dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ede011a0f2824c2d9586f37aeb9e12dc | CC(O)Cc1cccc(CO[Si](C)(C)C(C)(C)C)c1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>>CC(Cc1cccc(CO[Si](C)(C)C(C)(C)C)c1)N=[N+]=[N-] | [Si](C)(C)(C(C)(C)C)OCC=1C=C(C=CC1)CC(C)O.N(=NC(=O)OC(C)C)C(=O)OC(C)C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)N=[N+]=[N-]>>N(=[N+]=[N-])C(CC=1C=C(CO[Si](C)(C)C(C)(C)C)C=CC1)C | O[CH:2]([CH3:1])[CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([CH2:9][O:10][Si:11]([CH3:12])([CH3:13])[C:14]([CH3:15])([CH3:16])[CH3:17])[cH:18]1.O=P(c1ccccc1)(c1ccccc1)[N:19]=[N+:20]=[N-:21]>>[CH3:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([CH2:9][O:10][Si:11]([CH3:12])([CH3:13])[C:14]([CH3:15])([CH3:16])[CH3:17])[cH:18]1)[... | CC(O)Cc1cccc(CO[Si](C)(C)C(C)(C)C)c1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1 | CC(Cc1cccc(CO[Si](C)(C)C(C)(C)C)c1)N=[N+]=[N-] | null | null | ClCCl.C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 7ddeb0863eb9d18ad2b86c965fac8ce00b768f5efc2d375573a09ce2ec7becb3 | b7a1a21645e453100c6e96f234a0b9438c4e233c7e52a9b671803a56cb864130 | c1ccccc1 | O-[CH;D3;+0:1](-[C;D1;H3:2])-[C:3]-[c:4].O=P(-[N;H0;D2;+0:5]=[#7;+:6]=[N;-;D1;H0:7])(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C;D1;H3:2]-[CH;D3;+0:1](-[C:3]-[c:4])-[N;H0;D2;+0:5]=[#7;+:6]=[N;-;D1;H0:7] | null | [] | 0 | CELSIUS | 15 | MINUTE | To a stirring solution of 1-[3-(tert-butyldimethylsilyloxymethyl)-phenyl]-propan-2-ol (130 mg, 0.46 mmol) in THF (1.5 mL) under nitrogen at 0° C. was added diisopropyl azodicarboxylate (140 mg, 0.7 mmol), triphenylphosphine (180 mg, 0.7 mmol), and diphenylphosphoryl azide (190 mg, 0.7 mmol) and the mixture was stirred ... | 10.6084/m9.figshare.5104873.v1 | null | Azide.Secondary alcohol | Azide | c1ccccc1.c1ccccc1 | null | c1ccccc1 | HO- | ClCCl.C1CCOC1 | 0 | 0.25 | CC(O)Cc1cccc(CO[Si](C)(C)C(C)(C)C)c1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>ClCCl.C1CCOC1>CC(Cc1cccc(CO[Si](C)(C)C(C)(C)C)c1)N=[N+]=[N-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c4a63c857a0149238c90e001ea0ed467 | CCOC(=O)CCC1CN(c2ccnc(NCCc3ccccc3)n2)c2nc(-c3ccccc3)cc(=O)n2C1>>O=C(O)CCC1CN(c2ccnc(NCCc3ccccc3)n2)c2nc(-c3ccccc3)cc(=O)n2C1 | C(C)OC(CCC1CN(C=2N(C1)C(C=C(N2)C2=CC=CC=C2)=O)C2=NC(=NC=C2)NCCC2=CC=CC=C2)=O.[OH-].[Li+]>>O=C1C=C(N=C2N1CC(CN2C2=NC(=NC=C2)NCCC2=CC=CC=C2)CCC(=O)O)C2=CC=CC=C2 | CC[O:3][C:2](=[O:1])[CH2:4][CH2:5][CH:6]1[CH2:7][N:8]([c:9]2[cH:10][cH:11][n:12][c:13]([NH:14][CH2:15][CH2:16][c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[n:23]2)[c:24]2[n:25][c:26](-[c:27]3[cH:28][cH:29][cH:30][cH:31][cH:32]3)[cH:33][c:34](=[O:35])[n:36]2[CH2:37]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH:6]1[CH2:7][N:8](... | CCOC(=O)CCC1CN(c2ccnc(NCCc3ccccc3)n2)c2nc(-c3ccccc3)cc(=O)n2C1 | O=C(O)CCC1CN(c2ccnc(NCCc3ccccc3)n2)c2nc(-c3ccccc3)cc(=O)n2C1 | null | null | O1CCCC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1cc(-c2ccccc2)nc2n1CCCN2c1ccnc(NCCc2ccccc2)n1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | null | null | A solution of 3-[6-oxo-1-(2-phenethylamino-pyrimidin-4-yl)-8-phenyl-1,3,4,6-tetrahydro-2H-pyrimido[1,2-a]pyrimidin-3-yl]-propionic acid ethyl ester (240 mg, 0.46 mmol), 10% aqueous lithium hydroxide (0.2 mL), and tetrahydrofuran (5 mL) was heated to 50° C. Reaction partitioned between dichloromethane (50 mL) and 5% sod... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cncnc1.c1ccccc1.c1ccn2c(n1)NC[CH]C2.c1ccccc1 | Other | O1CCCC1 | null | null | CCOC(=O)CCC1CN(c2ccnc(NCCc3ccccc3)n2)c2nc(-c3ccccc3)cc(=O)n2C1>O1CCCC1>O=C(O)CCC1CN(c2ccnc(NCCc3ccccc3)n2)c2nc(-c3ccccc3)cc(=O)n2C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d242b8ffa3834548bc2828bbe0993657 | O=C(NCCC1CN(c2ccnc(NCCc3ccccc3)n2)c2nc(-c3ccccc3)cc(=O)n2C1)OCc1ccccc1>>NCCC1CN(c2ccnc(NCCc3ccccc3)n2)c2nc(-c3ccccc3)cc(=O)n2C1 | C(C1=CC=CC=C1)OC(NCCC1CN(C=2N(C1)C(C=C(N2)C2=CC=CC=C2)=O)C2=NC(=NC=C2)NCCC2=CC=CC=C2)=O.ClCCl.[H][H]>>NCCC1CN(C=2N(C(C=C(N2)C2=CC=CC=C2)=O)C1)C1=NC(=NC=C1)NCCC1=CC=CC=C1 | O=C(OCc1ccccc1)[NH:1][CH2:2][CH2:3][CH:4]1[CH2:5][N:6]([c:7]2[cH:8][cH:9][n:10][c:11]([NH:12][CH2:13][CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[n:21]2)[c:22]2[n:23][c:24](-[c:25]3[cH:26][cH:27][cH:28][cH:29][cH:30]3)[cH:31][c:32](=[O:33])[n:34]2[CH2:35]1>>[NH2:1][CH2:2][CH2:3][CH:4]1[CH2:5][N:6]([c:7]2[cH:8][... | O=C(NCCC1CN(c2ccnc(NCCc3ccccc3)n2)c2nc(-c3ccccc3)cc(=O)n2C1)OCc1ccccc1 | NCCC1CN(c2ccnc(NCCc3ccccc3)n2)c2nc(-c3ccccc3)cc(=O)n2C1 | null | [Pd] | CO | Reduction | Hydrogenolysis of amides/imides/carbamates | 087b6600ba91d3df931fe6979f2445c192cbfd59e04fd2d8a10f7c7573ac669f | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | O=c1cc(-c2ccccc2)nc2n1CCCN2c1ccnc(NCCc2ccccc2)n1 | O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | null | null | A solution of {2-[6-Oxo-1-(2-phenethylamino-pyrimidin-4-yl)-8-phenyl-1,3,4,6-tetrahydro-2H-pyrimido[1,2-a]pyrimidin-3-yl]-ethyl}-carbamic acid benzyl ester (100 mg, 0.17 mmol), dichloromethane (5 mL) and methanol (15 mL) was added 10% palladium on carbon (5 mg) and stirred at room temperature over an atmosphere of hydr... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | c1ccccc1 | null | c1cncnc1.c1ccccc1.c1ccn2c(n1)NC[CH]C2.c1ccccc1 | HO- | [Pd].CO | null | null | O=C(NCCC1CN(c2ccnc(NCCc3ccccc3)n2)c2nc(-c3ccccc3)cc(=O)n2C1)OCc1ccccc1>[Pd].CO>NCCC1CN(c2ccnc(NCCc3ccccc3)n2)c2nc(-c3ccccc3)cc(=O)n2C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-13259bf123d54673ac4b4e67de5cd963 | CC(C)=O.NCCC1CN(c2ccnc(NCCc3ccccc3)n2)c2nc(-c3ccccc3)cc(=O)n2C1>>CC(C)NCCC1CN(c2ccnc(NCCc3ccccc3)n2)c2nc(-c3ccccc3)cc(=O)n2C1 | C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+].NCCC1CN(C=2N(C(C=C(N2)C2=CC=CC=C2)=O)C1)C1=NC(=NC=C1)NCCC1=CC=CC=C1.CC(=O)C.ClCCl>>C(C)(C)NCCC1CN(C=2N(C(C=C(N2)C2=CC=CC=C2)=O)C1)C1=NC(=NC=C1)NCCC1=CC=CC=C1 | O=[C:2]([CH3:1])[CH3:3].[NH2:4][CH2:5][CH2:6][CH:7]1[CH2:8][N:9]([c:10]2[cH:11][cH:12][n:13][c:14]([NH:15][CH2:16][CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[n:24]2)[c:25]2[n:26][c:27](-[c:28]3[cH:29][cH:30][cH:31][cH:32][cH:33]3)[cH:34][c:35](=[O:36])[n:37]2[CH2:38]1>>[CH3:1][CH:2]([CH3:3])[NH:4][CH2:5][CH2:6... | CC(C)=O.NCCC1CN(c2ccnc(NCCc3ccccc3)n2)c2nc(-c3ccccc3)cc(=O)n2C1 | CC(C)NCCC1CN(c2ccnc(NCCc3ccccc3)n2)c2nc(-c3ccccc3)cc(=O)n2C1 | null | null | CO | Heteroatom Alkylation and Arylation | Reductive amination with ketone | 4940e8ed9a0db9bde699fdcdc3aff2cff0409c19478aa0ed1acfd98213338adf | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | O=c1cc(-c2ccccc2)nc2n1CCCN2c1ccnc(NCCc2ccccc2)n1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[C:4]-[C:5]-[NH;D2;+0:6]-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3] | null | [] | null | null | 2 | HOUR | To a solution of 7-(2-Amino-ethyl)-9-(2-phenethylamino-pyrimidin-4-yl)-2-phenyl-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one (70 mg, 0.15 mmol), acetone (0.02 mL), dichloromethane (0.5 mL) and methanol (0.5 mL) was added sodium triacetoxyborohydride (38 mg, 0.18 mmol) Reaction stirred for 2 h at room temperature. ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | null | null | c1cncnc1.c1ccccc1.c1ccn2c(n1)NC[CH]C2.c1ccccc1 | Other | CO | null | 2 | CC(C)=O.NCCC1CN(c2ccnc(NCCc3ccccc3)n2)c2nc(-c3ccccc3)cc(=O)n2C1>CO>CC(C)NCCC1CN(c2ccnc(NCCc3ccccc3)n2)c2nc(-c3ccccc3)cc(=O)n2C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-39cb08f716ea46fc9d7265a15ce12e7a | CI.Nc1nc(-c2ccccc2)cc(=O)[nH]1>>Cn1c(N)nc(-c2ccccc2)cc1=O | CI.[OH-].[K+].CI.NC1=NC(=CC(N1)=O)C1=CC=CC=C1>>NC1=NC(=CC(N1C)=O)C1=CC=CC=C1 | I[CH3:1].[nH:2]1[c:3]([NH2:4])[n:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:13][c:14]1=[O:15]>>[CH3:1][n:2]1[c:3]([NH2:4])[n:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:13][c:14]1=[O:15] | CI.Nc1nc(-c2ccccc2)cc(=O)[nH]1 | Cn1c(N)nc(-c2ccccc2)cc1=O | null | null | CCO | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 8b8b604c36c54bca847ea1bd1b7840d48f065047e5c951a27f860631728323c9 | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | O=c1cc(-c2ccccc2)nc[nH]1 | I-[CH3;D1;+0:1].[N;D1;H2:2]-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[c:7](=[O;D1;H0:8]):[nH;D2;+0:9]:1>>[CH3;D1;+0:1]-[n;H0;D3;+0:9]1:[c:7](=[O;D1;H0:8]):[c:6]:[c:5]:[#7;a:4]:[c:3]:1-[N;D1;H2:2] | null | [] | null | null | 3 | DAY | A mixture of KOH (1.22 g, 22 mmol), MeI (6.85 g, 48 mmol), and 2-amino-6-phenyl-3H-pyrimidin-4-one (2.62 g, 14 mmol) in EtOH (130 mL) was stirred at room temperature in a stoppered 250 mL roundbottom flask for 3 days. An additional 6.85 g (48 mmol) MeI was added and stirring was continued for 1 day. The solvent was rem... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccncn1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HI | CCO | null | 72 | CI.Nc1nc(-c2ccccc2)cc(=O)[nH]1>CCO>Cn1c(N)nc(-c2ccccc2)cc1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c36ac95a2c8f4a28bbcb4b4b9223578e | CC(N)Cc1cccc(CO)c1.Cn1c(Nc2ccnc(S(C)=O)n2)nc(-c2ccccc2)cc1=O>>CC(Cc1cccc(CO)c1)Nc1nccc(Nc2nc(-c3ccccc3)cc(=O)n2C)n1 | NC(CC=1C=C(C=CC1)CO)C.CS(=O)C1=NC=CC(=N1)NC1=NC(=CC(N1C)=O)C1=CC=CC=C1.CCOC(=O)C>>OCC=1C=C(C=CC1)CC(C)NC1=NC=CC(=N1)NC1=NC(=CC(N1C)=O)C1=CC=CC=C1 | [CH3:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([CH2:9][OH:10])[cH:11]1)[NH2:12].CS(=O)[c:13]1[n:14][cH:15][cH:16][c:17]([NH:18][c:19]2[n:20][c:21](-[c:22]3[cH:23][cH:24][cH:25][cH:26][cH:27]3)[cH:28][c:29](=[O:30])[n:31]2[CH3:32])[n:33]1>>[CH3:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([CH2:9][OH:10])[cH:11]1)[N... | CC(N)Cc1cccc(CO)c1.Cn1c(Nc2ccnc(S(C)=O)n2)nc(-c2ccccc2)cc1=O | CC(Cc1cccc(CO)c1)Nc1nccc(Nc2nc(-c3ccccc3)cc(=O)n2C)n1 | null | null | CN1CCCC1=O | Heteroatom Alkylation and Arylation | OtherReaction | ac54b6a0f3a60d8937c1d499ecd10bb03cfe7d9c83e017605df8cdfb870cd022 | 5d96541e7662f23805fb9b1f27c86ee9e32f55f6d2b692c46751dd2fe7aa65a5 | O=c1cc(-c2ccccc2)nc(Nc2ccnc(NCCc3ccccc3)n2)[nH]1 | C-S(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7](-[C;D1;H3:8])-[NH2;D1;+0:9]>>[C:6]-[C:7](-[C;D1;H3:8])-[NH;D2;+0:9]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | null | [] | 100 | CELSIUS | null | null | A mixture of [3-(2-amino-propyl) -phenyl]-methanol (300 mg, 1.8 mmol) and 2-(2-methanesulfinyl-pyrimidin-4-ylamino) -3-methyl-6-phenyl-3H-pyrimidin-4-one (300 mg, 0.9 mmol) in NMP (8 mL) was heated to 100° C. for 16 h. The reaction was cooled to room temperature and EtOAc was added. The mixture was then washed with H2O... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfoxide | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1cncnc1.c1ccccc1 | Other | CN1CCCC1=O | 100 | null | CC(N)Cc1cccc(CO)c1.Cn1c(Nc2ccnc(S(C)=O)n2)nc(-c2ccccc2)cc1=O>CN1CCCC1=O>CC(Cc1cccc(CO)c1)Nc1nccc(Nc2nc(-c3ccccc3)cc(=O)n2C)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3548fe0a340042d59fd4d020a5eaab90 | C=CC(=O)OCC.CC(NC(=O)OC(C)(C)C)c1ccc(Br)cc1>>CCOC(=O)C=Cc1ccc(C(C)NC(=O)OC(C)(C)C)cc1 | C(C=C)(=O)OCC.C(C)(C)(C)P(C(C)(C)C)C(C)(C)C.C(C)(C)(C)OC(NC(C)C1=CC=C(C=C1)Br)=O.CN(C1CCCCC1)C1CCCCC1>>C(C)OC(C=CC1=CC=C(C=C1)C(C)NC(=O)OC(C)(C)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[CH2:7].Br[c:8]1[cH:9][cH:10][c:11]([CH:12]([CH3:13])[NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[cH:22][cH:23]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[CH:7][c:8]1[cH:9][cH:10][c:11]([CH:12]([CH3:13])[NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:2... | C=CC(=O)OCC.CC(NC(=O)OC(C)(C)C)c1ccc(Br)cc1 | CCOC(=O)C=Cc1ccc(C(C)NC(=O)OC(C)(C)C)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] | O1CCOCC1.O | C-C Coupling | Heck terminal vinyl | 55becfded1a3842d5a03bbf3e1610411c659aff0806930400c4db2ef61f9c87f | 4b186811a4930853b446d93d9faa39b267bddb9ce0b8021bda5c5a3b2bc69f0b | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C:10]=[CH2;D1;+0:11]>>[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C:10]=[CH;D2;+0:11]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | 80 | CELSIUS | null | null | To a mixture of [1-(4-bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester (3.0 g, 10 mmol), tris(dibenzylideneacetone)dipalladium (0.55 g, 0.6 mmol), and N -methyldicyclohexylamine (2.1 mL, 10 mmol) was purged nitrogen followed by the addition of 1,4-dioxane (20 mL) and tri-tert-butylphospine (0.24 g, 1.2 mmol). The mi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Vinyl | null | c1ccccc1 | c1ccccc1 | 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].O1CCOCC1.O | 80 | null | C=CC(=O)OCC.CC(NC(=O)OC(C)(C)C)c1ccc(Br)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].O1CCOCC1.O>CCOC(=O)C=Cc1ccc(C(C)NC(=O)OC(C)(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-03202a9215ad4d28aa44793bae1ae8ea | CCOC(=O)C=Cc1ccc(C(C)NC(=O)OC(C)(C)C)cc1>>CCOC(=O)CCc1ccc(C(C)NC(=O)OC(C)(C)C)cc1 | C(C)OC(C=CC1=CC=C(C=C1)C(C)NC(=O)OC(C)(C)C)=O>>C(C)OC(CCC1=CC=C(C=C1)C(C)NC(=O)OC(C)(C)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[CH:7][c:8]1[cH:9][cH:10][c:11]([CH:12]([CH3:13])[NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[cH:22][cH:23]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]([CH:12]([CH3:13])[NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])... | CCOC(=O)C=Cc1ccc(C(C)NC(=O)OC(C)(C)C)cc1 | CCOC(=O)CCc1ccc(C(C)NC(=O)OC(C)(C)C)cc1 | null | [OH-].[OH-].[Pd+2] | C(C)O | Reduction | Hydrogenation (double to single) | c04c38f95d7b746e5bdb99c368a7a33956c97b95b54c7ad89be2a85526386ec9 | 9a50abf8d2e4cd9195d7a0cadbe97483a261a81cf70b653cfddd5ecf76d383a6 | c1ccccc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D2;+0:5]=[CH;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9] | null | [] | null | null | null | null | Through a mixture of 3-[4-(1-tert-butoxycarbonylamino-ethyl)-phenyl]-acrylic acid ethyl ester (0.22 g, 0.69 mmol) and palladium hydroxide on carbon (100 mg) in ethanol (10 mL) was bubbled hydrogen through a balloon for 17 h. The mixture was filtered through celite and concentrated to afford an off-white solid. M+1=322.... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | null | null | c1ccccc1 | null | [OH-].[OH-].[Pd+2].C(C)O | null | null | CCOC(=O)C=Cc1ccc(C(C)NC(=O)OC(C)(C)C)cc1>[OH-].[OH-].