... | O=C1CCNC(CCc2ccccn2)C1.O=[N+]([O-])c1ccc(S)c(CO)c1 | O=[N+]([O-])c1ccc2c(c1)COC1(CCN(CCc3ccccn3)CC1)S2 | null | null | C(Cl)(Cl)Cl | Functional Group Addition | OtherReaction | da0f6fb37cfbac9efa5ed795a217be23806f6e418aa769761a4132f58e2bd279 | 4118bbf535066e47681c317ea46590ac414fddca620ebd1df5edc56214153d73 | c1ccc(CCN2CCC3(CC2)OCc2ccccc2S3)nc1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-[CH;D3;+0:5](-[CH2;D2;+0:6]-[C:7]-[c:8]:[#7;a:9])-[C:10]-1.[OH;D1;+0:11]-[C:12]-[c:13]:[c:14](-[SH;D1;+0:15]):[c:16]>>[#7;a:9]:[c:8]-[C:7]-[CH2;D2;+0:6]-[N;H0;D3;+0:4]1-[C:3]-[C:2]-[C;H0;D4;+0:1]2(-[C:10]-[CH2;D2;+0:5]-1)-[O;H0;D2;+0:11]-[C:12]-[c:13]:[c:14](:[c:16])-[S;H0;D2;... | null | [] | 25 | CELSIUS | 2 | DAY | 2-Mercapto-5-nitrobenzyl alcohol (150 mg, 0.81 mmol) and 208 mg (0.80 mm) of N-[2-(2'-pyridyl ethyl]-4-piperidone was dissolved in 5 mL of CHCl3. HCl Gas was bubbled in to saturate the solution, the mixture stirred at 25° C. for 2 days, then diluted with water and the pH adjusted to 10.0 with 40% aqueous NaOH. Extracti... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary alcohol.Secondary amine.Aromatic thiol | Ether.Tertiary amine.Monosulfide | C1CCNCC1 | c1ccc2c(c1)COC1(CC[NH]CC1)S2 | c1ccc2c(c1)COC1(CC[NH]CC1)S2.c1ccncc1 | HO- | C(Cl)(Cl)Cl | 25 | 48 | O=C1CCNC(CCc2ccccn2)C1.O=[N+]([O-])c1ccc(S)c(CO)c1>C(Cl)(Cl)Cl>O=[N+]([O-])c1ccc2c(c1)COC1(CCN(CCc3ccccn3)CC1)S2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-09b8475db80c4c40aa60750fe9e33c66 | CS(=O)(=O)Cl.OCCc1ccc2nonc2c1>>CS(=O)(=O)OCCc1ccc2nonc2c1 | OCCC=1C=CC=2C(=NON2)C1.C(C)N(CC)CC.CS(=O)(=O)Cl>>CS(=O)(=O)OCCC=1C=CC=2C(=NON2)C1 | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]2[n:12][o:13][n:14][c:15]2[cH:16]1>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]2[n:12][o:13][n:14][c:15]2[cH:16]1 | CS(=O)(=O)Cl.OCCc1ccc2nonc2c1 | CS(=O)(=O)OCCc1ccc2nonc2c1 | null | null | ClCCl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1ccc2nonc2c1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 96.3 | [{"value": 96.0, "product": "CS(=O)(=O)OCCC=1C=CC=2C(=NON2)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.3, "product": "CS(=O)(=O)OCCC=1C=CC=2C(=NON2)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -30 | CELSIUS | 15 | MINUTE | 5-(2-Hydroxyethyl)benzofurazan (1.48 g, 9 mmol) was dissolved in dichloromethane (45 ml) and triethylamine (1.88 ml, 1.37 g, 13.5 mmol) was added. The mixture was cooled to -30° C. and methanesulfonyl chloride (0.84 ml, 1.24 g, 10.8 mmol) was added dropwise over 5 min. The mixture was stirred at -30° C. for 15 min. and... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | c1ccc2nonc2c1 | HCl | ClCCl | -30 | 0.25 | CS(=O)(=O)Cl.OCCc1ccc2nonc2c1>ClCCl>CS(=O)(=O)OCCc1ccc2nonc2c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3a716ce8682049ba850c6a9e0138388f | BrCCBr.Oc1ccc2nonc2c1>>BrCCOc1ccc2nonc2c1 | [OH-].[Na+].OC=1C=CC=2C(=NON2)C1.BrCCBr>>BrCCOC=1C=CC=2C(=NON2)C1 | Br[CH2:3][CH2:2][Br:1].[OH:4][c:5]1[cH:6][cH:7][c:8]2[n:9][o:10][n:11][c:12]2[cH:13]1>>[Br:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]2[n:9][o:10][n:11][c:12]2[cH:13]1 | BrCCBr.Oc1ccc2nonc2c1 | BrCCOc1ccc2nonc2c1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc2nonc2c1 | Br-[CH2;D2;+0:1]-[C:2]-[Br;D1;H0:3].[#7;a:4]:[c:5]:[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[#7;a:4]:[c:5]:[c:6]:[c:7](-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[C:2]-[Br;D1;H0:3]):[c:9] | 41 | [{"value": 41.0, "product": "BrCCOC=1C=CC=2C(=NON2)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.7, "product": "BrCCOC=1C=CC=2C(=NON2)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Sodium hydroxide (40 mg, 1 mmol) was added to a solution of 5-hydroxybenzofurazan (136 mg, 1 mmol) in ethanol (2 ml) and the mixture was stirred at room temperature for 30 min. 1,2-dibromoethane (0.26 ml, 0.56 g, 3 mmol) was added and the mixture was heated under reflux for 20 hr., cooled and the solvent was evaporated... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2nonc2c1 | HBr | C(C)O | null | 0.5 | BrCCBr.Oc1ccc2nonc2c1>C(C)O>BrCCOc1ccc2nonc2c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a044b14d95534fccb6fff56c706226ca | BrC(Br)(Br)Br.OCCc1ccc2nonc2c1>>BrCCc1ccc2nonc2c1 | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.OCCC=1C=CC=2C(=NON2)C1.C(Br)(Br)(Br)Br>>BrCCC=1C=CC=2C(=NON2)C1 | BrC(Br)(Br)[Br:1].O[CH2:2][CH2:3][c:4]1[cH:5][cH:6][c:7]2[n:8][o:9][n:10][c:11]2[cH:12]1>>[Br:1][CH2:2][CH2:3][c:4]1[cH:5][cH:6][c:7]2[n:8][o:9][n:10][c:11]2[cH:12]1 | BrC(Br)(Br)Br.OCCc1ccc2nonc2c1 | BrCCc1ccc2nonc2c1 | null | null | C(Cl)Cl | Functional Group Interconversion | Appel reaction | 752e1807cd47d8316010cc3f92eab16c5a89ffb844d9514fcae469ba993c78dd | 2c6b51fb1e17cb2c93d565e0423c75825df2c8e11c870e0c98b278f20ba9f3ad | c1ccc2nonc2c1 | Br-C(-Br)(-Br)-[Br;H0;D1;+0:1].O-[CH2;D2;+0:2]-[C:3]-[c:4]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[c:4] | 86,639,240 | [{"value": 86.0, "product": "BrCCC=1C=CC=2C(=NON2)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86639240.0, "product": "BrCCC=1C=CC=2C(=NON2)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | A solution of 5-(2-hydroxyethyl)benzofurazan (1.0 g, 6.1 nmol) and carbon tetrabromide (2.6 g, 7.9 nmol) in methylene chloride (10 ml) was cooled to 0° C. A solution of triphenyl phosphine (1.9 g, 7.3 nmol) in methylene chloride (10 ml) was added dropwise and the reaction was stirred for 5 min. Solvent evaporation and ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Primary alcohol | Primary halide | null | null | c1ccc2nonc2c1 | HBr | C(Cl)Cl | null | 0.083333 | BrC(Br)(Br)Br.OCCc1ccc2nonc2c1>C(Cl)Cl>BrCCc1ccc2nonc2c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6d12d6442a96446d8a9c31f411e01809 | BrCCc1ccc2nonc2c1.CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCNCC1)O2>>CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCN(CCc3ccc4nonc4c3)CC1)O2 | BrCCC=1C=CC=2C(=NON2)C1.Cl.CS(=O)(=O)NC=1C=CC2=C(C(CC3(CCNCC3)O2)=O)C1.C([O-])(O)=O.