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-0387783899c642a8b7eb4ba379bcdf5d | ord-c220962fb2bf497885276694ceb1098c | CC(C)(C)OC(=O)N1CCC(Nc2cccc3c(Cl)nccc23)CC1.CCO>>Oc1nccc2c(NC3CCNCC3)cccc12 | ClC1=NC=CC2=C(C=CC=C12)NC1CCN(CC1)C(=O)OC(C)(C)C.Cl.C(C)O>>Cl.OC1=NC=CC2=C(C=CC=C12)NC1CCNCC1 | CC(C)(C)OC(=O)[N:13]1[CH2:12][CH2:11][CH:10]([NH:9][c:8]2[c:7]3[cH:6][cH:5][n:4][c:3](Cl)[c:19]3[cH:18][cH:17][cH:16]2)[CH2:15][CH2:14]1.CC[OH:2]>>[OH:2][c:3]1[n:4][cH:5][cH:6][c:7]2[c:8]([NH:9][CH:10]3[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]3)[cH:16][cH:17][cH:18][c:19]12 | CC(C)(C)OC(=O)N1CCC(Nc2cccc3c(Cl)nccc23)CC1.CCO | Oc1nccc2c(NC3CCNCC3)cccc12 | null | null | C(C)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 4be42df42161d3e4501211268c062b45b3d4e25d60ed59a2658de168f9194226 | de2f28cc1c3a2a95cdd3d1ada4dc87abcced8bfbcdb89c7e6652b9ee92c9e650 | c1cc(NC2CCNCC2)c2ccncc2c1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5].Cl-[c;H0;D3;+0:6](:[#7;a:7]:[c:8]):[c:9](:[c:10]):[c:11].C-C-[OH;D1;+0:12]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5].[OH;D1;+0:12]-[c;H0;D3;+0:6](:[#7;a:7]:[c:8]):[c:9](:[c:10]):[c:11] | null | [] | 85 | CELSIUS | null | null | Intermediate 84 (76.6 mg) was added with concentrated hydrochloric acid (1.5 ml) and stirred with heating at 85° C. for 7 hours. The reaction mixture was cooled to room temperature, and then the residue was added with ethanol (1 ml) and diethyl ether (2 ml). The deposited precipitates were collected by filtration and w... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester.Ether.Primary alcohol.Boc | Aromatic alcohol.Secondary amine | C1CC[NH]CC1.c1ccc2cnccc2c1 | C1CCNCC1.c1ccc2cnccc2c1 | C1CCNCC1.c1ccc2cnccc2c1 | HCl | C(C)OCC | 85 | null | CC(C)(C)OC(=O)N1CCC(Nc2cccc3c(Cl)nccc23)CC1.CCO>C(C)OCC>Oc1nccc2c(NC3CCNCC3)cccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-46e100f7ec384b35afcd5adf91303a2d | C=Cc1cncc2cccc(NC3CCC(NC(=O)OC(C)(C)C)CC3)c12>>C=Cc1cncc2cccc(NC3CCC(N)CC3)c12 | C(C)(C)(C)OC(=O)NC1CCC(CC1)NC1=C2C(=CN=CC2=CC=C1)C=C.Cl.CO>>Cl.C(=C)C1=CN=CC2=CC=CC(=C12)NC1CCC(CC1)N | CC(C)(C)OC(=O)[NH:17][CH:16]1[CH2:15][CH2:14][CH:13]([NH:12][c:11]2[cH:10][cH:9][cH:8][c:7]3[cH:6][n:5][cH:4][c:3]([CH:2]=[CH2:1])[c:20]32)[CH2:19][CH2:18]1>>[CH2:1]=[CH:2][c:3]1[cH:4][n:5][cH:6][c:7]2[cH:8][cH:9][cH:10][c:11]([NH:12][CH:13]3[CH2:14][CH2:15][CH:16]([NH2:17])[CH2:18][CH2:19]3)[c:20]12 | C=Cc1cncc2cccc(NC3CCC(NC(=O)OC(C)(C)C)CC3)c12 | C=Cc1cncc2cccc(NC3CCC(N)CC3)c12 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1cc(NC2CCCCC2)c2ccncc2c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (50° C., 2 hours) by using Intermediate 85 (85.5 mg) and 10% hydrogen chloride/methanol solution (2 ml). The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The residue was added with me... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2cnccc2c1.C1CCCCC1 | HO- | null | null | null | C=Cc1cncc2cccc(NC3CCC(NC(=O)OC(C)(C)C)CC3)c12>>C=Cc1cncc2cccc(NC3CCC(N)CC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c94c7c5195254876a3b661a5dd0755df | CCc1cncc2cccc(NC3CCC(NC(=O)OC(C)(C)C)CC3)c12>>CCc1cncc2cccc(NC3CCC(N)CC3)c12 | C(C)(C)(C)OC(=O)NC1CCC(CC1)NC1=C2C(=CN=CC2=CC=C1)CC.Cl.CO>>Cl.C(C)C1=CN=CC2=CC=CC(=C12)NC1CCC(CC1)N | CC(C)(C)OC(=O)[NH:17][CH:16]1[CH2:15][CH2:14][CH:13]([NH:12][c:11]2[cH:10][cH:9][cH:8][c:7]3[cH:6][n:5][cH:4][c:3]([CH2:2][CH3:1])[c:20]32)[CH2:19][CH2:18]1>>[CH3:1][CH2:2][c:3]1[cH:4][n:5][cH:6][c:7]2[cH:8][cH:9][cH:10][c:11]([NH:12][CH:13]3[CH2:14][CH2:15][CH:16]([NH2:17])[CH2:18][CH2:19]3)[c:20]12 | CCc1cncc2cccc(NC3CCC(NC(=O)OC(C)(C)C)CC3)c12 | CCc1cncc2cccc(NC3CCC(N)CC3)c12 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1cc(NC2CCCCC2)c2ccncc2c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (50° C., 2 hours) by using Intermediate 86 (133 mg) and 10% hydrogen chloride/methanol solution (2 ml). The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The residue was added with met... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2cnccc2c1.C1CCCCC1 | HO- | null | null | null | CCc1cncc2cccc(NC3CCC(NC(=O)OC(C)(C)C)CC3)c12>>CCc1cncc2cccc(NC3CCC(N)CC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5ea2cb1dd9a846b5bf3301835d03cccb | Brc1cncc2ccccc12.N>>Nc1cncc2ccccc12 | BrC1=CN=CC2=CC=CC=C12.N>>NC1=CN=CC2=CC=CC=C12 | Br[c:2]1[cH:3][n:4][cH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]12.[NH3:1]>>[NH2:1][c:2]1[cH:3][n:4][cH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]12 | Brc1cncc2ccccc12.N | Nc1cncc2ccccc12 | null | O.O.O.O.O.S(=O)(=O)([O-])[O-].[Cu+2] | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 261fd9f972974897261ca5eac8b1086caae005655bedee979c411e5b22857ba2 | c5668f64a1395fa45312378ed819baaeafc354cdb673b20226ea2853ed14db5d | c1ccc2cnccc2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1:[c:7].[NH3;D0;+0:8]>>[NH2;D1;+0:8]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1:[c:7] | null | [] | 165 | CELSIUS | 21 | HOUR | A suspension of 4-bromoisoquinoline (25.0 g), copper(II) sulfate pentahydrate (30.4 g, Nacalai Tesque), 28% aqueous ammonia (100 ml) and 1,4-dioxane (100 ml) was stirred in a sealed tube at 165° C. for 21 hours. The reaction mixture was cooled to room temperature, the insoluble matters were removed by filtration throug... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Primary amine | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | HBr | O.O.O.O.O.S(=O)(=O)([O-])[O-].[Cu+2].O1CCOCC1 | 165 | 21 | Brc1cncc2ccccc12.N>O.O.O.O.O.S(=O)(=O)([O-])[O-].[Cu+2].O1CCOCC1>Nc1cncc2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6e55001f2da4432ebe9991fc4a77c3aa | Cl.Nc1cncc2ccccc12>>Clc1cncc2ccccc12 | Cl.NC1=CN=CC2=CC=CC=C12.Cl.N(=O)[O-].[Na+].N>>ClC1=CN=CC2=CC=CC=C12 | [ClH:1].N[c:2]1[cH:3][n:4][cH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]12>>[Cl:1][c:2]1[cH:3][n:4][cH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]12 | Cl.Nc1cncc2ccccc12 | Clc1cncc2ccccc12 | null | [Cu]Cl | null | Miscellaneous | OtherReaction | a80b46bfc720178a7247f763a2a5c279a0921fee09e9f9f15b3416ca42dac62e | 1129c10513c603d2647e51dd9713063aaf10bd8a364ed275b9b93c32624e3ba4 | c1ccc2cnccc2c1 | N-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1:[c:7].[ClH;D0;+0:8]>>[Cl;H0;D1;+0:8]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1:[c:7] | null | [] | null | null | 15 | HOUR | Intermediate 87 (1.27 g) was dissolved in 1 N aqueous hydrochloric acid (36 ml) and added dropwise with an aqueous solution (36 ml) of sodium nitrite (1.21 g, Wako Pure Chemical Industries) with ice cooling. The obtained suspension was added dropwise to a solution of copper(I) chloride (1.83 g, Wako Pure Chemical Indus... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic halide | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | Other | [Cu]Cl | null | 15 | Cl.Nc1cncc2ccccc12>[Cu]Cl>Clc1cncc2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d8ae3de07dce41eb80afac012049edb2 | Clc1cncc2ccccc12>>O=[N+]([O-])c1cccc2cncc(Cl)c12 | ClC1=CN=CC2=CC=CC=C12.[N+](=O)([O-])[O-].[K+].N>>ClC1=CN=CC2=CC=CC(=C12)[N+](=O)[O-] | [cH:4]1[cH:5][cH:6][cH:7][c:8]2[cH:9][n:10][cH:11][c:12]([Cl:13])[c:14]12>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8]2[cH:9][n:10][cH:11][c:12]([Cl:13])[c:14]12 | Clc1cncc2ccccc12 | O=[N+]([O-])c1cccc2cncc(Cl)c12 | null | null | S(O)(O)(=O)=O | Functional Group Addition | OtherReaction | af041d80e34a3ce46b5eb910f230615587e5ab9eb4305ac845f1ae2dbd577a25 | 22f3183026a2d99c91ec0c53f0059a15c8421016bd62c8ab45281362b96dc686 | c1ccc2cnccc2c1 | [c:1]:[c:2]:[cH;D2;+0:3]:[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1>>[O;-;D1;H0:10]-[#7;+:11](=[O;D1;H0:12])-[c;H0;D3;+0:3](:[c:2]:[c:1]):[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1 | 69.4 | [{"value": 69.4, "product": "ClC1=CN=CC2=CC=CC(=C12)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Intermediate 88 (375 mg) was dissolved in concentrated sulfuric acid (2 ml), then added with potassium nitrate (260 mg) with ice cooling and stirred for 2 hours. The reaction mixture was added with 28% aqueous ammonia (10 ml) and extracted twice with ethyl acetate (15 ml for each time). The organic layer was dried over... | 10.6084/m9.figshare.5104873.v1 | null | null | Nitro group | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | Other | S(O)(O)(=O)=O | null | 2 | Clc1cncc2ccccc12>S(O)(O)(=O)=O>O=[N+]([O-])c1cccc2cncc(Cl)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fcdc390576094c1d8a9ce9abd10a933f | O=[N+]([O-])c1cccc2cncc(Cl)c12>>Nc1cccc2cncc(Cl)c12 | O.O.[Sn](Cl)Cl.ClC1=CN=CC2=CC=CC(=C12)[N+](=O)[O-].[OH-].[Na+]>>ClC1=CN=CC2=CC=CC(=C12)N | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][cH:5][c:6]2[cH:7][n:8][cH:9][c:10]([Cl:11])[c:12]12>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[cH:7][n:8][cH:9][c:10]([Cl:11])[c:12]12 | O=[N+]([O-])c1cccc2cncc(Cl)c12 | Nc1cccc2cncc(Cl)c12 | null | null | Cl | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2cnccc2c1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 67.5 | [{"value": 67.5, "product": "ClC1=CN=CC2=CC=CC(=C12)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Tin(II) chloride dihydrate (1.70 g) was dissolved in concentrated hydrochloric acid (1 ml), added with a mixture of Intermediate 89 (315 mg) and 2 N aqueous hydrochloric acid (2 ml) with ice cooling and refluxed with heating for 2 hours. The reaction mixture was cooled to room temperature, added with 5 N aqueous sodium... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2cnccc2c1 | Other | Cl | null | null | O=[N+]([O-])c1cccc2cncc(Cl)c12>Cl>Nc1cccc2cncc(Cl)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-72438e154c334ea6b03363a7903a683d | CC(C)(C)OC(=O)N1CCC(=O)CC1.Nc1cccc2cncc(Cl)c12>>CC(C)(C)OC(=O)N1CCC(Nc2cccc3cncc(Cl)c23)CC1 | C(O)([O-])=O.[Na+].ClC1=CN=CC2=CC=CC(=C12)N.O=C1CCN(CC1)C(=O)OC(C)(C)C.[BH4-].[Na+]>>ClC1=CN=CC2=CC=CC(=C12)NC1CCN(CC1)C(=O)OC(C)(C)C | O=[C:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:25][CH2:24]1.[NH2:12][c:13]1[cH:14][cH:15][cH:16][c:17]2[cH:18][n:19][cH:20][c:21]([Cl:22])[c:23]12>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([NH:12][c:13]2[cH:14][cH:15][cH:16][c:17]3[cH:18][n:19][cH... | CC(C)(C)OC(=O)N1CCC(=O)CC1.Nc1cccc2cncc(Cl)c12 | CC(C)(C)OC(=O)N1CCC(Nc2cccc3cncc(Cl)c23)CC1 | null | CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4] | CO.ClCCl | Heteroatom Alkylation and Arylation | Reductive amination with ketone | 42e9e55fb09951ae64da272b20a0fe6708e6155493933c6a5b57bd203fbe3626 | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | c1cc(NC2CCNCC2)c2ccncc2c1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[NH;D2;+0:7]-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1):[c:10] | 21.8 | [{"value": 21.8, "product": "ClC1=CN=CC2=CC=CC(=C12)NC1CCN(CC1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 138 | HOUR | According to the method of Example 103, Step A, a mixture of Intermediate 90 (121 mg), tert-butyl 4-oxo-1-piperidinecarboxylate (274 mg), titanium tetraisopropoxide (0.41 ml) and dichloromethane (7 ml) was stirred at room temperature for 138 hours. The reaction mixture was added with sodium borohydride (114 mg) and met... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | C1CC[NH]CC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2cnccc2c1 | Other | CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4].CO.ClCCl | null | 138 | CC(C)(C)OC(=O)N1CCC(=O)CC1.Nc1cccc2cncc(Cl)c12>CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4].CO.ClCCl>CC(C)(C)OC(=O)N1CCC(Nc2cccc3cncc(Cl)c23)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-caa7bc7c670f452e8af4aeec035bb7bb | CC(C)(C)OC(=O)N1CCC(Nc2cccc3cncc(Cl)c23)CC1>>Clc1cncc2cccc(NC3CCNCC3)c12 | ClC1=CN=CC2=CC=CC(=C12)NC1CCN(CC1)C(=O)OC(C)(C)C.Cl.CO>>Cl.ClC1=CN=CC2=CC=CC(=C12)NC1CCNCC1 | CC(C)(C)OC(=O)[N:16]1[CH2:15][CH2:14][CH:13]([NH:12][c:11]2[cH:10][cH:9][cH:8][c:7]3[cH:6][n:5][cH:4][c:3]([Cl:2])[c:19]32)[CH2:18][CH2:17]1>>[Cl:2][c:3]1[cH:4][n:5][cH:6][c:7]2[cH:8][cH:9][cH:10][c:11]([NH:12][CH:13]3[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]3)[c:19]12 | CC(C)(C)OC(=O)N1CCC(Nc2cccc3cncc(Cl)c23)CC1 | Clc1cncc2cccc(NC3CCNCC3)c12 | null | null | null | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1cc(NC2CCNCC2)c2ccncc2c1 | 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] | 230.4 | [{"value": 230.4, "product": "Cl.ClC1=CN=CC2=CC=CC(=C12)NC1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (room temperature, 2 hours) by using Intermediate 91 (53.5 mg) and 10% hydrogen chloride/methanol solution (2 ml). The solvent was evaporated under reduced pressure, and the residue was added with methanol (1 ml) and diethyl ether (3 ml). The depo... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccc2cnccc2c1.C1CCNCC1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCC(Nc2cccc3cncc(Cl)c23)CC1>>Clc1cncc2cccc(NC3CCNCC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2183330ad69d4daf8b0bf3debc9cee84 | CC(C)(C)OC(=O)C1(N)CCC(=O)CC1.Nc1cccc2cncc(Cl)c12>>CC(C)(C)OC(=O)NC1CCC(Nc2cccc3cncc(Cl)c23)CC1 | C(O)([O-])=O.[Na+].ClC1=CN=CC2=CC=CC(=C12)N.O=C1CCC(CC1)(N)C(=O)OC(C)(C)C.[BH4-].[Na+]>>C(C)(C)(C)OC(=O)NC1CCC(CC1)NC1=C2C(=CN=CC2=CC=C1)Cl | O=[C:12]1[CH2:11][CH2:10][C:9]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])([NH2:8])[CH2:26][CH2:25]1.[NH2:13][c:14]1[cH:15][cH:16][cH:17][c:18]2[cH:19][n:20][cH:21][c:22]([Cl:23])[c:24]12>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][CH:12]([NH:13][c:14]2[cH:15][cH:16][cH:17][c:18... | CC(C)(C)OC(=O)C1(N)CCC(=O)CC1.Nc1cccc2cncc(Cl)c12 | CC(C)(C)OC(=O)NC1CCC(Nc2cccc3cncc(Cl)c23)CC1 | null | CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4] | CO.ClCCl | Protection | OtherReaction | 4a8cf36cfc07554ec0fcb4db795ad7e23fdcb78b4b4aa84e4f6291e0179bfb3f | 156ca1cd24e8fdcd7296a675bc0ef4e78771844949b27717ab0d615ffde695c2 | c1cc(NC2CCCCC2)c2ccncc2c1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[C;H0;D4;+0:4](-[NH2;D1;+0:5])(-[C;H0;D3;+0:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C:13]-[C:14]-1.[NH2;D1;+0:15]-[c:16](:[c:17]):[c:18]>>[C;D1;H3:10]-[C:9](-[C;D1;H3:11])(-[C;D1;H3:12])-[#8:8]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[NH;D2;+0:5]-[CH;D3;+0:4]1-[C:3]... | null | [] | null | null | 120 | HOUR | According to the method of Example 103, Step A, a mixture of Intermediate 90 (100 mg), tert-butyl 4-oxo-1-aminocyclohexylcarboxylate (270 mg), titanium tetraisopropoxide (0.34 ml) and dichloromethane (7 ml) was stirred at room temperature for 120 hours. The reaction mixture was added with sodium borohydride (94 mg) and... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine.Primary amine | Carbamic ester.Ether.Secondary amine.Boc | C1CCCCC1 | C1CCCCC1 | C1CCCCC1.c1ccc2cnccc2c1 | Other | CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4].CO.ClCCl | null | 120 | CC(C)(C)OC(=O)C1(N)CCC(=O)CC1.Nc1cccc2cncc(Cl)c12>CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4].CO.ClCCl>CC(C)(C)OC(=O)NC1CCC(Nc2cccc3cncc(Cl)c23)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fd0fe1d1c92e49348e550fdf4bdb608e | CC(C)(C)OC(=O)NC1CCC(Nc2cccc3cncc(Cl)c23)CC1>>NC1CCC(Nc2cccc3cncc(Cl)c23)CC1 | C(C)(C)(C)OC(=O)NC1CCC(CC1)NC1=C2C(=CN=CC2=CC=C1)Cl.Cl.CO>>Cl.ClC1=CN=CC2=CC=CC(=C12)NC1CCC(CC1)N | CC(C)(C)OC(=O)[NH:2][CH:3]1[CH2:4][CH2:5][CH:6]([NH:7][c:8]2[cH:9][cH:10][cH:11][c:12]3[cH:13][n:14][cH:15][c:16]([Cl:17])[c:18]23)[CH2:19][CH2:20]1>>[NH2:2][CH:3]1[CH2:4][CH2:5][CH:6]([NH:7][c:8]2[cH:9][cH:10][cH:11][c:12]3[cH:13][n:14][cH:15][c:16]([Cl:17])[c:18]23)[CH2:19][CH2:20]1 | CC(C)(C)OC(=O)NC1CCC(Nc2cccc3cncc(Cl)c23)CC1 | NC1CCC(Nc2cccc3cncc(Cl)c23)CC1 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1cc(NC2CCCCC2)c2ccncc2c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4] | 225.3 | [{"value": 225.3, "product": "Cl.ClC1=CN=CC2=CC=CC(=C12)NC1CCC(CC1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (room temperature, 2 hours) by using Intermediate 92 (40.4 mg) and 10% hydrogen chloride/methanol solution (2 ml). The solvent was evaporated under reduced pressure, and the residue was added with methanol (1 ml) and diethyl ether (3 ml). The depo... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | C1CCCCC1.c1ccc2cnccc2c1 | HO- | null | null | null | CC(C)(C)OC(=O)NC1CCC(Nc2cccc3cncc(Cl)c23)CC1>>NC1CCC(Nc2cccc3cncc(Cl)c23)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4b5eef1a0b364453826833678fecada6 | Cc1cncc2ccccc12.O=C1CCC(=O)N1Br>>Cc1cncc2cccc(Br)c12 | CC1=CN=CC2=CC=CC=C12.BrN1C(CCC1=O)=O.N>>BrC1=C2C(=CN=CC2=CC=C1)C | [CH3:1][c:2]1[cH:3][n:4][cH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:12]12.O=C1CCC(=O)N1[Br:11]>>[CH3:1][c:2]1[cH:3][n:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([Br:11])[c:12]12 | Cc1cncc2ccccc12.O=C1CCC(=O)N1Br | Cc1cncc2cccc(Br)c12 | null | null | S(O)(O)(=O)=O | Functional Group Interconversion | Bromination | 9cac9f3adaa01c5b3ba77ecc78b3325ca368823796a491b3ff1d81b1acdc724d | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccc2cnccc2c1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[c:2]:[c:3]:[cH;D2;+0:4]:[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:4](:[c:3]:[c:2]):[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1 | null | [] | null | null | 2 | HOUR | 4-Methylisoquinoline (0.1 ml, synthesized according to the method described in Tetrahedron. Lett. 34, 45, 7239 (1993)) was dissolved in concentrated sulfuric acid (1 ml), then added with N-bromosuccinimide (125 mg) with ice cooling and stirred for 2 hours. The reaction mixture was added with 28% aqueous ammonia (5 ml) ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ccc2cnccc2c1.C1CCNC1 | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | HO- | S(O)(O)(=O)=O | null | 2 | Cc1cncc2ccccc12.O=C1CCC(=O)N1Br>S(O)(O)(=O)=O>Cc1cncc2cccc(Br)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2ef5bc5c67c04ed392a15b43bd1a3710 | CC(C)(C)OC(=O)N[C@@H]1CC[C@H](N)CC1.Cc1cncc2cccc(Br)c12>>Cc1cncc2cccc(N[C@@H]3CC[C@H](NC(=O)OC(C)(C)C)CC3)c12 | BrC1=C2C(=CN=CC2=CC=C1)C.BrC1=C2C(=CN=CC2=CC=C1)C.C(C)(C)(C)P(C(C)(C)C)C(C)(C)C.C(C)(C)(C)OC(=O)N[C@@H]1CC[C@@H](CC1)N.CC(C)([O-])C.[Na+]>>C(C)(C)(C)OC(=O)N[C@@H]1CC[C@@H](CC1)NC1=C2C(=CN=CC2=CC=C1)C | [NH2:11][C@@H:12]1[CH2:13][CH2:14][C@H:15]([NH:16][C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:24][CH2:25]1.Br[c:10]1[cH:9][cH:8][cH:7][c:6]2[cH:5][n:4][cH:3][c:2]([CH3:1])[c:26]21>>[CH3:1][c:2]1[cH:3][n:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([NH:11][C@H:12]3[CH2:13][CH2:14][C@@H:15]([NH:16][C:17](=[O:1... | CC(C)(C)OC(=O)N[C@@H]1CC[C@H](N)CC1.Cc1cncc2cccc(Br)c12 | Cc1cncc2cccc(N[C@@H]3CC[C@H](NC(=O)OC(C)(C)C)CC3)c12 | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C(C)(=O)OCC.C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 17c3dbb58f19c559a89452c2c52a32d81319b5dd6d11e225611cc478eba61c1b | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(NC2CCCCC2)c2ccncc2c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1.[C:10]-[C:11](-[NH2;D1;+0:12])-[C:13]>>[C:10]-[C:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1)-[C:13] | null | [] | 120 | CELSIUS | null | null | According to the method of Example 15, Step A, the title compound was synthesized from Intermediate 93. That is, under nitrogen atmosphere, a suspension of Intermediate 93 (602 mg), tris(dibenzylideneacetone)dipalladium(0) (124 mg), tri(tert-butyl)phosphine (0.5 ml, Kanto Chemicals), cis-N-(tert-butoxycarbonyl)-1,4-cyc... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | c1ccc2cnccc2c1.C1CCCCC1 | HBr | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C(C)(=O)OCC.C1(=CC=CC=C1)C | 120 | null | CC(C)(C)OC(=O)N[C@@H]1CC[C@H](N)CC1.Cc1cncc2cccc(Br)c12>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C(C)(=O)OCC.C1(=CC=CC=C1)C>Cc1cncc2cccc(N[C@@H]3CC[C@H](NC(=O)OC(C)(C)C)CC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7592618e4e1244caaa2a448a9711696a | Cc1cncc2cccc(N[C@@H]3CC[C@H](NC(=O)OC(C)(C)C)CC3)c12>>Cc1cncc2cccc(N[C@@H]3CC[C@H](N)CC3)c12 | C(C)(C)(C)OC(=O)N[C@@H]1CC[C@@H](CC1)NC1=C2C(=CN=CC2=CC=C1)C.Cl.CO>>Cl.CC1=CN=CC2=CC=CC(=C12)N[C@@H]1CC[C@@H](CC1)N | CC(C)(C)OC(=O)[NH:16][C@@H:15]1[CH2:14][CH2:13][C@H:12]([NH:11][c:10]2[cH:9][cH:8][cH:7][c:6]3[cH:5][n:4][cH:3][c:2]([CH3:1])[c:19]32)[CH2:18][CH2:17]1>>[CH3:1][c:2]1[cH:3][n:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([NH:11][C@H:12]3[CH2:13][CH2:14][C@@H:15]([NH2:16])[CH2:17][CH2:18]3)[c:19]12 | Cc1cncc2cccc(N[C@@H]3CC[C@H](NC(=O)OC(C)(C)C)CC3)c12 | Cc1cncc2cccc(N[C@@H]3CC[C@H](N)CC3)c12 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1cc(NC2CCCCC2)c2ccncc2c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (room temperature, 2 hours) by using Intermediate 94 (35.8 mg) and 10% hydrogen chloride/methanol solution (2 ml). The solvent was evaporated under reduced pressure, and the residue was added with methanol (0.5 ml) and diethyl ether (1.5 ml). The ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2cnccc2c1.C1CCCCC1 | HO- | null | null | null | Cc1cncc2cccc(N[C@@H]3CC[C@H](NC(=O)OC(C)(C)C)CC3)c12>>Cc1cncc2cccc(N[C@@H]3CC[C@H](N)CC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7a0d394d3d824ca4a3524777a3aa12a3 | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](N)CC1.Cc1cncc2cccc(Br)c12>>Cc1cncc2cccc(N[C@@H]3CC[C@@H](NC(=O)OC(C)(C)C)CC3)c12 | BrC1=C2C(=CN=CC2=CC=C1)C.BrC1=C2C(=CN=CC2=CC=C1)C.C(C)(C)(C)P(C(C)(C)C)C(C)(C)C.C(C)(C)(C)OC(=O)N[C@@H]1CC[C@H](CC1)N.CC(C)([O-])C.