[Pd+2].C(C)O>CCOC(=O)CCc1ccc(C(C)NC(=O)OC(C)(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1aecb3e8b14b42bcb46ebaf03ae1008f | CC(NC(=O)OC(C)(C)C)c1ccc(CCNC(=O)OCc2ccccc2)cc1>>CC(NC(=O)OC(C)(C)C)c1ccc(CCN)cc1 | C(C)(C)(C)OC(NC(C)C1=CC=C(C=C1)CCNC(=O)OCC1=CC=CC=C1)=O.C1=CCC=CC1.CO>>C(C)(C)(C)OC(NC(C)C1=CC=C(C=C1)CCN)=O | O=C(OCc1ccccc1)[NH:17][CH2:16][CH2:15][c:14]1[cH:13][cH:12][c:11]([CH:2]([CH3:1])[NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[cH:19][cH:18]1>>[CH3:1][CH:2]([NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[c:11]1[cH:12][cH:13][c:14]([CH2:15][CH2:16][NH2:17])[cH:18][cH:19]1 | CC(NC(=O)OC(C)(C)C)c1ccc(CCNC(=O)OCc2ccccc2)cc1 | CC(NC(=O)OC(C)(C)C)c1ccc(CCN)cc1 | null | [Pd] | C(C)O | Reduction | Hydrogenolysis of amides/imides/carbamates | 087b6600ba91d3df931fe6979f2445c192cbfd59e04fd2d8a10f7c7573ac669f | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | c1ccccc1 | O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | null | null | The mixture of {1-[4-(2-benzyloxycarbonylamino-ethyl)-phenyl]-ethyl}carbamic acid tert-butyl ester (0.80 g, 2.0 mmol), 1,4-cyclohexadiene (0.96 mL, 10 mmol) and palladium on carbon (100 mg) in ethanol (20 mL)-methanol (5 mL) was heated to reflux for 2 h and brought to room temperature. The mixture was filtered through ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | c1ccccc1 | null | c1ccccc1 | HO- | [Pd].C(C)O | null | null | CC(NC(=O)OC(C)(C)C)c1ccc(CCNC(=O)OCc2ccccc2)cc1>[Pd].C(C)O>CC(NC(=O)OC(C)(C)C)c1ccc(CCN)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-da297c3cf29b4412bf3fcc93f12a5406 | CC(NC(=O)OC(C)(C)C)c1ccc(CCN)cc1.CS(=O)(=O)c1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1>>CC(NC(=O)OC(C)(C)C)c1ccc(CCNc2nccc(N3CCC(=O)N4CC=C(c5ccccc5)N=C43)n2)cc1 | CS(=O)(=O)C1=NC=CC(=N1)N1C=2N(C(CC1)=O)CC=C(N2)C2=CC=CC=C2.C(C)(C)(C)OC(NC(C)C1=CC=C(C=C1)CCN)=O.O1CCOCC1>>C(C)(C)(C)OC(NC(C)C1=CC=C(C=C1)CCNC1=NC=CC(=N1)N1C=2N(C(CC1)=O)CC=C(N2)C2=CC=CC=C2)=O | [CH3:1][CH:2]([NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[c:11]1[cH:12][cH:13][c:14]([CH2:15][CH2:16][NH2:17])[cH:41][cH:42]1.CS(=O)(=O)[c:18]1[n:19][cH:20][cH:21][c:22]([N:23]2[CH2:24][CH2:25][C:26](=[O:27])[N:28]3[CH2:29][CH:30]=[C:31]([c:32]4[cH:33][cH:34][cH:35][cH:36][cH:37]4)[N:38]=[C:39]23)[n:40]1>>... | CC(NC(=O)OC(C)(C)C)c1ccc(CCN)cc1.CS(=O)(=O)c1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1 | CC(NC(=O)OC(C)(C)C)c1ccc(CCNc2nccc(N3CCC(=O)N4CC=C(c5ccccc5)N=C43)n2)cc1 | null | null | CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | OtherReaction | 289adcacbe89f1503fb3c9d1b660927aaeb421d7b5520077738f22dce3010144 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=C1CCN(c2ccnc(NCCc3ccccc3)n2)C2=NC(c3ccccc3)=CCN12 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | The mixture of 1-(2-methanesulfonyl-pyrimidin-4-yl)-8-phenyl-1,2,3,6-tetrahydro -pyrimido[1,2-a]pyrimidin-4-one (0.20 g, 053 mmol) and {1-[4-(2-amino -ethyl)-phenyl]-ethyl}-carbamic acid tert-butyl ester (0.304 g, 0.79 mmol) in 1:1 dioxane: 1-methyl -2-pyrrolidinone (6 mL) was heated to 100° C. for 17 h. The mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.C1=CN=C2[NH]CCCN2C1.c1ccccc1 | HO- | CN1C(CCC1)=O | null | null | CC(NC(=O)OC(C)(C)C)c1ccc(CCN)cc1.CS(=O)(=O)c1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1>CN1C(CCC1)=O>CC(NC(=O)OC(C)(C)C)c1ccc(CCNc2nccc(N3CCC(=O)N4CC=C(c5ccccc5)N=C43)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ef3eca606b604be5a9ee6c58e663f477 | CC(N)Cc1ccc(CO)cc1.CS(=O)(=O)c1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1>>CC(Cc1ccc(CO)cc1)Nc1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1 | CS(=O)(=O)C1=NC=CC(=N1)N1C=2N(C(CC1)=O)CC=C(N2)C2=CC=CC=C2.NC(CC1=CC=C(C=C1)CO)C.O1CCOCC1>>OCC1=CC=C(C=C1)CC(C)NC1=NC=CC(=N1)N1C=2N(C(CC1)=O)CC=C(N2)C2=CC=CC=C2 | [CH3:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][OH:9])[cH:10][cH:11]1)[NH2:12].CS(=O)(=O)[c:13]1[n:14][cH:15][cH:16][c:17]([N:18]2[CH2:19][CH2:20][C:21](=[O:22])[N:23]3[CH2:24][CH:25]=[C:26]([c:27]4[cH:28][cH:29][cH:30][cH:31][cH:32]4)[N:33]=[C:34]23)[n:35]1>>[CH3:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][OH... | CC(N)Cc1ccc(CO)cc1.CS(=O)(=O)c1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1 | CC(Cc1ccc(CO)cc1)Nc1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1 | null | null | CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | OtherReaction | 289adcacbe89f1503fb3c9d1b660927aaeb421d7b5520077738f22dce3010144 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=C1CCN(c2ccnc(NCCc3ccccc3)n2)C2=NC(c3ccccc3)=CCN12 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7](-[C;D1;H3:8])-[NH2;D1;+0:9]>>[C:6]-[C:7](-[C;D1;H3:8])-[NH;D2;+0:9]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | 1-(2-methanesulfonyl-pyrimidin-4-yl)-8-phenyl-1,2,3,6-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one (1.1 g, 2.9 mmol) and [4-(2-amino-propyl)-phenyl]-methanol (0.96 g, 5.8 mmol) in 1:1 dioxane: 1-methyl-2-pyrrolidinone (16 mL) was heated to 100° C. for 20 h. The mixture was partitioned between water (30 mL) and ethyl aceta... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.C1=CN=C2[NH]CCCN2C1.c1ccccc1 | HO- | CN1C(CCC1)=O | null | null | CC(N)Cc1ccc(CO)cc1.CS(=O)(=O)c1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1>CN1C(CCC1)=O>CC(Cc1ccc(CO)cc1)Nc1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-520a25fcf6cc443b94c8b137ba59102e | CC(Cc1ccc(CO)cc1)Nc1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>>CC(Cc1ccc(CN=[N+]=[N-])cc1)Nc1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1 | OCC1=CC=C(C=C1)CC(C)NC1=NC=CC(=N1)N1C=2N(C(CC1)=O)CC=C(N2)C2=CC=CC=C2.N12CCCCCC2=NCCC1.C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)N=[N+]=[N-]>>N(=[N+]=[N-])CC1=CC=C(C=C1)CC(C)NC1=NC=CC(=N1)N1C=2N(C(CC1)=O)CC=C(N2)C2=CC=CC=C2 | O[CH2:8][c:7]1[cH:6][cH:5][c:4]([CH2:3][CH:2]([CH3:1])[NH:14][c:15]2[n:16][cH:17][cH:18][c:19]([N:20]3[CH2:21][CH2:22][C:23](=[O:24])[N:25]4[CH2:26][CH:27]=[C:28]([c:29]5[cH:30][cH:31][cH:32][cH:33][cH:34]5)[N:35]=[C:36]34)[n:37]2)[cH:13][cH:12]1.O=P(c1ccccc1)(c1ccccc1)[N:9]=[N+:10]=[N-:11]>>[CH3:1][CH:2]([CH2:3][c:4]1... | CC(Cc1ccc(CO)cc1)Nc1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1 | CC(Cc1ccc(CN=[N+]=[N-])cc1)Nc1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | cfa52427fe008248ccb3b060cca934c64c46f29eb11684ddb953f16825bf2f0e | da5ad8c0affa2dc7232b479927687ff59fae3f37df63d467193897a964229798 | O=C1CCN(c2ccnc(NCCc3ccccc3)n2)C2=NC(c3ccccc3)=CCN12 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].O=P(-[N;H0;D2;+0:5]=[#7;+:6]=[N;-;D1;H0:7])(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[N;-;D1;H0:7]=[#7;+:6]=[N;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 17 | HOUR | The mixture of 1-{2-[2-(4-hydroxymethyl-phenyl)-1-methyl-ethylamino]-pyrimidin-4-yl}-8-phenyl-1,2,3,6-tetrahydro -pyrimido[1,2-a]pyrimidin-4-one (0.11 g, 0.24 mmol) and 1,8-diaza-bicyclo[5.4.0]undec-7-ene (47 μL, 0.312 mmol) in tetrahydrofuran (5 mL) was brought to 0° C. followed by the addition of diphenylphosphoryl a... | 10.6084/m9.figshare.5104873.v1 | null | Azide.Primary alcohol | Azide | c1ccccc1.c1ccccc1 | null | c1ccccc1.c1cncnc1.C1=CN=C2[NH]CCCN2C1.c1ccccc1 | HO- | O1CCCC1 | null | 17 | CC(Cc1ccc(CO)cc1)Nc1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>O1CCCC1>CC(Cc1ccc(CN=[N+]=[N-])cc1)Nc1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8ac111c1e0264127af1000863e1571da | CC(Cc1ccc(CN=[N+]=[N-])cc1)Nc1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1>>CC(Cc1ccc(CN)cc1)Nc1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1 | N(=[N+]=[N-])CC1=CC=C(C=C1)CC(C)NC1=NC=CC(=N1)N1C=2N(C(CC1)=O)CC=C(N2)C2=CC=CC=C2.C1=CCC=CC1>>NCC1=CC=C(C=C1)CC(C)NC1=NC=CC(=N1)N1C=2N(C(CC1)=O)CC=C(N2)C2=CC=CC=C2 | [N-]=[N+]=[N:9][CH2:8][c:7]1[cH:6][cH:5][c:4]([CH2:3][CH:2]([CH3:1])[NH:12][c:13]2[n:14][cH:15][cH:16][c:17]([N:18]3[CH2:19][CH2:20][C:21](=[O:22])[N:23]4[CH2:24][CH:25]=[C:26]([c:27]5[cH:28][cH:29][cH:30][cH:31][cH:32]5)[N:33]=[C:34]34)[n:35]2)[cH:11][cH:10]1>>[CH3:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][NH2:9... | CC(Cc1ccc(CN=[N+]=[N-])cc1)Nc1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1 | CC(Cc1ccc(CN)cc1)Nc1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1 | null | [Pd] | C(C)OC(C)=O | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | O=C1CCN(c2ccnc(NCCc3ccccc3)n2)C2=NC(c3ccccc3)=CCN12 | [N-]=[N+]=[N;H0;D2;+0:1]-[C:2]-[c:3]>>[NH2;D1;+0:1]-[C:2]-[c:3] | null | [] | null | null | null | null | The mixture of 1-{2-[2-(4-azidomethyl-phenyl)-1-methyl-ethylamino]-pyrimidin-4-yl}-8-phenyl-1,2,3,6-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one, 1,4-cyclohexadiene (80 μL, 0.80 mmol) and palladium on carbon (100 mg) in ethylacetate (10 mL) was heated to reflux for 3 h and brought to room temperature. The mixture was filt... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | c1ccccc1.c1cncnc1.C1=CN=C2[NH]CCCN2C1.c1ccccc1 | Other | [Pd].C(C)OC(C)=O | null | null | CC(Cc1ccc(CN=[N+]=[N-])cc1)Nc1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1>[Pd].C(C)OC(C)=O>CC(Cc1ccc(CN)cc1)Nc1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6de1fbcc324e4549a960abe50ca5c371 | CC(Cc1ccc(CO)cc1)Nc1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1>>CC(Cc1ccc(C=O)cc1)Nc1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1 | OCC1=CC=C(C=C1)CC(C)NC1=NC=CC(=N1)N1C=2N(C(CC1)=O)CC=C(N2)C2=CC=CC=C2>>O=C1CCN(C=2N1CC=C(N2)C2=CC=CC=C2)C2=NC(=NC=C2)NC(CC2=CC=C(C=O)C=C2)C | [CH3:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][OH:9])[cH:10][cH:11]1)[NH:12][c:13]1[n:14][cH:15][cH:16][c:17]([N:18]2[CH2:19][CH2:20][C:21](=[O:22])[N:23]3[CH2:24][CH:25]=[C:26]([c:27]4[cH:28][cH:29][cH:30][cH:31][cH:32]4)[N:33]=[C:34]23)[n:35]1>>[CH3:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([CH:8]=[O:9])[cH:10][c... | CC(Cc1ccc(CO)cc1)Nc1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1 | CC(Cc1ccc(C=O)cc1)Nc1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1 | null | [O-2].[O-2].[Mn+4] | ClCCl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | O=C1CCN(c2ccnc(NCCc3ccccc3)n2)C2=NC(c3ccccc3)=CCN12 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | 3 | HOUR | The mixture of 1-{2-[2-(4-hydroxymethyl-phenyl)-1-methyl-ethylamino]-pyrimidin-4-yl}-8-phenyl-1,2,3,6-tetrahydro -pyrimido[1,2-a]pyrimidin-4-one (0.38 g, 0.81 mmol) and manganese dioxide (3.5 g, 40.5 mmol) in dichloromethane was stirred at room temperature for 3 h. The mixture was filtered off and concentrated to affor... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1.c1cncnc1.C1=CN=C2[NH]CCCN2C1.c1ccccc1 | null | [O-2].[O-2].[Mn+4].ClCCl | null | 3 | CC(Cc1ccc(CO)cc1)Nc1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1>[O-2].[O-2].[Mn+4].ClCCl>CC(Cc1ccc(C=O)cc1)Nc1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fe623d6467d644408b59e4f27cf4bf16 | CC(Cc1ccc(C=O)cc1)Nc1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1.CC[N+](=O)[O-]>>CC(=Cc1ccc(CC(C)Nc2nccc(N3CCC(=O)N4CC=C(c5ccccc5)N=C43)n2)cc1)[N+](=O)[O-] | O=C1CCN(C=2N1CC=C(N2)C2=CC=CC=C2)C2=NC(=NC=C2)NC(CC2=CC=C(C=O)C=C2)C.C(C)(=O)[O-].[NH4+].[N+](=O)([O-])CC>>CC(CC1=CC=C(C=C1)C=C(C)[N+](=O)[O-])NC1=NC=CC(=N1)N1C=2N(C(CC1)=O)CC=C(N2)C2=CC=CC=C2 | O=[CH:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][CH:9]([CH3:10])[NH:11][c:12]2[n:13][cH:14][cH:15][c:16]([N:17]3[CH2:18][CH2:19][C:20](=[O:21])[N:22]4[CH2:23][CH:24]=[C:25]([c:26]5[cH:27][cH:28][cH:29][cH:30][cH:31]5)[N:32]=[C:33]34)[n:34]2)[cH:35][cH:36]1.[CH3:1][CH2:2][N+:37](=[O:38])[O-:39]>>[CH3:1][C:2](=[CH:3][c:4]1[cH:5][... | CC(Cc1ccc(C=O)cc1)Nc1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1.CC[N+](=O)[O-] | CC(=Cc1ccc(CC(C)Nc2nccc(N3CCC(=O)N4CC=C(c5ccccc5)N=C43)n2)cc1)[N+](=O)[O-] | null | null | null | C-C Coupling | OtherReaction | 7ede86d40d3d69f429dde089476c8b7ffa9b74bf3050590255e6323d013c2daf | f736727903c0ad5511d468246b8e380897fd19905174c118ffa4ed4d3651f6ea | O=C1CCN(c2ccnc(NCCc3ccccc3)n2)C2=NC(c3ccccc3)=CCN12 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[CH2;D2;+0:6]-[#7;+:7](-[O;-;D1;H0:8])=[O;D1;H0:9]>>[C;D1;H3:5]-[C;H0;D3;+0:6](=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[#7;+:7](-[O;-;D1;H0:8])=[O;D1;H0:9] | null | [] | null | null | null | null | The mixture of 4-{2-[4-(4-oxo-8-phenyl-3,4-dihydro-2H,6H-pyrimido[1,2-a]pyrimidin-1-yl) -pyrimidin-2-ylamino]-propyl}-benzaldehyde (35 mg, 0.08 mmol), ammonium acetate (10 mg, 0.16 mmol) in nitroethane (5 mL) was heated to reflux for 4 h. The mixture was brought to room temperature and concentrated. The residue was dis... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitro group | Enamine | null | null | c1ccccc1.c1cncnc1.C1=CN=C2[NH]CCCN2C1.c1ccccc1 | HO- | null | null | null | CC(Cc1ccc(C=O)cc1)Nc1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1.CC[N+](=O)[O-]>>CC(=Cc1ccc(CC(C)Nc2nccc(N3CCC(=O)N4CC=C(c5ccccc5)N=C43)n2)cc1)[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-18ca248961c84170805d4e3148ba8a0c | CC(=Cc1ccc(CC(C)Nc2nccc(N3CCC(=O)N4CC=C(c5ccccc5)N=C43)n2)cc1)[N+](=O)[O-]>>CC(N)Cc1ccc(CC(C)Nc2nccc(N3CCC(=O)N4CC=C(c5ccccc5)N=C43)n2)cc1 | CC(CC1=CC=C(C=C1)C=C(C)[N+](=O)[O-])NC1=NC=CC(=N1)N1C=2N(C(CC1)=O)CC=C(N2)C2=CC=CC=C2>>NC(CC1=CC=C(C=C1)CC(C)NC1=NC=CC(=N1)N1C=2N(C(CC1)=O)CC=C(N2)C2=CC=CC=C2)C | O=[N+:3]([O-])[C:2]([CH3:1])=[CH:4][c:5]1[cH:6][cH:7][c:8]([CH2:9][CH:10]([CH3:11])[NH:12][c:13]2[n:14][cH:15][cH:16][c:17]([N:18]3[CH2:19][CH2:20][C:21](=[O:22])[N:23]4[CH2:24][CH:25]=[C:26]([c:27]5[cH:28][cH:29][cH:30][cH:31][cH:32]5)[N:33]=[C:34]34)[n:35]2)[cH:36][cH:37]1>>[CH3:1][CH:2]([NH2:3])[CH2:4][c:5]1[cH:6][c... | CC(=Cc1ccc(CC(C)Nc2nccc(N3CCC(=O)N4CC=C(c5ccccc5)N=C43)n2)cc1)[N+](=O)[O-] | CC(N)Cc1ccc(CC(C)Nc2nccc(N3CCC(=O)N4CC=C(c5ccccc5)N=C43)n2)cc1 | null | [Pd] | CO | Reduction | OtherReaction | 4337e4e8b75c4193a30be38c3139251eb50201a1e90dac1ecfc293dd3e226a46 | 1ad3bfd18d4cba7c52a6c2c4705cfa4e2dc99589d9555154a809489f21a7a436 | O=C1CCN(c2ccnc(NCCc3ccccc3)n2)C2=NC(c3ccccc3)=CCN12 | O=[N+;H0;D3:1](-[O-])-[C;H0;D3;+0:2](-[C;D1;H3:3])=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:3]-[CH;D3;+0:2](-[NH2;D1;+0:1])-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | Through a mixture of 1-(2-{1-methyl-2-[4-(2-nitro-propenyl)-phenyl]-ethylamino}-pyrimidin-4-yl)-8-phenyl-1,2,3,6-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one (10 mg, 0.02 mmol) and palladium on carbon (cat) in methanol was bubbled hydrogen through a balloon for 17 h. The mixure was filtered through celite, concentrated an... | 10.6084/m9.figshare.5104873.v1 | null | Enamine | Primary amine | null | null | c1ccccc1.c1cncnc1.C1=CN=C2[NH]CCCN2C1.c1ccccc1 | Other | [Pd].CO | null | null | CC(=Cc1ccc(CC(C)Nc2nccc(N3CCC(=O)N4CC=C(c5ccccc5)N=C43)n2)cc1)[N+](=O)[O-]>[Pd].CO>CC(N)Cc1ccc(CC(C)Nc2nccc(N3CCC(=O)N4CC=C(c5ccccc5)N=C43)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c8818ae657bd4d0dacbe9faef226530c | CC(C)(O)c1cccc(Br)c1.N#CCCl.O=S(=O)(O)O>>CC(C)(NC(=O)CCl)c1cccc(Br)c1 | BrC=1C=C(C=CC1)C(C)(C)O.ClCC#N.S(O)(O)(=O)=O>>BrC=1C=C(C=CC1)C(C)(C)NC(CCl)=O | O[C:2]([CH3:1])([CH3:3])[c:9]1[cH:10][cH:11][cH:12][c:13]([Br:14])[cH:15]1.[N:4]#[C:5][CH2:7][Cl:8].O=S(=O)(O)[OH:6]>>[CH3:1][C:2]([CH3:3])([NH:4][C:5](=[O:6])[CH2:7][Cl:8])[c:9]1[cH:10][cH:11][cH:12][c:13]([Br:14])[cH:15]1 | CC(C)(O)c1cccc(Br)c1.N#CCCl.O=S(=O)(O)O | CC(C)(NC(=O)CCl)c1cccc(Br)c1 | null | null | C(C)(=O)O | Heteroatom Alkylation and Arylation | OtherReaction | 1d5b8ab7abc796c8fe1a4bbe88d643f3667784ffa1e5d5bdf2ecec75239c4174 | 351ef33c26e45ccdbae92f97c6925d748e3ebc471a863d8f431e8ded2d7e850d | c1ccccc1 | O-S(=O)(=O)-[OH;D1;+0:1].O-[C;H0;D4;+0:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[c:5](:[c:6]):[c:7].[Cl;D1;H0:8]-[C:9]-[C;H0;D2;+0:10]#[N;H0;D1;+0:11]>>[C;D1;H3:3]-[C;H0;D4;+0:2](-[C;D1;H3:4])(-[NH;D2;+0:11]-[C;H0;D3;+0:10](=[O;H0;D1;+0:1])-[C:9]-[Cl;D1;H0:8])-[c:5](:[c:6]):[c:7] | null | [] | 0 | CELSIUS | 17 | HOUR | To a mixture of the 2-(3-bromo-phenyl)-propan-2-ol and (0.76 g, 3.6 mmol) and chloro-acetonitrile (7 mL) was added acetic acid (0.6 mL) and the resulting mixture was cooled to 0° C. Concentrated sulfuric acid (0.6 mL) was added dropwise and the mixture was brought to room temperature and stirred for 17 h. Mixture was p... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Tertiary alcohol | Secondary amide | null | null | c1ccccc1 | HO- | C(C)(=O)O | 0 | 17 | CC(C)(O)c1cccc(Br)c1.N#CCCl.O=S(=O)(O)O>C(C)(=O)O>CC(C)(NC(=O)CCl)c1cccc(Br)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c93c2c43beef47f48b7d8aba95b9eaec | CC(C)(NC(=O)CCl)c1cccc(Br)c1>>CC(C)(N)c1cccc(Br)c1 | O.BrC=1C=C(C=CC1)C(C)(C)NC(CCl)=O.NC(=S)N.C(C)(=O)O>>BrC=1C=C(C=CC1)C(C)(C)N | O=C(CCl)[NH:4][C:2]([CH3:1])([CH3:3])[c:5]1[cH:6][cH:7][cH:8][c:9]([Br:10])[cH:11]1>>[CH3:1][C:2]([CH3:3])([NH2:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([Br:10])[cH:11]1 | CC(C)(NC(=O)CCl)c1cccc(Br)c1 | CC(C)(N)c1cccc(Br)c1 | null | null | C(C)O | Reduction | Hydrogenolysis of amides/imides/carbamates | 807b1f1939ea7d761c5d620a58a82fc0384736a2623a6465702aec6b6eafca82 | 2e2d3841e5ab0432159afeb516096047b79f5ff710ff12d384f8f6e373d52484 | c1ccccc1 | Cl-C-C(=O)-[NH;D2;+0:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[c:5]>>[C;D1;H3:3]-[C:2](-[C;D1;H3:4])(-[NH2;D1;+0:1])-[c:5] | null | [] | null | null | null | null | The mixture of N-[1-(3-bromo-phenyl)-1-methyl-ethyl]-2-chloro-acetamide (1.0 g, 3.5 mmol), thiourea (0.32 g, 4.2 mmol), acetic acid (1.5 mL) in ethanol (7 mL) was heated to reflux for 10 h and brought to room temperature. Water was added to the mixture until a precipitate was formed which was filtered. The filtrate was... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amide | Primary amine | null | null | c1ccccc1 | HCl | C(C)O | null | null | CC(C)(NC(=O)CCl)c1cccc(Br)c1>C(C)O>CC(C)(N)c1cccc(Br)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-82f70b5da0c44140bd1eb2eb0d078c06 | C=CC(=O)OCC.CC(C)(N)c1cccc(Br)c1.CN(C1CCCCC1)C1CCCCC1>>COC(=O)C(C)=Cc1cccc(C(C)(C)N)c1 | C(C=C)(=O)OCC.C(C)(C)(C)P(C(C)(C)C)C(C)(C)C.BrC=1C=C(C=CC1)C(C)(C)N.CN(C1CCCCC1)C1CCCCC1>>COC(C(=CC1=CC(=CC=C1)C(C)(C)N)C)=O | C[CH2:1][O:2][C:3](=[O:4])[CH:5]=[CH2:6].Br[c:8]1[cH:9][cH:10][cH:11][c:12]([C:13]([CH3:14])([CH3:15])[NH2:16])[cH:17]1.CN(C1CCCCC1)C1CCCC[CH2:7]1>>[CH3:1][O:2][C:3](=[O:4])[C:5]([CH3:6])=[CH:7][c:8]1[cH:9][cH:10][cH:11][c:12]([C:13]([CH3:14])([CH3:15])[NH2:16])[cH:17]1 | C=CC(=O)OCC.CC(C)(N)c1cccc(Br)c1.CN(C1CCCCC1)C1CCCCC1 | COC(=O)C(C)=Cc1cccc(C(C)(C)N)c1 | 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] | O1CCOCC1.O | C-C Coupling | OtherReaction | 206806302ed78190ad75d1f786fc14274f4bbd23851875e21565ae44e45d1e3c | 8e0661f9e28121ac6c2a1c7506a439ed7a76b37b3cf9ee523f78f73fb18e012e | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-N(-C1-C-C-C-C-C-1)-C1-C-C-C-C-[CH2;D2;+0:6]-1.C-[CH2;D2;+0:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[CH;D2;+0:11]=[CH2;D1;+0:12]>>[CH3;D1;+0:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[C;H0;D3;+0:11](-[CH3;D1;+0:12])=[CH;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | 80 | CELSIUS | null | null | The mixture of 1-(3-bromo-phenyl)-1-methyl-ethylamine (0.74 g, 3.5 mmol), tris(dibenzylideneacetone)dipalladium (0.19 g, 0.21 mmol), and N-methyldicyclohexylamine (10 mmol) was purged with nitrogen followed by the addition of 1,4-dioxane (7 mL) and tri-tert-butylphospine (85 mg, 0.42 mmol). The mixture was again purged... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Tertiary amine.Vinyl | Ester | c1ccccc1.C1CCCCC1.C1CCCCC1 | c1ccccc1 | 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].O1CCOCC1.O | 80 | null | C=CC(=O)OCC.CC(C)(N)c1cccc(Br)c1.CN(C1CCCCC1)C1CCCCC1>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].O1CCOCC1.O>COC(=O)C(C)=Cc1cccc(C(C)(C)N)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-69ee3bd99eda4cc58d6d1e27af82a7af | COC(=O)C(C)=Cc1cccc(C(C)(C)N)c1>>COC(=O)C(C)Cc1cccc(C(C)(C)N)c1 | COC(C(=CC1=CC(=CC=C1)C(C)(C)N)C)=O.[Mg]>>COC(C(CC1=CC(=CC=C1)C(C)(C)N)C)=O | [CH3:1][O:2][C:3](=[O:4])[C:5]([CH3:6])=[CH:7][c:8]1[cH:9][cH:10][cH:11][c:12]([C:13]([CH3:14])([CH3:15])[NH2:16])[cH:17]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH3:6])[CH2:7][c:8]1[cH:9][cH:10][cH:11][c:12]([C:13]([CH3:14])([CH3:15])[NH2:16])[cH:17]1 | COC(=O)C(C)=Cc1cccc(C(C)(C)N)c1 | COC(=O)C(C)Cc1cccc(C(C)(C)N)c1 | null | null | CO | Reduction | Hydrogenation (double to single) | c04c38f95d7b746e5bdb99c368a7a33956c97b95b54c7ad89be2a85526386ec9 | 9a50abf8d2e4cd9195d7a0cadbe97483a261a81cf70b653cfddd5ecf76d383a6 | c1ccccc1 | [C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:5](-[C;D1;H3:6])=[CH;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:5](-[C;D1;H3:6])-[CH2;D2;+0:7]-[c:8](:[c:9]):[c:10] | null | [] | null | null | null | null | The mixture of 3-[3-(1-amino-1-methyl-ethyl)-phenyl]-2-methylacrylic acid methyl ester (2.0 g, 8.6 mmol), magnesium (0.63 g, 25.8 mmol) in methanol was heated to reflux for 3 h until the starting material was consumed. The mixture was brought to room temperature, filtered and the filtrate was concentrated. The residue ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | null | null | c1ccccc1 | null | CO | null | null | COC(=O)C(C)=Cc1cccc(C(C)(C)N)c1>CO>COC(=O)C(C)Cc1cccc(C(C)(C)N)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9a439986ea774601a847d5a4ee6fdaee | CC(Cc1cccc(C(C)(C)NC(=O)OC(C)(C)C)c1)NC(=O)OCc1ccccc1>>CC(N)Cc1cccc(C(C)(C)NC(=O)OC(C)(C)C)c1 | C(C)(C)(C)OC(NC(C)(C)C1=CC(=CC=C1)CC(C)NC(=O)OCC1=CC=CC=C1)=O.C1=CCC=CC1>>C(C)(C)(C)OC(NC(C)(C)C1=CC(=CC=C1)CC(C)N)=O | O=C(OCc1ccccc1)[NH:3][CH:2]([CH3:1])[CH2:4][c:5]1[cH:6][cH:7][cH:8][c:9]([C:10]([CH3:11])([CH3:12])[NH:13][C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[cH:21]1>>[CH3:1][CH:2]([NH2:3])[CH2:4][c:5]1[cH:6][cH:7][cH:8][c:9]([C:10]([CH3:11])([CH3:12])[NH:13][C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])... | CC(Cc1cccc(C(C)(C)NC(=O)OC(C)(C)C)c1)NC(=O)OCc1ccccc1 | CC(N)Cc1cccc(C(C)(C)NC(=O)OC(C)(C)C)c1 | null | [Pd] | CO | Reduction | Hydrogenolysis of amides/imides/carbamates | 087b6600ba91d3df931fe6979f2445c192cbfd59e04fd2d8a10f7c7573ac669f | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | c1ccccc1 | O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[C:2](-[C:3])-[C;D1;H3:4]>>[C:3]-[C:2](-[C;D1;H3:4])-[NH2;D1;+0:1] | null | [] | null | null | null | null | To a mixture of {1-[3-(2-benzyloxycarbonylamino-propyl)-phenyl]-1-methyl-ethyl}-carbamic acid tert-butyl ester (0.28 g, 0.65 mmol), 1,4-cyclohexadiene (0.31 mL, 3.25 mmol) and Pd/C (cat.) in methanol was heated to reflux for 17 h. The mixture was filtered through celite and concentrated to afford light yellow oil. M+1=... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | c1ccccc1 | null | c1ccccc1 | HO- | [Pd].CO | null | null | CC(Cc1cccc(C(C)(C)NC(=O)OC(C)(C)C)c1)NC(=O)OCc1ccccc1>[Pd].CO>CC(N)Cc1cccc(C(C)(C)NC(=O)OC(C)(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ff635817f03644f0ba08ecbb08762b29 | CC(N)Cc1cccc(C(C)(C)NC(=O)OC(C)(C)C)c1.CS(=O)(=O)c1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1>>CC(Cc1cccc(C(C)(C)NC(=O)OC(C)(C)C)c1)Nc1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1 | C(C)(C)(C)OC(NC(C)(C)C1=CC(=CC=C1)CC(C)N)=O.CS(=O)(=O)C1=NC=CC(=N1)N1C=2N(C(CC1)=O)CC=C(N2)C2=CC=CC=C2.O>>C(C)(C)(C)OC(NC(C)(C1=CC(=CC=C1)CC(C)NC1=NC=CC(=N1)N1C=2N(C(CC1)=O)CC=C(N2)C2=CC=CC=C2)C)=O | [CH3:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([C:9]([CH3:10])([CH3:11])[NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20]1)[NH2:21].CS(=O)(=O)[c:22]1[n:23][cH:24][cH:25][c:26]([N:27]2[CH2:28][CH2:29][C:30](=[O:31])[N:32]3[CH2:33][CH:34]=[C:35]([c:36]4[cH:37][cH:38][cH:39][cH:40][cH:41]4)[N:42]=... | CC(N)Cc1cccc(C(C)(C)NC(=O)OC(C)(C)C)c1.CS(=O)(=O)c1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1 | CC(Cc1cccc(C(C)(C)NC(=O)OC(C)(C)C)c1)Nc1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1 | null | null | CN1CCCC1=O | Heteroatom Alkylation and Arylation | OtherReaction | 289adcacbe89f1503fb3c9d1b660927aaeb421d7b5520077738f22dce3010144 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=C1CCN(c2ccnc(NCCc3ccccc3)n2)C2=NC(c3ccccc3)=CCN12 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7](-[C;D1;H3:8])-[NH2;D1;+0:9]>>[C:6]-[C:7](-[C;D1;H3:8])-[NH;D2;+0:9]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | null | [] | 100 | CELSIUS | null | null | To a mixture of {1-[3-(2-amino-propyl)-phenyl]-1-methyl -ethyl}-carbamic acid tert-butyl ester (0.19 g, 0.65 mmol) and 1-(2-methanesulfonyl-pyrimidin-4-yl) -8-phenyl-1,2,3,6-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one (0.26 g, 0.72 mmol) in NMP (2 mL) was heated to 100° C. for 17 h. The mixture was poured into water (15 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.C1=CN=C2[NH]CCCN2C1.c1ccccc1 | HO- | CN1CCCC1=O | 100 | null | CC(N)Cc1cccc(C(C)(C)NC(=O)OC(C)(C)C)c1.CS(=O)(=O)c1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1>CN1CCCC1=O>CC(Cc1cccc(C(C)(C)NC(=O)OC(C)(C)C)c1)Nc1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-87085bbfff944db9bf5d4bd3f1482fe7 | CC(Cc1cccc(C(C)(C)NC(=O)OC(C)(C)C)c1)Nc1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1>>CC(Cc1cccc(C(C)(C)N)c1)Nc1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1 | C(C)(C)(C)OC(NC(C)(C1=CC(=CC=C1)CC(C)NC1=NC=CC(=N1)N1C=2N(C(CC1)=O)CC=C(N2)C2=CC=CC=C2)C)=O.FC(C(=O)O)(F)F>>NC(C)(C)C=1C=C(C=CC1)CC(C)NC1=NC=CC(=N1)N1C=2N(C(CC1)=O)CC=C(N2)C2=CC=CC=C2 | CC(C)(C)OC(=O)[NH:12][C:9]([c:8]1[cH:7][cH:6][cH:5][c:4]([CH2:3][CH:2]([CH3:1])[NH:14][c:15]2[n:16][cH:17][cH:18][c:19]([N:20]3[CH2:21][CH2:22][C:23](=[O:24])[N:25]4[CH2:26][CH:27]=[C:28]([c:29]5[cH:30][cH:31][cH:32][cH:33][cH:34]5)[N:35]=[C:36]34)[n:37]2)[cH:13]1)([CH3:10])[CH3:11]>>[CH3:1][CH:2]([CH2:3][c:4]1[cH:5][c... | CC(Cc1cccc(C(C)(C)NC(=O)OC(C)(C)C)c1)Nc1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1 | CC(Cc1cccc(C(C)(C)N)c1)Nc1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1 | null | null | ClCCl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C1CCN(c2ccnc(NCCc3ccccc3)n2)C2=NC(c3ccccc3)=CCN12 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[c:5]>>[C;D1;H3:3]-[C:2](-[C;D1;H3:4])(-[NH2;D1;+0:1])-[c:5] | null | [] | null | null | 30 | MINUTE | To a mixture of [1-methyl-1-(3-{2-[4-(4-oxo-8-phenyl-3,4-dihydro-2H, 6H-pyrimido[1,2-a]pyrimidin-1-yl)-pyrimidin-2-ylamino]-propyl}-phenyl)-ethyl]-carbamic acid tert-butyl ester (0.25 g, 0.42 mmol) and trifluoroacetic acid (1 mL) in dichloromethane (2 mL) was stirred at room temperature for 30 min. The mixture was wash... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1cncnc1.C1=CN=C2[NH]CCCN2C1.c1ccccc1 | HO- | ClCCl | null | 0.5 | CC(Cc1cccc(C(C)(C)NC(=O)OC(C)(C)C)c1)Nc1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1>ClCCl>CC(Cc1cccc(C(C)(C)N)c1)Nc1nccc(N2CCC(=O)N3CC=C(c4ccccc4)N=C32)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a93d0ed17ef24fb492871f8e95ea8aed | N=C(N)N.NCC(O)CN>>N=C1NCC(O)CN1 | OC(CN)CN.Cl.NC(=N)N.CC(C)O>>Cl.N=C1NCC(CN1)O | N[C:3](N)=[NH:2].[NH2:4][CH2:5][CH:6]([OH:7])[CH2:8][NH2:9]>>[NH:2]=[C:3]1[NH:4][CH2:5][CH:6]([OH:7])[CH2:8][NH:9]1 | N=C(N)N.NCC(O)CN | N=C1NCC(O)CN1 | null | null | CC#N | Heteroatom Alkylation and Arylation | OtherReaction | 884557aedb9ba33f3bd73c1a9f24022128ef861455c47665d1114455446729ad | 9ad8d209678ee75009dc7068f43e3d0b5ea50e6f5b5deea7157a5815191d1c8b | N=C1NCCCN1 | N-[C;H0;D3;+0:1](-N)=[N;D1;H1:2].[NH2;D1;+0:3]-[C:4]-[C:5]-[C:6]-[NH2;D1;+0:7]>>[N;D1;H1:2]=[C;H0;D3;+0:1]1-[NH;D2;+0:3]-[C:4]-[C:5]-[C:6]-[NH;D2;+0:7]-1 | null | [] | 140 | CELSIUS | null | null | A mixture of 2-hydroxy -1,3-diaminopropane (9.80 g, 108 mmol) and guanidine hydrochloride (10.4 g, 108 mmol) in a 100 mL RBF was heated at 140° C. under nitrogen for 5 h. The reaction mixture, while under vigorous stirring, was let cooled to 100° C. whereby a mixture of iPrOH (5 mL) and CH3CN (5 mL) were added, resulti... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine.Primary amine.Primary amine | Secondary amine.Secondary amine | null | C1CNCNC1 | C1CNCNC1 | Other | CC#N | 140 | null | N=C(N)N.NCC(O)CN>CC#N>N=C1NCC(O)CN1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-53d91446c3054d59a42f9437d9e53686 | CCOC(=O)CC(=O)c1ccccc1.N=C1NCC(O)CN1>>O=c1cc(-c2ccccc2)nc2n1CC(O)CN2 | C(C)OC(CC(C1=CC=CC=C1)=O)=O.C(=O)([O-])[O-].[K+].[K+].Cl.N=C1NCC(CN1)O>>OC1CNC=2N(C(C=C(N2)C2=CC=CC=C2)=O)C1 | CCO[C:2](=[O:1])[CH2:3][C:4](=O)[c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1.[NH:11]=[C:12]1[NH:13][CH2:14][CH:15]([OH:16])[CH2:17][NH:18]1>>[O:1]=[c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]2[n:13]1[CH2:14][CH:15]([OH:16])[CH2:17][NH:18]2 | CCOC(=O)CC(=O)c1ccccc1.N=C1NCC(O)CN1 | O=c1cc(-c2ccccc2)nc2n1CC(O)CN2 | null | null | CCO | Aromatic Heterocycle Formation | OtherReaction | 8f00f16f1c9d53f5f46d6d9a2025926fef0c98e92dd7de5b7a8939471e83a088 | f590641b01cb525446469ed6ced5b738f453feb2f025056e9767d27c06e94b8b | O=c1cc(-c2ccccc2)nc2n1CCCN2 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[C;H0;D3;+0:4](=O)-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11]1-[#7:12]-[C:13]-[C:14]-[C:15]-[NH;D2;+0:16]-1>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[cH;D2;+0:3]:[c;H0;D3;+0:4](-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]:[c:9]):[n;H0;D2;+0:10]:[c;H0;D3;+0:11]2:[n... | null | [] | 90 | CELSIUS | 17 | HOUR | In a 250 mL RBF with a stirrer bar, a mixture of 3-oxo-3-phenyl-propionic acid ethyl ester (15 g, 78 mmol), K2CO3 (11.0 g, 80 mmol) and 2-imino-hexahydro-pyrimidin-5-ol hydrochloride (11.8 g, 78 mmol) in EtOH (150 mL) was heated at 90° C. under nitrogen overnight. After 17 h, the mixture was cooled to room temperature,... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Secondary amine | null | C1CNCNC1 | c1ccn2c(n1)NC[CH]C2 | c1ccccc1.c1ccn2c(n1)NC[CH]C2 | HO- | CCO | 90 | 17 | CCOC(=O)CC(=O)c1ccccc1.N=C1NCC(O)CN1>CCO>O=c1cc(-c2ccccc2)nc2n1CC(O)CN2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-764a1ae4db054e5ea156281aaf351f1a | CC(C)(C)[Si](C)(C)OC1CN(c2ccnc(S(C)(=O)=O)n2)c2nc(-c3ccccc3)cc(=O)n2C1.C[C@H](N)c1ccccc1>>CC(Nc1nccc(N2CC(O[Si](C)(C)C(C)(C)C)Cn3c2nc(-c2ccccc2)cc3=O)n1)c1ccccc1 | C(C)(C)(C)[Si](OC1CN(C=2N(C(C=C(N2)C2=CC=CC=C2)=O)C1)C1=NC(=NC=C1)S(=O)(=O)C)(C)C.C1(=CC=CC=C1)[C@H](C)N>>C(C)(C)(C)[Si](OC1CN(C=2N(C(C=C(N2)C2=CC=CC=C2)=O)C1)C1=NC(=NC=C1)NC(C)C1=CC=CC=C1)(C)C | CS(=O)(=O)[c:4]1[n:5][cH:6][cH:7][c:8]([N:9]2[CH2:10][CH:11]([O:12][Si:13]([CH3:14])([CH3:15])[C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:20][n:21]3[c:22]2[n:23][c:24](-[c:25]2[cH:26][cH:27][cH:28][cH:29][cH:30]2)[cH:31][c:32]3=[O:33])[n:34]1.[CH3:1][C@H:2]([NH2:3])[c:35]1[cH:36][cH:37][cH:38][cH:39][cH:40]1>>[CH3:1][CH:2]... | CC(C)(C)[Si](C)(C)OC1CN(c2ccnc(S(C)(=O)=O)n2)c2nc(-c3ccccc3)cc(=O)n2C1.C[C@H](N)c1ccccc1 | CC(Nc1nccc(N2CC(O[Si](C)(C)C(C)(C)C)Cn3c2nc(-c2ccccc2)cc3=O)n1)c1ccccc1 | null | null | O1CCOCC1.CCOC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 289adcacbe89f1503fb3c9d1b660927aaeb421d7b5520077738f22dce3010144 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1cc(-c2ccccc2)nc2n1CCCN2c1ccnc(NCc2ccccc2)n1 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C;D1;H3:6]-[C@H;D3;+0:7](-[NH2;D1;+0:8])-[c:9](:[c:10]):[c:11]>>[C;D1;H3:6]-[CH;D3;+0:7](-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5])-[c:9](:[c:10]):[c:11] | null | [] | 110 | CELSIUS | null | null | A mixture of 7-(tert-butyl-dimethyl-silanyloxy)-9-(2-methanesulfonyl-pyrimidin-4-yl)-2-phenyl-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one, prepared from last step (0.6 mmol) and (S)-1-phenylethylamine (1.0 mL, 7.8 mmol) in dioxane (6 mL) was heated at 110° C. for 17 h. The brown solution was cooled to room temper... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccn2c(n1)NC[CH]C2.c1ccccc1.c1ccccc1 | HO- | O1CCOCC1.CCOC(=O)C | 110 | null | CC(C)(C)[Si](C)(C)OC1CN(c2ccnc(S(C)(=O)=O)n2)c2nc(-c3ccccc3)cc(=O)n2C1.C[C@H](N)c1ccccc1>O1CCOCC1.CCOC(=O)C>CC(Nc1nccc(N2CC(O[Si](C)(C)C(C)(C)C)Cn3c2nc(-c2ccccc2)cc3=O)n1)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aa3c7d36b47c4cf790899e0a97557549 | CC(Nc1nccc(N2CC(O[Si](C)(C)C(C)(C)C)Cn3c2nc(-c2ccccc2)cc3=O)n1)c1ccccc1>>CC(Nc1nccc(N2CC(O)Cn3c2nc(-c2ccccc2)cc3=O)n1)c1ccccc1 | C(=O)(O)[O-].