[Na+]>>Cl.N1=C2C(=NO1)C=C(C=C2)CCN2CCC1(CC2)OC2=C(C(C1)=O)C=C(C=C2)NS(=O)(=O)C | Br[CH2:19][CH2:20][c:21]1[cH:22][cH:23][c:24]2[n:25][o:26][n:27][c:28]2[cH:29]1.[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[C:12](=[O:13])[CH2:14][C:15]1([CH2:16][CH2:17][NH:18][CH2:30][CH2:31]1)[O:32]2>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[C:12](=[O:... | BrCCc1ccc2nonc2c1.CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCNCC1)O2 | CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCN(CCc3ccc4nonc4c3)CC1)O2 | null | null | C(C)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | fcc4a915ce374c4aab389e812dfb69762e7b96d1b9afab3cb3150e76db46ecf6 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1CC2(CCN(CCc3ccc4nonc4c3)CC2)Oc2ccccc21 | Br-[CH2;D2;+0:1]-[C:2]-[c:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]-[c:3])-[C:7]-[C:8] | 41.2 | [{"value": 41.0, "product": "Cl.N1=C2C(=NO1)C=C(C=C2)CCN2CCC1(CC2)OC2=C(C(C1)=O)C=C(C=C2)NS(=O)(=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.2, "product": "Cl.N1=C2C(=NO1)C=C(C=C2)CCN2CCC1(CC2)OC2=C(C(C1)=O)C=C(C=C2)NS(=O)(=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of 5-(2-bromoethyl)benzofurazan (0.39 g, 1.72 mmol), 3,4-dihydro-6-methanesulfonamidospiro[(2H)-1-benzopyran-2,4'-piperidine]-4-one hydrochloride (0.24 g, 0.69 mmol) and sodium bicarbonate (0.21 g, 2.55 mmol) in ethanol (13.2 ml) was heated at reflux temperature for 24 hr. Solvent evaporation and chromatog... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1ccc2c(c1)CCC1(CCNCC1)O2 | c1ccc2c(c1)CCC1(CC[NH]CC1)O2 | c1ccc2c(c1)CCC1(CC[NH]CC1)O2.c1ccc2nonc2c1 | HBr | C(C)O | null | null | BrCCc1ccc2nonc2c1.CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCNCC1)O2>C(C)O>CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCN(CCc3ccc4nonc4c3)CC1)O2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-947d6841260549d3b54d67fb4a7179a9 | CC(=O)Nc1ccc2c(c1)C(=O)CC1(CCNCC1)O2.O=[N+]([O-])c1ccc(CBr)cc1>>CC(=O)Nc1ccc2c(c1)C(=O)CC1(CCN(Cc3ccc([N+](=O)[O-])cc3)CC1)O2 | CO.C(Cl)(Cl)Cl.[N+](=O)([O-])C1=CC=C(CBr)C=C1.C(C)(=O)NC=1C=CC2=C(C(CC3(CCNCC3)O2)=O)C1.C(C)(C)N(CC)C(C)C>>C(C)(=O)NC=1C=CC2=C(C(CC3(CCN(CC3)CC3=CC=C(C=C3)[N+](=O)[O-])O2)=O)C1 | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[C:11](=[O:12])[CH2:13][C:14]1([CH2:15][CH2:16][NH:17][CH2:28][CH2:29]1)[O:30]2.Br[CH2:18][c:19]1[cH:20][cH:21][c:22]([N+:23](=[O:24])[O-:25])[cH:26][cH:27]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[C:11](=[O:12])[CH2:13][C:14]1(... | CC(=O)Nc1ccc2c(c1)C(=O)CC1(CCNCC1)O2.O=[N+]([O-])c1ccc(CBr)cc1 | CC(=O)Nc1ccc2c(c1)C(=O)CC1(CCN(Cc3ccc([N+](=O)[O-])cc3)CC1)O2 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | fcc4a915ce374c4aab389e812dfb69762e7b96d1b9afab3cb3150e76db46ecf6 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1CC2(CCN(Cc3ccccc3)CC2)Oc2ccccc21 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:8]-[C:9] | 59.6 | [{"value": 59.0, "product": "C(C)(=O)NC=1C=CC2=C(C(CC3(CCN(CC3)CC3=CC=C(C=C3)[N+](=O)[O-])O2)=O)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.6, "product": "C(C)(=O)NC=1C=CC2=C(C(CC3(CCN(CC3)CC3=CC=C(C=C3)[N+](=O)[O-])O2)=O)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-nitrobenzyl bromide (0.73 g, 3.4 mmol), 3,4-dihydro-6-acetamidospiro[(2H)-benzopyran-2,4'-piperidine]-4-one (0.94 g, 3.4 mmol) and diisopropylethylamine (0.61 ml, 3.5 mmol) in dimethylformamide (15 ml) was stirred at room temperature for 3 hr. The reaction mixture was then concentrated under reduced pre... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1ccc2c(c1)CCC1(CCNCC1)O2 | c1ccc2c(c1)CCC1(CC[NH]CC1)O2 | c1ccc2c(c1)CCC1(CC[NH]CC1)O2.c1ccccc1 | HBr | CN(C=O)C | null | null | CC(=O)Nc1ccc2c(c1)C(=O)CC1(CCNCC1)O2.O=[N+]([O-])c1ccc(CBr)cc1>CN(C=O)C>CC(=O)Nc1ccc2c(c1)C(=O)CC1(CCN(Cc3ccc([N+](=O)[O-])cc3)CC1)O2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-9b03d7f6f2964e45a150ed7ab18aa7c8 | CC(=O)Nc1ccc2c(c1)C(=O)CC1(CCN(Cc3ccc([N+](=O)[O-])cc3)CC1)O2>>CC(=O)Nc1ccc2c(c1)CCC1(CCN(Cc3ccc(N)cc3)CC1)O2 | C(C)(=O)NC=1C=CC2=C(C(CC3(CCN(CC3)CC3=CC=C(C=C3)[N+](=O)[O-])O2)=O)C1.C([O-])(O)=O.[Na+].[OH-].[Na+]>>C(C)(=O)NC=1C=CC2=C(CCC3(CCN(CC3)CC3=CC=C(C=C3)N)O2)C1 | O=[C:11]1[c:9]2[c:8]([cH:7][cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[cH:10]2)[O:27][C:13]2([CH2:12]1)[CH2:14][CH2:15][N:16]([CH2:17][c:18]1[cH:19][cH:20][c:21]([N+:22](=O)[O-])[cH:23][cH:24]1)[CH2:25][CH2:26]2>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[CH2:11][CH2:12][C:13]1([CH2:14][CH2:15][N:16]... | CC(=O)Nc1ccc2c(c1)C(=O)CC1(CCN(Cc3ccc([N+](=O)[O-])cc3)CC1)O2 | CC(=O)Nc1ccc2c(c1)CCC1(CCN(Cc3ccc(N)cc3)CC1)O2 | null | [Cl-].[Ti+3].[Cl-].[Cl-] | C(C)(=O)O | Reduction | OtherReaction | 8985ded34c0bf81299f9e2b3f91a3f7ce647b50d45f1547836f6a2340637be4a | 3c5c7ef2400d5d2a996d2d09cdefbec5aec3351f5fc8a14a05fd6968a0753f9f | c1ccc(CN2CCC3(CCc4ccccc4O3)CC2)cc1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#8:4]-[c:5]:[c:6]-1:[c:7].O=[N+;H0;D3:8](-[O-])-[c:9](:[c:10]):[c:11]>>[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11].[c:7]:[c:6]1:[c:5]-[#8:4]-[C:3]-[C:2]-[CH2;D2;+0:1]-1 | 82.1 | [{"value": 82.1, "product": "C(C)(=O)NC=1C=CC2=C(CCC3(CCN(CC3)CC3=CC=C(C=C3)N)O2)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 3,4-dihydro-6-acetamido-1'-(4-nitrobenzyl)spiro[(2H)-1-benzopyran-2,4'-piperidine]-4-one (0.58 g, 1.4 mmol) in acetic acid (6.4 ml) was added titanium (III) chloride (15% wt. in 20-30% wt. hydrochloric acid, 7 ml) dropwise. The reaction mixture was stirred at room temperature for 1 hr, cooled to 0° C. ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Nitro group | Primary amine | c1ccc2c(c1)CCC1(CC[NH]CC1)O2 | c1ccc2c(c1)CCC1(CC[NH]CC1)O2 | c1ccc2c(c1)CCC1(CC[NH]CC1)O2.c1ccccc1 | Other | [Cl-].[Ti+3].[Cl-].[Cl-].C(C)(=O)O | null | 1 | CC(=O)Nc1ccc2c(c1)C(=O)CC1(CCN(Cc3ccc([N+](=O)[O-])cc3)CC1)O2>[Cl-].[Ti+3].[Cl-].[Cl-].C(C)(=O)O>CC(=O)Nc1ccc2c(c1)CCC1(CCN(Cc3ccc(N)cc3)CC1)O2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-876d879d6ec744549debf35e4e67563d | CC(=O)Nc1ccc2c(c1)CCC1(CCN(Cc3ccc(N)cc3)CC1)O2>>Nc1ccc(CN2CCC3(CC2)CC(=O)c2cc(N)ccc2O3)cc1 | C(C)(=O)NC=1C=CC2=C(CCC3(CCN(CC3)CC3=CC=C(C=C3)N)O2)C1.Cl.