[Na+]>>C(C)(C)(C)OC(=O)N[C@@H]1CC[C@H](CC1)NC1=C2C(=CN=CC2=CC=C1)C | [NH2:11][C@H:12]1[CH2:13][CH2:14][C@H:15]([NH:16][C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:24][CH2:25]1.Br[c:10]1[cH:9][cH:8][cH:7][c:6]2[cH:5][n:4][cH:3][c:2]([CH3:1])[c:26]21>>[CH3:1][c:2]1[cH:3][n:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([NH:11][C@H:12]3[CH2:13][CH2:14][C@H:15]([NH:16][C:17](=[O:18]... | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](N)CC1.Cc1cncc2cccc(Br)c12 | Cc1cncc2cccc(N[C@@H]3CC[C@@H](NC(=O)OC(C)(C)C)CC3)c12 | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C(C)(=O)OCC.C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 17c3dbb58f19c559a89452c2c52a32d81319b5dd6d11e225611cc478eba61c1b | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(NC2CCCCC2)c2ccncc2c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1.[C:10]-[C:11](-[NH2;D1;+0:12])-[C:13]>>[C:10]-[C:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1)-[C:13] | null | [] | 120 | CELSIUS | null | null | According to the method of Example 15, Step A, the title compound was synthesized from Intermediate 93. That is, under nitrogen atmosphere, a suspension of Intermediate 93 (1.13 g), tris(dibenzylideneacetone)dipalladium(0) (0.71 g), tri(tert-butyl)phosphine (0.5 ml), trans-N-(tert-butoxycarbonyl)-1,4-cyclohexanediamine... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | c1ccc2cnccc2c1.C1CCCCC1 | HBr | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C(C)(=O)OCC.C1(=CC=CC=C1)C | 120 | null | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](N)CC1.Cc1cncc2cccc(Br)c12>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C(C)(=O)OCC.C1(=CC=CC=C1)C>Cc1cncc2cccc(N[C@@H]3CC[C@@H](NC(=O)OC(C)(C)C)CC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-59ed023d969d467280c5a315d794f41e | Cc1cncc2cccc(N[C@@H]3CC[C@@H](NC(=O)OC(C)(C)C)CC3)c12>>Cc1cncc2cccc(N[C@@H]3CC[C@@H](N)CC3)c12 | C(C)(C)(C)OC(=O)N[C@@H]1CC[C@H](CC1)NC1=C2C(=CN=CC2=CC=C1)C.Cl.CO>>Cl.CC1=CN=CC2=CC=CC(=C12)N[C@@H]1CC[C@H](CC1)N | CC(C)(C)OC(=O)[NH:16][C@H:15]1[CH2:14][CH2:13][C@H:12]([NH:11][c:10]2[cH:9][cH:8][cH:7][c:6]3[cH:5][n:4][cH:3][c:2]([CH3:1])[c:19]32)[CH2:18][CH2:17]1>>[CH3:1][c:2]1[cH:3][n:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([NH:11][C@H:12]3[CH2:13][CH2:14][C@H:15]([NH2:16])[CH2:17][CH2:18]3)[c:19]12 | Cc1cncc2cccc(N[C@@H]3CC[C@@H](NC(=O)OC(C)(C)C)CC3)c12 | Cc1cncc2cccc(N[C@@H]3CC[C@@H](N)CC3)c12 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1cc(NC2CCCCC2)c2ccncc2c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (room temperature, 2 hours) by using Intermediate 95 (389 mg) and 10% hydrogen chloride/methanol solution (10 ml). The solvent was evaporated under reduced pressure, and the residue was added with methanol (2 ml) and diethyl ether (6 ml). The depo... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2cnccc2c1.C1CCCCC1 | HO- | null | null | null | Cc1cncc2cccc(N[C@@H]3CC[C@@H](NC(=O)OC(C)(C)C)CC3)c12>>Cc1cncc2cccc(N[C@@H]3CC[C@@H](N)CC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e66b85a64f8c49938e94e99c298be080 | CC(C)(C)OC(=O)N1CCC(Nc2cccc3cncc(Br)c23)CC1.C[O-]>>COc1cncc2cccc(NC3CCN(C(=O)OC(C)(C)C)CC3)c12 | BrC1=CN=CC2=CC=CC(=C12)NC1CCN(CC1)C(=O)OC(C)(C)C.C[O-].[Na+].O>>COC1=CN=CC2=CC=CC(=C12)NC1CCN(CC1)C(=O)OC(C)(C)C | Br[c:3]1[cH:4][n:5][cH:6][c:7]2[cH:8][cH:9][cH:10][c:11]([NH:12][CH:13]3[CH2:14][CH2:15][N:16]([C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:24][CH2:25]3)[c:26]12.[CH3:1][O-:2]>>[CH3:1][O:2][c:3]1[cH:4][n:5][cH:6][c:7]2[cH:8][cH:9][cH:10][c:11]([NH:12][CH:13]3[CH2:14][CH2:15][N:16]([C:17](=[O:18])[O:19][... | CC(C)(C)OC(=O)N1CCC(Nc2cccc3cncc(Br)c23)CC1.C[O-] | COc1cncc2cccc(NC3CCN(C(=O)OC(C)(C)C)CC3)c12 | null | [Cu]I | CO.N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | 0f34e313d7c41dee60bf5f543b4ffe47bf78172f8b5a6c756b1c69b3aaf76dfb | 51fd03eb6a688046e417b9ed09ea0e72062396d005af1318b9b5f376a97da959 | c1cc(NC2CCNCC2)c2ccncc2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1:[c:7].[C;D1;H3:8]-[O-;H0;D1:9]>>[C;D1;H3:8]-[O;H0;D2;+0:9]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1:[c:7] | null | [] | 65 | CELSIUS | null | null | A suspension of Intermediate 71 (600 mg) and copper(I) iodide (141 mg, Kanto Chemicals) in methanol (5.5 ml) and pyridine (5.5 ml) was added with sodium methoxide (28% methanol solution, 1.7 ml, Wako Pure Chemical Industries) and stirred with heating at 65° C. for 24 hours. The reaction mixture was cooled to room tempe... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Ether | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | c1ccc2cnccc2c1.C1CC[NH]CC1 | Br- | [Cu]I.CO.N1=CC=CC=C1 | 65 | null | CC(C)(C)OC(=O)N1CCC(Nc2cccc3cncc(Br)c23)CC1.C[O-]>[Cu]I.CO.N1=CC=CC=C1>COc1cncc2cccc(NC3CCN(C(=O)OC(C)(C)C)CC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b56a0268b051416cac8d42612a0103b2 | COc1cncc2cccc(NC3CCN(C(=O)OC(C)(C)C)CC3)c12>>COc1cncc2cccc(NC3CCNCC3)c12 | COC1=CN=CC2=CC=CC(=C12)NC1CCN(CC1)C(=O)OC(C)(C)C.Cl.CO>>Cl.COC1=CN=CC2=CC=CC(=C12)NC1CCNCC1 | CC(C)(C)OC(=O)[N:16]1[CH2:15][CH2:14][CH:13]([NH:12][c:11]2[cH:10][cH:9][cH:8][c:7]3[cH:6][n:5][cH:4][c:3]([O:2][CH3:1])[c:19]32)[CH2:18][CH2:17]1>>[CH3:1][O:2][c:3]1[cH:4][n:5][cH:6][c:7]2[cH:8][cH:9][cH:10][c:11]([NH:12][CH:13]3[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]3)[c:19]12 | COc1cncc2cccc(NC3CCN(C(=O)OC(C)(C)C)CC3)c12 | COc1cncc2cccc(NC3CCNCC3)c12 | null | null | null | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1cc(NC2CCNCC2)c2ccncc2c1 | 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] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (50° C., 2 hours) by using Intermediate 96 (358 mg) and 10% hydrogen chloride/methanol solution (10 ml). The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The residue was added with me... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccc2cnccc2c1.C1CCNCC1 | HO- | null | null | null | COc1cncc2cccc(NC3CCN(C(=O)OC(C)(C)C)CC3)c12>>COc1cncc2cccc(NC3CCNCC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b5b475bd78ac49cc914631e3415b87cc | COc1cncc2cccc(NC3CCC(NC(=O)OC(C)(C)C)CC3)c12>>COc1cncc2cccc(NC3CCC(N)CC3)c12 | C(C)(C)(C)OC(=O)NC1CCC(CC1)NC1=C2C(=CN=CC2=CC=C1)OC.Cl.CO>>Cl.COC1=CN=CC2=CC=CC(=C12)NC1CCC(CC1)N | CC(C)(C)OC(=O)[NH:17][CH:16]1[CH2:15][CH2:14][CH:13]([NH:12][c:11]2[cH:10][cH:9][cH:8][c:7]3[cH:6][n:5][cH:4][c:3]([O:2][CH3:1])[c:20]32)[CH2:19][CH2:18]1>>[CH3:1][O:2][c:3]1[cH:4][n:5][cH:6][c:7]2[cH:8][cH:9][cH:10][c:11]([NH:12][CH:13]3[CH2:14][CH2:15][CH:16]([NH2:17])[CH2:18][CH2:19]3)[c:20]12 | COc1cncc2cccc(NC3CCC(NC(=O)OC(C)(C)C)CC3)c12 | COc1cncc2cccc(NC3CCC(N)CC3)c12 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1cc(NC2CCCCC2)c2ccncc2c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (50° C., 2 hours) by using Intermediate 97 (372 mg) and 10% hydrogen chloride/methanol solution (10 ml). The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The residue was added with me... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2cnccc2c1.C1CCCCC1 | HO- | null | null | null | COc1cncc2cccc(NC3CCC(NC(=O)OC(C)(C)C)CC3)c12>>COc1cncc2cccc(NC3CCC(N)CC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6de56dfb6df84ba996ea22062f1fd467 | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](O)CC1.COc1ccc(C(=O)O)cc1>>COc1ccc(C(=O)O[C@@H]2CC[C@H](NC(=O)OC(C)(C)C)CC2)cc1 | C(C)(C)(C)OC(=O)N[C@@H]1CC[C@H](CC1)O.N(=NC(=O)N(C)C)C(=O)N(C)C.C(C1=CC=C(C=C1)OC)(=O)O.C(CCC)P(CCCC)CCCC>>C(C)(C)(C)OC(=O)N[C@H]1CC[C@H](CC1)OC(C1=CC=C(C=C1)OC)=O | [OH:9][C@H:10]1[CH2:11][CH2:12][C@H:13]([NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22][CH2:23]1.O[C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:25][cH:24]1)=[O:8]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[O:9][C@H:10]2[CH2:11][CH2:12][C@@H:13]([NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19... | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](O)CC1.COc1ccc(C(=O)O)cc1 | COc1ccc(C(=O)O[C@@H]2CC[C@H](NC(=O)OC(C)(C)C)CC2)cc1 | null | null | C(C)(=O)OCC.O1CCCC1 | Acylation | Esterification of Carboxylic Acids | e916c5b009194e30c618975b40d7a233bfcf81339e65494c4e365f67cc5e011d | 12ba7405a548c6b1674f05065819c74f53f1b6165cd54e84e1f2f208042fe660 | O=C(OC1CCCCC1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7](-[OH;D1;+0:8])-[C:9]>>[C:6]-[C:7](-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:9] | 96.3 | [{"value": 96.3, "product": "C(C)(C)(C)OC(=O)N[C@H]1CC[C@H](CC1)OC(C1=CC=C(C=C1)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 2.5 | HOUR | A solution of Intermediate 35 (21.06 g), 1,1′-azobis(N,N-dimethylformamide) (64.11 g) and p-anisic acid (23.03 g, Tokyo Kasei Kogyo) in tetrahydrofuran (400 ml) was added with tri(n-butyl)phosphine (35.6 ml) at room temperature and stirred at 50° C. for 2.5 hours. The reaction mixture was cooled to room temperature, th... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary alcohol | Ester | null | null | c1ccccc1.C1CCCCC1 | HO- | C(C)(=O)OCC.O1CCCC1 | 50 | 2.5 | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](O)CC1.COc1ccc(C(=O)O)cc1>C(C)(=O)OCC.O1CCCC1>COc1ccc(C(=O)O[C@@H]2CC[C@H](NC(=O)OC(C)(C)C)CC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a30f9f819ce941d6834a0c8a1332c319 | COc1ccc(C(=O)O[C@@H]2CC[C@H](NC(=O)OC(C)(C)C)CC2)cc1>>CC(C)(C)OC(=O)N[C@@H]1CC[C@H](O)CC1 | C(C)(=O)OCC.C(C)(C)(C)OC(=O)N[C@H]1CC[C@H](CC1)OC(C1=CC=C(C=C1)OC)=O.[OH-].[Na+]>>C(C)(C)(C)OC(=O)N[C@H]1CC[C@H](CC1)O | COc1ccc(C(=O)[O:13][C@H:12]2[CH2:11][CH2:10][C@@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:15][CH2:14]2)cc1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][C@@H:12]([OH:13])[CH2:14][CH2:15]1 | COc1ccc(C(=O)O[C@@H]2CC[C@H](NC(=O)OC(C)(C)C)CC2)cc1 | CC(C)(C)OC(=O)N[C@@H]1CC[C@H](O)CC1 | null | null | CO | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | fa0d72ae7f712862012fce073f61b5242bad6a97539a947aedd819738fc0400b | 2884a5654446a5b733e7d59f144021b82bebc5565dd0ff9b32ffa054af42d6b4 | C1CCCCC1 | C-O-c1:c:c:c(-C(=O)-[O;H0;D2;+0:1]-[C:2](-[C:3])-[C:4]):c:c:1>>[C:3]-[C:2](-[OH;D1;+0:1])-[C:4] | 39.1 | [{"value": 39.1, "product": "C(C)(C)(C)OC(=O)N[C@H]1CC[C@H](CC1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 1.5 | HOUR | A solution of Intermediate 118 (32.92 g) in methanol (400 ml) was added with 3 N aqueous sodium hydroxide (163 ml) at room temperature and stirred at 50° C. for 1.5 hours. The reaction mixture was cooled to room temperature, then added with ethyl acetate (400 ml) and washed 4 times with 0.5 N aqueous sodium hydroxide (... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether | Secondary alcohol | c1ccccc1 | null | C1CCCCC1 | HO- | CO | 50 | 1.5 | COc1ccc(C(=O)O[C@@H]2CC[C@H](NC(=O)OC(C)(C)C)CC2)cc1>CO>CC(C)(C)OC(=O)N[C@@H]1CC[C@H](O)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4e85aeddbc554fecbb78e2baa0b93744 | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](Oc2cccc3cncc(Br)c23)CC1>>N[C@@H]1CC[C@@H](Oc2cccc3cncc(Br)c23)CC1 | C(C)(C)(C)OC(=O)N[C@@H]1CC[C@H](CC1)OC1=C2C(=CN=CC2=CC=C1)Br.Cl.CO>>Cl.BrC1=CN=CC2=CC=CC(=C12)O[C@@H]1CC[C@H](CC1)N | CC(C)(C)OC(=O)[NH:2][C@H:3]1[CH2:4][CH2:5][C@H:6]([O:7][c:8]2[cH:9][cH:10][cH:11][c:12]3[cH:13][n:14][cH:15][c:16]([Br:17])[c:18]23)[CH2:19][CH2:20]1>>[NH2:2][C@H:3]1[CH2:4][CH2:5][C@H:6]([O:7][c:8]2[cH:9][cH:10][cH:11][c:12]3[cH:13][n:14][cH:15][c:16]([Br:17])[c:18]23)[CH2:19][CH2:20]1 | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](Oc2cccc3cncc(Br)c23)CC1 | N[C@@H]1CC[C@@H](Oc2cccc3cncc(Br)c23)CC1 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1cc(OC2CCCCC2)c2ccncc2c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (room temperature, 2 hours) by using Intermediate 121 (49.4 mg) and 10% hydrogen chloride/methanol solution (2 ml). The solvent was evaporated under reduced pressure, and the residue was added with methanol (0.5 ml) and diethyl ether (1.5 ml). The... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | C1CCCCC1.c1ccc2cnccc2c1 | HO- | null | null | null | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](Oc2cccc3cncc(Br)c23)CC1>>N[C@@H]1CC[C@@H](Oc2cccc3cncc(Br)c23)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-77836b6fe0cb4c828f1476a14df81196 | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](Oc2cccc3cncc(Br)c23)CC1>>CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](Oc2cccc3cncc(C#N)c23)CC1 | C(C)(C)(C)OC(=O)N[C@@H]1CC[C@H](CC1)OC1=C2C(=CN=CC2=CC=C1)Br.CN(C)C=O>>C(C)(C)(C)OC(=O)N[C@@H]1CC[C@H](CC1)OC1=C2C(=CN=CC2=CC=C1)C#N | Br[c:22]1[cH:21][n:20][cH:19][c:18]2[cH:17][cH:16][cH:15][c:14]([O:13][C@H:12]3[CH2:11][CH2:10][C@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:27][CH2:26]3)[c:25]21>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([O:13][c:14]2[cH:15][cH:16][cH:17][c:18]3[cH:19... | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](Oc2cccc3cncc(Br)c23)CC1 | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](Oc2cccc3cncc(C#N)c23)CC1 | null | [C-]#N.[Zn+2].[C-]#N.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)P([C-]1C=CC=C1)C1=CC=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2] | null | Miscellaneous | OtherReaction | c64c69b6f1d81056cbac2852296bec920cfa3f25e1fe508f94c07c888647f1dc | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | c1cc(OC2CCCCC2)c2ccncc2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1:[c:7]>>[N;D1;H0:8]#[C:9]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1:[c:7] | null | [] | 120 | CELSIUS | 19 | HOUR | A suspension of Intermediate 121 (113.7 mg), zinc cyanide (19.4 mg, Wako Pure Chemical Industries), tris(dibenzylideneacetone)dipalladium(0) (24.0 mg) and 1,1′-bis(diphenylphosphino)ferrocene (35.3 mg, Tokyo Kasei Kogyo) in DMF (2 ml) was stirred at 120° C. for 19 hours. The reaction mixture was concentrated under redu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | C1CCCCC1.c1ccc2cnccc2c1 | Br- | [C-]#N.[Zn+2].[C-]#N.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)P([C-]1C=CC=C1)C1=CC=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2] | 120 | 19 | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](Oc2cccc3cncc(Br)c23)CC1>[C-]#N.[Zn+2].[C-]#N.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)P([C-]1C=CC=C1)C1=CC=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2]>CC(C)(C)OC(=O)N[C@@H]1CC[C@... |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ffa332e5c6fe43b5844f63ea4e7f138d | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](Oc2cccc3cncc(C#N)c23)CC1>>N#Cc1cncc2cccc(O[C@@H]3CC[C@@H](N)CC3)c12 | C(C)(C)(C)OC(=O)N[C@@H]1CC[C@H](CC1)OC1=C2C(=CN=CC2=CC=C1)C#N.Cl.CO>>Cl.C(#N)C1=CN=CC2=CC=CC(=C12)O[C@@H]1CC[C@H](CC1)N | CC(C)(C)OC(=O)[NH:18][C@H:17]1[CH2:16][CH2:15][C@H:14]([O:13][c:12]2[cH:11][cH:10][cH:9][c:8]3[cH:7][n:6][cH:5][c:4]([C:3]#[N:2])[c:21]32)[CH2:20][CH2:19]1>>[N:2]#[C:3][c:4]1[cH:5][n:6][cH:7][c:8]2[cH:9][cH:10][cH:11][c:12]([O:13][C@H:14]3[CH2:15][CH2:16][C@H:17]([NH2:18])[CH2:19][CH2:20]3)[c:21]12 | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](Oc2cccc3cncc(C#N)c23)CC1 | N#Cc1cncc2cccc(O[C@@H]3CC[C@@H](N)CC3)c12 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1cc(OC2CCCCC2)c2ccncc2c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (room temperature, 2 hours) by using Intermediate 122 (34.9 mg) and 10% hydrogen chloride/methanol solution (2 ml). The solvent was evaporated under reduced pressure, and the residue was added with methanol (0.5 ml) and diethyl ether (1.5 ml). The... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2cnccc2c1.C1CCCCC1 | HO- | null | null | null | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](Oc2cccc3cncc(C#N)c23)CC1>>N#Cc1cncc2cccc(O[C@@H]3CC[C@@H](N)CC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e6ea173fbdad4a93b30eaab9957c3e20 | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](Oc2cccc3cnccc23)CC1>>N[C@@H]1CC[C@@H](Oc2cccc3cnccc23)CC1 | C(C)(C)(C)OC(=O)N[C@@H]1CC[C@H](CC1)OC1=C2C=CN=CC2=CC=C1.Cl.CO>>Cl.C1=NC=CC2=C(C=CC=C12)O[C@@H]1CC[C@H](CC1)N | CC(C)(C)OC(=O)[NH:2][C@H:3]1[CH2:4][CH2:5][C@H:6]([O:7][c:8]2[cH:9][cH:10][cH:11][c:12]3[cH:13][n:14][cH:15][cH:16][c:17]23)[CH2:18][CH2:19]1>>[NH2:2][C@H:3]1[CH2:4][CH2:5][C@H:6]([O:7][c:8]2[cH:9][cH:10][cH:11][c:12]3[cH:13][n:14][cH:15][cH:16][c:17]23)[CH2:18][CH2:19]1 | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](Oc2cccc3cnccc23)CC1 | N[C@@H]1CC[C@@H](Oc2cccc3cnccc23)CC1 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1cc(OC2CCCCC2)c2ccncc2c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (room temperature, 2 hours) by using Intermediate 123 (59.6 mg) and 10% hydrogen chloride/methanol solution (2 ml). The solvent was evaporated under reduced pressure, and the residue was added with methanol (0.5 ml) and diethyl ether (1.5 ml). The... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | C1CCCCC1.c1ccc2cnccc2c1 | HO- | null | null | null | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](Oc2cccc3cnccc23)CC1>>N[C@@H]1CC[C@@H](Oc2cccc3cnccc23)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5bdc0731d83a4375b57f763a35e61dd4 | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](Oc2cccc3cncc(Br)c23)CC1.CCCC[C]([Sn])=C(CCCC)CCCC>>C=Cc1cncc2cccc(O[C@@H]3CC[C@@H](NC(=O)OC(C)(C)C)CC3)c12 | C(C)(C)(C)OC(=O)N[C@@H]1CC[C@H](CC1)OC1=C2C(=CN=CC2=CC=C1)Br.C(CCC)C(=C(CCCC)CCCC)[Sn].C(C)(C)(C)C1=CC(=CC(=C1O)C(C)(C)C)C>>C(C)(C)(C)OC(=O)N[C@@H]1CC[C@H](CC1)OC1=C2C(=CN=CC2=CC=C1)C=C | Br[c:3]1[cH:4][n:5][cH:6][c:7]2[cH:8][cH:9][cH:10][c:11]([O:12][C@H:13]3[CH2:14][CH2:15][C@H:16]([NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25][CH2:26]3)[c:27]12.CCCC[C]([Sn])=[C:2](CCCC)[CH2:1]CCC>>[CH2:1]=[CH:2][c:3]1[cH:4][n:5][cH:6][c:7]2[cH:8][cH:9][cH:10][c:11]([O:12][C@H:13]3[CH2:14][CH2... | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](Oc2cccc3cncc(Br)c23)CC1.CCCC[C]([Sn])=C(CCCC)CCCC | C=Cc1cncc2cccc(O[C@@H]3CC[C@@H](NC(=O)OC(C)(C)C)CC3)c12 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 82a3d2d8c84be82d43c962f9be2401515527412b6ecf104ee4b478759be8081e | 27ac22ec7469bd7f39cc3c50746346e388051103704091d8380f391d425a4ebf | c1cc(OC2CCCCC2)c2ccncc2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1:[c:7].C-C-C-C-[C;H0;D3;+0:8](-[CH2;D2;+0:9]-C-C-C)=[C](-[Sn])-C-C-C-C>>[CH2;D1;+0:9]=[CH;D2;+0:8]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1:[c:7] | null | [] | null | null | null | null | A solution of Intermediate 121 (500 mg), tri(n-butyl)vinyltin (518 μl, Tokyo Kasei Kogyo), tetrakis(triphenylphosphine)palladium(0) (28.1 mg) and 2,6-di-tert-butyl-p-cresol (3.2 mg, Tokyo Kasei Kogyo) in toluene (10 ml) was stirred at 110° C. for 3 hours. The solvent was evaporated under reduced pressure, and the resid... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Vinyl | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | c1ccc2cnccc2c1.C1CCCCC1 | HBr.Sn | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C | null | null | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](Oc2cccc3cncc(Br)c23)CC1.CCCC[C]([Sn])=C(CCCC)CCCC>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C>C=Cc1cncc2cccc(O[C@@H]3CC[C@@H](NC(=O)OC(C)(C)C)CC3)c... |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-98d12fb782ec41e3aba8ea2af660275d | C=Cc1cncc2cccc(O[C@@H]3CC[C@@H](NC(=O)OC(C)(C)C)CC3)c12>>C=Cc1cncc2cccc(O[C@@H]3CC[C@@H](N)CC3)c12 | C(C)(C)(C)OC(=O)N[C@@H]1CC[C@H](CC1)OC1=C2C(=CN=CC2=CC=C1)C=C.Cl.CO>>Cl.C(=C)C1=CN=CC2=CC=CC(=C12)O[C@@H]1CC[C@H](CC1)N | CC(C)(C)OC(=O)[NH:17][C@H:16]1[CH2:15][CH2:14][C@H:13]([O:12][c:11]2[cH:10][cH:9][cH:8][c:7]3[cH:6][n:5][cH:4][c:3]([CH:2]=[CH2:1])[c:20]32)[CH2:19][CH2:18]1>>[CH2:1]=[CH:2][c:3]1[cH:4][n:5][cH:6][c:7]2[cH:8][cH:9][cH:10][c:11]([O:12][C@H:13]3[CH2:14][CH2:15][C@H:16]([NH2:17])[CH2:18][CH2:19]3)[c:20]12 | C=Cc1cncc2cccc(O[C@@H]3CC[C@@H](NC(=O)OC(C)(C)C)CC3)c12 | C=Cc1cncc2cccc(O[C@@H]3CC[C@@H](N)CC3)c12 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1cc(OC2CCCCC2)c2ccncc2c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (room temperature, 2 hours) by using Intermediate 124 (83.9 mg) and 10% hydrogen chloride/methanol solution (2 ml). The solvent was evaporated under reduced pressure, and the residue was added with methanol (0.5 ml) and diethyl ether (1.5 ml). The... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2cnccc2c1.C1CCCCC1 | HO- | null | null | null | C=Cc1cncc2cccc(O[C@@H]3CC[C@@H](NC(=O)OC(C)(C)C)CC3)c12>>C=Cc1cncc2cccc(O[C@@H]3CC[C@@H](N)CC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3b14aa01c68746f3962bb1931c60dfc0 | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](Oc2cccc3cncc(Br)c23)CC1.N>>CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](Oc2cccc3cncc(N)c23)CC1 | C(C)(C)(C)OC(=O)N[C@@H]1CC[C@H](CC1)OC1=C2C(=CN=CC2=CC=C1)Br.C(C)(C)(C)P(C1=C(C=CC=C1)C1=CC=CC=C1)C(C)(C)C.CC(C)([O-])C.