dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-88b026a5d5ba4f24b8b105d199c7161c | COCOc1cccc(C(C)=O)c1.OCCO>>COCOc1cccc(C2(C)OCCO2)c1 | COCOC1=CC(=CC=C1)C(C)=O.C(CO)O>>CC1(OCCO1)C=1C=C(C=CC1)OCOC | [CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][c:9]([C:10]([CH3:11])=[O:12])[cH:16]1.O[CH2:13][CH2:14][OH:15]>>[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][c:9]([C:10]2([CH3:11])[O:12][CH2:13][CH2:14][O:15]2)[cH:16]1 | COCOc1cccc(C(C)=O)c1.OCCO | COCOc1cccc(C2(C)OCCO2)c1 | null | S(=O)(=O)([O-])C1=CC=C(C)C=C1.[NH+]1=CC=CC=C1 | C1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | 2baa95c632045e217509d8ec12cda8674252268fe3f8cb44eb2e5ebe0f27c30f | f8121a7732f8ef583111433d2b2d82886bf3a134c51dc6363d813c8cbf4e36f5 | c1ccc(C2OCCO2)cc1 | O-[CH2;D2;+0:1]-[C:2]-[OH;D1;+0:3].[C;D1;H3:4]-[C;H0;D3;+0:5](=[O;H0;D1;+0:6])-[c:7](:[c:8]):[c:9]>>[C;D1;H3:4]-[C;H0;D4;+0:5]1(-[c:7](:[c:8]):[c:9])-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-1 | 61 | [{"value": 61.0, "product": "CC1(OCCO1)C=1C=C(C=CC1)OCOC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.0, "product": "CC1(OCCO1)C=1C=C(C=CC1)OCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-(acetyl)phenyl methoxymethyl ether (3.6 g, 20 mmol), ethylene glycol (3.72 g, 60 mmol) and pyridinium tosylate (0.075 g, 0.3 mmol, 3 mol %) in benzene (200 mL) was azeotropically refluxed for 8 h. The reaction was concentrated and the resulting residue was diluted with ethyl ether (150 mL) and washed wit... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary alcohol.Primary alcohol | Ether.Ether | null | C1COCO1 | c1ccccc1.C1COCO1 | HO- | S(=O)(=O)([O-])C1=CC=C(C)C=C1.[NH+]1=CC=CC=C1.C1=CC=CC=C1 | null | null | COCOc1cccc(C(C)=O)c1.OCCO>S(=O)(=O)([O-])C1=CC=C(C)C=C1.[NH+]1=CC=CC=C1.C1=CC=CC=C1>COCOc1cccc(C2(C)OCCO2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f7e815d18ea74850b93ae3550c8d918f | CC(C)(C)OC(=O)NCC#CCN.O=C(O)CCCCC(c1ccc(F)cc1)c1ccc(F)cc1>>CC(C)(C)OC(=O)NCC#CCNC(=O)CCCCC(c1ccc(F)cc1)c1ccc(F)cc1 | C(CCl)Cl.C(C)(C)(C)OC(NCC#CCN)=O.FC1=CC=C(C=C1)C(CCCCC(=O)O)C1=CC=C(C=C1)F>>C(C)(C)(C)OC(NCC#CCNC(CCCCC(C1=CC=C(C=C1)F)C1=CC=C(C=C1)F)=O)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]#[C:11][CH2:12][NH2:13].O[C:14](=[O:15])[CH2:16][CH2:17][CH2:18][CH2:19][CH:20]([c:21]1[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]1)[c:28]1[cH:29][cH:30][c:31]([F:32])[cH:33][cH:34]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]#[C... | CC(C)(C)OC(=O)NCC#CCN.O=C(O)CCCCC(c1ccc(F)cc1)c1ccc(F)cc1 | CC(C)(C)OC(=O)NCC#CCNC(=O)CCCCC(c1ccc(F)cc1)c1ccc(F)cc1 | null | CN(C)C=1C=CN=CC1 | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(Cc2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6]#[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[C:8]-[C:7]#[C:6]-[C:5] | 72 | [{"value": 72.0, "product": "C(C)(C)(C)OC(NCC#CCNC(CCCCC(C1=CC=C(C=C1)F)C1=CC=C(C=C1)F)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of (4-Amino-but-2-ynyl)-carbamic acid tert-butyl ester (0.8 g, 4.34 mmol) in dry CH2Cl2 (40 ml) was added 6,6-bis-(4-fluorophenyl)-hexanoic acid (1.32 g, 4.4 mmol) under nitrogen. To the reaction was added EDC (1.66 g, 8.68 mmol) and DMAP (cat) and the reaction mixture stirred under nitrogen at room tempe... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | CN(C)C=1C=CN=CC1.C(Cl)Cl | null | 8 | CC(C)(C)OC(=O)NCC#CCN.O=C(O)CCCCC(c1ccc(F)cc1)c1ccc(F)cc1>CN(C)C=1C=CN=CC1.C(Cl)Cl>CC(C)(C)OC(=O)NCC#CCNC(=O)CCCCC(c1ccc(F)cc1)c1ccc(F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-008d490ab3034c50ba37867aa493072d | CC(C)(C)OC(=O)NCC#CCNC(=O)CCCCC(c1ccc(F)cc1)c1ccc(F)cc1>>NCC#CCNC(=O)CCCCC(c1ccc(F)cc1)c1ccc(F)cc1 | C(C)(C)(C)OC(NCC#CCNC(CCCCC(C1=CC=C(C=C1)F)C1=CC=C(C=C1)F)=O)=O.C(=O)(C(F)(F)F)O>>NCC#CCNC(CCCCC(C1=CC=C(C=C1)F)C1=CC=C(C=C1)F)=O | CC(C)(C)OC(=O)[NH:1][CH2:2][C:3]#[C:4][CH2:5][NH:6][C:7](=[O:8])[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([c:14]1[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]1)[c:21]1[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]1>>[NH2:1][CH2:2][C:3]#[C:4][CH2:5][NH:6][C:7](=[O:8])[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([c:14]1[cH:15][cH:16][c:... | CC(C)(C)OC(=O)NCC#CCNC(=O)CCCCC(c1ccc(F)cc1)c1ccc(F)cc1 | NCC#CCNC(=O)CCCCC(c1ccc(F)cc1)c1ccc(F)cc1 | null | null | C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc(Cc2ccccc2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]#[C:4]-[C:5]>>[C:5]-[C:4]#[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | 2 | HOUR | {4-[6,6-bis-(4-fluoro-phenyl)-hexanoylamino]-but-2-ynyl}-carbamic acid tert-butyl ester (1.6 g, 3.4 mmol) was dissolved in dry CH2Cl2 (50 ml) followed by addition of TFA (20 ml). The resulting solution was stirred at room temperature for 2 hrs. The solution was concentrated under reduced pressure. The resulting residue... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl | null | 2 | CC(C)(C)OC(=O)NCC#CCNC(=O)CCCCC(c1ccc(F)cc1)c1ccc(F)cc1>C(Cl)Cl>NCC#CCNC(=O)CCCCC(c1ccc(F)cc1)c1ccc(F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9cdc826fca4742448ad1df9f3e7630f6 | NCC#CCNC(=O)CCCCC(c1ccc(F)cc1)c1ccc(F)cc1.O=C(O)c1ccc(Cl)cc1>>O=C(CCCCC(c1ccc(F)cc1)c1ccc(F)cc1)NCC#CCNC(=O)c1ccc(Cl)cc1 | C(CCl)Cl.NCC#CCNC(CCCCC(C1=CC=C(C=C1)F)C1=CC=C(C=C1)F)=O.ClC1=CC=C(C(=O)O)C=C1>>FC1=CC=C(C=C1)C(CCCCC(=O)NCC#CCNC(C1=CC=C(C=C1)Cl)=O)C1=CC=C(C=C1)F | [O:1]=[C:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH:7]([c:8]1[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]1)[c:15]1[cH:16][cH:17][c:18]([F:19])[cH:20][cH:21]1)[NH:22][CH2:23][C:24]#[C:25][CH2:26][NH2:27].O[C:28](=[O:29])[c:30]1[cH:31][cH:32][c:33]([Cl:34])[cH:35][cH:36]1>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH:7]([c:8]1[cH:9]... | NCC#CCNC(=O)CCCCC(c1ccc(F)cc1)c1ccc(F)cc1.O=C(O)c1ccc(Cl)cc1 | O=C(CCCCC(c1ccc(F)cc1)c1ccc(F)cc1)NCC#CCNC(=O)c1ccc(Cl)cc1 | null | CN(C)C=1C=CN=CC1 | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CCCCC(c1ccccc1)c1ccccc1)NCC#CCNC(=O)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]#[C:8]-[C:9]-[NH2;D1;+0:10]>>[C:6]-[C:7]#[C:8]-[C:9]-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 8 | HOUR | To a solution of 6,6-bis-(4-fluoro-phenyl)-hexanoic acid (4-amino-but-2-ynyl)-amide (0.69 g, 1.86 mmol) in dry CH2Cl2 (40 ml) was added 4-chlorobenzoic acid (0.29 g, 1.86 mmol) under nitrogen. To the reaction was added EDC (0.71 g, 3.72 mmol) and DMAP (cat) and the reaction mixture stirred under nitrogen at room temper... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | CN(C)C=1C=CN=CC1.C(Cl)Cl | null | 8 | NCC#CCNC(=O)CCCCC(c1ccc(F)cc1)c1ccc(F)cc1.O=C(O)c1ccc(Cl)cc1>CN(C)C=1C=CN=CC1.C(Cl)Cl>O=C(CCCCC(c1ccc(F)cc1)c1ccc(F)cc1)NCC#CCNC(=O)c1ccc(Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-887cafe0ffaa468a9ba62f329506d600 | BrC/C=C/CBr.O.O=C1NC(=O)c2ccccc21>>O=C1c2ccccc2C(=O)N1C/C=C/CN1C(=O)c2ccccc2C1=O | C1(C=2C(C(N1)=O)=CC=CC2)=O.[K].BrC\C=C\CBr.O>>C1(C=2C(C(N1C\C=C\CN1C(C=3C(C1=O)=CC=CC3)=O)=O)=CC=CC2)=O | Br[CH2:12]/[CH:13]=[CH:2]/[CH2:15]Br.[OH2:1].[C:9]1(=[O:10])[NH:11][C:25](=[O:26])[c:24]2[c:19]1[cH:20][cH:21][cH:22][cH:23]2>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12]/[CH:13]=[CH:14]/[CH2:15][N:16]1[C:17](=[O:18])[c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]2[C:25]1=[O:26] | BrC/C=C/CBr.O.O=C1NC(=O)c2ccccc21 | O=C1c2ccccc2C(=O)N1C/C=C/CN1C(=O)c2ccccc2C1=O | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | e3c206f42090601b424ad74fecc08b2e57a5da9de871eaa10964d1051529f898 | ae23a80aefd2e342eb30ae6f37c34c2611645251bedcbdce152e6c373157e32c | O=C1c2ccccc2C(=O)N1C/C=C/CN1C(=O)c2ccccc2C1=O | Br-[CH2;D2;+0:1]/[CH;D2;+0:2]=[CH;D2;+0:3]/[CH2;D2;+0:4]-Br.[O;D1;H0:5]=[C;H0;D3;+0:6]1-[NH;D2;+0:7]-[C;H0;D3;+0:8](=[O;D1;H0:9])-[c:10](:[c:11]):[c;H0;D3;+0:12]-1:[c:13]:[c:14].[OH2;D0;+0:15]>>[O;D1;H0:5]=[C;H0;D3;+0:6]1-[N;H0;D3;+0:7](-[CH2;D2;+0:1]/[CH;D2;+0:2]=[C:16]/[CH2;D2;+0:4]-[#7:17]2-[C:18](=[O;D1;H0:19])-[c;... | 91 | [{"value": 91.0, "product": "C1(C=2C(C(N1C\\C=C\\CN1C(C=3C(C1=O)=CC=CC3)=O)=O)=CC=CC2)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | Potassium phathalimide (20 g, 108 mmol) was added in portions over 2 h to a stirred solution of (E)-1,4-dibromobut-2-ene (10.7 g, 50 mmol) in DMF (100 ml) at room temperature. The mixture was stirred for a further 3 days at this temperature, then poured into water (100 ml), and the mixture was extracted with dichlorome... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Unsubstituted dicarboximide | Substituted dicarboximide.Substituted dicarboximide | c1ccc2c(c1)CNC2 | c1ccc2c(c1)C[NH]C2.c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccc2c(c1)C[NH]C2 | Br- | CN(C)C=O | null | 72 | BrC/C=C/CBr.O.O=C1NC(=O)c2ccccc21>CN(C)C=O>O=C1c2ccccc2C(=O)N1C/C=C/CN1C(=O)c2ccccc2C1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b99053da8cdb4aa38b70d72883355bff | CC(C)(C)OC(=O)NCC=CCN.O=C(O)CCCCC(c1ccc(F)cc1)c1ccc(F)cc1>>CC(C)(C)OC(=O)NCC=CCNC(=O)CCCCC(c1ccc(F)cc1)c1ccc(F)cc1 | C(CCl)Cl.C(C)(C)(C)OC(NCC=CCN)=O.FC1=CC=C(C=C1)C(CCCCC(=O)O)C1=CC=C(C=C1)F>>C(C)(C)(C)OC(NCC=CCNC(CCCCC(C1=CC=C(C=C1)F)C1=CC=C(C=C1)F)=O)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH:10]=[CH:11][CH2:12][NH2:13].O[C:14](=[O:15])[CH2:16][CH2:17][CH2:18][CH2:19][CH:20]([c:21]1[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]1)[c:28]1[cH:29][cH:30][c:31]([F:32])[cH:33][cH:34]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH:10]... | CC(C)(C)OC(=O)NCC=CCN.O=C(O)CCCCC(c1ccc(F)cc1)c1ccc(F)cc1 | CC(C)(C)OC(=O)NCC=CCNC(=O)CCCCC(c1ccc(F)cc1)c1ccc(F)cc1 | null | CN(C)C=1C=CN=CC1 | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(Cc2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6]=[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[C:8]-[C:7]=[C:6]-[C:5] | 70 | [{"value": 70.0, "product": "C(C)(C)(C)OC(NCC=CCNC(CCCCC(C1=CC=C(C=C1)F)C1=CC=C(C=C1)F)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of (4-amino-but-2-enyl)-carbamic acid tert-butyl ester (1.0 g, 5.36 mmol) in dry CH2Cl2 (40 ml) was added 6,6-bis-(4-fluorophenyl)-hexanoic acid (1.62 g, 5.36 mmol) under nitrogen. To the reaction was added EDC (2.04 g, 10.72 mmol) and DMAP (cat) and the reaction mixture stirred under nitrogen at room tem... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | CN(C)C=1C=CN=CC1.C(Cl)Cl | null | 8 | CC(C)(C)OC(=O)NCC=CCN.O=C(O)CCCCC(c1ccc(F)cc1)c1ccc(F)cc1>CN(C)C=1C=CN=CC1.C(Cl)Cl>CC(C)(C)OC(=O)NCC=CCNC(=O)CCCCC(c1ccc(F)cc1)c1ccc(F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-379073833c7b48c289e7f74c73906501 | CC(C)(C)OC(=O)NCC=CCNC(=O)CCCCC(c1ccc(F)cc1)c1ccc(F)cc1>>NCC=CCNC(=O)CCCCC(c1ccc(F)cc1)c1ccc(F)cc1 | C(C)(C)(C)OC(NCC=CCNC(CCCCC(C1=CC=C(C=C1)F)C1=CC=C(C=C1)F)=O)=O.C(=O)(C(F)(F)F)O>>NCC=CCNC(CCCCC(C1=CC=C(C=C1)F)C1=CC=C(C=C1)F)=O | CC(C)(C)OC(=O)[NH:1][CH2:2][CH:3]=[CH:4][CH2:5][NH:6][C:7](=[O:8])[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([c:14]1[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]1)[c:21]1[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]1>>[NH2:1][CH2:2][CH:3]=[CH:4][CH2:5][NH:6][C:7](=[O:8])[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([c:14]1[cH:15][cH:16... | CC(C)(C)OC(=O)NCC=CCNC(=O)CCCCC(c1ccc(F)cc1)c1ccc(F)cc1 | NCC=CCNC(=O)CCCCC(c1ccc(F)cc1)c1ccc(F)cc1 | null | null | C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc(Cc2ccccc2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]=[C:4]-[C:5]>>[C:5]-[C:4]=[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | 2 | HOUR | {4-[6,6-Bis-(4-fluoro-phenyl)-hexanoylamino]-but-2-enyl}-carbamic acid tert-butyl ester (1.6 g, 4.3 mmol) was dissolved in dry CH2Cl2 (50 ml) followed by addition of TFA (20 ml). The resulting solution was stirred at room temperature for 2 hrs. The solution was concentrated under reduced pressure. The resulting residue... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl | null | 2 | CC(C)(C)OC(=O)NCC=CCNC(=O)CCCCC(c1ccc(F)cc1)c1ccc(F)cc1>C(Cl)Cl>NCC=CCNC(=O)CCCCC(c1ccc(F)cc1)c1ccc(F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2940923604a94178889d3602dcb92049 | CCOP(=O)(C(=O)c1ccccc1)c1ccc(C)c(C)c1C>>Cc1ccc(P(=O)([O-])C(=O)c2ccccc2)c(C)c1C | CC1=C(C(=C(C=C1)P(OCC)(=O)C(C1=CC=CC=C1)=O)C)C.[I-].[Na+]>>[Na+].CC1=C(C(=C(C=C1)P([O-])(=O)C(C1=CC=CC=C1)=O)C)C | CC[O:8][P:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:19]([CH3:20])[c:17]1[CH3:18])(=[O:7])[C:9](=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([P:6](=[O:7])([O-:8])[C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]([CH3:18])[c:19]1[CH3:20] | CCOP(=O)(C(=O)c1ccccc1)c1ccc(C)c(C)c1C | Cc1ccc(P(=O)([O-])C(=O)c2ccccc2)c(C)c1C | null | null | CC(=O)CC | Functional Group Interconversion | OtherReaction | 42af6cdfb86a130c92365e01a31b50705eea7bdf12f67dc370bf24402f7ceedc | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | O=C(c1ccccc1)[PH](=O)c1ccccc1 | C-C-[O;H0;D2;+0:1]-[#15:2](=[O;D1;H0:3])(-[c:4])-[C:5](=[O;D1;H0:6])-[c:7]>>[O-;H0;D1:1]-[#15:2](=[O;D1;H0:3])(-[c:4])-[C:5](=[O;D1;H0:6])-[c:7] | null | [] | 65 | CELSIUS | 15 | MINUTE | 644 g of ethyl trimethylbenzoylphenylphosphinate (Lucirin® TPO-L, BASF AG) were initially introduced in 3000 ml of ethyl methyl ketone, and 1.1 equivalents (285 g) of sodium iodide were added to the solution. After 15 minutes, the homogeneous solution was heated to 65° C. and stirred for 24 hours. The yellow precipitat... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccccc1 | Other | CC(=O)CC | 65 | 0.25 | CCOP(=O)(C(=O)c1ccccc1)c1ccc(C)c(C)c1C>CC(=O)CC>Cc1ccc(P(=O)([O-])C(=O)c2ccccc2)c(C)c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-035e490eb66b4793b511ec5eb9352753 | Cc1ccc(P(=O)([O-])C(=O)c2ccccc2)c(C)c1C>>Cc1ccc(P(=O)(O)C(=O)c2ccccc2)c(C)c1C | [Na+].CC1=C(C(=C(C=C1)P([O-])(=O)C(C1=CC=CC=C1)=O)C)C.S(O)(O)(=O)=O>>CC1=C(C(=C(C=C1)P(O)(=O)C(C1=CC=CC=C1)=O)C)C | [CH3:1][c:2]1[cH:3][cH:4][c:5]([P:6](=[O:7])([O-:8])[C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]([CH3:18])[c:19]1[CH3:20]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([P:6](=[O:7])([OH:8])[C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]([CH3:18])[c:19]1[CH3:20] | Cc1ccc(P(=O)([O-])C(=O)c2ccccc2)c(C)c1C | Cc1ccc(P(=O)(O)C(=O)c2ccccc2)c(C)c1C | null | null | O | Reduction | OtherReaction | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | O=C(c1ccccc1)[PH](=O)c1ccccc1 | [O-;H0;D1:1]-[#15:2](=[O;D1;H0:3])(-[c:4])-[C:5](=[O;D1;H0:6])-[c:7]>>[O;D1;H0:6]=[C:5](-[c:7])-[#15:2](=[O;D1;H0:3])(-[OH;D1;+0:1])-[c:4] | null | [] | null | null | 1 | HOUR | 401.55 g of the sodium salt from Example 1 were dissolved in 1500 ml of water acidified to pH 1 with 1300 ml of 0.5 molar sulfuric acid. After 1 hour, the crystal batch which had precipitated was filtered off with suction, washed twice with 700 ml of water each time and sucked dry. The filter cake was dried azeotropica... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccccc1 | null | O | null | 1 | Cc1ccc(P(=O)([O-])C(=O)c2ccccc2)c(C)c1C>O>Cc1ccc(P(=O)(O)C(=O)c2ccccc2)c(C)c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5ebcf41f0919404d881ce0e443e6e7e3 | Cc1ccc(P(=O)(O)C(=O)c2ccccc2)c(C)c1C.O=S(Cl)Cl>>Cc1ccc(P(=O)(Cl)C(=O)c2ccccc2)c(C)c1C | CC1=C(C(=C(C=C1)P(O)(=O)C(C1=CC=CC=C1)=O)C)C.N1=CC=CC=C1.S(=O)(Cl)Cl>>CC1=C(C(=C(C=C1)P(=O)(C(C1=CC=CC=C1)=O)Cl)C)C | O[P:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:19]([CH3:20])[c:17]1[CH3:18])(=[O:7])[C:9](=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1.O=S(Cl)[Cl:8]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([P:6](=[O:7])([Cl:8])[C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]([CH3:18])[c:19]1[CH3:20] | Cc1ccc(P(=O)(O)C(=O)c2ccccc2)c(C)c1C.O=S(Cl)Cl | Cc1ccc(P(=O)(Cl)C(=O)c2ccccc2)c(C)c1C | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | 42af6cdfb86a130c92365e01a31b50705eea7bdf12f67dc370bf24402f7ceedc | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | O=C(c1ccccc1)[PH](=O)c1ccccc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[P;H0;D4;+0:2](=[O;D1;H0:3])(-[C:4](=[O;D1;H0:5])-[c:6])-[c:7](:[c:8]):[c:9]>>[Cl;H0;D1;+0:1]-[P;H0;D4;+0:2](=[O;D1;H0:3])(-[C:4](=[O;D1;H0:5])-[c:6])-[c:7](:[c:8]):[c:9] | null | [] | 0 | CELSIUS | null | null | 250 g of the acid from Example 2 were suspended in 670 ml of toluene and dissolved with 102.6 g of pyridine. 1546 g of thionyl chloride were added dropwise to the reaction mixture at 60° C. over the course of 1 hour. After a post-reaction time of 3 hours, the red-brown emulsion was cooled to 0° C., and the rust-brown c... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccccc1 | HCl | C1(=CC=CC=C1)C | 0 | null | Cc1ccc(P(=O)(O)C(=O)c2ccccc2)c(C)c1C.O=S(Cl)Cl>C1(=CC=CC=C1)C>Cc1ccc(P(=O)(Cl)C(=O)c2ccccc2)c(C)c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-60ff1548a5584a9a8bd3eac1f36012ec | CCOP(=O)(C(=O)c1ccccc1)c1ccc(C)c(C)c1C>>Cc1ccc(P(=O)(O)C(=O)c2ccccc2)c(C)c1C | OS(=O)(=O)O.[Li+].[Cl-].CC1=C(C(=C(C=C1)P(OCC)(=O)C(C1=CC=CC=C1)=O)C)C>>CC1=C(C(=C(C=C1)P(O)(=O)C(C1=CC=CC=C1)=O)C)C | CC[O:8][P:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:19]([CH3:20])[c:17]1[CH3:18])(=[O:7])[C:9](=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([P:6](=[O:7])([OH:8])[C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]([CH3:18])[c:19]1[CH3:20] | CCOP(=O)(C(=O)c1ccccc1)c1ccc(C)c(C)c1C | Cc1ccc(P(=O)(O)C(=O)c2ccccc2)c(C)c1C | null | null | CN(C)C=O.CN(C=O)C | Deprotection | OtherReaction | eaaf8436ac19e7e26db9ff78e61eed5caf13b9167196c3230a9e1eb66b295f8b | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | O=C(c1ccccc1)[PH](=O)c1ccccc1 | C-C-[O;H0;D2;+0:1]-[#15:2](=[O;D1;H0:3])(-[c:4])-[C:5](=[O;D1;H0:6])-[c:7]>>[O;D1;H0:6]=[C:5](-[c:7])-[#15:2](=[O;D1;H0:3])(-[OH;D1;+0:1])-[c:4] | 98 | [{"value": 98.0, "product": "CC1=C(C(=C(C=C1)P(O)(=O)C(C1=CC=CC=C1)=O)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.5, "product": "CC1=C(C(=C(C=C1)P(O)(=O)C(C1=CC=CC=C1)=O)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 35 | CELSIUS | 8 | HOUR | 17 g of LiCl were dissolved in 250 ml of dimethylformamide in a 2 l stirred flask fitted with internal thermometer and condenser. A solution of 86 g of ethyl trimethylbenzoylphenylphosphinate in 50 ml of DMF was subsequently added dropwise over the course of one hour. The reaction mixture was subsequently stirred overn... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccccc1 | Other | CN(C)C=O.CN(C=O)C | 35 | 8 | CCOP(=O)(C(=O)c1ccccc1)c1ccc(C)c(C)c1C>CN(C)C=O.CN(C=O)C>Cc1ccc(P(=O)(O)C(=O)c2ccccc2)c(C)c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-030534b377084e57912edf9db45eb7b3 | O=C(Cl)c1ccccc1.Oc1cccc(O)c1O>>O=C(Oc1cccc(OC(=O)c2ccccc2)c1OC(=O)c1ccccc1)c1ccccc1 | C(C1=CC=CC=C1)(=O)Cl.C1(O)=C(O)C(O)=CC=C1.C(Cl)Cl>>C(C1=CC=CC=C1)(=O)OC1=C(OC(C2=CC=CC=C2)=O)C(OC(C2=CC=CC=C2)=O)=CC=C1 | Cl[C:10](=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.[OH:1][c:22]1[cH:5][cH:6][cH:7][c:8]([OH:9])[c:18]1[OH:19]>>[O:1]=[C:2]([O:3][c:4]1[cH:5][cH:6][cH:7][c:8]([O:9][C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]1[O:19][C:20](=[O:21])[c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)[c:28]1[cH:29][c... | O=C(Cl)c1ccccc1.Oc1cccc(O)c1O | O=C(Oc1cccc(OC(=O)c2ccccc2)c1OC(=O)c1ccccc1)c1ccccc1 | null | null | O1CCCC1.C(C)N(CC)CC | Aromatic Heterocycle Formation | OtherReaction | 5ead06fcad3730c2a7059893419e903c07a7260975c6703a15635d407d116c98 | a4519aec2a3965d12b0770f99020d1617b310cb21381c460b8a7d5b996e055e9 | O=C(Oc1cccc(OC(=O)c2ccccc2)c1OC(=O)c1ccccc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[OH;D1;+0:6]-[c;H0;D3;+0:7]1:[c:8](-[OH;D1;+0:9]):[c:10]:[c:11]:[cH;D2;+0:12]:[c;H0;D3;+0:13]:1-[OH;D1;+0:14]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[O;H0;D2;+0:9]-[c:8]1:[c:10]:[c:11]:[cH;D2;+0:12]:[c:15](-[#8:16]-[C:17](=[O;H0;D1;+0:14])-[c:18]):[c;H0;D3;+0:7]:1-[O;H0;D2;+0:6... | null | [] | null | null | 15 | MINUTE | A 500 ml three-necked round-bottom flask equipped with a magnetic stirrer was charged with 20.0 g (0.142 mol) of benzoyl chloride, 6.2 g (0.05 mol) of pyrogallol, 400 ml of methylene chloride, and 50 ml of tetrahydrofuran (THF). Triethylamine (TEA; 15.3 g, 0.15 mol) was added drop-wise via an addition funnel over a per... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic alcohol.Aromatic alcohol.Aromatic alcohol | Ester.Ester.Ester | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | O1CCCC1.C(C)N(CC)CC | null | 0.25 | O=C(Cl)c1ccccc1.Oc1cccc(O)c1O>O1CCCC1.C(C)N(CC)CC>O=C(Oc1cccc(OC(=O)c2ccccc2)c1OC(=O)c1ccccc1)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-48bfca0e2b574456be37ba3257838937 | CCOC(CCCCl)OCC.OCCO>>CCOC(CCCOCCO)OCC | CC(C)([O-])C.[K+].C(C)(C)(C)O.C(C)OC(CCCCl)OCC.C(CO)O>>C(C)OC(CCCOCCO)OCC | Cl[CH2:7][CH2:6][CH2:5][CH:4]([O:3][CH2:2][CH3:1])[O:12][CH2:13][CH3:14].[OH:8][CH2:9][CH2:10][OH:11]>>[CH3:1][CH2:2][O:3][CH:4]([CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][OH:11])[O:12][CH2:13][CH3:14] | CCOC(CCCCl)OCC.OCCO | CCOC(CCCOCCO)OCC | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | null | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[C:4]-[C:5]-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[C:2]-[C:3] | null | [] | null | null | null | null | A mixture of anhydrous ethylene glycol (120 g, 1.93 moles), a 1.0M solution of potassium tert-butoxide in tert-butanol (70 ml, 0.07 moles), and 4-chlorobutyraldehyde diethyl acetal (11 g, 0.061 moles) is stirred overnight at 100° C. under an argon atmosphere. After cooling to room temperature, the reaction mixture is a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | null | HCl | null | null | null | CCOC(CCCCl)OCC.OCCO>>CCOC(CCCOCCO)OCC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9e41983dcaff4233809d182e77ca4890 | CC(C=O)CCCl.CCOC(OCC)OCC>>CCOC(OCC)C(C)CCCl | ClCCC(C=O)C.C(OCC)(OCC)OCC.C(=O)([O-])[O-].[Na+].[Na+]>>C(C)OC(C(CCCl)C)OCC | [O:3]=[CH:4][CH:8]([CH3:9])[CH2:10][CH2:11][Cl:12].CCOC(O[CH2:2][CH3:1])[O:5][CH2:6][CH3:7]>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[CH:8]([CH3:9])[CH2:10][CH2:11][Cl:12] | CC(C=O)CCCl.CCOC(OCC)OCC | CCOC(OCC)C(C)CCCl | null | O.C1(=CC=C(C=C1)S(=O)(=O)O)C | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | fcd88c7abf874cee525e2d08e112aab4759e77ad93b33f36b8306c7913ea31c2 | 11306b4f2dea9cefbc3d550c8afb389271a44b7cc69c06172e6b191dd38b2284 | null | C-C-O-C(-O-[CH2;D2;+0:1]-[C;D1;H3:2])-[O;H0;D2;+0:3]-[C:4]-[C;D1;H3:5].