[OH-].[Na+]>>NC=1C=CC2=C(C(CC3(CCN(CC3)CC3=CC=C(C=C3)N)O2)=O)C1 | CC(=[O:15])[NH:19][c:18]1[cH:17][c:16]2[c:22]([cH:21][cH:20]1)[O:23][C:10]1([CH2:9][CH2:8][N:7]([CH2:6][c:5]3[cH:4][cH:3][c:2]([NH2:1])[cH:25][cH:24]3)[CH2:12][CH2:11]1)[CH2:13][CH2:14]2>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][N:7]2[CH2:8][CH2:9][C:10]3([CH2:11][CH2:12]2)[CH2:13][C:14](=[O:15])[c:16]2[cH:17][c:18]([NH2... | CC(=O)Nc1ccc2c(c1)CCC1(CCN(Cc3ccc(N)cc3)CC1)O2 | Nc1ccc(CN2CCC3(CC2)CC(=O)c2cc(N)ccc2O3)cc1 | null | null | CO | Miscellaneous | OtherReaction | 01a04d52e078c4be97f885a20207f56a20ea0668290cc0e817af8c04fa5216b2 | 66f3156bebb43aa378bf50af0944e3de9570ac5cc9f6d0d57adc66597251de20 | O=C1CC2(CCN(Cc3ccccc3)CC2)Oc2ccccc21 | C-C(=[O;H0;D1;+0:1])-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5]:[c:6]1:[c:7]-[#8:8]-[C:9]-[C:10]-[CH2;D2;+0:11]-1>>[NH2;D1;+0:2]-[c:3](:[c:4]):[c:5]:[c:6]1:[c:7]-[#8:8]-[C:9]-[C:10]-[C;H0;D3;+0:11]-1=[O;H0;D1;+0:1] | 88 | [{"value": 88.0, "product": "NC=1C=CC2=C(C(CC3(CCN(CC3)CC3=CC=C(C=C3)N)O2)=O)C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3,4-dihydro-6-acetamido-1'-(4-aminobenzyl)spiro[(2H)-1-benzopyran-2,4'-piperidine] (136 mg, 0.36 mmol) and hydrochloric acid (6N solution, 13.6 ml) in methanol (13.6 ml) was heated at reflux temperature for 1 hr. The reaction mixture was cooled to 0° C. and basified with 20% sodium hydroxide solution. Ext... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Ketone.Primary amine | c1ccc2c(c1)CCC1(CC[NH]CC1)O2 | c1ccc2c(c1)CCC1(CC[NH]CC1)O2 | c1ccccc1.c1ccc2c(c1)CCC1(CC[NH]CC1)O2 | Other | CO | null | null | CC(=O)Nc1ccc2c(c1)CCC1(CCN(Cc3ccc(N)cc3)CC1)O2>CO>Nc1ccc(CN2CCC3(CC2)CC(=O)c2cc(N)ccc2O3)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3e41f9accd6644a589cc4ef9c8e97232 | COC(=O)c1ccc(-n2ccnc2)cc1>>OCc1ccc(-n2ccnc2)cc1 | COC(C1=CC=C(C=C1)N1C=NC=C1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].C1CCOC1>>OCC1=CC=C(C=C1)N1C=NC=C1 | CO[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6](-[n:7]2[cH:8][cH:9][n:10][cH:11]2)[cH:12][cH:13]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6](-[n:7]2[cH:8][cH:9][n:10][cH:11]2)[cH:12][cH:13]1 | COC(=O)c1ccc(-n2ccnc2)cc1 | OCc1ccc(-n2ccnc2)cc1 | null | null | C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(-n2ccnc2)cc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | 98 | [{"value": 98.0, "product": "OCC1=CC=C(C=C1)N1C=NC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | To a mixture of 4-(1H-imidazol-1-yl)benzoic acid methyl ester (prepared as described in U.S. Pat. No. 4,804,662) (1.5 g) in THF (25 ml) at -15° C. was added a solution of 1M LAH/THF (10.4) ml). The mixture was stirred for 1/2 hour and allowed to warm to room temperature. The reaction was quenched by addition of water (... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.c1c[nH]cn1 | Other | C1CCOC1 | null | 0.5 | COC(=O)c1ccc(-n2ccnc2)cc1>C1CCOC1>OCc1ccc(-n2ccnc2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-21549f1abd034e7fa819e5d32eb716a4 | CSCCN1CCC2(CC1)CC(=O)c1cc(NS(C)(=O)=O)ccc1O2>>CS(=O)(=O)CCN1CCC2(CC1)CC(=O)c1cc(NS(C)(=O)=O)ccc1O2 | CS(=O)(=O)NC=1C=CC2=C(C(CC3(CCN(CC3)CCSC)O2)=O)C1.OOS(=O)[O-].[K+].O.C(=O)(O)[O-].[Na+]>>CS(=O)(=O)NC=1C=CC2=C(C(CC3(CCN(CC3)CCS(=O)(=O)C)O2)=O)C1 | [CH3:1][S:2][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][C:10]2([CH2:11][CH2:12]1)[CH2:13][C:14](=[O:15])[c:16]1[cH:17][c:18]([NH:19][S:20]([CH3:21])(=[O:22])=[O:23])[cH:24][cH:25][c:26]1[O:27]2>>[CH3:1][S:2](=[O:3])(=[O:4])[CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][C:10]2([CH2:11][CH2:12]1)[CH2:13][C:14](=[O:15])[c:16]1[cH:17][c:18]([N... | CSCCN1CCC2(CC1)CC(=O)c1cc(NS(C)(=O)=O)ccc1O2 | CS(=O)(=O)CCN1CCC2(CC1)CC(=O)c1cc(NS(C)(=O)=O)ccc1O2 | null | null | CO | Oxidation | OtherReaction | 20dd6d48007b4fe7cd760226f21413eb5e71e6468db112596c2e7ea4858c8ac1 | 5cedc1bf0f43f21d78a249521ecfcec19fc5ac4895c41eed0e84f0c2618149fa | O=C1CC2(CCNCC2)Oc2ccccc21 | [C:1]-[C:2]-[S;H0;D2;+0:3]-[C;D1;H3:4]>>[C:1]-[C:2]-[S;H0;D4;+0:3](-[C;D1;H3:4])(=[O;D1;H0:5])=[O;D1;H0:6] | 44.6 | [{"value": 44.6, "product": "CS(=O)(=O)NC=1C=CC2=C(C(CC3(CCN(CC3)CCS(=O)(=O)C)O2)=O)C1", "details": "PERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 2 | HOUR | A solution of 6-methanesulfonamido-3,4-dihydro-1'-(2-methylthioethyl)spiro[(2H)-1-benzopyran-2,4'-piperidine]-4-one (0.335 g, 0.871 mmol) in 15 mL of methanol was treated dropwise with a solution of Oxone® (0.803 g, 1.31 mmol) in 15 mL of water. The resulting mixture was stirred at 25° C. for 2 hours. The reaction mixt... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfone | null | null | c1ccc2c(c1)CCC1(CC[NH]CC1)O2 | null | CO | 25 | 2 | CSCCN1CCC2(CC1)CC(=O)c1cc(NS(C)(=O)=O)ccc1O2>CO>CS(=O)(=O)CCN1CCC2(CC1)CC(=O)c1cc(NS(C)(=O)=O)ccc1O2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-525f17d072ad44f5b9d585107ba4daf9 | CC(=O)Cl.CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCN(CCc3ccc(N)cc3)CC1)O2>>CC(=O)Nc1ccc(CCN2CCC3(CC2)CC(=O)c2cc(NS(C)(=O)=O)ccc2O3)cc1 | CS(=O)(=O)NC=1C=CC2=C(C(CC3(CCN(CC3)CCC3=CC=C(C=C3)N)O2)=O)C1.N1=CC=CC=C1.C(C)(=O)Cl>>CS(=O)(=O)NC=1C=CC2=C(C(CC3(CCN(CC3)CCC3=CC=C(C=C3)NC(C)=O)O2)=O)C1 | Cl[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][c:8]([CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][C:14]3([CH2:15][CH2:16]2)[CH2:17][C:18](=[O:19])[c:20]2[cH:21][c:22]([NH:23][S:24]([CH3:25])(=[O:26])=[O:27])[cH:28][cH:29][c:30]2[O:31]3)[cH:32][cH:33]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([CH2:9][CH2:10][N:11]2... | CC(=O)Cl.CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCN(CCc3ccc(N)cc3)CC1)O2 | CC(=O)Nc1ccc(CCN2CCC3(CC2)CC(=O)c2cc(NS(C)(=O)=O)ccc2O3)cc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C1CC2(CCN(CCc3ccccc3)CC2)Oc2ccccc21 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 18 | [{"value": 18.0, "product": "CS(=O)(=O)NC=1C=CC2=C(C(CC3(CCN(CC3)CCC3=CC=C(C=C3)NC(C)=O)O2)=O)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 17.7, "product": "CS(=O)(=O)NC=1C=CC2=C(C(CC3(CCN(CC3)CCC3=CC=C(C=C3)NC(C)=O)O2)=O)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | A suspension of 6-methanesulfonamido-3,4-dihydro-1'-(2-(4-aminophenyl)ethyl)-spiro[(2H)-1-benzopyran-2,4'-piperidine]-4-one (0.50 g, 1.2 mmol), and pyridine (0.09 mL, 1.2 mmol) in 25 mL of methylene chloride was cooled in an ice bath and treated dropwise with acetyl chloride (0.09 mL, 1.2 mmol). The mixture was stirred... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)CCC1(CC[NH]CC1)O2 | HCl | C(Cl)Cl | 0 | 2 | CC(=O)Cl.CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCN(CCc3ccc(N)cc3)CC1)O2>C(Cl)Cl>CC(=O)Nc1ccc(CCN2CCC3(CC2)CC(=O)c2cc(NS(C)(=O)=O)ccc2O3)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ef0eae7f82d04b7abdea25f31eba98a9 | CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCNCC1)O2.ClCCc1ccc(Cl)nc1>>CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCN(CCc3ccc(Cl)nc3)CC1)O2 | ClC1=CC=C(C=N1)CC(=O)O.Cl.CS(=O)(=O)NC=1C=CC2=C(C(CC3(CCNCC3)O2)=O)C1.Cl.ClC1=NC=C(C=C1)CCCl.S(=O)(Cl)Cl.Cl.ClC1=NC=C(C=C1)CCCl>>CS(=O)(=O)NC=1C=CC2=C(C(CC3(CCN(CC3)CCC=3C=CC(=NC3)Cl)O2)=O)C1 | [CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[C:12](=[O:13])[CH2:14][C:15]1([CH2:16][CH2:17][NH:18][CH2:28][CH2:29]1)[O:30]2.Cl[CH2:19][CH2:20][c:21]1[cH:22][cH:23][c:24]([Cl:25])[n:26][cH:27]1>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[C:12](=[O:13])[CH2:14... | CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCNCC1)O2.ClCCc1ccc(Cl)nc1 | CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCN(CCc3ccc(Cl)nc3)CC1)O2 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | fcc4a915ce374c4aab389e812dfb69762e7b96d1b9afab3cb3150e76db46ecf6 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1CC2(CCN(CCc3cccnc3)CC2)Oc2ccccc21 | Cl-[CH2;D2;+0:1]-[C:2]-[c:3]:[c:4]:[#7;a:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[#7;a:5]:[c:4]:[c:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8](-[C:7]-[C:6])-[C:9]-[C:10] | null | [] | null | null | null | null | The title compound was prepared from 3,4-dihydro-6-methanesulfonamidospiro[(2H)-1-benzopyran-2,4'-piperidine]-4-one hydrochloride and 2-chloro-5-chloroethylpyridine hydrochloride by a procedure analogous to that described in Example 92, Step B. [The 2-chloro-5-chloroethylpyridine hydrochloride used in this reaction was... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1ccc2c(c1)CCC1(CCNCC1)O2 | c1ccc2c(c1)CCC1(CC[NH]CC1)O2 | c1ccc2c(c1)CCC1(CC[NH]CC1)O2.c1ccncc1 | HCl | null | null | null | CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCNCC1)O2.ClCCc1ccc(Cl)nc1>>CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCN(CCc3ccc(Cl)nc3)CC1)O2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e8fb55e1737e4827b7e769d1e042ed5c | BrCCBr.C=C(C)n1c(=O)[nH]c2ccccc21>>C=C(C)n1c(=O)n(CCBr)c2ccccc21 | C(=C)(C)N1C(NC2=C1C=CC=C2)=O.BrCCBr.[H-].[Na+]>>C(=C)(C)N1C(N(C2=C1C=CC=C2)CCBr)=O | Br[CH2:8][CH2:9][Br:10].[CH2:1]=[C:2]([CH3:3])[n:4]1[c:5](=[O:6])[nH:7][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]12>>[CH2:1]=[C:2]([CH3:3])[n:4]1[c:5](=[O:6])[n:7]([CH2:8][CH2:9][Br:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]12 | BrCCBr.C=C(C)n1c(=O)[nH]c2ccccc21 | C=C(C)n1c(=O)n(CCBr)c2ccccc21 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 798c3cd6443cfe7f029ed03c4760cf76103b5f272c5de707760a27469f565eca | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c2ccccc2[nH]1 | Br-[CH2;D2;+0:1]-[C:2]-[Br;D1;H0:3].[C;D1;H2:4]=[C:5]-[#7;a:6]1:[c:7](:[c:8]):[c:9](:[c:10]):[nH;D2;+0:11]:[c:12]:1=[O;D1;H0:13]>>[Br;D1;H0:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:11]1:[c:9](:[c:10]):[c:7](:[c:8]):[#7;a:6](-[C:5]=[C;D1;H2:4]):[c:12]:1=[O;D1;H0:13] | null | [] | null | null | null | null | 1-Isopropenylbenzimidazolone (J. Davol, J. Chem. Soc., 1960, 308) was alkylated with 1,2-dibromoethane using sodium hydride in DMF. The product was purified by chromatography and crystallization from cyclohexane to give 1-isopropenyl-3-(2-bromoethyl)benzimidazolone.
Conditions: See reaction.notes.procedure_details.
Wor... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]cnc2c1 | c1nc2ccccc2[nH]1 | c1nc2ccccc2[nH]1 | HBr | CN(C)C=O | null | null | BrCCBr.C=C(C)n1c(=O)[nH]c2ccccc21>CN(C)C=O>C=C(C)n1c(=O)n(CCBr)c2ccccc21 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-318a0d649152403aa70213f1e775d186 | N#Cc1ccc(CCO)cc1>>NCc1ccc(CCO)cc1 | C(#N)C1=CC=C(CCO)C=C1.Cl>>OCCC1=CC=C(CN)C=C1 | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][OH:9])[cH:10][cH:11]1>>[NH2:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][OH:9])[cH:10][cH:11]1 | N#Cc1ccc(CCO)cc1 | NCc1ccc(CCO)cc1 | null | [Pd] | C(C)O | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1ccccc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[NH2;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | A solution of 0.74 g (0.005 mol) of p-cyanophenethyl alcohol in 50 ml of ethanol containing 10 ml of concentrated hydrochloric acid was hydrogenated at 30 psi using 0.1 g 5% Pd/C for 72 hours. The catalyst was removed by filtration and the solvent was removed under reduced pressure.
Conditions: See reaction.notes.proce... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccccc1 | null | [Pd].C(C)O | null | null | N#Cc1ccc(CCO)cc1>[Pd].C(C)O>NCc1ccc(CCO)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-9c1c7be5dc37482b9254a181f9161fc1 | CN.CSC(=NCc1ccc(CCO)cc1)NC#N>>CNC(=NCc1ccc(CCO)cc1)NC#N | C(#N)NC(SC)=NCC1=CC=C(C=C1)CCO.CN>>C(#N)NC(=NCC1=CC=C(C=C1)CCO)NC | [CH3:1][NH2:2].CS[C:3](=[N:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([CH2:10][CH2:11][OH:12])[cH:13][cH:14]1)[NH:15][C:16]#[N:17]>>[CH3:1][NH:2][C:3](=[N:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([CH2:10][CH2:11][OH:12])[cH:13][cH:14]1)[NH:15][C:16]#[N:17] | CN.CSC(=NCc1ccc(CCO)cc1)NC#N | CNC(=NCc1ccc(CCO)cc1)NC#N | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 2ebe33ae3b7bb48bd968f9b830d6d3b488b85670dea18c3fe37a1f418e787d67 | 88e0224d19b2dce8f9987d52554afb32090d36ff7ee19e89dc5bf66d30974ec4 | c1ccccc1 | C-S-[C;H0;D3;+0:1](-[#7:2]-[C:3]#[N;D1;H0:4])=[#7:5]-[C:6].[C;D1;H3:7]-[NH2;D1;+0:8]>>[C:6]-[#7:5]=[C;H0;D3;+0:1](-[#7:2]-[C:3]#[N;D1;H0:4])-[NH;D2;+0:8]-[C;D1;H3:7] | null | [] | null | null | null | null | A solution of 0.42 g (0.00168 mol) of N-cyano-N'-[4-(2-hydroxyethyl)benzyl]-S-methylisothiourea in 50 ml of methanol and 10 g of methylamine was stirred at room temperature overnight. Evaporation of the solvent gave the title compound.