[Na+].N.O1CCOCC1>>C(C)(C)(C)OC(=O)N[C@@H]1CC[C@H](CC1)OC1=C2C(=CN=CC2=CC=C1)N | Br[c:22]1[cH:21][n:20][cH:19][c:18]2[cH:17][cH:16][cH:15][c:14]([O:13][C@H:12]3[CH2:11][CH2:10][C@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:26][CH2:25]3)[c:24]21.[NH3:23]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([O:13][c:14]2[cH:15][cH:16][cH:17][c:1... | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](Oc2cccc3cncc(Br)c23)CC1.N | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](Oc2cccc3cncc(N)c23)CC1 | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | null | Heteroatom Alkylation and Arylation | OtherReaction | 261fd9f972974897261ca5eac8b1086caae005655bedee979c411e5b22857ba2 | c5668f64a1395fa45312378ed819baaeafc354cdb673b20226ea2853ed14db5d | c1cc(OC2CCCCC2)c2ccncc2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1:[c:7].[NH3;D0;+0:8]>>[NH2;D1;+0:8]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1:[c:7] | null | [] | 70 | CELSIUS | 22 | HOUR | A suspension of Intermediate 121 (100 mg), tris(dibenzylideneacetone)dipalladium(0) (22.1 mg), 2-(di-tert-butylphosphino)biphenyl (33.9 mg) and sodium tert-butoxide (35.3 mg) in 0.5 N ammonia/dioxane solution (2 ml) was stirred at 70° C. for 22 hours. The reaction mixture was filtered through a Celite layer, and the so... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Primary amine | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | C1CCCCC1.c1ccc2cnccc2c1 | HBr | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | 70 | 22 | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](Oc2cccc3cncc(Br)c23)CC1.N>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]>CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](Oc2cccc3cncc(N)c23)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0a8d964313a1439fa4e37fff40891b87 | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](Oc2cccc3cncc(N)c23)CC1>>Nc1cncc2cccc(O[C@@H]3CC[C@@H](N)CC3)c12 | C(C)(C)(C)OC(=O)N[C@@H]1CC[C@H](CC1)OC1=C2C(=CN=CC2=CC=C1)N.Cl.CO>>Cl.NC1=CN=CC2=CC=CC(=C12)O[C@@H]1CC[C@H](CC1)N | CC(C)(C)OC(=O)[NH:17][C@H:16]1[CH2:15][CH2:14][C@H:13]([O:12][c:11]2[cH:10][cH:9][cH:8][c:7]3[cH:6][n:5][cH:4][c:3]([NH2:2])[c:20]32)[CH2:19][CH2:18]1>>[NH2:2][c:3]1[cH:4][n:5][cH:6][c:7]2[cH:8][cH:9][cH:10][c:11]([O:12][C@H:13]3[CH2:14][CH2:15][C@H:16]([NH2:17])[CH2:18][CH2:19]3)[c:20]12 | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](Oc2cccc3cncc(N)c23)CC1 | Nc1cncc2cccc(O[C@@H]3CC[C@@H](N)CC3)c12 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1cc(OC2CCCCC2)c2ccncc2c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (room temperature, 8 hours) by using Intermediate 125 (36.1 mg) and 10% hydrogen chloride/methanol solution (2 ml). The solvent was evaporated under reduced pressure, and the residue was added with methanol (0.5 ml) and diethyl ether (1.5 ml). The... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2cnccc2c1.C1CCCCC1 | HO- | null | null | null | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](Oc2cccc3cncc(N)c23)CC1>>Nc1cncc2cccc(O[C@@H]3CC[C@@H](N)CC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-41aab4904af540338d435ca329ed8c84 | C=Cc1cncc2cccc(O[C@@H]3CC[C@@H](NC(=O)OC(C)(C)C)CC3)c12>>CCc1cncc2cccc(O[C@@H]3CC[C@@H](NC(=O)OC(C)(C)C)CC3)c12 | C(C)(C)(C)OC(=O)N[C@@H]1CC[C@H](CC1)OC1=C2C(=CN=CC2=CC=C1)C=C>>C(C)(C)(C)OC(=O)N[C@@H]1CC[C@H](CC1)OC1=C2C(=CN=CC2=CC=C1)CC | [CH2:1]=[CH:2][c:3]1[cH:4][n:5][cH:6][c:7]2[cH:8][cH:9][cH:10][c:11]([O:12][C@H:13]3[CH2:14][CH2:15][C@H:16]([NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25][CH2:26]3)[c:27]12>>[CH3:1][CH2:2][c:3]1[cH:4][n:5][cH:6][c:7]2[cH:8][cH:9][cH:10][c:11]([O:12][C@H:13]3[CH2:14][CH2:15][C@H:16]([NH:17][C:1... | C=Cc1cncc2cccc(O[C@@H]3CC[C@@H](NC(=O)OC(C)(C)C)CC3)c12 | CCc1cncc2cccc(O[C@@H]3CC[C@@H](NC(=O)OC(C)(C)C)CC3)c12 | null | [Pt]=O | CO | Reduction | Hydrogenation (double to single) | 8276b4fb5ddc7d15dec6d92474e91e2dbb2fb8b81e5b5720762e5d89cb27aa69 | 1ccae9f2e86499601fc3421041ff4588c8e6fd53048e86c3b6ed12ae873609c0 | c1cc(OC2CCCCC2)c2ccncc2c1 | [CH2;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7]>>[CH3;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | 45.2 | [{"value": 45.2, "product": "C(C)(C)(C)OC(=O)N[C@@H]1CC[C@H](CC1)OC1=C2C(=CN=CC2=CC=C1)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | A solution of Intermediate 124 (90.5 mg) in methanol (5 ml) was added with platinum oxide (13 mg, Wako Pure Chemical Industries) and stirred for 15 hours under hydrogen atmosphere. The reaction mixture was filtered through a Celite layer, and the solvent was evaporated under reduced pressure. Then, the residue was puri... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | null | null | null | c1ccc2cnccc2c1.C1CCCCC1 | null | [Pt]=O.CO | null | 15 | C=Cc1cncc2cccc(O[C@@H]3CC[C@@H](NC(=O)OC(C)(C)C)CC3)c12>[Pt]=O.CO>CCc1cncc2cccc(O[C@@H]3CC[C@@H](NC(=O)OC(C)(C)C)CC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fe97f6283c664643b9936311d55bf07e | CCc1cncc2cccc(O[C@@H]3CC[C@@H](NC(=O)OC(C)(C)C)CC3)c12>>CCc1cncc2cccc(O[C@@H]3CC[C@@H](N)CC3)c12 | C(C)(C)(C)OC(=O)N[C@@H]1CC[C@H](CC1)OC1=C2C(=CN=CC2=CC=C1)CC.Cl.CO>>Cl.C(C)C1=CN=CC2=CC=CC(=C12)O[C@@H]1CC[C@H](CC1)N | CC(C)(C)OC(=O)[NH:17][C@H:16]1[CH2:15][CH2:14][C@H:13]([O:12][c:11]2[cH:10][cH:9][cH:8][c:7]3[cH:6][n:5][cH:4][c:3]([CH2:2][CH3:1])[c:20]32)[CH2:19][CH2:18]1>>[CH3:1][CH2:2][c:3]1[cH:4][n:5][cH:6][c:7]2[cH:8][cH:9][cH:10][c:11]([O:12][C@H:13]3[CH2:14][CH2:15][C@H:16]([NH2:17])[CH2:18][CH2:19]3)[c:20]12 | CCc1cncc2cccc(O[C@@H]3CC[C@@H](NC(=O)OC(C)(C)C)CC3)c12 | CCc1cncc2cccc(O[C@@H]3CC[C@@H](N)CC3)c12 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1cc(OC2CCCCC2)c2ccncc2c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (room temperature, 2 hours) by using Intermediate 126 (41.1 mg) and 10% hydrogen chloride/methanol solution (2 ml). The solvent was evaporated under reduced pressure, and the residue was added with methanol (0.5 ml) and diethyl ether (1.5 ml). The... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2cnccc2c1.C1CCCCC1 | HO- | null | null | null | CCc1cncc2cccc(O[C@@H]3CC[C@@H](NC(=O)OC(C)(C)C)CC3)c12>>CCc1cncc2cccc(O[C@@H]3CC[C@@H](N)CC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-390a66a2058b4bf8bb6c50b5617ecc7b | Cc1cncc2cccc(N)c12>>Cc1cncc2cccc(O)c12 | N.O.CC1=CN=CC2=CC=CC(=C12)N.N(=O)[O-].[Na+]>>CC1=CN=CC2=CC=CC(=C12)O | N[c:10]1[cH:9][cH:8][cH:7][c:6]2[cH:5][n:4][cH:3][c:2]([CH3:1])[c:12]21>>[CH3:1][c:2]1[cH:3][n:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([OH:11])[c:12]12 | Cc1cncc2cccc(N)c12 | Cc1cncc2cccc(O)c12 | null | null | S(O)(O)(=O)=O | Functional Group Interconversion | OtherReaction | a9e88b40d19f980e8c4fbfcb1a8796d8357e51f33faec4808ce28ecbc2beaf88 | ed7617b9cd113fcbf3232da782e35483fef55189a64648ab4bdbc41767cd9a80 | c1ccc2cnccc2c1 | N-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1>>[O;D1;H1:10]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1 | 63.9 | [{"value": 63.9, "product": "CC1=CN=CC2=CC=CC(=C12)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-methyl-5-aminoisoquinoline (869 mg) in concentrated sulfuric acid (8 ml) was added with sodium nitrite (379 mg) with ice cooling and stirring and stirred for 0.5 hours. The reaction mixture was added with water (12 ml) and then stirred at 130° C. for 16 hours. The reaction mixture was neutralized with 2... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic alcohol | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | null | S(O)(O)(=O)=O | null | null | Cc1cncc2cccc(N)c12>S(O)(O)(=O)=O>Cc1cncc2cccc(O)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e0052dc7514340f6aa87ab5a0aa5366d | Cc1cncc2cccc(OC3CCN(C(=O)OC(C)(C)C)CC3)c12>>Cc1cncc2cccc(OC3CCNCC3)c12 | CC1=CN=CC2=CC=CC(=C12)OC1CCN(CC1)C(=O)OC(C)(C)C.Cl.CO>>Cl.CC1=CN=CC2=CC=CC(=C12)OC1CCNCC1 | CC(C)(C)OC(=O)[N:15]1[CH2:14][CH2:13][CH:12]([O:11][c:10]2[cH:9][cH:8][cH:7][c:6]3[cH:5][n:4][cH:3][c:2]([CH3:1])[c:18]32)[CH2:17][CH2:16]1>>[CH3:1][c:2]1[cH:3][n:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([O:11][CH:12]3[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]3)[c:18]12 | Cc1cncc2cccc(OC3CCN(C(=O)OC(C)(C)C)CC3)c12 | Cc1cncc2cccc(OC3CCNCC3)c12 | null | null | null | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1cc(OC2CCNCC2)c2ccncc2c1 | 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] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (room temperature, 2 hours) by using Intermediate 128 (604 mg) and 10% hydrogen chloride/methanol solution (20 ml). The solvent was evaporated under reduced pressure, and the residue was added with methanol (5 ml) and diethyl ether (15 ml). The de... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccc2cnccc2c1.C1CCNCC1 | HO- | null | null | null | Cc1cncc2cccc(OC3CCN(C(=O)OC(C)(C)C)CC3)c12>>Cc1cncc2cccc(OC3CCNCC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f7de456d2ad64a3cbc0a43f8d6ff3aa7 | Cc1cncc2cccc(O[C@@H]3CC[C@@H](NC(=O)OC(C)(C)C)CC3)c12>>Cc1cncc2cccc(O[C@@H]3CC[C@@H](N)CC3)c12 | C(C)(C)(C)OC(=O)N[C@@H]1CC[C@H](CC1)OC1=C2C(=CN=CC2=CC=C1)C.Cl.CO>>Cl.CC1=CN=CC2=CC=CC(=C12)O[C@@H]1CC[C@H](CC1)N | CC(C)(C)OC(=O)[NH:16][C@H:15]1[CH2:14][CH2:13][C@H:12]([O:11][c:10]2[cH:9][cH:8][cH:7][c:6]3[cH:5][n:4][cH:3][c:2]([CH3:1])[c:19]32)[CH2:18][CH2:17]1>>[CH3:1][c:2]1[cH:3][n:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([O:11][C@H:12]3[CH2:13][CH2:14][C@H:15]([NH2:16])[CH2:17][CH2:18]3)[c:19]12 | Cc1cncc2cccc(O[C@@H]3CC[C@@H](NC(=O)OC(C)(C)C)CC3)c12 | Cc1cncc2cccc(O[C@@H]3CC[C@@H](N)CC3)c12 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1cc(OC2CCCCC2)c2ccncc2c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (room temperature, 2 hours) by using Intermediate 129 (194 mg) and 10% hydrogen chloride/methanol solution (3.5 ml). The solvent was evaporated under reduced pressure, and the residue was added with methanol (1 ml) and diethyl ether (3 ml). The de... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2cnccc2c1.C1CCCCC1 | HO- | null | null | null | Cc1cncc2cccc(O[C@@H]3CC[C@@H](NC(=O)OC(C)(C)C)CC3)c12>>Cc1cncc2cccc(O[C@@H]3CC[C@@H](N)CC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3dfa3be4800f47328a373a2f1c6c78bb | CC(C)(C)OC(=O)N[C@H]1CC[C@@H](Oc2cccc3c(Cl)nccc23)CC1.N>>CC(C)(C)OC(=O)N[C@H]1CC[C@@H](Oc2cccc3c(N)nccc23)CC1 | C(C)(C)(C)OC(=O)N[C@@H]1CC[C@@H](CC1)OC1=C2C=CN=C(C2=CC=C1)Cl.N>>C(C)(C)(C)OC(=O)N[C@@H]1CC[C@@H](CC1)OC1=C2C=CN=C(C2=CC=C1)N | Cl[c:19]1[c:18]2[cH:17][cH:16][cH:15][c:14]([O:13][C@@H:12]3[CH2:11][CH2:10][C@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:26][CH2:25]3)[c:24]2[cH:23][cH:22][n:21]1.[NH3:20]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][C@@H:12]([O:13][c:14]2[cH:15][cH:16][cH:17][c... | CC(C)(C)OC(=O)N[C@H]1CC[C@@H](Oc2cccc3c(Cl)nccc23)CC1.N | CC(C)(C)OC(=O)N[C@H]1CC[C@@H](Oc2cccc3c(N)nccc23)CC1 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 261fd9f972974897261ca5eac8b1086caae005655bedee979c411e5b22857ba2 | c5668f64a1395fa45312378ed819baaeafc354cdb673b20226ea2853ed14db5d | c1cc(OC2CCCCC2)c2ccncc2c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5]):[c:6].[NH3;D0;+0:7]>>[NH2;D1;+0:7]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5]):[c:6] | null | [] | 150 | CELSIUS | 20 | HOUR | A solution of Intermediate 130 (500 mg) in dioxane (2.5 ml) was added with 28% aqueous ammonia solution (2.5 ml) and stirred at 150° C. for 20 hours in a sealed tube. The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The residue was added with dioxane (6 ml... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Primary amine | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | C1CCCCC1.c1ccc2cnccc2c1 | HCl | O1CCOCC1 | 150 | 20 | CC(C)(C)OC(=O)N[C@H]1CC[C@@H](Oc2cccc3c(Cl)nccc23)CC1.N>O1CCOCC1>CC(C)(C)OC(=O)N[C@H]1CC[C@@H](Oc2cccc3c(N)nccc23)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4a4d632386d0470bab934e0fc7ebc05f | CC(C)(C)OC(=O)N[C@H]1CC[C@@H](Oc2cccc3c(N)nccc23)CC1>>Nc1nccc2c(O[C@@H]3CC[C@H](N)CC3)cccc12 | C(C)(C)(C)OC(=O)N[C@@H]1CC[C@@H](CC1)OC1=C2C=CN=C(C2=CC=C1)N.Cl.CO>>Cl.NC1=NC=CC2=C(C=CC=C12)O[C@H]1CC[C@H](CC1)N | CC(C)(C)OC(=O)[NH:14][C@H:13]1[CH2:12][CH2:11][C@@H:10]([O:9][c:8]2[c:7]3[cH:6][cH:5][n:4][c:3]([NH2:2])[c:20]3[cH:19][cH:18][cH:17]2)[CH2:16][CH2:15]1>>[NH2:2][c:3]1[n:4][cH:5][cH:6][c:7]2[c:8]([O:9][C@H:10]3[CH2:11][CH2:12][C@@H:13]([NH2:14])[CH2:15][CH2:16]3)[cH:17][cH:18][cH:19][c:20]12 | CC(C)(C)OC(=O)N[C@H]1CC[C@@H](Oc2cccc3c(N)nccc23)CC1 | Nc1nccc2c(O[C@@H]3CC[C@H](N)CC3)cccc12 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1cc(OC2CCCCC2)c2ccncc2c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (room temperature, 2 hours) by using Intermediate 131 (76 mg) and 10% hydrogen chloride/methanol solution (2 ml). The solvent was evaporated under reduced pressure, and the residue was added with methanol (1 ml) and diethyl ether (3 ml). The depos... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | C1CCCCC1.c1ccc2cnccc2c1 | HO- | null | null | null | CC(C)(C)OC(=O)N[C@H]1CC[C@@H](Oc2cccc3c(N)nccc23)CC1>>Nc1nccc2c(O[C@@H]3CC[C@H](N)CC3)cccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d189c45fbcf042a78bf55612f254a951 | CC(C)(C)OC(=O)N1CCC(Nc2cccc3c(Cl)nccc23)CC1.COc1ccc(CN)cc1>>COc1ccc(CNc2nccc3c(NC4CCN(C(=O)OC(C)(C)C)CC4)cccc23)cc1 | ClC1=NC=CC2=C(C=CC=C12)NC1CCN(CC1)C(=O)OC(C)(C)C.COC1=CC=C(CN)C=C1.C(C)(C)(C)P(C1=C(C=CC=C1)C1=CC=CC=C1)C(C)(C)C.CC(C)([O-])C.[Na+]>>COC1=CC=C(CNC2=NC=CC3=C(C=CC=C23)NC2CCN(CC2)C(=O)OC(C)(C)C)C=C1 | Cl[c:9]1[n:10][cH:11][cH:12][c:13]2[c:14]([NH:15][CH:16]3[CH2:17][CH2:18][N:19]([C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[CH2:27][CH2:28]3)[cH:29][cH:30][cH:31][c:32]12.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][NH2:8])[cH:33][cH:34]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][NH:8][c:9]2[n:10][cH:11]... | CC(C)(C)OC(=O)N1CCC(Nc2cccc3c(Cl)nccc23)CC1.COc1ccc(CN)cc1 | COc1ccc(CNc2nccc3c(NC4CCN(C(=O)OC(C)(C)C)CC4)cccc23)cc1 | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 17c3dbb58f19c559a89452c2c52a32d81319b5dd6d11e225611cc478eba61c1b | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2nccc3c(NC4CCNCC4)cccc23)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[C:8]-[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[C:8]-[c:9]):[c:4](:[c:5]):[c:6] | null | [] | 70 | CELSIUS | 1 | HOUR | A suspension of Intermediate 84 (235 mg), 4-methoxybenzylamine (110 μl), tris(dibenzylideneacetone)dipalladium(0) (30.4 mg), 2-(di-tert-butylphosphino)biphenyl (41.0 mg) and sodium tert-butoxide (93.6 mg) in toluene (4.5 ml) was stirred at 70° C. for 1 hour. The reaction mixture was filtered through a Celite layer, and... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | c1ccccc1.C1CC[NH]CC1.c1ccc2cnccc2c1 | HCl | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)C | 70 | 1 | CC(C)(C)OC(=O)N1CCC(Nc2cccc3c(Cl)nccc23)CC1.COc1ccc(CN)cc1>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)C>COc1ccc(CNc2nccc3c(NC4CCN(C(=O)OC(C)(C)C)CC4)cccc23)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b3e1fac3b5b54f7b92bfe077e81f3e7b | COc1ccc(CNc2nccc3c(NC4CCN(C(=O)OC(C)(C)C)CC4)cccc23)cc1>>CC(C)(C)OC(=O)N1CCC(Nc2cccc3c(N)nccc23)CC1 | COC1=CC=C(CNC2=NC=CC3=C(C=CC=C23)NC2CCN(CC2)C(=O)OC(C)(C)C)C=C1>>NC1=NC=CC2=C(C=CC=C12)NC1CCN(CC1)C(=O)OC(C)(C)C | COc1ccc(C[NH:19][c:18]2[c:17]3[cH:16][cH:15][cH:14][c:13]([NH:12][CH:11]4[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:25][CH2:24]4)[c:23]3[cH:22][cH:21][n:20]2)cc1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([NH:12][c:13]2[cH:14][cH:15][cH:16][c:17]3[c:18]... | COc1ccc(CNc2nccc3c(NC4CCN(C(=O)OC(C)(C)C)CC4)cccc23)cc1 | CC(C)(C)OC(=O)N1CCC(Nc2cccc3c(N)nccc23)CC1 | null | null | FC(C(=O)O)(F)F | Reduction | OtherReaction | bd6cc2ddd30b209c36eb43f9e2d163a4da40f8a48bda8b578aa13caf5d4fe5dd | 79272555d5bd71219cf9e8b42c4ac12a30bbf383c58cfbccf49a5a990e3653c1 | c1cc(NC2CCNCC2)c2ccncc2c1 | C-O-c1:c:c:c(-C-[NH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5]):c:c:1>>[NH2;D1;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | 99.6 | [{"value": 99.6, "product": "NC1=NC=CC2=C(C=CC=C12)NC1CCN(CC1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of Intermediate 132 (270 mg) in 95% trifluoroacetic acid (5 ml) was stirred at 50° C. for 16 hours, and the solvent was evaporated under reduced pressure. The residue was added with dioxane (3 ml), 2 N aqueous sodium hydroxide (1 ml) and 2 di-t-butyl dicarbonate (393 mg) and stirred at room temperature for 1... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Primary amine | c1ccccc1 | null | C1CC[NH]CC1.c1ccc2cnccc2c1 | HO- | FC(C(=O)O)(F)F | null | 1 | COc1ccc(CNc2nccc3c(NC4CCN(C(=O)OC(C)(C)C)CC4)cccc23)cc1>FC(C(=O)O)(F)F>CC(C)(C)OC(=O)N1CCC(Nc2cccc3c(N)nccc23)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6a29741c4a614edab796fa123e380462 | CC(C)(C)OC(=O)N1CCC(Nc2cccc3c(N)nccc23)CC1>>Nc1nccc2c(NC3CCNCC3)cccc12 | NC1=NC=CC2=C(C=CC=C12)NC1CCN(CC1)C(=O)OC(C)(C)C.Cl.CO>>NC1=NC=CC2=C(C=CC=C12)NC1CCNCC1 | CC(C)(C)OC(=O)[N:12]1[CH2:11][CH2:10][CH:9]([NH:8][c:7]2[c:6]3[cH:5][cH:4][n:3][c:2]([NH2:1])[c:18]3[cH:17][cH:16][cH:15]2)[CH2:14][CH2:13]1>>[NH2:1][c:2]1[n:3][cH:4][cH:5][c:6]2[c:7]([NH:8][CH:9]3[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]3)[cH:15][cH:16][cH:17][c:18]12 | CC(C)(C)OC(=O)N1CCC(Nc2cccc3c(N)nccc23)CC1 | Nc1nccc2c(NC3CCNCC3)cccc12 | null | null | null | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1cc(NC2CCNCC2)c2ccncc2c1 | 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] | 71.7 | [{"value": 71.7, "product": "NC1=NC=CC2=C(C=CC=C12)NC1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (room temperature, 2 hours) by using Intermediate 133 (199 mg) and 10% hydrogen chloride/methanol solution (3 ml). The solvent was evaporated under reduced pressure, and the residue was added with methanol (1 ml) and diethyl ether (3 ml). The depo... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | C1CCNCC1.c1ccc2cnccc2c1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCC(Nc2cccc3c(N)nccc23)CC1>>Nc1nccc2c(NC3CCNCC3)cccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-89e65fdcf54141689ca1a566dc61bce4 | BrCCOC1CCCCO1.c1cc(NC2CCNCC2)c2ccncc2c1>>c1cc(NC2CCN(CCOC3CCCCO3)CC2)c2ccncc2c1 | CC(=O)C.Cl.C1=NC=CC2=C(C=CC=C12)NC1CCNCC1.C([O-])([O-])=O.[K+].[K+].BrCCOC1OCCCC1>>O1C(CCCC1)OCCN1CCC(CC1)NC1=C2C=CN=CC2=CC=C1 | Br[CH2:9][CH2:10][O:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][O:17]1.[cH:1]1[cH:2][c:3]([NH:4][CH:5]2[CH2:6][CH2:7][NH:8][CH2:18][CH2:19]2)[c:20]2[cH:21][cH:22][n:23][cH:24][c:25]2[cH:26]1>>[cH:1]1[cH:2][c:3]([NH:4][CH:5]2[CH2:6][CH2:7][N:8]([CH2:9][CH2:10][O:11][CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16][O:17]3)[CH2:18... | BrCCOC1CCCCO1.c1cc(NC2CCNCC2)c2ccncc2c1 | c1cc(NC2CCN(CCOC3CCCCO3)CC2)c2ccncc2c1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cc(NC2CCN(CCOC3CCCCO3)CC2)c2ccncc2c1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | null | [] | null | null | 48 | HOUR | A suspension of the compound of Example 20 (70 mg) and potassium carbonate (142 mg, Kokusan Chemical) in N,N-dimethylformamide (1.5 ml) was added with 2-(2-bromoethoxy)tetrahydro-2H-pyran (254 μl, Aldrich) and stirred at room temperature for 48 hours. The reaction mixture was added with acetone (10 ml), and insoluble m... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.C1CCOCC1.c1ccc2cnccc2c1 | HBr | CN(C=O)C | null | 48 | BrCCOC1CCCCO1.c1cc(NC2CCNCC2)c2ccncc2c1>CN(C=O)C>c1cc(NC2CCN(CCOC3CCCCO3)CC2)c2ccncc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d00bddfa7b8a4ef6b23783ff72234805 | BrCCOC1CCCCO1.Cc1cncc2cccc(NC3CCNCC3)c12>>Cc1cncc2cccc(NC3CCN(CCO)CC3)c12 | BrCCOC1OCCCC1.Cl.CC1=CN=CC2=CC=CC(=C12)NC1CCNCC1>>Cl.OCCN1CCC(CC1)NC1=C2C(=CN=CC2=CC=C1)C | Br[CH2:16][CH2:17][O:18]C1CCCCO1.[CH3:1][c:2]1[cH:3][n:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([NH:11][CH:12]3[CH2:13][CH2:14][NH:15][CH2:19][CH2:20]3)[c:21]12>>[CH3:1][c:2]1[cH:3][n:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([NH:11][CH:12]3[CH2:13][CH2:14][N:15]([CH2:16][CH2:17][OH:18])[CH2:19][CH2:20]3)[c:21]12 | BrCCOC1CCCCO1.Cc1cncc2cccc(NC3CCNCC3)c12 | Cc1cncc2cccc(NC3CCN(CCO)CC3)c12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 92200bde28dedcd3add4f003e7f20d31008c8f0aca8f36d973aa94d011837799 | 0690078e74c557718340a96e117e2023ca0662eb2b391d9d3661cf44ee04bb0c | c1cc(NC2CCNCC2)c2ccncc2c1 | Br-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-C1-C-C-C-C-O-1.[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]-[OH;D1;+0:3])-[C:7]-[C:8] | null | [] | null | null | null | null | According to the method of Example 144, an alkylation reaction with 2-(2-bromoethoxy)tetrahydro-2H-pyran and a deprotection reaction were performed by using the compound of Example 106 to obtain the title compound.