[C:6]-[C:7](-[C;D1;H3:8])-[CH;D2;+0:9]=[O;H0;D1;+0:10]>>[C:6]-[C:7](-[C;D1;H3:8])-[CH;D3;+0:9](-[O;H0;D2;+0:10]-[CH2;D2;+0:1]-[C;D1;H3:2])-[O;H0;D2;+0:3]-[C:4]-[C;D1;H3:5] | 41.1 | [{"value": 41.1, "product": "C(C)OC(C(CCCl)C)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 45 | CELSIUS | 8 | HOUR | A mixture of 4-chloro-2-methylbutyraldehyde (4.8 g, 0.040 moles), triethyl orthoformate (6.48 g, 0.044 moles), ethyl alcohol (3.0 g), and p-toluenesulfonic acid monohydrate (0.0144 g, 0.000757 moles) was stirred at 45° C. overnight under an argon atmosphere. Next, after cooling to room temperature, Na2CO3 (0.40 g) was ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ether.Ether.Ether | Ether.Ether | null | null | null | HO- | O.C1(=CC=C(C=C1)S(=O)(=O)O)C.C(C)O | 45 | 8 | CC(C=O)CCCl.CCOC(OCC)OCC>O.C1(=CC=C(C=C1)S(=O)(=O)O)C.C(C)O>CCOC(OCC)C(C)CCCl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-818c2b18a9904f71addd77ccaff06faa | CCOc1cc([C@@H](CCN)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC.CS(=O)(=O)Cl>>CCOc1cc([C@@H](CCNS(C)(=O)=O)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC | NCC[C@H](C1=CC(=C(C=C1)OC)OCC)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1.C(C)N(CC)CC.CS(=O)(=O)Cl>>C(C)OC=1C=C(C=CC1OC)[C@@H](CCNS(=O)(=O)C)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1 | [CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([C@@H:7]([CH2:8][CH2:9][NH2:10])[N:15]2[CH2:16][c:17]3[cH:18][cH:19][cH:20][c:21]([NH:22][C:23](=[O:24])[CH:25]4[CH2:26][CH2:27]4)[c:28]3[C:29]2=[O:30])[cH:31][cH:32][c:33]1[O:34][CH3:35].Cl[S:11]([CH3:12])(=[O:13])=[O:14]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([C@@H:7]([CH2:8][CH2:9... | CCOc1cc([C@@H](CCN)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC.CS(=O)(=O)Cl | CCOc1cc([C@@H](CCNS(C)(=O)=O)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC | null | null | C(Cl)Cl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C(Nc1cccc2c1C(=O)N(Cc1ccccc1)C2)C1CC1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 58 | [{"value": 58.0, "product": "C(C)OC=1C=C(C=CC1OC)[C@@H](CCNS(=O)(=O)C)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.0, "product": "C(C)OC=1C=C(C=CC1OC)[C@@H](CCNS(=O)(=O)C)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of (1R)-cyclopropanecarboxylic acid {2-[3-amino-1-(3-ethoxy-4-methoxy-phenyl)-propyl]-3-oxo-2,3-dihydro-1H-isoindol-4-yl}-amide (0.45 g, 1.1 mmol) and triethylamine (0.3 mL, 2 mmol) in methylene chloride (10 mL) was added methane sulfonyl chloride (0.10 mL, 1.3 mmol) at 0° C. After 3 hrs, the mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1CC1 | HCl | C(Cl)Cl | null | 3 | CCOc1cc([C@@H](CCN)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC.CS(=O)(=O)Cl>C(Cl)Cl>CCOc1cc([C@@H](CCNS(C)(=O)=O)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e114af13a5664142ab148ad5dbb787a4 | CCOc1cc([C@@H](CCO)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC.C[S-]>>CCOc1cc([C@@H](CCS(C)(=O)=O)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC | C[S-].[Na+].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.CC(C)OC(=O)/N=N/C(=O)OC(C)C.OOS(=O)[O-].[K+].C(C)OC=1C=C(C=CC1OC)[C@@H](CCO)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1>>C(C)OC=1C=C(C=CC1OC)[C@@H](CCS(=O)(=O)C)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1 | O[CH2:9][CH2:8][C@H:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:32]([O:33][CH3:34])[cH:31][cH:30]1)[N:14]1[CH2:15][c:16]2[cH:17][cH:18][cH:19][c:20]([NH:21][C:22](=[O:23])[CH:24]3[CH2:25][CH2:26]3)[c:27]2[C:28]1=[O:29].[S-:10][CH3:11]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([C@@H:7]([CH2:8][CH2:9][S:10]([CH3:11])(=[O:12]... | CCOc1cc([C@@H](CCO)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC.C[S-] | CCOc1cc([C@@H](CCS(C)(=O)=O)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC | null | null | O.CO.C1CCOC1 | Oxidation | OtherReaction | 73c2476c41c8515bdf0b3d2d5312a722954623c3e1b9a0ddee21ff22e742c5e0 | 3a3ab12dec04b19634fa8823ab0bdcabaf2d96b4725cd4b9c2c5c991f82bbe88 | O=C(Nc1cccc2c1C(=O)N(Cc1ccccc1)C2)C1CC1 | O-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[S-;H0;D1:5]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D4;+0:5](-[C;D1;H3:4])(=[O;D1;H0:6])=[O;D1;H0:7] | 5 | [{"value": 5.0, "product": "C(C)OC=1C=C(C=CC1OC)[C@@H](CCS(=O)(=O)C)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 4.7, "product": "C(C)OC=1C=C(C=CC1OC)[C@@H](CCS(=O)(=O)C)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of triphenyl phosphine (0.63 g, 2.4 mmol) in THF (10 mL) was added DIAD (0.47 mL, 2.4 mmol) at 0° C. After 10 min, (1R)-cyclopropanecarboxylic acid {2-[1-(3-ethoxy-4-methoxy-phenyl)-3-hydroxy-propyl]-3-oxo-2,3-dihydro-1H-isoindol-4-yl}-amide (0.93 mL, 2.2 mmol) was added as solid. After 5 min, sodium thio... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Sulfone | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1CC1 | HO- | O.CO.C1CCOC1 | null | 0.166667 | CCOc1cc([C@@H](CCO)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC.C[S-]>O.CO.C1CCOC1>CCOc1cc([C@@H](CCS(C)(=O)=O)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-925812fbbb324d949ef5d7cd58b72cd1 | CC(=O)OC(C)=O.CCOc1cc([C@@H](CC(=O)NO)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC>>CCOc1cc([C@@H](CC(=O)NOC(C)=O)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC | C(C)OC=1C=C(C=CC1OC)[C@@H](CC(NO)=O)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1.C(C)(=O)OC(C)=O.CCOCC.CCCCCC>>C(C)(=O)ONC(=O)C[C@H](C1=CC(=C(C=C1)OC)OCC)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1 | CC(=O)O[C:13]([CH3:14])=[O:15].[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([C@@H:7]([CH2:8][C:9](=[O:10])[NH:11][OH:12])[N:16]2[CH2:17][c:18]3[cH:19][cH:20][cH:21][c:22]([NH:23][C:24](=[O:25])[CH:26]4[CH2:27][CH2:28]4)[c:29]3[C:30]2=[O:31])[cH:32][cH:33][c:34]1[O:35][CH3:36]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([C@@H:7]([CH2... | CC(=O)OC(C)=O.CCOc1cc([C@@H](CC(=O)NO)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC | CCOc1cc([C@@H](CC(=O)NOC(C)=O)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC | null | null | C(C)#N.C(Cl)Cl | Acylation | Acetic anhydride and alcohol to ester | 868ba94f028b30e9347f1568001d166d126ab48ad34862bd252bb72f87967edd | 93289da630dbaf2d9339c4212dcd342dfbcc29df4e79a63418a0fd9f589abdc1 | O=C(Nc1cccc2c1C(=O)N(Cc1ccccc1)C2)C1CC1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5](=[O;D1;H0:6])-[#7:7]-[OH;D1;+0:8]>>[C:4]-[C:5](=[O;D1;H0:6])-[#7:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | 63 | [{"value": 63.0, "product": "C(C)(=O)ONC(=O)C[C@H](C1=CC(=C(C=C1)OC)OCC)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of (1R)-cyclopropanecarboxylic acid {2-[1-(3-ethoxy-4-methoxy-phenyl)-2-hydroxycarbamoyl-ethyl]-3-oxo-2,3-dihydro-1H-isoindol-4-yl}-amide and acetic anhydride (0.09 mL, 1 mmol) in acetonitrile/methylene chloride (6 mL each) was stirred at room temperature for 21 hrs. Ether (10 mL) and hexane (10 mL) was adde... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | null | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1CC1 | HO- | C(C)#N.C(Cl)Cl | null | null | CC(=O)OC(C)=O.CCOc1cc([C@@H](CC(=O)NO)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC>C(C)#N.C(Cl)Cl>CCOc1cc([C@@H](CC(=O)NOC(C)=O)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f4d0726dc9104a07b868c8c7b3d871d7 | CC(O)=S.CCOc1cc([C@@H](CCO)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC>>CCOc1cc([C@@H](CCSC(C)=O)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC | C(C)OC=1C=C(C=CC1OC)[C@@H](CCO)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)(=S)O.CC(C)OC(=O)/N=N/C(=O)OC(C)C>>C1(CC1)C(=O)NC=1C=CC=C2CN(C(C12)=O)[C@H](CCSC(C)=O)C1=CC(=C(C=C1)OC)OCC | [S:10]=[C:11]([CH3:12])[OH:13].O[CH2:9][CH2:8][C@H:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:32]([O:33][CH3:34])[cH:31][cH:30]1)[N:14]1[CH2:15][c:16]2[cH:17][cH:18][cH:19][c:20]([NH:21][C:22](=[O:23])[CH:24]3[CH2:25][CH2:26]3)[c:27]2[C:28]1=[O:29]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([C@@H:7]([CH2:8][CH2:9][S:10][C:... | CC(O)=S.CCOc1cc([C@@H](CCO)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC | CCOc1cc([C@@H](CCSC(C)=O)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC | null | null | CO.C1CCOC1 | Acylation | OtherReaction | f0ef48ecf2991802b01fab2c99f81aa4ec5b243bec9eedcaaebf72a3cffee580 | e483c239103a312878e017a96b05cdd3919bff7fb9afe11e6eb3dea046fbf05c | O=C(Nc1cccc2c1C(=O)N(Cc1ccccc1)C2)C1CC1 | O-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[C;H0;D3;+0:5](-[OH;D1;+0:6])=[S;H0;D1;+0:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:7]-[C;H0;D3;+0:5](-[C;D1;H3:4])=[O;H0;D1;+0:6] | 81.3 | [{"value": 79.0, "product": "C1(CC1)C(=O)NC=1C=CC=C2CN(C(C12)=O)[C@H](CCSC(C)=O)C1=CC(=C(C=C1)OC)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.3, "product": "C1(CC1)C(=O)NC=1C=CC=C2CN(C(C12)=O)[C@H](CCSC(C)=O)C1=CC(=C(C=C1)OC)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a solution of (1R)-cyclopropanecarboxylic acid {2-[1-(3-ethoxy-4-methoxy-phenyl)-3-hydroxy-propyl]-3-oxo-2,3-dihydro-1H-isoindol-4-yl}-amide (5.7 g, 13 mmol), triphenyl phosphine (7.1 g, 2.4 mmol) and thioacetic acid (2.2 mL, 31 mmol) in THF (50 mL) was added a solution of DIAD (5.5 mL, 28 mmol) in THF (50 mL) at ro... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Thiocarbonyl | Carbo-thioester | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1CC1 | HO- | CO.C1CCOC1 | null | 4 | CC(O)=S.CCOc1cc([C@@H](CCO)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC>CO.C1CCOC1>CCOc1cc([C@@H](CCSC(C)=O)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-87d8d94fcf83444bbd3e044f1f4cf88b | CCOc1cc([C@@H](CC(=O)OC)N2Cc3c(Cl)ccc(NC(=O)C4CC4)c3C2=O)ccc1OC>>CCOc1cc([C@@H](CC(=O)O)N2Cc3c(Cl)ccc(NC(=O)C4CC4)c3C2=O)ccc1OC | O.COC(C[C@H](C1=CC(=C(C=C1)OC)OCC)N1C(C2=C(C=CC(=C2C1)Cl)NC(=O)C1CC1)=O)=O.[OH-].[Na+]>>ClC1=C2CN(C(C2=C(C=C1)NC(=O)C1CC1)=O)[C@H](CC(=O)O)C1=CC(=C(C=C1)OC)OCC | C[O:11][C:9]([CH2:8][C@H:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:31]([O:32][CH3:33])[cH:30][cH:29]1)[N:12]1[CH2:13][c:14]2[c:15]([Cl:16])[cH:17][cH:18][c:19]([NH:20][C:21](=[O:22])[CH:23]3[CH2:24][CH2:25]3)[c:26]2[C:27]1=[O:28])=[O:10]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([C@@H:7]([CH2:8][C:9](=[O:10])[OH:11])[N:1... | CCOc1cc([C@@H](CC(=O)OC)N2Cc3c(Cl)ccc(NC(=O)C4CC4)c3C2=O)ccc1OC | CCOc1cc([C@@H](CC(=O)O)N2Cc3c(Cl)ccc(NC(=O)C4CC4)c3C2=O)ccc1OC | null | null | C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(Nc1cccc2c1C(=O)N(Cc1ccccc1)C2)C1CC1 | 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] | 99 | [{"value": 99.0, "product": "ClC1=C2CN(C(C2=C(C=C1)NC(=O)C1CC1)=O)[C@H](CC(=O)O)C1=CC(=C(C=C1)OC)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.5, "product": "ClC1=C2CN(C(C2=C(C=C1)NC(=O)C1CC1)=O)[C@H](CC(=O)O)C1=CC(=C(C=C1)OC)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of (3R)-3-[4-chloro-7-(cyclopropanecarbonyl-amino)-1-oxo-1,3-dihydro-isoindol-2-yl]-3-(3-ethoxy-4-methoxy-phenyl)-propionic acid methyl ester (3.0 g, 6.2 mmol) in THF (60 ml) was added NaOH (10N, 1.2 ml, 12 mmol). The mixture was stirred at room temperature overnight. To it was added water (50 ml). The mi... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1CC1 | Other | C1CCOC1 | null | 8 | CCOc1cc([C@@H](CC(=O)OC)N2Cc3c(Cl)ccc(NC(=O)C4CC4)c3C2=O)ccc1OC>C1CCOC1>CCOc1cc([C@@H](CC(=O)O)N2Cc3c(Cl)ccc(NC(=O)C4CC4)c3C2=O)ccc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3dc33e4cf89b4bbb81fb1c9dcf78860d | CCOc1cc([C@@H](CC(=O)O)N2Cc3c(Cl)ccc(NC(=O)C4CC4)c3C2=O)ccc1OC.[NH4+]>>CCOc1cc([C@@H](CC(N)=O)N2Cc3c(Cl)ccc(NC(=O)C4CC4)c3C2=O)ccc1OC | O.[NH4+].[OH-].ClC1=C2CN(C(C2=C(C=C1)NC(=O)C1CC1)=O)[C@H](CC(=O)O)C1=CC(=C(C=C1)OC)OCC.C(=O)(N1C=NC=C1)N1C=NC=C1>>C(N)(=O)C[C@H](C1=CC(=C(C=C1)OC)OCC)N1CC2=C(C=CC(=C2C1=O)NC(=O)C1CC1)Cl | O[C:9]([CH2:8][C@H:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:31]([O:32][CH3:33])[cH:30][cH:29]1)[N:12]1[CH2:13][c:14]2[c:15]([Cl:16])[cH:17][cH:18][c:19]([NH:20][C:21](=[O:22])[CH:23]3[CH2:24][CH2:25]3)[c:26]2[C:27]1=[O:28])=[O:11].[NH4+:10]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([C@@H:7]([CH2:8][C:9]([NH2:10])=[O:11]... | CCOc1cc([C@@H](CC(=O)O)N2Cc3c(Cl)ccc(NC(=O)C4CC4)c3C2=O)ccc1OC.[NH4+] | CCOc1cc([C@@H](CC(N)=O)N2Cc3c(Cl)ccc(NC(=O)C4CC4)c3C2=O)ccc1OC | null | null | C1CCOC1 | Acylation | Carboxylic acid to amide conversion | 1283aef55d7ee699f097a8e5267689198c76ba671644401547f902657820236d | cb0a71c3fb37a76e96fbd81aae6f95a28398a03d1ad2c8e877085e735efb98f1 | O=C(Nc1cccc2c1C(=O)N(Cc1ccccc1)C2)C1CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH4+;D0:5]>>[C:4]-[C:3]-[C;H0;D3;+0:1](-[NH2;D1;+0:5])=[O;D1;H0:2] | 82 | [{"value": 82.0, "product": "C(N)(=O)C[C@H](C1=CC(=C(C=C1)OC)OCC)N1CC2=C(C=CC(=C2C1=O)NC(=O)C1CC1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.5, "product": "C(N)(=O)C[C@H](C1=CC(=C(C=C1)OC)OCC)N1CC2=C(C=CC(=C2C1=O)NC(=O)C1CC1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of (3R)-3-[4-chloro-7-(cyclopropanecarbonyl-amino)-1-oxo-1,3-dihydro-isoindol-2-yl]-3-(3-ethoxy-4-methoxy-phenyl)-propionic acid (0.62 g, 1.3 mmol) in THF (5 ml) was added carbonyldiimidazole (0.3 g, 2 mmol) at room temperature. The solution was stirred for 2 hrs at room temperature. To the mixture was ad... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1CC1 | HO- | C1CCOC1 | null | 2 | CCOc1cc([C@@H](CC(=O)O)N2Cc3c(Cl)ccc(NC(=O)C4CC4)c3C2=O)ccc1OC.[NH4+]>C1CCOC1>CCOc1cc([C@@H](CC(N)=O)N2Cc3c(Cl)ccc(NC(=O)C4CC4)c3C2=O)ccc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9a32770b12d242688e83be9915a73828 | CCOc1cc([C@@H](CC(=O)O)N2Cc3c(Cl)ccc(NC(=O)C4CC4)c3C2=O)ccc1OC.CNC>>CCOc1cc([C@@H](CC(=O)N(C)C)N2Cc3c(Cl)ccc(NC(=O)C4CC4)c3C2=O)ccc1OC | O.CNC.ClC1=C2CN(C(C2=C(C=C1)NC(=O)C1CC1)=O)[C@H](CC(=O)O)C1=CC(=C(C=C1)OC)OCC.C(=O)(N1C=NC=C1)N1C=NC=C1>>ClC=1C=CC(=C2C(N(CC12)[C@H](CC(N(C)C)=O)C1=CC(=C(C=C1)OC)OCC)=O)NC(=O)C1CC1 | O[C:9]([CH2:8][C@H:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:33]([O:34][CH3:35])[cH:32][cH:31]1)[N:14]1[CH2:15][c:16]2[c:17]([Cl:18])[cH:19][cH:20][c:21]([NH:22][C:23](=[O:24])[CH:25]3[CH2:26][CH2:27]3)[c:28]2[C:29]1=[O:30])=[O:10].[NH:11]([CH3:12])[CH3:13]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([C@@H:7]([CH2:8][C:9](... | CCOc1cc([C@@H](CC(=O)O)N2Cc3c(Cl)ccc(NC(=O)C4CC4)c3C2=O)ccc1OC.CNC | CCOc1cc([C@@H](CC(=O)N(C)C)N2Cc3c(Cl)ccc(NC(=O)C4CC4)c3C2=O)ccc1OC | null | null | O1CCCC1.C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(Nc1cccc2c1C(=O)N(Cc1ccccc1)C2)C1CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:6](-[C;D1;H3:5])-[C;D1;H3:7] | 77 | [{"value": 77.0, "product": "ClC=1C=CC(=C2C(N(CC12)[C@H](CC(N(C)C)=O)C1=CC(=C(C=C1)OC)OCC)=O)NC(=O)C1CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.9, "product": "ClC=1C=CC(=C2C(N(CC12)[C@H](CC(N(C)C)=O)C1=CC(=C(C=C1)OC)OCC)=O)NC(=O)C1CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of (3R)-3-[4-chloro-7-(cyclopropanecarbonyl-amino)-1-oxo-1,3-dihydro-isoindol-2-yl]-3-(3-ethoxy-4-methoxy-phenyl)-propionic acid (0.62 g, 1.3 mmol) in tetrahydrofurane (5 ml) was added carbonyldiimidazole (0.3 g, 2 mmol) at room temperature. The solution was stirred for 2 hours at room temperature. To the... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1CC1 | HO- | O1CCCC1.C1CCOC1 | null | 2 | CCOc1cc([C@@H](CC(=O)O)N2Cc3c(Cl)ccc(NC(=O)C4CC4)c3C2=O)ccc1OC.CNC>O1CCCC1.C1CCOC1>CCOc1cc([C@@H](CC(=O)N(C)C)N2Cc3c(Cl)ccc(NC(=O)C4CC4)c3C2=O)ccc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d329915687724e97ab7ee1dc630b449d | CC(=O)OC(C)=O.CCOc1cc(C(CC(=O)NO)N2Cc3c(Cl)ccc(NC(=O)C4CC4)c3C2=O)ccc1OC>>CCOc1cc([C@@H](CC(=O)NOC(C)=O)N2Cc3c(Cl)ccc(NC(=O)C4CC4)c3C2=O)ccc1OC | ClC=1C=CC(=C2C(N(CC12)C(CC(NO)=O)C1=CC(=C(C=C1)OC)OCC)=O)NC(=O)C1CC1.C(C)(=O)OC(C)=O>>C(C)(=O)ONC(=O)C[C@H](C1=CC(=C(C=C1)OC)OCC)N1CC2=C(C=CC(=C2C1=O)NC(=O)C1CC1)Cl | CC(=O)O[C:13]([CH3:14])=[O:15].[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][C:9](=[O:10])[NH:11][OH:12])[N:16]2[CH2:17][c:18]3[c:19]([Cl:20])[cH:21][cH:22][c:23]([NH:24][C:25](=[O:26])[CH:27]4[CH2:28][CH2:29]4)[c:30]3[C:31]2=[O:32])[cH:33][cH:34][c:35]1[O:36][CH3:37]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([C@@H:7... | CC(=O)OC(C)=O.CCOc1cc(C(CC(=O)NO)N2Cc3c(Cl)ccc(NC(=O)C4CC4)c3C2=O)ccc1OC | CCOc1cc([C@@H](CC(=O)NOC(C)=O)N2Cc3c(Cl)ccc(NC(=O)C4CC4)c3C2=O)ccc1OC | null | null | CC#N | Acylation | Acetic anhydride and alcohol to ester | 868ba94f028b30e9347f1568001d166d126ab48ad34862bd252bb72f87967edd | 93289da630dbaf2d9339c4212dcd342dfbcc29df4e79a63418a0fd9f589abdc1 | O=C(Nc1cccc2c1C(=O)N(Cc1ccccc1)C2)C1CC1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5](=[O;D1;H0:6])-[#7:7]-[OH;D1;+0:8]>>[C:4]-[C:5](=[O;D1;H0:6])-[#7:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | 80 | [{"value": 80.0, "product": "C(C)(=O)ONC(=O)C[C@H](C1=CC(=C(C=C1)OC)OCC)N1CC2=C(C=CC(=C2C1=O)NC(=O)C1CC1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 0.8, "product": "C(C)(=O)ONC(=O)C[C@H](C1=CC(=C(C=C1)OC)OCC)N1CC2=C(C=CC(=C2C1=O)NC(=O)C1CC1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": fa... | null | null | 8 | HOUR | To the solution of cyclopropanecarboxylic acid {7-chloro-2-[1-(3-ethoxy-4-methoxy-phenyl)-2-hydroxycarbamoyl-ethyl]-3-oxo-2,3-dihydro-1H-isoindol-4-yl}-amide (0.45 g, 92 mmol) in CH3CN (50 ml) was added acetic anhydride (0.1 ml, 92 mmol) at room temperature. The mixture was stirred overnight. The solvent was removed in... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | null | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1CC1 | HO- | CC#N | null | 8 | CC(=O)OC(C)=O.CCOc1cc(C(CC(=O)NO)N2Cc3c(Cl)ccc(NC(=O)C4CC4)c3C2=O)ccc1OC>CC#N>CCOc1cc([C@@H](CC(=O)NOC(C)=O)N2Cc3c(Cl)ccc(NC(=O)C4CC4)c3C2=O)ccc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c85b56030ec24ab7859c0b64fedd09e1 | CCOc1cc(C(CC)N2Cc3cccc(N)c3C2=O)ccc1OC.O=C(Cl)C1CC1>>CCOc1cc(C(CC)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC | NC=1C=CC=C2CN(C(C12)=O)C(CC)C1=CC(=C(C=C1)OC)OCC.C1(CC1)C(=O)Cl>>C(C)OC=1C=C(C=CC1OC)C(CC)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1 | [CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][CH3:9])[N:10]2[CH2:11][c:12]3[cH:13][cH:14][cH:15][c:16]([NH2:17])[c:23]3[C:24]2=[O:25])[cH:26][cH:27][c:28]1[O:29][CH3:30].Cl[C:18](=[O:19])[CH:20]1[CH2:21][CH2:22]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH:7]([CH2:8][CH3:9])[N:10]2[CH2:11][c:12]3[cH:13][cH:14][cH:1... | CCOc1cc(C(CC)N2Cc3cccc(N)c3C2=O)ccc1OC.O=C(Cl)C1CC1 | CCOc1cc(C(CC)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC | null | null | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1cccc2c1C(=O)N(Cc1ccccc1)C2)C1CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5]-1.[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH2;D1;+0:11]):[c:12]>>[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5]-1):[c:12] | 76 | [{"value": 76.0, "product": "C(C)OC=1C=C(C=CC1OC)C(CC)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.0, "product": "C(C)OC=1C=C(C=CC1OC)C(CC)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 7-amino-2-[1-(3-ethoxy-4-methoxy-phenyl)-propyl]-2,3-dihydro-isoindol-1-one (1.0 g, 2.9 mmol) and cyclopropanecarbonyl chloride (0.32 mL, 3.5 mmol) in THF (10 mL) was heated to reflux for 40 min. The solvent was removed in vacuo. The residue was extracted with ethyl acetate (50 mL) and sodium hydrogen car... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1CC1 | HCl | C1CCOC1 | null | null | CCOc1cc(C(CC)N2Cc3cccc(N)c3C2=O)ccc1OC.O=C(Cl)C1CC1>C1CCOC1>CCOc1cc(C(CC)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3976d1dd1f7b491f96647de6073f7480 | CCOc1cc(C(N)CC#N)ccc1OC.COC(=O)c1c(NC(=O)C2CC2)ccc(Cl)c1CBr>>CCOCOc1cccc(C(CC#N)N2Cc3c(Cl)ccc(NC(=O)C4CC4)c3C2=O)c1 | NC(CC#N)C1=CC(=C(C=C1)OC)OCC.CCN(CC)CC.CN(C)C=O.COC(C1=C(C(=CC=C1NC(=O)C1CC1)Cl)CBr)=O>>ClC=1C=CC(=C2C(N(CC12)C(CC#N)C1=CC(=CC=C1)OCOCC)=O)NC(=O)C1CC1 | CO[c:7]1[c:6]([O:5][CH2:4][CH3:1])[cH:32][c:10]([CH:11]([CH2:12][C:13]#[N:14])[NH2:15])[cH:9][cH:8]1.Br[CH2:16][c:17]1[c:18]([Cl:19])[cH:20][cH:21][c:22]([NH:23][C:24](=[O:25])[CH:26]2[CH2:27][CH2:28]2)[c:29]1[C:30]([O:3][CH3:2])=[O:31]>>[CH3:1][CH2:2][O:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10]([CH:11]([CH2:12][C:1... | CCOc1cc(C(N)CC#N)ccc1OC.COC(=O)c1c(NC(=O)C2CC2)ccc(Cl)c1CBr | CCOCOc1cccc(C(CC#N)N2Cc3c(Cl)ccc(NC(=O)C4CC4)c3C2=O)c1 | null | null | null | Acylation | OtherReaction | 4dc04163e7329c0e3dde9858b4978420350f21786689364e833cc493caf76728 | 6e0f9a634ba6dd4c9e55d394504b7f16316998fe7a9a5315cc45c1f13a1e08e4 | O=C(Nc1cccc2c1C(=O)N(Cc1ccccc1)C2)C1CC1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4](-[C;H0;D3;+0:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-[CH3;D1;+0:8]):[c:9].C-O-[c;H0;D3;+0:10]1:[c:11]:[c:12]:[c:13](-[C:14](-[C:15])-[NH2;D1;+0:16]):[c:17]:[c:18]:1-[#8:19]-[CH2;D2;+0:20]-[CH3;D1;+0:21]>>[C:15]-[C:14](-[N;H0;D3;+0:16]1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4](:[c:9])-[C;H0;D3;+0:5... | 80 | [{"value": 80.0, "product": "ClC=1C=CC(=C2C(N(CC12)C(CC#N)C1=CC(=CC=C1)OCOCC)=O)NC(=O)C1CC1", "details": "PERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | To the DMF solution (20 ml) of 3-Amino-3-(3-ethoxy-4-methoxy-phenyl)-propionitrile (1.55 g, 7 mmol) was added Et3N (1.6 ml, 12 mmol) followed by 2-bromomethyl-3-chloro-6-(cyclopropanecarbonyl-amino)-benzoic acid methyl ester (2.42 g, 7 mmol). The mixture was heated at 90° C. for 12 hrs then cooled to room temperature. ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ether.Ether.Primary amine | Ether.Ether.Tertiary amide | c1ccccc1 | c1ccccc1.c1ccc2c(c1)C[NH]C2 | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1CC1 | HBr | null | 90 | null | CCOc1cc(C(N)CC#N)ccc1OC.COC(=O)c1c(NC(=O)C2CC2)ccc(Cl)c1CBr>>CCOCOc1cccc(C(CC#N)N2Cc3c(Cl)ccc(NC(=O)C4CC4)c3C2=O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4fdf1970698b41ccb5a1fe4c0d1cb73b | CCOc1cc(C(O)Cc2c(Cl)cncc2Cl)ccc1OC.COC(=O)c1c(CBr)cccc1NC(=O)C1CC1.[N-]=[N+]=NP(=O)(Oc1ccccc1)Oc1ccccc1>>CCOc1cc(C(Cc2c(Cl)cncc2Cl)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC | P(=O)(OC1=CC=CC=C1)(OC1=CC=CC=C1)N=[N+]=[N-].COC(C1=C(C=CC=C1NC(=O)C1CC1)CBr)=O.C(C)N(CC)CC.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.ClC=1C=NC=C(C1CC(O)C1=CC(=C(C=C1)OC)OCC)Cl.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.CC(C)OC(=O)/N=N/C(=O)OC(C)C>>ClC=1C=NC=C(C1CC(C1=CC(=C(C=C1)OC)OCC)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1)Cl | O[CH:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:35]([O:36][CH3:37])[cH:34][cH:33]1)[CH2:8][c:9]1[c:10]([Cl:11])[cH:12][n:13][cH:14][c:15]1[Cl:16].CO[C:31]([c:30]1[c:19]([CH2:18]Br)[cH:20][cH:21][cH:22][c:23]1[NH:24][C:25](=[O:26])[CH:27]1[CH2:28][CH2:29]1)=[O:32].[N-]=[N+]=[N:17]P(=O)(Oc1ccccc1)Oc1ccccc1>>[CH3:1][CH2:... | CCOc1cc(C(O)Cc2c(Cl)cncc2Cl)ccc1OC.COC(=O)c1c(CBr)cccc1NC(=O)C1CC1.[N-]=[N+]=NP(=O)(Oc1ccccc1)Oc1ccccc1 | CCOc1cc(C(Cc2c(Cl)cncc2Cl)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC | null | null | O.CN(C)C=O | Acylation | OtherReaction | 17fe2a646dd4de7be7c73b0f0f788f2660943a11d725759f95a025a85d7b5e8e | 1022b08b499a2b7b58105a2a4c3d4c284074a167b9477694ec9de4904f40da19 | O=C(Nc1cccc2c1C(=O)N(C(Cc1ccncc1)c1ccccc1)C2)C1CC1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4](-[C;H0;D3;+0:5](=[O;D1;H0:6])-O-C):[c:7].O-[CH;D3;+0:8](-[C:9]-[c:10])-[c:11](:[c:12]):[c:13].O=P(-O-c1:c:c:c:c:c:1)(-O-c1:c:c:c:c:c:1)-[N;H0;D2;+0:14]=[N+]=[N-]>>[O;D1;H0:6]=[C;H0;D3;+0:5]1-[N;H0;D3;+0:14](-[CH;D3;+0:8](-[C:9]-[c:10])-[c:11](:[c:12]):[c:13])-[CH2;D2;+0:1]-[c:2](:[c... | 37.6 | [{"value": 16.0, "product": "ClC=1C=NC=C(C1CC(C1=CC(=C(C=C1)OC)OCC)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 37.6, "product": "ClC=1C=NC=C(C1CC(C1=CC(=C(C=C1)OC)OCC)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To a mixture of 2-(3,5-dichloro-pyridin-4-yl)-1-(3-ethoxy-4-methoxy-phenyl)-ethanol (500 mg, 1.5 mmol) and PPh3 (0.60 g, 2.3 mmol), was added DIAD (0.44 mL, 2.2 mmol) at 0° C. After 5 min, (PhO)2PON3 was added to the mixture at 0° C. The mixture was allowed to warm to room temperature overnight. To the mixture was adde... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Azide.Secondary alcohol | Tertiary amide | c1ccccc1.c1ccccc1 | c1ccc2c(c1)C[NH]C2 | c1ccccc1.c1ccncc1.c1ccc2c(c1)C[NH]C2.C1CC1 | HBr | O.CN(C)C=O | null | 0.083333 | CCOc1cc(C(O)Cc2c(Cl)cncc2Cl)ccc1OC.COC(=O)c1c(CBr)cccc1NC(=O)C1CC1.