[Na+].C(C)(C)(C)[Si](OC1CN(C=2N(C(C=C(N2)C2=CC=CC=C2)=O)C1)C1=NC(=NC=C1)NC(C)C1=CC=CC=C1)(C)C.C(Cl)Cl.Cl>>OC1CN(C=2N(C(C=C(N2)C2=CC=CC=C2)=O)C1)C1=NC(=NC=C1)NC(C)C1=CC=CC=C1 | CC(C)(C)[Si](C)(C)[O:12][CH:11]1[CH2:10][N:9]([c:8]2[cH:7][cH:6][n:5][c:4]([NH:3][CH:2]([CH3:1])[c:28]3[cH:29][cH:30][cH:31][cH:32][cH:33]3)[n:27]2)[c:15]2[n:14]([c:25](=[O:26])[cH:24][c:17](-[c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[n:16]2)[CH2:13]1>>[CH3:1][CH:2]([NH:3][c:4]1[n:5][cH:6][cH:7][c:8]([N:9]2[CH2:10][C... | CC(Nc1nccc(N2CC(O[Si](C)(C)C(C)(C)C)Cn3c2nc(-c2ccccc2)cc3=O)n1)c1ccccc1 | CC(Nc1nccc(N2CC(O)Cn3c2nc(-c2ccccc2)cc3=O)n1)c1ccccc1 | null | null | CO | Deprotection | Alcohol deprotection from silyl ethers | 050b4fb4e1e9936189860d27dded10ae70a294a642c52f800eb9d5aaef7955cc | 88623e19d23cdfe8e1a4c167fd6cfc51d774a1c784b87a7bb2df8153ee93e67a | O=c1cc(-c2ccccc2)nc2n1CCCN2c1ccnc(NCc2ccccc2)n1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3]-[#7:4])-[C:5]-[#7;a:6]>>[#7:4]-[C:3]-[C:2](-[OH;D1;+0:1])-[C:5]-[#7;a:6] | null | [] | null | null | 16 | HOUR | A solution of 7-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-9-[2-(1-phenyl-ethylamino)-pyrimidin-4-yl]-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one (20 mg) in MeOH (3 mL)-DCM (1 mL) was treated with HCl (conc. 1.5 mL). After the mixture was stirred at room temperature for 16 h, it was neutralized with NaHCO3 (aq) an... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Secondary alcohol | null | null | c1cncnc1.c1ccn2c(n1)NC[CH]C2.c1ccccc1.c1ccccc1 | Other | CO | null | 16 | CC(Nc1nccc(N2CC(O[Si](C)(C)C(C)(C)C)Cn3c2nc(-c2ccccc2)cc3=O)n1)c1ccccc1>CO>CC(Nc1nccc(N2CC(O)Cn3c2nc(-c2ccccc2)cc3=O)n1)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ee5713a5f957405987c2c19d732f5004 | CCOC(=O)CC(=CC#N)c1ccccc1.NCCN>>O=c1cc(-c2ccccc2)cc2n1CCN2 | C(C)OC(CC(=CC#N)C1=CC=CC=C1)=O.C(CN)N>>C1(=CC=CC=C1)C=1C=C2N(C(C1)=O)CCN2 | CCO[C:2](=[O:1])[CH2:3][C:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)=[CH:11][C:12]#N.[NH2:13][CH2:14][CH2:15][NH2:16]>>[O:1]=[c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[cH:11][c:12]2[n:13]1[CH2:14][CH2:15][NH:16]2 | CCOC(=O)CC(=CC#N)c1ccccc1.NCCN | O=c1cc(-c2ccccc2)cc2n1CCN2 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | f4c8ee0762a74d2b935553935519bf1eb02fcd52cc72bfe6895915070834faac | 78e63bdc1504c9d55ec85b6a599f1cbdd667d3ae42ca4f82f3661c62d981c530 | O=c1cc(-c2ccccc2)cc2n1CCN2 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[C;H0;D3;+0:4](=[CH;D2;+0:5]-[C;H0;D2;+0:6]#N)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11].[NH2;D1;+0:12]-[C:13]-[C:14]-[NH2;D1;+0:15]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[cH;D2;+0:3]:[c;H0;D3;+0:4](-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]):[cH;D2;+0:5]:[c;H0;D3;+0:6]2:[n;H0;... | null | [] | 160 | CELSIUS | null | null | 4-Cyano-3-phenyl-but-3-enoic acid ethyl ester (crude, 9.37 g, 0.043 mol), ethylenediamine (3 mL, 0.043 mol) were mixed in dichlorobenze (20 mL) and heated at 160° C. overnight. The resulting suspension was cooled to room temperature, filtered, and the filtrated cake was washed with EtOAc and finally dried to provide th... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Nitrile.Primary amine.Primary amine | Secondary amine | null | c1ccn2c(c1)NCC2 | c1ccccc1.c1ccn2c(c1)NCC2 | HO- | null | 160 | null | CCOC(=O)CC(=CC#N)c1ccccc1.NCCN>>O=c1cc(-c2ccccc2)cc2n1CCN2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4adc0ba0538a4090bb0ebdd5cc78d520 | CSc1nccc(Cl)n1.O=c1cc(-c2ccccc2)cc2n1CCCN2>>CSc1nccc(N2CCCn3c2cc(-c2ccccc2)cc3=O)n1 | ClC1=NC(=NC=C1)SC.C1(=CC=CC=C1)C=1C=C2N(CCCN2)C(C1)=O.CC(C)([O-])C.[Na+].C=1C=CC(=CC1)P(C=2C=CC=CC2)C3=CC=C4C=CC=CC4=C3C5=C6C=CC=CC6=CC=C5P(C=7C=CC=CC7)C=8C=CC=CC8>>CSC1=NC=CC(=N1)N1C=2N(CCC1)C(C=C(C2)C2=CC=CC=C2)=O | Cl[c:7]1[cH:6][cH:5][n:4][c:3]([S:2][CH3:1])[n:25]1.[NH:8]1[CH2:9][CH2:10][CH2:11][n:12]2[c:13]1[cH:14][c:15](-[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[cH:22][c:23]2=[O:24]>>[CH3:1][S:2][c:3]1[n:4][cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][CH2:11][n:12]3[c:13]2[cH:14][c:15](-[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2... | CSc1nccc(Cl)n1.O=c1cc(-c2ccccc2)cc2n1CCCN2 | CSc1nccc(N2CCCn3c2cc(-c2ccccc2)cc3=O)n1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | e4ffddb286271207ecd79dac97a88aa5f42eaa4284924638aeeb1b9d705dd954 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(-c2ccccc2)cc2n1CCCN2c1ccncn1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#16:4]):[#7;a:5]:[c:6]:[c:7]:1.[c:8]:[c:9]1:[#7;a:10](:[c:11])-[C:12]-[C:13]-[C:14]-[NH;D2;+0:15]-1>>[#16:4]-[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:15]2-[C:14]-[C:13]-[C:12]-[#7;a:10](:[c:11]):[c:9]-2:[c:8]):[c:7]:[c:6]:[#7;a:5]:1 | null | [] | 70 | CELSIUS | null | null | To a mixture of 8-phenyl-1,2,3,4-tetrahydro-pyrido[1,2-a]pyrimidin-6-one (1.86 g, 8.23 mmol), sodium tert-butoxide (1.6 g, 16 mmol), BINAP (0.15 g, 0.207 mmol), and Pd (OAc)2 (55 mg, 0.2 mmol) was added toluene (20 mL) and 4-chloro -2-methylthiopyrimidine (1.5 mL, 12 mmol). After purged with N2 for 10 min, the overall ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1cncnc1.c1ccn2c(c1)NCCC2 | c1cncnc1.c1ccn2c(c1)NCCC2 | c1cncnc1.c1ccn2c(c1)NCCC2.c1ccccc1 | HCl | C1(=CC=CC=C1)C | 70 | null | CSc1nccc(Cl)n1.O=c1cc(-c2ccccc2)cc2n1CCCN2>C1(=CC=CC=C1)C>CSc1nccc(N2CCCn3c2cc(-c2ccccc2)cc3=O)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-18463e1b15a84f3184de7f73294a6b77 | CSc1nccc(N2CCCn3c2cc(-c2ccccc2)cc3=O)n1.O=c1cc(-c2ccccc2)cc2n1CCN2>>CSc1nccc(N2CCn3c2cc(-c2ccccc2)cc3=O)n1 | CSC1=NC=CC(=N1)N1C=2N(CCC1)C(C=C(C2)C2=CC=CC=C2)=O.CC(C)([O-])C.[Na+].C=1C=CC(=CC1)P(C=2C=CC=CC2)C3=CC=C4C=CC=CC4=C3C5=C6C=CC=CC6=CC=C5P(C=7C=CC=CC7)C=8C=CC=CC8.ClC1=NC(=NC=C1)SC.C1(=CC=CC=C1)C=1C=C2N(C(C1)=O)CCN2>>CSC1=NC=CC(=N1)N1CCN2C1=CC(=CC2=O)C2=CC=CC=C2 | O=c1cc(-c2ccccc2)cc2n1CCCN2[c:7]1[cH:6][cH:5][n:4][c:3]([S:2][CH3:1])[n:24]1.[NH:8]1[CH2:9][CH2:10][n:11]2[c:12]1[cH:13][c:14](-[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[cH:21][c:22]2=[O:23]>>[CH3:1][S:2][c:3]1[n:4][cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][n:11]3[c:12]2[cH:13][c:14](-[c:15]2[cH:16][cH:17][cH:18][cH:19... | CSc1nccc(N2CCCn3c2cc(-c2ccccc2)cc3=O)n1.O=c1cc(-c2ccccc2)cc2n1CCN2 | CSc1nccc(N2CCn3c2cc(-c2ccccc2)cc3=O)n1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | e2b33769f44b219d3911e221846a6046a9fb7a29efe4d8dae8fcb782a638ee06 | b1a89fc7d17633bbf5e21d37b95beb5c9a8a0ceb9b07eaaec09195f87467174d | O=c1cc(-c2ccccc2)cc2n1CCN2c1ccncn1 | O=c1:c:c(-c2:c:c:c:c:c:2):c:c2:n:1-C-C-C-N-2-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#16:4]):[#7;a:5]:[c:6]:[c:7]:1.[c:8]:[c:9]1:[#7;a:10](:[c:11])-[C:12]-[C:13]-[NH;D2;+0:14]-1>>[#16:4]-[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:14]2-[C:13]-[C:12]-[#7;a:10](:[c:11]):[c:9]-2:[c:8]):[c:7]:[c:6]:[#7;a:5]:1 | null | [] | null | null | null | null | Following the procedure described for the synthesis of 1-(2-methylsulfanyl-pyrimidin -4-yl)-8-phenyl-1,2,3,4-tetrahydro-pyrido[1,2-a]pyrimidin-6-one, but using 7-phenyl-2,3-dihydro-1H-imidazo[1,2-a]pyridin-5-one (1 g, 4.7 mmol), sodium tert-butoxide (1.26 g, 13.16 mmol), BINAP (0.43 g, 0.7 mmol), Pd (OAc)2 (0.16 g, 0.7... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Tertiary amine | Tertiary amine | c1ccccc1.c1ccn2c(c1)NCCC2.c1cncnc1.c1ccn2c(c1)NCC2 | c1cncnc1.c1ccn2c(c1)NCC2 | c1cncnc1.c1ccn2c(c1)NCC2.c1ccccc1 | HO- | C1(=CC=CC=C1)C | null | null | CSc1nccc(N2CCCn3c2cc(-c2ccccc2)cc3=O)n1.O=c1cc(-c2ccccc2)cc2n1CCN2>C1(=CC=CC=C1)C>CSc1nccc(N2CCn3c2cc(-c2ccccc2)cc3=O)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b0cd299ad92a4b7097196a47ab40341a | Clc1ccnc(Cl)n1.O=c1cc(-c2ccccc2)cc2n1CCN2>>O=c1cc(-c2ccccc2)cc2n1CCN2c1cncc(Cl)n1 | CSC1=NC=CC(=N1)N1CCN2C1=CC(=CC2=O)C2=CC=CC=C2.ClC1=NC(=CC=N1)Cl.C1(=CC=CC=C1)C=1C=C2N(C(C1)=O)CCN2>>ClC1=CN=CC(=N1)N1CCN2C1=CC(=CC2=O)C2=CC=CC=C2 | Cl[c:17]1[n:19][cH:18][cH:20][c:21]([Cl:22])[n:23]1.[O:1]=[c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[cH:11][c:12]2[n:13]1[CH2:14][CH2:15][NH:16]2>>[O:1]=[c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[cH:11][c:12]2[n:13]1[CH2:14][CH2:15][N:16]2[c:17]1[cH:18][n:19][cH:20][c:21]([Cl:22])[n:23]1 | Clc1ccnc(Cl)n1.O=c1cc(-c2ccccc2)cc2n1CCN2 | O=c1cc(-c2ccccc2)cc2n1CCN2c1cncc(Cl)n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 8a5eb1ce9b1cd9e06dadef4c5b5ef114ec706cec868b5a6d8efbea66303ae584 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1cc(-c2ccccc2)cc2n1CCN2c1cnccn1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[cH;D2;+0:5]:[cH;D2;+0:6]:[n;H0;D2;+0:7]:1.[c:8]:[c:9]1:[#7;a:10](:[c:11])-[C:12]-[C:13]-[NH;D2;+0:14]-1>>[Cl;D1;H0:4]-[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:14]2-[C:13]-[C:12]-[#7;a:10](:[c:11]):[c:9]-2:[c:8]):[cH;D2;+0:6]:[n;H0;D2;+0:7]:[cH;D2;+0:5]:1 | null | [] | null | null | null | null | Following the procedure described in the synthesis of 1-(2-methylsulfanyl-pyrimidin -4-yl)-7-phenyl-2,3-dihydro-1H-imidazo[1,2-a]pyridin-5-one, but using 2,6-dichloropyrimidine as the coupling component, 7-phenyl-2,3-dihydro-1H-imidazo[1,2-a]pyridin-5-one (0.5 g, 2.4 mmol) was converted into the title product as a pale... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1cncnc1.c1ccn2c(c1)NCC2 | c1ccn2c(c1)NCC2.c1cnccn1 | c1ccccc1.c1ccn2c(c1)NCC2.c1cnccn1 | HCl | null | null | null | Clc1ccnc(Cl)n1.O=c1cc(-c2ccccc2)cc2n1CCN2>>O=c1cc(-c2ccccc2)cc2n1CCN2c1cncc(Cl)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e7e6c74594c84cb8bade5396c7aa9e05 | NCCc1ccccc1Cl.O=c1cc(-c2ccccc2)cc2n1CCCN2c1ccnc(NCCc2ccccc2)n1>>O=c1cc(-c2ccccc2)cc2n1CCCN2c1ccnc(NCCc2ccccc2Cl)n1 | C(CC1=CC=CC=C1)NC1=NC=CC(=N1)N1C=2N(CCC1)C(C=C(C2)C2=CC=CC=C2)=O.ClC1=C(C=CC=C1)CCN>>ClC1=C(C=CC=C1)CCNC1=NC=CC(=N1)N1C=2N(CCC1)C(C=C(C2)C2=CC=CC=C2)=O | [NH2:23][CH2:24][CH2:25][c:26]1[cH:27][cH:28][cH:29][cH:30][c:31]1[Cl:32].c1ccc(CCN[c:22]2[n:21][cH:20][cH:19][c:18]([N:17]3[c:12]4[cH:11][c:4](-[c:5]5[cH:6][cH:7][cH:8][cH:9][cH:10]5)[cH:3][c:2](=[O:1])[n:13]4[CH2:14][CH2:15][CH2:16]3)[n:33]2)cc1>>[O:1]=[c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[cH:11]... | NCCc1ccccc1Cl.O=c1cc(-c2ccccc2)cc2n1CCCN2c1ccnc(NCCc2ccccc2)n1 | O=c1cc(-c2ccccc2)cc2n1CCCN2c1ccnc(NCCc2ccccc2Cl)n1 | null | null | null | Heteroatom Alkylation and Arylation | Chlorination | 2869fd0770195ad0aa4896cefd4a8639a5d167b5b710a52d5851c30184610240 | 56c236df53b2bac39dd5009577ad83355284f0665c6e7906bf125e9599e48527 | O=c1cc(-c2ccccc2)cc2n1CCCN2c1ccnc(NCCc2ccccc2)n1 | [C:1]-[C:2]-[NH2;D1;+0:3].[c:4]:[#7;a:5]:[c;H0;D3;+0:6](-N-C-C-c1:c:c:c:c:c:1):[#7;a:7]:[c:8]>>[C:1]-[C:2]-[NH;D2;+0:3]-[c;H0;D3;+0:6](:[#7;a:7]:[c:8]):[#7;a:5]:[c:4] | null | [] | null | null | null | null | Followed the same procedure described for the synthesis of 1-(2-phenethylamino-pyrimidin-4-yl)-8-phenyl-1,2,3,4-tetrahydro -pyrido[1,2-a]pyrimidin-6-one, the sulfoxide (0.22 g, 0.6 mmol) was displaced with 2-(2-chlorophenyl)ethylamine (0.25 mL, 1.8 mmol) to give the title compound as a yellow solid. MS m/e 458 (M+H)+.
... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine | Secondary amine | c1ccccc1.c1cncnc1 | c1cncnc1 | c1ccccc1.c1ccn2c(c1)NCCC2.c1cncnc1.c1ccccc1 | Other | null | null | null | NCCc1ccccc1Cl.O=c1cc(-c2ccccc2)cc2n1CCCN2c1ccnc(NCCc2ccccc2)n1>>O=c1cc(-c2ccccc2)cc2n1CCCN2c1ccnc(NCCc2ccccc2Cl)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0c92194a3bb043a390e449a7f49338dd | NCCc1c(Cl)cccc1Cl.O=c1cc(-c2ccccc2)cc2n1CCCN2c1ccnc(NCCc2ccccc2)n1>>O=c1cc(-c2ccccc2)cc2n1CCCN2c1ccnc(NCCc2c(Cl)cccc2Cl)n1 | C(CC1=CC=CC=C1)NC1=NC=CC(=N1)N1C=2N(CCC1)C(C=C(C2)C2=CC=CC=C2)=O.ClC1=C(C(=CC=C1)Cl)CCN>>ClC1=C(C(=CC=C1)Cl)CCNC1=NC=CC(=N1)N1C=2N(CCC1)C(C=C(C2)C2=CC=CC=C2)=O | NCC[c:26]1[c:27]([Cl:28])[cH:29][cH:30][cH:31][c:32]1[Cl:33].c1ccc([CH2:25][CH2:24][NH:23][c:22]2[n:21][cH:20][cH:19][c:18]([N:17]3[c:12]4[cH:11][c:4](-[c:5]5[cH:6][cH:7][cH:8][cH:9][cH:10]5)[cH:3][c:2](=[O:1])[n:13]4[CH2:14][CH2:15][CH2:16]3)[n:34]2)cc1>>[O:1]=[c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)... | NCCc1c(Cl)cccc1Cl.O=c1cc(-c2ccccc2)cc2n1CCCN2c1ccnc(NCCc2ccccc2)n1 | O=c1cc(-c2ccccc2)cc2n1CCCN2c1ccnc(NCCc2c(Cl)cccc2Cl)n1 | null | null | null | C-C Coupling | OtherReaction | 4be5bc10b11730334b74b64301940b91623d7d2ecad7d43a0b952417d4e4e375 | b4142dbc8aebf8ea5ecf50af61f2215c729ea5a2dcf1f9e7fd52e13ad01c499d | O=c1cc(-c2ccccc2)cc2n1CCCN2c1ccnc(NCCc2ccccc2)n1 | N-C-C-[c;H0;D3;+0:1](:[c:2](-[Cl;D1;H0:3]):[c:4]):[c:5](-[Cl;D1;H0:6]):[c:7].[#7:8]-[C:9]-[CH2;D2;+0:10]-c1:c:c:c:c:c:1>>[#7:8]-[C:9]-[CH2;D2;+0:10]-[c;H0;D3;+0:1](:[c:2](-[Cl;D1;H0:3]):[c:4]):[c:5](-[Cl;D1;H0:6]):[c:7] | null | [] | null | null | null | null | Followed the same procedure described for the synthesis of 1-(2-phenethylamino-pyrimidin-4-yl)-8-phenyl-1,2,3,4-tetrahydro -pyrido[1,2-a]pyrimidin-6-one, the sulfoxide (0.1 g, 0.27 mmol) was displaced with 2-(2,6-dichlorophenyl)ethylamine (0.16 g, 0.82 mmol) to give the title compound as a yellow solid. MS m/e 492 (M+H... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccn2c(c1)NCCC2.c1cncnc1.c1ccccc1 | Other | null | null | null | NCCc1c(Cl)cccc1Cl.O=c1cc(-c2ccccc2)cc2n1CCCN2c1ccnc(NCCc2ccccc2)n1>>O=c1cc(-c2ccccc2)cc2n1CCCN2c1ccnc(NCCc2c(Cl)cccc2Cl)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-04477d4233fe48f89bed229349edc82b | NCCc1ccc(Cl)cc1Cl.O=c1cc(-c2ccccc2)cc2n1CCCN2c1ccnc(NCCc2ccccc2)n1>>O=c1cc(-c2ccccc2)cc2n1CCCN2c1ccnc(NCCc2ccc(Cl)cc2Cl)n1 | C(CC1=CC=CC=C1)NC1=NC=CC(=N1)N1C=2N(CCC1)C(C=C(C2)C2=CC=CC=C2)=O.ClC1=C(C=CC(=C1)Cl)CCN>>ClC1=C(C=CC(=C1)Cl)CCNC1=NC=CC(=N1)N1C=2N(CCC1)C(C=C(C2)C2=CC=CC=C2)=O | NCC[c:26]1[cH:27][cH:28][c:29]([Cl:30])[cH:31][c:32]1[Cl:33].c1ccc([CH2:25][CH2:24][NH:23][c:22]2[n:21][cH:20][cH:19][c:18]([N:17]3[c:12]4[cH:11][c:4](-[c:5]5[cH:6][cH:7][cH:8][cH:9][cH:10]5)[cH:3][c:2](=[O:1])[n:13]4[CH2:14][CH2:15][CH2:16]3)[n:34]2)cc1>>[O:1]=[c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)... | NCCc1ccc(Cl)cc1Cl.O=c1cc(-c2ccccc2)cc2n1CCCN2c1ccnc(NCCc2ccccc2)n1 | O=c1cc(-c2ccccc2)cc2n1CCCN2c1ccnc(NCCc2ccc(Cl)cc2Cl)n1 | null | null | null | C-C Coupling | OtherReaction | 4be5bc10b11730334b74b64301940b91623d7d2ecad7d43a0b952417d4e4e375 | b4142dbc8aebf8ea5ecf50af61f2215c729ea5a2dcf1f9e7fd52e13ad01c499d | O=c1cc(-c2ccccc2)cc2n1CCCN2c1ccnc(NCCc2ccccc2)n1 | N-C-C-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6].[#7:7]-[C:8]-[CH2;D2;+0:9]-c1:c:c:c:c:c:1>>[#7:7]-[C:8]-[CH2;D2;+0:9]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6] | null | [] | null | null | null | null | Followed the same procedure in the synthesis of 1-(2-phenethylamino-pyrimidin-4-yl)-8-phenyl-1,2,3,4-tetrahydro-pyrido[1,2-a]pyrimidin-6-one, the sulfoxide (0.11 g, 0.3 mmol) was displaced with 2-(2,4-dichlorophenyl)ethylamine (0.14 mL, 0.9 mmol) to give the title compound as a yellow solid. MS m/e 492 (M+H)+.