Conditions: See reaction.notes.procedure_details.
Workup: a deprotection reaction | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Ether.Secondary amine | Primary alcohol.Tertiary amine | C1CCOCC1.C1CCNCC1 | C1CC[NH]CC1 | c1ccc2cnccc2c1.C1CC[NH]CC1 | HBr | null | null | null | BrCCOC1CCCCO1.Cc1cncc2cccc(NC3CCNCC3)c12>>Cc1cncc2cccc(NC3CCN(CCO)CC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ff1c7dcd2ff349b5ac91cf5866601436 | BrCCOC1CCCCO1.N[C@@H]1CC[C@@H](Nc2cccc3cnccc23)CC1>>OCCN[C@@H]1CC[C@@H](Nc2cccc3cnccc23)CC1 | BrCCOC1OCCCC1.Cl.C1=NC=CC2=C(C=CC=C12)N[C@@H]1CC[C@H](CC1)N>>Cl.C1=NC=CC2=C(C=CC=C12)N[C@@H]1CC[C@H](CC1)NCCO | Br[CH2:4][CH2:3][O:2]C1CCCCO1.[NH2:5][C@H:6]1[CH2:7][CH2:8][C@H:9]([NH:10][c:11]2[cH:12][cH:13][cH:14][c:15]3[cH:16][n:17][cH:18][cH:19][c:20]23)[CH2:21][CH2:22]1>>[OH:2][CH2:3][CH2:4][NH:5][C@H:6]1[CH2:7][CH2:8][C@H:9]([NH:10][c:11]2[cH:12][cH:13][cH:14][c:15]3[cH:16][n:17][cH:18][cH:19][c:20]23)[CH2:21][CH2:22]1 | BrCCOC1CCCCO1.N[C@@H]1CC[C@@H](Nc2cccc3cnccc23)CC1 | OCCN[C@@H]1CC[C@@H](Nc2cccc3cnccc23)CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | ea5e2ef01067c3bff8f2185e9a1c85d176cf6a06653e5daa7dff2663a74ade66 | 9a9b1b205eb0298199862d313a9ef714203a0350cfdb128705dab974552275be | c1cc(NC2CCCCC2)c2ccncc2c1 | Br-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-C1-C-C-C-C-O-1.[C:4]-[C:5](-[NH2;D1;+0:6])-[C:7]>>[C:4]-[C:5](-[NH;D2;+0:6]-[CH2;D2;+0:1]-[C:2]-[OH;D1;+0:3])-[C:7] | null | [] | null | null | null | null | According to the method of Example 144, an alkylation reaction with 2-(2-bromoethoxy)tetrahydro-2H-pyran and a deprotection reaction were performed by using the compound of Example 24 to obtain the title compound.
Conditions: See reaction.notes.procedure_details.
Workup: a deprotection reaction | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Ether.Primary amine | Primary alcohol.Secondary amine | C1CCOCC1 | null | C1CCCCC1.c1ccc2cnccc2c1 | HBr | null | null | null | BrCCOC1CCCCO1.N[C@@H]1CC[C@@H](Nc2cccc3cnccc23)CC1>>OCCN[C@@H]1CC[C@@H](Nc2cccc3cnccc23)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c1f2ade017504966a4c64c8770e8d573 | BrCCOC1CCCCO1.Cc1cncc2cccc(N[C@@H]3CC[C@@H](N)CC3)c12>>Cc1cncc2cccc(N[C@@H]3CC[C@@H](NCCO)CC3)c12 | BrCCOC1OCCCC1.Cl.CC1=CN=CC2=CC=CC(=C12)N[C@@H]1CC[C@H](CC1)N>>Cl.CC1=CN=CC2=CC=CC(=C12)N[C@@H]1CC[C@H](CC1)NCCO | Br[CH2:17][CH2:18][O:19]C1CCCCO1.[CH3:1][c:2]1[cH:3][n:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([NH:11][C@H:12]3[CH2:13][CH2:14][C@H:15]([NH2:16])[CH2:20][CH2:21]3)[c:22]12>>[CH3:1][c:2]1[cH:3][n:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([NH:11][C@H:12]3[CH2:13][CH2:14][C@H:15]([NH:16][CH2:17][CH2:18][OH:19])[CH2:20][CH2:21... | BrCCOC1CCCCO1.Cc1cncc2cccc(N[C@@H]3CC[C@@H](N)CC3)c12 | Cc1cncc2cccc(N[C@@H]3CC[C@@H](NCCO)CC3)c12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | ea5e2ef01067c3bff8f2185e9a1c85d176cf6a06653e5daa7dff2663a74ade66 | 9a9b1b205eb0298199862d313a9ef714203a0350cfdb128705dab974552275be | c1cc(NC2CCCCC2)c2ccncc2c1 | Br-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-C1-C-C-C-C-O-1.[C:4]-[C:5](-[NH2;D1;+0:6])-[C:7]>>[C:4]-[C:5](-[NH;D2;+0:6]-[CH2;D2;+0:1]-[C:2]-[OH;D1;+0:3])-[C:7] | null | [] | null | null | null | null | According to the method of Example 144, an alkylation reaction with 2-(2-bromoethoxy)tetrahydro-2H-pyran and a deprotection reaction were performed by using the compound of Example 121 to obtain the title compound.
Conditions: See reaction.notes.procedure_details.
Workup: a deprotection reaction | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Ether.Primary amine | Primary alcohol.Secondary amine | C1CCOCC1 | null | c1ccc2cnccc2c1.C1CCCCC1 | HBr | null | null | null | BrCCOC1CCCCO1.Cc1cncc2cccc(N[C@@H]3CC[C@@H](N)CC3)c12>>Cc1cncc2cccc(N[C@@H]3CC[C@@H](NCCO)CC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f848c0cd70984334a629a40bca364c48 | BrCCOC1CCCCO1.N[C@H]1CC[C@@H](Nc2cccc3cnccc23)CC1>>OCCN[C@H]1CC[C@@H](Nc2cccc3cnccc23)CC1 | BrCCOC1OCCCC1.Cl.C1=NC=CC2=C(C=CC=C12)N[C@@H]1CC[C@@H](CC1)N>>Cl.C1=NC=CC2=C(C=CC=C12)N[C@@H]1CC[C@@H](CC1)NCCO | Br[CH2:4][CH2:3][O:2]C1CCCCO1.[NH2:5][C@H:6]1[CH2:7][CH2:8][C@@H:9]([NH:10][c:11]2[cH:12][cH:13][cH:14][c:15]3[cH:16][n:17][cH:18][cH:19][c:20]23)[CH2:21][CH2:22]1>>[OH:2][CH2:3][CH2:4][NH:5][C@H:6]1[CH2:7][CH2:8][C@@H:9]([NH:10][c:11]2[cH:12][cH:13][cH:14][c:15]3[cH:16][n:17][cH:18][cH:19][c:20]23)[CH2:21][CH2:22]1 | BrCCOC1CCCCO1.N[C@H]1CC[C@@H](Nc2cccc3cnccc23)CC1 | OCCN[C@H]1CC[C@@H](Nc2cccc3cnccc23)CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | ea5e2ef01067c3bff8f2185e9a1c85d176cf6a06653e5daa7dff2663a74ade66 | 9a9b1b205eb0298199862d313a9ef714203a0350cfdb128705dab974552275be | c1cc(NC2CCCCC2)c2ccncc2c1 | Br-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-C1-C-C-C-C-O-1.[C:4]-[C:5](-[NH2;D1;+0:6])-[C:7]>>[C:4]-[C:5](-[NH;D2;+0:6]-[CH2;D2;+0:1]-[C:2]-[OH;D1;+0:3])-[C:7] | null | [] | null | null | null | null | According to the method of Example 144, an alkylation reaction with 2-(2-bromoethoxy)tetrahydro-2H-pyran and a deprotection reaction were performed by using the compound of Example 23 to obtain the title compound.
Conditions: See reaction.notes.procedure_details.
Workup: a deprotection reaction | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Ether.Primary amine | Primary alcohol.Secondary amine | C1CCOCC1 | null | C1CCCCC1.c1ccc2cnccc2c1 | HBr | null | null | null | BrCCOC1CCCCO1.N[C@H]1CC[C@@H](Nc2cccc3cnccc23)CC1>>OCCN[C@H]1CC[C@@H](Nc2cccc3cnccc23)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-aa44ef0c05ad4a6ba243340aa196d0e5 | BrCCOC1CCCCO1.Cc1cncc2cccc(N[C@@H]3CC[C@H](N)CC3)c12>>Cc1cncc2cccc(N[C@@H]3CC[C@H](NCCO)CC3)c12 | BrCCOC1OCCCC1.Cl.CC1=CN=CC2=CC=CC(=C12)N[C@@H]1CC[C@@H](CC1)N>>Cl.CC1=CN=CC2=CC=CC(=C12)N[C@@H]1CC[C@@H](CC1)NCCO | Br[CH2:17][CH2:18][O:19]C1CCCCO1.[CH3:1][c:2]1[cH:3][n:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([NH:11][C@H:12]3[CH2:13][CH2:14][C@@H:15]([NH2:16])[CH2:20][CH2:21]3)[c:22]12>>[CH3:1][c:2]1[cH:3][n:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([NH:11][C@H:12]3[CH2:13][CH2:14][C@@H:15]([NH:16][CH2:17][CH2:18][OH:19])[CH2:20][CH2:... | BrCCOC1CCCCO1.Cc1cncc2cccc(N[C@@H]3CC[C@H](N)CC3)c12 | Cc1cncc2cccc(N[C@@H]3CC[C@H](NCCO)CC3)c12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | ea5e2ef01067c3bff8f2185e9a1c85d176cf6a06653e5daa7dff2663a74ade66 | 9a9b1b205eb0298199862d313a9ef714203a0350cfdb128705dab974552275be | c1cc(NC2CCCCC2)c2ccncc2c1 | Br-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-C1-C-C-C-C-O-1.[C:4]-[C:5](-[NH2;D1;+0:6])-[C:7]>>[C:4]-[C:5](-[NH;D2;+0:6]-[CH2;D2;+0:1]-[C:2]-[OH;D1;+0:3])-[C:7] | null | [] | null | null | null | null | According to the method of Example 144, an alkylation reaction with 2-(2-bromoethoxy)tetrahydro-2H-pyran and a deprotection reaction were performed by using the compound of Example 120 to obtain the title compound.
Conditions: See reaction.notes.procedure_details.
Workup: a deprotection reaction | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Ether.Primary amine | Primary alcohol.Secondary amine | C1CCOCC1 | null | c1ccc2cnccc2c1.C1CCCCC1 | HBr | null | null | null | BrCCOC1CCCCO1.Cc1cncc2cccc(N[C@@H]3CC[C@H](N)CC3)c12>>Cc1cncc2cccc(N[C@@H]3CC[C@H](NCCO)CC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d229cb2de4d94ee3acd656b3de7ca16d | BrCCOC1CCCCO1.N#Cc1cncc2cccc(O[C@@H]3CC[C@@H](N)CC3)c12>>N#Cc1cncc2cccc(O[C@@H]3CC[C@@H](NCCO)CC3)c12 | BrCCOC1OCCCC1.Cl.C(#N)C1=CN=CC2=CC=CC(=C12)O[C@@H]1CC[C@H](CC1)N>>Cl.C(#N)C1=CN=CC2=CC=CC(=C12)O[C@@H]1CC[C@H](CC1)NCCO | Br[CH2:19][CH2:20][O:21]C1CCCCO1.[N:2]#[C:3][c:4]1[cH:5][n:6][cH:7][c:8]2[cH:9][cH:10][cH:11][c:12]([O:13][C@H:14]3[CH2:15][CH2:16][C@H:17]([NH2:18])[CH2:22][CH2:23]3)[c:24]12>>[N:2]#[C:3][c:4]1[cH:5][n:6][cH:7][c:8]2[cH:9][cH:10][cH:11][c:12]([O:13][C@H:14]3[CH2:15][CH2:16][C@H:17]([NH:18][CH2:19][CH2:20][OH:21])[CH2:... | BrCCOC1CCCCO1.N#Cc1cncc2cccc(O[C@@H]3CC[C@@H](N)CC3)c12 | N#Cc1cncc2cccc(O[C@@H]3CC[C@@H](NCCO)CC3)c12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | ea5e2ef01067c3bff8f2185e9a1c85d176cf6a06653e5daa7dff2663a74ade66 | 9a9b1b205eb0298199862d313a9ef714203a0350cfdb128705dab974552275be | c1cc(OC2CCCCC2)c2ccncc2c1 | Br-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-C1-C-C-C-C-O-1.[C:4]-[C:5](-[NH2;D1;+0:6])-[C:7]>>[C:4]-[C:5](-[NH;D2;+0:6]-[CH2;D2;+0:1]-[C:2]-[OH;D1;+0:3])-[C:7] | null | [] | null | null | null | null | According to the method of Example 144, an alkylation reaction with 2-(2-bromoethoxy)tetrahydro-2H-pyran and a deprotection reaction were performed by using the compound of Example 134 to obtain the title compound.
Conditions: See reaction.notes.procedure_details.