Conditions: See reaction.notes.procedure_details.
Workup: Evaporation of the solvent | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide | Secondary amine | null | null | c1ccccc1 | Other | CO | null | null | CN.CSC(=NCc1ccc(CCO)cc1)NC#N>CO>CNC(=NCc1ccc(CCO)cc1)NC#N |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-5316fdb95ac1472fad8e43ff4c6050cf | COc1ccc2c(c1)C(=O)CC1(CCNCC1)O2.Cn1c(Cl)cc(=O)n(C)c1=O>>COc1ccc2c(c1)C(=O)CC1(CCN(c3cc(=O)n(C)c(=O)n3C)CC1)O2 | Cl.COC=1C=CC2=C(C(CC3(CCNCC3)O2)=O)C1.ClC1=CC(N(C(N1C)=O)C)=O.C([O-])(O)=O.[Na+]>>COC=1C=CC2=C(C(CC3(CCN(CC3)C3=CC(N(C(N3C)=O)C)=O)O2)=O)C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9](=[O:10])[CH2:11][C:12]1([CH2:13][CH2:14][NH:15][CH2:26][CH2:27]1)[O:28]2.Cl[c:16]1[cH:17][c:18](=[O:19])[n:20]([CH3:21])[c:22](=[O:23])[n:24]1[CH3:25]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9](=[O:10])[CH2:11][C:12]1([CH2:13][CH2:14][N:15]([c:16]3[c... | COc1ccc2c(c1)C(=O)CC1(CCNCC1)O2.Cn1c(Cl)cc(=O)n(C)c1=O | COc1ccc2c(c1)C(=O)CC1(CCN(c3cc(=O)n(C)c(=O)n3C)CC1)O2 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | bc34618442e5983c32b958a7ba036a5956ffdb399bcfda57c8d7a1117867fc26 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=C1CC2(CCN(c3cc(=O)[nH]c(=O)[nH]3)CC2)Oc2ccccc21 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3](=[O;D1;H0:4]):[#7;a:5](-[C;D1;H3:6]):[c:7](=[O;D1;H0:8]):[#7;a:9]:1-[C;D1;H3:10].[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]>>[C:11]-[C:12]-[N;H0;D3;+0:13](-[c;H0;D3;+0:1]1:[c:2]:[c:3](=[O;D1;H0:4]):[#7;a:5](-[C;D1;H3:6]):[c:7](=[O;D1;H0:8]):[#7;a:9]:1-[C;D1;H3:10])-[C:14]-[C:15] | 61 | [{"value": 61.0, "product": "COC=1C=CC2=C(C(CC3(CCN(CC3)C3=CC(N(C(N3C)=O)C)=O)O2)=O)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.0, "product": "COC=1C=CC2=C(C(CC3(CCN(CC3)C3=CC(N(C(N3C)=O)C)=O)O2)=O)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3,4-dihydro-6-methoxyspiro[(2H)-1-benzopyran-2,4'-piperidin]-4-one hydrochloride (0.568 g, 2 mmol), 6-chloro-1,3-dimethylpyrimidine-2,4-(1H,3H)-dione (0.349 g, 2 mmol) and sodium bicarbonate (0.42 g, 5 mmol) in acetonitrile was heated at reflux for 42 hours. After cooling, the reaction mixture was concent... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2c(c1)CCC1(CCNCC1)O2.c1cncnc1 | c1ccc2c(c1)CCC1(CC[NH]CC1)O2.c1cncnc1 | c1ccc2c(c1)CCC1(CC[NH]CC1)O2.c1cncnc1 | HCl | C(C)#N | null | null | COc1ccc2c(c1)C(=O)CC1(CCNCC1)O2.Cn1c(Cl)cc(=O)n(C)c1=O>C(C)#N>COc1ccc2c(c1)C(=O)CC1(CCN(c3cc(=O)n(C)c(=O)n3C)CC1)O2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-88c9f74d06f8450f9794988fded824ed | COc1ccc2c(c1)C(=O)CC1(CCNCC1)O2.Cn1c(Cl)cc(=O)n(C)c1=O.NCCCl>>COc1ccc2c(c1)C(=O)CC1(CCN(NCCc3cc(=O)n(C)c(=O)n3C)CC1)O2 | COC=1C=CC2=C(C(CC3(CCNCC3)O2)=O)C1.C([O-])(O)=O.[Na+].ClC1=CC(N(C(N1C)=O)C)=O.C([O-])(O)=O.[Na+].Cl.ClCCN>>COC=1C=CC2=C(C(CC3(CCN(CC3)NCCC3=CC(N(C(N3C)=O)C)=O)O2)=O)C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9](=[O:10])[CH2:11][C:12]1([CH2:13][CH2:14][NH:15][CH2:29][CH2:30]1)[O:31]2.Cl[c:19]1[cH:20][c:21](=[O:22])[n:23]([CH3:24])[c:25](=[O:26])[n:27]1[CH3:28].Cl[CH2:18][CH2:17][NH2:16]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9](=[O:10])[CH2:11][C:12]1([CH2:... | COc1ccc2c(c1)C(=O)CC1(CCNCC1)O2.Cn1c(Cl)cc(=O)n(C)c1=O.NCCCl | COc1ccc2c(c1)C(=O)CC1(CCN(NCCc3cc(=O)n(C)c(=O)n3C)CC1)O2 | null | null | C(C)#N | C-C Coupling | OtherReaction | e5d14b9a1390e93fd473cc0623468fae4ee720b2637de5e9ac381352607b0271 | 18003c40afa0ae7056d4af614852fee10a5b33bbd4fc564f4ecabd7cb824e747 | O=C1CC2(CCN(NCCc3cc(=O)[nH]c(=O)[nH]3)CC2)Oc2ccccc21 | Cl-[CH2;D2;+0:1]-[C:2]-[NH2;D1;+0:3].Cl-[c;H0;D3;+0:4]1:[c:5]:[c:6](=[O;D1;H0:7]):[#7;a:8](-[C;D1;H3:9]):[c:10](=[O;D1;H0:11]):[#7;a:12]:1-[C;D1;H3:13].[C:14]-[C:15]-[NH;D2;+0:16]-[C:17]-[C:18]>>[C:14]-[C:15]-[N;H0;D3;+0:16](-[NH;D2;+0:3]-[C:2]-[CH2;D2;+0:1]-[c;H0;D3;+0:4]1:[c:5]:[c:6](=[O;D1;H0:7]):[#7;a:8](-[C;D1;H3:... | 10.5 | [{"value": 10.5, "product": "COC=1C=CC2=C(C(CC3(CCN(CC3)NCCC3=CC(N(C(N3C)=O)C)=O)O2)=O)C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 10.5, "product": "COC=1C=CC2=C(C(CC3(CCN(CC3)NCCC3=CC(N(C(N3C)=O)C)=O)O2)=O)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 28 | HOUR | A suspension of 3,4-dihydro-6-methoxyspiro[(2H)-1-benzopyran-2,4'-piperidin]-4-one (0.284 g, 1 mmol) and sodium bicarbonate (0.42 g, 5 mmol) in acetonitrile was heated at reflux for 1 hour, 2-chloro ethylamine hydrochloride (0.116 g, 1 mmol) was added the solution was heated at reflux for 17 hours, 6-chloro-1,3-dimethy... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary halide.Primary amine.Secondary amine | Hydrazine | c1ccc2c(c1)CCC1(CCNCC1)O2.c1cncnc1 | c1ccc2c(c1)CCC1(CC[NH]CC1)O2.c1cncnc1 | c1ccc2c(c1)CCC1(CC[NH]CC1)O2.c1cncnc1 | HCl | C(C)#N | null | 28 | COc1ccc2c(c1)C(=O)CC1(CCNCC1)O2.Cn1c(Cl)cc(=O)n(C)c1=O.NCCCl>C(C)#N>COc1ccc2c(c1)C(=O)CC1(CCN(NCCc3cc(=O)n(C)c(=O)n3C)CC1)O2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-7ff27640a0d54d469b56503d444125ed | CC(=O)Nc1ccc(CCN2CCC3(CC2)OCCO3)cc1[N+](=O)[O-]>>Nc1ccc(CCN2CCC(=O)CC2)cc1[N+](=O)[O-] | C(C)(=O)NC1=C(C=C(C=C1)CCN1CCC2(OCCO2)CC1)[N+](=O)[O-].C([O-])([O-])=O.[Na+].[Na+].[OH-].