[N-]=[N+]=NP(=O)(Oc1ccccc1)Oc1ccccc1>O.CN(C)C=O>CCOc1cc(C(Cc2c(Cl)cncc2Cl)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7bcfb6f1831f48f6ad8405c07c761485 | CCOc1cc([C@@H](CC(C)=O)NC(=O)OC(C)(C)C)ccc1OC>>CCOc1cc([C@@H](CC(C)(C)O)NC(=O)OC(C)(C)C)ccc1OC | CO.C(C)(C)(C)OC(N[C@H](CC(C)=O)C1=CC(=C(C=C1)OC)OCC)=O.C[Li]>>C(C)(C)(C)OC(N[C@H](CC(C)(C)O)C1=CC(=C(C=C1)OC)OCC)=O | [CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([C@@H:7]([CH2:8][C:9]([CH3:10])=[O:12])[NH:13][C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[cH:21][cH:22][c:23]1[O:24][CH3:25]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([C@@H:7]([CH2:8][C:9]([CH3:10])([CH3:11])[OH:12])[NH:13][C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3... | CCOc1cc([C@@H](CC(C)=O)NC(=O)OC(C)(C)C)ccc1OC | CCOc1cc([C@@H](CC(C)(C)O)NC(=O)OC(C)(C)C)ccc1OC | null | null | C1CCOC1 | Miscellaneous | OtherReaction | 7e61014f084ef66fe8691c8f1abaf493e11079effe9d87ae329e041d937b8b3a | 8811b4d793f7cfa9f0f1f47a008648edabb54f371f76dfa680dd5b2e1564c6c5 | c1ccccc1 | [C:1]-[C:2]-[C;H0;D3;+0:3](-[C;D1;H3:4])=[O;H0;D1;+0:5]>>[C:1]-[C:2]-[C;H0;D4;+0:3](-[C;D1;H3:4])(-[C;D1;H3:6])-[OH;D1;+0:5] | 14.1 | [{"value": 14.0, "product": "C(C)(C)(C)OC(N[C@H](CC(C)(C)O)C1=CC(=C(C=C1)OC)OCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 14.1, "product": "C(C)(C)(C)OC(N[C@H](CC(C)(C)O)C1=CC(=C(C=C1)OC)OCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of (1R)-[1-(3-ethoxy-4-methoxy-phenyl)-3-oxo-butyl]-carbamic acid tert-butyl ester (1 g, 3 mmol) in THF (10 mL) was added a solution of methyl lithium (4 mL, 3M, 12 mmol) at 0° C. To the mixture was added methanol (5 mL). The residue was extracted with ethyl acetate (50 mL) and NH4Cl (sat, 25 mL). The org... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol | null | null | c1ccccc1 | Other | C1CCOC1 | null | null | CCOc1cc([C@@H](CC(C)=O)NC(=O)OC(C)(C)C)ccc1OC>C1CCOC1>CCOc1cc([C@@H](CC(C)(C)O)NC(=O)OC(C)(C)C)ccc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-279cb84dce154745ade796a5c6811e57 | CCOc1cc([C@@H](CC(C)(C)O)NC(=O)OC(C)(C)C)ccc1OC.COC(=O)c1c(CBr)cccc1NC(=O)C1CC1>>CCOc1cc([C@@H](CC(C)(C)O)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC | C(C)(C)(C)OC(N[C@H](CC(C)(C)O)C1=CC(=C(C=C1)OC)OCC)=O.Cl.O1CCOCC1.COC(C1=C(C=CC=C1NC(=O)C1CC1)CBr)=O.C(C)N(CC)CC>>C(C)OC=1C=C(C=CC1OC)[C@@H](CC(C)(C)O)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1 | CC(C)(C)OC(=O)[NH:13][C@@H:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:31]([O:32][CH3:33])[cH:30][cH:29]1)[CH2:8][C:9]([CH3:10])([CH3:11])[OH:12].CO[C:27]([c:26]1[c:15]([CH2:14]Br)[cH:16][cH:17][cH:18][c:19]1[NH:20][C:21](=[O:22])[CH:23]1[CH2:24][CH2:25]1)=[O:28]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([C@@H:7]([CH2:8][C... | CCOc1cc([C@@H](CC(C)(C)O)NC(=O)OC(C)(C)C)ccc1OC.COC(=O)c1c(CBr)cccc1NC(=O)C1CC1 | CCOc1cc([C@@H](CC(C)(C)O)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC | null | null | CN(C)C=O.C(Cl)Cl | Acylation | OtherReaction | 8d3a576bbad8b203660cb623061baae446cf7dcda648c93ca927812a5f25b0a4 | 11c1fc9e7ec5f7f1b168da75293a4a03845ac71a6f022e86c9acc90d71c88932 | O=C(Nc1cccc2c1C(=O)N(Cc1ccccc1)C2)C1CC1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4](-[C;H0;D3;+0:5](=[O;D1;H0:6])-O-C):[c:7].C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:8]-[C:9](-[C:10])-[c:11]>>[C:10]-[C:9](-[c:11])-[N;H0;D3;+0:8]1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4](:[c:7])-[C;H0;D3;+0:5]-1=[O;D1;H0:6] | 52.6 | [{"value": 51.0, "product": "C(C)OC=1C=C(C=CC1OC)[C@@H](CC(C)(C)O)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.6, "product": "C(C)OC=1C=C(C=CC1OC)[C@@H](CC(C)(C)O)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 2 | HOUR | To a solution of (1R)-[1-(3-ethoxy-4-methoxy-phenyl)-3-hydroxy-3-methyl-butyl]-carbamic acid tert-butyl ester (150 mg, 0.42 mmol) in methylene chloride (5 mL) was added a solution of HCl in dioxane (0.5 mL, 4N, 2 mmol). After 2 hrs, the solvent was removed and the crude oil was used in the next step without further pur... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbamic ester.Ester.Ether.Boc | Tertiary amide | null | c1ccc2c(c1)C[NH]C2 | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1CC1 | HBr | CN(C)C=O.C(Cl)Cl | 80 | 2 | CCOc1cc([C@@H](CC(C)(C)O)NC(=O)OC(C)(C)C)ccc1OC.COC(=O)c1c(CBr)cccc1NC(=O)C1CC1>CN(C)C=O.C(Cl)Cl>CCOc1cc([C@@H](CC(C)(C)O)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-714a164337ba44a3909e41ae253a7f4d | CCOc1cc([C@@H](CC(=O)NO)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC.O=C(Cl)C1CC1>>CCOc1cc([C@@H](CC(=O)NOC(=O)C2CC2)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC | C(C)OC=1C=C(C=CC1OC)[C@@H](CC(NO)=O)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1.C1(CC1)C(=O)Cl>>C1(CC1)C(=O)ONC(=O)C[C@H](C1=CC(=C(C=C1)OC)OCC)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1 | [CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([C@@H:7]([CH2:8][C:9](=[O:10])[NH:11][OH:12])[N:18]2[CH2:19][c:20]3[cH:21][cH:22][cH:23][c:24]([NH:25][C:26](=[O:27])[CH:28]4[CH2:29][CH2:30]4)[c:31]3[C:32]2=[O:33])[cH:34][cH:35][c:36]1[O:37][CH3:38].Cl[C:13](=[O:14])[CH:15]1[CH2:16][CH2:17]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([... | CCOc1cc([C@@H](CC(=O)NO)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC.O=C(Cl)C1CC1 | CCOc1cc([C@@H](CC(=O)NOC(=O)C2CC2)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC | null | null | C(C)#N | Acylation | Schotten-Baumann to ester | 179ae8baa325b2dace7c965a68a4b2b7e91bea49291f7cdbcd29e5947f465078 | edbcca52d877d662e04f0d6de1a7107a8eca1d366ee6da0d92e37eb02a291876 | O=C(C[C@H](c1ccccc1)N1Cc2cccc(NC(=O)C3CC3)c2C1=O)NOC(=O)C1CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5]-1.[C:6]-[C:7](=[O;D1;H0:8])-[#7:9]-[OH;D1;+0:10]>>[C:6]-[C:7](=[O;D1;H0:8])-[#7:9]-[O;H0;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5]-1 | 66.2 | [{"value": 66.0, "product": "C1(CC1)C(=O)ONC(=O)C[C@H](C1=CC(=C(C=C1)OC)OCC)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.2, "product": "C1(CC1)C(=O)ONC(=O)C[C@H](C1=CC(=C(C=C1)OC)OCC)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | null | null | null | null | To a solution of (1R)-cyclopropanecarboxylic acid {2-[1-(3-ethoxy-4-methoxy-phenyl)-2-hydroxycarbamoyl-ethyl]-3-oxo-2,3-dihydro-1H-isoindol-4-yl}-amide (500 mg, 1.1 mmol) in acetonitrile (5 mL) was added cyclopropanecarbonyl chloride (0.15 mL, 1.7 mmol) at room temperature and kept for 24 his. The solution was extracte... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | null | null | null | c1ccccc1.C1CC1.c1ccc2c(c1)C[NH]C2.C1CC1 | HCl | C(C)#N | null | null | CCOc1cc([C@@H](CC(=O)NO)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC.O=C(Cl)C1CC1>C(C)#N>CCOc1cc([C@@H](CC(=O)NOC(=O)C2CC2)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e5e5a5f5c1d84ed78397c558656bcc2a | CC(C)C(=O)Cl.CCOc1cc([C@@H](CC(=O)NO)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC>>CCOc1cc([C@@H](CC(=O)NOC(=O)C(C)C)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC | C(C)OC=1C=C(C=CC1OC)[C@@H](CC(NO)=O)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1.C(C(C)C)(=O)Cl>>C(C)OC=1C=C(C=CC1OC)[C@@H](CC(NOC(C(C)C)=O)=O)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1 | Cl[C:13](=[O:14])[CH:15]([CH3:16])[CH3:17].[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([C@@H:7]([CH2:8][C:9](=[O:10])[NH:11][OH:12])[N:18]2[CH2:19][c:20]3[cH:21][cH:22][cH:23][c:24]([NH:25][C:26](=[O:27])[CH:28]4[CH2:29][CH2:30]4)[c:31]3[C:32]2=[O:33])[cH:34][cH:35][c:36]1[O:37][CH3:38]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([... | CC(C)C(=O)Cl.CCOc1cc([C@@H](CC(=O)NO)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC | CCOc1cc([C@@H](CC(=O)NOC(=O)C(C)C)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC | null | null | C(C)#N | Acylation | Schotten-Baumann to ester | 179ae8baa325b2dace7c965a68a4b2b7e91bea49291f7cdbcd29e5947f465078 | edbcca52d877d662e04f0d6de1a7107a8eca1d366ee6da0d92e37eb02a291876 | O=C(Nc1cccc2c1C(=O)N(Cc1ccccc1)C2)C1CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[C;D1;H3:5].[C:6]-[C:7](=[O;D1;H0:8])-[#7:9]-[OH;D1;+0:10]>>[C:6]-[C:7](=[O;D1;H0:8])-[#7:9]-[O;H0;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[C;D1;H3:5] | 66 | [{"value": 66.0, "product": "C(C)OC=1C=C(C=CC1OC)[C@@H](CC(NOC(C(C)C)=O)=O)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.0, "product": "C(C)OC=1C=C(C=CC1OC)[C@@H](CC(NOC(C(C)C)=O)=O)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": fal... | null | null | 24 | HOUR | To a solution of (1R)-cyclopropanecarboxylic acid {2-[1-(3-ethoxy-4-methoxy-phenyl)-2-hydroxycarbamoyl-ethyl]-3-oxo-2,3-dihydro-1H-isoindol-4-yl}-amide (500 mg, 1.1 mmol) in acetonitrile (5 mL) was added isobutyryl chloride (0.15 mL, 1.4 mmol) at room temperature and kept for 24 hrs. The solution was extracted with eth... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | null | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1CC1 | HCl | C(C)#N | null | 24 | CC(C)C(=O)Cl.CCOc1cc([C@@H](CC(=O)NO)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC>C(C)#N>CCOc1cc([C@@H](CC(=O)NOC(=O)C(C)C)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4980211a640449fda09187ead7da7f56 | CC(C)(C)C(=O)Cl.CCOc1cc([C@@H](CC(=O)NO)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC>>CCOc1cc([C@@H](CC(=O)NOC(=O)C(C)(C)C)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC | C(C)OC=1C=C(C=CC1OC)[C@@H](CC(NO)=O)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1.CC(C(=O)Cl)(C)C>>CC(C(=O)ONC(=O)C[C@H](C1=CC(=C(C=C1)OC)OCC)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1)(C)C | Cl[C:13](=[O:14])[C:15]([CH3:16])([CH3:17])[CH3:18].[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([C@@H:7]([CH2:8][C:9](=[O:10])[NH:11][OH:12])[N:19]2[CH2:20][c:21]3[cH:22][cH:23][cH:24][c:25]([NH:26][C:27](=[O:28])[CH:29]4[CH2:30][CH2:31]4)[c:32]3[C:33]2=[O:34])[cH:35][cH:36][c:37]1[O:38][CH3:39]>>[CH3:1][CH2:2][O:3][c:4]1[cH:... | CC(C)(C)C(=O)Cl.CCOc1cc([C@@H](CC(=O)NO)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC | CCOc1cc([C@@H](CC(=O)NOC(=O)C(C)(C)C)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC | null | null | C(C)#N | Acylation | Schotten-Baumann to ester | 179ae8baa325b2dace7c965a68a4b2b7e91bea49291f7cdbcd29e5947f465078 | edbcca52d877d662e04f0d6de1a7107a8eca1d366ee6da0d92e37eb02a291876 | O=C(Nc1cccc2c1C(=O)N(Cc1ccccc1)C2)C1CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[C;D1;H3:6].[C:7]-[C:8](=[O;D1;H0:9])-[#7:10]-[OH;D1;+0:11]>>[C:7]-[C:8](=[O;D1;H0:9])-[#7:10]-[O;H0;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[C;D1;H3:6] | 42 | [{"value": 42.0, "product": "CC(C(=O)ONC(=O)C[C@H](C1=CC(=C(C=C1)OC)OCC)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.9, "product": "CC(C(=O)ONC(=O)C[C@H](C1=CC(=C(C=C1)OC)OCC)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired":... | null | null | 24 | HOUR | To a solution of (1R)-cyclopropanecarboxylic acid {2-[1-(3-ethoxy-4-methoxy-phenyl)-2-hydroxycarbamoyl-ethyl]-3-oxo-2,3-dihydro-1H-isoindol-4-yl}-amide (180 mg, 0.4 mmol) in acetonitrile (2 mL) was added 2,2-dimethyl-propionyl chloride (0.064 mL, 0.5 mmol) at room temperature and kept for 24 hrs. The solution was extra... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | null | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1CC1 | HCl | C(C)#N | null | 24 | CC(C)(C)C(=O)Cl.CCOc1cc([C@@H](CC(=O)NO)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC>C(C)#N>CCOc1cc([C@@H](CC(=O)NOC(=O)C(C)(C)C)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9145ba0d3d1842f990d5f4413e0e34d7 | CC(C)(C)CC(=O)Cl.CCOc1cc([C@@H](CC(=O)NO)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC>>CCOc1cc([C@@H](CC(=O)NOC(=O)CC(C)(C)C)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC | C(C)OC=1C=C(C=CC1OC)[C@@H](CC(NO)=O)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1.CC(CC(=O)Cl)(C)C>>CC(CC(=O)ONC(=O)C[C@H](C1=CC(=C(C=C1)OC)OCC)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1)(C)C | Cl[C:13](=[O:14])[CH2:15][C:16]([CH3:17])([CH3:18])[CH3:19].[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([C@@H:7]([CH2:8][C:9](=[O:10])[NH:11][OH:12])[N:20]2[CH2:21][c:22]3[cH:23][cH:24][cH:25][c:26]([NH:27][C:28](=[O:29])[CH:30]4[CH2:31][CH2:32]4)[c:33]3[C:34]2=[O:35])[cH:36][cH:37][c:38]1[O:39][CH3:40]>>[CH3:1][CH2:2][O:3][c... | CC(C)(C)CC(=O)Cl.CCOc1cc([C@@H](CC(=O)NO)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC | CCOc1cc([C@@H](CC(=O)NOC(=O)CC(C)(C)C)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC | null | null | C(C)#N | Acylation | Schotten-Baumann to ester | 179ae8baa325b2dace7c965a68a4b2b7e91bea49291f7cdbcd29e5947f465078 | edbcca52d877d662e04f0d6de1a7107a8eca1d366ee6da0d92e37eb02a291876 | O=C(Nc1cccc2c1C(=O)N(Cc1ccccc1)C2)C1CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6](=[O;D1;H0:7])-[#7:8]-[OH;D1;+0:9]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:9]-[#7:8]-[C:6](-[C:5])=[O;D1;H0:7] | 59.3 | [{"value": 59.0, "product": "CC(CC(=O)ONC(=O)C[C@H](C1=CC(=C(C=C1)OC)OCC)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.3, "product": "CC(CC(=O)ONC(=O)C[C@H](C1=CC(=C(C=C1)OC)OCC)N1CC2=CC=CC(=C2C1=O)NC(=O)C1CC1)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired... | null | null | 24 | HOUR | To a solution of (1R)-cyclopropanecarboxylic acid {2-[1-(3-ethoxy-4-methoxy-phenyl)-2-hydroxycarbamoyl-ethyl]-3-oxo-2,3-dihydro-1H-isoindol-4-yl}-amide (500 mg, 1.1 mmol) in acetonitrile (5 mL) was added 3,3-dimethyl-butyryl chloride (0.2 mL, 1.4 mmol) at room temperature and kept for 24 hrs. The solution was extracted... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | null | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1CC1 | HCl | C(C)#N | null | 24 | CC(C)(C)CC(=O)Cl.CCOc1cc([C@@H](CC(=O)NO)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC>C(C)#N>CCOc1cc([C@@H](CC(=O)NOC(=O)CC(C)(C)C)N2Cc3cccc(NC(=O)C4CC4)c3C2=O)ccc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cf3ec6d5cbfa414cad6175c0d48601e2 | CCOc1cc([C@H](N)CS(C)(=O)=O)ccc1OC.COC(=O)c1c(NC(=O)C2CC2)ccc(F)c1CBr>>CCOc1cc([C@@H](CS(C)(=O)=O)N2Cc3c(F)ccc(NC(=O)C4CC4)c3C2=O)ccc1OC | COC(C1=C(C(=CC=C1NC(=O)C1CC1)F)CBr)=O.CCN(CC)CC.C(C)OC=1C=C(C=CC1OC)[C@@H](CS(=O)(=O)C)N>>C(C)OC=1C=C(C=CC1OC)[C@@H](CS(=O)(=O)C)N1CC2=C(C=CC(=C2C1=O)NC(=O)C1CC1)F | [CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([C@@H:7]([CH2:8][S:9]([CH3:10])(=[O:11])=[O:12])[NH2:13])[cH:30][cH:31][c:32]1[O:33][CH3:34].CO[C:28]([c:27]1[c:15]([CH2:14]Br)[c:16]([F:17])[cH:18][cH:19][c:20]1[NH:21][C:22](=[O:23])[CH:24]1[CH2:25][CH2:26]1)=[O:29]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([C@@H:7]([CH2:8][S:9]([CH3:... | CCOc1cc([C@H](N)CS(C)(=O)=O)ccc1OC.COC(=O)c1c(NC(=O)C2CC2)ccc(F)c1CBr | CCOc1cc([C@@H](CS(C)(=O)=O)N2Cc3c(F)ccc(NC(=O)C4CC4)c3C2=O)ccc1OC | null | null | CN(C)C=O | Acylation | OtherReaction | f2ed1ce250db42124a484193f6bf5adb2cca3d127cf7dd7d17db2ebca43fb4a6 | 0eb062b0407fca631aebf8550994dc507c145d19ea7e1f961f104337865aa8f4 | O=C(Nc1cccc2c1C(=O)N(Cc1ccccc1)C2)C1CC1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4](-[C;H0;D3;+0:5](=[O;D1;H0:6])-O-C):[c:7].[C:8]-[C:9](-[NH2;D1;+0:10])-[c:11]>>[C:8]-[C:9](-[c:11])-[N;H0;D3;+0:10]1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4](:[c:7])-[C;H0;D3;+0:5]-1=[O;D1;H0:6] | 55 | [{"value": 55.0, "product": "C(C)OC=1C=C(C=CC1OC)[C@@H](CS(=O)(=O)C)N1CC2=C(C=CC(=C2C1=O)NC(=O)C1CC1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.4, "product": "C(C)OC=1C=C(C=CC1OC)[C@@H](CS(=O)(=O)C)N1CC2=C(C=CC(=C2C1=O)NC(=O)C1CC1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | To a solution of 2-bromomethyl-6-(cyclopropanecarbonyl-amino)-3-fluoro benzoic acid methyl ester (1 g, 3 mmol) and Et3N (1.25 ml, 9 mmol) in DMF (10 ml) was added (1S)-1-(3-ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethylamine (870 mg, 3.2 mmol). The mixture was heated at 90° C. for 20 hrs. The reaction mixture was coo... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Primary amine | Tertiary amide | null | c1ccc2c(c1)C[NH]C2 | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1CC1 | HBr | CN(C)C=O | 90 | null | CCOc1cc([C@H](N)CS(C)(=O)=O)ccc1OC.COC(=O)c1c(NC(=O)C2CC2)ccc(F)c1CBr>CN(C)C=O>CCOc1cc([C@@H](CS(C)(=O)=O)N2Cc3c(F)ccc(NC(=O)C4CC4)c3C2=O)ccc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fdc6be135f504c58ae490051f303c7e6 | CCOc1cc([C@@H](CS(C)(=O)=O)N2Cc3c(Cl)ccc(N)c3C2=O)ccc1OC.CN(C)C(=O)Cl>>CCOc1cc([C@@H](CS(C)(=O)=O)N2Cc3c(Cl)ccc(NC(=O)N(C)C)c3C2=O)ccc1OC | NC=1C=CC(=C2CN(C(C12)=O)[C@H](CS(=O)(=O)C)C1=CC(=C(C=C1)OC)OCC)Cl.CN(C(=O)Cl)C>>ClC=1C=CC(=C2C(N(CC12)[C@H](CS(=O)(=O)C)C1=CC(=C(C=C1)OC)OCC)=O)NC(N(C)C)=O | [CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([C@@H:7]([CH2:8][S:9]([CH3:10])(=[O:11])=[O:12])[N:13]2[CH2:14][c:15]3[c:16]([Cl:17])[cH:18][cH:19][c:20]([NH2:21])[c:27]3[C:28]2=[O:29])[cH:30][cH:31][c:32]1[O:33][CH3:34].Cl[C:22](=[O:23])[N:24]([CH3:25])[CH3:26]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([C@@H:7]([CH2:8][S:9]([CH3:10]... | CCOc1cc([C@@H](CS(C)(=O)=O)N2Cc3c(Cl)ccc(N)c3C2=O)ccc1OC.CN(C)C(=O)Cl | CCOc1cc([C@@H](CS(C)(=O)=O)N2Cc3c(Cl)ccc(NC(=O)N(C)C)c3C2=O)ccc1OC | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | b81fefae7607aa106605114867756af2924064950a2aea97200543849613e96a | 406c5893488430105533c87dfb5d625d8382e709e047cda9cfdc2235e742a9cf | O=C1c2ccccc2CN1Cc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C;D1;H3:4])-[C;D1;H3:5].[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH2;D1;+0:11]):[c:12]>>[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C;D1;H3:4])-[C;D1;H3:5]):[c:12] | 70 | [{"value": 70.0, "product": "ClC=1C=CC(=C2C(N(CC12)[C@H](CS(=O)(=O)C)C1=CC(=C(C=C1)OC)OCC)=O)NC(N(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | To (1S)-7-amino-4-chloro-2-[1-(3-ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethyl]-2,3-dihydro-isoindol-1-one (800 mg, 1.82 mmol) was added dimethylcarbamyl chloride (3 ml). The mixture was heated at 100° C. for 20 hrs. The reaction mixture was cooled to room temperature and extracted with water (50 ml) and EtOAc (50 m... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Primary amine | Urea | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HCl | null | 100 | null | CCOc1cc([C@@H](CS(C)(=O)=O)N2Cc3c(Cl)ccc(N)c3C2=O)ccc1OC.CN(C)C(=O)Cl>>CCOc1cc([C@@H](CS(C)(=O)=O)N2Cc3c(Cl)ccc(NC(=O)N(C)C)c3C2=O)ccc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-96e2fdaed3064625b0bd3ac8861e4da1 | C1COCCN1.CCOc1cc([C@@H](CS(C)(=O)=O)N2Cc3c(Cl)ccc(NC(=O)CCl)c3C2=O)ccc1OC>>CCOc1cc([C@@H](CS(C)(=O)=O)N2Cc3c(Cl)ccc(NC(=O)CN4CCOCC4)c3C2=O)ccc1OC | Cl.ClCC(=O)NC1=C2C(N(CC2=C(C=C1)Cl)[C@H](CS(=O)(=O)C)C1=CC(=C(C=C1)OC)OCC)=O.N1CCOCC1>>ClC=1C=CC(=C2C(N(CC12)[C@H](CS(=O)(=O)C)C1=CC(=C(C=C1)OC)OCC)=O)NC(CN1CCOCC1)=O | [NH:25]1[CH2:26][CH2:27][O:28][CH2:29][CH2:30]1.Cl[CH2:24][C:22]([NH:21][c:20]1[cH:19][cH:18][c:16]([Cl:17])[c:15]2[c:31]1[C:32](=[O:33])[N:13]([C@@H:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:36]([O:37][CH3:38])[cH:35][cH:34]1)[CH2:8][S:9]([CH3:10])(=[O:11])=[O:12])[CH2:14]2)=[O:23]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c... | C1COCCN1.CCOc1cc([C@@H](CS(C)(=O)=O)N2Cc3c(Cl)ccc(NC(=O)CCl)c3C2=O)ccc1OC | CCOc1cc([C@@H](CS(C)(=O)=O)N2Cc3c(Cl)ccc(NC(=O)CN4CCOCC4)c3C2=O)ccc1OC | null | null | CCOCC.CC#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 2bad30dcdb0a20edb8ce877f072b133eedfd870621da393ec393128bfee00977 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CN1CCOCC1)Nc1cccc2c1C(=O)N(Cc1ccccc1)C2 | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5].[#8:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[O;D1;H0:3]=[C:2](-[#7:4]-[c:5])-[CH2;D2;+0:1]-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#8:6]-[C:11]-[C:10]-1 | null | [] | 70 | CELSIUS | null | null | To a solution of (1S)-2-chloro-N-{7-chloro-2-[1-(3-ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethyl]-3-oxo-2,3-dihydro-1H-isoindol-4-yl}-acetamide (250 mg, 0.48 mmol) in CH3CN (10 ml) was added morpholine (0.17 ml, 1.94 mmol). The mixture was heated at 70° C. for 2 hrs. The reaction mixture was concentrated on rota-vap... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1COCCN1 | C1COCC[NH]1 | c1ccccc1.c1ccc2c(c1)C[NH]C2.C1COCC[NH]1 | HCl | CCOCC.CC#N | 70 | null | C1COCCN1.CCOc1cc([C@@H](CS(C)(=O)=O)N2Cc3c(Cl)ccc(NC(=O)CCl)c3C2=O)ccc1OC>CCOCC.CC#N>CCOc1cc([C@@H](CS(C)(=O)=O)N2Cc3c(Cl)ccc(NC(=O)CN4CCOCC4)c3C2=O)ccc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-47e9caf23e8c45d0b15319b1c2a3af5e | CCOc1cc([C@@H](CS(C)(=O)=O)N2Cc3c(Cl)ccc(NC(=O)CCl)c3C2=O)ccc1OC.CNC>>CCOc1cc([C@@H](CS(C)(=O)=O)N2Cc3c(Cl)ccc(NC(=O)CN(C)C)c3C2=O)ccc1OC | Cl.ClCC(=O)NC1=C2C(N(CC2=C(C=C1)Cl)[C@H](CS(=O)(=O)C)C1=CC(=C(C=C1)OC)OCC)=O.CNC>>ClC=1C=CC(=C2C(N(CC12)[C@H](CS(=O)(=O)C)C1=CC(=C(C=C1)OC)OCC)=O)NC(CN(C)C)=O | Cl[CH2:24][C:22]([NH:21][c:20]1[cH:19][cH:18][c:16]([Cl:17])[c:15]2[c:28]1[C:29](=[O:30])[N:13]([C@@H:7]([c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:33]([O:34][CH3:35])[cH:32][cH:31]1)[CH2:8][S:9]([CH3:10])(=[O:11])=[O:12])[CH2:14]2)=[O:23].[NH:25]([CH3:26])[CH3:27]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([C@@H:7]([CH2:8][S... | CCOc1cc([C@@H](CS(C)(=O)=O)N2Cc3c(Cl)ccc(NC(=O)CCl)c3C2=O)ccc1OC.CNC | CCOc1cc([C@@H](CS(C)(=O)=O)N2Cc3c(Cl)ccc(NC(=O)CN(C)C)c3C2=O)ccc1OC | null | null | CCOCC.CC#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1c2ccccc2CN1Cc1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5].[C;D1;H3:6]-[NH;D2;+0:7]-[C;D1;H3:8]>>[C;D1;H3:6]-[N;H0;D3;+0:7](-[C;D1;H3:8])-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5] | null | [] | 70 | CELSIUS | null | null | To a solution of (1S)-2-chloro-N-{7-chloro-2-[1-(3-ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethyl]-3-oxo-2,3-dihydro-1H-isoindol-4-yl}-acetamide (400 mg, 0.78 mmol) in CH3CN (10 ml) was added dimethylamine (2N in MeOH, 1.6 ml, 3.2 mmol). The mixture was heated at 70° C. for 2 hrs. The reaction mixture was concentrate... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1ccc2c(c1)C[NH]C2 | HCl | CCOCC.CC#N | 70 | null | CCOc1cc([C@@H](CS(C)(=O)=O)N2Cc3c(Cl)ccc(NC(=O)CCl)c3C2=O)ccc1OC.CNC>CCOCC.CC#N>CCOc1cc([C@@H](CS(C)(=O)=O)N2Cc3c(Cl)ccc(NC(=O)CN(C)C)c3C2=O)ccc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ec356710f88d4a4ca9152fbf73a205d2 | NCCCO.O=C(Cl)OCc1ccccc1>>O=C(NCCCO)OCc1ccccc1 | ClC(=O)OCC1=CC=CC=C1.NCCCO>>C(=O)(OCC1=CC=CC=C1)NCCCO | [NH2:3][CH2:4][CH2:5][CH2:6][OH:7].Cl[C:2](=[O:1])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][OH:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1 | NCCCO.O=C(Cl)OCc1ccccc1 | O=C(NCCCO)OCc1ccccc1 | null | null | C(Cl)Cl | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4] | 58.9 | [{"value": 58.9, "product": "C(=O)(OCC1=CC=CC=C1)NCCCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.9, "product": "C(=O)(OCC1=CC=CC=C1)NCCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A CH2Cl2 solution (300 mL) of 3-aminopropanol (10 g, 0.133 mole) and TEA (20 g, 0.2 mole) was cooled to OC, followed by slow addition of CH2Cl2 solution (25 mL) of benzyl chloroformate (25 g, 0.147 mole). The resulting solution was gradually warmed to room temperature. The stirring was continued at room temperature ove... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccccc1 | HCl | C(Cl)Cl | null | 8 | NCCCO.O=C(Cl)OCc1ccccc1>C(Cl)Cl>O=C(NCCCO)OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-41e9fa021b0c4e93a03ef3b4451aa40f | NCCO.O=C(Cl)OCc1ccccc1>>O=C(NCCO)OCc1ccccc1 | NCCO.ClC(=O)OCC1=CC=CC=C1>>C(=O)(OCC1=CC=CC=C1)NCCO | [NH2:3][CH2:4][CH2:5][OH:6].Cl[C:2](=[O:1])[O:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][OH:6])[O:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1 | NCCO.O=C(Cl)OCc1ccccc1 | O=C(NCCO)OCc1ccccc1 | null | null | C(Cl)Cl | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4] | 66 | [{"value": 66.0, "product": "C(=O)(OCC1=CC=CC=C1)NCCO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To 0° C. cold of CH2Cl2 solution (300 mL) of 2-aminoethanol (10.8 g, 0.177 mole) and TEA (26.8 g; 0.265 mole) was added slowly a CH2Cl2 solution (50 mL) of benzyl chloroformate (33.2 g, 0.194 mole). After complete addition, the resulting solution was gradually warmed to room temperature and stirring was continued at ro... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccccc1 | HCl | C(Cl)Cl | null | 8 | NCCO.O=C(Cl)OCc1ccccc1>C(Cl)Cl>O=C(NCCO)OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e70bcd291c9e4b55bba3424621298b37 | COC(C)(C)OC.Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O>>CC1(C)O[C@@H]2[C@H](O1)[C@@H](CO)O[C@H]2n1cnc2c(N)ncnc21 | [OH-].[NH4+].C1(=CC=C(C=C1)S(=O)(=O)O)C.[C@@H]1([C@H](O)[C@H](O)[C@@H](CO)O1)N1C=NC=2C(N)=NC=NC12.COC(C)(C)OC>>CC1(O[C@@H]2[C@H](O[C@H]([C@@H]2O1)N3C=NC4=C3N=CN=C4N)CO)C | CO[C:2](OC)([CH3:1])[CH3:3].[OH:4][C@@H:5]1[C@H:6]([OH:7])[C@@H:8]([CH2:9][OH:10])[O:11][C@H:12]1[n:13]1[cH:14][n:15][c:16]2[c:17]([NH2:18])[n:19][cH:20][n:21][c:22]12>>[CH3:1][C:2]1([CH3:3])[O:4][C@@H:5]2[C@H:6]([O:7]1)[C@@H:8]([CH2:9][OH:10])[O:11][C@H:12]2[n:13]1[cH:14][n:15][c:16]2[c:17]([NH2:18])[n:19][cH:20][n:21... | COC(C)(C)OC.Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O | CC1(C)O[C@@H]2[C@H](O1)[C@@H](CO)O[C@H]2n1cnc2c(N)ncnc21 | null | null | C(Cl)Cl.C(C)O.CC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | a330e69afd5270a4360edf768ff70dadde5800ba102e1d8f75a68e8e628afade | 5b3ed0191ba86b6e1048e761d184b2389fdc2075f66c7c9aaba67c74a6cbc43e | c1ncc2ncn([C@@H]3OC[C@H]4OCO[C@@H]34)c2n1 | C-O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-O-C.[OH;D1;+0:4]-[C:5]1-[C:6]-[#8:7]-[C:8]-[C:9]-1-[OH;D1;+0:10]>>[C;D1;H3:2]-[C;H0;D4;+0:1]1(-[C;D1;H3:3])-[O;H0;D2;+0:4]-[C:5]2-[C:6]-[#8:7]-[C:8]-[C:9]-2-[O;H0;D2;+0:10]-1 | 87.7 | [{"value": 87.7, "product": "CC1(O[C@@H]2[C@H](O[C@H]([C@@H]2O1)N3C=NC4=C3N=CN=C4N)CO)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of p-toluenesulfonic acid (7.79 g, 0.45 mol) in dry acetone (100 ml) is added dropwise to a solution of adenosine (10 g, 0.037 mol) in dry acetone (300 ml). 2,2-Dimethoxypropane (18.18 ml, d=0.847) is then added to the reaction mixture, and the mixture stirred for 48 hours (TLC methylene chloride/ethanol 9:1... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Secondary alcohol.Secondary alcohol | Ether.Ether | null | C1O[C@H]2COC[C@H]2O1 | C1O[C@H]2COC[C@H]2O1.c1ncnc2[nH]cnc12 | HO- | C(Cl)Cl.C(C)O.CC(=O)C | null | null | COC(C)(C)OC.Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O>C(Cl)Cl.C(C)O.CC(=O)C>CC1(C)O[C@@H]2[C@H](O1)[C@@H](CO)O[C@H]2n1cnc2c(N)ncnc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-97bda1e20a6f41ceba71300b911c2899 | CC(=O)Nc1ccccc1.O=S(=O)(O)Cl>>CC(=O)Nc1ccc(S(=O)(=O)Cl)cc1 | ClS(=O)(=O)O.C(C)(=O)NC1=CC=CC=C1>>C(C)(=O)NC1=CC=C(C=C1)S(=O)(=O)Cl | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][cH:13][cH:14]1.O=[S:9]([OH:10])(=[O:11])[Cl:12]>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([S:9](=[O:10])(=[O:11])[Cl:12])[cH:13][cH:14]1 | CC(=O)Nc1ccccc1.O=S(=O)(O)Cl | CC(=O)Nc1ccc(S(=O)(=O)Cl)cc1 | null | null | null | Protection | Aromatic sulfonyl chlorination | c55ee9a7393fdf3f247a23f751c8b9bb8a24c2b053414c59e6d87cc0f6e27124 | c731d053565135be022f3edbe36cf28a9b4364ca579bdb183b2db9578bab4695 | c1ccccc1 | O=[S;H0;D4;+0:1](-[Cl;D1;H0:2])(=[O;D1;H0:3])-[OH;D1;+0:4].[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[Cl;D1;H0:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;H0;D1;+0:4])-[c;H0;D3;+0:7](:[c:6]:[c:5]):[c:8]:[c:9] | 48.3 | [{"value": 48.0, "product": "C(C)(=O)NC1=CC=C(C=C1)S(=O)(=O)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.3, "product": "C(C)(=O)NC1=CC=C(C=C1)S(=O)(=O)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | Chlorosulfonic acid (10 ml, 0.15 mol) is added dropwise slowly to acetanilide (4 g, 0.029 mol). The mixture is then heated to 100° C. for one hour. The oil that forms is cooled and carefully poured onto ice. The resulting precipitate is collected by filtration affording the desired product (3.4 g, 0.014 mol, 48% yield)... | 10.6084/m9.figshare.5104873.v1 | null | null | Sulfonyl halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | null | 100 | null | CC(=O)Nc1ccccc1.O=S(=O)(O)Cl>>CC(=O)Nc1ccc(S(=O)(=O)Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ed8c67e3d1204add98ebb0a1091f6a59 | C1CCNCC1.CC(=O)Nc1ccc(S(=O)(=O)Cl)cc1>>CC(=O)Nc1ccc(S(=O)(=O)N2CCCCC2)cc1 | N1CCCCC1.C(C)(=O)NC1=CC=C(C=C1)S(=O)(=O)Cl>>C(C)(=O)NC1=CC=C(C=C1)S(=O)(=O)N1CCCCC1 | [NH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1.Cl[S:9]([c:8]1[cH:7][cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[cH:19][cH:18]1)(=[O:10])=[O:11]>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([S:9](=[O:10])(=[O:11])[N:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[cH:18][cH:19]1 | C1CCNCC1.CC(=O)Nc1ccc(S(=O)(=O)Cl)cc1 | CC(=O)Nc1ccc(S(=O)(=O)N2CCCCC2)cc1 | null | null | O1CCOCC1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | d63e07b47df62aebedb35134f6d0504cfcbed5ccfdec31c2c42bba6875c15fe7 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=S(=O)(c1ccccc1)N1CCCCC1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6])-[C:10]-[C:11] | 52.14 | [{"value": 52.14, "product": "C(C)(=O)NC1=CC=C(C=C1)S(=O)(=O)N1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | Piperidine (0.0114 Mol) is added to a solution of 4-acetamidophenylsulfonyl chloride (1.34 g, 0.0057 mol) in dioxane (5 mL). The mixture is heated for 1 hour at 80° C., then part of the solvent is removed by evaporation at reduced pressure, and water is added until precipitation of the resulting sulfonamide. The produc... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1 | HCl | O1CCOCC1 | 80 | null | C1CCNCC1.CC(=O)Nc1ccc(S(=O)(=O)Cl)cc1>O1CCOCC1>CC(=O)Nc1ccc(S(=O)(=O)N2CCCCC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-39fdb52fef834638aa3fde6b0ca316a4 | CC(=O)Nc1ccc(S(=O)(=O)Cl)cc1.CCN>>CCNS(=O)(=O)c1ccc(NC(C)=O)cc1 | C(C)N.C(C)(=O)NC1=CC=C(C=C1)S(=O)(=O)Cl>>C(C)NS(=O)(=O)C1=CC=C(C=C1)NC(C)=O | Cl[S:4](=[O:5])(=[O:6])[c:7]1[cH:8][cH:9][c:10]([NH:11][C:12]([CH3:13])=[O:14])[cH:15][cH:16]1.[CH3:1][CH2:2][NH2:3]>>[CH3:1][CH2:2][NH:3][S:4](=[O:5])(=[O:6])[c:7]1[cH:8][cH:9][c:10]([NH:11][C:12]([CH3:13])=[O:14])[cH:15][cH:16]1 | CC(=O)Nc1ccc(S(=O)(=O)Cl)cc1.CCN | CCNS(=O)(=O)c1ccc(NC(C)=O)cc1 | null | null | O1CCOCC1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C;D1;H3:7]-[C:8]-[NH2;D1;+0:9]>>[C;D1;H3:7]-[C:8]-[NH;D2;+0:9]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 48 | [{"value": 48.0, "product": "C(C)NS(=O)(=O)C1=CC=C(C=C1)NC(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | Ethylamine (0.0114 mMol) is added to a solution of 4-acetamidophenylsulfonyl chloride (1.34 g, 0.0057 mol) in dioxane (5 mL). The mixture is stirred for 1 hour at 0° C., then part of the solvent is removed by evaporation at reduced pressure, and water is added until precipitation of the resulting sulfonamide. The produ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1 | HCl | O1CCOCC1 | 0 | 1 | CC(=O)Nc1ccc(S(=O)(=O)Cl)cc1.CCN>O1CCOCC1>CCNS(=O)(=O)c1ccc(NC(C)=O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e4b6fae0c1e54924ac7ce671810fa5b1 | CC(=O)Nc1ccc(S(=O)(=O)Cl)cc1.NC12CC3CC(CC(C3)C1)C2>>CC(=O)Nc1ccc(S(=O)(=O)NC23CC4CC(CC(C4)C2)C3)cc1 | Cl.C12(CC3CC(CC(C1)C3)C2)N.C(C)N(CC)CC.C(C)(=O)NC1=CC=C(C=C1)S(=O)(=O)Cl>>C12(CC3CC(CC(C1)C3)C2)NS(=O)(=O)C2=CC=C(C=C2)NC(C)=O | Cl[S:9]([c:8]1[cH:7][cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[cH:24][cH:23]1)(=[O:10])=[O:11].[NH2:12][C:13]12[CH2:14][CH:15]3[CH2:16][CH:17]([CH2:18][CH:19]([CH2:20]3)[CH2:21]1)[CH2:22]2>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([S:9](=[O:10])(=[O:11])[NH:12][C:13]23[CH2:14][CH:15]4[CH2:16][CH:17]([CH2:18][CH:1... | CC(=O)Nc1ccc(S(=O)(=O)Cl)cc1.NC12CC3CC(CC(C3)C1)C2 | CC(=O)Nc1ccc(S(=O)(=O)NC23CC4CC(CC(C4)C2)C3)cc1 | null | null | O1CCOCC1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=S(=O)(NC12CC3CC(CC(C3)C1)C2)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8](-[NH2;D1;+0:9])(-[C:10])-[C:11]>>[C:7]-[C:8](-[NH;D2;+0:9]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6])(-[C:10])-[C:11] | 30.3 | [{"value": 30.3, "product": "C12(CC3CC(CC(C1)C3)C2)NS(=O)(=O)C2=CC=C(C=C2)NC(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | 1-Adamantanamine hydrochloride (0.0114 mol) and triethylamine (0.0114 mol) are added to a solution of 4-acetamidophenylsulfonyl chloride (1.34 g, 0.0057 mol) in dioxane (5 mL). The mixture is heated for 1 hour at 80° C., then part of the solvent is removed by evaporation at reduced pressure, and water is added until pr... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.C1C2CC3CC1CC(C2)C3 | HCl | O1CCOCC1 | 80 | null | CC(=O)Nc1ccc(S(=O)(=O)Cl)cc1.NC12CC3CC(CC(C3)C1)C2>O1CCOCC1>CC(=O)Nc1ccc(S(=O)(=O)NC23CC4CC(CC(C4)C2)C3)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f5867f0a56f74b5f8f8250f9295bfa78 | CC(=O)Nc1ccc(S(=O)(=O)Cl)cc1.ClCCNCCCl>>CC(=O)Nc1ccc(S(=O)(=O)N(CCCl)CCCl)cc1 | Cl.ClCCNCCCl.C(C)N(CC)CC.C(C)(=O)NC1=CC=C(C=C1)S(=O)(=O)Cl>>ClCCN(S(=O)(=O)C1=CC=C(C=C1)NC(C)=O)CCCl | Cl[S:9]([c:8]1[cH:7][cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[cH:20][cH:19]1)(=[O:10])=[O:11].[NH:12]([CH2:13][CH2:14][Cl:15])[CH2:16][CH2:17][Cl:18]>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([S:9](=[O:10])(=[O:11])[N:12]([CH2:13][CH2:14][Cl:15])[CH2:16][CH2:17][Cl:18])[cH:19][cH:20]1 | CC(=O)Nc1ccc(S(=O)(=O)Cl)cc1.ClCCNCCCl | CC(=O)Nc1ccc(S(=O)(=O)N(CCCl)CCCl)cc1 | null | null | O1CCOCC1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | abeb6d9a0c70fe5baef0a8e555c2cd55ac2317f763ce7a0831775db7a04777d8 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[C:10]-[C:11])-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 40.44 | [{"value": 40.44, "product": "ClCCN(S(=O)(=O)C1=CC=C(C=C1)NC(C)=O)CCCl", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | Bis(2-chloroethyl)amine hydrochloride (0.0114 mol) and triethylamine (0.0114 mol) are added to a solution of 4-acetamidophenylsulfonyl chloride (1.34 g, 0.0057 mol) in dioxane (5 mL). The mixture is heated for 1 hour at 80° C., then part of the solvent is removed by evaporation at reduced pressure, and water is added u... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | null | null | c1ccccc1 | HCl | O1CCOCC1 | 80 | null | CC(=O)Nc1ccc(S(=O)(=O)Cl)cc1.ClCCNCCCl>O1CCOCC1>CC(=O)Nc1ccc(S(=O)(=O)N(CCCl)CCCl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-72f5b3bac1774de1a6a19a42599f80db | CC(=O)Nc1ccc(S(=O)(=O)N2CCCCC2)cc1>>Nc1ccc(S(=O)(=O)N2CCCCC2)cc1 | [OH-].[Na+].C(C)(=O)NC1=CC=C(C=C1)S(=O)(=O)N1CCCCC1.C(C)(=O)OCC.ClCCl>>NC1=CC=C(C=C1)S(=O)(=O)N1CCCCC1 | CC(=O)[NH:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[N:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[cH:15][cH:16]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[N:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[cH:15][cH:16]1 | CC(=O)Nc1ccc(S(=O)(=O)N2CCCCC2)cc1 | Nc1ccc(S(=O)(=O)N2CCCCC2)cc1 | null | null | Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | O=S(=O)(c1ccccc1)N1CCCCC1 | C-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 70.62 | [{"value": 70.62, "product": "NC1=CC=C(C=C1)S(=O)(=O)N1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | N-[4-(Acetylamino)phenylsulfonyl]piperidine (Example 5) was heated at 100° C. in 20% hydrochloric acid (5 mL) for one hour (TLC ethyl acetate/dichloromethane 8:2). The solution is neutralized at 0° C. with NaOH. The precipitate that forms is filtered and recrystallized from methanol/diethyl ether to afford the desired ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ccccc1.C1CC[NH]CC1 | HO- | Cl | null | null | CC(=O)Nc1ccc(S(=O)(=O)N2CCCCC2)cc1>Cl>Nc1ccc(S(=O)(=O)N2CCCCC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ff145d030128435c8c79a13cc1baebb8 | CC(=O)Nc1ccc(S(=O)(=O)NC(C)(C)C)cc1>>CC(C)(C)NS(=O)(=O)c1ccc(N)cc1 | CC(C)(C)NS(=O)(=O)C1=CC=C(C=C1)NC(C)=O.Cl>>CC(C)(C)NS(=O)(=O)C1=CC=C(C=C1)N | CC(=O)[NH:13][c:12]1[cH:11][cH:10][c:9]([S:6]([NH:5][C:2]([CH3:1])([CH3:3])[CH3:4])(=[O:7])=[O:8])[cH:15][cH:14]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][S:6](=[O:7])(=[O:8])[c:9]1[cH:10][cH:11][c:12]([NH2:13])[cH:14][cH:15]1 | CC(=O)Nc1ccc(S(=O)(=O)NC(C)(C)C)cc1 | CC(C)(C)NS(=O)(=O)c1ccc(N)cc1 | null | null | [OH-].[Na+] | Reduction | Hydrogenolysis of amides/imides/carbamates | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | c1ccccc1 | C-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | N-(1,1-Dimethylethyl)-4-(acetylamino)benzenesulfonamide (Example 11) is deprotected by saponification in 20% NaOH (5 mL), followed by neutralization with 10% HCl. The precipitate that is formed is collected by filtration and recrystallized from methanol/diethyl ether.
Conditions: See reaction.notes.procedure_details.
W... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ccccc1 | HO- | [OH-].[Na+] | null | null | CC(=O)Nc1ccc(S(=O)(=O)NC(C)(C)C)cc1>[OH-].[Na+]>CC(C)(C)NS(=O)(=O)c1ccc(N)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a3be8f53c6cd4a76bcc32505f5bb4119 | CCCCCNS(=O)(=O)c1ccc(N)cc1.O=C(Cl)OC(Cl)(Cl)Cl>>CCCCCNS(=O)(=O)c1ccc(N=C=O)cc1 | ClC(=O)OC(Cl)(Cl)Cl.C(CCCC)NS(=O)(=O)C1=CC=C(C=C1)N>>C(CCCC)NS(=O)(=O)C1=CC=C(C=C1)N=C=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][S:7](=[O:8])(=[O:9])[c:10]1[cH:11][cH:12][c:13]([NH2:14])[cH:17][cH:18]1.ClC(Cl)(Cl)O[C:15](Cl)=[O:16]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][S:7](=[O:8])(=[O:9])[c:10]1[cH:11][cH:12][c:13]([N:14]=[C:15]=[O:16])[cH:17][cH:18]1 | CCCCCNS(=O)(=O)c1ccc(N)cc1.O=C(Cl)OC(Cl)(Cl)Cl | CCCCCNS(=O)(=O)c1ccc(N=C=O)cc1 | null | null | C(C)#N | Miscellaneous | OtherReaction | 0ec6a935a6983e4fae956bd32d6b73673d785b0038e180c9eae5047ab134b99e | 316c7f97eb16d487300e41fc15a4cbaed6e03a6a42a6d2f82d728a115ba492af | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-C(-Cl)(-Cl)-Cl.[NH2;D1;+0:3]-[c:4](:[c:5]):[c:6]>>[O;D1;H0:2]=[C;H0;D2;+0:1]=[N;H0;D2;+0:3]-[c:4](:[c:5]):[c:6] | null | [] | 65 | CELSIUS | null | null | Under argon, trichloromethyl chloroformate (135 μL, 1.118 mmol) is added to N-(pentyl)-4-aminobenzenesulfonamide (Example 26, 0.572 mmol) in anhydrous acetonitrile (4 mL). The solution is heated to 65° C. for 5 hours and the solvent removed at reduced pressure. The formation of the isocyanate is confirmed by infrared s... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Trichloro group.Ether.Primary amine | Isocyanate | null | null | c1ccccc1 | HCl | C(C)#N | 65 | null | CCCCCNS(=O)(=O)c1ccc(N)cc1.O=C(Cl)OC(Cl)(Cl)Cl>C(C)#N>CCCCCNS(=O)(=O)c1ccc(N=C=O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-335f8af1e0e84236bd5c51814b3a6896 | O=C(Cl)Oc1ccccc1.c1nnn[nH]1>>O=C(Oc1ccccc1)c1nnn[nH]1 | C1(=CC=CC=C1)OC(=O)Cl.N1N=NN=C1.C(C)N(CC)CC>>O(C1=CC=CC=C1)C(=O)C1=NN=NN1 | Cl[C:2](=[O:1])[O:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1.[cH:10]1[n:11][n:12][n:13][nH:14]1>>[O:1]=[C:2]([O:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[c:10]1[n:11][n:12][n:13][nH:14]1 | O=C(Cl)Oc1ccccc1.c1nnn[nH]1 | O=C(Oc1ccccc1)c1nnn[nH]1 | null | null | null | C-C Coupling | Friedel-Crafts acylation | 3df6429f95e7e078592848cc937facb178eaf0b7ece8152081398760b7c08119 | 25d9bd8621b941df428c033fedc648334f6dc6f4157dff30f33212e6bac7f1de | O=C(Oc1ccccc1)c1nnn[nH]1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[c:4].[#7;a:5]1:[#7;a:6]:[#7;a:7]:[#7;a:8]:[cH;D2;+0:9]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[#8:3]-[c:4])-[c;H0;D3;+0:9]1:[#7;a:5]:[#7;a:6]:[#7;a:7]:[#7;a:8]:1 | null | [] | null | null | 15 | MINUTE | The title compound was prepared according to the procedure described in Tetrahedron Letters, 1977, 1935. Accordingly, phenylchloroformate (6.73 g, 43 mmol) was added dropwise into a solution of tetrazole (42.84 mmol, 3 wt % in 100 mL acetonitrile) containing triethylamine (4.35 g, 43 mmol) at 0° C. The mixture was stir... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether | Ester | c1nnn[nH]1 | c1nnn[nH]1 | c1ccccc1.c1nnn[nH]1 | HCl | null | null | 0.25 | O=C(Cl)Oc1ccccc1.c1nnn[nH]1>>O=C(Oc1ccccc1)c1nnn[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ec8005e4ee6544279e14df239f978c4e | CNC(C)C.O=[N+]([O-])c1ccccc1S(=O)(=O)Cl>>CC(C)N(C)S(=O)(=O)c1ccccc1[N+](=O)[O-] | [N+](=O)([O-])C1=C(C=CC=C1)S(=O)(=O)Cl.C(C)(C)NC.[OH-].[K+]>>C(C)(C)N(S(=O)(=O)C1=C(C=CC=C1)[N+](=O)[O-])C | [CH3:1][CH:2]([CH3:3])[NH:4][CH3:5].Cl[S:6](=[O:7])(=[O:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[N+:15](=[O:16])[O-:17]>>[CH3:1][CH:2]([CH3:3])[N:4]([CH3:5])[S:6](=[O:7])(=[O:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[N+:15](=[O:16])[O-:17] | CNC(C)C.O=[N+]([O-])c1ccccc1S(=O)(=O)Cl | CC(C)N(C)S(=O)(=O)c1ccccc1[N+](=O)[O-] | null | null | O.C1CCOC1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | abeb6d9a0c70fe5baef0a8e555c2cd55ac2317f763ce7a0831775db7a04777d8 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C;D1;H3:7]-[C:8](-[C;D1;H3:9])-[NH;D2;+0:10]-[C;D1;H3:11]>>[C;D1;H3:7]-[C:8](-[C;D1;H3:9])-[N;H0;D3;+0:10](-[C;D1;H3:11])-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | 0 | CELSIUS | null | null | A 250 mL round bottom flask was equipped with a magnetic stirrer. The flask was charged with isopropylmethylamine (0.85 g, 11.6 mmol) followed by THF (50 mL). The mixture was cooled to 0° C. by placing the flask in an ice bath. Potassium hydroxide (23.2 mmol) was dissolved in water (20 mL) and added to the flask. An ad... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | null | null | c1ccccc1 | HCl | O.C1CCOC1 | 0 | null | CNC(C)C.O=[N+]([O-])c1ccccc1S(=O)(=O)Cl>O.C1CCOC1>CC(C)N(C)S(=O)(=O)c1ccccc1[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e3ed68e1e6f14730921c2f5e65b92082 | COc1ccc(N)cc1.O=[N+]([O-])c1ccccc1S(=O)(=O)Cl>>COc1ccc(NS(=O)(=O)c2ccccc2[N+](=O)[O-])cc1 | COC1=CC=C(C=C1)N.S(=O)(=O)(Cl)Cl.S(=O)(=O)(Cl)Cl.C(C)N(CC)CC.[N+](=O)([O-])C1=C(C=CC=C1)S(=O)(=O)Cl>>COC1=CC=C(C=C1)NS(=O)(=O)C1=C(C=CC=C1)[N+](=O)[O-] | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:20][cH:21]1.Cl[S:8](=[O:9])(=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[N+:17](=[O:18])[O-:19]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[N+:17](=[O:18])[O-:19])[cH:20][cH:21]1 | COc1ccc(N)cc1.O=[N+]([O-])c1ccccc1S(=O)(=O)Cl | COc1ccc(NS(=O)(=O)c2ccccc2[N+](=O)[O-])cc1 | null | null | ClCCl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=S(=O)(Nc1ccccc1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | A 250 mL round bottom flask was equipped with a magnetic stirrer, charged with p-anisidine (13.0 mmol), followed by dichloromethane (75 mL). The flask was then placed in an ice bath to chill the contents. Triethylamine was added and an addition funnel was installed. The addition funnel was charged with 2-nitrobenzenesu... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccccc1 | HCl | ClCCl | null | null | COc1ccc(N)cc1.O=[N+]([O-])c1ccccc1S(=O)(=O)Cl>ClCCl>COc1ccc(NS(=O)(=O)c2ccccc2[N+](=O)[O-])cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fab7d2c7618e40eda3cb986d65407eee | CNC(C)C.O=[N+]([O-])c1cccc(S(=O)(=O)Cl)c1>>CC(C)N(C)S(=O)(=O)c1cccc([N+](=O)[O-])c1 | [N+](=O)([O-])C=1C=C(C=CC1)S(=O)(=O)Cl.C(C)(C)NC.[OH-].[K+]>>C(C)(C)N(S(=O)(=O)C1=CC(=CC=C1)[N+](=O)[O-])C | [CH3:1][CH:2]([CH3:3])[NH:4][CH3:5].Cl[S:6](=[O:7])(=[O:8])[c:9]1[cH:10][cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17]1>>[CH3:1][CH:2]([CH3:3])[N:4]([CH3:5])[S:6](=[O:7])(=[O:8])[c:9]1[cH:10][cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17]1 | CNC(C)C.O=[N+]([O-])c1cccc(S(=O)(=O)Cl)c1 | CC(C)N(C)S(=O)(=O)c1cccc([N+](=O)[O-])c1 | null | null | O.C1CCOC1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | abeb6d9a0c70fe5baef0a8e555c2cd55ac2317f763ce7a0831775db7a04777d8 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C;D1;H3:7]-[C:8](-[C;D1;H3:9])-[NH;D2;+0:10]-[C;D1;H3:11]>>[C;D1;H3:7]-[C:8](-[C;D1;H3:9])-[N;H0;D3;+0:10](-[C;D1;H3:11])-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | 0 | CELSIUS | null | null | A 250 mL round bottom flask was equipped with a magnetic stirrer. The flask was charged with isopropylmethylamine (0.85 g, 11.6 mmol) followed by THF (50 mL). The mixture was cooled to 0° C. by placing the flask in an ice bath. Potassium hydroxide (23.2 mmol) was dissolved in water (20 mL) and added to the flask. An ad... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | null | null | c1ccccc1 | HCl | O.C1CCOC1 | 0 | null | CNC(C)C.O=[N+]([O-])c1cccc(S(=O)(=O)Cl)c1>O.C1CCOC1>CC(C)N(C)S(=O)(=O)c1cccc([N+](=O)[O-])c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-50ee35fe8d024b7b9ec747792df57b47 | COc1ccc(N(c2ccc(OC)cc2)S(=O)(=O)c2cccc([N+](=O)[O-])c2)cc1>>COc1ccc(NS(=O)(=O)c2cccc([N+](=O)[O-])c2)cc1 | COC1=CC=C(C=C1)N.[N+](=O)([O-])C=1C=C(C=CC1)S(=O)(=O)Cl.C(C)N(CC)CC.[N+](=O)([O-])C=1C=C(C=CC1)S(=O)(=O)Cl.COC1=CC=C(C=C1)N(S(=O)(=O)C1=CC(=CC=C1)[N+](=O)[O-])C1=CC=C(C=C1)OC.C(C)N(CC)CC>>COC1=CC=C(C=C1)NS(=O)(=O)C1=CC(=CC=C1)[N+](=O)[O-] | COc1ccc([N:7]([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:21][cH:20]2)[S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19]2)[cH:20][cH:21]1 | COc1ccc(N(c2ccc(OC)cc2)S(=O)(=O)c2cccc([N+](=O)[O-])c2)cc1 | COc1ccc(NS(=O)(=O)c2cccc([N+](=O)[O-])c2)cc1 | null | null | ClCCl | Reduction | Hydrogenolysis of tertiary amines | b09e6b17ea76a4247455a547cda036513771365273d513376c372ce0b882f5a3 | 4fdc4ad52053d0e9069bcb21eddebe566bb62c20412a3a19d15116bb45b4ff16 | O=S(=O)(Nc1ccccc1)c1ccccc1 | C-O-c1:c:c:c(-[N;H0;D3;+0:1](-[c:2](:[c:3]):[c:4])-[#16:5](=[O;D1;H0:6])(=[O;D1;H0:7])-[c:8]):c:c:1>>[O;D1;H0:6]=[#16:5](=[O;D1;H0:7])(-[c:8])-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 8 | HOUR | A 250 mL round bottom flask was equipped with a magnetic stirrer. The flask was charged with p-anisidine (13.0 mmol) followed by dichloromethane (50 mL). Triethylamine (25.9 mmol) was added followed by 3-nitrobenzenesulfonyl chloride (16.2 mmol). Additional dichloromethane (75 mL) was added for solubility. The reaction... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Tertiary amine | Sulfonamide | c1ccccc1 | null | c1ccccc1.c1ccccc1 | HO- | ClCCl | null | 8 | COc1ccc(N(c2ccc(OC)cc2)S(=O)(=O)c2cccc([N+](=O)[O-])c2)cc1>ClCCl>COc1ccc(NS(=O)(=O)c2cccc([N+](=O)[O-])c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2ff66529c7c44f218e58a3d166c2114b | CC(C)N(C)S(=O)(=O)c1ccccc1[N+](=O)[O-]>>CC(C)N(C)S(=O)(=O)c1ccccc1N | C(C)(C)N(S(=O)(=O)C1=C(C=CC=C1)[N+](=O)[O-])C.CO.O.NN>>C(C)(C)N(S(=O)(=O)C1=C(C=CC=C1)N)C | O=[N+:15]([O-])[c:14]1[c:9]([S:6]([N:4]([CH:2]([CH3:1])[CH3:3])[CH3:5])(=[O:7])=[O:8])[cH:10][cH:11][cH:12][cH:13]1>>[CH3:1][CH:2]([CH3:3])[N:4]([CH3:5])[S:6](=[O:7])(=[O:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[NH2:15] | CC(C)N(C)S(=O)(=O)c1ccccc1[N+](=O)[O-] | CC(C)N(C)S(=O)(=O)c1ccccc1N | null | [Ni] | ClCCl.C(C)(=O)OCC | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 0 | CELSIUS | null | null | A 250 mL round bottom flask was equipped with a magnetic stirrer and an ice bath. The flask was charged with N-isopropyl-N-methyl-2-nitrobenzenesulfonamide (9.21 mmol), followed by methanol (100 mL). The solution was cooled to 0° C. Hydrazine monohydrate (92.1 mmol) was added, followed by Raney nickel (catalytic amount... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Ni].ClCCl.C(C)(=O)OCC | 0 | null | CC(C)N(C)S(=O)(=O)c1ccccc1[N+](=O)[O-]>[Ni].ClCCl.C(C)(=O)OCC>CC(C)N(C)S(=O)(=O)c1ccccc1N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cef0cfda1ac642a6886b3d0c2d7ae4b0 | O=[N+]([O-])c1ccccc1S(=O)(=O)N1CC=CC1>>Nc1ccccc1S(=O)(=O)N1CC=CC1 | [In].[N+](=O)([O-])C1=C(C=CC=C1)S(=O)(=O)N1CC=CC1.[In].Cl>>N1(CC=CC1)S(=O)(=O)C1=C(N)C=CC=C1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[S:8](=[O:9])(=[O:10])[N:11]1[CH2:12][CH:13]=[CH:14][CH2:15]1>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[S:8](=[O:9])(=[O:10])[N:11]1[CH2:12][CH:13]=[CH:14][CH2:15]1 | O=[N+]([O-])c1ccccc1S(=O)(=O)N1CC=CC1 | Nc1ccccc1S(=O)(=O)N1CC=CC1 | null | null | O.O1CCCC1 | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=S(=O)(c1ccccc1)N1CC=CC1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 24 | HOUR | A 250 mL round bottom flask was equipped with a magnetic stirrer and charged with 1-(2-nitrobenzenesulfonyl)-2,5-dihydro-1H-pyrrole (Example 87, 9.32 mmol, followed by 3:1 water/tetrahydrofuran v/v (50 mL). Indium powder (37.3 mmol) was added, followed by concentrated HCl (55.9 mmol). The reaction gives a slight exothe... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.C1=CC[NH]C1 | Other | O.O1CCCC1 | null | 24 | O=[N+]([O-])c1ccccc1S(=O)(=O)N1CC=CC1>O.O1CCCC1>Nc1ccccc1S(=O)(=O)N1CC=CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5362103fe729464b9b00306f015dd742 | O=[N+]([O-])c1cccc(S(=O)(=O)N2CC=CC2)c1>>Nc1cccc(S(=O)(=O)N2CC=CC2)c1 | [In].[N+](=O)([O-])C=1C=C(C=CC1)S(=O)(=O)N1CC=CC1.[In].Cl>>N1(CC=CC1)S(=O)(=O)C=1C=C(N)C=CC1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[N:10]2[CH2:11][CH:12]=[CH:13][CH2:14]2)[cH:15]1>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[N:10]2[CH2:11][CH:12]=[CH:13][CH2:14]2)[cH:15]1 | O=[N+]([O-])c1cccc(S(=O)(=O)N2CC=CC2)c1 | Nc1cccc(S(=O)(=O)N2CC=CC2)c1 | null | null | O.O1CCCC1 | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=S(=O)(c1ccccc1)N1CC=CC1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 24 | HOUR | A 250 mL round bottom flask was equipped with a magnetic stirrer and charged with 1-(3-nitrobenzenesulfonyl)-2,5-dihydro-1H-pyrrole (Example 92, 9.32 mmol, followed by 3:1 water/tetrahydrofuran v/v (50 mL). Indium powder (37.3 mmol) was added, followed by concentrated HCl (55.9 mmol). The reaction gives a slight exothe... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.C1=CC[NH]C1 | Other | O.O1CCCC1 | null | 24 | O=[N+]([O-])c1cccc(S(=O)(=O)N2CC=CC2)c1>O.O1CCCC1>Nc1cccc(S(=O)(=O)N2CC=CC2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-48f4b00d40744f05b7af700908ef8903 | COc1ccc(C#N)c(N)c1>>COc1ccc2c(N)n[nH]c2c1 | N(=O)[O-].[Na+].NC1=C(C#N)C=CC(=C1)OC>>COC1=CC=C2C(=NNC2=C1)N | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]#[N:8])[c:11]([NH2:10])[cH:12]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([NH2:8])[n:9][nH:10][c:11]2[cH:12]1 | COc1ccc(C#N)c(N)c1 | COc1ccc2c(N)n[nH]c2c1 | null | null | Cl.O | Aromatic Heterocycle Formation | OtherReaction | d9c3df60b021052dd01ef8088447ada9009432bd4057bd33cce465876470c55e | c7c78474f6971eeaa7d180c68d4a8af29cb23110025e531bca1233dc3931475c | c1ccc2[nH]ncc2c1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5](-[NH2;D1;+0:6]):[c:7]>>[NH2;D1;+0:1]-[c;H0;D3;+0:2]1:[#7;a:8]:[nH;D2;+0:6]:[c:5](:[c:7]):[c:3]:1:[c:4] | 91.9 | [{"value": 91.9, "product": "COC1=CC=C2C(=NNC2=C1)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.9, "product": "COC1=CC=C2C(=NNC2=C1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To an ice-cooled suspension of 66.35 g (0.448 mol) of 2-amino-4-methoxybenzonitrile in 530 ml of concentrated HCl, a solution of 37.07 g (0.537 mol) of sodium nitrite in 55 ml of water was added dropwise. After 1.5 hours the cold suspension was added dropwise to a preformed solution of 679.25 g (3.58 mol) of stannous c... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine | Primary amine | c1ccccc1 | c1ccc2n[nH]cc2c1 | c1ccc2n[nH]cc2c1 | Other | Cl.O | null | null | COc1ccc(C#N)c(N)c1>Cl.O>COc1ccc2c(N)n[nH]c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f12aead606f24a7b964da767f75a6aec | COc1ccc2c(N3C(=O)c4ccccc4C3=O)n[nH]c2c1>>O=C1c2ccccc2C(=O)N1c1n[nH]c2cc(O)ccc12 | COC1=CC=C2C(=NNC2=C1)N1C(C2=CC=CC=C2C1=O)=O.Cl.N1=CC=CC=C1.Cl>>OC1=CC=C2C(=NNC2=C1)N1C(C2=CC=CC=C2C1=O)=O | C[O:18][c:17]1[cH:16][c:15]2[nH:14][n:13][c:12]([N:11]3[C:2](=[O:1])[c:3]4[cH:4][cH:5][cH:6][cH:7][c:8]4[C:9]3=[O:10])[c:21]2[cH:20][cH:19]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[c:12]1[n:13][nH:14][c:15]2[cH:16][c:17]([OH:18])[cH:19][cH:20][c:21]12 | COc1ccc2c(N3C(=O)c4ccccc4C3=O)n[nH]c2c1 | O=C1c2ccccc2C(=O)N1c1n[nH]c2cc(O)ccc12 | null | null | C(C)(=O)OCC | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1c2ccccc2C(=O)N1c1n[nH]c2ccccc12 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | 69 | [{"value": 68.9, "product": "OC1=CC=C2C(=NNC2=C1)N1C(C2=CC=CC=C2C1=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.0, "product": "OC1=CC=C2C(=NNC2=C1)N1C(C2=CC=CC=C2C1=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 200 | CELSIUS | null | null | A mixture of 24.2 g (82.5 mmol) of 2-({6-methoxy}-1H-indazol-3-yl)-1H-isoindole-1,3(2H)-dione and 73.4 g (0.635 mol) of piridine hydrochloride was heated at 200° C. for 4 hours. The resulting brown solution was cooled to 140° C. and slowly poured in a well stirred mixture of 250 ml of 0.2 N HCl and 350 ml of ethyl acet... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccc2c(c1)C[NH]C2.c1ccc2n[nH]cc2c1 | Other | C(C)(=O)OCC | 200 | null | COc1ccc2c(N3C(=O)c4ccccc4C3=O)n[nH]c2c1>C(C)(=O)OCC>O=C1c2ccccc2C(=O)N1c1n[nH]c2cc(O)ccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5dcdf5a0b0944f23af127e9d4e22bfa2 | CC(C)(C)[Si](C)(C)Cl.O=C1c2ccccc2C(=O)N1c1n[nH]c2cc(O)ccc12>>CC(C)(C)[Si](C)(C)Oc1ccc2c(N3C(=O)c4ccccc4C3=O)n[nH]c2c1 | OC1=CC=C2C(=NNC2=C1)N1C(C2=CC=CC=C2C1=O)=O.[Si](C)(C)(C(C)(C)C)Cl.N12CCCCCC2=NCCC1>>[Si](C)(C)(C(C)(C)C)OC1=CC=C2C(=NNC2=C1)N1C(C2=CC=CC=C2C1=O)=O | Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][c:9]1[cH:10][cH:11][c:12]2[c:13]([N:14]3[C:15](=[O:16])[c:17]4[cH:18][cH:19][cH:20][cH:21][c:22]4[C:23]3=[O:24])[n:25][nH:26][c:27]2[cH:28]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][c:9]1[cH:10][cH:11][c:12]2[c:13]([N:14]3[C:15](=[O:16]... | CC(C)(C)[Si](C)(C)Cl.O=C1c2ccccc2C(=O)N1c1n[nH]c2cc(O)ccc12 | CC(C)(C)[Si](C)(C)Oc1ccc2c(N3C(=O)c4ccccc4C3=O)n[nH]c2c1 | null | null | Cl.ClCCl | Protection | Alcohol protection with silyl ethers | 91043baed1393f1ecd2302d7d0b31c01cf171d3977dd7c70afa1da52fa298c73 | 4a917c959d011f885a1269fa3c1f022ee5e09144996246d24e42e65634a451ac | O=C1c2ccccc2C(=O)N1c1n[nH]c2ccccc12 | 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].[#7;a:8]:[c:9]:[c:10]:[c:11](-[OH;D1;+0:12]):[c:13]>>[#7;a:8]:[c:9]:[c:10]:[c:11](-[O;H0;D2;+0:12]-[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:13] | 71 | [{"value": 71.0, "product": "[Si](C)(C)(C(C)(C)C)OC1=CC=C2C(=NNC2=C1)N1C(C2=CC=CC=C2C1=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.0, "product": "[Si](C)(C)(C(C)(C)C)OC1=CC=C2C(=NNC2=C1)N1C(C2=CC=CC=C2C1=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | To a suspension of 15.03 g (53.82 mmol) of 2-({6-hydroxy}-1H-indazol-3-yl)-1H-isoindole-1,3(2H)-dione in 150 ml of dichloromethane, a solution of 20.19 g (0.134 mol) of TBDMS chloride in 75 ml of dichloromethane was added. The resulting mixture was treated dropwise with 12.06 ml (80.73 mmol) of 1,8-Diazabicyclo[5.4.0]u... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Silyl protective group | TMS ether protective group | null | null | c1ccc2c(c1)C[NH]C2.c1ccc2n[nH]cc2c1 | HCl | Cl.ClCCl | 50 | null | CC(C)(C)[Si](C)(C)Cl.O=C1c2ccccc2C(=O)N1c1n[nH]c2cc(O)ccc12>Cl.ClCCl>CC(C)(C)[Si](C)(C)Oc1ccc2c(N3C(=O)c4ccccc4C3=O)n[nH]c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-848ed8065e9447ae95d31be90cddff73 | N#Cc1cc(OCc2ccccc2)ccc1N>>Nc1n[nH]c2ccc(OCc3ccccc3)cc12 | N(=O)[O-].[Na+].NC1=C(C#N)C=C(C=C1)OCC1=CC=CC=C1>>C(C1=CC=CC=C1)OC=1C=C2C(=NNC2=CC1)N | [N:1]#[C:2][c:18]1[c:5]([NH2:4])[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17]1>>[NH2:1][c:2]1[n:3][nH:4][c:5]2[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[cH:17][c:18]12 | N#Cc1cc(OCc2ccccc2)ccc1N | Nc1n[nH]c2ccc(OCc3ccccc3)cc12 | null | null | Cl.O | Aromatic Heterocycle Formation | OtherReaction | d9c3df60b021052dd01ef8088447ada9009432bd4057bd33cce465876470c55e | c7c78474f6971eeaa7d180c68d4a8af29cb23110025e531bca1233dc3931475c | c1ccc(COc2ccc3[nH]ncc3c2)cc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5](-[NH2;D1;+0:6]):[c:7]>>[NH2;D1;+0:1]-[c;H0;D3;+0:2]1:[#7;a:8]:[nH;D2;+0:6]:[c:5](:[c:7]):[c:3]:1:[c:4] | 109.4 | [{"value": 109.4, "product": "C(C1=CC=CC=C1)OC=1C=C2C(=NNC2=CC1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To an ice-cooled suspension of 63.27 g (0.282 mol) of 2-amino-5-(benzyloxy)benzonitrile in 500 ml of concentrated hydrochloric acid, a solution of 23.32 g (0.338 mol) of sodium nitrite in 75 ml of water was added dropwise. After 2 hours the cold suspension was added dropwise to a preformed solution of 509.25 g (2.26 mo... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine | Primary amine | c1ccccc1 | c1ccc2n[nH]cc2c1 | c1ccc2n[nH]cc2c1.c1ccccc1 | Other | Cl.O | null | null | N#Cc1cc(OCc2ccccc2)ccc1N>Cl.O>Nc1n[nH]c2ccc(OCc3ccccc3)cc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cb931bc431374d1a867a8f9c572ac897 | O=C1c2ccccc2C(=O)N1c1n[nH]c2ccc(OCc3ccccc3)cc12>>O=C1c2ccccc2C(=O)N1c1n[nH]c2ccc(O)cc12 | C(C1=CC=CC=C1)OC=1C=C2C(=NNC2=CC1)N1C(C2=CC=CC=C2C1=O)=O.Cl.N1=CC=CC=C1>>OC=1C=C2C(=NNC2=CC1)N1C(C2=CC=CC=C2C1=O)=O | c1ccc(C[O:19][c:18]2[cH:17][cH:16][c:15]3[nH:14][n:13][c:12]([N:11]4[C:2](=[O:1])[c:3]5[cH:4][cH:5][cH:6][cH:7][c:8]5[C:9]4=[O:10])[c:21]3[cH:20]2)cc1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[c:12]1[n:13][nH:14][c:15]2[cH:16][cH:17][c:18]([OH:19])[cH:20][c:21]12 | O=C1c2ccccc2C(=O)N1c1n[nH]c2ccc(OCc3ccccc3)cc12 | O=C1c2ccccc2C(=O)N1c1n[nH]c2ccc(O)cc12 | null | null | Cl | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1c2ccccc2C(=O)N1c1n[nH]c2ccccc12 | [c:1]:[c:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4] | 92.4 | [{"value": 92.4, "product": "OC=1C=C2C(=NNC2=CC1)N1C(C2=CC=CC=C2C1=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.4, "product": "OC=1C=C2C(=NNC2=CC1)N1C(C2=CC=CC=C2C1=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 180 | CELSIUS | null | null | A mixture of 46.14 g (0.125 mol) of 2-[5-(benzyloxy)-1H-indazol-3-yl]-1H-isoindole-1,3(2H)-dione and 143.35 g (1.24 mol) of piridine hydrochloride was heated at 180° C. for 1.5 hours. The resulting brown solution was cooled to 120° C. and slowly poured in a well stirred mixture of 800 ml of 0.5 N HCl. The precipitate w... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccc2c(c1)C[NH]C2.c1ccc2n[nH]cc2c1 | Other | Cl | 180 | null | O=C1c2ccccc2C(=O)N1c1n[nH]c2ccc(OCc3ccccc3)cc12>Cl>O=C1c2ccccc2C(=O)N1c1n[nH]c2ccc(O)cc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-39d7897e17fc4837875fe505c7715078 | CC(C)(C)[Si](C)(C)Cl.O=C1c2ccccc2C(=O)N1c1n[nH]c2ccc(O)cc12>>CC(C)(C)[Si](C)(C)Oc1ccc2[nH]nc(N3C(=O)c4ccccc4C3=O)c2c1 | Cl.OC=1C=C2C(=NNC2=CC1)N1C(C2=CC=CC=C2C1=O)=O.[Si](C)(C)(C(C)(C)C)Cl.N12CCCCCC2=NCCC1>>C(C)(C)(C)[Si](OC=1C=C2C(=NNC2=CC1)N1C(C2=CC=CC=C2C1=O)=O)(C)C | Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][c:9]1[cH:10][cH:11][c:12]2[nH:13][n:14][c:15]([N:16]3[C:17](=[O:18])[c:19]4[cH:20][cH:21][cH:22][cH:23][c:24]4[C:25]3=[O:26])[c:27]2[cH:28]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][c:9]1[cH:10][cH:11][c:12]2[nH:13][n:14][c:15]([N:16]3[... | CC(C)(C)[Si](C)(C)Cl.O=C1c2ccccc2C(=O)N1c1n[nH]c2ccc(O)cc12 | CC(C)(C)[Si](C)(C)Oc1ccc2[nH]nc(N3C(=O)c4ccccc4C3=O)c2c1 | null | null | ClCCl | Protection | Alcohol protection with silyl ethers | 91043baed1393f1ecd2302d7d0b31c01cf171d3977dd7c70afa1da52fa298c73 | 4a917c959d011f885a1269fa3c1f022ee5e09144996246d24e42e65634a451ac | O=C1c2ccccc2C(=O)N1c1n[nH]c2ccccc12 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C;D1;H3:5]-[C:4](-[C;D1;H3:6])(-[C;D1;H3:7])-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11] | 79.6 | [{"value": 79.2, "product": "C(C)(C)(C)[Si](OC=1C=C2C(=NNC2=CC1)N1C(C2=CC=CC=C2C1=O)=O)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.6, "product": "C(C)(C)(C)[Si](OC=1C=C2C(=NNC2=CC1)N1C(C2=CC=CC=C2C1=O)=O)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 32.26 g (0.115 mol) of 2-(5-hydroxy-1H-indazol-3-yl)-1H-isoindole-1,3(2H)-dione in 320 ml of dichloromethane, a solution of 43.54 g (0.288 mol) of TBDMS chloride in 150 ml of dichloromethane was added. The resulting mixture was treated dropwise with 35.5 ml (0.23 mol) of 1,8-Diazabicyclo[5.4.0]undec-... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Silyl protective group | TMS ether protective group | null | null | c1ccc2[nH]ncc2c1.c1ccc2c(c1)C[NH]C2 | HCl | ClCCl | null | null | CC(C)(C)[Si](C)(C)Cl.O=C1c2ccccc2C(=O)N1c1n[nH]c2ccc(O)cc12>ClCCl>CC(C)(C)[Si](C)(C)Oc1ccc2[nH]nc(N3C(=O)c4ccccc4C3=O)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-feb837468fb14674a93043c3a885c4ee | CCSc1nc(O)c2c(n1)CCS2.c1ccc(N2CCNCC2)cc1>>Oc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2 | C1(=CC=CC=C1)N1CCNCC1.C(C)SC=1N=C(C2=C(N1)CCS2)O.O>>C1(=CC=CC=C1)N1CCN(CC1)C=1N=C(C2=C(N1)CCS2)O | CCS[c:4]1[n:3][c:2]([OH:1])[c:19]2[c:18]([n:17]1)[CH2:22][CH2:21][S:20]2.[NH:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15][CH2:16]1>>[OH:1][c:2]1[n:3][c:4]([N:5]2[CH2:6][CH2:7][N:8]([c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[CH2:15][CH2:16]2)[n:17][c:18]2[c:19]1[S:20][CH2:21][CH2:22]2 | CCSc1nc(O)c2c(n1)CCS2.c1ccc(N2CCNCC2)cc1 | Oc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2 | null | null | C(C)(=O)O | Heteroatom Alkylation and Arylation | OtherReaction | 5edcaa360f6d7cb70530d2da1a02578ee0e5ea2e1c4c75a8db22a96839feb709 | f5aa33108984aad43441754644c214239e577e2035dc027b4aa13ab85821a21b | c1ccc(N2CCN(c3ncc4c(n3)CCS4)CC2)cc1 | C-C-S-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1):[#7;a:4]:[c:5] | 91.2 | [{"value": 91.0, "product": "C1(=CC=CC=C1)N1CCN(CC1)C=1N=C(C2=C(N1)CCS2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.2, "product": "C1(=CC=CC=C1)N1CCN(CC1)C=1N=C(C2=C(N1)CCS2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 125 | CELSIUS | 1.5 | HOUR | 6.4 g (39 mmol) of N-phenylpiperazine (III) is placed in 2.2 mL of glacial acetic acid, heated to 125° C., then 3.2 g (15 mmol) of 2-ethylsulfanyl-6,7-dihydrothieno[3,2-d]pyrimidin-4-ol (II) is added, and the mixture is heated to 175° C. After 1.5 hours, the resulting solid is stirred with water, suction filtered, wash... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Monosulfide | Tertiary amine | c1ncc2c(n1)CCS2.C1CNCC[NH]1 | C1C[NH]CC[NH]1.c1ncc2c(n1)CCS2 | C1C[NH]CC[NH]1.c1ccccc1.c1ncc2c(n1)CCS2 | Other | C(C)(=O)O | 125 | 1.5 | CCSc1nc(O)c2c(n1)CCS2.c1ccc(N2CCNCC2)cc1>C(C)(=O)O>Oc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e67100e028104d82b6f073f5d26f514b | O=P(Cl)(Cl)Cl.Oc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2>>Clc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2 | C1(=CC=CC=C1)N1CCN(CC1)C=1N=C(C2=C(N1)CCS2)O.P(=O)(Cl)(Cl)Cl>>ClC=1C2=C(N=C(N1)N1CCN(CC1)C1=CC=CC=C1)CCS2 | O=P(Cl)(Cl)[Cl:1].O[c:2]1[n:3][c:4]([N:5]2[CH2:6][CH2:7][N:8]([c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[CH2:15][CH2:16]2)[n:17][c:18]2[c:19]1[S:20][CH2:21][CH2:22]2>>[Cl:1][c:2]1[n:3][c:4]([N:5]2[CH2:6][CH2:7][N:8]([c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[CH2:15][CH2:16]2)[n:17][c:18]2[c:19]1[S:20][CH2:21][CH2:22]... | O=P(Cl)(Cl)Cl.Oc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2 | Clc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2 | null | null | null | Functional Group Interconversion | Alcohol to chloride_POCl3_ortho | 8f305fd901e3bd0073a25a88d9149b63bdb6417de0fa85b75e1ecedc99cc8274 | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1ccc(N2CCN(c3ncc4c(n3)CCS4)CC2)cc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]2:[c:7]:1-[#16:8]-[C:9]-[C:10]-2>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]2:[c:7]:1-[#16:8]-[C:9]-[C:10]-2 | 100 | [{"value": 100.0, "product": "ClC=1C2=C(N=C(N1)N1CCN(CC1)C1=CC=CC=C1)CCS2", "details": "PERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 5 | HOUR | 4.3 g (13.7 mmol) of 2-(4-phenylpiperazin-1-yl)-6,7-dihydrothieno[3,2-d]pyrimidin-4-ol (IV) and 25 mL of phosphorus oxychloride are combined and stirred for 5 hours at 120° C. Excess phosphorus oxychloride is concentrated by evaporation, the residue is combined with ice water and dichloromethane. The organic phase is s... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1ncc2c(n1)CCS2 | c1ncc2c(n1)CCS2 | C1C[NH]CC[NH]1.c1ccccc1.c1ncc2c(n1)CCS2 | HCl | null | 120 | 5 | O=P(Cl)(Cl)Cl.Oc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2>>Clc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a2b6d00b91ba48a797feb875d86c2175 | CCCN.Clc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2>>NCCCc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2 | ClC=1C2=C(N=C(N1)N1CCN(CC1)C1=CC=CC=C1)CCS2.C(CC)N>>C1(=CC=CC=C1)N1CCN(CC1)C=1N=C(C2=C(N1)CCS2)CCCN | [NH2:1][CH2:2][CH2:3][CH3:4].Cl[c:5]1[n:6][c:7]([N:8]2[CH2:9][CH2:10][N:11]([c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[CH2:18][CH2:19]2)[n:20][c:21]2[c:22]1[S:23][CH2:24][CH2:25]2>>[NH2:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]([N:8]2[CH2:9][CH2:10][N:11]([c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[CH2:18][CH2:19]2)[n... | CCCN.Clc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2 | NCCCc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2 | null | null | O | C-C Coupling | OtherReaction | 66e612078539ef51af3d6cc4b27b76a1d47690198f948deef7cf8e23943da07d | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1ccc(N2CCN(c3ncc4c(n3)CCS4)CC2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:1-[#16:7]-[C:8]-[C:9]-2.[C:10]-[C:11]-[CH3;D1;+0:12]>>[C:10]-[C:11]-[CH2;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:1-[#16:7]-[C:8]-[C:9]-2 | 76 | [{"value": 76.0, "product": "C1(=CC=CC=C1)N1CCN(CC1)C=1N=C(C2=C(N1)CCS2)CCCN", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.83 g (2.5 mmol) of 4-chloro-2-(4-phenylpiperazin-1-yl)-6,7-dihydrothieno[3,2-d]pyrimidine (V) is combined with 8.3 mL of n-propylamine, reacted for 0.2 hours at 130° C. in the microwave. Then the reaction mixture is added to water and extracted with dichloromethane. The organic phase is concentrated by evaporation, t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ncc2c(n1)CCS2 | c1ncc2c(n1)CCS2 | C1C[NH]CC[NH]1.c1ccccc1.c1ncc2c(n1)CCS2 | HCl | O | null | null | CCCN.Clc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2>O>NCCCc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d09de1fe4cd44336976ebc2601bf38a7 | Clc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2>>c1ccc(N2CCN(c3nc4c(c(NC5CCCCC5)n3)SCC4)CC2)cc1 | ClC=1C2=C(N=C(N1)N1CCN(CC1)C1=CC=CC=C1)CCS2>>C1(CCCCC1)NC=1C2=C(N=C(N1)N1CCN(CC1)C1=CC=CC=C1)CCS2 | Cl[c:13]1[c:12]2[c:11]([n:10][c:9]([N:8]3[CH2:7][CH2:6][N:5]([c:4]4[cH:1][cH:19][cH:18][cH:17][cH:16]4)[CH2:26][CH2:25]3)[n:21]1)[CH2:24][CH2:23][S:22]2>>[cH:1]1[cH:2][cH:3][c:4]([N:5]2[CH2:6][CH2:7][N:8]([c:9]3[n:10][c:11]4[c:12]([c:13]([NH:14][CH:15]5[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]5)[n:21]3)[S:22][CH2:23][CH... | Clc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2 | c1ccc(N2CCN(c3nc4c(c(NC5CCCCC5)n3)SCC4)CC2)cc1 | null | null | C1(CCCCC1)N | Aromatic Heterocycle Formation | OtherReaction | 57ad3a4cc600ca7c70bbbe137b4d4fd0ae19774501532a25f9c24f8195b85ccb | b0f572ad6b2b446ecd070d99ad48b6b5e87dc037ba48cc85596343bac1b77f42 | c1ccc(N2CCN(c3nc4c(c(NC5CCCCC5)n3)SCC4)CC2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]2:[c:7]:1-[#16:8]-[C:9]-[C:10]-2.[C:11]-[#7:12](-[c;H0;D3;+0:13]1:[cH;D2;+0:14]:[cH;D2;+0:15]:[cH;D2;+0:16]:[cH;D2;+0:17]:[cH;D2;+0:18]:1)-[C:19]>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]2:[c:7](:[c;H0;D3;+0:1](-[#7:20]-[C:21]3-[C:22]-[CH2;D2;+0:17]-[CH2;D2;+0:16]-[CH2;D2;+0... | 67.4 | [{"value": 34.0, "product": "C1(CCCCC1)NC=1C2=C(N=C(N1)N1CCN(CC1)C1=CC=CC=C1)CCS2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.4, "product": "C1(CCCCC1)NC=1C2=C(N=C(N1)N1CCN(CC1)C1=CC=CC=C1)CCS2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.300 g (0.90 mmol) of 4-chloro-2-(4-phenylpiperazin-1-yl)-6,7-dihydrothieno[3,2-d]pyrimidine (V) is placed in 4 mL of cyclohexylamine, then reacted for 0.1 hours at 130° C. in the microwave. Then the reaction mixture is concentrated by evaporation, the residue is stirred with water and suction filtered. 0.120 g of pro... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Secondary amine | c1ccccc1.c1ncc2c(n1)CCS2 | c1ccccc1.C1CCCCC1.c1ncc2c(n1)CCS2 | c1ccccc1.C1C[NH]CC[NH]1.C1CCCCC1.c1ncc2c(n1)CCS2 | null | C1(CCCCC1)N | null | null | Clc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2>C1(CCCCC1)N>c1ccc(N2CCN(c3nc4c(c(NC5CCCCC5)n3)SCC4)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5b181300b2b640b3beb4612b51da751a | Clc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2.Nc1cccc(Cl)c1>>Clc1cccc(Nc2nc(N3CCN(c4ccccc4)CC3)nc3c2SCC3)c1 | ClC=1C2=C(N=C(N1)N1CCN(CC1)C1=CC=CC=C1)CCS2.ClC=1C=C(C=CC1)N.C(C)(C)N(CC)C(C)C>>ClC=1C=C(C=CC1)NC=1C2=C(N=C(N1)N1CCN(CC1)C1=CC=CC=C1)CCS2 | Cl[c:8]1[n:9][c:10]([N:11]2[CH2:12][CH2:13][N:14]([c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[CH2:21][CH2:22]2)[n:23][c:24]2[c:25]1[S:26][CH2:27][CH2:28]2.[Cl:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH2:7])[cH:29]1>>[Cl:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][c:10]([N:11]3[CH2:12][CH2:13][N:14]([c:15]4[cH:16][cH:17... | Clc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2.Nc1cccc(Cl)c1 | Clc1cccc(Nc2nc(N3CCN(c4ccccc4)CC3)nc3c2SCC3)c1 | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | fb5e9412668273fb4a6a95205a5e70ed69d149f576a8cca3439306ead86363d5 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nc(N3CCN(c4ccccc4)CC3)nc3c2SCC3)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:1-[#16:7]-[C:8]-[C:9]-2.[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:1-[#16:7]-[C:8]-[C:9]-2):[c:13] | null | [] | null | null | null | null | 0.320 g (0.96 mmol) of 4-chloro-2-(4-phenylpiperazin-1-yl)-6,7-dihydrothieno[3,2-d]pyrimidine (V), 1.0 mL (9.5 mmol) of 3-chlorophenylamine, and 0.33 mL (1.92 mmol) of diisopropylethylamine are combined and the mixture is reacted for 0.5 hours at 130° C. in the microwave. Then the reaction mixture is combined with ethy... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncc2c(n1)CCS2 | c1ncc2c(n1)CCS2 | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1.c1ncc2c(n1)CCS2 | HCl | C(C)(=O)OCC | null | null | Clc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2.Nc1cccc(Cl)c1>C(C)(=O)OCC>Clc1cccc(Nc2nc(N3CCN(c4ccccc4)CC3)nc3c2SCC3)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-37845c0c18ff402bbeb24bd22b181119 | COc1cccc(N)c1.Clc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2>>COc1cccc(Nc2nc(N3CCN(c4ccccc4)CC3)nc3c2SCC3)c1 | ClC=1C2=C(N=C(N1)N1CCN(CC1)C1=CC=CC=C1)CCS2.COC=1C=C(C=CC1)N.C(C)(C)N(CC)C(C)C>>COC=1C=C(C=CC1)NC=1C2=C(N=C(N1)N1CCN(CC1)C1=CC=CC=C1)CCS2 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH2:8])[cH:30]1.Cl[c:9]1[n:10][c:11]([N:12]2[CH2:13][CH2:14][N:15]([c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[CH2:22][CH2:23]2)[n:24][c:25]2[c:26]1[S:27][CH2:28][CH2:29]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][c:11]([N:12]3[CH2:13][CH2:14][N:15]([c:16]... | COc1cccc(N)c1.Clc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2 | COc1cccc(Nc2nc(N3CCN(c4ccccc4)CC3)nc3c2SCC3)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | fb5e9412668273fb4a6a95205a5e70ed69d149f576a8cca3439306ead86363d5 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nc(N3CCN(c4ccccc4)CC3)nc3c2SCC3)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:1-[#16:7]-[C:8]-[C:9]-2.[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:1-[#16:7]-[C:8]-[C:9]-2):[c:13] | null | [] | null | null | null | null | 0.320 g (0.96 mmol) of 4-chloro-2-(4-phenylpiperazin-1-yl)-6,7-dihydrothieno[3,2-d]pyrimidine (V), 1.5 mL (13.1 mmol) of 3-methoxyphenylamine, and 0.33 mL (1.92 mmol) of diisopropylethylamine are combined, and reacted for 0.5 hours at 130° C. in the microwave. Then the reaction mixture is purified by chromatography usi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncc2c(n1)CCS2 | c1ncc2c(n1)CCS2 | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1.c1ncc2c(n1)CCS2 | HCl | null | null | null | COc1cccc(N)c1.Clc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2>>COc1cccc(Nc2nc(N3CCN(c4ccccc4)CC3)nc3c2SCC3)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-63fa929833fe43eab777a30478b7665a | Clc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2.Nc1ccccc1>>c1ccc(N2CCN(c3nc4c(c(NC5CCCCC5)n3)SCC4)CC2)cc1 | ClC=1C2=C(N=C(N1)N1CCN(CC1)C1=CC=CC=C1)CCS2.C1(=CC=CC=C1)N>>C1(CCCCC1)NC=1C2=C(N=C(N1)N1CCN(CC1)C1=CC=CC=C1)CCS2 | Cl[c:13]1[c:12]2[c:11]([n:10][c:9]([N:8]3[CH2:7][CH2:6][N:5]([c:4]4[cH:3][cH:2][cH:1][cH:28][cH:27]4)[CH2:26][CH2:25]3)[n:21]1)[CH2:24][CH2:23][S:22]2.[NH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[cH:1]1[cH:2][cH:3][c:4]([N:5]2[CH2:6][CH2:7][N:8]([c:9]3[n:10][c:11]4[c:12]([c:13]([NH:14][CH:15]5[CH2:16][CH2:17][... | Clc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2.Nc1ccccc1 | c1ccc(N2CCN(c3nc4c(c(NC5CCCCC5)n3)SCC4)CC2)cc1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 4ce07cf67d93a3fb55788fa87b75b3266fa05fd3e8885152696c5ee594a6f1e9 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(N2CCN(c3nc4c(c(NC5CCCCC5)n3)SCC4)CC2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]2:[c:7]:1-[#16:8]-[C:9]-[C:10]-2.[NH2;D1;+0:11]-[c;H0;D3;+0:12]1:[cH;D2;+0:13]:[cH;D2;+0:14]:[cH;D2;+0:15]:[cH;D2;+0:16]:[cH;D2;+0:17]:1>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]2:[c:7](:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[CH;D3;+0:12]3-[CH2;D2;+0:13]-[CH2;D2;+0:14]-[CH2;D2;+0:15... | 51 | [{"value": 51.0, "product": "C1(CCCCC1)NC=1C2=C(N=C(N1)N1CCN(CC1)C1=CC=CC=C1)CCS2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.300 g (0.90 mmol) of 4-chloro-2-(4-phenylpiperazin-1-yl)-6,7-dihydrothieno[3,2-d]pyrimidine (V) and 3 mL of phenylamine are combined, then reacted for 0.3 hours at 130° C. in the microwave. Then the reaction mixture is combined with water and extracted with ethyl acetate. The organic phase is dried and evaporated to ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncc2c(n1)CCS2.c1ccccc1 | C1CCCCC1.c1ncc2c(n1)CCS2 | c1ccccc1.C1C[NH]CC[NH]1.C1CCCCC1.c1ncc2c(n1)CCS2 | Other | O | null | null | Clc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2.Nc1ccccc1>O>c1ccc(N2CCN(c3nc4c(c(NC5CCCCC5)n3)SCC4)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9d48ec71432340c793048229b10b8e6a | Clc1nc2c(c(N[C@@H]3CCC[C@H]3OCc3ccccc3)n1)SCC2.Oc1ccc(N2CCNCC2)cc1>>c1ccc(CO[C@@H]2CCC[C@H]2Nc2nc(N3CCN(c4ccccc4)CC3)nc3c2SCC3)cc1 | C(C1=CC=CC=C1)O[C@H]1[C@@H](CCC1)NC=1C2=C(N=C(N1)Cl)CCS2.OC1=CC=C(C=C1)N1CCNCC1>>C(C1=CC=CC=C1)O[C@H]1[C@@H](CCC1)NC=1C2=C(N=C(N1)N1CCN(CC1)C1=CC=CC=C1)CCS2 | Cl[c:15]1[n:14][c:13]([NH:12][C@H:11]2[C@H:7]([O:6][CH2:5][c:4]3[cH:3][cH:2][cH:1][cH:35][cH:34]3)[CH2:8][CH2:9][CH2:10]2)[c:30]2[c:29]([n:28]1)[CH2:33][CH2:32][S:31]2.O[c:23]1[cH:22][cH:21][c:20]([N:19]2[CH2:18][CH2:17][NH:16][CH2:27][CH2:26]2)[cH:25][cH:24]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][O:6][C@@H:7]2[CH2:8][CH2:... | Clc1nc2c(c(N[C@@H]3CCC[C@H]3OCc3ccccc3)n1)SCC2.Oc1ccc(N2CCNCC2)cc1 | c1ccc(CO[C@@H]2CCC[C@H]2Nc2nc(N3CCN(c4ccccc4)CC3)nc3c2SCC3)cc1 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | eb7be01ee34d5949efda935a2f7d4f81348c2c8480e69cd73c5674197db95801 | c19bce30116296b4c5cbc4b5b50b228b1b36a9c5350edd21c3c3186f022a7558 | c1ccc(CO[C@@H]2CCC[C@H]2Nc2nc(N3CCN(c4ccccc4)CC3)nc3c2SCC3)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].O-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10].[#7:11]1-[C:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[C:16]-1>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:14]1-[C:13]-[C:12]-[#7:11]-[C:16]-[C:15]-1):[#7;a:4]:[c:5].[c:8]:[c:7]:[cH;D2;+0:6]:[c:9]:[c:10] | 92.3 | [{"value": 89.0, "product": "C(C1=CC=CC=C1)O[C@H]1[C@@H](CCC1)NC=1C2=C(N=C(N1)N1CCN(CC1)C1=CC=CC=C1)CCS2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.3, "product": "C(C1=CC=CC=C1)O[C@H]1[C@@H](CCC1)NC=1C2=C(N=C(N1)N1CCN(CC1)C1=CC=CC=C1)CCS2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.450 g (1.2 mmol) of ((1R,2R)-2-benzyloxycyclopentyl)(2-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl)amine (chiral) (VIII) and 0.760 mL (5.0 mmol) of 1-phenylpiperazine (III) are placed in 5 mL of dioxane, then reacted for 1 hour at 160° C. in the microwave. The reaction mixture is concentrated by evaporation, and th... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol.Secondary amine | Tertiary amine | c1ncc2c(n1)CCS2.c1ccccc1.C1C[NH]CCN1 | C1C[NH]CC[NH]1.c1ccccc1.c1ncc2c(n1)CCS2 | c1ccccc1.C1CCCC1.C1C[NH]CC[NH]1.c1ccccc1.c1ncc2c(n1)CCS2 | HCl | O1CCOCC1 | null | null | Clc1nc2c(c(N[C@@H]3CCC[C@H]3OCc3ccccc3)n1)SCC2.Oc1ccc(N2CCNCC2)cc1>O1CCOCC1>c1ccc(CO[C@@H]2CCC[C@H]2Nc2nc(N3CCN(c4ccccc4)CC3)nc3c2SCC3)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-23e22e80c1564ca08293ef3f42cc469e | CCOC(=O)c1ccc(N2CCN(c3nc4c(c(NC5CCCCC5)n3)SCC4)CC2)cc1.Clc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2>>NCCCc1nc(N2CCNCC2)nc2c1SCC2 | ClC=1C2=C(N=C(N1)N1CCN(CC1)C1=CC=CC=C1)CCS2.C1(CCCCC1)NC=1C2=C(N=C(N1)N1CCN(CC1)C1=CC=C(C(=O)OCC)C=C1)CCS2>>N1(CCNCC1)C=1N=C(C2=C(N1)CCS2)CCCN | CCOC(=O)c1ccc(N2CCN(c3nc4c(c([NH:1][CH:2]5CCC[CH2:4][CH2:3]5)n3)SCC4)CC2)cc1.Cl[c:5]1[n:6][c:7]([N:8]2[CH2:9][CH2:10][N:11](c3ccccc3)[CH2:12][CH2:13]2)[n:14][c:15]2[c:16]1[S:17][CH2:18][CH2:19]2>>[NH2:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]([N:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)[n:14][c:15]2[c:16]1[S:17][CH2:18... | CCOC(=O)c1ccc(N2CCN(c3nc4c(c(NC5CCCCC5)n3)SCC4)CC2)cc1.Clc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2 | NCCCc1nc(N2CCNCC2)nc2c1SCC2 | null | null | O1CCOCC1 | C-C Coupling | OtherReaction | d388bd2b3ba26b554618ee6cc3e54e4b838b960905e82cb961889d1b035defa2 | c2f67c3cfd557af333861d90ad0846895701eaf451b636b53f1ef70644cde5d2 | c1nc(N2CCNCC2)nc2c1SCC2 | C-C-O-C(=O)-c1:c:c:c(-N2-C-C-N(-c3:n:c4:c(:c(-[NH;D2;+0:1]-[CH;D3;+0:2]5-C-C-C-[CH2;D2;+0:3]-[C:4]-5):n:3)-S-C-C-4)-C-C-2):c:c:1.Cl-[c;H0;D3;+0:5]1:[#7;a:6]:[c:7](-[#7:8]2-[C:9]-[C:10]-[N;H0;D3;+0:11](-c3:c:c:c:c:c:3)-[C:12]-[C:13]-2):[#7;a:14]:[c:15]2:[c:16]:1-[#16:17]-[C:18]-[C:19]-2>>[NH2;D1;+0:1]-[CH2;D2;+0:2]-[C:4... | 80 | [{"value": 80.0, "product": "N1(CCNCC1)C=1N=C(C2=C(N1)CCS2)CCCN", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.9, "product": "N1(CCNCC1)C=1N=C(C2=C(N1)CCS2)CCCN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1.0 g (4.4 mmol) of (2-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl)propylamine (V) and 1.9 g (21.8 mmol) of piperazine (VI) are placed in 10 mL of dioxane, then reacted for 0.7 hours at 150° C. in the microwave. Then the reaction mixture is extracted with water and ethyl acetate, and the organic phase is dried and ev... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Secondary amine.Tertiary amine.Tertiary amine.Tertiary amine.Monosulfide | Primary amine.Secondary amine | c1ccccc1.C1CNCCN1.C1CCCCC1.c1ncc2c(n1)CCS2.C1C[NH]CC[NH]1.c1ccccc1.c1ncc2c(n1)CCS2 | C1C[NH]CCN1.c1ncc2c(n1)CCS2 | C1C[NH]CCN1.c1ncc2c(n1)CCS2 | HCl | O1CCOCC1 | null | null | CCOC(=O)c1ccc(N2CCN(c3nc4c(c(NC5CCCCC5)n3)SCC4)CC2)cc1.Clc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2>O1CCOCC1>NCCCc1nc(N2CCNCC2)nc2c1SCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bfddf97fc106413dbe180be648a2ef64 | CCCNc1nc(N2CCN(c3cccc(C(=O)O)c3)CC2)nc2c1SCC2.NCCCc1nc(N2CCNCC2)nc2c1SCC2>>CCCNc1nc(N2CCN(c3ccc(C#N)cc3)CC2)nc2c1SCC2 | N1(CCNCC1)C=1N=C(C2=C(N1)CCS2)CCCN.CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C(C=CC=C51)P(C6=CC=CC=C6)C7=CC=CC=C7)C.C([O-])([O-])=O.[Cs+].[Cs+].C(CC)NC=1C2=C(N=C(N1)N1CCN(CC1)C=1C=C(C(=O)O)C=CC1)CCS2>>C(CC)NC=1C2=C(N=C(N1)N1CCN(CC1)C1=CC=C(C#N)C=C1)CCS2 | O=[C:16](O)[c:18]1[cH:15][cH:14][cH:13][c:12]([N:11]2[CH2:10][CH2:9][N:8]([c:7]3[n:6][c:5]([NH:4][CH2:3][CH2:2][CH3:1])[c:24]4[c:23]([n:22]3)[CH2:27][CH2:26][S:25]4)[CH2:21][CH2:20]2)[cH:19]1.C(Cc1nc(N2CCNCC2)nc2c1SCC2)C[NH2:17]>>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([N:8]2[CH2:9][CH2:10][N:11]([c:12]3[cH:13][cH:... | CCCNc1nc(N2CCN(c3cccc(C(=O)O)c3)CC2)nc2c1SCC2.NCCCc1nc(N2CCNCC2)nc2c1SCC2 | CCCNc1nc(N2CCN(c3ccc(C#N)cc3)CC2)nc2c1SCC2 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | O.C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 818cec0f457785c4d7016ec9d5649b1ee2acaf660d2700478c3556727207454d | c8ef43b143e4c6192a0d964d13925789c936adea38111dfc2c9902bb16d750e4 | c1ccc(N2CCN(c3ncc4c(n3)CCS4)CC2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5]:[c:6]:[cH;D2;+0:7]:1.[NH2;D1;+0:8]-C-C-C-c1:n:c(-N2-C-C-N-C-C-2):n:c2:c:1-S-C-C-2>>[N;H0;D1;+0:8]#[C;H0;D2;+0:1]-[c;H0;D3;+0:7]1:[c:6]:[c:5]:[c:4]:[c:3]:[cH;D2;+0:2]:1 | null | [] | 80 | CELSIUS | 24 | HOUR | 0.150 g (0.5 mmol) of (2-piperazin-1-yl-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl)propylamine (VII), 0.082 g (0.45 mmol) of 4-bromobenzonitrile (VIII), 0.011 g (0.05 mmol) of palladium acetate, 0.041 g (0.07 mmol) of Xantphos, and 0.204 g (0.6 mmol) of cesium carbonate are placed in 1 mL of toluene, then stirred for 24 ho... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine.Secondary amine.Tertiary amine.Monosulfide | Nitrile | c1ccccc1.C1CNCCN1.c1ncc2c(n1)CCS2 | c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1.c1ncc2c(n1)CCS2 | Other | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O.C1(=CC=CC=C1)C | 80 | 24 | CCCNc1nc(N2CCN(c3cccc(C(=O)O)c3)CC2)nc2c1SCC2.NCCCc1nc(N2CCNCC2)nc2c1SCC2>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O.C1(=CC=CC=C1)C>CCCNc1nc(N2CCN(c3ccc(C#N)cc3)CC2)nc2c1SCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e83822f87533434db16761db473580fb | CCOC(=O)c1ccc(N2CCN(c3nc4c(c(NC5CCCCC5)n3)SCC4)CC2)cc1>>NCCCc1nc(N2CCNCC2)nc2c1SCC2 | C1(CCCCC1)NC=1C2=C(N=C(N1)N1CCN(CC1)C1=CC=C(C(=O)OCC)C=C1)CCS2.C1(=CC=CC=C1)N=C=O>>N1(CCNCC1)C=1N=C(C2=C(N1)CCS2)CCCN | CCOC(=O)c1ccc([N:11]2[CH2:10][CH2:9][N:8]([c:7]3[n:6][c:5]([NH:1][CH:2]4CCC[CH2:4][CH2:3]4)[c:16]4[c:15]([n:14]3)[CH2:19][CH2:18][S:17]4)[CH2:13][CH2:12]2)cc1>>[NH2:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]([N:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)[n:14][c:15]2[c:16]1[S:17][CH2:18][CH2:19]2 | CCOC(=O)c1ccc(N2CCN(c3nc4c(c(NC5CCCCC5)n3)SCC4)CC2)cc1 | NCCCc1nc(N2CCNCC2)nc2c1SCC2 | null | null | O1CCCC1 | Miscellaneous | OtherReaction | fd6f6c1881db0dbacf8056ca2cdd53e1ddac043546e7f04b5d65fc8382c12403 | 7736fdb558970e069de3ef15863996fabe965c23096115c171c2690a437523b9 | c1nc(N2CCNCC2)nc2c1SCC2 | C-C-O-C(=O)-c1:c:c:c(-[N;H0;D3;+0:1]2-[C:2]-[C:3]-[#7:4](-[c:5]3:[#7;a:6]:[c:7]4:[c:8](:[c;H0;D3;+0:9](-[NH;D2;+0:10]-[CH;D3;+0:11]5-C-C-C-[CH2;D2;+0:12]-[C:13]-5):[#7;a:14]:3)-[#16:15]-[C:16]-[C:17]-4)-[C:18]-[C:19]-2):c:c:1>>[NH2;D1;+0:10]-[CH2;D2;+0:11]-[C:13]-[CH2;D2;+0:12]-[c;H0;D3;+0:9]1:[#7;a:14]:[c:5](-[#7:4]2-... | 85.9 | [{"value": 53.0, "product": "N1(CCNCC1)C=1N=C(C2=C(N1)CCS2)CCCN", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.9, "product": "N1(CCNCC1)C=1N=C(C2=C(N1)CCS2)CCCN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 0.330 g (1.0 mmol) of cyclohexyl-(2-piperazin-1-yl-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl)amine (VI) and 0.115 mL (1.0 mmol) of phenyl isocyanate are placed in 12.5 mL of tetrahydrofuran, then stirred for 1 hour at ambient temperature. Then the reaction mixture is concentrated by evaporation. The residue is stirred wit... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine.Tertiary amine | Primary amine.Secondary amine | c1ccccc1.C1C[NH]CC[NH]1.C1CCCCC1.c1ncc2c(n1)CCS2 | C1C[NH]CCN1.c1ncc2c(n1)CCS2 | C1C[NH]CCN1.c1ncc2c(n1)CCS2 | HO- | O1CCCC1 | null | 1 | CCOC(=O)c1ccc(N2CCN(c3nc4c(c(NC5CCCCC5)n3)SCC4)CC2)cc1>O1CCCC1>NCCCc1nc(N2CCNCC2)nc2c1SCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-216ff77aaef14eeca820e83031e3dfac | NCCCc1nc(N2CCN(c3ccc(Br)cc3)CC2)nc2c1SCC2.[I-]>>NCCCc1nc(N2CCN(c3ccc(I)cc3)CC2)nc2c1SCC2 | BrC1=CC=C(C=C1)N1CCN(CC1)C=1N=C(C2=C(N1)CCS2)CCCN.[I-].[Na+].CN([C@H]1[C@@H](CCCC1)N)C>>IC1=CC=C(C=C1)N1CCN(CC1)C=1N=C(C2=C(N1)CCS2)CCCN | Br[c:15]1[cH:14][cH:13][c:12]([N:11]2[CH2:10][CH2:9][N:8]([c:7]3[n:6][c:5]([CH2:4][CH2:3][CH2:2][NH2:1])[c:23]4[c:22]([n:21]3)[CH2:26][CH2:25][S:24]4)[CH2:20][CH2:19]2)[cH:18][cH:17]1.[I-:16]>>[NH2:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]([N:8]2[CH2:9][CH2:10][N:11]([c:12]3[cH:13][cH:14][c:15]([I:16])[cH:17][cH:18]3)[CH... | NCCCc1nc(N2CCN(c3ccc(Br)cc3)CC2)nc2c1SCC2.[I-] | NCCCc1nc(N2CCN(c3ccc(I)cc3)CC2)nc2c1SCC2 | null | [Cu](I)I | O1CCOCC1 | Functional Group Interconversion | OtherReaction | b78ae091f9ea90a571f2e011b77da2eac9952c7b340e2e0185fb0decffadd167 | 4131cd1655d0ec8ecf7e181a36ab37eb3293d734e38ece0acf0e59405d170401 | c1ccc(N2CCN(c3ncc4c(n3)CCS4)CC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[I-;H0;D0:6]>>[I;H0;D1;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 98.1 | [{"value": 81.0, "product": "IC1=CC=C(C=C1)N1CCN(CC1)C=1N=C(C2=C(N1)CCS2)CCCN", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.1, "product": "IC1=CC=C(C=C1)N1CCN(CC1)C=1N=C(C2=C(N1)CCS2)CCCN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | null | null | 1.55 g (3.6 mmol) of {2-[4-(4-bromophenyl)piperazin-1-yl]-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl}propylamine (VII), 1.1 g (7.2 mmol) of sodium iodide, and 0.036 g (0.19 mmol) of copper iodide are taken, and under an argon atmosphere 0.060 mL (0.38 mmol) of trans-N,N-dimethyl-1,2-cyclohexanediamine and 7 mL of anhydrous... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Aromatic halide | c1ccccc1 | c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1.c1ncc2c(n1)CCS2 | Br- | [Cu](I)I.O1CCOCC1 | 140 | null | NCCCc1nc(N2CCN(c3ccc(Br)cc3)CC2)nc2c1SCC2.[I-]>[Cu](I)I.O1CCOCC1>NCCCc1nc(N2CCN(c3ccc(I)cc3)CC2)nc2c1SCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5b08b9a9579d4b74a6c229151927f332 | NC(=O)c1ccncc1.NCCCc1nc(N2CCN(c3ccc(I)cc3)CC2)nc2c1SCC2>>CCCNc1nc(N2CCN(c3ccc(NC(=O)c4ccncc4)cc3)CC2)nc2c1SCC2 | CN([C@H]1[C@@H](CCCC1)N)C.IC1=CC=C(C=C1)N1CCN(CC1)C=1N=C(C2=C(N1)CCS2)CCCN.C(C1=CC=NC=C1)(=O)N.C([O-])([O-])=O.[K+].[K+]>>C(CC)NC=1C2=C(N=C(N1)N1CCN(CC1)C1=CC=C(C=C1)NC(C1=CC=NC=C1)=O)CCS2 | [NH2:16][C:17](=[O:18])[c:19]1[cH:20][cH:21][n:22][cH:23][cH:24]1.I[c:15]1[cH:14][cH:13][c:12]([N:11]2[CH2:10][CH2:9][N:8]([c:7]3[n:6][c:5]([CH2:1][CH2:2][CH2:3][NH2:4])[c:31]4[c:30]([n:29]3)[CH2:34][CH2:33][S:32]4)[CH2:28][CH2:27]2)[cH:26][cH:25]1>>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([N:8]2[CH2:9][CH2:10][N:11... | NC(=O)c1ccncc1.NCCCc1nc(N2CCN(c3ccc(I)cc3)CC2)nc2c1SCC2 | CCCNc1nc(N2CCN(c3ccc(NC(=O)c4ccncc4)cc3)CC2)nc2c1SCC2 | null | [Cu](I)I | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | c7cd1d5c5f03e71257cf7d6ac9e3d94d768a3ef1fb6f04c493a482307006e6d6 | 22b00c4e3ef706faa6b2304a196fb8151e13252c20065c3dbe169d80f96d4076 | O=C(Nc1ccc(N2CCN(c3ncc4c(n3)CCS4)CC2)cc1)c1ccncc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[C:7]-[C:8]-[CH2;D2;+0:9]-[c;H0;D3;+0:10]1:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]2:[c:15]:1-[#16:16]-[C:17]-[C:18]-2.[NH2;D1;+0:19]-[C:20](=[O;D1;H0:21])-[c:22]>>[CH3;D1;+0:9]-[C:8]-[C:7]-[NH;D2;+0:6]-[c;H0;D3;+0:10]1:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]2:[c:15]:1-[#16:1... | null | [] | null | null | null | null | 0.170 g (0.4 mmol) of {2-[4-(4-iodophenyl)piperazin-1-yl]-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl}propylamine (VIII), 0.054 g (0.4 mmol) of isonicotinamide, 0.100 g (0.7 mmol) of potassium carbonate, and 0.004 g (0.02 mmol) of copper iodide are taken, and under an argon atmosphere 1 mL of anhydrous/degassed dioxane and ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amide.Primary amine | Secondary amide.Secondary amine | c1ccccc1.c1ncc2c(n1)CCS2 | c1ccccc1.c1ncc2c(n1)CCS2 | C1C[NH]CC[NH]1.c1ccccc1.c1ccncc1.c1ncc2c(n1)CCS2 | HI | [Cu](I)I.O1CCOCC1 | null | null | NC(=O)c1ccncc1.NCCCc1nc(N2CCN(c3ccc(I)cc3)CC2)nc2c1SCC2>[Cu](I)I.O1CCOCC1>CCCNc1nc(N2CCN(c3ccc(NC(=O)c4ccncc4)cc3)CC2)nc2c1SCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cddcdccb875e4adbbf737287a0e71387 | CC(C)(C)OC(=O)N[C@H]1CCC[C@@H]1Nc1nc(Cl)nc2c1SCC2.CCOC(=O)c1ccc(N2CCN(c3nc4c(c(NC5CCCCC5)n3)SCC4)CC2)cc1>>CC(C)(C)OC(=O)N[C@H]1CCC[C@@H]1Nc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2 | ClC=1N=C(C2=C(N1)CCS2)N[C@@H]2[C@H](CCC2)NC(OC(C)(C)C)=O.C1(CCCCC1)NC=1C2=C(N=C(N1)N1CCN(CC1)C1=CC=C(C(=O)OCC)C=C1)CCS2>>C1(=CC=CC=C1)N1CCN(CC1)C=1N=C(C2=C(N1)CCS2)N[C@@H]2[C@H](CCC2)NC(OC(C)(C)C)=O | Cl[c:17]1[n:16][c:15]([NH:14][C@@H:13]2[C@@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:10][CH2:11][CH2:12]2)[c:32]2[c:31]([n:30]1)[CH2:35][CH2:34][S:33]2.CCOC(=O)[c:25]1[cH:24][cH:23][c:22]([N:21]2[CH2:20][CH2:19][N:18](c3nc4c(c(NC5CCCCC5)n3)SCC4)[CH2:29][CH2:28]2)[cH:27][cH:26]1>>[CH3:1][C:2]([CH3... | CC(C)(C)OC(=O)N[C@H]1CCC[C@@H]1Nc1nc(Cl)nc2c1SCC2.CCOC(=O)c1ccc(N2CCN(c3nc4c(c(NC5CCCCC5)n3)SCC4)CC2)cc1 | CC(C)(C)OC(=O)N[C@H]1CCC[C@@H]1Nc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | eefee5aeed0745bfdadfacc641cc9974cd71a20b90a4141c46f452953306b2bb | 52eb3298e8b8cb378d4087c055851a1b42748200ba72932e506b7d7cc3bad144 | c1ccc(N2CCN(c3nc4c(c(NC5CCCC5)n3)SCC4)CC2)cc1 | C-C-O-C(=O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C1-C-C-C(-N-c2:n:c(-[N;H0;D3;+0:6]3-[C:7]-[C:8]-[#7:9]-[C:10]-[C:11]-3):n:c3:c:2-S-C-C-3)-C-C-1.Cl-[c;H0;D3;+0:12](:[#7;a:13]:[c:14]):[#7;a:15]:[c:16]>>[c:14]:[#7;a:13]:[c;H0;D3;+0:12](-[N;H0;D3;+0:6]1-[C:7]-[C:8]-[#7:9]-[C:10]-[C:11]-1):[#7;a:15]:[c:16].[c:3]:[c:2]:... | null | [] | 160 | CELSIUS | null | null | 1.08 g (2.9 mmol) of tert-butyl [(1S,2S)-2-(2-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamino)cyclopentyl]carbamate (V) (chiral) and 9.9 mmol of 1-phenylpiperazine (VI) are placed in 14 mL of dioxane, then heated to 160° C. for 2.3 hours. The reaction mixture is concentrated by evaporation, the residue is then purif... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Secondary amine.Tertiary amine.Monosulfide | Tertiary amine | c1ncc2c(n1)CCS2.c1ccccc1.C1C[NH]CC[NH]1.C1CCCCC1.c1ncc2c(n1)CCS2 | C1C[NH]CC[NH]1.c1ccccc1.c1ncc2c(n1)CCS2 | C1CCCC1.C1C[NH]CC[NH]1.c1ccccc1.c1ncc2c(n1)CCS2 | HCl | O1CCOCC1 | 160 | null | CC(C)(C)OC(=O)N[C@H]1CCC[C@@H]1Nc1nc(Cl)nc2c1SCC2.CCOC(=O)c1ccc(N2CCN(c3nc4c(c(NC5CCCCC5)n3)SCC4)CC2)cc1>O1CCOCC1>CC(C)(C)OC(=O)N[C@H]1CCC[C@@H]1Nc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-90146dd795e145a2aa64a71cc41b97bb | NC1CCCC1Nc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2.O=C(O)c1ccno1>>O=C(N[C@H]1CCC[C@@H]1Nc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2)c1ccno1 | O1N=CC=C1C(=O)O.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1N=CC=C2)OC(=[N+](C)C)N(C)C.OS(=O)(=O)C(F)(F)F.OS(=O)(=O)C(F)(F)F.C1(=CC=CC=C1)N1CCN(CC1)C=1N=C(C2=C(N1)CCS2)NC2C(CCC2)N.C(C)(C)N(CC)C(C)C>>OS(=O)(=O)C(F)(F)F.C1(=CC=CC=C1)N1CCN(CC1)C=1N=C(C2=C(N1)CCS2)N[C@@H]2[C@H](CCC2)NC(=O)C2=CC=NO2 | [NH2:3][CH:4]1[CH2:5][CH2:6][CH2:7][CH:8]1[NH:9][c:10]1[n:11][c:12]([N:13]2[CH2:14][CH2:15][N:16]([c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[CH2:23][CH2:24]2)[n:25][c:26]2[c:27]1[S:28][CH2:29][CH2:30]2.O[C:2](=[O:1])[c:31]1[cH:32][cH:33][n:34][o:35]1>>[O:1]=[C:2]([NH:3][C@H:4]1[CH2:5][CH2:6][CH2:7][C@@H:8]1[NH:9][c:1... | NC1CCCC1Nc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2.O=C(O)c1ccno1 | O=C(N[C@H]1CCC[C@@H]1Nc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2)c1ccno1 | null | null | CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(N[C@H]1CCC[C@@H]1Nc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2)c1ccno1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#8;a:4]:[#7;a:5]:[c:6]:[c:7]:1.[#7;a:8]:[c:9]-[#7:10]-[CH;D3;+0:11]1-[C:12]-[C:13]-[C:14]-[CH;D3;+0:15]-1-[NH2;D1;+0:16]>>[#7;a:8]:[c:9]-[#7:10]-[C@H;D3;+0:11]1-[C:12]-[C:13]-[C:14]-[C@@H;D3;+0:15]-1-[NH;D2;+0:16]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#8;a:4]:[#7;a:5]:[c:6]:[c:7]:1 | null | [] | null | null | 0.1 | HOUR | 0.004 g (0.03 mmol) of isoxazole-5-carboxylic acid (IX), 0.012 g (0.03 mmol) of O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate (HATU), and 0.017 mL (0.10 mmol) of diisopropylethylamine are placed in 1 mL of dimethylformamide, stirred for 0.1 hours at ambient temperature. Then 0.020 g (0.03 m... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CCCC1.C1C[NH]CC[NH]1.c1ccccc1.c1ncc2c(n1)CCS2.c1cnoc1 | HO- | CN(C=O)C | null | 0.1 | NC1CCCC1Nc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2.O=C(O)c1ccno1>CN(C=O)C>O=C(N[C@H]1CCC[C@@H]1Nc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2)c1ccno1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-97b01ad72ad043d99823deee626f750e | Clc1ccc(N2CCNCC2)cc1.NCCCc1nc(Cl)nc2c1S(=O)(=O)CC2>>NCCCc1nc(N2CCN(c3ccc(Cl)cc3)CC2)nc2c1S(=O)(=O)CC2 | ClC=1N=C(C2=C(N1)CCS2(=O)=O)CCCN.ClC1=CC=C(C=C1)N1CCNCC1>>ClC1=CC=C(C=C1)N1CCN(CC1)C=1N=C(C2=C(N1)CCS2(=O)=O)CCCN | [NH:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]2)[CH2:19][CH2:20]1.Cl[c:7]1[n:6][c:5]([CH2:4][CH2:3][CH2:2][NH2:1])[c:23]2[c:22]([n:21]1)[CH2:28][CH2:27][S:24]2(=[O:25])=[O:26]>>[NH2:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]([N:8]2[CH2:9][CH2:10][N:11]([c:12]3[cH:13][cH:14][c:15]([Cl:16])[... | Clc1ccc(N2CCNCC2)cc1.NCCCc1nc(Cl)nc2c1S(=O)(=O)CC2 | NCCCc1nc(N2CCN(c3ccc(Cl)cc3)CC2)nc2c1S(=O)(=O)CC2 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 615d73505efc462de8b4eb5b401f0ba3432391beb670ab56849ddf5b4adced6d | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=S1(=O)CCc2nc(N3CCN(c4ccccc4)CC3)ncc21 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:10]-[C:11]-[#7:6]-[C:7]-[C:8]-1):[#7;a:4]:[c:5] | 70 | [{"value": 70.0, "product": "ClC1=CC=C(C=C1)N1CCN(CC1)C=1N=C(C2=C(N1)CCS2(=O)=O)CCCN", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.9, "product": "ClC1=CC=C(C=C1)N1CCN(CC1)C=1N=C(C2=C(N1)CCS2(=O)=O)CCCN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | null | null | 0.262 g (1.00 mmol) of (2-chloro-5,5-dioxo-6,7-dihydro-5H-5λ6-thieno[3,2-d]pyrimidin-4-yl)propylamine (II) and 0.433 g (2.20 mmol) of 1-(4-chlorophenyl)piperazine are placed in 4.50 mL of dioxane, then heated to 150° C. in the microwave for 0.75 hours. Then the reaction mixture is concentrated by evaporation, the resid... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ncc2c(n1)CCS2 | C1C[NH]CC[NH]1.c1ncc2c(n1)CCS2 | C1C[NH]CC[NH]1.c1ccccc1.c1ncc2c(n1)CCS2 | HCl | O1CCOCC1 | 150 | null | Clc1ccc(N2CCNCC2)cc1.NCCCc1nc(Cl)nc2c1S(=O)(=O)CC2>O1CCOCC1>NCCCc1nc(N2CCN(c3ccc(Cl)cc3)CC2)nc2c1S(=O)(=O)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-10ccc24e72114f89a9b0b36965a6c886 | CC(C)(C)OC(=O)N1CCCC(Nc2nc(Cl)nc3c2SCC3)C1>>Clc1nc2c(c(NC3CCCNC3)n1)SCC2 | ClC=1N=C(C2=C(N1)CCS2)NC2CN(CCC2)C(=O)OC(C)(C)C.Cl.CO>>Cl.ClC=1N=C(C2=C(N1)CCS2)NC2CNCCC2 | CC(C)(C)OC(=O)[N:13]1[CH2:12][CH2:11][CH2:10][CH:9]([NH:8][c:7]2[c:6]3[c:5]([n:4][c:3]([Cl:2])[n:15]2)[CH2:18][CH2:17][S:16]3)[CH2:14]1>>[Cl:2][c:3]1[n:4][c:5]2[c:6]([c:7]([NH:8][CH:9]3[CH2:10][CH2:11][CH2:12][NH:13][CH2:14]3)[n:15]1)[S:16][CH2:17][CH2:18]2 | CC(C)(C)OC(=O)N1CCCC(Nc2nc(Cl)nc3c2SCC3)C1 | Clc1nc2c(c(NC3CCCNC3)n1)SCC2 | null | null | O1CCOCC1 | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1nc2c(c(NC3CCCNC3)n1)SCC2 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 180.4 | [{"value": 91.0, "product": "Cl.ClC=1N=C(C2=C(N1)CCS2)NC2CNCCC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 180.4, "product": "Cl.ClC=1N=C(C2=C(N1)CCS2)NC2CNCCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | 1.77 g (4.8 mmol) of tert-butyl 3-(2-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamino)piperidin-1-carboxylate (V) is placed in 21.5 mL of a 4% hydrochloric acid solution in dioxane, and methanol is added. The solution is stirred for 0.5 hours at ambient temperature, whereupon a precipitate is formed. This is suction ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | C1CCNCC1.c1ncc2c(n1)CCS2 | HO- | O1CCOCC1 | null | 0.5 | CC(C)(C)OC(=O)N1CCCC(Nc2nc(Cl)nc3c2SCC3)C1>O1CCOCC1>Clc1nc2c(c(NC3CCCNC3)n1)SCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-07797c4aee8a46c3a2a3c4088338977c | CC(C)(C)OC(=O)N[C@H]1CCC[C@@H]1Nc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2.CCN(C(C)C)C(C)C.Clc1nc2c(c(NC3CCCNC3)n1)SCC2>>Cn1cccc1C(=O)N1CCCC(Nc2nc(Cl)nc3c2SCC3)C1 | C1(=CC=CC=C1)N1CCN(CC1)C=1N=C(C2=C(N1)CCS2)N[C@@H]2[C@H](CCC2)NC(OC(C)(C)C)=O.Cl.ClC=1N=C(C2=C(N1)CCS2)NC2CNCCC2.C(C)(C)N(CC)C(C)C.C(C)(C)N(CC)C(C)C>>CN1C(=CC=C1)C(=O)N1CC(CCC1)NC=1C2=C(N=C(N1)Cl)CCS2 | CC(C)(C)O[C:7](N[C@H]1C[CH2:4][CH2:5][C@@H:6]1Nc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2)=[O:8].CC(C)[N:2]([CH2:1]C)[CH:3](C)C.[NH:9]1[CH2:10][CH2:11][CH2:12][CH:13]([NH:14][c:15]2[n:16][c:17]([Cl:18])[n:19][c:20]3[c:21]2[S:22][CH2:23][CH2:24]3)[CH2:25]1>>[CH3:1][n:2]1[cH:3][cH:4][cH:5][c:6]1[C:7](=[O:8])[N:9]1[CH2:10][CH2:11]... | CC(C)(C)OC(=O)N[C@H]1CCC[C@@H]1Nc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2.CCN(C(C)C)C(C)C.Clc1nc2c(c(NC3CCCNC3)n1)SCC2 | Cn1cccc1C(=O)N1CCCC(Nc2nc(Cl)nc3c2SCC3)C1 | null | null | CS(=O)C | Acylation | OtherReaction | 70f5c8f8b24cffce539c4673b93410a075008045cfe36d995231a3eb018ccdec | 8a21bc94cb58e7970c4b11b25bffc3d1ed7c6680d89e3fa4d6e22fa277094e07 | O=C(c1ccc[nH]1)N1CCCC(Nc2ncnc3c2SCC3)C1 | null | 85.6 | [{"value": 85.0, "product": "CN1C(=CC=C1)C(=O)N1CC(CCC1)NC=1C2=C(N=C(N1)Cl)CCS2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.6, "product": "CN1C(=CC=C1)C(=O)N1CC(CCC1)NC=1C2=C(N=C(N1)Cl)CCS2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.1 | HOUR | 0.462 g (3.7 mmol) of 1-methyl-1H-pyrrol-2-carboxylic acid (VII), 1.4 g (9.7 mmol) of O-(7-azabenzotriazol-1-yl-)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate (HATU), and 0.640 mL (3.7 mmol) of diisopropylethylamine are placed in 10 mL of dimethylsulfoxide, then stirred for 0.1 hours at ambient temperature. 0.814 g ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Secondary amine.Secondary amine.Tertiary amine.Tertiary amine.Tertiary amine.Monosulfide.Boc | Tertiary amide | C1CCCC1.C1CNCCN1.c1ccccc1.c1ncc2c(n1)CCS2.C1CCNCC1 | c1ccc[nH]1.C1CC[NH]CC1 | c1ccc[nH]1.C1CC[NH]CC1.c1ncc2c(n1)CCS2 | Other | CS(=O)C | null | 0.1 | CC(C)(C)OC(=O)N[C@H]1CCC[C@@H]1Nc1nc(N2CCN(c3ccccc3)CC2)nc2c1SCC2.CCN(C(C)C)C(C)C.Clc1nc2c(c(NC3CCCNC3)n1)SCC2>CS(=O)C>Cn1cccc1C(=O)N1CCCC(Nc2nc(Cl)nc3c2SCC3)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fc5f599323cc4bb7bdeeee57b7861f3b | CC(=O)O.Oc1ccc(N2CCNCC2)cc1.c1ccc(N2CCN(c3nc4c(c(NC5CCCCC5)n3)SCC4)CC2)cc1>>Oc1ccc(N2CCN(c3nc(O)c4c(n3)CCS4)CC2)cc1 | N1(CCNCC1)C1=CC=C(C=C1)O.C(C)(=O)O.C1(CCCCC1)NC=1C2=C(N=C(N1)N1CCN(CC1)C1=CC=CC=C1)CCS2>>OC1=CC=C(C=C1)N1CCN(CC1)C=1N=C(C2=C(N1)CCS2)O | CC(=O)[OH:13].c1c(N2CCNCC2)c[cH:23][c:2]([OH:1])[cH:3]1.c1c[cH:4][c:5]([N:6]2[CH2:7][CH2:8][N:9]([c:10]3[n:11][c:12](NC4CCCCC4)[c:14]4[c:15]([n:16]3)[CH2:17][CH2:18][S:19]4)[CH2:20][CH2:21]2)[cH:22]c1>>[OH:1][c:2]1[cH:3][cH:4][c:5]([N:6]2[CH2:7][CH2:8][N:9]([c:10]3[n:11][c:12]([OH:13])[c:14]4[c:15]([n:16]3)[CH2:17][CH2... | CC(=O)O.Oc1ccc(N2CCNCC2)cc1.c1ccc(N2CCN(c3nc4c(c(NC5CCCCC5)n3)SCC4)CC2)cc1 | Oc1ccc(N2CCN(c3nc(O)c4c(n3)CCS4)CC2)cc1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 5d4aebcb2aad5c7e7be5ad4151328fb07ae2697623bc90d3003c073fb0f660c8 | 6c745801ca4a7b20549ec821b607ff06c14119a4d90adf04a86b04cf1fc0425e | c1ccc(N2CCN(c3ncc4c(n3)CCS4)CC2)cc1 | C-C(=O)-[OH;D1;+0:1].C1-C-C-C(-N-[c;H0;D3;+0:2]2:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]3:[c:7]:2-[#16:8]-[C:9]-[C:10]-3)-C-C-1.[#7:11]-[c:12]1:[cH;D2;+0:13]:c:c:c:[cH;D2;+0:14]:1.[O;D1;H1:15]-[c:16]1:[cH;D2;+0:17]:c:c(-N2-C-C-N-C-C-2):c:[cH;D2;+0:18]:1>>[#7:11]-[c:12]1:[cH;D2;+0:13]:[cH;D2;+0:17]:[c:16](-[O;D1;H1:15]):[cH;D2;+0... | 89.3 | [{"value": 89.3, "product": "OC1=CC=C(C=C1)N1CCN(CC1)C=1N=C(C2=C(N1)CCS2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 180 | CELSIUS | 16 | HOUR | 1.70 g (9.54 mmol) of 4-piperazin-1-ylphenol is placed in 0.55 mL (9.62 mmol) of glacial acetic acid and heated to 180° C. in the heating block. 0.800 g (3.73 mmol) of 2-ethylsulfanyl-6,7-dihydrothieno[3,2-d]pyrimidin-4-ol (I) is added, then the mixture is left to stand for 1.5 hours at 180° C. and 16 hours at ambient ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine.Secondary amine.Tertiary amine | Aromatic alcohol | c1ccccc1.C1CNCCN1.c1ccccc1.C1CCCCC1.c1ncc2c(n1)CCS2 | c1ccccc1.c1ncc2c(n1)CCS2 | c1ccccc1.C1C[NH]CC[NH]1.c1ncc2c(n1)CCS2 | HO- | O | 180 | 16 | CC(=O)O.Oc1ccc(N2CCNCC2)cc1.c1ccc(N2CCN(c3nc4c(c(NC5CCCCC5)n3)SCC4)CC2)cc1>O>Oc1ccc(N2CCN(c3nc(O)c4c(n3)CCS4)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-05d6277f9d5247f8bc3ff4a91822febd | O=P(Cl)(Cl)Cl.Oc1ccc(N2CCN(c3nc(O)c4c(n3)CCS4)CC2)cc1>>Oc1ccc(N2CCN(c3nc(Cl)c4c(n3)CCS4)CC2)cc1 | OC1=CC=C(C=C1)N1CCN(CC1)C=1N=C(C2=C(N1)CCS2)O.P(=O)(Cl)(Cl)Cl>>ClC=1C2=C(N=C(N1)N1CCN(CC1)C1=CC=C(C=C1)O)CCS2 | O=P(Cl)(Cl)[Cl:13].O[c:12]1[n:11][c:10]([N:9]2[CH2:8][CH2:7][N:6]([c:5]3[cH:4][cH:3][c:2]([OH:1])[cH:23][cH:22]3)[CH2:21][CH2:20]2)[n:16][c:15]2[c:14]1[S:19][CH2:18][CH2:17]2>>[OH:1][c:2]1[cH:3][cH:4][c:5]([N:6]2[CH2:7][CH2:8][N:9]([c:10]3[n:11][c:12]([Cl:13])[c:14]4[c:15]([n:16]3)[CH2:17][CH2:18][S:19]4)[CH2:20][CH2:2... | O=P(Cl)(Cl)Cl.Oc1ccc(N2CCN(c3nc(O)c4c(n3)CCS4)CC2)cc1 | Oc1ccc(N2CCN(c3nc(Cl)c4c(n3)CCS4)CC2)cc1 | null | null | null | Functional Group Interconversion | Alcohol to chloride_POCl3_ortho | 8f305fd901e3bd0073a25a88d9149b63bdb6417de0fa85b75e1ecedc99cc8274 | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1ccc(N2CCN(c3ncc4c(n3)CCS4)CC2)cc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]2:[c:7]:1-[#16:8]-[C:9]-[C:10]-2>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]2:[c:7]:1-[#16:8]-[C:9]-[C:10]-2 | null | [] | 120 | CELSIUS | 4 | HOUR | 1.11 g (3.36 mmol) of 2-[4-(4-hydroxyphenyl)piperazin-1-yl]-6,7-dihydrothieno[3,2-d]pyrimidin-4-ol (II) is placed in 5 mL of phosphorus oxychloride, then stirred for 4 hours at 120° C. Excess phosphorus oxychloride is then distilled off and the residue is combined with water. The precipitate formed is suction filtered,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1ncc2c(n1)CCS2 | c1ncc2c(n1)CCS2 | c1ccccc1.C1C[NH]CC[NH]1.c1ncc2c(n1)CCS2 | HCl | null | 120 | 4 | O=P(Cl)(Cl)Cl.Oc1ccc(N2CCN(c3nc(O)c4c(n3)CCS4)CC2)cc1>>Oc1ccc(N2CCN(c3nc(Cl)c4c(n3)CCS4)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0326a1ec94354c539191d9963459185c | Oc1ccc(N2CCN(c3nc(Cl)c4c(n3)CCS4)CC2)cc1.[N-]=[N+]=[N-]>>[N-]=[N+]=Nc1nc(N2CCN(c3ccc(O)cc3)CC2)nc2c1SCC2 | ClC=1C2=C(N=C(N1)N1CCN(CC1)C1=CC=C(C=C1)O)CCS2.[N-]=[N+]=[N-].[Na+]>>N(=[N+]=[N-])C=1C2=C(N=C(N1)N1CCN(CC1)C1=CC=C(C=C1)O)CCS2 | Cl[c:4]1[n:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([c:11]3[cH:12][cH:13][c:14]([OH:15])[cH:16][cH:17]3)[CH2:18][CH2:19]2)[n:20][c:21]2[c:22]1[S:23][CH2:24][CH2:25]2.[N-:1]=[N+:2]=[N-:3]>>[N-:1]=[N+:2]=[N:3][c:4]1[n:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([c:11]3[cH:12][cH:13][c:14]([OH:15])[cH:16][cH:17]3)[CH2:18][CH2:19]2)[n:20... | Oc1ccc(N2CCN(c3nc(Cl)c4c(n3)CCS4)CC2)cc1.[N-]=[N+]=[N-] | [N-]=[N+]=Nc1nc(N2CCN(c3ccc(O)cc3)CC2)nc2c1SCC2 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 14698c4e8bff0fd93ec6d842b92a126d53b39cbd7692c43fd489204a99e009de | df579c5e1cf1cc42720dad6dd16c8deec88e9170508fbd47357453cfc40bcb7a | c1ccc(N2CCN(c3ncc4c(n3)CCS4)CC2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:1-[#16:7]-[C:8]-[C:9]-2.[N-;H0;D1:10]=[#7;+:11]=[N;-;D1;H0:12]>>[N;-;D1;H0:12]=[#7;+:11]=[N;H0;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:1-[#16:7]-[C:8]-[C:9]-2 | 81.8 | [{"value": 81.8, "product": "N(=[N+]=[N-])C=1C2=C(N=C(N1)N1CCN(CC1)C1=CC=C(C=C1)O)CCS2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 4.5 | HOUR | 1.18 g (2.75 mmol) of 4-[4-(4-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-2-yl)piperazin-1-yl]phenol (III) is placed in 25 mL of dimethylformamide, and 1.20 g (18.46 mmol) of sodium azide is added. The reaction mixture is stirred for 4.5 hours at 100° C. Then it is concentrated by evaporation, and the residue is cooled in... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Azide | c1ncc2c(n1)CCS2 | c1ncc2c(n1)CCS2 | C1C[NH]CC[NH]1.c1ccccc1.c1ncc2c(n1)CCS2 | Other | CN(C=O)C | 100 | 4.5 | Oc1ccc(N2CCN(c3nc(Cl)c4c(n3)CCS4)CC2)cc1.[N-]=[N+]=[N-]>CN(C=O)C>[N-]=[N+]=Nc1nc(N2CCN(c3ccc(O)cc3)CC2)nc2c1SCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5530c57a88fe442580365a2cededc225 | CC(=O)O.Clc1ccc(N2CCNCC2)cc1.c1ccc(N2CCN(c3nc4c(c(NC5CCCCC5)n3)SCC4)CC2)cc1>>Oc1nc(N2CCN(c3ccc(Cl)cc3)CC2)nc2c1SCC2 | ClC1=CC=C(C=C1)N1CCNCC1.C(C)(=O)O.C1(CCCCC1)NC=1C2=C(N=C(N1)N1CCN(CC1)C1=CC=CC=C1)CCS2>>ClC1=CC=C(C=C1)N1CCN(CC1)C=1N=C(C2=C(N1)CCS2)O | CC(=O)[OH:1].C1N[CH2:6][CH2:7][N:8]([c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]2)[CH2:16]1.c1ccc(N2CC[N:5]([c:4]3[n:3][c:2](NC4CCCCC4)[c:20]4[c:19]([n:18]3)[CH2:23][CH2:22][S:21]4)[CH2:17]C2)cc1>>[OH:1][c:2]1[n:3][c:4]([N:5]2[CH2:6][CH2:7][N:8]([c:9]3[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]3)[CH2:16][CH2:17]2)... | CC(=O)O.Clc1ccc(N2CCNCC2)cc1.c1ccc(N2CCN(c3nc4c(c(NC5CCCCC5)n3)SCC4)CC2)cc1 | Oc1nc(N2CCN(c3ccc(Cl)cc3)CC2)nc2c1SCC2 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | ad84e788e86ab5ac0c7ba19887cf3c7fb0eb0e244ce292005ff64aa7f9dcf351 | cfd9ca87b08e3af32bd842ab97fd80f102ce303fa7a4149d73f2cc8a526309bb | c1ccc(N2CCN(c3ncc4c(n3)CCS4)CC2)cc1 | C-C(=O)-[OH;D1;+0:1].C1-C-C-C(-N-[c;H0;D3;+0:2]2:[#7;a:3]:[c:4](-[N;H0;D3;+0:5]3-C-C-N(-c4:c:c:c:c:c:4)-C-[CH2;D2;+0:6]-3):[#7;a:7]:[c:8]3:[c:9]:2-[#16:10]-[C:11]-[C:12]-3)-C-C-1.[c:13]-[#7:14]1-[C:15]-[CH2;D2;+0:16]-N-C-[CH2;D2;+0:17]-1>>[OH;D1;+0:1]-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4](-[N;H0;D3;+0:5]2-[CH2;D2;+0:6]-[CH2;D... | 96.1 | [{"value": 96.1, "product": "ClC1=CC=C(C=C1)N1CCN(CC1)C=1N=C(C2=C(N1)CCS2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 180 | CELSIUS | 16 | HOUR | 1.9 g (9.66 mmol) of 1-(4-chlorophenyl)piperazine is placed in 0.55 mL (9.62 mmol) of glacial acetic acid and heated to 180° C. in the heating block. 0.800 g (3.73 mmol) of 2-ethylsulfanyl-6,7-dihydrothieno[3,2-d]pyrimidin-4-ol (I) is added, then the mixture is left to stand for 1.5 hours at 180° C. and 16 hours at amb... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine.Secondary amine.Tertiary amine.Tertiary amine | Aromatic alcohol.Tertiary amine | C1C[NH]CCN1.c1ccccc1.C1CNCC[NH]1.C1CCCCC1.c1ncc2c(n1)CCS2 | C1C[NH]CC[NH]1.c1ncc2c(n1)CCS2 | C1C[NH]CC[NH]1.c1ccccc1.c1ncc2c(n1)CCS2 | HO- | O | 180 | 16 | CC(=O)O.Clc1ccc(N2CCNCC2)cc1.c1ccc(N2CCN(c3nc4c(c(NC5CCCCC5)n3)SCC4)CC2)cc1>O>Oc1nc(N2CCN(c3ccc(Cl)cc3)CC2)nc2c1SCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d29e99d824fd4a05ad8540dda93672fe | O=P(Cl)(Cl)Cl.Oc1nc(N2CCN(c3ccc(Cl)cc3)CC2)nc2c1SCC2>>Clc1ccc(N2CCN(c3nc(Cl)c4c(n3)CCS4)CC2)cc1 | ClC1=CC=C(C=C1)N1CCN(CC1)C=1N=C(C2=C(N1)CCS2)O.P(=O)(Cl)(Cl)Cl>>ClC=1C2=C(N=C(N1)N1CCN(CC1)C1=CC=C(C=C1)Cl)CCS2 | O=P(Cl)(Cl)[Cl:13].O[c:12]1[n:11][c:10]([N:9]2[CH2:8][CH2:7][N:6]([c:5]3[cH:4][cH:3][c:2]([Cl:1])[cH:23][cH:22]3)[CH2:21][CH2:20]2)[n:16][c:15]2[c:14]1[S:19][CH2:18][CH2:17]2>>[Cl:1][c:2]1[cH:3][cH:4][c:5]([N:6]2[CH2:7][CH2:8][N:9]([c:10]3[n:11][c:12]([Cl:13])[c:14]4[c:15]([n:16]3)[CH2:17][CH2:18][S:19]4)[CH2:20][CH2:2... | O=P(Cl)(Cl)Cl.Oc1nc(N2CCN(c3ccc(Cl)cc3)CC2)nc2c1SCC2 | Clc1ccc(N2CCN(c3nc(Cl)c4c(n3)CCS4)CC2)cc1 | null | null | null | Functional Group Interconversion | Alcohol to chloride_POCl3_ortho | 8f305fd901e3bd0073a25a88d9149b63bdb6417de0fa85b75e1ecedc99cc8274 | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1ccc(N2CCN(c3ncc4c(n3)CCS4)CC2)cc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]2:[c:7]:1-[#16:8]-[C:9]-[C:10]-2>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]2:[c:7]:1-[#16:8]-[C:9]-[C:10]-2 | 85 | [{"value": 85.0, "product": "ClC=1C2=C(N=C(N1)N1CCN(CC1)C1=CC=C(C=C1)Cl)CCS2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | 1.25 g (3.05 mmol) of 2-[4-(4-chlorophenyl)piperazin-1-yl]-6,7-dihydrothieno[3,2-d]pyrimidin-4-ol (II) is placed in 4.50 mL of phosphorus oxychloride, then stirred for 4 hours is at 120° C. Then excess phosphorus oxychloride is distilled off, the residue is combined with water. The precipitate formed is suction filtere... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1ncc2c(n1)CCS2 | c1ncc2c(n1)CCS2 | c1ccccc1.C1C[NH]CC[NH]1.c1ncc2c(n1)CCS2 | HCl | null | null | 4 | O=P(Cl)(Cl)Cl.Oc1nc(N2CCN(c3ccc(Cl)cc3)CC2)nc2c1SCC2>>Clc1ccc(N2CCN(c3nc(Cl)c4c(n3)CCS4)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-63ba69d9ec1c42c5a3e00b419439b75d | Clc1ccc(N2CCN(c3nc(Cl)c4c(n3)CCS4)CC2)cc1.[N-]=[N+]=[N-]>>[N-]=[N+]=Nc1nc(N2CCN(c3ccc(Cl)cc3)CC2)nc2c1SCC2 | ClC=1C2=C(N=C(N1)N1CCN(CC1)C1=CC=C(C=C1)Cl)CCS2.[N-]=[N+]=[N-].[Na+]>>N(=[N+]=[N-])C=1C2=C(N=C(N1)N1CCN(CC1)C1=CC=C(C=C1)Cl)CCS2 | Cl[c:4]1[n:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([c:11]3[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]3)[CH2:18][CH2:19]2)[n:20][c:21]2[c:22]1[S:23][CH2:24][CH2:25]2.[N-:1]=[N+:2]=[N-:3]>>[N-:1]=[N+:2]=[N:3][c:4]1[n:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([c:11]3[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]3)[CH2:18][CH2:19]2)[n:20... | Clc1ccc(N2CCN(c3nc(Cl)c4c(n3)CCS4)CC2)cc1.[N-]=[N+]=[N-] | [N-]=[N+]=Nc1nc(N2CCN(c3ccc(Cl)cc3)CC2)nc2c1SCC2 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 14698c4e8bff0fd93ec6d842b92a126d53b39cbd7692c43fd489204a99e009de | df579c5e1cf1cc42720dad6dd16c8deec88e9170508fbd47357453cfc40bcb7a | c1ccc(N2CCN(c3ncc4c(n3)CCS4)CC2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:1-[#16:7]-[C:8]-[C:9]-2.[N-;H0;D1:10]=[#7;+:11]=[N;-;D1;H0:12]>>[N;-;D1;H0:12]=[#7;+:11]=[N;H0;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:1-[#16:7]-[C:8]-[C:9]-2 | 95 | [{"value": 76.0, "product": "N(=[N+]=[N-])C=1C2=C(N=C(N1)N1CCN(CC1)C1=CC=C(C=C1)Cl)CCS2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.0, "product": "N(=[N+]=[N-])C=1C2=C(N=C(N1)N1CCN(CC1)C1=CC=C(C=C1)Cl)CCS2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 4 | HOUR | 0.950 g (2.59 mmol) of 4-chloro-2-[4-(4-chlorophenyl)piperazin-1-yl]-6,7-dihydrothieno[3,2-d]pyrimidine (III) is placed in 20 mL of dimethylformamide and 0.900 g (13.84 mmol) of sodium azide is added. The reaction mixture is stirred for 4 hours at 100° C. It is then concentrated by evaporation, the residue is cooled in... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Azide | c1ncc2c(n1)CCS2 | c1ncc2c(n1)CCS2 | C1C[NH]CC[NH]1.c1ccccc1.c1ncc2c(n1)CCS2 | Other | CN(C=O)C | 100 | 4 | Clc1ccc(N2CCN(c3nc(Cl)c4c(n3)CCS4)CC2)cc1.[N-]=[N+]=[N-]>CN(C=O)C>[N-]=[N+]=Nc1nc(N2CCN(c3ccc(Cl)cc3)CC2)nc2c1SCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a40edab6a1d04ea8a582a62d45eb99e5 | [N-]=[N+]=Nc1nc(N2CCN(c3ccc(Cl)cc3)CC2)nc2c1SCC2>>Nc1nc(N2CCN(c3ccc(Cl)cc3)CC2)nc2c1SCC2 | N(=[N+]=[N-])C=1C2=C(N=C(N1)N1CCN(CC1)C1=CC=C(C=C1)Cl)CCS2.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].O>>ClC1=CC=C(C=C1)N1CCN(CC1)C=1N=C(C2=C(N1)CCS2)N | [N-]=[N+]=[N:1][c:2]1[n:3][c:4]([N:5]2[CH2:6][CH2:7][N:8]([c:9]3[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]3)[CH2:16][CH2:17]2)[n:18][c:19]2[c:20]1[S:21][CH2:22][CH2:23]2>>[NH2:1][c:2]1[n:3][c:4]([N:5]2[CH2:6][CH2:7][N:8]([c:9]3[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]3)[CH2:16][CH2:17]2)[n:18][c:19]2[c:20]1[S:21][CH... | [N-]=[N+]=Nc1nc(N2CCN(c3ccc(Cl)cc3)CC2)nc2c1SCC2 | Nc1nc(N2CCN(c3ccc(Cl)cc3)CC2)nc2c1SCC2 | null | null | O1CCCC1 | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | c1ccc(N2CCN(c3ncc4c(n3)CCS4)CC2)cc1 | [#16:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[N;H0;D2;+0:8]=[N+]=[N-]>>[#16:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[NH2;D1;+0:8] | 84 | [{"value": 84.0, "product": "ClC1=CC=C(C=C1)N1CCN(CC1)C=1N=C(C2=C(N1)CCS2)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.8, "product": "ClC1=CC=C(C=C1)N1CCN(CC1)C=1N=C(C2=C(N1)CCS2)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | 0.820 g (1.76 mmol) of 4-azido-2-[4-(4-chlorophenyl)piperazin-1-yl]-6,7-dihydrothieno[3,2-d]pyrimidine (IV) is placed in 10 mL of tetrahydrofuran and 3.80 mL (3.80 mmol) of lithium aluminum hydride (1M solution in tetrahydrofuran) is slowly added dropwise. The reaction mixture is stirred for 4 hours at ambient temperat... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | C1C[NH]CC[NH]1.c1ccccc1.c1ncc2c(n1)CCS2 | Other | O1CCCC1 | null | 4 | [N-]=[N+]=Nc1nc(N2CCN(c3ccc(Cl)cc3)CC2)nc2c1SCC2>O1CCCC1>Nc1nc(N2CCN(c3ccc(Cl)cc3)CC2)nc2c1SCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4544ba298ba94d35920fe35a794a47a2 | NC(N)=O.[OH-].c1ccc(N2CCN(c3nc4c(c(NC5CCCCC5)n3)SCC4)CC2)cc1>>Oc1nc(O)c2sccc2n1 | [OH-].[Na+].C1(CCCCC1)NC=1C2=C(N=C(N1)N1CCN(CC1)C1=CC=CC=C1)CCS2.NC(=O)N.C>>N1=C(N=C(C2=C1C=CS2)O)O | NC(N)=[O:5].[OH-:1].c1ccc(N2CCN([c:2]3[n:3][c:4](NC4CCCCC4)[c:6]4[c:10]([n:11]3)[CH2:9][CH2:8][S:7]4)CC2)cc1>>[OH:1][c:2]1[n:3][c:4]([OH:5])[c:6]2[s:7][cH:8][cH:9][c:10]2[n:11]1 | NC(N)=O.[OH-].c1ccc(N2CCN(c3nc4c(c(NC5CCCCC5)n3)SCC4)CC2)cc1 | Oc1nc(O)c2sccc2n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 463c2d0f7aa988ec5d99fa6c026aec25eef74239b2d043e8568bee36757c979b | 4716fa95002577b6d25aca6a93b1187496d821d882f864fd3fc3d8a3b269ee37 | c1ncc2sccc2n1 | C1-C-C-C(-N-[c;H0;D3;+0:1]2:[#7;a:2]:[c;H0;D3;+0:3](-N3-C-C-N(-c4:c:c:c:c:c:4)-C-C-3):[#7;a:4]:[c:5]3:[c:6]:2-[S;H0;D2;+0:7]-[CH2;D2;+0:8]-[CH2;D2;+0:9]-3)-C-C-1.N-C(-N)=[O;H0;D1;+0:10].[OH-;D0:11]>>[OH;D1;+0:11]-[c;H0;D3;+0:3]1:[#7;a:4]:[c:5]2:[cH;D2;+0:9]:[cH;D2;+0:8]:[s;H0;D2;+0:7]:[c:6]:2:[c;H0;D3;+0:1](-[OH;D1;+0:... | 75 | [{"value": 75.0, "product": "N1=C(N=C(C2=C1C=CS2)O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 10.0 g (64.0 mmol) of methylester 3-aminothiophene-2-carboxylate (I) and 19.0 g (31.60 mmol) of urea are mixed and melted for 2 hours at 200° C. After cooling, the reaction mixture is dissolved in 1 molar sodium hydroxide solution and decolorized with activated charcoal. It is filtered and the filtrate is cooled and ac... | 10.6084/m9.figshare.5104873.v1 | null | Urea.Secondary amine.Tertiary amine.Tertiary amine.Monosulfide | Aromatic alcohol.Aromatic alcohol | c1ccccc1.C1CNCCN1.C1CCCCC1.c1ncc2c(n1)CCS2 | c1ncc2sccc2n1 | c1ncc2sccc2n1 | Other | null | null | 2 | NC(N)=O.[OH-].c1ccc(N2CCN(c3nc4c(c(NC5CCCCC5)n3)SCC4)CC2)cc1>>Oc1nc(O)c2sccc2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b95c000b4614497ab9487d47603617b3 | CCCN.Clc1nc(Cl)c2sccc2n1>>NCCCc1nc(Cl)nc2ccsc12 | ClC=1N=C(C2=C(N1)C=CS2)Cl.C(CC)N.C(C)(C)N(CC)C(C)C>>ClC=1N=C(C2=C(N1)C=CS2)CCCN | [NH2:1][CH2:2][CH2:3][CH3:4].Cl[c:5]1[n:6][c:7]([Cl:8])[n:9][c:10]2[cH:11][cH:12][s:13][c:14]12>>[NH2:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]([Cl:8])[n:9][c:10]2[cH:11][cH:12][s:13][c:14]12 | CCCN.Clc1nc(Cl)c2sccc2n1 | NCCCc1nc(Cl)nc2ccsc12 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 1af227f5e682c53b68833d770154b0ba7d94c29eb15e663449b3703cd8ccfde7 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1ncc2sccc2n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#16;a:8]:[c:9]:2:1.[C:10]-[C:11]-[CH3;D1;+0:12]>>[C:10]-[C:11]-[CH2;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[c:7]:[#16;a:8]:[c:9]:2:1 | 92 | [{"value": 92.0, "product": "ClC=1N=C(C2=C(N1)C=CS2)CCCN", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.9, "product": "ClC=1N=C(C2=C(N1)C=CS2)CCCN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3.95 g (19.26 mmol) of 2,4-dichlorothieno[3,2-d]pyrimidine (III), 1.90 mL (23.11 mmol) of propylamine, and 6.71 mL (38.52 mmol) of diisopropylethylamine are stirred for 16 hours in 40 mL of tetrahydrofuran at ambient temperature. Then the reaction mixture is concentrated by evaporation, the residue is combined with wat... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ncc2sccc2n1 | c1ncc2sccc2n1 | c1ncc2sccc2n1 | HCl | O1CCCC1 | null | null | CCCN.Clc1nc(Cl)c2sccc2n1>O1CCCC1>NCCCc1nc(Cl)nc2ccsc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1945acaa97ce4d04ac324e577afc72a2 | NCCCc1nc(Cl)nc2ccsc12.O=C1CCC(=O)N1Br>>NCCCc1nc(Cl)nc2c(Br)csc12 | ClC=1N=C(C2=C(N1)C=CS2)CCCN.BrN1C(CCC1=O)=O>>BrC1=CSC2=C1N=C(N=C2CCCN)Cl | [NH2:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]([Cl:8])[n:9][c:10]2[cH:11][cH:13][s:14][c:15]12.O=C1CCC(=O)N1[Br:12]>>[NH2:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]([Cl:8])[n:9][c:10]2[c:11]([Br:12])[cH:13][s:14][c:15]12 | NCCCc1nc(Cl)nc2ccsc12.O=C1CCC(=O)N1Br | NCCCc1nc(Cl)nc2c(Br)csc12 | null | null | C(C)#N | Functional Group Interconversion | Bromination | 59e9b79d95d8d42c0b8266ebbbe84ddc46f9222d623c6cd93e3eb32e20abeae3 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ncc2sccc2n1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#16;a:2]1:[c:3]:[cH;D2;+0:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1:2>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:4]1:[c:3]:[#16;a:2]:[c:10]2:[c:9]:[#7;a:8]:[c:7]:[#7;a:6]:[c:5]:2:1 | 64.6 | [{"value": 61.0, "product": "BrC1=CSC2=C1N=C(N=C2CCCN)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.6, "product": "BrC1=CSC2=C1N=C(N=C2CCCN)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 6 | HOUR | 8.34 g (36.63 mmol) of (2-chlorothieno[3,2-d]pyrimidin-4-yl)propylamine (IV) is dissolved in 60 mL of acetonitrile and 7.89 g (44.32 mmol) of N-bromosuccinimide is added. The reaction mixture is stirred for 16 hours at ambient temperature and for 6 hours at 50° C. Then it is concentrated by evaporation and the residue ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ncc2sccc2n1.C1CCNC1 | c1ncc2sccc2n1 | c1ncc2sccc2n1 | HO- | C(C)#N | 50 | 6 | NCCCc1nc(Cl)nc2ccsc12.O=C1CCC(=O)N1Br>C(C)#N>NCCCc1nc(Cl)nc2c(Br)csc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-af0e7afdd38e4262812b58424aba8782 | Cl.Clc1nc2c(c(NC3CCCNC3)n1)SCC2.NCCCc1nc(Cl)nc2c(Br)csc12>>NCCCc1nc(N2CCN(c3ccc(Cl)cc3)CC2)nc2c(Br)csc12 | BrC1=CSC2=C1N=C(N=C2CCCN)Cl.Cl.ClC=1N=C(C2=C(N1)CCS2)NC2CNCCC2.C(C)(C)N(CC)C(C)C>>BrC1=CSC2=C1N=C(N=C2CCCN)N2CCN(CC2)C2=CC=C(C=C2)Cl | [ClH:16].Clc1n[c:15]2[c:14]([c:20]([NH:8][CH:9]3C[CH2:13][CH2:12][NH:11][CH2:10]3)n1)S[CH2:19][CH2:17]2.Cl[c:7]1[n:6][c:5]([CH2:4][CH2:3][CH2:2][NH2:1])[c:27]2[c:22]([n:21]1)[c:23]([Br:24])[cH:25][s:26]2>>[NH2:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]([N:8]2[CH2:9][CH2:10][N:11]([c:12]3[cH:13][cH:14][c:15]([Cl:16])[cH:17... | Cl.Clc1nc2c(c(NC3CCCNC3)n1)SCC2.NCCCc1nc(Cl)nc2c(Br)csc12 | NCCCc1nc(N2CCN(c3ccc(Cl)cc3)CC2)nc2c(Br)csc12 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | e00e1a880a84b6f5627ecd7a97c17e5e5cda323103e3a5b9e43b0b86fa150e50 | d4d6f744f2307a2ffad8c57bf341a0a942ae71c32e4abbaad02713328c344a5e | c1ccc(N2CCN(c3ncc4sccc4n3)CC2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4](:[#16;a:5]):[c:6]:[#7;a:7]:1.Cl-c1:n:[c;H0;D3;+0:8]2:[c;H0;D3;+0:9](:[c;H0;D3;+0:10](-[NH;D2;+0:11]-[CH;D3;+0:12]3-C-[CH2;D2;+0:13]-[CH2;D2;+0:14]-[NH;D2;+0:15]-[C:16]-3):n:1)-S-[CH2;D2;+0:17]-[CH2;D2;+0:18]-2.[ClH;D0;+0:19]>>[#16;a:5]:[c:4]1:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[N;H0;... | 110.2 | [{"value": 100.0, "product": "BrC1=CSC2=C1N=C(N=C2CCCN)N2CCN(CC2)C2=CC=C(C=C2)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 110.2, "product": "BrC1=CSC2=C1N=C(N=C2CCCN)N2CCN(CC2)C2=CC=C(C=C2)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | 2.00 g (6.20 mmol) of (7-bromo-2-chlorothieno[3,2-d]pyrimidin-4-yl)propylamine (V), 4.64 g (23.59 mmol) of 1-(4-chlorophenyl)piperazine (VI), and 2.13 mL (12.39 mmol) of diisopropylethylamine are placed in 15 mL of dioxane and heated to 100° C. in the microwave for 0.75 hours. As only 50% reacted, the reaction mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Secondary amine.Secondary amine.Monosulfide | Aromatic halide.Tertiary amine.Tertiary amine | C1CCNCC1.c1ncc2c(n1)CCS2.c1ncc2sccc2n1 | C1C[NH]CC[NH]1.c1ccccc1.c1ncc2sccc2n1 | C1C[NH]CC[NH]1.c1ccccc1.c1ncc2sccc2n1 | HCl | O1CCOCC1 | 100 | null | Cl.Clc1nc2c(c(NC3CCCNC3)n1)SCC2.NCCCc1nc(Cl)nc2c(Br)csc12>O1CCOCC1>NCCCc1nc(N2CCN(c3ccc(Cl)cc3)CC2)nc2c(Br)csc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c7cd7bb8a1c444668c417583027e39d9 | C[O-].NCCCc1nc(N2CCN(c3ccc(Cl)cc3)CC2)nc2c(Br)csc12>>COc1csc2c(CCCN)nc(N3CCN(c4ccc(Cl)cc4)CC3)nc12 | BrC1=CSC2=C1N=C(N=C2CCCN)N2CCN(CC2)C2=CC=C(C=C2)Cl.C[O-].[Na+].[I-].[Na+]>>ClC1=CC=C(C=C1)N1CCN(CC1)C=1N=C(C2=C(N1)C(=CS2)OC)CCCN | [CH3:1][O-:2].Br[c:3]1[cH:4][s:5][c:6]2[c:7]([CH2:8][CH2:9][CH2:10][NH2:11])[n:12][c:13]([N:14]3[CH2:15][CH2:16][N:17]([c:18]4[cH:19][cH:20][c:21]([Cl:22])[cH:23][cH:24]4)[CH2:25][CH2:26]3)[n:27][c:28]12>>[CH3:1][O:2][c:3]1[cH:4][s:5][c:6]2[c:7]([CH2:8][CH2:9][CH2:10][NH2:11])[n:12][c:13]([N:14]3[CH2:15][CH2:16][N:17](... | C[O-].NCCCc1nc(N2CCN(c3ccc(Cl)cc3)CC2)nc2c(Br)csc12 | COc1csc2c(CCCN)nc(N3CCN(c4ccc(Cl)cc4)CC3)nc12 | null | [Cu]=O | CO | Heteroatom Alkylation and Arylation | OtherReaction | 852881d4f169a480e970be39ada69412fe1b5d056da0dd2e81187286e0053099 | 51fd03eb6a688046e417b9ed09ea0e72062396d005af1318b9b5f376a97da959 | c1ccc(N2CCN(c3ncc4sccc4n3)CC2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#16;a:3]:[c:4]2:[c:5]:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1.[C;D1;H3:10]-[O-;H0;D1:11]>>[C;D1;H3:10]-[O;H0;D2;+0:11]-[c;H0;D3;+0:1]1:[c:2]:[#16;a:3]:[c:4]2:[c:5]:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1 | 20 | [{"value": 20.0, "product": "ClC1=CC=C(C=C1)N1CCN(CC1)C=1N=C(C2=C(N1)C(=CS2)OC)CCCN", "details": "PERCENTYIELD", "is_desired": false}, {"value": 12.9, "product": "ClC1=CC=C(C=C1)N1CCN(CC1)C=1N=C(C2=C(N1)C(=CS2)OC)CCCN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 160 | CELSIUS | null | null | 2.00 g (4.28 mmol) of {7-bromo-2-[4-(4-chlorophenyl)piperazin-1-yl]thieno[3,2-d]pyrimidin-4-yl}propylamine (VII) is placed in 15 mL of methanol and cooled to some extent. First 0.995 g (18.42 mmol) of sodium methoxide, then 0.187 g (2.36 mmol) of copper (II) oxide, and 0.040 g (0.27 mmol) of sodium iodide are added. Th... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Ether | c1ncc2sccc2n1 | c1ncc2sccc2n1 | c1ncc2sccc2n1.C1C[NH]CC[NH]1.c1ccccc1 | Br- | [Cu]=O.CO | 160 | null | C[O-].NCCCc1nc(N2CCN(c3ccc(Cl)cc3)CC2)nc2c(Br)csc12>[Cu]=O.CO>COc1csc2c(CCCN)nc(N3CCN(c4ccc(Cl)cc4)CC3)nc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-96c7d4d75bf445ef8e08b6b3aec22c59 | CCCNc1nc(N2CCN(c3ccc(Cl)cc3)CC2)nc2c(OS(=O)(=O)C(F)(F)F)csc12>>CCCNc1nc(N2CCN(c3ccc(Cl)cc3)CC2)nc2c1SCC2OS(=O)(=O)C(F)(F)F | S(=O)(=O)(C(F)(F)F)OC1=CSC2=C1N=C(N=C2NCCC)N2CCN(CC2)C2=CC=C(C=C2)Cl.[BH4-].[Na+]>>S(=O)(=O)(C(F)(F)F)OC1CSC2=C1N=C(N=C2NCCC)N2CCN(CC2)C2=CC=C(C=C2)Cl | [CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([N:8]2[CH2:9][CH2:10][N:11]([c:12]3[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]3)[CH2:19][CH2:20]2)[n:21][c:22]2[c:23]1[s:24][cH:25][c:26]2[O:27][S:28](=[O:29])(=[O:30])[C:31]([F:32])([F:33])[F:34]>>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([N:8]2[CH2:9][CH2:10][N:11]([c:12]... | CCCNc1nc(N2CCN(c3ccc(Cl)cc3)CC2)nc2c(OS(=O)(=O)C(F)(F)F)csc12 | CCCNc1nc(N2CCN(c3ccc(Cl)cc3)CC2)nc2c1SCC2OS(=O)(=O)C(F)(F)F | null | null | CO | Reduction | OtherReaction | 86c7871b9f00ad90c5369426a7d31d3a4f779c43135de5bcf9b6d0efe5197929 | 6494b79298919cfd71fc3b54c2d8d5548ad70aacbcfe4bc3563445f4ace326cc | c1ccc(N2CCN(c3ncc4c(n3)CCS4)CC2)cc1 | [#16:1]-[#8:2]-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[s;H0;D2;+0:5]:[c:6]2:[c:7]:1:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:2-[#7:12]>>[#16:1]-[#8:2]-[CH;D3;+0:3]1-[CH2;D2;+0:4]-[S;H0;D2;+0:5]-[c:6]2:[c:7]-1:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:2-[#7:12] | 20.1 | [{"value": 20.0, "product": "S(=O)(=O)(C(F)(F)F)OC1CSC2=C1N=C(N=C2NCCC)N2CCN(CC2)C2=CC=C(C=C2)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 20.1, "product": "S(=O)(=O)(C(F)(F)F)OC1CSC2=C1N=C(N=C2NCCC)N2CCN(CC2)C2=CC=C(C=C2)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | 0.050 g (0.12 mmol) of 2-[4-(4-chlorophenyl)piperazin-1-yl]-4-propylaminothieno[3,2-d]pyrimidin-7-ol triflate (IX) is dissolved in 1 mL of methanol and 0.020 g (0.53 mmol) of sodium borohydride is added. The reaction mixture is stirred for 16 hours at ambient temperature, then concentrated by evaporation. The residue i... | 10.6084/m9.figshare.5104873.v1 | null | null | Monosulfide | c1ncc2sccc2n1 | c1ncc2c(n1)CCS2 | C1C[NH]CC[NH]1.c1ccccc1.c1ncc2c(n1)CCS2 | null | CO | null | 16 | CCCNc1nc(N2CCN(c3ccc(Cl)cc3)CC2)nc2c(OS(=O)(=O)C(F)(F)F)csc12>CO>CCCNc1nc(N2CCN(c3ccc(Cl)cc3)CC2)nc2c1SCC2OS(=O)(=O)C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7a668739fbf345d0a1974fe21ae7e4ec | Cc1cn([C@@H]2O[C@H](CO[Si](c3ccccc3)(c3ccccc3)C(C)(C)C)[C@@H](O)[C@H]2OCCON(C)C)c(=O)[nH]c1=O>>Cc1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2OCCON(C)C)c(=O)[nH]c1=O | [Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N1C(=O)NC(=O)C(=C1)C)OCCON(C)C)O.F.F.F.C(C)N(CC)CC.C(C)N(CC)CC.CO>>CN(OCCO[C@H]1[C@@H](O[C@@H]([C@H]1O)CO)N1C(=O)NC(=O)C(=C1)C)C | CC(C)(C)[Si](c1ccccc1)(c1ccccc1)[O:9][CH2:8][C@H:7]1[O:6][C@@H:5]([n:4]2[cH:3][c:2]([CH3:1])[c:23](=[O:24])[nH:22][c:20]2=[O:21])[C@H:12]([O:13][CH2:14][CH2:15][O:16][N:17]([CH3:18])[CH3:19])[C@@H:10]1[OH:11]>>[CH3:1][c:2]1[cH:3][n:4]([C@@H:5]2[O:6][C@H:7]([CH2:8][OH:9])[C@@H:10]([OH:11])[C@H:12]2[O:13][CH2:14][CH2:15]... | Cc1cn([C@@H]2O[C@H](CO[Si](c3ccccc3)(c3ccccc3)C(C)(C)C)[C@@H](O)[C@H]2OCCON(C)C)c(=O)[nH]c1=O | Cc1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2OCCON(C)C)c(=O)[nH]c1=O | null | null | C(Cl)Cl.C1CCOC1 | Deprotection | Alcohol deprotection from silyl ethers | 5607047bc82bb27c5a65769b01ea0774767f4428c871f65da0b6352111d7a6e9 | 5c02ee98cb6b210a313993bea9e102110eb73637a50746f5457590f98613069b | O=c1ccn([C@H]2CCCO2)c(=O)[nH]1 | C-C(-C)(-C)-[Si](-[O;H0;D2;+0:1]-[C:2]-[C:3]-[#8:4])(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#8:4]-[C:3]-[C:2]-[OH;D1;+0:1] | 92.5 | [{"value": 92.5, "product": "CN(OCCO[C@H]1[C@@H](O[C@@H]([C@H]1O)CO)N1C(=O)NC(=O)C(=C1)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.4, "product": "CN(OCCO[C@H]1[C@@H](O[C@@H]([C@H]1O)CO)N1C(=O)NC(=O)C(=C1)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | Triethylamine trihydrofluoride (3.91 mL, 24.0 mmol) was dissolved in dry THF and triethylamine (1.67 mL, 12 mmol, dry, kept over KOH). This mixture of triethylamine-2HF was then added to 5′-O-tert-butyldiphenylsilyl-2′-O—[N,N-dimethylaminooxyethyl]-5-methyluridine (1.40 g, 2.4 mmol) and stirred at room temperature for ... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | Primary alcohol | c1ccccc1.c1ccccc1 | null | c1cncnc1.C1CCOC1 | Other | C(Cl)Cl.C1CCOC1 | null | 24 | Cc1cn([C@@H]2O[C@H](CO[Si](c3ccccc3)(c3ccccc3)C(C)(C)C)[C@@H](O)[C@H]2OCCON(C)C)c(=O)[nH]c1=O>C(Cl)Cl.C1CCOC1>Cc1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2OCCON(C)C)c(=O)[nH]c1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7f99a04f97a2475d97364648a410fee6 | [Ca+2]>>[Ca] | FC1=CC=C(C=C1)C1=NC(=NC(=C1/C=C/[C@H](C[C@H](CC(=O)O)O)O)C(C)C)N(S(=O)(=O)C)C.O.O.[Cl-].[Ca+2].[Cl-]>>[Ca].FC1=CC=C(C=C1)C1=NC(=NC(=C1/C=C/[C@H](C[C@H](CC(=O)O)O)O)C(C)C)N(S(=O)(=O)C)C | [Ca+2:34]>>[Ca:34] | [Ca+2] | [Ca] | null | null | O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | [Ca+2;H0;D0:1]>>[Ca;H0;D0;+0:1] | null | [] | 40 | CELSIUS | 15 | MINUTE | (E)-7-[4-(4-Fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl](3R,5S)-3,5-dihydroxyhept-6-enoic acid TRIS salt (17.7 g) was dissolved in degassed water (120 ml) at 20° C. then the solution was heated to 40° C. A solution of calcium chloride dihydrate (2.6 g) in water (25 ml) was added dropwise at ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | O | 40 | 0.25 | [Ca+2]>O>[Ca] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b1686cf6e9244c389f3bab2653b3ce9d | [Ca+2]>>[Ca] | FC1=CC=C(C=C1)C1=NC(=NC(=C1/C=C/[C@H](C[C@H](CC(=O)O)O)O)C(C)C)N(S(=O)(=O)C)C.O.O.[Cl-].[Ca+2].[Cl-]>>[Ca].FC1=CC=C(C=C1)C1=NC(=NC(=C1/C=C/[C@H](C[C@H](CC(=O)O)O)O)C(C)C)N(S(=O)(=O)C)C | [Ca+2:34]>>[Ca:34] | [Ca+2] | [Ca] | null | null | O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | [Ca+2;H0;D0:1]>>[Ca;H0;D0;+0:1] | null | [] | null | null | 60 | MINUTE | (E)-7-[4-(4-Fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl](3R,5S)-3,5-dihydroxyhept-6-enoic acid TRIS salt (17.7 g) was dissolved in degassed water (120 ml) at 20° C. A solution of calcium chloride dihydrate (2.6 g) in water (25 ml) was added dropwise at about 20° C. over 20 minutes. The mixtu... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | O | null | 1 | [Ca+2]>O>[Ca] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eee087fed59c4689a189d78aeef2b39e | Clc1cccc(-c2onc3ccc(Br)cc23)c1.O=Cc1ccc(F)cc1>>OC(c1ccc(F)cc1)c1ccc2noc(-c3cccc(Cl)c3)c2c1 | BrC=1C=CC=2C(=C(ON2)C2=CC(=CC=C2)Cl)C1.FC1=CC=C(C=O)C=C1.[Li]CCCC.CCCCCC>>ClC=1C=C(C=CC1)C=1ON=C2C1C=C(C=C2)C(O)C2=CC=C(C=C2)F | Br[c:10]1[cH:11][cH:12][c:13]2[n:14][o:15][c:16](-[c:17]3[cH:18][cH:19][cH:20][c:21]([Cl:22])[cH:23]3)[c:24]2[cH:25]1.[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1>>[OH:1][CH:2]([c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1)[c:10]1[cH:11][cH:12][c:13]2[n:14][o:15][c:16](-[c:17]3[cH:18][cH:19][cH:20][c:21]([Cl:2... | Clc1cccc(-c2onc3ccc(Br)cc23)c1.O=Cc1ccc(F)cc1 | OC(c1ccc(F)cc1)c1ccc2noc(-c3cccc(Cl)c3)c2c1 | null | null | C1CCOC1 | C-C Coupling | Grignard_alcohol | f822b053a4342903753b2398efb1ef26df143aa50697f50ef6a150fdf12a512a | 1c0bd0afc1d5e370e3c8193faf738f03752295e40fa0eb99c756011e9a4be26b | c1ccc(Cc2ccc3noc(-c4ccccc4)c3c2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[#7;a:5]:[#8;a:6]:[c:7]:[c:8]:2:[c:9]:1.[O;H0;D1;+0:10]=[CH;D2;+0:11]-[c:12](:[c:13]):[c:14]>>[OH;D1;+0:10]-[CH;D3;+0:11](-[c:12](:[c:13]):[c:14])-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[#7;a:5]:[#8;a:6]:[c:7]:[c:8]:2:[c:9]:1 | 26.8 | [{"value": 26.8, "product": "ClC=1C=C(C=CC1)C=1ON=C2C1C=C(C=C2)C(O)C2=CC=C(C=C2)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 26.8, "product": "ClC=1C=C(C=CC1)C=1ON=C2C1C=C(C=C2)C(O)C2=CC=C(C=C2)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -70 | CELSIUS | 15 | MINUTE | nBuLi 1.6M in hexane (0.112 mol) was added dropwise at −70° C. under N2 flow to a mixture of 5-bromo-3-(3-chlorophenyl)-2,1-benzisoxazole (0.097 mol) in THF (300 ml). The mixture was stirred at −70° C. for 15 min. A mixture of 4-fluorobenzaldehyde (0.112 mol) in THF (100 ml) was added dropwise. The mixture was stirred ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aldehyde | Secondary alcohol | c1ccc2nocc2c1 | c1ccc2nocc2c1 | c1ccccc1.c1ccc2nocc2c1.c1ccccc1 | Br- | C1CCOC1 | -70 | 0.25 | Clc1cccc(-c2onc3ccc(Br)cc23)c1.O=Cc1ccc(F)cc1>C1CCOC1>OC(c1ccc(F)cc1)c1ccc2noc(-c3cccc(Cl)c3)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-940cf22da48947a68d6702080988e029 | OC(c1ccc(F)cc1)c1ccc2noc(-c3cccc(Cl)c3)c2c1>>O=C(c1ccc(F)cc1)c1ccc2noc(-c3cccc(Cl)c3)c2c1 | ClC=1C=C(C=CC1)C=1ON=C2C1C=C(C=C2)C(O)C2=CC=C(C=C2)F>>ClC=1C=C(C=CC1)C=1ON=C2C1C=C(C=C2)C(=O)C2=CC=C(C=C2)F | [OH:1][CH:2]([c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1)[c:10]1[cH:11][cH:12][c:13]2[n:14][o:15][c:16](-[c:17]3[cH:18][cH:19][cH:20][c:21]([Cl:22])[cH:23]3)[c:24]2[cH:25]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1)[c:10]1[cH:11][cH:12][c:13]2[n:14][o:15][c:16](-[c:17]3[cH:18][cH:19][cH:20][c:21]([Cl:22]... | OC(c1ccc(F)cc1)c1ccc2noc(-c3cccc(Cl)c3)c2c1 | O=C(c1ccc(F)cc1)c1ccc2noc(-c3cccc(Cl)c3)c2c1 | null | O=[Mn]=O | O1CCOCC1 | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C(c1ccccc1)c1ccc2noc(-c3ccccc3)c2c1 | [OH;D1;+0:1]-[CH;D3;+0:2](-[c:3](:[c:4]):[c:5])-[c:6](:[c:7]):[c:8]>>[O;H0;D1;+0:1]=[C;H0;D3;+0:2](-[c:3](:[c:4]):[c:5])-[c:6](:[c:7]):[c:8] | null | [] | 80 | CELSIUS | 3 | HOUR | A mixture of intermediate 1 (0.0514 mol) and MnO2 (18 g) in 1,4-dioxane (200 ml) was stirred at 80° C. for 3 hours, then cooled to room temperature and filtered over celite. The solvent was evaporated till dryness. The product was used without further purification, yielding (quant.) of [3-(3-chlorophenyl)-2,1-benzisoxa... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | c1ccccc1.c1ccc2nocc2c1.c1ccccc1 | null | O=[Mn]=O.O1CCOCC1 | 80 | 3 | OC(c1ccc(F)cc1)c1ccc2noc(-c3cccc(Cl)c3)c2c1>O=[Mn]=O.O1CCOCC1>O=C(c1ccc(F)cc1)c1ccc2noc(-c3cccc(Cl)c3)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-233e49deed1b4a17ba42f269f2354d5e | O=C(c1ccc(F)cc1)c1ccc2noc(-c3cccc(Cl)c3)c2c1>>Nc1ccc(C(=O)c2ccc(F)cc2)cc1C(=O)c1cccc(Cl)c1 | ClC=1C=C(C=CC1)C=1ON=C2C1C=C(C=C2)C(=O)C2=CC=C(C=C2)F>>NC1=C(C=C(C=C1)C(C1=CC=C(C=C1)F)=O)C(=O)C1=CC(=CC=C1)Cl | [n:1]1[c:2]2[cH:3][cH:4][c:5]([C:6](=[O:7])[c:8]3[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]3)[cH:15][c:16]2[c:17](-[c:19]2[cH:20][cH:21][cH:22][c:23]([Cl:24])[cH:25]2)[o:18]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[cH:15][c:16]1[C:17](=[O:18])[c:19]1[cH:20][cH:21][c... | O=C(c1ccc(F)cc1)c1ccc2noc(-c3cccc(Cl)c3)c2c1 | Nc1ccc(C(=O)c2ccc(F)cc2)cc1C(=O)c1cccc(Cl)c1 | null | null | O.C1CCOC1 | Miscellaneous | OtherReaction | 63dfc430e67d3a7ada3c7e8f6e094ee16a92b905651085a196381d3119990ee1 | 2e99338cc955e46b2c0e811178d7128dca9a68ef9fbb467724eba7220efe12b0 | O=C(c1ccccc1)c1cccc(C(=O)c2ccccc2)c1 | [c:1]:[c:2]1:[c:3](:[c:4]):[n;H0;D2;+0:5]:[o;H0;D2;+0:6]:[c;H0;D3;+0:7]:1-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[NH2;D1;+0:5]-[c:3](:[c:4]):[c:2](-[C;H0;D3;+0:7](=[O;H0;D1;+0:6])-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:1] | 100.1 | [{"value": 100.0, "product": "NC1=C(C=C(C=C1)C(C1=CC=C(C=C1)F)=O)C(=O)C1=CC(=CC=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.1, "product": "NC1=C(C=C(C=C1)C(C1=CC=C(C=C1)F)=O)C(=O)C1=CC(=CC=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of intermediate 2 (0.0514 mol) in THF (180 ml) was cooled on an ice bath. TiCl3 15% in water (180 ml) was added dropwise slowly. The mixture was stirred at room temperature overnight, then poured out into ice water and extracted with DCM. The organic layer was separated, dried (MgSO4), filtered and the solven... | 10.6084/m9.figshare.5104873.v1 | null | null | Ketone.Primary amine | c1ccc2nocc2c1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | null | O.C1CCOC1 | null | 8 | O=C(c1ccc(F)cc1)c1ccc2noc(-c3cccc(Cl)c3)c2c1>O.C1CCOC1>Nc1ccc(C(=O)c2ccc(F)cc2)cc1C(=O)c1cccc(Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-03857d6b9804438ab847be67069e97ee | Nc1ccc(C(=O)c2ccc(F)cc2)cc1C(=O)c1cccc(Cl)c1.O=C(Cl)C(Cl)(Cl)Cl>>O=C(c1ccc(F)cc1)c1ccc(NC(=O)C(Cl)(Cl)Cl)c(C(=O)c2cccc(Cl)c2)c1 | ClC(C(=O)Cl)(Cl)Cl.NC1=C(C=C(C=C1)C(C1=CC=C(C=C1)F)=O)C(=O)C1=CC(=CC=C1)Cl.C(C)N(CC)CC>>ClC(C(=O)NC1=C(C=C(C=C1)C(C1=CC=C(C=C1)F)=O)C(C1=CC(=CC=C1)Cl)=O)(Cl)Cl | [O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1)[c:10]1[cH:11][cH:12][c:13]([NH2:14])[c:21]([C:22](=[O:23])[c:24]2[cH:25][cH:26][cH:27][c:28]([Cl:29])[cH:30]2)[cH:31]1.Cl[C:15](=[O:16])[C:17]([Cl:18])([Cl:19])[Cl:20]>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1)[c:10]1[cH:11][cH:12][c:13]([NH:14][C:... | Nc1ccc(C(=O)c2ccc(F)cc2)cc1C(=O)c1cccc(Cl)c1.O=C(Cl)C(Cl)(Cl)Cl | O=C(c1ccc(F)cc1)c1ccc(NC(=O)C(Cl)(Cl)Cl)c(C(=O)c2cccc(Cl)c2)c1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(c1ccccc1)c1cccc(C(=O)c2ccccc2)c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[Cl;D1;H0:4])(-[Cl;D1;H0:5])-[Cl;D1;H0:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]-[C:11]=[O;D1;H0:12]>>[Cl;D1;H0:4]-[C:3](-[Cl;D1;H0:5])(-[Cl;D1;H0:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]-[C:11]=[O;D1;H0:12] | 95.5 | [{"value": 95.0, "product": "ClC(C(=O)NC1=C(C=C(C=C1)C(C1=CC=C(C=C1)F)=O)C(C1=CC(=CC=C1)Cl)=O)(Cl)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.5, "product": "ClC(C(=O)NC1=C(C=C(C=C1)C(C1=CC=C(C=C1)F)=O)C(C1=CC(=CC=C1)Cl)=O)(Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | 30 | MINUTE | Trichloro-acetylchloride (0.0848 mol) was added dropwise at 5° C. to a mixture of intermediate 3 (0.0707 mol) in DCM (250 ml) under N2 flow. The mixture was stirred at 5° C. for 30 minutes. Triethylamine (0.0848 mol) was added dropwise at 5° C. The mixture was stirred at 5° C. for 1 hour, then at room temperature for 2... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | 5 | 0.5 | Nc1ccc(C(=O)c2ccc(F)cc2)cc1C(=O)c1cccc(Cl)c1.O=C(Cl)C(Cl)(Cl)Cl>C(Cl)Cl>O=C(c1ccc(F)cc1)c1ccc(NC(=O)C(Cl)(Cl)Cl)c(C(=O)c2cccc(Cl)c2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4053017f320e42749ffe11e63cb6b74b | O=C(c1ccc(F)cc1)c1ccc(NC(=O)C(Cl)(Cl)Cl)c(C(=O)c2cccc(Cl)c2)c1.[NH4+]>>O=C(c1ccc(F)cc1)c1ccc2[nH]c(=O)nc(-c3cccc(Cl)c3)c2c1 | [NH4+].C(C)(=O)[O-].ClC(C(=O)NC1=C(C=C(C=C1)C(C1=CC=C(C=C1)F)=O)C(C1=CC(=CC=C1)Cl)=O)(Cl)Cl.O>>ClC=1C=C(C=CC1)C1=NC(NC2=CC=C(C=C12)C(C1=CC=C(C=C1)F)=O)=O | O=[C:18]([c:19]1[cH:20][cH:21][cH:22][c:23]([Cl:24])[cH:25]1)[c:26]1[c:13]([NH:14][C:15](C(Cl)(Cl)Cl)=[O:16])[cH:12][cH:11][c:10]([C:2](=[O:1])[c:3]2[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]2)[cH:27]1.[NH4+:17]>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1)[c:10]1[cH:11][cH:12][c:13]2[nH:14][c:15](=[O:16])[n:17][... | O=C(c1ccc(F)cc1)c1ccc(NC(=O)C(Cl)(Cl)Cl)c(C(=O)c2cccc(Cl)c2)c1.[NH4+] | O=C(c1ccc(F)cc1)c1ccc2[nH]c(=O)nc(-c3cccc(Cl)c3)c2c1 | null | null | CS(=O)C | Aromatic Heterocycle Formation | OtherReaction | 34356251393ced07649e3f2d79584418a4a8dc983e24c794ec9fd18e790ecc31 | 1620ff2b4fcf2514dc5381b8c0e77d605f9d7258e5a6b5dfb277498e8a5ebb1a | O=C(c1ccccc1)c1ccc2[nH]c(=O)nc(-c3ccccc3)c2c1 | Cl-C(-Cl)(-Cl)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:3]-[c:4](:[c:5]):[c:6](-[C;H0;D3;+0:7](=O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:13].[NH4+;D0:14]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[n;H0;D2;+0:14]:[c;H0;D3;+0:7](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:6](:[c:13]):[c:4](:[c:5]):[nH;D2;+0:3]:1 | 72.4 | [{"value": 72.0, "product": "ClC=1C=C(C=CC1)C1=NC(NC2=CC=C(C=C12)C(C1=CC=C(C=C1)F)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.4, "product": "ClC=1C=C(C=CC1)C1=NC(NC2=CC=C(C=C12)C(C1=CC=C(C=C1)F)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 4 | HOUR | Acetic acid, ammonium salt (0.135 mol) was added at room temperature to a mixture of intermediate 4 (0.0675 mol) in DMSO (300 ml). The mixture was stirred at 60° C. for 4 hours, then brought to room temperature and poured out into water. The precipitate was filtered, washed with water, taken up in warm CH3CN, filtered,... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Ketone.Secondary amide | null | c1ccccc1 | c1ccc2ncncc2c1 | c1ccccc1.c1ccc2ncncc2c1.c1ccccc1 | HCl | CS(=O)C | 60 | 4 | O=C(c1ccc(F)cc1)c1ccc(NC(=O)C(Cl)(Cl)Cl)c(C(=O)c2cccc(Cl)c2)c1.[NH4+]>CS(=O)C>O=C(c1ccc(F)cc1)c1ccc2[nH]c(=O)nc(-c3cccc(Cl)c3)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-811dcd1b6fb74c07ae99ce1c64a9a47d | O=C(c1ccc(F)cc1)c1ccc2[nH]c(=O)nc(-c3cccc(Cl)c3)c2c1.O=P(Cl)(Cl)Cl>>O=C(c1ccc(F)cc1)c1ccc2nc(Cl)nc(-c3cccc(Cl)c3)c2c1 | ClC=1C=C(C=CC1)C1=NC(NC2=CC=C(C=C12)C(C1=CC=C(C=C1)F)=O)=O.P(=O)(Cl)(Cl)Cl>>ClC1=NC2=CC=C(C=C2C(=N1)C1=CC(=CC=C1)Cl)C(=O)C1=CC=C(C=C1)F | O=[c:15]1[nH:14][c:13]2[cH:12][cH:11][c:10]([C:2](=[O:1])[c:3]3[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]3)[cH:27][c:26]2[c:18](-[c:19]2[cH:20][cH:21][cH:22][c:23]([Cl:24])[cH:25]2)[n:17]1.O=P(Cl)(Cl)[Cl:16]>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1)[c:10]1[cH:11][cH:12][c:13]2[n:14][c:15]([Cl:16])[n:17][c:18]... | O=C(c1ccc(F)cc1)c1ccc2[nH]c(=O)nc(-c3cccc(Cl)c3)c2c1.O=P(Cl)(Cl)Cl | O=C(c1ccc(F)cc1)c1ccc2nc(Cl)nc(-c3cccc(Cl)c3)c2c1 | null | null | null | Functional Group Interconversion | OtherReaction | 3788560e87eee8765e749543914a91a512631307b97fad163ebef894d2a0ea68 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | O=C(c1ccccc1)c1ccc2ncnc(-c3ccccc3)c2c1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[c:5]:[c:6](:[c:7]):[nH;D2;+0:8]:1>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[c:5]:[c:6](:[c:7]):[n;H0;D2;+0:8]:1 | 40 | [{"value": 40.0, "product": "ClC1=NC2=CC=C(C=C2C(=N1)C1=CC(=CC=C1)Cl)C(=O)C1=CC=C(C=C1)F", "details": "PERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 3 | HOUR | Intermediate 5 (0.0528 mol) was added in phosphoryl chloride (200 ml) at room temperature. The mixture was stirred at 100° C. for 3 hours and cooled to room temperature. The solvent was evaporated. The residue was taken up in DCM. The solvent was evaporated till dryness. The residue was taken up in DCM, poured out into... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccccc1.c1ccc2ncncc2c1.c1ccccc1 | HCl | null | 100 | 3 | O=C(c1ccc(F)cc1)c1ccc2[nH]c(=O)nc(-c3cccc(Cl)c3)c2c1.O=P(Cl)(Cl)Cl>>O=C(c1ccc(F)cc1)c1ccc2nc(Cl)nc(-c3cccc(Cl)c3)c2c1 |
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