Workup: a deprotection reaction | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Ether.Primary amine | Primary alcohol.Secondary amine | C1CCOCC1 | null | c1ccc2cnccc2c1.C1CCCCC1 | HBr | null | null | null | BrCCOC1CCCCO1.N#Cc1cncc2cccc(O[C@@H]3CC[C@@H](N)CC3)c12>>N#Cc1cncc2cccc(O[C@@H]3CC[C@@H](NCCO)CC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-68a2a3cab0e14ea68b8e17f3298801c9 | O=[N+]([O-])c1cccc2c(O)ncc(Br)c12>>Nc1cccc2c(O)ncc(Br)c12 | O.O.[Sn](Cl)Cl.OC1=NC=C(C2=C(C=CC=C12)[N+](=O)[O-])Br>>OC1=NC=C(C2=C(C=CC=C12)N)Br | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]([OH:8])[n:9][cH:10][c:11]([Br:12])[c:13]12>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]([OH:8])[n:9][cH:10][c:11]([Br:12])[c:13]12 | O=[N+]([O-])c1cccc2c(O)ncc(Br)c12 | Nc1cccc2c(O)ncc(Br)c12 | null | null | null | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2cnccc2c1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | According to the method of Example 114, Step A, a reduction reaction with tin(II) chloride dihydrate was performed by using Intermediate 137 to obtain the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2cnccc2c1 | Other | null | null | null | O=[N+]([O-])c1cccc2c(O)ncc(Br)c12>>Nc1cccc2c(O)ncc(Br)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6c378cc1f8624b089d5efbafe5b55132 | Nc1cccc2c(O)ncc(Br)c12.[CH3][Sn]([CH3])([CH3])[CH3]>>Cc1cnc(O)c2cccc(N)c12 | C[Sn](C)(C)C.OC1=NC=C(C2=C(C=CC=C12)N)Br>>OC1=NC=C(C2=C(C=CC=C12)N)C | Br[c:2]1[cH:3][n:4][c:5]([OH:6])[c:7]2[cH:8][cH:9][cH:10][c:11]([NH2:12])[c:13]12.[CH3][Sn]([CH3])([CH3])[CH3:1]>>[CH3:1][c:2]1[cH:3][n:4][c:5]([OH:6])[c:7]2[cH:8][cH:9][cH:10][c:11]([NH2:12])[c:13]12 | Nc1cccc2c(O)ncc(Br)c12.[CH3][Sn]([CH3])([CH3])[CH3] | Cc1cnc(O)c2cccc(N)c12 | null | null | null | C-C Coupling | Stille reaction_other | 9226641c9ff2be6bc2e9fd20e6ce2e5c77a36942dcf6365e045325bcb58f0f54 | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | c1ccc2cnccc2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1:[c:7].[CH3;D1;+0:8]-[Sn](-[CH3])(-[CH3])-[CH3]>>[CH3;D1;+0:8]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1:[c:7] | null | [] | null | null | null | null | According to the method of Example 106, Step A, a methylation reaction with tetramethyltin was performed by using Intermediate 138 to obtain the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | HBr.Sn | null | null | null | Nc1cccc2c(O)ncc(Br)c12.[CH3][Sn]([CH3])([CH3])[CH3]>>Cc1cnc(O)c2cccc(N)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5c825aac16db4c78bc62bbf1ee6b3093 | Cc1cnc(O)c2cccc(N[C@@H]3CC[C@@H](NC(=O)OC(C)(C)C)CC3)c12>>Cc1cnc(O)c2cccc(N[C@@H]3CC[C@@H](N)CC3)c12 | Cl.OC1=NC=C(C2=C(C=CC=C12)N[C@@H]1CC[C@H](CC1)NC(=O)OC(C)(C)C)C>>Cl.OC1=NC=C(C2=C(C=CC=C12)N[C@@H]1CC[C@H](CC1)N)C | CC(C)(C)OC(=O)[NH:17][C@H:16]1[CH2:15][CH2:14][C@H:13]([NH:12][c:11]2[cH:10][cH:9][cH:8][c:7]3[c:5]([OH:6])[n:4][cH:3][c:2]([CH3:1])[c:20]32)[CH2:19][CH2:18]1>>[CH3:1][c:2]1[cH:3][n:4][c:5]([OH:6])[c:7]2[cH:8][cH:9][cH:10][c:11]([NH:12][C@H:13]3[CH2:14][CH2:15][C@H:16]([NH2:17])[CH2:18][CH2:19]3)[c:20]12 | Cc1cnc(O)c2cccc(N[C@@H]3CC[C@@H](NC(=O)OC(C)(C)C)CC3)c12 | Cc1cnc(O)c2cccc(N[C@@H]3CC[C@@H](N)CC3)c12 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1cc(NC2CCCCC2)c2ccncc2c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4] | null | [] | null | null | null | null | According to the method of Step A of this example, deprotection with concentrated hydrochloric acid was performed by using Intermediate 140 to obtain the title compound.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2cnccc2c1.C1CCCCC1 | HO- | null | null | null | Cc1cnc(O)c2cccc(N[C@@H]3CC[C@@H](NC(=O)OC(C)(C)C)CC3)c12>>Cc1cnc(O)c2cccc(N[C@@H]3CC[C@@H](N)CC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ff7dca7ab98c4b5d90e0151012ef0475 | Brc1cncc2ccccc12>>O=[N+]([O-])c1cccc2cncc(Br)c12 | CCCCCC.BrC1=CN=CC2=CC=CC=C12.N.[N+](=O)([O-])[O-].[K+].BrC1=CN=CC2=CC=CC=C12>>BrC1=CN=CC2=CC=CC(=C12)[N+](=O)[O-] | [cH:4]1[cH:5][cH:6][cH:7][c:8]2[cH:9][n:10][cH:11][c:12]([Br:13])[c:14]12>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8]2[cH:9][n:10][cH:11][c:12]([Br:13])[c:14]12 | Brc1cncc2ccccc12 | O=[N+]([O-])c1cccc2cncc(Br)c12 | null | null | C(C)(=O)OCC.S(O)(O)(=O)=O | Functional Group Addition | OtherReaction | af041d80e34a3ce46b5eb910f230615587e5ab9eb4305ac845f1ae2dbd577a25 | 22f3183026a2d99c91ec0c53f0059a15c8421016bd62c8ab45281362b96dc686 | c1ccc2cnccc2c1 | [c:1]:[c:2]:[cH;D2;+0:3]:[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1>>[O;-;D1;H0:10]-[#7;+:11](=[O;D1;H0:12])-[c;H0;D3;+0:3](:[c:2]:[c:1]):[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1 | 48.5 | [{"value": 48.5, "product": "BrC1=CN=CC2=CC=CC(=C12)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | With vigorous stirring, concentrated sulfuric acid (36 ml) was added with 4-bromoisoquinoline (10.0 g, Tokyo Kasei Kogyo) to such an extent that the temperature should not exceed 10° C. and stirred for a while to attain complete dissolution. Potassium nitrate (4.9 g, Kanto Chemicals) was dissolved in concentrated sulfu... | 10.6084/m9.figshare.5104873.v1 | null | null | Nitro group | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | Other | C(C)(=O)OCC.S(O)(O)(=O)=O | null | null | Brc1cncc2ccccc12>C(C)(=O)OCC.S(O)(O)(=O)=O>O=[N+]([O-])c1cccc2cncc(Br)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-00b5bb361fab4493b7f9bbbc53902e9e | O=[N+]([O-])c1cccc2cncc(Br)c12>>Nc1cccc2cncc(Br)c12 | [OH-].[Na+].BrC1=CN=CC2=CC=CC(=C12)[N+](=O)[O-].Cl>>BrC1=CN=CC2=CC=CC(=C12)N | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][cH:5][c:6]2[cH:7][n:8][cH:9][c:10]([Br:11])[c:12]12>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[cH:7][n:8][cH:9][c:10]([Br:11])[c:12]12 | O=[N+]([O-])c1cccc2cncc(Br)c12 | Nc1cccc2cncc(Br)c12 | null | null | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2cnccc2c1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 55.9 | [{"value": 55.9, "product": "BrC1=CN=CC2=CC=CC(=C12)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 12 | HOUR | 4-Bromo-5-nitroisoquinoline (1.0 g) synthesized as described above and stannous chloride dihydrate (4.5 g, Wako Pure Chemical Industries) were suspended in ethanol (30 ml), added with concentrated hydrochloric acid (2.3 ml) and stirred at 80° C. for 30 minutes and at room temperature for further 12 hours. The reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2cnccc2c1 | Other | C(C)O | 80 | 12 | O=[N+]([O-])c1cccc2cncc(Br)c12>C(C)O>Nc1cccc2cncc(Br)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-09dfd65f903d4a53aba13fa33f376eb8 | NCCCN.O=S(=O)(Cl)c1cccc2cnccc12>>NCCCNS(=O)(=O)c1cccc2cnccc12 | Cl.C1=NC=CC=2C(=CC=CC12)S(=O)(=O)Cl.C(CCN)N>>C1=NC=CC2=C(C=CC=C12)S(=O)(=O)NCCCN | [NH2:1][CH2:2][CH2:3][CH2:4][NH2:5].Cl[S:6](=[O:7])(=[O:8])[c:9]1[cH:10][cH:11][cH:12][c:13]2[cH:14][n:15][cH:16][cH:17][c:18]12>>[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][S:6](=[O:7])(=[O:8])[c:9]1[cH:10][cH:11][cH:12][c:13]2[cH:14][n:15][cH:16][cH:17][c:18]12 | NCCCN.O=S(=O)(Cl)c1cccc2cnccc12 | NCCCNS(=O)(=O)c1cccc2cnccc12 | null | null | null | Miscellaneous | Sulfonamide synthesis (Schotten-Baumann) primary amine | a86b0632821e188c0a5dc5a5a2aac298ab3eccaee8a52ba46078c3d5975a290d | 50f8fbf3d327483c3eeff8f6cbd4065e4c7600bb501fbe08958a5c79a0926428 | c1ccc2cnccc2c1 | 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: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] | 81.1 | [{"value": 81.1, "product": "C1=NC=CC2=C(C=CC=C12)S(=O)(=O)NCCCN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | According to the method of Reference Example 2, a reaction was performed by using isoquinoline-5-sulfonyl chloride hydrochloride (20 g) and 1,3-propylenediamine (22.2 g) to obtain the title compound (16.3 g).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccc2cnccc2c1 | HCl | null | null | null | NCCCN.O=S(=O)(Cl)c1cccc2cnccc12>>NCCCNS(=O)(=O)c1cccc2cnccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ff4b8c61b8b94d78ab0ae7c76692603a | NCCCCN.O=S(=O)(Cl)c1cccc2cnccc12>>NCCCCNS(=O)(=O)c1cccc2cnccc12 | Cl.C1=NC=CC=2C(=CC=CC12)S(=O)(=O)Cl.C(CCCN)N>>C1=NC=CC2=C(C=CC=C12)S(=O)(=O)NCCCCN | [NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][NH2:6].Cl[S:7](=[O:8])(=[O:9])[c:10]1[cH:11][cH:12][cH:13][c:14]2[cH:15][n:16][cH:17][cH:18][c:19]12>>[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][S:7](=[O:8])(=[O:9])[c:10]1[cH:11][cH:12][cH:13][c:14]2[cH:15][n:16][cH:17][cH:18][c:19]12 | NCCCCN.O=S(=O)(Cl)c1cccc2cnccc12 | NCCCCNS(=O)(=O)c1cccc2cnccc12 | null | null | null | Miscellaneous | Sulfonamide synthesis (Schotten-Baumann) primary amine | a86b0632821e188c0a5dc5a5a2aac298ab3eccaee8a52ba46078c3d5975a290d | 50f8fbf3d327483c3eeff8f6cbd4065e4c7600bb501fbe08958a5c79a0926428 | c1ccc2cnccc2c1 | 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: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] | 61.9 | [{"value": 61.9, "product": "C1=NC=CC2=C(C=CC=C12)S(=O)(=O)NCCCCN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | According to the method of Reference Example 2, a reaction was performed by using isoquinoline-5-sulfonyl chloride hydrochloride (18.8 g) and 1,4-butylenediamine (25 g) to obtain the title compound (12.3 g).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccc2cnccc2c1 | HCl | null | null | null | NCCCCN.O=S(=O)(Cl)c1cccc2cnccc12>>NCCCCNS(=O)(=O)c1cccc2cnccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3eab5bbdfa2e416eae1d6d8b01877451 | CC(C)(C)OC(=O)NC1CCCC(NS(=O)(=O)c2cccc3cnccc23)C1>>NC1CCCC(NS(=O)(=O)c2cccc3cnccc23)C1 | C(C)(C)(C)OC(=O)NC1CC(CCC1)NS(=O)(=O)C1=C2C=CN=CC2=CC=C1.Cl>>C1=NC=CC2=C(C=CC=C12)S(=O)(=O)NC1CC(CCC1)N | CC(C)(C)OC(=O)[NH:1][CH:2]1[CH2:3][CH2:4][CH2:5][CH:6]([NH:7][S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:13][cH:14][c:15]3[cH:16][n:17][cH:18][cH:19][c:20]23)[CH2:21]1>>[NH2:1][CH:2]1[CH2:3][CH2:4][CH2:5][CH:6]([NH:7][S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:13][cH:14][c:15]3[cH:16][n:17][cH:18][cH:19][c:20]23)[CH2:21]1 | CC(C)(C)OC(=O)NC1CCCC(NS(=O)(=O)c2cccc3cnccc23)C1 | NC1CCCC(NS(=O)(=O)c2cccc3cnccc23)C1 | null | null | CO | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=S(=O)(NC1CCCCC1)c1cccc2cnccc12 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4] | 108.4 | [{"value": 108.4, "product": "C1=NC=CC2=C(C=CC=C12)S(=O)(=O)NC1CC(CCC1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Intermediate 54 (6 g) obtained above was added to a 10% hydrogen chloride solution in methanol (50 ml) and stirred under reflux by heating for 1.5 hours. The solvent was evaporated under reduced pressure, and the residue was dissolved in a mixed solvent of dichloromethane and ethanol, added with saturated aqueous potas... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | C1CCCCC1.c1ccc2cnccc2c1 | HO- | CO | null | null | CC(C)(C)OC(=O)NC1CCCC(NS(=O)(=O)c2cccc3cnccc23)C1>CO>NC1CCCC(NS(=O)(=O)c2cccc3cnccc23)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-39fe4c2e1195477eb249df5a4f124b5a | CC(C)(CN)CNC(=O)OC(C)(C)C.O=S(=O)(Cl)c1cccc2cnccc12>>CC(C)(CNC(=O)OC(C)(C)C)CNS(=O)(=O)c1cccc2cnccc12 | Cl.C1=NC=CC=2C(=CC=CC12)S(=O)(=O)Cl.C(C)(C)(C)OC(=O)NCC(CN)(C)C>>C(C)(C)(C)OC(=O)NCC(CNS(=O)(=O)C1=C2C=CN=CC2=CC=C1)(C)C | [CH3:1][C:2]([CH3:3])([CH2:4][NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[CH2:13][NH2:14].Cl[S:15](=[O:16])(=[O:17])[c:18]1[cH:19][cH:20][cH:21][c:22]2[cH:23][n:24][cH:25][cH:26][c:27]12>>[CH3:1][C:2]([CH3:3])([CH2:4][NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[CH2:13][NH:14][S:15](=[O:16])(... | CC(C)(CN)CNC(=O)OC(C)(C)C.O=S(=O)(Cl)c1cccc2cnccc12 | CC(C)(CNC(=O)OC(C)(C)C)CNS(=O)(=O)c1cccc2cnccc12 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | c1ccc2cnccc2c1 | 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: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] | 97.8 | [{"value": 97.8, "product": "C(C)(C)(C)OC(=O)NCC(CNS(=O)(=O)C1=C2C=CN=CC2=CC=C1)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | According to Reference Example 5, Step B, a reaction was performed by using isoquinoline-5-sulfonyl chloride hydrochloride (7.8 g) and Intermediate 56 (5.97 g) to obtain the title compound (11.36 g).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccc2cnccc2c1 | HCl | null | null | null | CC(C)(CN)CNC(=O)OC(C)(C)C.O=S(=O)(Cl)c1cccc2cnccc12>>CC(C)(CNC(=O)OC(C)(C)C)CNS(=O)(=O)c1cccc2cnccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9bdeb39ac076409d9aa1b08b86692b72 | CC(C)(CNC(=O)OC(C)(C)C)CNS(=O)(=O)c1cccc2cnccc12>>CC(C)(CN)CNS(=O)(=O)c1cccc2cnccc12 | C(C)(C)(C)OC(=O)NCC(CNS(=O)(=O)C1=C2C=CN=CC2=CC=C1)(C)C.Cl>>C1=NC=CC2=C(C=CC=C12)S(=O)(=O)NCC(CN)(C)C | CC(C)(C)OC(=O)[NH:5][CH2:4][C:2]([CH3:1])([CH3:3])[CH2:6][NH:7][S:8](=[O:9])(=[O:10])[c:11]1[cH:12][cH:13][cH:14][c:15]2[cH:16][n:17][cH:18][cH:19][c:20]12>>[CH3:1][C:2]([CH3:3])([CH2:4][NH2:5])[CH2:6][NH:7][S:8](=[O:9])(=[O:10])[c:11]1[cH:12][cH:13][cH:14][c:15]2[cH:16][n:17][cH:18][cH:19][c:20]12 | CC(C)(CNC(=O)OC(C)(C)C)CNS(=O)(=O)c1cccc2cnccc12 | CC(C)(CN)CNS(=O)(=O)c1cccc2cnccc12 | null | null | CO | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc2cnccc2c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | 92.4 | [{"value": 92.4, "product": "C1=NC=CC2=C(C=CC=C12)S(=O)(=O)NCC(CN)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | According to Reference Example 5, Step C, a reaction was performed by using Intermediate 57 (11 g) and 10% hydrogen chloride in methanol (80 ml) to obtain the title compound (7.58 g).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2cnccc2c1 | HO- | CO | null | null | CC(C)(CNC(=O)OC(C)(C)C)CNS(=O)(=O)c1cccc2cnccc12>CO>CC(C)(CN)CNS(=O)(=O)c1cccc2cnccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cc24d669fdfd47959b83d7a2b71561b6 | CC(C)(C)OC(=O)NCc1ccc(CN)cc1.O=S(=O)(Cl)c1cccc2cnccc12>>CC(C)(C)OC(=O)NCc1ccc(CNS(=O)(=O)c2cccc3cnccc23)cc1 | Cl.C1=NC=CC=2C(=CC=CC12)S(=O)(=O)Cl.C(C)(C)(C)OC(=O)NCC1=CC=C(CN)C=C1>>C(C)(C)(C)OC(=O)NCC1=CC=C(C=C1)CNS(=O)(=O)C1=C2C=CN=CC2=CC=C1 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][c:10]1[cH:11][cH:12][c:13]([CH2:14][NH2:15])[cH:29][cH:30]1.Cl[S:16](=[O:17])(=[O:18])[c:19]1[cH:20][cH:21][cH:22][c:23]2[cH:24][n:25][cH:26][cH:27][c:28]12>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][c:10]1[cH:11][cH:12][c:13]([CH2:14][NH... | CC(C)(C)OC(=O)NCc1ccc(CN)cc1.O=S(=O)(Cl)c1cccc2cnccc12 | CC(C)(C)OC(=O)NCc1ccc(CNS(=O)(=O)c2cccc3cnccc23)cc1 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=S(=O)(NCc1ccccc1)c1cccc2cnccc12 | 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]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:7]-[C:8]-[c:9])-[c:4](:[c:5]):[c:6] | 82.7 | [{"value": 82.7, "product": "C(C)(C)(C)OC(=O)NCC1=CC=C(C=C1)CNS(=O)(=O)C1=C2C=CN=CC2=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | According to Reference Example 5, Step B, a reaction was performed by using isoquinoline-5-sulfonyl chloride hydrochloride (10 g) and Intermediate 59 (8.96 g) to obtain the title compound (13.39 g).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccc2cnccc2c1 | HCl | null | null | null | CC(C)(C)OC(=O)NCc1ccc(CN)cc1.O=S(=O)(Cl)c1cccc2cnccc12>>CC(C)(C)OC(=O)NCc1ccc(CNS(=O)(=O)c2cccc3cnccc23)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-91463f1115d148529346c0f15f210d9b | CC(C)(C)OC(=O)NCc1ccc(CNS(=O)(=O)c2cccc3cnccc23)cc1>>NCc1ccc(CNS(=O)(=O)c2cccc3cnccc23)cc1 | C(C)(C)(C)OC(=O)NCC1=CC=C(C=C1)CNS(=O)(=O)C1=C2C=CN=CC2=CC=C1.Cl>>C1=NC=CC2=C(C=CC=C12)S(=O)(=O)NCC1=CC=C(C=C1)CN | CC(C)(C)OC(=O)[NH:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][NH:8][S:9](=[O:10])(=[O:11])[c:12]2[cH:13][cH:14][cH:15][c:16]3[cH:17][n:18][cH:19][cH:20][c:21]23)[cH:22][cH:23]1>>[NH2:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][NH:8][S:9](=[O:10])(=[O:11])[c:12]2[cH:13][cH:14][cH:15][c:16]3[cH:17][n:18][cH:19][cH:20][c:21]23)... | CC(C)(C)OC(=O)NCc1ccc(CNS(=O)(=O)c2cccc3cnccc23)cc1 | NCc1ccc(CNS(=O)(=O)c2cccc3cnccc23)cc1 | null | null | CO | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=S(=O)(NCc1ccccc1)c1cccc2cnccc12 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[c:3]>>[NH2;D1;+0:1]-[C:2]-[c:3] | 80.5 | [{"value": 80.5, "product": "C1=NC=CC2=C(C=CC=C12)S(=O)(=O)NCC1=CC=C(C=C1)CN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | According to Reference Example 5, Step C, a reaction was performed by using Intermediate 60 (6 g) and 10% hydrogen chloride in methanol (20 ml) to obtain the title compound (3.7 g).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ccc2cnccc2c1 | HO- | CO | null | null | CC(C)(C)OC(=O)NCc1ccc(CNS(=O)(=O)c2cccc3cnccc23)cc1>CO>NCc1ccc(CNS(=O)(=O)c2cccc3cnccc23)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5c0b777ddedc4173bf1e910f3e6f9fd8 | CC(C)(C)OC(=O)NCc1cccc(CN)c1.O=S(=O)(Cl)c1cccc2cnccc12>>CC(C)(C)OC(=O)NCc1cccc(CNS(=O)(=O)c2cccc3cnccc23)c1 | Cl.C1=NC=CC=2C(=CC=CC12)S(=O)(=O)Cl.C(C)(C)(C)OC(=O)NCC=1C=C(CN)C=CC1>>C(C)(C)(C)OC(=O)NCC1=CC(=CC=C1)CNS(=O)(=O)C1=C2C=CN=CC2=CC=C1 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]([CH2:15][NH2:16])[cH:30]1.Cl[S:17](=[O:18])(=[O:19])[c:20]1[cH:21][cH:22][cH:23][c:24]2[cH:25][n:26][cH:27][cH:28][c:29]12>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]([CH2... | CC(C)(C)OC(=O)NCc1cccc(CN)c1.O=S(=O)(Cl)c1cccc2cnccc12 | CC(C)(C)OC(=O)NCc1cccc(CNS(=O)(=O)c2cccc3cnccc23)c1 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=S(=O)(NCc1ccccc1)c1cccc2cnccc12 | 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]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:7]-[C:8]-[c:9])-[c:4](:[c:5]):[c:6] | 78.1 | [{"value": 78.1, "product": "C(C)(C)(C)OC(=O)NCC1=CC(=CC=C1)CNS(=O)(=O)C1=C2C=CN=CC2=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | According to Reference Example 5, Step B, a reaction was performed by using isoquinoline-5-sulfonyl chloride hydrochloride (9 g) and Intermediate 62 (8 g) to obtain the title compound (11.3 g).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccc2cnccc2c1 | HCl | null | null | null | CC(C)(C)OC(=O)NCc1cccc(CN)c1.O=S(=O)(Cl)c1cccc2cnccc12>>CC(C)(C)OC(=O)NCc1cccc(CNS(=O)(=O)c2cccc3cnccc23)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-45adba3b20e14f428e038d8658406cee | CC(C)(C)OC(=O)NCc1cccc(CNS(=O)(=O)c2cccc3cnccc23)c1>>NCc1cccc(CNS(=O)(=O)c2cccc3cnccc23)c1 | C(C)(C)(C)OC(=O)NCC1=CC(=CC=C1)CNS(=O)(=O)C1=C2C=CN=CC2=CC=C1.Cl>>C1=NC=CC2=C(C=CC=C12)S(=O)(=O)NCC1=CC(=CC=C1)CN | CC(C)(C)OC(=O)[NH:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][NH:9][S:10](=[O:11])(=[O:12])[c:13]2[cH:14][cH:15][cH:16][c:17]3[cH:18][n:19][cH:20][cH:21][c:22]23)[cH:23]1>>[NH2:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:8][NH:9][S:10](=[O:11])(=[O:12])[c:13]2[cH:14][cH:15][cH:16][c:17]3[cH:18][n:19][cH:20][cH:21][c... | CC(C)(C)OC(=O)NCc1cccc(CNS(=O)(=O)c2cccc3cnccc23)c1 | NCc1cccc(CNS(=O)(=O)c2cccc3cnccc23)c1 | null | null | CO | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=S(=O)(NCc1ccccc1)c1cccc2cnccc12 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[c:3]>>[NH2;D1;+0:1]-[C:2]-[c:3] | 81 | [{"value": 81.0, "product": "C1=NC=CC2=C(C=CC=C12)S(=O)(=O)NCC1=CC(=CC=C1)CN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | According to Reference Example 5, Step C, a reaction was performed by using Intermediate 63 (5 g) and 10% hydrogen chloride in methanol (20 ml) to obtain the title compound (3.1 g).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ccc2cnccc2c1 | HO- | CO | null | null | CC(C)(C)OC(=O)NCc1cccc(CNS(=O)(=O)c2cccc3cnccc23)c1>CO>NCc1cccc(CNS(=O)(=O)c2cccc3cnccc23)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9a2925c670fe42288d32beb72b10d9f5 | C=O.O=C1C=CC(=O)N1>>O=C1C=C(CO)C(=O)N1 | C1(C=CC(N1)=O)=O.C=O.[OH-].[Na+]>>OCC=1C(=O)NC(C1)=O | [CH2:5]=[O:6].[O:1]=[C:2]1[CH:3]=[CH:4][C:7](=[O:8])[NH:9]1>>[O:1]=[C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[C:7](=[O:8])[NH:9]1 | C=O.O=C1C=CC(=O)N1 | O=C1C=C(CO)C(=O)N1 | null | null | null | C-C Coupling | OtherReaction | 17a8683b74042d2cc6981b4023bdc52e578574819630a5c7a7864de64f51c3f1 | 4396295d899f5d4f5de2e844a80fc7d194b4da158f49df3d2717206b401b59bd | O=C1C=CC(=O)N1 | [CH2;D1;+0:1]=[O;H0;D1;+0:2].[O;D1;H0:3]=[C:4]1-[#7:5]-[C:6](=[O;D1;H0:7])-[CH;D2;+0:8]=[C:9]-1>>[O;D1;H0:3]=[C:4]1-[#7:5]-[C:6](=[O;D1;H0:7])-[C;H0;D3;+0:8](-[CH2;D2;+0:1]-[OH;D1;+0:2])=[C:9]-1 | null | [] | null | null | null | null | 24 Parts of maleimide (manufactured by Aldrich Corporation), 21 parts of 35% HCOH (manufactured by Wako Pure Chemical Industries, Ltd.) and 0.7 parts of a 5% aqueous NaOH solution are placed in a reactor and reacted at 40° C. for 2 hours. As a result, a white crystal of hydroxymethylmaleimide precipitates. This white c... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde | Primary alcohol | C1=CCNC1 | C1=CCNC1 | C1=CCNC1 | null | null | null | null | C=O.O=C1C=CC(=O)N1>>O=C1C=C(CO)C(=O)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-62574a4f57594484b87becc8b7f760e8 | CCCCCC(O)Br.O=S(=O)([O-])c1ccc(O)cc1>>O=S(=O)([O-])c1ccc(OCCCCCCO)cc1 | [Na+].OC1=CC=C(C=C1)S(=O)(=O)[O-].[OH-].[K+].BrC(CCCCC)O>>OCCCCCCOC1=CC=C(C=C1)S(=O)(=O)[O-].[Na+] | Br[CH:10]([CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[OH:16].[O:1]=[S:2](=[O:3])([O-:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:17][cH:18]1>>[O:1]=[S:2](=[O:3])([O-:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16])[cH:17][cH:18]1 | CCCCCC(O)Br.O=S(=O)([O-])c1ccc(O)cc1 | O=S(=O)([O-])c1ccc(OCCCCCCO)cc1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 2a9380ebb68334989924756cf01b7949046a4f7a65a764f1d76e39ed500565f9 | 2786f500c47f12973cdffc6c715f1d0ddaf160e62af6ac2ce87986b5e7d6597e | c1ccccc1 | Br-[CH;D3;+0:1](-[OH;D1;+0:2])-[C:3]-[C:4]-[C:5]-[C:6]-[CH3;D1;+0:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[OH;D1;+0:2]-[CH2;D2;+0:7]-[C:6]-[C:5]-[C:4]-[C:3]-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11] | 98.8 | [{"value": 92.0, "product": "OCCCCCCOC1=CC=C(C=C1)S(=O)(=O)[O-].[Na+]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.8, "product": "OCCCCCCOC1=CC=C(C=C1)S(=O)(=O)[O-].[Na+]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Into a three-necked round-bottom flask equipped with a magnetic stirring bar and a reflux condenser were added 4-hydroxybenzenesulfonicacid sodium salt (30.0 grams (g), 0.13 mol), potassium hydroxide (9.0 g, 0.16 mol) and distilled water (60 milliliter (ml)). 1-Bromohexanol (23.16 g, 0.13 mol) dissolved in ethanol (50 ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary alcohol.Aromatic alcohol | Ether.Primary alcohol | null | null | c1ccccc1 | HBr | C(C)O | null | null | CCCCCC(O)Br.O=S(=O)([O-])c1ccc(O)cc1>C(C)O>O=S(=O)([O-])c1ccc(OCCCCCCO)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-327e3218e975482ebbe892dcbab483af | CC(C)(C)c1ccc(O)c(C(C)(C)C)c1.CC(C)c1cccc(C(C)C)c1N>>CC(C)c1cccc(C(C)C)c1N=Nc1cc(C(C)(C)C)cc(C(C)(C)C)c1O | C(C)(C)C1=C(N)C(=CC=C1)C(C)C.N1=CC=CC=C1.C(C)(C)(C)C1=C(C=CC(=C1)C(C)(C)C)O.[OH-].[Na+].C1(=CC=CC=C1)[O-]>>C(C)(C)C1=C(C(=CC=C1)C(C)C)N=NC1=C(C(=CC(=C1)C(C)(C)C)C(C)(C)C)O | [cH:15]1[cH:16][c:17]([C:18]([CH3:19])([CH3:20])[CH3:21])[cH:22][c:23]([C:24]([CH3:25])([CH3:26])[CH3:27])[c:28]1[OH:29].[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([CH:9]([CH3:10])[CH3:11])[c:12]1[NH2:13]>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([CH:9]([CH3:10])[CH3:11])[c:12]1[N:13]=[N:14][c:15]1[... | CC(C)(C)c1ccc(O)c(C(C)(C)C)c1.CC(C)c1cccc(C(C)C)c1N | CC(C)c1cccc(C(C)C)c1N=Nc1cc(C(C)(C)C)cc(C(C)(C)C)c1O | null | null | O.C1(=CC=CC=C1)C | Functional Group Addition | OtherReaction | 4dfa1e0075917e3f76a2c771d85af2eb7328e8c1dacc2fef053ab9d7871727bb | 369e32a405523c63be3b198dc14b1fa8567bb17806d598f8dc85ecca177f9307 | c1ccc(N=Nc2ccccc2)cc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H1:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10]>>[O;D1;H1:5]-[c:6](:[c:7]):[c;H0;D3;+0:8](-[#7:11]=[N;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:9]:[c:10] | null | [] | null | null | null | null | This phenol was prepared, as described for above, from a theoretical yield of 7.4 mmol of diazotized 2,6-diisopropylaniline and a phenolate solution comprised of 2,4-Ditertbutylphenol (1.42 g), water (15 mL), NaOH (0.5 g), pyridine (3 mL), and toluene (6 mL) Yield=0.98 g (36%).