[Na+]>>NC1=C(C=C(C=C1)CCN1CCC(CC1)=O)[N+](=O)[O-] | CC(=O)[NH:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][C:11]3(OCC[O:12]3)[CH2:13][CH2:14]2)[cH:15][c:16]1[N+:17](=[O:18])[O-:19]>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][C:11](=[O:12])[CH2:13][CH2:14]2)[cH:15][c:16]1[N+:17](=[O:18])[O-:19] | CC(=O)Nc1ccc(CCN2CCC3(CC2)OCCO3)cc1[N+](=O)[O-] | Nc1ccc(CCN2CCC(=O)CC2)cc1[N+](=O)[O-] | null | null | Cl.O | Miscellaneous | OtherReaction | 176e3c936f8b0228a9f0ca46976463d0d009d1179afb166ac4c2da9f24278672 | b81fbae8c1fcf1836374d8300cfb4cb18a278d33ac9b4c50c799b24d221cbea0 | O=C1CCN(CCc2ccccc2)CC1 | C-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4].C1-C-[O;H0;D2;+0:5]-[C;H0;D4;+0:6]2(-O-1)-[C:7]-[C:8]-[#7:9]-[C:10]-[C:11]-2>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[O;H0;D1;+0:5]=[C;H0;D3;+0:6]1-[C:7]-[C:8]-[#7:9]-[C:10]-[C:11]-1 | 100 | [{"value": 100.0, "product": "NC1=C(C=C(C=C1)CCN1CCC(CC1)=O)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of 5.24 g (15.0 mmol) of 1-(8-[2-(4-acetamido-3-nitrophenyl)ethyl]-1,4-dioxa-8-azaspiro[4.5]decane in 30 mL 2N hydrochloric acid was heated at reflux for 1.5 hours. The cooled mixture was basified (pH 9-10) with saturated sodium carbonate solution and 10N sodium hydroxide, diluted with 100 ml water, and ex... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Secondary amide | Ketone.Primary amine | C1CC2(CC[NH]1)OCCO2 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1 | HO- | Cl.O | null | null | CC(=O)Nc1ccc(CCN2CCC3(CC2)OCCO3)cc1[N+](=O)[O-]>Cl.O>Nc1ccc(CCN2CCC(=O)CC2)cc1[N+](=O)[O-] |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-15723b5096154a8997b8fde29ebb3e38 | N#Cc1ccc(CCO)nc1>>C=Cc1ccc(C#N)cn1 | C(#N)C=1C=CC(=NC1)CCO.O.C1(=CC=C(C=C1)S(=O)(=O)O)C.C([O-])(O)=O.[Na+]>>C(#N)C=1C=CC(=NC1)C=C | O[CH2:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([C:7]#[N:8])[cH:9][n:10]1>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([C:7]#[N:8])[cH:9][n:10]1 | N#Cc1ccc(CCO)nc1 | C=Cc1ccc(C#N)cn1 | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | 567ff9e729a2d16a3e456243eaa6fea906fc7f4a844968338133cf6b5d71906c | 962c102d7e14de3254b057440327853861d9d966484d1838cbc59a673a23337d | c1ccncc1 | O-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[#7;a:5]:[c:6]>>[CH2;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[#7;a:5]:[c:6] | 36.3 | [{"value": 36.0, "product": "C(#N)C=1C=CC(=NC1)C=C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.3, "product": "C(#N)C=1C=CC(=NC1)C=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 0.163 g (1.1 mmol) 5-cyano-2-(2-hydroxyethyl)pyridine and 0.029 g (0.15 mmol) p-toluenesulfonic acid hydrate in 10 mL toluene was heated to reflux for five hours in a flask equipped with a Dean-Stark trap. The cooled mixture was neutralized with 5 mL saturated sodium bicarbonate solution and extracted with... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Vinyl | null | null | c1ccncc1 | HO- | C1(=CC=CC=C1)C | null | null | N#Cc1ccc(CCO)nc1>C1(=CC=CC=C1)C>C=Cc1ccc(C#N)cn1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-1b3fc702fdbd4fa5893859a012326d24 | CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCNCC1)O2.CS(=O)(=O)OCCc1ccc2ncsc2c1>>CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCN(CCc3ccc4ncsc4c3)CC1)O2 | Cl.CS(=O)(=O)NC=1C=CC2=C(C(CC3(CCNCC3)O2)=O)C1.C([O-])(O)=O.[Na+].CS(=O)(=O)OCCC1=CC2=C(N=CS2)C=C1.[I-].[K+]>>Cl.S1C=NC2=C1C=C(C=C2)CCN2CCC1(CC2)OC2=C(C(C1)=O)C=C(C=C2)NS(=O)(=O)C | [CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[C:12](=[O:13])[CH2:14][C:15]1([CH2:16][CH2:17][NH:18][CH2:30][CH2:31]1)[O:32]2.CS(=O)(=O)O[CH2:19][CH2:20][c:21]1[cH:22][cH:23][c:24]2[n:25][cH:26][s:27][c:28]2[cH:29]1>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[... | CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCNCC1)O2.CS(=O)(=O)OCCc1ccc2ncsc2c1 | CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCN(CCc3ccc4ncsc4c3)CC1)O2 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Alkylation of amines | cf82d2a38f125ca8c9949e8e8f3aeaad2fce343be85d05de0088847feeb0d203 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=C1CC2(CCN(CCc3ccc4ncsc4c3)CC2)Oc2ccccc21 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[c:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]-[c:3])-[C:7]-[C:8] | 48 | [{"value": 48.0, "product": "Cl.S1C=NC2=C1C=C(C=C2)CCN2CCC1(CC2)OC2=C(C(C1)=O)C=C(C=C2)NS(=O)(=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.8, "product": "Cl.S1C=NC2=C1C=C(C=C2)CCN2CCC1(CC2)OC2=C(C(C1)=O)C=C(C=C2)NS(=O)(=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a manner similar to that described in Example 92, Step B a mixture of 3,4-dihydro-6-methanesulfonamido-spiro[(2H)-1-benzopyran-2,4'-piperidine]-4-one hydrochloride (0.146 g, 0.42 mmol), sodium bicarbonate (0.143 g, 1.70 mmol), 6-benzothiazolylethyl methanesulfonate (0.108 g, 0.42 mmol), potassium iodide (0.070 g, 0.... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | c1ccc2c(c1)CCC1(CCNCC1)O2 | c1ccc2c(c1)CCC1(CC[NH]CC1)O2 | c1ccc2c(c1)CCC1(CC[NH]CC1)O2.c1ccc2scnc2c1 | MsOH.HO- | C(C)#N | null | null | CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCNCC1)O2.CS(=O)(=O)OCCc1ccc2ncsc2c1>C(C)#N>CS(=O)(=O)Nc1ccc2c(c1)C(=O)CC1(CCN(CCc3ccc4ncsc4c3)CC1)O2 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-10f0b3d1151e4129a36d8f920eff1d36 | CSCc1ccc(O)c(C(C)=O)c1.[O-][I+3]([O-])([O-])[O-]>>CC(=O)c1cc(CS(C)=O)ccc1O | OC1=C(C=C(C=C1)CSC)C(C)=O.I(=O)(=O)(=O)[O-].[Na+]>>OC1=C(C=C(C=C1)CS(=O)C)C(C)=O | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([CH2:7][S:8][CH3:9])[cH:11][cH:12][c:13]1[OH:14].[O-][I+3]([O-])([O-])[O-:10]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([CH2:7][S:8]([CH3:9])=[O:10])[cH:11][cH:12][c:13]1[OH:14] | CSCc1ccc(O)c(C(C)=O)c1.[O-][I+3]([O-])([O-])[O-] | CC(=O)c1cc(CS(C)=O)ccc1O | null | null | O.CO | Oxidation | OtherReaction | 9edfaf6d72a81452ea8e3a1cdcb10a58409fff36608e97019e7273998b3d5373 | f5f6bb6ca76a2267cd589767b4d67e7a17ab1ac383eeb6143dcd5d92e00e1b6a | c1ccccc1 | [C;D1;H3:1]-[S;H0;D2;+0:2]-[C:3]-[c:4].[O-;H0;D1:5]-[I+3](-[O-])(-[O-])-[O-]>>[C;D1;H3:1]-[S;H0;D3;+0:2](=[O;H0;D1;+0:5])-[C:3]-[c:4] | 60 | [{"value": 60.0, "product": "OC1=C(C=C(C=C1)CS(=O)C)C(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.5, "product": "OC1=C(C=C(C=C1)CS(=O)C)C(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 2'-hydroxy-5'-(methylthiomethyl)acetophenone (2.20 g, 11.0 mmol) in 70 mL MeOH cooled in an ice bath was added a solution of sodium metaperiodate (2.49 g, 12.1 mmol) in 115 mL water. The resulting cloudy mixture was stirred two hours with cooling then partially concentrated in vacuo to remove methanol.... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfoxide | null | null | c1ccccc1 | I- | O.CO | null | 2 | CSCc1ccc(O)c(C(C)=O)c1.[O-][I+3]([O-])([O-])[O-]>O.CO>CC(=O)c1cc(CS(C)=O)ccc1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-88eceac4d7b14e2ba62b61092830aadb | CSCc1ccc(O)c(C(C)=O)c1>>CC(=O)c1cc(CS(C)(=O)=O)ccc1O | OC1=C(C=C(C=C1)CSC)C(C)=O.CO.OOS(=O)[O-].[K+]>>OC1=C(C=C(C=C1)CS(=O)(=O)C)C(C)=O | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([CH2:7][S:8][CH3:9])[cH:12][cH:13][c:14]1[OH:15]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([CH2:7][S:8]([CH3:9])(=[O:10])=[O:11])[cH:12][cH:13][c:14]1[OH:15] | CSCc1ccc(O)c(C(C)=O)c1 | CC(=O)c1cc(CS(C)(=O)=O)ccc1O | null | null | O | Oxidation | OtherReaction | 20dd6d48007b4fe7cd760226f21413eb5e71e6468db112596c2e7ea4858c8ac1 | 5cedc1bf0f43f21d78a249521ecfcec19fc5ac4895c41eed0e84f0c2618149fa | c1ccccc1 | [C;D1;H3:1]-[S;H0;D2;+0:2]-[C:3]-[c:4]>>[C;D1;H3:1]-[S;H0;D4;+0:2](=[O;D1;H0:5])(=[O;D1;H0:6])-[C:3]-[c:4] | null | [] | null | null | 2 | HOUR | To a solution of 2'-hydroxy-5'-(methylthiomethyl)acetophenone (2.20 g, 11.0 mmol) in 88 mL methanol cooled in an ice bath was added a solution of OXONE (commercial potassium peroxymonosulfate mixture, Aldrich Chemical Co.)(20.28 g, 33.0 mmol) in 88 mL water. The mixture was stirred two hours with cooling then partially... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfone | null | null | c1ccccc1 | null | O | null | 2 | CSCc1ccc(O)c(C(C)=O)c1>O>CC(=O)c1cc(CS(C)(=O)=O)ccc1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-58e4f6ee25724c079c75ffc776570d5f | CC(=O)c1cc(CCl)ccc1O.CS(N)(=O)=O>>CC(=O)c1cc(CNS(C)(=O)=O)ccc1O | CS(=O)(=O)N.[H-].[Na+].ClCC=1C=CC(=C(C1)C(C)=O)O.Cl>>OC1=C(C=C(C=C1)CNS(=O)(=O)C)C(C)=O | Cl[CH2:7][c:6]1[cH:5][c:4]([C:2]([CH3:1])=[O:3])[c:15]([OH:16])[cH:14][cH:13]1.[NH2:8][S:9]([CH3:10])(=[O:11])=[O:12]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([CH2:7][NH:8][S:9]([CH3:10])(=[O:11])=[O:12])[cH:13][cH:14][c:15]1[OH:16] | CC(=O)c1cc(CCl)ccc1O.CS(N)(=O)=O | CC(=O)c1cc(CNS(C)(=O)=O)ccc1O | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | 4b9697564fc265ba44ddc16e54c39ac37f4ae3b83733e16918a5dac2d316c1f0 | 3fe6b65897247a134b277f2a2d6b241ddeabbd8a2611ba8aad88f24ab3c1380a | c1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[#16:6](-[NH2;D1;+0:7])(=[O;D1;H0:8])=[O;D1;H0:9]>>[C;D1;H3:5]-[#16:6](=[O;D1;H0:8])(=[O;D1;H0:9])-[NH;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 12.3 | [{"value": 12.0, "product": "OC1=C(C=C(C=C1)CNS(=O)(=O)C)C(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 12.3, "product": "OC1=C(C=C(C=C1)CNS(=O)(=O)C)C(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a mixture of sodium hydride (60% dispersion in mineral oil, 1.60 g, 40.0 mmol) in 25 mL DMSO under Argon was added dropwise a solution of methanesulfonamide (3.80 g, 40.0 mmol) in 10 mL DMSO. The resulting mixture was stirred 30 minutes and a solution of 5'-(chloromethyl)-2'-hydroxyacetophenone (3.69 g, 20.0 mmol) i... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary halide | Sulfonamide | null | null | c1ccccc1 | HCl | CS(=O)C | null | 0.5 | CC(=O)c1cc(CCl)ccc1O.CS(N)(=O)=O>CS(=O)C>CC(=O)c1cc(CNS(C)(=O)=O)ccc1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-34d79860ad584cf385dcffca66a922f8 | CC(=O)c1cc(CCl)ccc1O.COCCO>>COCCOCc1ccc(O)c(C(C)=O)c1 | ClCC=1C=CC(=C(C1)C(C)=O)O.C([O-])([O-])=O.[K+].[K+].COCCO>>OC1=C(C=C(C=C1)COCCOC)C(C)=O | Cl[CH2:6][c:7]1[cH:8][cH:9][c:10]([OH:11])[c:12]([C:13]([CH3:14])=[O:15])[cH:16]1.[CH3:1][O:2][CH2:3][CH2:4][OH:5]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([OH:11])[c:12]([C:13]([CH3:14])=[O:15])[cH:16]1 | CC(=O)c1cc(CCl)ccc1O.COCCO | COCCOCc1ccc(O)c(C(C)=O)c1 | null | null | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | c1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 18 | [{"value": 18.0, "product": "OC1=C(C=C(C=C1)COCCOC)C(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 17.8, "product": "OC1=C(C=C(C=C1)COCCOC)C(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | A mixture of 5'-(chloromethyl)-2'-hydroxyacetophenone (1.85 g, 10.0 mmol), potassium carbonate (1.38, 10.0 mmol), 2-methoxyethanol (0.91 g, 12.0 mmol) and 10 mL chloroform was stirred 24 hours, filtered, and the filtrate concentrated in vacuo to give a residue. The residue was purified by flash chromatography eluting w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | c1ccccc1 | HCl | C(Cl)(Cl)Cl | null | 24 | CC(=O)c1cc(CCl)ccc1O.COCCO>C(Cl)(Cl)Cl>COCCOCc1ccc(O)c(C(C)=O)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-08e1b55496fe4cbebd59e0dd24ef1b14 | CC(=O)c1cc(CCl)ccc1O.O=C1CCCN1>>CC(=O)c1cc(CN2CCCC2=O)ccc1O | N1C(CCC1)=O.[H-].[Na+].ClCC=1C=CC(=C(C1)C(C)=O)O.Cl>>C(C)(=O)C=1C=C(C=CC1O)CN1C(CCC1)=O | Cl[CH2:7][c:6]1[cH:5][c:4]([C:2]([CH3:1])=[O:3])[c:16]([OH:17])[cH:15][cH:14]1.[NH:8]1[CH2:9][CH2:10][CH2:11][C:12]1=[O:13]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([CH2:7][N:8]2[CH2:9][CH2:10][CH2:11][C:12]2=[O:13])[cH:14][cH:15][c:16]1[OH:17] | CC(=O)c1cc(CCl)ccc1O.O=C1CCCN1 | CC(=O)c1cc(CN2CCCC2=O)ccc1O | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | f5f217f17d493fffc808e7019c66db8bb20f63ec70b29db349ba715e196bdaf0 | 4a6c1e88c9e8bed487b746792f88d478ff36cc235f9a217d4632e6babdebdc9a | O=C1CCCN1Cc1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[C:7]-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[O;D1;H0:5]=[C:6]1-[C:7]-[C:8]-[C:9]-[N;H0;D3;+0:10]-1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 82.3 | [{"value": 82.0, "product": "C(C)(=O)C=1C=C(C=CC1O)CN1C(CCC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.3, "product": "C(C)(=O)C=1C=C(C=CC1O)CN1C(CCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a suspension of sodium hydride (60% dispersion in mineral oil, 0.80 g, 20.0 mmol) in 15 mL dry dimethylformamide under argon, cooled in an ice-bath was added dropwise a solution of 2-pyrrolidinone (1.70 g, 20.0 mmol) in 5 mL dimethylformamide. The ice-bath was removed, the mixture was stirred 30 minutes, and a solut... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amide | Tertiary amide | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1 | HCl | CN(C=O)C | null | 0.5 | CC(=O)c1cc(CCl)ccc1O.O=C1CCCN1>CN(C=O)C>CC(=O)c1cc(CN2CCCC2=O)ccc1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-dc93e323f5dd4fdea38a1dcf99643bf1 | CC(=O)c1cc(CCl)ccc1O.O=C1NCCN1>>CC(=O)c1cc(CN2CCNC2=O)ccc1O | [H-].[Na+].ClCC=1C=CC(=C(C1)C(C)=O)O.N1C(NCC1)=O>>C(C)(=O)C=1C=C(C=CC1O)CN1C(NCC1)=O | Cl[CH2:7][c:6]1[cH:5][c:4]([C:2]([CH3:1])=[O:3])[c:16]([OH:17])[cH:15][cH:14]1.[NH:8]1[CH2:9][CH2:10][NH:11][C:12]1=[O:13]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([CH2:7][N:8]2[CH2:9][CH2:10][NH:11][C:12]2=[O:13])[cH:14][cH:15][c:16]1[OH:17] | CC(=O)c1cc(CCl)ccc1O.O=C1NCCN1 | CC(=O)c1cc(CN2CCNC2=O)ccc1O | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 9e337ae0278d976da02093acd3b0ff1860ee7514970cc3a05771bc3416d56448 | 9068cdf0ef9ef7510e3ed725979384397a613e011a5abb0653feb8d5b2408c81 | O=C1NCCN1Cc1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[#7:7]-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[O;D1;H0:5]=[C:6]1-[#7:7]-[C:8]-[C:9]-[N;H0;D3;+0:10]-1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 43.1 | [{"value": 43.0, "product": "C(C)(=O)C=1C=C(C=CC1O)CN1C(NCC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.1, "product": "C(C)(=O)C=1C=C(C=CC1O)CN1C(NCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a suspension of sodium hydride (60% dispersion in mineral oil, 0.80 g, 20.0 mmol) in 15 mL dry dimethylformamide under argon, cooled in an ice-bath was added dropwise a solution of 2-imidazolidone (1.72 g, 20.0 mmol) in 5 mL dimethylformamide. The ice bath was removed, the mixture was stirred 30 minutes and a soluti... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Urea | Urea | C1CNCN1 | C1CNC[NH]1 | c1ccccc1.C1CNC[NH]1 | HCl | CN(C=O)C | null | 0.5 | CC(=O)c1cc(CCl)ccc1O.O=C1NCCN1>CN(C=O)C>CC(=O)c1cc(CN2CCNC2=O)ccc1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-310c58e7bbc14872a5a2fd0b11d6f844 | C1CC2(CCN1)OCCO2.O=[N+]([O-])c1ccc(CCBr)cc1>>O=[N+]([O-])c1ccc(CCC2COC3(CCNCC3)O2)cc1 | O1CCOC12CCNCC2.C([O-])([O-])=O.[K+].[K+].[N+](=O)([O-])C1=CC=C(C=C1)CCBr>>[N+](=O)([O-])C1=CC=C(C=C1)CCC1OC2(OC1)CCNCC2 | [CH2:10]1[CH2:11][O:12][C:13]2([CH2:14][CH2:15][NH:16][CH2:17][CH2:18]2)[O:19]1.Br[CH2:9][CH2:8][c:7]1[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:21][cH:20]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][CH2:9][CH:10]2[CH2:11][O:12][C:13]3([CH2:14][CH2:15][NH:16][CH2:17][CH2:18]3)[O:19]2)[cH:20][cH:21]1 | C1CC2(CCN1)OCCO2.O=[N+]([O-])c1ccc(CCBr)cc1 | O=[N+]([O-])c1ccc(CCC2COC3(CCNCC3)O2)cc1 | null | null | C(C)#N | C-C Coupling | OtherReaction | c66afc65e24cb62c882739e3a122ebd7ace4fc27b44a2c5954ad220497e3a037 | 2c1c1647472d7e3cff37f0f3aad955b760f0ad2f8b7aa7e7825b1c0344bab3bb | c1ccc(CCC2COC3(CCNCC3)O2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[c:3].[#8:4]1-[C:5]-[CH2;D2;+0:6]-[#8:7]-[C:8]-1>>[c:3]-[C:2]-[CH2;D2;+0:1]-[CH;D3;+0:6]1-[#8:7]-[C:8]-[#8:4]-[C:5]-1 | null | [] | 0 | CELSIUS | 10 | MINUTE | 1,4-Dioxa-8-azaspiro[4.5]-decane (18.62 g, 130 mmoles) in 50 mL of acetonitrile was stirred under argon and treated with anhydrous potassium carbonate (27.60 g, 200 mmoles). The mixture was cooled to 0° C. and 2-(4-nitrophenyl)ethylbromide (23.01 g, 100 mmoles) was added in one portion. After 10 minutes, the ice bath w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether | Ether | C1CC2(CCN1)OCCO2 | C1CC2(CCN1)OCCO2 | c1ccccc1.C1CC2(CCN1)OCCO2 | HBr | C(C)#N | 0 | 0.166667 | C1CC2(CCN1)OCCO2.O=[N+]([O-])c1ccc(CCBr)cc1>C(C)#N>O=[N+]([O-])c1ccc(CCC2COC3(CCNCC3)O2)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-a2c1a5bf1f6c453393f3e3747eac03ce | CC(=O)OC(C)=O.CC(=O)OC(C)=O.Nc1ccc(CCN2CCC3(CC2)OCCO3)cc1.O=[N+]([O-])O>>CC(=O)Nc1ccc(CCN2CCC3(CC2)OCCO3)cc1[N+](=O)[O-].CC(=O)O | C(C)(=O)OC(C)=O.NC1=CC=C(C=C1)CCN1CCC2(OCCO2)CC1.[N+](=O)(O)[O-].C(C)(=O)OC(C)=O>>C(C)(=O)O.N(C(=O)C)C1=C(C=C(C=C1)CCN1CCC2(OCCO2)CC1)[N+](=O)[O-] | CC(=O)[O:29][C:27]([CH3:26])=[O:28].CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][c:8]([CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][C:14]3([CH2:15][CH2:16]2)[O:17][CH2:18][CH2:19][O:20]3)[cH:21][cH:22]1.O[N+:23](=[O:24])[O-:25]>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][... | CC(=O)OC(C)=O.CC(=O)OC(C)=O.Nc1ccc(CCN2CCC3(CC2)OCCO3)cc1.O=[N+]([O-])O | CC(=O)Nc1ccc(CCN2CCC3(CC2)OCCO3)cc1[N+](=O)[O-].CC(=O)O | null | null | [Cl-].[Na+].O.C(Cl)Cl | Acylation | OtherReaction | 3fe925e789c7af32c97d8e327c658191abf45cdab6265c77681e8bb2b1ae9e60 | c70ebc153fece6477741db56cc6e65053f7fa07f58324ca5bad12977626bef94 | c1ccc(CCN2CCC3(CC2)OCCO3)cc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].C-C(=O)-[O;H0;D2;+0:4]-[C:5](-[C;D1;H3:6])=[O;D1;H0:7].O-[N+;H0;D3:8](-[O;-;D1;H0:9])=[O;D1;H0:10].[NH2;D1;+0:11]-[c:12](:[c:13]):[cH;D2;+0:14]:[c:15]:[c:16]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:11]-[c:12](:[c:13]):[c;H0;D3;+0:14](-[N+;H0;D3:8](-[O;-;D1;... | 89 | [{"value": 89.0, "product": "C(C)(=O)O.N(C(=O)C)C1=C(C=C(C=C1)CCN1CCC2(OCCO2)CC1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | -5 | CELSIUS | 18 | HOUR | A mechanically stirred solution of N(2-(4-aminophenyl)ethyl)-1,4-dioxa-8-azaspiro[4.5]-decane in methylene chloride (400 mL) cooled to -5° C. under an argon atmosphere was treated dropwise with acetic anhydride (58.8 mL, 622 mmoles). The reaction was allowed to reach room temperature and was stirred for 18 hr. After th... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Anhydride.Nitrate.Primary amine | Carboxylic acid.Nitro group.Secondary amide | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CC2(CC[NH]1)OCCO2 | HO- | [Cl-].[Na+].O.C(Cl)Cl | -5 | 18 | CC(=O)OC(C)=O.CC(=O)OC(C)=O.Nc1ccc(CCN2CCC3(CC2)OCCO3)cc1.O=[N+]([O-])O>[Cl-].[Na+].O.C(Cl)Cl>CC(=O)Nc1ccc(CCN2CCC3(CC2)OCCO3)cc1[N+](=O)[O-].CC(=O)O |
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