Conditions: See reaction.notes.procedure_... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Diazene | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Other | O.C1(=CC=CC=C1)C | null | null | CC(C)(C)c1ccc(O)c(C(C)(C)C)c1.CC(C)c1cccc(C(C)C)c1N>O.C1(=CC=CC=C1)C>CC(C)c1cccc(C(C)C)c1N=Nc1cc(C(C)(C)C)cc(C(C)(C)C)c1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-966493f923fe4472bb4fc0c0429b9e71 | CC(C)c1cccc(C(C)C)c1N.Cc1ccc(O)c(-c2c3ccccc3cc3ccccc23)c1>>Cc1cc(N=Nc2c(C(C)C)cccc2C(C)C)c(O)c(-c2c3ccccc3cc3ccccc23)c1 | C(C)(C)C1=C(N)C(=CC=C1)C(C)C.N1=CC=CC=C1.C1=CC=CC2=CC3=CC=CC=C3C(=C12)C1=C(C=CC(=C1)C)O.[OH-].[Na+].C1(=CC=CC=C1)[O-]>>C(C)(C)C1=C(C(=CC=C1)C(C)C)N=NC1=C(C(=CC(=C1)C)C=1C2=CC=CC=C2C=C2C=CC=CC12)O | [NH2:6][c:7]1[c:8]([CH:9]([CH3:10])[CH3:11])[cH:12][cH:13][cH:14][c:15]1[CH:16]([CH3:17])[CH3:18].[CH3:1][c:2]1[cH:3][cH:4][c:19]([OH:20])[c:21](-[c:22]2[c:23]3[cH:24][cH:25][cH:26][cH:27][c:28]3[cH:29][c:30]3[cH:31][cH:32][cH:33][cH:34][c:35]23)[cH:36]1>>[CH3:1][c:2]1[cH:3][c:4]([N:5]=[N:6][c:7]2[c:8]([CH:9]([CH3:10])... | CC(C)c1cccc(C(C)C)c1N.Cc1ccc(O)c(-c2c3ccccc3cc3ccccc23)c1 | Cc1cc(N=Nc2c(C(C)C)cccc2C(C)C)c(O)c(-c2c3ccccc3cc3ccccc23)c1 | null | null | O.C1=CC=CC=C1 | Functional Group Addition | OtherReaction | 4dfa1e0075917e3f76a2c771d85af2eb7328e8c1dacc2fef053ab9d7871727bb | 369e32a405523c63be3b198dc14b1fa8567bb17806d598f8dc85ecca177f9307 | c1ccc(N=Nc2cccc(-c3c4ccccc4cc4ccccc34)c2)cc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H1:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10]>>[O;D1;H1:5]-[c:6](:[c:7]):[c;H0;D3;+0:8](-[#7:11]=[N;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:9]:[c:10] | null | [] | null | null | null | null | This phenol was prepared, as described above, from a theoretical yield of 3.9 mmol of diazotized 2,6-diisopropylaniline and a phenolate solution comprised of 2-(9-Anthracenyl)-4-methylphenol (0.63 g), water (20 mL), NaOH (20 mmol), pyridine (2 mL), and benzene (4 mL). In this case, the product was eluted with ether:hex... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Diazene | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2cc3ccccc3cc2c1 | Other | O.C1=CC=CC=C1 | null | null | CC(C)c1cccc(C(C)C)c1N.Cc1ccc(O)c(-c2c3ccccc3cc3ccccc23)c1>O.C1=CC=CC=C1>Cc1cc(N=Nc2c(C(C)C)cccc2C(C)C)c(O)c(-c2c3ccccc3cc3ccccc23)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-45f72defb4ae417cbbd01a6cb99366f1 | COc1cscc1OC.C[C@H](O)CO>>CC1COc2cscc2O1 | COC1=CSC=C1OC.C([C@H](C)O)O.C(C)(=O)OCC>>CC1COC=2C(O1)=CSC2 | CO[c:5]1[cH:6][s:7][cH:8][c:9]1OC.[CH3:1][C@@H:2]([CH2:3][OH:4])[OH:10]>>[CH3:1][CH:2]1[CH2:3][O:4][c:5]2[cH:6][s:7][cH:8][c:9]2[O:10]1 | COc1cscc1OC.C[C@H](O)CO | CC1COc2cscc2O1 | null | O.C1(=CC=C(C=C1)S(=O)(=O)O)C | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 27a88f912a54d2a9c5080f339a9b1dc6565f1d8c89ad4e25d07c18a8cc4561ec | d3cf88dd21c2b1133a535341fad8736ebfcb343cc20bb0a78301ecc79ada442a | c1scc2c1OCCO2 | C-O-[c;H0;D3;+0:1]1:[c:2]:[#16;a:3]:[c:4]:[c;H0;D3;+0:5]:1-O-C.[C;D1;H3:6]-[C@H;D3;+0:7](-[OH;D1;+0:8])-[C:9]-[OH;D1;+0:10]>>[C;D1;H3:6]-[CH;D3;+0:7]1-[C:9]-[O;H0;D2;+0:10]-[c;H0;D3;+0:1]2:[c:2]:[#16;a:3]:[c:4]:[c;H0;D3;+0:5]:2-[O;H0;D2;+0:8]-1 | 69.5 | [{"value": 69.5, "product": "CC1COC=2C(O1)=CSC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3,4-dimethoxythiophene (5.18 g), (S)-1,2-propanediol (3.0 g) and p-toluenesulfonic acid monohydrate (100 mg) in toluene (50 ml) was heated at 95° C. during which a continuous stream of nitrogen was passed over the solution. After 30 h the reaction mixture was poured into ethyl acetate, washed with NaHCO3 ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Primary alcohol.Secondary alcohol | Ether.Ether | c1ccsc1 | c1scc2c1OCCO2 | c1scc2c1OCCO2 | HO- | O.C1(=CC=C(C=C1)S(=O)(=O)O)C.C1(=CC=CC=C1)C | null | null | COc1cscc1OC.C[C@H](O)CO>O.C1(=CC=C(C=C1)S(=O)(=O)O)C.C1(=CC=CC=C1)C>CC1COc2cscc2O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-893c7cabb2234d5d8d2cba94eaa12eb3 | CC(O)CO.COc1cscc1OC>>CC1COc2cscc2O1 | COC1=CSC=C1OC.C(C(C)O)O>>CC1COC=2C(O1)=CSC2 | [CH3:1][CH:2]([CH2:3][OH:4])[OH:10].CO[c:5]1[cH:6][s:7][cH:8][c:9]1OC>>[CH3:1][CH:2]1[CH2:3][O:4][c:5]2[cH:6][s:7][cH:8][c:9]2[O:10]1 | CC(O)CO.COc1cscc1OC | CC1COc2cscc2O1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 27a88f912a54d2a9c5080f339a9b1dc6565f1d8c89ad4e25d07c18a8cc4561ec | d3cf88dd21c2b1133a535341fad8736ebfcb343cc20bb0a78301ecc79ada442a | c1scc2c1OCCO2 | C-O-[c;H0;D3;+0:1]1:[c:2]:[#16;a:3]:[c:4]:[c;H0;D3;+0:5]:1-O-C.[C;D1;H3:6]-[C:7](-[OH;D1;+0:8])-[C:9]-[OH;D1;+0:10]>>[C;D1;H3:6]-[C:7]1-[C:9]-[O;H0;D2;+0:10]-[c;H0;D3;+0:1]2:[c:2]:[#16;a:3]:[c:4]:[c;H0;D3;+0:5]:2-[O;H0;D2;+0:8]-1 | null | [] | null | null | null | null | Racemic 2-methyl-2,3-dihydro-thieno[3,4-b][1,4]dioxine was synthesized by transetherification of 3,4-dimethoxythiophene with racemic 1,2-propanediol as described in COMPARATIVE EXAMPLE 1. It was characterized by GC-MS and H-NMR-spectroscopy, and exhibited no optical rotation.
Conditions: See reaction.notes.procedure_de... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Primary alcohol.Secondary alcohol | Ether.Ether | c1ccsc1 | c1scc2c1OCCO2 | c1scc2c1OCCO2 | HO- | null | null | null | CC(O)CO.COc1cscc1OC>>CC1COc2cscc2O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-38c21bccac1c466a9310412c0c189a9d | CCCCCCCCCC[C@H](O)CO.COc1cscc1OC>>CCCCCCCCCCC1COc2cscc2O1 | N#N.COC1=CSC=C1OC.C1(=CC=CC=C1)C.C([C@H](CCCCCCCCCC)O)O>>C(CCCCCCCCC)C1COC=2C(O1)=CSC2 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C@@H:11]([CH2:12][OH:13])[OH:19].CO[c:14]1[cH:15][s:16][cH:17][c:18]1OC>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]1[CH2:12][O:13][c:14]2[cH:15][s:16][cH:17][c:18]2[O:19]1 | CCCCCCCCCC[C@H](O)CO.COc1cscc1OC | CCCCCCCCCCC1COc2cscc2O1 | null | O.C1(=CC=C(C=C1)S(=O)(=O)O)C | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 27a88f912a54d2a9c5080f339a9b1dc6565f1d8c89ad4e25d07c18a8cc4561ec | d3cf88dd21c2b1133a535341fad8736ebfcb343cc20bb0a78301ecc79ada442a | c1scc2c1OCCO2 | C-O-[c;H0;D3;+0:1]1:[c:2]:[#16;a:3]:[c:4]:[c;H0;D3;+0:5]:1-O-C.[C:6]-[C:7]-[C@H;D3;+0:8](-[OH;D1;+0:9])-[C:10]-[OH;D1;+0:11]>>[C:6]-[C:7]-[CH;D3;+0:8]1-[C:10]-[O;H0;D2;+0:11]-[c;H0;D3;+0:1]2:[c:2]:[#16;a:3]:[c:4]:[c;H0;D3;+0:5]:2-[O;H0;D2;+0:9]-1 | 68.8 | [{"value": 68.8, "product": "C(CCCCCCCCC)C1COC=2C(O1)=CSC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3,4-dimethoxythiophene (1.90 g), toluene (30 ml), (S)-1,2-dodecanediol (2.50 g) and p-toluenesulfonic acid monohydrate (100 mg) was heated at 95° C., continuously leading a N2-stream over the solution. After 24 h the reaction mixture was poured into ethyl acetate, washed with NaHCO3 and the organic phase ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Primary alcohol.Secondary alcohol | Ether.Ether | c1ccsc1 | c1scc2c1OCCO2 | c1scc2c1OCCO2 | HO- | O.C1(=CC=C(C=C1)S(=O)(=O)O)C.C(C)(=O)OCC | null | null | CCCCCCCCCC[C@H](O)CO.COc1cscc1OC>O.C1(=CC=C(C=C1)S(=O)(=O)O)C.C(C)(=O)OCC>CCCCCCCCCCC1COc2cscc2O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ea20d853f7c44473a5eaaef5b2e39442 | CCCCCCCCCCC(O)CO.COc1cscc1OC>>CCCCCCCCCCC1COc2cscc2O1 | COC1=CSC=C1OC.C(C(CCCCCCCCCC)O)O>>C(CCCCCCCCC)C1COC=2C(O1)=CSC2 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]([CH2:12][OH:13])[OH:19].CO[c:14]1[cH:15][s:16][cH:17][c:18]1OC>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]1[CH2:12][O:13][c:14]2[cH:15][s:16][cH:17][c:18]2[O:19]1 | CCCCCCCCCCC(O)CO.COc1cscc1OC | CCCCCCCCCCC1COc2cscc2O1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 27a88f912a54d2a9c5080f339a9b1dc6565f1d8c89ad4e25d07c18a8cc4561ec | d3cf88dd21c2b1133a535341fad8736ebfcb343cc20bb0a78301ecc79ada442a | c1scc2c1OCCO2 | C-O-[c;H0;D3;+0:1]1:[c:2]:[#16;a:3]:[c:4]:[c;H0;D3;+0:5]:1-O-C.[C:6]-[C:7](-[OH;D1;+0:8])-[C:9]-[OH;D1;+0:10]>>[C:6]-[C:7]1-[C:9]-[O;H0;D2;+0:10]-[c;H0;D3;+0:1]2:[c:2]:[#16;a:3]:[c:4]:[c;H0;D3;+0:5]:2-[O;H0;D2;+0:8]-1 | null | [] | null | null | null | null | Racemic 2-n-decyl-2,3-dihydro-thieno[3,4-b][1,4]dioxine was synthesized by transetherification of 3,4-dimethoxythiophene with racemic 1,2-dodecanediol as described in EXAMPLE 1. It was characterized by GC-MS and H-NMR-spectroscopy, and exhibited no optical rotation.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Primary alcohol.Secondary alcohol | Ether.Ether | c1ccsc1 | c1scc2c1OCCO2 | c1scc2c1OCCO2 | HO- | null | null | null | CCCCCCCCCCC(O)CO.COc1cscc1OC>>CCCCCCCCCCC1COc2cscc2O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-519add250e7d4ab9915edef34623bdcd | CCCCCC[C@H](O)CO.COc1cscc1OC>>CCCCCCC1COc2cscc2O1 | COC1=CSC=C1OC.C([C@H](CCCCCC)O)O>>C(CCCCC)C1COC=2C(O1)=CSC2 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]([CH2:8][OH:9])[OH:15].CO[c:10]1[cH:11][s:12][cH:13][c:14]1OC>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]1[CH2:8][O:9][c:10]2[cH:11][s:12][cH:13][c:14]2[O:15]1 | CCCCCC[C@H](O)CO.COc1cscc1OC | CCCCCCC1COc2cscc2O1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 27a88f912a54d2a9c5080f339a9b1dc6565f1d8c89ad4e25d07c18a8cc4561ec | d3cf88dd21c2b1133a535341fad8736ebfcb343cc20bb0a78301ecc79ada442a | c1scc2c1OCCO2 | C-O-[c;H0;D3;+0:1]1:[c:2]:[#16;a:3]:[c:4]:[c;H0;D3;+0:5]:1-O-C.[C:6]-[C:7]-[C@H;D3;+0:8](-[OH;D1;+0:9])-[C:10]-[OH;D1;+0:11]>>[C:6]-[C:7]-[CH;D3;+0:8]1-[C:10]-[O;H0;D2;+0:11]-[c;H0;D3;+0:1]2:[c:2]:[#16;a:3]:[c:4]:[c;H0;D3;+0:5]:2-[O;H0;D2;+0:9]-1 | null | [] | null | null | null | null | Chiral 2-n-hexyl-2,3-dihydro-thieno[3,4-b][1,4]dioxine was synthesized by transetherification of 3,4-dimethoxythiophene with (S)-1,2-octanediol and purified to a purity of 99.69% as described in INVENTION EXAMPLE 1. It was characterized by GC-MS and 1H-NMR-spectroscopy, and exhibited a specific rotation of −100° at 25°... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Primary alcohol.Secondary alcohol | Ether.Ether | c1ccsc1 | c1scc2c1OCCO2 | c1scc2c1OCCO2 | HO- | null | null | null | CCCCCC[C@H](O)CO.COc1cscc1OC>>CCCCCCC1COc2cscc2O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6b01b300406b47048991d30fbf312366 | CCCCCCC(O)CO.COc1cscc1OC>>CCCCCCC1COc2cscc2O1 | COC1=CSC=C1OC.C(C(CCCCCC)O)O>>C(CCCCC)C1COC=2C(O1)=CSC2 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]([CH2:8][OH:9])[OH:15].CO[c:10]1[cH:11][s:12][cH:13][c:14]1OC>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]1[CH2:8][O:9][c:10]2[cH:11][s:12][cH:13][c:14]2[O:15]1 | CCCCCCC(O)CO.COc1cscc1OC | CCCCCCC1COc2cscc2O1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 27a88f912a54d2a9c5080f339a9b1dc6565f1d8c89ad4e25d07c18a8cc4561ec | d3cf88dd21c2b1133a535341fad8736ebfcb343cc20bb0a78301ecc79ada442a | c1scc2c1OCCO2 | C-O-[c;H0;D3;+0:1]1:[c:2]:[#16;a:3]:[c:4]:[c;H0;D3;+0:5]:1-O-C.[C:6]-[C:7](-[OH;D1;+0:8])-[C:9]-[OH;D1;+0:10]>>[C:6]-[C:7]1-[C:9]-[O;H0;D2;+0:10]-[c;H0;D3;+0:1]2:[c:2]:[#16;a:3]:[c:4]:[c;H0;D3;+0:5]:2-[O;H0;D2;+0:8]-1 | null | [] | null | null | null | null | Racemic 2-n-hexyl-2,3-dihydro-thieno[3,4-b][1,4]dioxine was synthesized by transetherification of 3,4-dimethoxythiophene with racemic 1,2-octanediol as described in EXAMPLE 1. It was characterized by GC-MS and 1H-NMR-spectroscopy, and exhibited no optical rotation.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Primary alcohol.Secondary alcohol | Ether.Ether | c1ccsc1 | c1scc2c1OCCO2 | c1scc2c1OCCO2 | HO- | null | null | null | CCCCCCC(O)CO.COc1cscc1OC>>CCCCCCC1COc2cscc2O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0c7091e2d6c4451cab60f2773711d577 | CCCCCCCC[C@H](O)CO.COc1cscc1OC>>CCCCCCCCC1COc2cscc2O1 | COC1=CSC=C1OC.C([C@H](CCCCCCCC)O)O>>C(CCCCCCC)C1COC=2C(O1)=CSC2 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C@@H:9]([CH2:10][OH:11])[OH:17].CO[c:12]1[cH:13][s:14][cH:15][c:16]1OC>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]1[CH2:10][O:11][c:12]2[cH:13][s:14][cH:15][c:16]2[O:17]1 | CCCCCCCC[C@H](O)CO.COc1cscc1OC | CCCCCCCCC1COc2cscc2O1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 27a88f912a54d2a9c5080f339a9b1dc6565f1d8c89ad4e25d07c18a8cc4561ec | d3cf88dd21c2b1133a535341fad8736ebfcb343cc20bb0a78301ecc79ada442a | c1scc2c1OCCO2 | C-O-[c;H0;D3;+0:1]1:[c:2]:[#16;a:3]:[c:4]:[c;H0;D3;+0:5]:1-O-C.[C:6]-[C:7]-[C@H;D3;+0:8](-[OH;D1;+0:9])-[C:10]-[OH;D1;+0:11]>>[C:6]-[C:7]-[CH;D3;+0:8]1-[C:10]-[O;H0;D2;+0:11]-[c;H0;D3;+0:1]2:[c:2]:[#16;a:3]:[c:4]:[c;H0;D3;+0:5]:2-[O;H0;D2;+0:9]-1 | null | [] | null | null | null | null | Chiral 2-n-octyl-2,3-dihydro-thieno[3,4-b][1,4]dioxine was synthesized by transetherification of 3,4-dimethoxythiophene with (S)-1,2-decanediol and purified to a purity of 99.24% as described in INVENTION EXAMPLE 1. It was characterized by GC-MS and 1H-NMR-spectroscopy, and exhibited a specific rotation of −88° at 25° ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Primary alcohol.Secondary alcohol | Ether.Ether | c1ccsc1 | c1scc2c1OCCO2 | c1scc2c1OCCO2 | HO- | null | null | null | CCCCCCCC[C@H](O)CO.COc1cscc1OC>>CCCCCCCCC1COc2cscc2O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1304dd98d8844e43abc758850cf83b9e | CCCCCCCCCCCC[C@H](O)CO.COc1cscc1OC>>CCCCCCCCCCCCC1COc2cscc2O1 | COC1=CSC=C1OC.C([C@H](CCCCCCCCCCCC)O)O>>C(CCCCCCCCCCC)C1COC=2C(O1)=CSC2 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C@@H:13]([CH2:14][OH:15])[OH:21].CO[c:16]1[cH:17][s:18][cH:19][c:20]1OC>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]1[CH2:14][O:15][c:16]2[cH:17][s:18][cH:19][c:20]2[O:21]1 | CCCCCCCCCCCC[C@H](O)CO.COc1cscc1OC | CCCCCCCCCCCCC1COc2cscc2O1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 27a88f912a54d2a9c5080f339a9b1dc6565f1d8c89ad4e25d07c18a8cc4561ec | d3cf88dd21c2b1133a535341fad8736ebfcb343cc20bb0a78301ecc79ada442a | c1scc2c1OCCO2 | C-O-[c;H0;D3;+0:1]1:[c:2]:[#16;a:3]:[c:4]:[c;H0;D3;+0:5]:1-O-C.[C:6]-[C:7]-[C@H;D3;+0:8](-[OH;D1;+0:9])-[C:10]-[OH;D1;+0:11]>>[C:6]-[C:7]-[CH;D3;+0:8]1-[C:10]-[O;H0;D2;+0:11]-[c;H0;D3;+0:1]2:[c:2]:[#16;a:3]:[c:4]:[c;H0;D3;+0:5]:2-[O;H0;D2;+0:9]-1 | null | [] | null | null | null | null | Chiral 2-n-dodecyl-2,3-dihydro-thieno[3,4-b][1,4]dioxine was synthesized by transetherification of 3,4-dimethoxythiophene with (S)-1,2-tetradecanediol and purified to a purity of 98.01% as described in INVENTION EXAMPLE 1. It was characterized by GC-MS and 1H-NMR-spectroscopy, and exhibited a specific rotation of −65° ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Primary alcohol.Secondary alcohol | Ether.Ether | c1ccsc1 | c1scc2c1OCCO2 | c1scc2c1OCCO2 | HO- | null | null | null | CCCCCCCCCCCC[C@H](O)CO.COc1cscc1OC>>CCCCCCCCCCCCC1COc2cscc2O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0fb2734542694c16affef6dddddfd246 | CCOC(=O)C(Br)(Br)C(=O)OCC.Oc1ccccc1O>>CCOC(=O)C1(C(=O)OCC)Oc2ccccc2O1 | C=1(O)C(O)=CC=CC1.BrC(C(=O)OCC)(C(=O)OCC)Br.C([O-])([O-])=O.[K+].[K+]>>C(C)OC(=O)C1(OC2=C(O1)C=CC=C2)C(=O)OCC | Br[C:6](Br)([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:7](=[O:8])[O:9][CH2:10][CH3:11].[OH:12][c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[OH:19]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1([C:7](=[O:8])[O:9][CH2:10][CH3:11])[O:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[O:19]1 | CCOC(=O)C(Br)(Br)C(=O)OCC.Oc1ccccc1O | CCOC(=O)C1(C(=O)OCC)Oc2ccccc2O1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | af92e8ae1f27b7a1e6f478492a6f48fd98b71b8d2ef436c713fd3da904924b6f | 661a42d0ac7fd9eb76e924a46e5fae3d564c0d30f9b9482dcc715291d9bc27ca | c1ccc2c(c1)OCO2 | Br-[C;H0;D4;+0:1](-Br)(-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9].[OH;D1;+0:10]-[c:11](:[c:12]):[c:13](-[OH;D1;+0:14]):[c:15]>>[C:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[C;H0;D4;+0:1]1(-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-[O;H0;D2;+0:10]-[c:11](:[c:12]):[c:13](:[c:15])-[O;H0;D2;+0:14]-1 | 73.2 | [{"value": 73.2, "product": "C(C)OC(=O)C1(OC2=C(O1)C=CC=C2)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Ex-1A: Catechol (2.2 g, 20 mmol) was dissolved in acetone. Diethyl dibromomalonate (7.0 g, 22 mmol) and potassium carbonate (2.76 g) were added, and the mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, and water was added to the residue. The residue was extracted with d... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Ester.Ester.Aromatic alcohol.Aromatic alcohol | Ester.Ester.Ether.Ether | null | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | HBr | CC(=O)C | null | 8 | CCOC(=O)C(Br)(Br)C(=O)OCC.Oc1ccccc1O>CC(=O)C>CCOC(=O)C1(C(=O)OCC)Oc2ccccc2O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ffe68f0513c241bd8c2d2a4b859c46bf | COc1cc(C=O)cc(Br)c1OC.OB(O)c1cccs1>>COc1cc(C=O)cc(-c2cccs2)c1OC | S1C(=CC=C1)B(O)O.BrC=1C(=C(C=C(C=O)C1)OC)OC>>COC=1C=C(C=O)C=C(C1OC)C=1SC=CC1 | Br[c:9]1[cH:8][c:5]([CH:6]=[O:7])[cH:4][c:3]([O:2][CH3:1])[c:15]1[O:16][CH3:17].OB(O)[c:10]1[cH:11][cH:12][cH:13][s:14]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]=[O:7])[cH:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][s:14]2)[c:15]1[O:16][CH3:17] | COc1cc(C=O)cc(Br)c1OC.OB(O)c1cccs1 | COc1cc(C=O)cc(-c2cccs2)c1OC | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C([O-])([O-])=O.[Na+].[Na+] | COCCOC | C-C Coupling | Suzuki coupling with boronic acids | a9e750b5cb26673fc488a731642519fa5963d6a2e4d2eeb976470c7f17606def | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccs2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4]=[O;D1;H0:5]):[c:6](-[#8:7]):[c:8].O-B(-O)-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[c:13]:1>>[#8:7]-[c:6](:[c:8]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[c:13]:1):[c:2]:[c:3]-[C:4]=[O;D1;H0:5] | 91 | [{"value": 90.0, "product": "COC=1C=C(C=O)C=C(C1OC)C=1SC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.0, "product": "COC=1C=C(C=O)C=C(C1OC)C=1SC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Ex-1D: A solution of 5-bromo-3,4-dimethoxybenzaldehyde (10.23 g, 41.7 mmol) in 359 mL of ethylene glycol dimethyl ether was purged with nitrogen gas for 30 min. The solution was treated with tetrakis(triphenylphosphine)palladium(0) (5.0 g, 4.3 mmol), thiophene-2-boronic acid (8.01 g, 62.6 mmol), and a solution of 2 N s... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccsc1 | c1ccccc1.c1ccsc1 | c1ccccc1.c1ccsc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C([O-])([O-])=O.[Na+].[Na+].COCCOC | null | null | COc1cc(C=O)cc(Br)c1OC.OB(O)c1cccs1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C([O-])([O-])=O.[Na+].[Na+].COCCOC>COc1cc(C=O)cc(-c2cccs2)c1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c0e35e5b2743478c94c3b16684e200e4 | COc1cc(OC)c(C=O)cc1Br.OB(O)c1cc2ccccc2s1>>COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=O | O.S1C2=C(C=C1B(O)O)C=CC=C2.C([O-])([O-])=O.[Na+].[Na+].BrC=1C(=CC(=C(C=O)C1)OC)OC>>S1C2=C(C=C1C=1C(=CC(=C(C=O)C1)OC)OC)C=CC=C2 | Br[c:8]1[c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[c:19]([CH:20]=[O:21])[cH:18]1.OB(O)[c:9]1[cH:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[s:17]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[s:17]2)[cH:18][c:19]1[CH:20]=[O:21] | COc1cc(OC)c(C=O)cc1Br.OB(O)c1cc2ccccc2s1 | COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=O | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | COCCOC | C-C Coupling | Suzuki coupling with boronic acids | a1259a94b31ac9f1988cb839e0910c5b2437b7522341904299ff46277eacea87 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc3ccccc3s2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4]=[O;D1;H0:5]):[c:6](-[#8:7]):[c:8].O-B(-O)-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[c:13]:1>>[#8:7]-[c:6](:[c:8]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[c:13]:1):[c:2]:[c:3]-[C:4]=[O;D1;H0:5] | 83 | [{"value": 83.0, "product": "S1C2=C(C=C1C=1C(=CC(=C(C=O)C1)OC)OC)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.6, "product": "S1C2=C(C=C1C=1C(=CC(=C(C=O)C1)OC)OC)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | Ex-3A: A sample of 5-bromo-2,4-dimethoxybenzaldehyde (4.9 g, 20.0 mmol) was dissolved in ethylene glycol dimethyl ether (50 mL). Tetrakis(triphenylphosphine)palladium(0) (2.32 g, 2 mmol) was added, and the mixture was stirred at room temperature under nitrogen for 5 min. Benzo[b]thiophene-2-boronic acid (4.27 g, 24 mmo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2sccc2c1 | c1ccccc1.c1ccc2sccc2c1 | c1ccccc1.c1ccc2sccc2c1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.COCCOC | null | 0.083333 | COc1cc(OC)c(C=O)cc1Br.OB(O)c1cc2ccccc2s1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.COCCOC>COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c42bc816958d46fdb487d1fa20a0e374 | COc1cc(OC)c(C=O)cc1Br.OB(O)c1cc2ccccc2s1>>COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=O | BrC=1C(=CC(=C(C=O)C1)OC)OC.S1C2=C(C=C1B(O)O)C=CC=C2>>S1C2=C(C=C1C=1C(=CC(=C(C=O)C1)OC)OC)C=CC=C2 | Br[c:8]1[c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[c:19]([CH:20]=[O:21])[cH:18]1.OB(O)[c:9]1[cH:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[s:17]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[s:17]2)[cH:18][c:19]1[CH:20]=[O:21] | COc1cc(OC)c(C=O)cc1Br.OB(O)c1cc2ccccc2s1 | COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=O | null | null | C1CCOC1 | C-C Coupling | Suzuki coupling with boronic acids | a1259a94b31ac9f1988cb839e0910c5b2437b7522341904299ff46277eacea87 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc3ccccc3s2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4]=[O;D1;H0:5]):[c:6](-[#8:7]):[c:8].O-B(-O)-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[c:13]:1>>[#8:7]-[c:6](:[c:8]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[c:13]:1):[c:2]:[c:3]-[C:4]=[O;D1;H0:5] | 97.5 | [{"value": 97.0, "product": "S1C2=C(C=C1C=1C(=CC(=C(C=O)C1)OC)OC)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.5, "product": "S1C2=C(C=C1C=1C(=CC(=C(C=O)C1)OC)OC)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 1.5 | HOUR | An alternative procedure: 5-bromo-2,4-dimethoxybenzaldehyde (20 g), benzo[b]thiophene-2-boronic acid (16 g) and THF (200 mL) were sequentially charged into a clean reaction vessel fitted with a reflux condenser, mechanical stirrer and nitrogen inlet adapter. Nitrogen was bubbled into the resulting solution for 20 min f... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2sccc2c1 | c1ccccc1.c1ccc2sccc2c1 | c1ccccc1.c1ccc2sccc2c1 | HBr.B | C1CCOC1 | 60 | 1.5 | COc1cc(OC)c(C=O)cc1Br.OB(O)c1cc2ccccc2s1>C1CCOC1>COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-80ec1d096bde430b80ffb02cef23687a | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=O>>COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | C(C)(=O)C1=CC=C(C(=O)O)C=C1.S1C2=C(C=C1C=1C(=CC(=C(C=O)C1)OC)OC)C=CC=C2.[OH-].[Na+]>>S1C2=C(C=C1C=1C(=CC(=C(C1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)OC)OC)C=CC=C2 | [CH3:21][C:22](=[O:23])[c:24]1[cH:25][cH:26][c:27]([C:28](=[O:29])[OH:30])[cH:31][cH:32]1.O=[CH:20][c:19]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[s:17]2)[cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:13][cH:14... | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=O | COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | null | null | O.CN(C=O)C | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cc3ccccc3s2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 54 | [{"value": 54.0, "product": "S1C2=C(C=C1C=1C(=CC(=C(C1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)OC)OC)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 4-acetylbenzoic acid (1.50 g, 9.1 mmol) and 5-(benzo[b]thien-2-yl)-2,4-dimethoxybenzaldehyde from Ex-3A (3.27 g, 11.0 mmol) in N,N-dimethylformamide (76 mL) was added a solution of sodium hydroxide (5 M, 7.3 mL, 36.5 mmol). The reaction mixture was allowed to stir at room temperature for 2 h and was th... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccc2sccc2c1.c1ccccc1 | HO- | O.CN(C=O)C | null | 2 | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=O>O.CN(C=O)C>COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dbc0fbc72a9c45638282d8de69c914ca | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=O>>COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | O([Li])C.S1C2=C(C=C1C=1C(=CC(=C(C=O)C1)OC)OC)C=CC=C2.C(C)(=O)C1=CC=C(C(=O)O)C=C1.CO>>S1C2=C(C=C1C=1C(=CC(=C(C1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)OC)OC)C=CC=C2 | [CH3:21][C:22](=[O:23])[c:24]1[cH:25][cH:26][c:27]([C:28](=[O:29])[OH:30])[cH:31][cH:32]1.O=[CH:20][c:19]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[s:17]2)[cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:13][cH:14... | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=O | COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | null | null | CCCCCCC.O.CN(C)C=O | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cc3ccccc3s2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 87 | [{"value": 87.0, "product": "S1C2=C(C=C1C=1C(=CC(=C(C1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)OC)OC)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | An alternative procedure: 5-(Benzo[b]thien-2-yl)-2,4-dimethoxybenzaldehyde from Ex-3A (42.3 g), 4-acetylbenzoic acid (22.1 g), MeOH (250 mL) and DMF (600 mL) were sequentially charged into a clean reaction vessel fitted with a mechanical stirrer and nitrogen inlet adapter. After complete dissolution, LiOMe (10.5 g) was... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccc2sccc2c1.c1ccccc1 | HO- | CCCCCCC.O.CN(C)C=O | null | 2 | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=O>CCCCCCC.O.CN(C)C=O>COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-910e529f4bf849c9af867aee4fa5dbc9 | O=Cc1ccc(Br)cc1.OB(O)c1nccs1>>O=Cc1ccc(-c2nccs2)cc1 | BrC1=CC=C(C=O)C=C1.S1C(=NC=C1)B(O)O>>S1C(=NC=C1)C1=CC=C(C=O)C=C1 | Br[c:6]1[cH:5][cH:4][c:3]([CH:2]=[O:1])[cH:13][cH:12]1.OB(O)[c:7]1[n:8][cH:9][cH:10][s:11]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][cH:9][cH:10][s:11]2)[cH:12][cH:13]1 | O=Cc1ccc(Br)cc1.OB(O)c1nccs1 | O=Cc1ccc(-c2nccs2)cc1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | f4565b4e9dabb73b09ab28617730b65da20c1e6e94d183a4606dbf1402c06c05 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2nccs2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6]1:[#16;a:7]:[c:8]:[c:9]:[#7;a:10]:1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6]1:[#16;a:7]:[c:8]:[c:9]:[#7;a:10]:1):[c:4]:[c:5] | 82 | [{"value": 82.0, "product": "S1C(=NC=C1)C1=CC=C(C=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Ex-5A: 4-Thiazol-2-yl-benzaldehyde was prepared from 4-bromobenzaldehyde and thiazole-2-boronic acid in a similar manner as described in Ex-3A, 82% yield. 1H-NMR (CDCl3) δ 10.07 (s, 1H), 8.15 (d, J=8 Hz, 2H), 7.95–7.98 (m, 3H), 7.45 (d, J=3 Hz, 1H). HMRS (EI) calcd. for C10H7NOS: 189.0248; found: 189.0242.
Conditions: ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1cscn1 | c1ccccc1.c1cscn1 | c1ccccc1.c1cscn1 | HBr.B | null | null | null | O=Cc1ccc(Br)cc1.OB(O)c1nccs1>>O=Cc1ccc(-c2nccs2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f16ab514fd824af09929b4295ce2adb4 | COc1cc(OC)c(C=O)cc1Br.OB(O)c1cccs1>>COc1cc(OC)c(-c2cccs2)cc1C=O | BrC=1C(=CC(=C(C=O)C1)OC)OC.S1C(=CC=C1)B(O)O>>COC1=C(C=O)C=C(C(=C1)OC)C=1SC=CC1 | Br[c:8]1[c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[c:15]([CH:16]=[O:17])[cH:14]1.OB(O)[c:9]1[cH:10][cH:11][cH:12][s:13]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][cH:11][cH:12][s:13]2)[cH:14][c:15]1[CH:16]=[O:17] | COc1cc(OC)c(C=O)cc1Br.OB(O)c1cccs1 | COc1cc(OC)c(-c2cccs2)cc1C=O | null | null | C1CCOC1 | C-C Coupling | Suzuki coupling with boronic acids | a9e750b5cb26673fc488a731642519fa5963d6a2e4d2eeb976470c7f17606def | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccs2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4]=[O;D1;H0:5]):[c:6](-[#8:7]):[c:8].O-B(-O)-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[c:13]:1>>[#8:7]-[c:6](:[c:8]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[c:13]:1):[c:2]:[c:3]-[C:4]=[O;D1;H0:5] | 94 | [{"value": 94.0, "product": "COC1=C(C=O)C=C(C(=C1)OC)C=1SC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.9, "product": "COC1=C(C=O)C=C(C(=C1)OC)C=1SC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | Ex-6A: 5-bromo-2,4-dimethoxybenzaldehyde (20.3 g), thiophene-2-boronic acid (11.6 g) and THF (200 mL) were sequentially charged into a clean reaction vessel fitted with a reflux condenser, mechanical stirrer and nitrogen inlet adapter. Nitrogen was bubbled into the resulting solution for 20 min followed by the sequenti... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccsc1 | c1ccccc1.c1ccsc1 | c1ccccc1.c1ccsc1 | HBr.B | C1CCOC1 | 60 | null | COc1cc(OC)c(C=O)cc1Br.OB(O)c1cccs1>C1CCOC1>COc1cc(OC)c(-c2cccs2)cc1C=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2cfd49376d34445eab0e8f2771463ec3 | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2cccs2)cc1C=O>>COc1cc(OC)c(-c2cccs2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | C(C)(C)OC(=O)C.COC1=C(C=O)C=C(C(=C1)OC)C=1SC=CC1.C(C)(=O)C1=CC=C(C(=O)O)C=C1.Cl.O([Li])C>>COC1=C(C=C(C(=C1)OC)C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1 | [CH3:17][C:18](=[O:19])[c:20]1[cH:21][cH:22][c:23]([C:24](=[O:25])[OH:26])[cH:27][cH:28]1.O=[CH:16][c:15]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][cH:11][cH:12][s:13]2)[cH:14]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][cH:11][cH:12][s:13]2)[cH:14][c:15]1/[CH:16]=[CH:17]/[C... | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2cccs2)cc1C=O | COc1cc(OC)c(-c2cccs2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | null | null | CO.O.CN(C)C=O | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cccs2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 75 | [{"value": 75.0, "product": "COC1=C(C=C(C(=C1)OC)C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | 2,4-Dimethoxy-5-thiophen-2-yl-benzaldehyde from Ex-6A (7.81 g), 4-acetylbenzoic acid (4.9 g), MeOH (60 mL) and DMF (150 mL) were sequentially charged into a clean reaction vessel fitted with a stir bar and nitrogen inlet adapter. After complete dissolution LiOMe (4.60 g) was added and the resulting solution was aged fo... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccsc1.c1ccccc1 | HO- | CO.O.CN(C)C=O | null | 5 | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2cccs2)cc1C=O>CO.O.CN(C)C=O>COc1cc(OC)c(-c2cccs2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-98c5286fa77743c5adb9e6a08b1dd3b4 | CC(=O)c1ccc(Br)cc1.OB(O)c1cccs1>>CC(=O)c1ccc(-c2cccs2)cc1 | BrC1=CC=C(C=C1)C(C)=O.S1C(=CC=C1)B(O)O.C([O-])([O-])=O.[Na+].[Na+]>>S1C(=CC=C1)C1=CC=C(C=C1)C(C)=O | Br[c:7]1[cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:14][cH:13]1.OB(O)[c:8]1[cH:9][cH:10][cH:11][s:12]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][s:12]2)[cH:13][cH:14]1 | CC(=O)c1ccc(Br)cc1.OB(O)c1cccs1 | CC(=O)c1ccc(-c2cccs2)cc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | COCCOC | C-C Coupling | Suzuki coupling with boronic acids | a9e750b5cb26673fc488a731642519fa5963d6a2e4d2eeb976470c7f17606def | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccs2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6]1:[#16;a:7]:[c:8]:[c:9]:[c:10]:1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6]1:[#16;a:7]:[c:8]:[c:9]:[c:10]:1):[c:4]:[c:5] | 95.2 | [{"value": 95.0, "product": "S1C(=CC=C1)C1=CC=C(C=C1)C(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.2, "product": "S1C(=CC=C1)C1=CC=C(C=C1)C(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Ex-17A: 4′-Bromoacetophenone (3.98 g, 20 mmol) was dissolved in ethylene glycol dimethyl ether and then the solution was degassed with nitrogen for 15 minutes. Tetrakis(triphenylphosphine)palladium(0) (2.31 g, 2 mmol) was added, and the solution was further degassed for 10 minutes. Thiophene-2-boronic acid (3.07 g, 24 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccsc1 | c1ccccc1.c1ccsc1 | c1ccccc1.c1ccsc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.COCCOC | null | null | CC(=O)c1ccc(Br)cc1.OB(O)c1cccs1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.COCCOC>CC(=O)c1ccc(-c2cccs2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e7d528ac61244a92ae77ef18a8dc8431 | COc1cc(-c2cccs2)ccc1C(C)=O.O=Cc1ccc(C(=O)O)cc1>>COc1cc(-c2cccs2)ccc1C(=O)/C=C/c1ccc(C(=O)O)cc1 | COC1=C(C=CC(=C1)C=1SC=CC1)C(C)=O.C(=O)(O)C1=CC=C(C=O)C=C1>>COC1=C(C=CC(=C1)C=1SC=CC1)C(/C=C/C1=CC=C(C(=O)O)C=C1)=O | [CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][s:10]2)[cH:11][cH:12][c:13]1[C:14](=[O:15])[CH3:16].O=[CH:17][c:18]1[cH:19][cH:20][c:21]([C:22](=[O:23])[OH:24])[cH:25][cH:26]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][s:10]2)[cH:11][cH:12][c:13]1[C:14](=[O:15])/[CH:16]=[CH:17]/[c:18]1[cH:19][cH:2... | COc1cc(-c2cccs2)ccc1C(C)=O.O=Cc1ccc(C(=O)O)cc1 | COc1cc(-c2cccs2)ccc1C(=O)/C=C/c1ccc(C(=O)O)cc1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1ccccc1)c1ccc(-c2cccs2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The title compound was prepared by condensing 1-(2-methoxy-4-thiophen-2-yl-phenyl)-ethanone (Ex-19A) and 4-carboxybenzaldehyde in a similar manner as described in Ex-17 except an acidic workup. Yellow solid, mp 193–195° C. 1H-NMR (CDCl3) □ 7.70 (d, J=8 Hz, 2H), 7.38 (d, J=8 Hz, 1H), 7.07–7.16 (m, 4H), 6.75–6.80 (m, 4H)... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccsc1.c1ccccc1 | HO- | null | null | null | COc1cc(-c2cccs2)ccc1C(C)=O.O=Cc1ccc(C(=O)O)cc1>>COc1cc(-c2cccs2)ccc1C(=O)/C=C/c1ccc(C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c5484a2773bb47e29713adbda40748dc | O=Cc1ccc(F)c(Br)c1.OB(O)c1cccs1>>O=Cc1ccc(F)c(-c2cccs2)c1 | O.BrC=1C=C(C=O)C=CC1F.S1C(=CC=C1)B(O)O.C([O-])([O-])=O.[Na+].[Na+]>>FC1=C(C=C(C=O)C=C1)C=1SC=CC1 | Br[c:8]1[c:6]([F:7])[cH:5][cH:4][c:3]([CH:2]=[O:1])[cH:14]1.OB(O)[c:9]1[cH:10][cH:11][cH:12][s:13]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([F:7])[c:8](-[c:9]2[cH:10][cH:11][cH:12][s:13]2)[cH:14]1 | O=Cc1ccc(F)c(Br)c1.OB(O)c1cccs1 | O=Cc1ccc(F)c(-c2cccs2)c1 | null | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | COCCOC | C-C Coupling | Suzuki coupling with boronic acids | a9e750b5cb26673fc488a731642519fa5963d6a2e4d2eeb976470c7f17606def | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccs2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4]=[O;D1;H0:5]):[c:6](-[F;D1;H0:7]):[c:8].O-B(-O)-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[c:13]:1>>[F;D1;H0:7]-[c:6](:[c:8]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[c:13]:1):[c:2]:[c:3]-[C:4]=[O;D1;H0:5] | 95 | [{"value": 95.0, "product": "FC1=C(C=C(C=O)C=C1)C=1SC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.6, "product": "FC1=C(C=C(C=O)C=C1)C=1SC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Ex-20A: A solution of 3-bromo-4-flouro-benzaldehyde (5.0 g, 24.6 mmol) and thiophene-2-boronic acid (4.7 g, 37.0 mmol) in ethylene glycol dimethyl ether (100 mL) was stirred at room temperature under nitrogen for 15 min. Then tetrakis(triphenylphosphine)-palladium(0) (2.8 g, 2.42 mmol) and a sodium carbonate solution (... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccsc1 | c1ccccc1.c1ccsc1 | c1ccccc1.c1ccsc1 | HBr.B | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.COCCOC | null | null | O=Cc1ccc(F)c(Br)c1.OB(O)c1cccs1>[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.COCCOC>O=Cc1ccc(F)c(-c2cccs2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b5f1fe8613fa4da4a8336dfb85be8fde | C1CCNC1.O=Cc1ccc(F)c(-c2cccs2)c1>>O=Cc1ccc(N2CCCC2)c(-c2cccs2)c1 | O.FC1=C(C=C(C=O)C=C1)C=1SC=CC1.N1CCCC1.C(=O)([O-])[O-].[K+].[K+]>>N1(CCCC1)C1=C(C=C(C=O)C=C1)C=1SC=CC1 | [NH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1.F[c:6]1[cH:5][cH:4][c:3]([CH:2]=[O:1])[cH:18][c:12]1-[c:13]1[cH:14][cH:15][cH:16][s:17]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][CH2:10][CH2:11]2)[c:12](-[c:13]2[cH:14][cH:15][cH:16][s:17]2)[cH:18]1 | C1CCNC1.O=Cc1ccc(F)c(-c2cccs2)c1 | O=Cc1ccc(N2CCCC2)c(-c2cccs2)c1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1csc(-c2ccccc2N2CCCC2)c1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[c:5]:[#16;a:6]):[c:7].[C:8]1-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[#16;a:6]:[c:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[C:12]-[C:11]-1):[c:2]:[c:3] | 29 | [{"value": 29.0, "product": "N1(CCCC1)C1=C(C=C(C=O)C=C1)C=1SC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 28.9, "product": "N1(CCCC1)C1=C(C=C(C=O)C=C1)C=1SC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Ex-20B: A solution of 4-fluoro-3-(thiophen-2-yl)-benzaldehyde (1.11 g, 5.38 mmol) from Ex-20A and pyrrolidine (13.0 g, 183.0 mmol) in dimethylformamide (30 mL) was treated with solid K2CO3 (1.7 g, 12.3 mmol), and the resulting mixture was stirred at reflux for 1 week. Upon cooling to room temperature, the reaction was ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccccc1 | c1ccccc1.C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1.c1ccsc1 | HF | CN(C=O)C | null | null | C1CCNC1.O=Cc1ccc(F)c(-c2cccs2)c1>CN(C=O)C>O=Cc1ccc(N2CCCC2)c(-c2cccs2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3710f1d466844c3a80b01c2a0dd8ec27 | CC(=O)c1ccc(C(=O)O)cc1.O=Cc1ccc(N2CCCC2)c(-c2cccs2)c1>>O=C(O)c1ccc(C(=O)/C=C/c2ccc(N3CCCC3)c(-c3cccs3)c2)cc1 | N1(CCCC1)C1=C(C=C(C=O)C=C1)C=1SC=CC1.C(C)(=O)C1=CC=C(C(=O)O)C=C1.[OH-].[Na+]>>N1(CCCC1)C1=C(C=C(C=C1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)C=1SC=CC1 | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[CH3:10])[cH:28][cH:29]1.O=[CH:11][c:12]1[cH:13][cH:14][c:15]([N:16]2[CH2:17][CH2:18][CH2:19][CH2:20]2)[c:21](-[c:22]2[cH:23][cH:24][cH:25][s:26]2)[cH:27]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])/[CH:10]=[CH:11]/[c:12]2[cH:13][cH:14][c:15]([N:16]... | CC(=O)c1ccc(C(=O)O)cc1.O=Cc1ccc(N2CCCC2)c(-c2cccs2)c1 | O=C(O)c1ccc(C(=O)/C=C/c2ccc(N3CCCC3)c(-c3cccs3)c2)cc1 | null | null | O.CN(C=O)C | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1ccc(N2CCCC2)c(-c2cccs2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 13 | [{"value": 13.0, "product": "N1(CCCC1)C1=C(C=C(C=C1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)C=1SC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 12.8, "product": "N1(CCCC1)C1=C(C=C(C=C1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)C=1SC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 4-Pyrrolidin-1-yl-3-(thiophen-2-yl)-benzaldehyde (400 mg, 1.55 mmol) from Ex-20B and 4-acetylbenzoic acid (255 mg, 1.55 mmol) were dissolved in dimethylformamide (30 mL). Sodium hydroxide solution (5 N, 1.25 mL) was added in one portion, and the mixture was stirred at room temperature overnight. The reaction was dilute... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccccc1.C1CC[NH]C1.c1ccsc1 | HO- | O.CN(C=O)C | null | 8 | CC(=O)c1ccc(C(=O)O)cc1.O=Cc1ccc(N2CCCC2)c(-c2cccs2)c1>O.CN(C=O)C>O=C(O)c1ccc(C(=O)/C=C/c2ccc(N3CCCC3)c(-c3cccs3)c2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2a580c9cc4a04d5ca1251353720da926 | CC(=O)c1ccc(C(=O)O)cc1.O=Cc1ccc(F)c(-c2cccs2)c1>>O=C(O)c1ccc(C(=O)/C=C/c2ccc(F)c(-c3cccs3)c2)cc1 | FC1=C(C=C(C=O)C=C1)C=1SC=CC1.C(C)(=O)C1=CC=C(C(=O)O)C=C1.[OH-].[Na+]>>FC1=C(C=C(C=C1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)C=1SC=CC1 | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[CH3:10])[cH:24][cH:25]1.O=[CH:11][c:12]1[cH:13][cH:14][c:15]([F:16])[c:17](-[c:18]2[cH:19][cH:20][cH:21][s:22]2)[cH:23]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])/[CH:10]=[CH:11]/[c:12]2[cH:13][cH:14][c:15]([F:16])[c:17](-[c:18]3[cH:19][cH:20][cH:... | CC(=O)c1ccc(C(=O)O)cc1.O=Cc1ccc(F)c(-c2cccs2)c1 | O=C(O)c1ccc(C(=O)/C=C/c2ccc(F)c(-c3cccs3)c2)cc1 | null | null | O.CN(C=O)C | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cccs2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 53 | [{"value": 53.0, "product": "FC1=C(C=C(C=C1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)C=1SC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.7, "product": "FC1=C(C=C(C=C1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)C=1SC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 4-Fluoro-3-thiophen-2-yl-benzaldehyde (1.0 g, 4.85 mmol, from Ex-20A) and 4-acetylbenzoic acid (0.80 g, 4.87 mmol) were dissolved in dimethylformamide (55 mL). Sodium hydroxide solution (5 N, 3.88 mL) was added in one portion, and the mixture was stirred at room temperature for 3 h. The reaction was diluted with water ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccccc1.c1ccsc1 | HO- | O.CN(C=O)C | null | 3 | CC(=O)c1ccc(C(=O)O)cc1.O=Cc1ccc(F)c(-c2cccs2)c1>O.CN(C=O)C>O=C(O)c1ccc(C(=O)/C=C/c2ccc(F)c(-c3cccs3)c2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6dfae3c96f5446508413bd94bf9d0b34 | CC(=O)c1ccc(SCC(=O)O)cc1.COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=O>>COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(SCC(=O)O)cc1 | C(C)(=O)C1=CC=C(C=C1)SCC(=O)O.S1C2=C(C=C1C=1C(=CC(=C(C=O)C1)OC)OC)C=CC=C2>>S1C2=C(C=C1C=1C(=CC(=C(C1)/C=C/C(=O)C1=CC=C(C=C1)SCC(=O)O)OC)OC)C=CC=C2 | [CH3:21][C:22](=[O:23])[c:24]1[cH:25][cH:26][c:27]([S:28][CH2:29][C:30](=[O:31])[OH:32])[cH:33][cH:34]1.O=[CH:20][c:19]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[s:17]2)[cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][c:11]3[cH:12... | CC(=O)c1ccc(SCC(=O)O)cc1.COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=O | COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(SCC(=O)O)cc1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cc3ccccc3s2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The title compound was prepared by condensing (4-acetylphenylthio)acetic acid (Ex-23B) and 5-(benzo[b]thien-2-yl)-2,4-dimethoxybenzaldehyde (Ex-3A) in a similar manner as described in Ex-22. Yellow solid, mp 136–138° C. (dec.). 1H-NMR (DMSO-d6) δ 8.35 (s, 1H), 8.08 (d, J=7.4 Hz, 2H), 8.03 (d, J=16.3 Hz, 1H), 7.93–7.87 ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccc2sccc2c1.c1ccccc1 | HO- | null | null | null | CC(=O)c1ccc(SCC(=O)O)cc1.COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=O>>COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(SCC(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-df59b97702e6473b8f3c2590b665ace4 | CC(=O)c1ccc(S(=O)(=O)Cl)cc1.N>>CC(=O)c1ccc(S(N)(=O)=O)cc1 | C(C)(=O)C1=CC=C(C=C1)S(=O)(=O)Cl.N>>C(C)(=O)C1=CC=C(C=C1)S(=O)(=O)N | Cl[S:8]([c:7]1[cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:13][cH:12]1)(=[O:10])=[O:11].[NH3:9]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([S:8]([NH2:9])(=[O:10])=[O:11])[cH:12][cH:13]1 | CC(=O)c1ccc(S(=O)(=O)Cl)cc1.N | CC(=O)c1ccc(S(N)(=O)=O)cc1 | null | null | CC(=O)C | Acylation | OtherReaction | 672a14b4f1ef0b966898e1b4c118f241f21df1d6e087372155b9d0c840dac61f | 29e1633db8f1f00444181a0bcac91d574ed806fddf9165be4c8478fc32a80994 | c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH3;D0;+0:7]>>[NH2;D1;+0:7]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 93 | [{"value": 93.0, "product": "C(C)(=O)C1=CC=C(C=C1)S(=O)(=O)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.0, "product": "C(C)(=O)C1=CC=C(C=C1)S(=O)(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | Ex-26A: To a solution of 4-acetyl-benzenesulfonyl chloride (Hoffman, R. V. Org. Syn. VII, 508; 4.18 g, 19.1 mmol) in acetone (30 mL) was added ammonia (28% in water, 8.2 mL, 57.3 mmol) dropwise at 0° C. The reaction mixture was allowed to stir at 0° C. for 30 min. The precipitate was filtered and the residue was washed... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | Sulfonamide | null | null | c1ccccc1 | HCl | CC(=O)C | 0 | 0.5 | CC(=O)c1ccc(S(=O)(=O)Cl)cc1.N>CC(=O)C>CC(=O)c1ccc(S(N)(=O)=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9ccfd343f2824477a48c1ff905b1543b | CC(=O)c1ccc2[nH]ccc2c1.CI>>CC(=O)c1ccc2c(ccn2C)c1 | IC.N1C=CC2=CC(=CC=C12)C(C)=O.IC.C([O-])([O-])=O.[Cs+].[Cs+]>>CN1C=CC2=CC(=CC=C12)C(C)=O | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9][cH:10][nH:11]2)[cH:13]1.I[CH3:12]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9][cH:10][n:11]2[CH3:12])[cH:13]1 | CC(=O)c1ccc2[nH]ccc2c1.CI | CC(=O)c1ccc2c(ccn2C)c1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 5f4295751cbf2eac77c77b599ebb727e1800dd106de3a7476670f0ac76dbeba5 | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | c1ccc2[nH]ccc2c1 | I-[CH3;D1;+0:1].[c:2]:[c:3]1:[c:4]:[c:5]:[c:6]:[nH;D2;+0:7]:1>>[CH3;D1;+0:1]-[n;H0;D3;+0:7]1:[c:6]:[c:5]:[c:4]:[c:3]:1:[c:2] | 51.5 | [{"value": 51.0, "product": "CN1C=CC2=CC(=CC=C12)C(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.5, "product": "CN1C=CC2=CC(=CC=C12)C(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Ex-28A: To a solution of 1-(1H-indol-5-yl)-ethanone (Yang, Y. et al, Heterocycles, 1992, 34(6), 1169–1175; 0.45 g, 2.8 mmol) were added iodomethane (3 mL) and cesium carbonate (2.3 g, 7.1 mmol). The reaction mixture was allowed to stir at 55° C. for 1.5 day during which additional iodomethane (11 mL) was added. The rea... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HI | null | null | null | CC(=O)c1ccc2[nH]ccc2c1.CI>>CC(=O)c1ccc2c(ccn2C)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-361e00b4c4e24068ba682d59610004f6 | BrBr.COc1ccc(C=O)c(O)c1>>COc1cc(O)c(C=O)cc1Br | OC1=C(C=O)C=CC(=C1)OC.BrBr>>BrC=1C(=CC(=C(C=O)C1)O)OC | Br[Br:12].[CH3:1][O:2][c:3]1[cH:4][c:5]([OH:6])[c:7]([CH:8]=[O:9])[cH:10][cH:11]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([OH:6])[c:7]([CH:8]=[O:9])[cH:10][c:11]1[Br:12] | BrBr.COc1ccc(C=O)c(O)c1 | COc1cc(O)c(C=O)cc1Br | null | null | ClCCl | Functional Group Interconversion | Bromination | f6effe61353895b318215d8bd9b6bb1105cafbf7be8c217d748df587260b32c3 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccccc1 | Br-[Br;H0;D1;+0:1].[#8:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6]:[c:7]-[C:8]=[O;D1;H0:9]>>[#8:2]-[c:3](:[c:4]):[c;H0;D3;+0:5](-[Br;H0;D1;+0:1]):[c:6]:[c:7]-[C:8]=[O;D1;H0:9] | 80 | [{"value": 80.0, "product": "BrC=1C(=CC(=C(C=O)C1)O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.8, "product": "BrC=1C(=CC(=C(C=O)C1)O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | Ex-29A: 2-Hydroxy-4-methoxybenzaldehyde (6.0 g, 39 mmol) was dissolved in dichloromethane (50 mL) and cooled to 0° C. using an ice-water bath. Bromine (6.8 g, 43 mmol) in dichloromethane (2 mL) was added dropwise to the cooled solution and stirred for 2 h at 0° C. The mixture was warmed to room temperature and stirred ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | ClCCl | 0 | 2 | BrBr.COc1ccc(C=O)c(O)c1>ClCCl>COc1cc(O)c(C=O)cc1Br |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-07e91bbb9f5246f988cf42bf69e03215 | COCCOCCBr.COc1cc(O)c(C=O)cc1-c1cccs1>>COCCOCCOc1cc(OC)c(-c2cccs2)cc1C=O | BrCCOCCOC.OC1=C(C=O)C=C(C(=C1)OC)C=1SC=CC1.C([O-])([O-])=O.[K+].[K+]>>COC1=CC(=C(C=O)C=C1C=1SC=CC1)OCCOCCOC | Br[CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1].[OH:8][c:9]1[cH:10][c:11]([O:12][CH3:13])[c:14](-[c:15]2[cH:16][cH:17][cH:18][s:19]2)[cH:20][c:21]1[CH:22]=[O:23]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][c:11]([O:12][CH3:13])[c:14](-[c:15]2[cH:16][cH:17][cH:18][s:19]2)[cH:20][c:21]1[CH:22]=[O:23] | COCCOCCBr.COc1cc(O)c(C=O)cc1-c1cccs1 | COCCOCCOc1cc(OC)c(-c2cccs2)cc1C=O | null | null | O.CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(-c2cccs2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[O;D1;H0:4]=[C:5]-[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[c:7](:[c:9]):[c:6]-[C:5]=[O;D1;H0:4] | 87 | [{"value": 87.0, "product": "COC1=CC(=C(C=O)C=C1C=1SC=CC1)OCCOCCOC", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 1 | HOUR | Ex-29C: To a solution of 2-hydroxy-4-methoxy-5-thiophen-2-yl-benzaldehyde from Ex-29B (0.10 g, 0.43 mmol) in N,N-dimethylformamide (3 mL) was added potassium carbonate (0.18 g, 1.3 mmol) and the resulting yellow slurry was heated to 80° C. Once at 80° C., 1-bromo-2-(2-methoxyethoxy)ethane (0.24 g, 1.3 mmol) was added d... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccsc1 | HBr | O.CN(C=O)C | 80 | 1 | COCCOCCBr.COc1cc(O)c(C=O)cc1-c1cccs1>O.CN(C=O)C>COCCOCCOc1cc(OC)c(-c2cccs2)cc1C=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8fc2ef8a042a46f58b067fa79d0eba07 | CC(=O)c1ccc(C(=O)O)cc1.O=Cc1ccc(-c2cccs2)cc1F>>O=C(O)c1ccc(C(=O)/C=C/c2ccc(-c3cccs3)cc2F)cc1 | FC1=C(C=O)C=CC(=C1)C=1SC=CC1.C(C)(=O)C1=CC=C(C(=O)O)C=C1>>FC1=C(C=CC(=C1)C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1 | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[CH3:10])[cH:24][cH:25]1.O=[CH:11][c:12]1[cH:13][cH:14][c:15](-[c:16]2[cH:17][cH:18][cH:19][s:20]2)[cH:21][c:22]1[F:23]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])/[CH:10]=[CH:11]/[c:12]2[cH:13][cH:14][c:15](-[c:16]3[cH:17][cH:18][cH:19][s:20]3)[cH:2... | CC(=O)c1ccc(C(=O)O)cc1.O=Cc1ccc(-c2cccs2)cc1F | O=C(O)c1ccc(C(=O)/C=C/c2ccc(-c3cccs3)cc2F)cc1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1ccc(-c2cccs2)cc1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 71 | [{"value": 71.0, "product": "FC1=C(C=CC(=C1)C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 2-fluoro-4-thiophen-2-yl-benzaldehyde (Ex-30A) and 4-acetylbezoic acid in a similar manner as described in Ex-3. Yellow solid, 71% yield, m.p.>260° C. 1H-NMR (300 MHz, d6-DMSO): 8.19 (d, 2H, J=8.4 Hz), 8.12 (d, 1H, J=8 Hz), 8.06 (d, 2H, J=8 Hz), 7.95 (d, 1H, J=16 Hz), 7.80 ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccccc1.c1ccsc1 | HO- | null | null | null | CC(=O)c1ccc(C(=O)O)cc1.O=Cc1ccc(-c2cccs2)cc1F>>O=C(O)c1ccc(C(=O)/C=C/c2ccc(-c3cccs3)cc2F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a1360300cdb744508e0514350ce69833 | COc1cc(OC)c(C=O)cc1Br.OB(O)c1cncnc1>>COc1cc(OC)c(-c2cncnc2)cc1C=O | BrC=1C(=CC(=C(C=O)C1)OC)OC.N1=CN=CC(=C1)B(O)O>>COC1=C(C=O)C=C(C(=C1)OC)C=1C=NC=NC1 | Br[c:8]1[c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[c:16]([CH:17]=[O:18])[cH:15]1.OB(O)[c:9]1[cH:10][n:11][cH:12][n:13][cH:14]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][n:11][cH:12][n:13][cH:14]2)[cH:15][c:16]1[CH:17]=[O:18] | COc1cc(OC)c(C=O)cc1Br.OB(O)c1cncnc1 | COc1cc(OC)c(-c2cncnc2)cc1C=O | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 5efc69cb0f56c6c241a71b9df28c03b094ed8fc2f31567997f12f88c03083478 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cncnc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4]=[O;D1;H0:5]):[c:6](-[#8:7]):[c:8].O-B(-O)-[c;H0;D3;+0:9]1:[c:10]:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]:1>>[#8:7]-[c:6](:[c:8]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9]1:[c:10]:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]:1):[c:2]:[c:3]-[C:4]=[O;D1;H0:5] | 98 | [{"value": 98.0, "product": "COC1=C(C=O)C=C(C(=C1)OC)C=1C=NC=NC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Ex-31A: 2,4-Dimethoxy-5-pyrimidin-5-yl-benzaldehyde was prepared from 5-bromo-2,4-dimethoxybenzaldehyde and pyrimidine-5-boronic acid in a similar manner as described in Ex-3A, 98% yield. 1H-NMR (CDCl3) δ 10.37 (s, 1H), 9.15 (s, 1H), 8.87 (s, 2H) 7.86 (s, 1H), 6.57 (s, 1H), 4.03 (s, 3H), 3.96 (s, 3H).
Conditions: See r... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1cncnc1 | c1ccccc1.c1cncnc1 | c1ccccc1.c1cncnc1 | HBr.B | null | null | null | COc1cc(OC)c(C=O)cc1Br.OB(O)c1cncnc1>>COc1cc(OC)c(-c2cncnc2)cc1C=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9c3dc3b392cd4438ba117a73b6f01262 | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2cncnc2)cc1C=O>>COc1cc(OC)c(-c2cncnc2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | COC1=C(C=O)C=C(C(=C1)OC)C=1C=NC=NC1.C(C)(=O)C1=CC=C(C(=O)O)C=C1>>COC1=C(C=C(C(=C1)OC)C=1C=NC=NC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1 | [CH3:18][C:19](=[O:20])[c:21]1[cH:22][cH:23][c:24]([C:25](=[O:26])[OH:27])[cH:28][cH:29]1.O=[CH:17][c:16]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][n:11][cH:12][n:13][cH:14]2)[cH:15]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][n:11][cH:12][n:13][cH:14]2)[cH:15][c:16]1/[CH:17... | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2cncnc2)cc1C=O | COc1cc(OC)c(-c2cncnc2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cncnc2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 26 | [{"value": 26.0, "product": "COC1=C(C=C(C(=C1)OC)C=1C=NC=NC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 2,4-dimethoxy-5-pyrimidin-5-yl-benzaldehyde (Ex-31A) and 4-acetylbezoic acid in a similar manner as described in Ex-3. Yellow solid, mp>260° C., 26% yield. 1H-NMR (DMSO-d6) δ 9.11 (s, 1H), 8.96 (s, 2H), 8.13–8.16 (m, 3H), 8.01–8.09 (m, 3H), 7.90 (d, J=15 Hz, 1H), 6.85 (s, 1... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1cncnc1.c1ccccc1 | HO- | null | null | null | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2cncnc2)cc1C=O>>COc1cc(OC)c(-c2cncnc2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2599c5c31bb8412fa660fff33be023f4 | COc1cc(O)c(C=O)cc1-c1cccs1.ClCC1CC1>>COc1cc(OCC2CC2)c(C=O)cc1-c1cccs1 | OC1=C(C=O)C=C(C(=C1)OC)C=1SC=CC1.ClCC1CC1>>C1(CC1)COC1=C(C=O)C=C(C(=C1)OC)C=1SC=CC1 | [CH3:1][O:2][c:3]1[cH:4][c:5]([OH:6])[c:11]([CH:12]=[O:13])[cH:14][c:15]1-[c:16]1[cH:17][cH:18][cH:19][s:20]1.Cl[CH2:7][CH:8]1[CH2:9][CH2:10]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH2:7][CH:8]2[CH2:9][CH2:10]2)[c:11]([CH:12]=[O:13])[cH:14][c:15]1-[c:16]1[cH:17][cH:18][cH:19][s:20]1 | COc1cc(O)c(C=O)cc1-c1cccs1.ClCC1CC1 | COc1cc(OCC2CC2)c(C=O)cc1-c1cccs1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1csc(-c2ccc(OCC3CC3)cc2)c1 | Cl-[CH2;D2;+0:1]-[C:2]1-[C:3]-[C:4]-1.[O;D1;H0:5]=[C:6]-[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[O;D1;H0:5]=[C:6]-[c:7]:[c:8](-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[C:2]1-[C:3]-[C:4]-1):[c:10] | 18 | [{"value": 18.0, "product": "C1(CC1)COC1=C(C=O)C=C(C(=C1)OC)C=1SC=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Ex-32A: 2-Cyclopropylmethoxy-4-methoxy-5-thiophen-2-yl-benzaldehyde was prepared in a similar manner as described in Ex-29C from 2-hydroxy-4-methoxy-5-thiophen-2-yl-benzaldehyde (Ex. 29B) and chloromethyl-cyclopropane, 18% yield. 1H-NMR (CDCl3) δ 10.41 (s, 1H), 8.24 (s, 1H), 7.43 (d, 1H), 7.29 (d, 1H), 7.06 (t, 1H), 6.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.C1CC1.c1ccsc1 | HCl | null | null | null | COc1cc(O)c(C=O)cc1-c1cccs1.ClCC1CC1>>COc1cc(OCC2CC2)c(C=O)cc1-c1cccs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b93dc0ceba4e440a99747de054e06a40 | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OCC2CC2)c(C=O)cc1-c1cccs1>>COc1cc(OCC2CC2)c(/C=C/C(=O)c2ccc(C(=O)O)cc2)cc1-c1cccs1 | C1(CC1)COC1=C(C=O)C=C(C(=C1)OC)C=1SC=CC1.C(C)(=O)C1=CC=C(C(=O)O)C=C1>>C1(CC1)COC1=C(C=C(C(=C1)OC)C=1SC=CC1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1 | [CH3:13][C:14](=[O:15])[c:16]1[cH:17][cH:18][c:19]([C:20](=[O:21])[OH:22])[cH:23][cH:24]1.O=[CH:12][c:11]1[c:5]([O:6][CH2:7][CH:8]2[CH2:9][CH2:10]2)[cH:4][c:3]([O:2][CH3:1])[c:26](-[c:27]2[cH:28][cH:29][cH:30][s:31]2)[cH:25]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH2:7][CH:8]2[CH2:9][CH2:10]2)[c:11](/[CH:12]=[CH:13]/[C:... | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OCC2CC2)c(C=O)cc1-c1cccs1 | COc1cc(OCC2CC2)c(/C=C/C(=O)c2ccc(C(=O)O)cc2)cc1-c1cccs1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cc(-c2cccs2)ccc1OCC1CC1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The title compound was prepared by condensing 2-cyclopropylmethoxy-4-methoxy-5-thiophen-2-yl-benzaldehyde (Ex-32B) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Yellow solid, mp 187–191° C. 1H-NMR (DMSO-d6) δ 8.22 (d, 2H), 8.19 (s, 1H), 7.01 (m, 4H), 7.62 (d, 1H), 7.47 (d, 1H), 7.09 (t, 1H), 6.76 (... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.C1CC1.c1ccccc1.c1ccsc1 | HO- | null | null | null | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OCC2CC2)c(C=O)cc1-c1cccs1>>COc1cc(OCC2CC2)c(/C=C/C(=O)c2ccc(C(=O)O)cc2)cc1-c1cccs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cae727d29c5142bab06a1ae4493a7906 | COc1cc(OC)c(C=O)cc1Br.Cc1noc(C)c1B(O)O>>COc1cc(OC)c(-c2c(C)noc2C)cc1C=O | BrC=1C(=CC(=C(C=O)C1)OC)OC.CC1=NOC(=C1B(O)O)C>>CC1=NOC(=C1C=1C(=CC(=C(C=O)C1)OC)OC)C | Br[c:8]1[c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[c:17]([CH:18]=[O:19])[cH:16]1.OB(O)[c:9]1[c:10]([CH3:11])[n:12][o:13][c:14]1[CH3:15]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[c:10]([CH3:11])[n:12][o:13][c:14]2[CH3:15])[cH:16][c:17]1[CH:18]=[O:19] | COc1cc(OC)c(C=O)cc1Br.Cc1noc(C)c1B(O)O | COc1cc(OC)c(-c2c(C)noc2C)cc1C=O | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 5b7dd82949a962746098cf241492f164306faeffdc0ae0e0292301e001a6c22c | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cnoc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4]=[O;D1;H0:5]):[c:6](-[#8:7]):[c:8].O-B(-O)-[c;H0;D3;+0:9]1:[c:10](-[C;D1;H3:11]):[#7;a:12]:[#8;a:13]:[c:14]:1-[C;D1;H3:15]>>[#8:7]-[c:6](:[c:8]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9]1:[c:10](-[C;D1;H3:11]):[#7;a:12]:[#8;a:13]:[c:14]:1-[C;D1;H3:15]):[c:2]:[c:3]-[C:4]=[O;D1;H0:5] | 75 | [{"value": 75.0, "product": "CC1=NOC(=C1C=1C(=CC(=C(C=O)C1)OC)OC)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Ex-33A: 5-(3,5-Dimethyl-isoxazol-4-yl)-2,4-dimethoxy-benzaldehyde was prepared from 5-bromo-2,4-dimethoxybenzaldehyde and 3,5-dimethyl-isoxazole-4-boronic acid in a similar manner as described in Ex-3A, 75% yield. 1H-NMR (CDCl3) δ 10.34 (s, 1H), 7.63 (s, 1H), 6.52 (s, 1H), 4.00 (s, 3H), 3.90 (s, 3H), 2.12 (s, 6H).
Cond... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1cnoc1 | c1ccccc1.c1cnoc1 | c1ccccc1.c1cnoc1 | HBr.B | null | null | null | COc1cc(OC)c(C=O)cc1Br.Cc1noc(C)c1B(O)O>>COc1cc(OC)c(-c2c(C)noc2C)cc1C=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bf5538abf09f4116b115afb71cb81295 | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2c(C)noc2C)cc1C=O>>COc1cc(OC)c(-c2c(C)noc2C)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | CC1=NOC(=C1C=1C(=CC(=C(C=O)C1)OC)OC)C.C(C)(=O)C1=CC=C(C(=O)O)C=C1>>CC1=NOC(=C1C=1C(=CC(=C(C1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)OC)OC)C | [CH3:19][C:20](=[O:21])[c:22]1[cH:23][cH:24][c:25]([C:26](=[O:27])[OH:28])[cH:29][cH:30]1.O=[CH:18][c:17]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[c:10]([CH3:11])[n:12][o:13][c:14]2[CH3:15])[cH:16]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[c:10]([CH3:11])[n:12][o:13][c:14]2[CH3:15])[cH... | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2c(C)noc2C)cc1C=O | COc1cc(OC)c(-c2c(C)noc2C)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cnoc2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 7 | [{"value": 7.0, "product": "CC1=NOC(=C1C=1C(=CC(=C(C1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)OC)OC)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 5-(3,5-dimethyl-isoxazol-4-yl)-2,4-dimethoxy-benzaldehyde (Ex-33A) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Yellow solid, mp>260° C., 7% yield. 1H-NMR (DMSO-d6) δ 8.15 (d, J=8 Hz, 2H), 8.04 (d, J=16 Hz, 1H), 8.02 (d, J=8 Hz, 2H), 7.89 (s, 1H), 7.81... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1cnoc1.c1ccccc1 | HO- | null | null | null | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2c(C)noc2C)cc1C=O>>COc1cc(OC)c(-c2c(C)noc2C)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8369248867f0408eb05df10e2fc0ea3b | COc1ccc(C=O)c(OS(=O)(=O)C(F)(F)F)c1.OB(O)c1cccs1>>COc1ccc(C=O)c(-c2cccs2)c1 | S1C(=CC=C1)B(O)O.P(=O)([O-])([O-])[O-].[K+].[K+].[K+].C(=O)C1=C(C=C(C=C1)OC)OS(=O)(=O)C(F)(F)F>>COC1=CC(=C(C=O)C=C1)C=1SC=CC1 | O=S(=O)(O[c:9]1[c:6]([CH:7]=[O:8])[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:15]1)C(F)(F)F.OB(O)[c:10]1[cH:11][cH:12][cH:13][s:14]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[O:8])[c:9](-[c:10]2[cH:11][cH:12][cH:13][s:14]2)[cH:15]1 | COc1ccc(C=O)c(OS(=O)(=O)C(F)(F)F)c1.OB(O)c1cccs1 | COc1ccc(C=O)c(-c2cccs2)c1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | CCOC(=O)C.O.O1CCOCC1 | C-C Coupling | Suzuki coupling with boronic acids OTf | c69a6f6be1d8ce542404db514bc9846ba00a86118103061e95d9f239037a465f | 3f602cf53fbcf2a56d992979503f6bea55727095a6b9075475a711784170b440 | c1ccc(-c2cccs2)cc1 | F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]=[O;D1;H0:6]):[c:7].O-B(-O)-[c;H0;D3;+0:8]1:[#16;a:9]:[c:10]:[c:11]:[c:12]:1>>[O;D1;H0:6]=[C:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[c;H0;D3;+0:8]1:[#16;a:9]:[c:10]:[c:11]:[c:12]:1):[c:2]:[c:3] | 90 | [{"value": 90.0, "product": "COC1=CC(=C(C=O)C=C1)C=1SC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.5, "product": "COC1=CC(=C(C=O)C=C1)C=1SC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | null | null | Ex-34B: A solution of trifluoro-methanesulfonic acid 2-formyl-5-methoxy-phenyl ester (Ex-34A, 1.6 g, 5.63 mmol) in 1,4-dioxane (15 mL) was stirred at room temperature under nitrogen for 5 min. Thiophene-2-boronic acid (1.08 g, 8.44 mmol), tetrakis(triphenylphosphine)palladium(0) (0.65 g, 0.56 mmol) and a potassium phos... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Boronic acid | null | c1ccccc1.c1ccsc1 | c1ccccc1.c1ccsc1 | c1ccccc1.c1ccsc1 | TfOH.HO-.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.CCOC(=O)C.O.O1CCOCC1 | 95 | null | COc1ccc(C=O)c(OS(=O)(=O)C(F)(F)F)c1.OB(O)c1cccs1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.CCOC(=O)C.O.O1CCOCC1>COc1ccc(C=O)c(-c2cccs2)c1 |
Subsets and Splits
No community queries yet
The top public SQL queries from the community will appear here once available.