Conditio... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccn2c(c1)NCCC2.c1cncnc1.c1ccccc1 | Other | null | null | null | NCCc1ccc(Cl)cc1Cl.O=c1cc(-c2ccccc2)cc2n1CCCN2c1ccnc(NCCc2ccccc2)n1>>O=c1cc(-c2ccccc2)cc2n1CCCN2c1ccnc(NCCc2ccc(Cl)cc2Cl)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ad8f2b2f8d6f40b8b539a6bde61a85d7 | CC(N)Cc1cccc(CO)c1.O=c1cc(-c2ccccc2)cc2n1CCCN2c1ccnc(NCCc2ccccc2)n1>>CC(Cc1cccc(CO)c1)Nc1nccc(N2CCCn3c2cc(-c2ccccc2)cc3=O)n1 | C(CC1=CC=CC=C1)NC1=NC=CC(=N1)N1C=2N(CCC1)C(C=C(C2)C2=CC=CC=C2)=O.NC(CC=1C=C(C=CC1)CO)C>>OCC=1C=C(C=CC1)CC(C)NC1=NC=CC(=N1)N1C=2N(CCC1)C(C=C(C2)C2=CC=CC=C2)=O | [CH3:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([CH2:9][OH:10])[cH:11]1)[NH2:12].c1ccc(CCN[c:13]2[n:14][cH:15][cH:16][c:17]([N:18]3[CH2:19][CH2:20][CH2:21][n:22]4[c:23]3[cH:24][c:25](-[c:26]3[cH:27][cH:28][cH:29][cH:30][cH:31]3)[cH:32][c:33]4=[O:34])[n:35]2)cc1>>[CH3:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([CH... | CC(N)Cc1cccc(CO)c1.O=c1cc(-c2ccccc2)cc2n1CCCN2c1ccnc(NCCc2ccccc2)n1 | CC(Cc1cccc(CO)c1)Nc1nccc(N2CCCn3c2cc(-c2ccccc2)cc3=O)n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 2869fd0770195ad0aa4896cefd4a8639a5d167b5b710a52d5851c30184610240 | 56c236df53b2bac39dd5009577ad83355284f0665c6e7906bf125e9599e48527 | O=c1cc(-c2ccccc2)cc2n1CCCN2c1ccnc(NCCc2ccccc2)n1 | [C:1]-[C:2](-[C;D1;H3:3])-[NH2;D1;+0:4].[c:5]:[#7;a:6]:[c;H0;D3;+0:7](-N-C-C-c1:c:c:c:c:c:1):[#7;a:8]:[c:9]>>[C:1]-[C:2](-[C;D1;H3:3])-[NH;D2;+0:4]-[c;H0;D3;+0:7](:[#7;a:6]:[c:5]):[#7;a:8]:[c:9] | null | [] | null | null | null | null | Following the same procedure described for the synthesis of 1-(2-phenethylamino-pyrimidin-4-yl)-8-phenyl -1,2,3,4-tetrahydro-pyrido[1,2-a]pyrimidin-6-one, the sulfoxide (0.29 g, 0.83 mmol) was displaced with [3-(2-amino-propyl)-phenyl]-methanol (0.3 g, 1.66 mmol) to give the title compound as a light yellow solid. MS m... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine | Secondary amine | c1ccccc1.c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccn2c(c1)NCCC2.c1ccccc1 | Other | null | null | null | CC(N)Cc1cccc(CO)c1.O=c1cc(-c2ccccc2)cc2n1CCCN2c1ccnc(NCCc2ccccc2)n1>>CC(Cc1cccc(CO)c1)Nc1nccc(N2CCCn3c2cc(-c2ccccc2)cc3=O)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b2f3937799494752b8fbf7e0af1f7829 | NCCc1ccccc1.O=c1cc(-c2ccccc2)cc2n1CCCN2c1cc(Cl)ncn1>>O=c1cc(-c2ccccc2)cc2n1CCCN2c1cc(NCCc2ccccc2)ncn1 | ClC1=CC(=NC=N1)N1C=2N(CCC1)C(C=C(C2)C2=CC=CC=C2)=O.C(=O)([O-])[O-].[K+].[K+].C(CC1=CC=CC=C1)N>>C(CC1=CC=CC=C1)NC1=CC(=NC=N1)N1C=2N(CCC1)C(C=C(C2)C2=CC=CC=C2)=O | [NH2:21][CH2:22][CH2:23][c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1.Cl[c:20]1[cH:19][c:18]([N:17]2[c:12]3[cH:11][c:4](-[c:5]4[cH:6][cH:7][cH:8][cH:9][cH:10]4)[cH:3][c:2](=[O:1])[n:13]3[CH2:14][CH2:15][CH2:16]2)[n:32][cH:31][n:30]1>>[O:1]=[c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[cH:11][c:12]2[n:13]1[CH... | NCCc1ccccc1.O=c1cc(-c2ccccc2)cc2n1CCCN2c1cc(Cl)ncn1 | O=c1cc(-c2ccccc2)cc2n1CCCN2c1cc(NCCc2ccccc2)ncn1 | null | null | O.CN(C)C=O.CCOC(=O)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1cc(-c2ccccc2)cc2n1CCCN2c1cc(NCCc2ccccc2)ncn1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]):[c:7]:1.[C:8]-[C:9]-[NH2;D1;+0:10]>>[#7:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[C:9]-[C:8]):[c:7]:1 | null | [] | null | null | null | null | To a stirred mixture of 1-(6-chloro-pyrimidin-4-yl)-8-phenyl -1,2,3,4-tetrahydro-pyrido[1,2-a]pyrimidin-6-one (0.158 mg, 0.47 mmol) and excess of K2CO3 in DMF (3 mL) was added phenethylamine (0.15 mL, 1.2 mmol). The overall reaction vessel was irradiated under microwave conditions at 150° C. for 10 min. After diluted w... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1ccn2c(c1)NCCC2.c1cncnc1.c1ccccc1 | HCl | O.CN(C)C=O.CCOC(=O)C | null | null | NCCc1ccccc1.O=c1cc(-c2ccccc2)cc2n1CCCN2c1cc(Cl)ncn1>O.CN(C)C=O.CCOC(=O)C>O=c1cc(-c2ccccc2)cc2n1CCCN2c1cc(NCCc2ccccc2)ncn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cb6bf0074c9b43fd9e0c98dcafb44ec9 | NCCc1ccccc1Cl.O=c1cc(-c2ccccc2)cc2n1CCCN2c1cc(Cl)ncn1>>O=c1cc(-c2ccccc2)cc2n1CCCN2c1cc(NCCc2ccccc2Cl)ncn1 | C(CC1=CC=CC=C1)NC1=NC=CC(=N1)N1C=2N(CCC1)C(C=C(C2)C2=CC=CC=C2)=O.ClC1=CC(=NC=N1)N1C=2N(CCC1)C(C=C(C2)C2=CC=CC=C2)=O.ClC1=C(C=CC=C1)CCN>>ClC1=C(C=CC=C1)CCNC1=CC(=NC=N1)N1C=2N(CCC1)C(C=C(C2)C2=CC=CC=C2)=O | [NH2:21][CH2:22][CH2:23][c:24]1[cH:25][cH:26][cH:27][cH:28][c:29]1[Cl:30].Cl[c:20]1[cH:19][c:18]([N:17]2[c:12]3[cH:11][c:4](-[c:5]4[cH:6][cH:7][cH:8][cH:9][cH:10]4)[cH:3][c:2](=[O:1])[n:13]3[CH2:14][CH2:15][CH2:16]2)[n:33][cH:32][n:31]1>>[O:1]=[c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[cH:11][c:12]2[n:1... | NCCc1ccccc1Cl.O=c1cc(-c2ccccc2)cc2n1CCCN2c1cc(Cl)ncn1 | O=c1cc(-c2ccccc2)cc2n1CCCN2c1cc(NCCc2ccccc2Cl)ncn1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1cc(-c2ccccc2)cc2n1CCCN2c1cc(NCCc2ccccc2)ncn1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]):[c:7]:1.[C:8]-[C:9]-[NH2;D1;+0:10]>>[#7:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[C:9]-[C:8]):[c:7]:1 | null | [] | null | null | null | null | Followed the same procedure described for the synthesis of 1-(2-phenethylamino-pyrimidin-4-yl)-8-phenyl-1,2,3,4-tetrahydro -pyrido[1,2-a]pyrimidin-6-one, 1-(6-chloro-pyrimidin-4-yl)-8-phenyl-1,2,3,4-tetrahydro -pyrido[1,2-a]pyrimidin-6-one (0.136 g, 0.40 mmol) was reacted with 2-(2-chlorophenyl)ethylamine (0.17 mL, 1.2... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1ccn2c(c1)NCCC2.c1cncnc1.c1ccccc1 | HCl | null | null | null | NCCc1ccccc1Cl.O=c1cc(-c2ccccc2)cc2n1CCCN2c1cc(Cl)ncn1>>O=c1cc(-c2ccccc2)cc2n1CCCN2c1cc(NCCc2ccccc2Cl)ncn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-34f352eead4448779d7bf3a6aa2543d9 | CC(N)Cc1cccc(CO)c1.O=c1cc(-c2ccccc2)cc2n1CCCN2c1ccnc(NCCc2ccccc2)n1>>CC(Cc1cccc(CO)c1)Nc1nccc(N2CCn3c2cc(-c2ccccc2)cc3=O)n1 | C(CC1=CC=CC=C1)NC1=NC=CC(=N1)N1C=2N(CCC1)C(C=C(C2)C2=CC=CC=C2)=O.NC(CC=1C=C(C=CC1)CO)C>>OCC=1C=C(C=CC1)CC(C)NC1=NC=CC(=N1)N1CCN2C1=CC(=CC2=O)C2=CC=CC=C2 | [CH3:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([CH2:9][OH:10])[cH:11]1)[NH2:12].c1ccc(CCN[c:13]2[n:14][cH:15][cH:16][c:17]([N:18]3C[CH2:19][CH2:20][n:21]4[c:22]3[cH:23][c:24](-[c:25]3[cH:26][cH:27][cH:28][cH:29][cH:30]3)[cH:31][c:32]4=[O:33])[n:34]2)cc1>>[CH3:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([CH2:9][OH... | CC(N)Cc1cccc(CO)c1.O=c1cc(-c2ccccc2)cc2n1CCCN2c1ccnc(NCCc2ccccc2)n1 | CC(Cc1cccc(CO)c1)Nc1nccc(N2CCn3c2cc(-c2ccccc2)cc3=O)n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 007c6555f8bdc87d89d912e2e910a62cdfe7700b1bcfac6f6083df140cad2f82 | fb80d3c6b41d3e084e190e67a9fe6319222a14054de6c86adc01f47a0c5fc4e1 | O=c1cc(-c2ccccc2)cc2n1CCN2c1ccnc(NCCc2ccccc2)n1 | [C:1]-[C:2](-[C;D1;H3:3])-[NH2;D1;+0:4].[c:5]:[c:6]1:[#7;a:7](:[c:8])-[C:9]-[CH2;D2;+0:10]-C-[N;H0;D3;+0:11]-1-[c:12]1:[#7;a:13]:[c;H0;D3;+0:14](-N-C-C-c2:c:c:c:c:c:2):[#7;a:15]:[c:16]:[c:17]:1>>[C:1]-[C:2](-[C;D1;H3:3])-[NH;D2;+0:4]-[c;H0;D3;+0:14]1:[#7;a:15]:[c:16]:[c:17]:[c:12](-[N;H0;D3;+0:11]2-[CH2;D2;+0:10]-[C:9]... | null | [] | null | null | null | null | Following the same procedure described for the synthesis of 1-(2-phenethylamino-pyrimidin-4-yl)-8-phenyl-1,2,3,4-tetrahydro-pyrido[1,2-a]pyrimidin-6-one, the sulfoxide/sulfone (0.4 g) was displaced with [3-(2-amino-propyl)-phenyl]-methanol (1.2 eq) to give the title compound as a light yellow solid. MS m/e 454 (M+H)+.
... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine.Tertiary amine | Secondary amine.Tertiary amine | c1ccccc1.c1cncnc1.c1ccn2c(c1)NCCC2 | c1cncnc1.c1ccn2c(c1)NCC2 | c1ccccc1.c1cncnc1.c1ccn2c(c1)NCC2.c1ccccc1 | Other | null | null | null | CC(N)Cc1cccc(CO)c1.O=c1cc(-c2ccccc2)cc2n1CCCN2c1ccnc(NCCc2ccccc2)n1>>CC(Cc1cccc(CO)c1)Nc1nccc(N2CCn3c2cc(-c2ccccc2)cc3=O)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ba1c8c7437684ce38dd842cb5b96d860 | NCCc1ccccc1.O=c1cc(-c2ccccc2)cc2n1CCN2c1cncc(Cl)n1>>O=c1cc(-c2ccccc2)cc2n1CCN2c1cncc(NCCc2ccccc2)n1 | C(CC1=CC=CC=C1)N.ClC1=CN=CC(=N1)N1CCN2C1=CC(=CC2=O)C2=CC=CC=C2.CC(C)([O-])C.[Na+].C=1C=CC(=CC1)P(C=2C=CC=CC2)C3=CC=C4C=CC=CC4=C3C5=C6C=CC=CC6=CC=C5P(C=7C=CC=CC7)C=8C=CC=CC8>>C(CC1=CC=CC=C1)NC1=CN=CC(=N1)N1CCN2C1=CC(=CC2=O)C2=CC=CC=C2 | [NH2:22][CH2:23][CH2:24][c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1.Cl[c:21]1[cH:20][n:19][cH:18][c:17]([N:16]2[c:12]3[cH:11][c:4](-[c:5]4[cH:6][cH:7][cH:8][cH:9][cH:10]4)[cH:3][c:2](=[O:1])[n:13]3[CH2:14][CH2:15]2)[n:31]1>>[O:1]=[c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[cH:11][c:12]2[n:13]1[CH2:14][CH... | NCCc1ccccc1.O=c1cc(-c2ccccc2)cc2n1CCN2c1cncc(Cl)n1 | O=c1cc(-c2ccccc2)cc2n1CCN2c1cncc(NCCc2ccccc2)n1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | d8d76a4347a32a5acf79894f48887cf8d745ba4ca5f91e54084ebdbe25f43c75 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1cc(-c2ccccc2)cc2n1CCN2c1cncc(NCCc2ccccc2)n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1 | null | [] | 70 | CELSIUS | null | null | To a mixture of 1-(6-chloro-pyrazin-2-yl)-7-phenyl-2,3-dihydro-1H-imidazo[1,2-a]pyridin-5-one (85 mg, 0.26 mmol), sodium tert-butoxide (70 mg, 2.8 eq), BINAP (24 mg, 15% eq), and Pd (OAc)2 (9 mg, 15% eq) was added toluene (5 mL) and phenethylamine (39 μL, 1.2 eq). After purged with N2 for 10 min, the overall mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cnccn1 | c1cnccn1 | c1ccccc1.c1ccn2c(c1)NCC2.c1cnccn1.c1ccccc1 | HCl | C1(=CC=CC=C1)C | 70 | null | NCCc1ccccc1.O=c1cc(-c2ccccc2)cc2n1CCN2c1cncc(Cl)n1>C1(=CC=CC=C1)C>O=c1cc(-c2ccccc2)cc2n1CCN2c1cncc(NCCc2ccccc2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ebeeb039964a4f5b90012c8ce5c1b9a9 | CCOC(=O)CBr.c1ccc(CNNCc2ccccc2)cc1>>NCC(=O)O.c1ccc(CNNCc2ccccc2)cc1 | BrCC(=O)OCC.C(C1=CC=CC=C1)NNCC1=CC=CC=C1.C1CCOC1.BrCC(=O)OCC>>NCC(=O)O.C(C1=CC=CC=C1)NNCC1=CC=CC=C1 | CC[O:5][C:3]([CH2:2]Br)=[O:4].[NH:1]([CH2:10][c:9]1[cH:8][cH:7][cH:6][cH:21][cH:20]1)[NH:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[NH2:1][CH2:2][C:3](=[O:4])[OH:5].[cH:6]1[cH:7][cH:8][c:9]([CH2:10][NH:11][NH:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[cH:20][cH:21]1 | CCOC(=O)CBr.c1ccc(CNNCc2ccccc2)cc1 | NCC(=O)O.c1ccc(CNNCc2ccccc2)cc1 | null | CCCC[N+](CCCC)(CCCC)CCCC.[I-] | CCN(CC)CC | Heteroatom Alkylation and Arylation | OtherReaction | 75da99c5c8d92cc69676755c7566deba3a404ac4d1c9feac0426623d6ce52991 | da708edba4837b1998751e9cba8b74e9330f39096dc25117914a4af61948a33f | c1ccc(CNNCc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-C-C.[c:5]-[C:6]-[NH;D2;+0:7]-[NH;D2;+0:8]-[CH2;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[NH2;D1;+0:8]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4].[c:5]-[C:6]-[NH;D2;+0:7]-[#7:13]-[CH2;D2;+0:9]-[c:10](:[c:11]):[c:12] | 97 | [{"value": 97.0, "product": "NCC(=O)O.C(C1=CC=CC=C1)NNCC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 7 | HOUR | To a solution of dibenzylhydrazine (5.30 g, 25.0 mmol) and THF (50 mL) and TBAI (0.46 g, 1.25 mmol) was added BrCH2CO2Et (2.64 mL, 23.8 mmol) and Et3N (3.32 mL, 23.8 mmol). The reaction mixture was stirred at 60° C. for 7 hours, an additional 0.3 eq. of base and electrophile were added (BrCH2CO2Et, 0.83 mL, 7.5 mmol an... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Primary halide.Ester | Hydrazine.Carboxylic acid.Primary amine | null | null | c1ccccc1.c1ccccc1 | HBr | CCCC[N+](CCCC)(CCCC)CCCC.[I-].CCN(CC)CC | 60 | 7 | CCOC(=O)CBr.c1ccc(CNNCc2ccccc2)cc1>CCCC[N+](CCCC)(CCCC)CCCC.[I-].CCN(CC)CC>NCC(=O)O.c1ccc(CNNCc2ccccc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0af8c32461614a67a44ada3a3898c093 | CCOC(=O)c1sc(Cl)nc1-c1ccccc1.COc1cc2nc[nH]c2cc1OC>>CCOC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1-c1ccccc1 | O.COC1=CC2=C(N=CN2)C=C1OC.[H-].[Na+].C(C)OC(=O)C1=C(N=C(S1)Cl)C1=CC=CC=C1>>C(C)OC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)C2=CC=CC=C2 | Cl[c:8]1[s:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:23](-[c:24]2[cH:25][cH:26][cH:27][cH:28][cH:29]2)[n:22]1.[nH:9]1[cH:10][n:11][c:12]2[cH:13][c:14]([O:15][CH3:16])[c:17]([O:18][CH3:19])[cH:20][c:21]12>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[s:7][c:8](-[n:9]2[cH:10][n:11][c:12]3[cH:13][c:14]([O:15][CH3:16])[c:17]([... | CCOC(=O)c1sc(Cl)nc1-c1ccccc1.COc1cc2nc[nH]c2cc1OC | CCOC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1-c1ccccc1 | null | null | CN1CCCC1=O | Heteroatom Alkylation and Arylation | OtherReaction | b38f76237cdec2baf41c9411839797fed979828e4dd9354fb2aa8a56efaef6ba | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc(-c2csc(-n3cnc4ccccc43)n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[C:4](-[#8:5])=[O;D1;H0:6]):[c:7]:[#7;a:8]:1.[c:9]:[c:10]1:[#7;a:11]:[c:12]:[nH;D2;+0:13]:[c:14]:1:[c:15]>>[#8:5]-[C:4](=[O;D1;H0:6])-[c:3]1:[#16;a:2]:[c;H0;D3;+0:1](-[n;H0;D3;+0:13]2:[c:12]:[#7;a:11]:[c:10](:[c:9]):[c:14]:2:[c:15]):[#7;a:8]:[c:7]:1 | 84 | [{"value": 84.0, "product": "C(C)OC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.6, "product": "C(C)OC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | 5,6-Dimethoxybenzimidazole (470 mg, 2.64 mmol) was added to a suspension of NaH (60% in mineral oil, 112 mg, 2.8 mmol) in NMP (5 ml) at <5° C. The mixture was stirred for 20 min, then a solution of 2-chloro-4-phenylthiazole-5-carboxylic acid ethyl ester (589 mg, 2.2 mmol) in NMP (1.5 ml) was added over 2-3 min. The mix... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cscn1.c1ccc2[nH]cnc2c1 | c1cscn1.c1ccc2[nH]cnc2c1 | c1cscn1.c1ccc2[nH]cnc2c1.c1ccccc1 | HCl | CN1CCCC1=O | null | 0.333333 | CCOC(=O)c1sc(Cl)nc1-c1ccccc1.COc1cc2nc[nH]c2cc1OC>CN1CCCC1=O>CCOC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1-c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c9ff6485c25c4a798f1ff4bd86c8e00b | CCOC(=O)c1sc(Cl)nc1-c1ccccc1.c1ccc2[nH]cnc2c1>>CCOC(=O)c1sc(-n2cnc3ccccc32)nc1-c1ccccc1 | O.C(C)OC(=O)C1=C(N=C(S1)Cl)C1=CC=CC=C1.N1=CNC2=C1C=CC=C2.[Li]N([Si](C)(C)C)[Si](C)(C)C>>C(C)OC(=O)C1=C(N=C(S1)N1C=NC2=C1C=CC=C2)C2=CC=CC=C2 | Cl[c:8]1[s:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:19](-[c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[n:18]1.[nH:9]1[cH:10][n:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[s:7][c:8](-[n:9]2[cH:10][n:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]23)[n:18][c:19]1-[c:20]1[cH:21][c... | CCOC(=O)c1sc(Cl)nc1-c1ccccc1.c1ccc2[nH]cnc2c1 | CCOC(=O)c1sc(-n2cnc3ccccc32)nc1-c1ccccc1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | b38f76237cdec2baf41c9411839797fed979828e4dd9354fb2aa8a56efaef6ba | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc(-c2csc(-n3cnc4ccccc43)n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[C:4](-[#8:5])=[O;D1;H0:6]):[c:7]:[#7;a:8]:1.[c:9]:[c:10]1:[#7;a:11]:[c:12]:[nH;D2;+0:13]:[c:14]:1:[c:15]>>[#8:5]-[C:4](=[O;D1;H0:6])-[c:3]1:[#16;a:2]:[c;H0;D3;+0:1](-[n;H0;D3;+0:13]2:[c:12]:[#7;a:11]:[c:10](:[c:9]):[c:14]:2:[c:15]):[#7;a:8]:[c:7]:1 | 61.8 | [{"value": 61.0, "product": "C(C)OC(=O)C1=C(N=C(S1)N1C=NC2=C1C=CC=C2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.8, "product": "C(C)OC(=O)C1=C(N=C(S1)N1C=NC2=C1C=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | A mixture of 2-chloro-4-phenylthiazole-5-carboxylic acid ethyl ester (134 mg, 0.5 mmol), benzimidazole (Aldrich) (73.8 mg, 0.625 mmol) and LiN(TMS)2 (1N tetrahydrofuran solution, 0.63 ml) in tetrahydrofuran (2 ml) was heated in a micro-wave oven at 120° C. for 30 min. Water (3 ml) was added and the mixture was filtered... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cscn1.c1ccc2[nH]cnc2c1 | c1cscn1.c1ccc2[nH]cnc2c1 | c1cscn1.c1ccc2[nH]cnc2c1.c1ccccc1 | HCl | O1CCCC1 | 120 | null | CCOC(=O)c1sc(Cl)nc1-c1ccccc1.c1ccc2[nH]cnc2c1>O1CCCC1>CCOC(=O)c1sc(-n2cnc3ccccc32)nc1-c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a21b61bc535644b9b17a1f6bd9ccfbba | O=Cc1sc(Br)nc1Br.[O]=[Mn](=[O])(=[O])[O-]>>O=C(O)c1sc(Br)nc1Br | [Mn](=O)(=O)(=O)[O-].[K+].BrC=1SC(=C(N1)Br)C=O.[Mn](=O)(=O)(=O)[O-].[K+]>>BrC=1SC(=C(N1)Br)C(=O)O | [O:1]=[CH:2][c:4]1[s:5][c:6]([Br:7])[n:8][c:9]1[Br:10].[O]=[Mn](=[O])(=[O])[O-:3]>>[O:1]=[C:2]([OH:3])[c:4]1[s:5][c:6]([Br:7])[n:8][c:9]1[Br:10] | O=Cc1sc(Br)nc1Br.[O]=[Mn](=[O])(=[O])[O-] | O=C(O)c1sc(Br)nc1Br | null | null | O | Acylation | OtherReaction | 212580cf94343ba681451fe636f6c4d850d6e10e1bdc7e1852b33ddb4cd6898f | 37c4d4a9954dede23d940a212db876610ae18deb2faf143c8b44e17692b9193f | c1cscn1 | [Br;D1;H0:1]-[c:2]1:[#7;a:3]:[c:4]:[#16;a:5]:[c:6]:1-[CH;D2;+0:7]=[O;D1;H0:8].[O-;H0;D1:9]-[Mn](=[O])(=[O])=[O]>>[Br;D1;H0:1]-[c:2]1:[#7;a:3]:[c:4]:[#16;a:5]:[c:6]:1-[C;H0;D3;+0:7](=[O;D1;H0:8])-[OH;D1;+0:9] | null | [] | null | null | null | null | Solid potassium permanganate (2.19 g, 13.85 mmol) was added portionwise to a hot suspension of 2,4-dibromo-thiazole-5-carbaldehyde (2.5 g, 9.23 mmol) in water (20 ml). The progress of the reaction was monitored by HPLC. More potassium permanganate was added until all of the aldehyde was consumed. The dark suspension wa... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Carboxylic acid | null | null | c1cscn1 | Other | O | null | null | O=Cc1sc(Br)nc1Br.[O]=[Mn](=[O])(=[O])[O-]>O>O=C(O)c1sc(Br)nc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6af32ca2635141ed8b014e6444daca2b | O=C(O)c1sc(Br)nc1Br>>COC(=O)c1sc(Br)nc1Br | BrC=1SC(=C(N1)Br)C(=O)O.CN(CCCN=C=NCC)C>>COC(=O)C1=C(N=C(S1)Br)Br | [OH:2][C:3](=[O:4])[c:5]1[s:6][c:7]([Br:8])[n:9][c:10]1[Br:11]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[s:6][c:7]([Br:8])[n:9][c:10]1[Br:11] | O=C(O)c1sc(Br)nc1Br | COC(=O)c1sc(Br)nc1Br | null | null | CO | Miscellaneous | Protection of carboxylic acid | 56520e0abb4535dce9a663824ca803b71c2c0dd72dfd246317d953596a987bd2 | 2ccc7a30191c2c171b49e8a0217bee87430687dd0f567141eca025a75b7e3136 | c1cscn1 | [#16;a:1]:[c:2](-[C:3](=[O;D1;H0:4])-[OH;D1;+0:5]):[c:6]:[#7;a:7]>>[#16;a:1]:[c:2](-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[C;D1;H3:8]):[c:6]:[#7;a:7] | 78.6 | [{"value": 78.0, "product": "COC(=O)C1=C(N=C(S1)Br)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.6, "product": "COC(=O)C1=C(N=C(S1)Br)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of 2,4-dibromo-thiazole-5-carboxylic acid (1.7 g, 5.92 mmol) in methanol (20 ml) was treated with N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (920 mg, 5.92 mmol). The mixture was stirred at ambient temperature overnight. The solvent was evaporated and water (30 ml) was added. The mixture was then extracte... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | c1cscn1 | Other | CO | null | 8 | O=C(O)c1sc(Br)nc1Br>CO>COC(=O)c1sc(Br)nc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-342d8b1c96644769bb9b2301fe33859a | COC(=O)c1sc(Br)nc1Br.COc1cc2nc[nH]c2cc1OC>>COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br | O.COC(=O)C1=C(N=C(S1)Br)Br.COC1=CC2=C(NC=N2)C=C1OC.[H-].[Na+]>>COC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)Br | Br[c:7]1[s:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:22]([Br:23])[n:21]1.[nH:8]1[cH:9][n:10][c:11]2[cH:12][c:13]([O:14][CH3:15])[c:16]([O:17][CH3:18])[cH:19][c:20]12>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[s:6][c:7](-[n:8]2[cH:9][n:10][c:11]3[cH:12][c:13]([O:14][CH3:15])[c:16]([O:17][CH3:18])[cH:19][c:20]23)[n:21][c:22]1[Br:23] | COC(=O)c1sc(Br)nc1Br.COc1cc2nc[nH]c2cc1OC | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br | null | null | CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | OtherReaction | b38f76237cdec2baf41c9411839797fed979828e4dd9354fb2aa8a56efaef6ba | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc2c(c1)ncn2-c1nccs1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[C:4](-[#8:5])=[O;D1;H0:6]):[c:7]:[#7;a:8]:1.[c:9]:[c:10]1:[#7;a:11]:[c:12]:[nH;D2;+0:13]:[c:14]:1:[c:15]>>[#8:5]-[C:4](=[O;D1;H0:6])-[c:3]1:[#16;a:2]:[c;H0;D3;+0:1](-[n;H0;D3;+0:13]2:[c:12]:[#7;a:11]:[c:10](:[c:9]):[c:14]:2:[c:15]):[#7;a:8]:[c:7]:1 | 73 | [{"value": 73.0, "product": "COC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.1, "product": "COC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 5,6-Dimethoxy-1H-benzimidazole (1.0 g, 5.65 mmol) in 1-methyl-2-pyrrolidinone (10 ml) at 0° C. was added NaH (60% dispersion; 339 mg, 8.475 mmol). After gas evolution had stopped, 2,4-Dibromo-thiazole-5-carboxylic acid methyl ester (1.7 g, 5.65 mmol) was added. The resulting solution was stirred at amb... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cscn1.c1ccc2[nH]cnc2c1 | c1cscn1.c1ccc2[nH]cnc2c1 | c1cscn1.c1ccc2[nH]cnc2c1 | HBr | CN1C(CCC1)=O | null | 1 | COC(=O)c1sc(Br)nc1Br.COc1cc2nc[nH]c2cc1OC>CN1C(CCC1)=O>COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8df2b2f2ab9843b1ad9a8483dab5bafd | CCOC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1-c1ccccc1>>COc1cc2ncn(-c3nc(-c4ccccc4)c(C(=O)O)s3)c2cc1OC | C(C)OC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)C2=CC=CC=C2.[OH-].[Na+].O>>COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC=CC=C2)C(=O)O)C=C1OC | CC[O:21][C:19]([c:18]1[c:11](-[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[n:10][c:9](-[n:8]2[cH:7][n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:25]([O:26][CH3:27])[cH:24][c:23]32)[s:22]1)=[O:20]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8](-[c:9]3[n:10][c:11](-[c:12]4[cH:13][cH:14][cH:15][cH:16][cH:17]4)[c:18]([C:19](=[O:... | CCOC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1-c1ccccc1 | COc1cc2ncn(-c3nc(-c4ccccc4)c(C(=O)O)s3)c2cc1OC | null | null | C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2csc(-n3cnc4ccccc43)n2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4](:[#16;a:5]):[c:6]:[#7;a:7]>>[#16;a:5]:[c:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1]):[c:6]:[#7;a:7] | 88 | [{"value": 88.0, "product": "COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC=CC=C2)C(=O)O)C=C1OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.4, "product": "COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC=CC=C2)C(=O)O)C=C1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-(5,6-Dimethoxybenzoimidazol-1-yl)-4-phenylthiazole-5-carboxylic acid ethyl ester (180 mg, 0.44 mmol) was suspended in THF (4 ml), NaOH (15%, 1.5 ml) and water (2 ml) and the mixture was stirred at 40-50° C. for 3 hrs. After THF was removed, the residue was extracted with ethyl acetate (2×2 mL). The aqueous was then n... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2[nH]cnc2c1.c1cscn1.c1ccccc1 | Other | C1CCOC1 | null | null | CCOC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1-c1ccccc1>C1CCOC1>COc1cc2ncn(-c3nc(-c4ccccc4)c(C(=O)O)s3)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bb4775cc5c1145c0a1255bd2f894cd37 | CCOC(=O)c1sc(-n2cnc3ccccc32)nc1-c1ccccc1.[NH4+]>>NC(=O)c1sc(-n2cnc3ccccc32)nc1-c1ccccc1 | FC(C(=O)O)(F)F.C(C)OC(=O)C1=C(N=C(S1)N1C=NC2=C1C=CC=C2)C2=CC=CC=C2.[OH-].[NH4+]>>N1(C=NC2=C1C=CC=C2)C=2SC(=C(N2)C2=CC=CC=C2)C(=O)N | CCO[C:2](=[O:3])[c:4]1[s:5][c:6](-[n:7]2[cH:8][n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]23)[n:16][c:17]1-[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1.[NH4+:1]>>[NH2:1][C:2](=[O:3])[c:4]1[s:5][c:6](-[n:7]2[cH:8][n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]23)[n:16][c:17]1-[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1 | CCOC(=O)c1sc(-n2cnc3ccccc32)nc1-c1ccccc1.[NH4+] | NC(=O)c1sc(-n2cnc3ccccc32)nc1-c1ccccc1 | null | null | null | Acylation | OtherReaction | d5b10d4f469e7a196a3b04a6a9e159a7d90514b6df5b50c1197d4b1b774c04e1 | adc0ef6f6c1340dd2dbab737c85bf17fc842769181c5db1a2b4f82b391b28f9f | c1ccc(-c2csc(-n3cnc4ccccc43)n2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#16;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[c:8].[NH4+;D0:9]>>[NH2;D1;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#16;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[c:8] | 13 | [{"value": 13.0, "product": "N1(C=NC2=C1C=CC=C2)C=2SC(=C(N2)C2=CC=CC=C2)C(=O)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Benzoimidazol-1-yl-4-phenyl-thiazole-5-carboxylic acid amide was prepared from 2-Benzoimidazol-1-yl-4-phenyl-thiazole-5-carboxylic acid ethyl ester (75 mg, 0.21 mmol) and ammonium hydroxide as described above in the general amide formation procedure. Preparative HPLC with trifluoroacetic acid, 9.1 mg, 13% yield. MS M... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary amide | null | null | c1cscn1.c1ccc2[nH]cnc2c1.c1ccccc1 | HO- | null | null | null | CCOC(=O)c1sc(-n2cnc3ccccc32)nc1-c1ccccc1.[NH4+]>>NC(=O)c1sc(-n2cnc3ccccc32)nc1-c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f6a29c8c6eea4dfdba4d9337dde91421 | CCOC(=O)c1sc(Cl)nc1-c1ccccc1.Cc1cc2nc[nH]c2cc1C>>Cc1cc2ncn(-c3nc(-c4ccccc4)c(C(=O)O)s3)c2cc1C | CC1=CC2=C(N=CN2)C=C1C.C(C)OC(=O)C1=C(N=C(S1)Cl)C1=CC=CC=C1>>CC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC=CC=C2)C(=O)O)C=C1C | CC[O:20][C:18]([c:17]1[c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[n:9][c:8](Cl)[s:21]1)=[O:19].[CH3:1][c:2]1[cH:3][c:4]2[n:5][cH:6][nH:7][c:22]2[cH:23][c:24]1[CH3:25]>>[CH3:1][c:2]1[cH:3][c:4]2[n:5][cH:6][n:7](-[c:8]3[n:9][c:10](-[c:11]4[cH:12][cH:13][cH:14][cH:15][cH:16]4)[c:17]([C:18](=[O:19])[OH:20])[s:21]3... | CCOC(=O)c1sc(Cl)nc1-c1ccccc1.Cc1cc2nc[nH]c2cc1C | Cc1cc2ncn(-c3nc(-c4ccccc4)c(C(=O)O)s3)c2cc1C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | ec8532a11ed9b83fbbba3bdf52733b203d59017a181516e3b19fc619199ea16f | 73d3046582ebe4ceb7e2b5dab4179dafc796946799b04fa5a989e4e71d346a3b | c1ccc(-c2csc(-n3cnc4ccccc43)n2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[#16;a:5]:[c;H0;D3;+0:6](-Cl):[#7;a:7]:[c:8]:1.[c:9]:[c:10]1:[nH;D2;+0:11]:[c:12]:[#7;a:13]:[c:14]:1:[c:15]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4]1:[#16;a:5]:[c;H0;D3;+0:6](-[n;H0;D3;+0:11]2:[c:12]:[#7;a:13]:[c:14](:[c:15]):[c:10]:2:[c:9]):[#7;a:7]:[c:8]:1 | null | [] | null | null | null | null | 2-(5,6-Dimethylbenzoimidazol-1-yl)-4-phenylthiazole-5-carboxylic acid was prepared in a similar manner as that for Example 1 starting with the reaction of 5,6-dimethylbenzoimidazole and 2-Chloro-4-phenylthiazole-5-carboxylic acid ethyl ester. 1H-NMR(DMSO-D6) 8.82 (s, 1H); 7.98 (s, 1H); 7.82-7.92 (m, 2H); 7.58 (s, 1H); ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester | Carboxylic acid | c1cscn1.c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1.c1cscn1 | c1ccc2[nH]cnc2c1.c1cscn1.c1ccccc1 | HCl | null | null | null | CCOC(=O)c1sc(Cl)nc1-c1ccccc1.Cc1cc2nc[nH]c2cc1C>>Cc1cc2ncn(-c3nc(-c4ccccc4)c(C(=O)O)s3)c2cc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-32c6f14ec2074983be4c1949f91105d3 | CCOC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1-c1ccccc1.N>>COc1cc2ncn(-c3nc(-c4ccccc4)c(C(N)=O)s3)c2cc1OC | C(C)OC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)C2=CC=CC=C2.N>>COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC=CC=C2)C(=O)N)C=C1OC | CCO[C:19]([c:18]1[c:11](-[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[n:10][c:9](-[n:8]2[cH:7][n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:25]([O:26][CH3:27])[cH:24][c:23]32)[s:22]1)=[O:21].[NH3:20]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8](-[c:9]3[n:10][c:11](-[c:12]4[cH:13][cH:14][cH:15][cH:16][cH:17]4)[c:18]([C:19](... | CCOC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1-c1ccccc1.N | COc1cc2ncn(-c3nc(-c4ccccc4)c(C(N)=O)s3)c2cc1OC | null | null | C(C)O | Acylation | OtherReaction | d5b10d4f469e7a196a3b04a6a9e159a7d90514b6df5b50c1197d4b1b774c04e1 | adc0ef6f6c1340dd2dbab737c85bf17fc842769181c5db1a2b4f82b391b28f9f | c1ccc(-c2csc(-n3cnc4ccccc43)n2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#16;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[c:8].[NH3;D0;+0:9]>>[NH2;D1;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#16;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[c:8] | 36 | [{"value": 36.0, "product": "COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC=CC=C2)C(=O)N)C=C1OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-phenyl-thiazole-5-carboxylic acid amide was prepared from 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-phenyl-thiazole-5-carboxylic acid ethyl ester (80 mg, 0.20 mmol) and ammonia in ethanol (29 molar) as described above in the general amide formation procedure. The product was isolated... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary amide | null | null | c1ccc2[nH]cnc2c1.c1cscn1.c1ccccc1 | HO- | C(C)O | null | null | CCOC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1-c1ccccc1.N>C(C)O>COc1cc2ncn(-c3nc(-c4ccccc4)c(C(N)=O)s3)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-613b1935d1d64b12be7ea78814253fd8 | CCOC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1-c1ccccc1.CNC>>COc1cc2ncn(-c3nc(-c4ccccc4)c(C(=O)N(C)C)s3)c2cc1OC | C(C)OC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)C2=CC=CC=C2.CNC>>CN(C(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)C2=CC=CC=C2)C | CCO[C:19]([c:18]1[c:11](-[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[n:10][c:9](-[n:8]2[cH:7][n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:27]([O:28][CH3:29])[cH:26][c:25]32)[s:24]1)=[O:20].[NH:21]([CH3:22])[CH3:23]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8](-[c:9]3[n:10][c:11](-[c:12]4[cH:13][cH:14][cH:15][cH:16][cH:17... | CCOC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1-c1ccccc1.CNC | COc1cc2ncn(-c3nc(-c4ccccc4)c(C(=O)N(C)C)s3)c2cc1OC | null | null | CO | Acylation | Aminolysis of esters | d147787750807073759132276086de98566af6772417f9288b6300bf1de7801c | fa66342dd118fe5531ba6a998ac8fab92d2b0db4fd04688560eec7d04e9be0e4 | c1ccc(-c2csc(-n3cnc4ccccc43)n2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#16;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[c:8].[C;D1;H3:9]-[NH;D2;+0:10]-[C;D1;H3:11]>>[C;D1;H3:9]-[N;H0;D3;+0:10](-[C;D1;H3:11])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#16;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[c:8] | null | [] | null | null | null | null | 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-phenyl-thiazole-5-carboxylic acid dimethylamide was prepared from 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-phenyl-thiazole-5-carboxylic acid ethyl ester (48.8 mg, 0.12 mmol) and dimethyl amine in methanol (2 molar) as described above in the general amide formation procedure. Product... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Tertiary amide | null | null | c1ccc2[nH]cnc2c1.c1cscn1.c1ccccc1 | HO- | CO | null | null | CCOC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1-c1ccccc1.CNC>CO>COc1cc2ncn(-c3nc(-c4ccccc4)c(C(=O)N(C)C)s3)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bab919471b49460297e5e432b8cbb56a | CCN.CCOC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1-c1ccccc1>>CCNC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1-c1ccccc1 | C(C)OC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)C2=CC=CC=C2.C(C)N>>C(C)NC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)C2=CC=CC=C2 | [CH3:1][CH2:2][NH2:3].CCO[C:4](=[O:5])[c:6]1[s:7][c:8](-[n:9]2[cH:10][n:11][c:12]3[cH:13][c:14]([O:15][CH3:16])[c:17]([O:18][CH3:19])[cH:20][c:21]23)[n:22][c:23]1-[c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[c:6]1[s:7][c:8](-[n:9]2[cH:10][n:11][c:12]3[cH:13][c:14]([O:15][CH3:16])[c:17]... | CCN.CCOC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1-c1ccccc1 | CCNC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1-c1ccccc1 | null | null | CO | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | c1ccc(-c2csc(-n3cnc4ccccc43)n2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#16;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[c:8].[C;D1;H3:9]-[C:10]-[NH2;D1;+0:11]>>[C;D1;H3:9]-[C:10]-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#16;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[c:8] | null | [] | null | null | null | null | 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-phenyl-thiazole-5-carboxylic acid ethylamide was prepared from 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-phenyl-thiazole-5-carboxylic acid ethyl ester (30 mg, 0.07 mmol) and ethylamine in methanol (2 molar) as described above in the general amide formation procedure. Product was isol... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1cscn1.c1ccc2[nH]cnc2c1.c1ccccc1 | HO- | CO | null | null | CCN.CCOC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1-c1ccccc1>CO>CCNC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1-c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d612e4db810f4c038452da2bbc6fc150 | CCOC(=O)c1sc(Cl)nc1-c1ccccc1>>O=C(O)c1sc(Cl)nc1-c1ccccc1 | C(C)OC(=O)C1=C(N=C(S1)Cl)C1=CC=CC=C1>>ClC=1SC(=C(N1)C1=CC=CC=C1)C(=O)O | CC[O:3][C:2](=[O:1])[c:4]1[s:5][c:6]([Cl:7])[n:8][c:9]1-[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1>>[O:1]=[C:2]([OH:3])[c:4]1[s:5][c:6]([Cl:7])[n:8][c:9]1-[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1 | CCOC(=O)c1sc(Cl)nc1-c1ccccc1 | O=C(O)c1sc(Cl)nc1-c1ccccc1 | null | null | O1CCCC1.[OH-].[Na+] | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2cscn2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4](:[#16;a:5]):[c:6]:[#7;a:7]>>[#16;a:5]:[c:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1]):[c:6]:[#7;a:7] | 92.6 | [{"value": 35.0, "product": "ClC=1SC(=C(N1)C1=CC=CC=C1)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.6, "product": "ClC=1SC(=C(N1)C1=CC=CC=C1)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A mixture of 2-Chloro-4-phenyl-thiazole-5-carboxylic acid ethyl ester (1 g, 3.74 mmol) in tetrahydrofuran (10 ml) and NaOH (15%, 4.8 ml) was stirred at room temperature for 2 hr. After removal of tetrahydrofuran, the aqueous was neutralized with aqueous hydrochloric acid (3 N) to ˜pH=3. The solid was filtered and washe... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cscn1.c1ccccc1 | Other | O1CCCC1.[OH-].[Na+] | null | 2 | CCOC(=O)c1sc(Cl)nc1-c1ccccc1>O1CCCC1.[OH-].[Na+]>O=C(O)c1sc(Cl)nc1-c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-99f1d4865b4b4902a6aeeb9077daab74 | COc1cc2nc[nH]c2cc1OC.N#Cc1sc(Cl)nc1-c1ccccc1>>COc1cc2ncn(-c3nc(-c4ccccc4)c(C#N)s3)c2cc1OC | COC1=CC2=C(N=CN2)C=C1OC.ClC=1SC(=C(N1)C1=CC=CC=C1)C#N.N1C=NC=2C1=CC=1COCOC1C2>>COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC=CC=C2)C#N)C=C1OC | [CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][nH:8][c:22]2[cH:23][c:24]1[O:25][CH3:26].Cl[c:9]1[n:10][c:11](-[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]([C:19]#[N:20])[s:21]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8](-[c:9]3[n:10][c:11](-[c:12]4[cH:13][cH:14][cH:15][cH:16][cH:17]4)[c:18]([C:19]#[N:20])[s:21]3)... | COc1cc2nc[nH]c2cc1OC.N#Cc1sc(Cl)nc1-c1ccccc1 | COc1cc2ncn(-c3nc(-c4ccccc4)c(C#N)s3)c2cc1OC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | b38f76237cdec2baf41c9411839797fed979828e4dd9354fb2aa8a56efaef6ba | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc(-c2csc(-n3cnc4ccccc43)n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1.[c:6]:[c:7]1:[nH;D2;+0:8]:[c:9]:[#7;a:10]:[c:11]:1:[c:12]>>[c:6]:[c:7]1:[c:11](:[c:12]):[#7;a:10]:[c:9]:[n;H0;D3;+0:8]:1-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1 | 47 | [{"value": 47.0, "product": "COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC=CC=C2)C#N)C=C1OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-phenyl-thiazole-5-carbonitrile (48.8 mg, yield 47%) was prepared from 5,6-dimethoxybenzimidazole (76 mg, 0.43 mmol) and 2-chloro-4-phenyl-thiazole-5-carbonitrile as described in Example 1 (63 mg, 0.28 mmol). MS M/z 363 (M+1)
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2[nH]cnc2c1.c1cscn1 | c1ccc2[nH]cnc2c1.c1cscn1 | c1ccc2[nH]cnc2c1.c1cscn1.c1ccccc1 | HCl | null | null | null | COc1cc2nc[nH]c2cc1OC.N#Cc1sc(Cl)nc1-c1ccccc1>>COc1cc2ncn(-c3nc(-c4ccccc4)c(C#N)s3)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fb6e880335694781a11645def0a210f7 | COc1cc2ncn(-c3nc(-c4ccccc4)c(C#N)s3)c2cc1OC.[N-]=[N+]=[N-]>>COc1cc2ncn(-c3nc(-c4ccccc4)c(-c4nnn[nH]4)s3)c2cc1OC | O.COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC=CC=C2)C#N)C=C1OC.[N-]=[N+]=[N-].[Na+].[Cl-].[NH4+]>>COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC=CC=C2)C2=NN=NN2)C=C1OC | [CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8](-[c:9]3[n:10][c:11](-[c:12]4[cH:13][cH:14][cH:15][cH:16][cH:17]4)[c:18]([C:19]#[N:20])[s:24]3)[c:25]2[cH:26][c:27]1[O:28][CH3:29].[N-:21]=[N+:22]=[N-:23]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8](-[c:9]3[n:10][c:11](-[c:12]4[cH:13][cH:14][cH:15][cH:16][cH:17]4)[c:18]... | COc1cc2ncn(-c3nc(-c4ccccc4)c(C#N)s3)c2cc1OC.[N-]=[N+]=[N-] | COc1cc2ncn(-c3nc(-c4ccccc4)c(-c4nnn[nH]4)s3)c2cc1OC | null | null | CN1C(CCC1)=O | Aromatic Heterocycle Formation | OtherReaction | 237b84aaa459abf427f233dc6a07a1d9de824f980714e458423189bb68f60f12 | d8c808528b7ee68720aaeebd35cb6a2a30e344748d0066102cdae99843b93cf0 | c1ccc(-c2nc(-n3cnc4ccccc43)sc2-c2nnn[nH]2)cc1 | [#7;a:1]:[c:2]:[#7;a:3]-[c:4]1:[#16;a:5]:[c;H0;D3;+0:6](-[C;H0;D2;+0:7]#[N;H0;D1;+0:8]):[c:9](-[c:10]):[#7;a:11]:1.[N-;H0;D1:12]=[N+;H0;D2:13]=[N-;H0;D1:14]>>[#7;a:1]:[c:2]:[#7;a:3]-[c:4]1:[#16;a:5]:[c;H0;D3;+0:6](-[c;H0;D3;+0:7]2:[n;H0;D2;+0:8]:[n;H0;D2;+0:12]:[n;H0;D2;+0:13]:[nH;D2;+0:14]:2):[c:9](-[c:10]):[#7;a:11]:... | 47.3 | [{"value": 47.0, "product": "COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC=CC=C2)C2=NN=NN2)C=C1OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.3, "product": "COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC=CC=C2)C2=NN=NN2)C=C1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | 1 | HOUR | A mixture of 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-phenyl-thiazole-5-carbonitrile (261 mg, 0.72 mmol), sodium azide (220 mg) and ammonium chloride (250 mg) in N-methylpyrrolidone (2.5 ml) was stirred at 110° C. for 1 hr. Water was added and the mixture was extracted with methylene chloride. After removal of solvent, t... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | null | null | c1nnn[nH]1 | c1ccc2[nH]cnc2c1.c1cscn1.c1ccccc1.c1nnn[nH]1 | null | CN1C(CCC1)=O | 110 | 1 | COc1cc2ncn(-c3nc(-c4ccccc4)c(C#N)s3)c2cc1OC.[N-]=[N+]=[N-]>CN1C(CCC1)=O>COc1cc2ncn(-c3nc(-c4ccccc4)c(-c4nnn[nH]4)s3)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ce90a2564f46480babd0cc3e1ace11c7 | CCOC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1-c1ccccc1.NC1CC1>>COc1cc2ncn(-c3nc(-c4ccccc4)c(C(=O)NC4CC4)s3)c2cc1OC | C(C)OC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)C2=CC=CC=C2.C1(CC1)N>>C1(CC1)NC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)C2=CC=CC=C2 | CCO[C:19]([c:18]1[c:11](-[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[n:10][c:9](-[n:8]2[cH:7][n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:28]([O:29][CH3:30])[cH:27][c:26]32)[s:25]1)=[O:20].[NH2:21][CH:22]1[CH2:23][CH2:24]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8](-[c:9]3[n:10][c:11](-[c:12]4[cH:13][cH:14][cH:15][cH:1... | CCOC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1-c1ccccc1.NC1CC1 | COc1cc2ncn(-c3nc(-c4ccccc4)c(C(=O)NC4CC4)s3)c2cc1OC | null | null | CO | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | O=C(NC1CC1)c1sc(-n2cnc3ccccc32)nc1-c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#16;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[c:8].[NH2;D1;+0:9]-[C:10]1-[C:11]-[C:12]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:9]-[C:10]1-[C:11]-[C:12]-1)-[c:3]1:[#16;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[c:8] | null | [] | null | null | null | null | 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-phenyl-thiazole-5-carboxylic acid cyclopropylamide was prepared from 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-phenyl-thiazole-5-carboxylic acid ethyl ester (24 mg, 0.06 mmol) and cyclopropylamine in methanol (4 molar) as described above in the general amide formation procedure. Prod... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccc2[nH]cnc2c1.c1cscn1.c1ccccc1.C1CC1 | HO- | CO | null | null | CCOC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1-c1ccccc1.NC1CC1>CO>COc1cc2ncn(-c3nc(-c4ccccc4)c(C(=O)NC4CC4)s3)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-950ff29ccb2f4da8b36cb7e8427e747f | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.COc1ccc(B(O)O)cc1OC>>COc1ccc(-c2nc(-n3cnc4cc(OC)c(OC)cc43)sc2C(=O)O)cc1OC | COC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)Br.COC=1C=C(C=CC1OC)B(O)O>>COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC(=C(C=C2)OC)OC)C(=O)O)C=C1OC | C[O:27][C:25]([c:24]1[c:7](Br)[n:8][c:9](-[n:10]2[cH:11][n:12][c:13]3[cH:14][c:15]([O:16][CH3:17])[c:18]([O:19][CH3:20])[cH:21][c:22]23)[s:23]1)=[O:26].OB(O)[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:29]([O:30][CH3:31])[cH:28]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][c:9](-[n:10]3[cH:11][n:12][c:13]4[cH:14][c:15... | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.COc1ccc(B(O)O)cc1OC | COc1ccc(-c2nc(-n3cnc4cc(OC)c(OC)cc43)sc2C(=O)O)cc1OC | null | null | null | C-C Coupling | OtherReaction | f263884194c3689072b842d9444db2ca155af322288a9afe28e6da9e83653e3c | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc(-c2csc(-n3cnc4ccccc43)n2)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#16;a:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C.O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[O;D1;H0:7]=[C:6](-[OH;D1;+0:8])-[c:5]1:[#16;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13] | 60 | [{"value": 60.0, "product": "COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC(=C(C=C2)OC)OC)C(=O)O)C=C1OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.8, "product": "COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC(=C(C=C2)OC)OC)C(=O)O)C=C1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a similar manner as described for Example 26, 4-bromo-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid methyl ester (40 mg, 0.1 mmol) and 3,4-dimethoxyphenylboronic acid (27.3 mg, 0.15 mmol) gave 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-(3,4-dimethoxy-phenyl)-thiazole-5-carboxylic acid (26.4 mg, 60%) as... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1cscn1.c1ccccc1 | c1ccccc1.c1cscn1 | c1ccccc1.c1cscn1.c1ccc2[nH]cnc2c1 | HBr.B | null | null | null | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.COc1ccc(B(O)O)cc1OC>>COc1ccc(-c2nc(-n3cnc4cc(OC)c(OC)cc43)sc2C(=O)O)cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a43f73ea71054f398ab5c17438a8a78b | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1ccc(F)c(Cl)c1>>COc1cc2ncn(-c3nc(-c4ccc(F)c(Cl)c4)c(C(=O)O)s3)c2cc1OC | COC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)Br.ClC=1C=C(C=CC1F)B(O)O>>ClC=1C=C(C=CC1F)C=1N=C(SC1C(=O)O)N1C=NC2=C1C=C(C(=C2)OC)OC | C[O:23][C:21]([c:20]1[c:11](Br)[n:10][c:9](-[n:8]2[cH:7][n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:27]([O:28][CH3:29])[cH:26][c:25]32)[s:24]1)=[O:22].OB(O)[c:12]1[cH:13][cH:14][c:15]([F:16])[c:17]([Cl:18])[cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8](-[c:9]3[n:10][c:11](-[c:12]4[cH:13][cH:14][c:15]([F:16])[c:17]... | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1ccc(F)c(Cl)c1 | COc1cc2ncn(-c3nc(-c4ccc(F)c(Cl)c4)c(C(=O)O)s3)c2cc1OC | null | null | null | C-C Coupling | OtherReaction | f263884194c3689072b842d9444db2ca155af322288a9afe28e6da9e83653e3c | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc(-c2csc(-n3cnc4ccccc43)n2)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#16;a:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C.O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[O;D1;H0:7]=[C:6](-[OH;D1;+0:8])-[c:5]1:[#16;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13] | 19 | [{"value": 19.0, "product": "ClC=1C=C(C=CC1F)C=1N=C(SC1C(=O)O)N1C=NC2=C1C=C(C(=C2)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 18.9, "product": "ClC=1C=C(C=CC1F)C=1N=C(SC1C(=O)O)N1C=NC2=C1C=C(C(=C2)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a similar manner as described for Example 26, 4-bromo-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid methyl ester (40 mg, 0.1 mmol) and 3-chloro-4-fluorophenylboronic acid (26.2 mg, 0.15 mmol) gave 4-(3-Chloro-4-fluoro-phenyl)-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid (8.2 mg, ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1cscn1.c1ccccc1 | c1cscn1.c1ccccc1 | c1ccc2[nH]cnc2c1.c1cscn1.c1ccccc1 | HBr.B | null | null | null | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1ccc(F)c(Cl)c1>>COc1cc2ncn(-c3nc(-c4ccc(F)c(Cl)c4)c(C(=O)O)s3)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-879b0c927d714358b78bab6d425e821d | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1cccc(F)c1>>COc1cc2ncn(-c3nc(-c4cccc(F)c4)c(C(=O)O)s3)c2cc1OC | COC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)Br.FC=1C=C(C=CC1)B(O)O>>COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC(=CC=C2)F)C(=O)O)C=C1OC | C[O:22][C:20]([c:19]1[c:11](Br)[n:10][c:9](-[n:8]2[cH:7][n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:26]([O:27][CH3:28])[cH:25][c:24]32)[s:23]1)=[O:21].OB(O)[c:12]1[cH:13][cH:14][cH:15][c:16]([F:17])[cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8](-[c:9]3[n:10][c:11](-[c:12]4[cH:13][cH:14][cH:15][c:16]([F:17])[cH:18]... | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1cccc(F)c1 | COc1cc2ncn(-c3nc(-c4cccc(F)c4)c(C(=O)O)s3)c2cc1OC | null | null | null | C-C Coupling | OtherReaction | f263884194c3689072b842d9444db2ca155af322288a9afe28e6da9e83653e3c | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc(-c2csc(-n3cnc4ccccc43)n2)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#16;a:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C.O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[O;D1;H0:7]=[C:6](-[OH;D1;+0:8])-[c:5]1:[#16;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13] | 20 | [{"value": 20.0, "product": "COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC(=CC=C2)F)C(=O)O)C=C1OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 19.5, "product": "COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC(=CC=C2)F)C(=O)O)C=C1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a similar manner as described for Example 26, 4-bromo-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid methyl ester (40 mg, 0.1 mmol) and 3-fluorophenylboronic acid (21 mg, 0.15 mmol) gave 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-(3-fluoro-phenyl)-thiazole-5-carboxylic acid (7.8 mg, 20%) as a white soli... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1cscn1.c1ccccc1 | c1cscn1.c1ccccc1 | c1ccc2[nH]cnc2c1.c1cscn1.c1ccccc1 | HBr.B | null | null | null | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1cccc(F)c1>>COc1cc2ncn(-c3nc(-c4cccc(F)c4)c(C(=O)O)s3)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0c432ad6e03a4d1ea75e44ac91761844 | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1ccccc1Cl>>COc1cc2ncn(-c3nc(-c4ccccc4Cl)c(C(=O)O)s3)c2cc1OC | COC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)Br.ClC1=C(C=CC=C1)B(O)O>>ClC1=C(C=CC=C1)C=1N=C(SC1C(=O)O)N1C=NC2=C1C=C(C(=C2)OC)OC | C[O:22][C:20]([c:19]1[c:11](Br)[n:10][c:9](-[n:8]2[cH:7][n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:26]([O:27][CH3:28])[cH:25][c:24]32)[s:23]1)=[O:21].OB(O)[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[Cl:18]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8](-[c:9]3[n:10][c:11](-[c:12]4[cH:13][cH:14][cH:15][cH:16][c:17]4[Cl:18])... | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1ccccc1Cl | COc1cc2ncn(-c3nc(-c4ccccc4Cl)c(C(=O)O)s3)c2cc1OC | null | null | null | C-C Coupling | OtherReaction | f263884194c3689072b842d9444db2ca155af322288a9afe28e6da9e83653e3c | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc(-c2csc(-n3cnc4ccccc43)n2)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#16;a:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C.O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12](-[Cl;D1;H0:13]):[c:14]>>[Cl;D1;H0:13]-[c:12](:[c:14]):[c;H0;D3;+0:9](-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#16;a:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8]):[c:10]:[c:11] | 46.2 | [{"value": 46.0, "product": "ClC1=C(C=CC=C1)C=1N=C(SC1C(=O)O)N1C=NC2=C1C=C(C(=C2)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.2, "product": "ClC1=C(C=CC=C1)C=1N=C(SC1C(=O)O)N1C=NC2=C1C=C(C(=C2)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a similar manner as described for Example 26, 4-bromo-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid methyl ester (40 mg, 0.1 mmol) and 2-chlorophenylboronic acid (23.5 mg, 0.15 mmol) gave 4-(2-Chloro-phenyl)-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid (19.2 mg, 46%) as a white s... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1cscn1.c1ccccc1 | c1cscn1.c1ccccc1 | c1ccc2[nH]cnc2c1.c1cscn1.c1ccccc1 | HBr.B | null | null | null | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1ccccc1Cl>>COc1cc2ncn(-c3nc(-c4ccccc4Cl)c(C(=O)O)s3)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1ab497d711da436ea193882c249cc4ab | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1ccc2c(c1)OCO2>>COc1cc2ncn(-c3nc(-c4ccc5c(c4)OCO5)c(C(=O)O)s3)c2cc1OC | COC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)Br.C1OC=2C=C(C=CC2O1)B(O)O>>O1COC2=C1C=CC(=C2)C=2N=C(SC2C(=O)O)N2C=NC1=C2C=C(C(=C1)OC)OC | C[O:24][C:22]([c:21]1[c:11](Br)[n:10][c:9](-[n:8]2[cH:7][n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:28]([O:29][CH3:30])[cH:27][c:26]32)[s:25]1)=[O:23].OB(O)[c:12]1[cH:13][cH:14][c:15]2[c:16]([cH:17]1)[O:18][CH2:19][O:20]2>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8](-[c:9]3[n:10][c:11](-[c:12]4[cH:13][cH:14][c:15]5[c:16]... | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1ccc2c(c1)OCO2 | COc1cc2ncn(-c3nc(-c4ccc5c(c4)OCO5)c(C(=O)O)s3)c2cc1OC | null | null | null | C-C Coupling | OtherReaction | 2be91abefca374375f70d11b43d2684970780fd1d29fcf5da44605ad13137d6c | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc2c(c1)ncn2-c1nc(-c2ccc3c(c2)OCO3)cs1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#16;a:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C.O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]-[#8:14]>>[#8:14]-[c:13]:[c:12]:[c;H0;D3;+0:9](-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#16;a:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8]):[c:10]:[c:11] | 25 | [{"value": 25.0, "product": "O1COC2=C1C=CC(=C2)C=2N=C(SC2C(=O)O)N2C=NC1=C2C=C(C(=C1)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 24.7, "product": "O1COC2=C1C=CC(=C2)C=2N=C(SC2C(=O)O)N2C=NC1=C2C=C(C(=C1)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a similar manner as described for Example 26, 4-bromo-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid methyl ester (40 mg, 0.1 mmol) and 3,4-methylenedioxybenzeneboronic acid (24.9 mg, 0.15 mmol) gave 4-Benzo[1,3]dioxol-5-yl-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid (10.5 mg, 25... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1cscn1.c1ccc2c(c1)OCO2 | c1cscn1.c1ccc2c(c1)OCO2 | c1ccc2[nH]cnc2c1.c1cscn1.c1ccc2c(c1)OCO2 | HBr.B | null | null | null | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1ccc2c(c1)OCO2>>COc1cc2ncn(-c3nc(-c4ccc5c(c4)OCO5)c(C(=O)O)s3)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e714197cb214499fa47edb8ecbbac83d | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1ccc(Cl)c(Cl)c1>>COc1cc2ncn(-c3nc(-c4ccc(Cl)c(Cl)c4)c(C(=O)O)s3)c2cc1OC | COC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)Br.ClC=1C=C(C=CC1Cl)B(O)O>>ClC=1C=C(C=CC1Cl)C=1N=C(SC1C(=O)O)N1C=NC2=C1C=C(C(=C2)OC)OC | C[O:23][C:21]([c:20]1[c:11](Br)[n:10][c:9](-[n:8]2[cH:7][n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:27]([O:28][CH3:29])[cH:26][c:25]32)[s:24]1)=[O:22].OB(O)[c:12]1[cH:13][cH:14][c:15]([Cl:16])[c:17]([Cl:18])[cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8](-[c:9]3[n:10][c:11](-[c:12]4[cH:13][cH:14][c:15]([Cl:16])[c:1... | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1ccc(Cl)c(Cl)c1 | COc1cc2ncn(-c3nc(-c4ccc(Cl)c(Cl)c4)c(C(=O)O)s3)c2cc1OC | null | null | null | C-C Coupling | OtherReaction | f263884194c3689072b842d9444db2ca155af322288a9afe28e6da9e83653e3c | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc(-c2csc(-n3cnc4ccccc43)n2)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#16;a:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C.O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[O;D1;H0:7]=[C:6](-[OH;D1;+0:8])-[c:5]1:[#16;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13] | 35.3 | [{"value": 35.0, "product": "ClC=1C=C(C=CC1Cl)C=1N=C(SC1C(=O)O)N1C=NC2=C1C=C(C(=C2)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 35.3, "product": "ClC=1C=C(C=CC1Cl)C=1N=C(SC1C(=O)O)N1C=NC2=C1C=C(C(=C2)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a similar manner as described for Example 26, 4-bromo-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid methyl ester (40 mg, 0.1 mmol) and 3,4-dichlorophenylboronic acid (28.6 mg, 0.15 mmol) gave 4-(3,4-Dichloro-phenyl)-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid (15.9 mg, 35%) as a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1cscn1.c1ccccc1 | c1cscn1.c1ccccc1 | c1ccc2[nH]cnc2c1.c1cscn1.c1ccccc1 | HBr.B | null | null | null | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1ccc(Cl)c(Cl)c1>>COc1cc2ncn(-c3nc(-c4ccc(Cl)c(Cl)c4)c(C(=O)O)s3)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3a8fbc60df854bfdaf019653858ba679 | CC(C)c1cccc(B(O)O)c1.COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br>>COc1cc2ncn(-c3nc(-c4cccc(C(C)C)c4)c(C(=O)O)s3)c2cc1OC | COC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)Br.C(C)(C)C=1C=C(C=CC1)B(O)O>>COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC(=CC=C2)C(C)C)C(=O)O)C=C1OC | OB(O)[c:12]1[cH:13][cH:14][cH:15][c:16]([CH:17]([CH3:18])[CH3:19])[cH:20]1.C[O:24][C:22]([c:21]1[c:11](Br)[n:10][c:9](-[n:8]2[cH:7][n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:28]([O:29][CH3:30])[cH:27][c:26]32)[s:25]1)=[O:23]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8](-[c:9]3[n:10][c:11](-[c:12]4[cH:13][cH:14][cH:15][c... | CC(C)c1cccc(B(O)O)c1.COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br | COc1cc2ncn(-c3nc(-c4cccc(C(C)C)c4)c(C(=O)O)s3)c2cc1OC | null | null | null | C-C Coupling | OtherReaction | f263884194c3689072b842d9444db2ca155af322288a9afe28e6da9e83653e3c | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc(-c2csc(-n3cnc4ccccc43)n2)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#16;a:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C.O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[O;D1;H0:7]=[C:6](-[OH;D1;+0:8])-[c:5]1:[#16;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13] | 44 | [{"value": 44.0, "product": "COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC(=CC=C2)C(C)C)C(=O)O)C=C1OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.9, "product": "COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC(=CC=C2)C(C)C)C(=O)O)C=C1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a similar manner as described for Example 26, 4-bromo-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid methyl ester (40 mg, 0.1 mmol) and 3-isopropylphenylboronic acid (24.6 mg, 0.15 mmol) gave 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-(3-isopropyl-phenyl)-thiazole-5-carboxylic acid (18.6 mg, 44%) as a w... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1ccccc1.c1cscn1 | c1cscn1.c1ccccc1 | c1ccc2[nH]cnc2c1.c1cscn1.c1ccccc1 | HBr.B | null | null | null | CC(C)c1cccc(B(O)O)c1.COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br>>COc1cc2ncn(-c3nc(-c4cccc(C(C)C)c4)c(C(=O)O)s3)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-202afac41ead4155b0e6e8530a84c2c9 | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1ccsc1>>COc1cc2ncn(-c3nc(-c4ccsc4)c(C(=O)O)s3)c2cc1OC | COC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)Br.S1C=C(C=C1)B(O)O>>COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CSC=C2)C(=O)O)C=C1OC | C[O:20][C:18]([c:17]1[c:11](Br)[n:10][c:9](-[n:8]2[cH:7][n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:24]([O:25][CH3:26])[cH:23][c:22]32)[s:21]1)=[O:19].OB(O)[c:12]1[cH:13][cH:14][s:15][cH:16]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8](-[c:9]3[n:10][c:11](-[c:12]4[cH:13][cH:14][s:15][cH:16]4)[c:17]([C:18](=[O:19])[OH:20... | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1ccsc1 | COc1cc2ncn(-c3nc(-c4ccsc4)c(C(=O)O)s3)c2cc1OC | null | null | null | C-C Coupling | OtherReaction | 0ed2d1457ada7a09f0b8cc1706b21f6fab34ba9c2452322a30b35a2c41d1fe63 | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc2c(c1)ncn2-c1nc(-c2ccsc2)cs1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#16;a:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C.O-B(-O)-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[#16;a:12]:[c:13]:1>>[O;D1;H0:7]=[C:6](-[OH;D1;+0:8])-[c:5]1:[#16;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[#16;a:12]:[c:13]:1 | 78 | [{"value": 78.0, "product": "COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CSC=C2)C(=O)O)C=C1OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.7, "product": "COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CSC=C2)C(=O)O)C=C1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a similar manner as described for Example 26, 4-bromo-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid methyl ester (40 mg, 0.1 mmol) and thiophene-3-boronic acid (19.2 mg, 0.15 mmol) gave 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-thiophen-3-yl-thiazole-5-carboxylic acid (30.1 mg, 78%) as a white solid. ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1cscn1.c1ccsc1 | c1cscn1.c1ccsc1 | c1ccc2[nH]cnc2c1.c1cscn1.c1ccsc1 | HBr.B | null | null | null | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1ccsc1>>COc1cc2ncn(-c3nc(-c4ccsc4)c(C(=O)O)s3)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-97e1be71531e4514a0017251a3ba16db | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.Cc1ccc(B(O)O)cc1>>COc1cc2ncn(-c3nc(-c4ccc(C)cc4)c(C(=O)O)s3)c2cc1OC | COC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)Br.CC1=CC=C(C=C1)B(O)O.C(=O)([O-])[O-].[Na+].[Na+].[OH-].[Na+]>>COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC=C(C=C2)C)C(=O)O)C=C1OC | C[O:22][C:20]([c:19]1[c:11](Br)[n:10][c:9](-[n:8]2[cH:7][n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:26]([O:27][CH3:28])[cH:25][c:24]32)[s:23]1)=[O:21].OB(O)[c:12]1[cH:13][cH:14][c:15]([CH3:16])[cH:17][cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8](-[c:9]3[n:10][c:11](-[c:12]4[cH:13][cH:14][c:15]([CH3:16])[cH:17][cH... | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.Cc1ccc(B(O)O)cc1 | COc1cc2ncn(-c3nc(-c4ccc(C)cc4)c(C(=O)O)s3)c2cc1OC | null | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2] | O.COCCOC.CO.C1CCOC1 | C-C Coupling | OtherReaction | f263884194c3689072b842d9444db2ca155af322288a9afe28e6da9e83653e3c | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc(-c2csc(-n3cnc4ccccc43)n2)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#16;a:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C.O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[O;D1;H0:7]=[C:6](-[OH;D1;+0:8])-[c:5]1:[#16;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13] | 53.4 | [{"value": 53.0, "product": "COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC=C(C=C2)C)C(=O)O)C=C1OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.4, "product": "COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC=C(C=C2)C)C(=O)O)C=C1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | To a solution of 4-bromo-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid methyl ester (40 mg, 0.1 mmol), 4-methylphenylboronic acid (20.4 mg, 0.15 mmol) in ethylene glycol dimethyl ether (1 ml) was added Na2CO3 (2M, 100 μL, 0.2 mmol) and [1,1′-bis(diphenylphosphino)-ferrocene]dichloro palladium(II) (4 m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1cscn1.c1ccccc1 | c1cscn1.c1ccccc1 | c1ccc2[nH]cnc2c1.c1cscn1.c1ccccc1 | HBr.B | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].O.COCCOC.CO.C1CCOC1 | 100 | null | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.Cc1ccc(B(O)O)cc1>C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].O.COCCOC.CO.C1CCOC1>COc1cc2ncn(-c3nc(-c4ccc(C)cc4)c(C(=O)O)s3)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-235ff213f38548958d27e1579ebdf497 | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.Cc1ccccc1B(O)O>>COc1cc2ncn(-c3nc(-c4ccccc4C)c(C(=O)O)s3)c2cc1OC | COC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)Br.CC1=C(C=CC=C1)B(O)O>>COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=C(C=CC=C2)C)C(=O)O)C=C1OC | C[O:22][C:20]([c:19]1[c:11](Br)[n:10][c:9](-[n:8]2[cH:7][n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:26]([O:27][CH3:28])[cH:25][c:24]32)[s:23]1)=[O:21].OB(O)[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[CH3:18]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8](-[c:9]3[n:10][c:11](-[c:12]4[cH:13][cH:14][cH:15][cH:16][c:17]4[CH3:18... | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.Cc1ccccc1B(O)O | COc1cc2ncn(-c3nc(-c4ccccc4C)c(C(=O)O)s3)c2cc1OC | null | null | null | C-C Coupling | OtherReaction | f263884194c3689072b842d9444db2ca155af322288a9afe28e6da9e83653e3c | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc(-c2csc(-n3cnc4ccccc43)n2)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#16;a:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C.O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12](-[C;D1;H3:13]):[c:14]>>[C;D1;H3:13]-[c:12](:[c:14]):[c;H0;D3;+0:9](-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#16;a:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8]):[c:10]:[c:11] | 57 | [{"value": 57.0, "product": "COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=C(C=CC=C2)C)C(=O)O)C=C1OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.9, "product": "COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=C(C=CC=C2)C)C(=O)O)C=C1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a similar manner as described for Example 26, 4-bromo-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid methyl ester (40 mg, 0.1 mmol) and 2-methylphenylboronic acid (20.4 mg, 0.15 mmol) gave 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-o-tolyl-thiazole-5-carboxylic acid (22.5 mg, 57%) as a white solid. 1H N... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1cscn1.c1ccccc1 | c1cscn1.c1ccccc1 | c1ccc2[nH]cnc2c1.c1cscn1.c1ccccc1 | HBr.B | null | null | null | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.Cc1ccccc1B(O)O>>COc1cc2ncn(-c3nc(-c4ccccc4C)c(C(=O)O)s3)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bd991cebe8ea4376aafae9d62ce28f18 | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1cccc(F)c1F>>COc1cc2ncn(-c3nc(-c4cccc(F)c4F)c(C(=O)O)s3)c2cc1OC | COC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)Br.FC1=C(C=CC=C1F)B(O)O>>FC1=C(C=CC=C1F)C=1N=C(SC1C(=O)O)N1C=NC2=C1C=C(C(=C2)OC)OC | C[O:23][C:21]([c:20]1[c:11](Br)[n:10][c:9](-[n:8]2[cH:7][n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:27]([O:28][CH3:29])[cH:26][c:25]32)[s:24]1)=[O:22].OB(O)[c:12]1[cH:13][cH:14][cH:15][c:16]([F:17])[c:18]1[F:19]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8](-[c:9]3[n:10][c:11](-[c:12]4[cH:13][cH:14][cH:15][c:16]([F:17])[c... | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1cccc(F)c1F | COc1cc2ncn(-c3nc(-c4cccc(F)c4F)c(C(=O)O)s3)c2cc1OC | null | null | null | C-C Coupling | OtherReaction | f263884194c3689072b842d9444db2ca155af322288a9afe28e6da9e83653e3c | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc(-c2csc(-n3cnc4ccccc43)n2)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#16;a:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C.O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12](-[F;D1;H0:13]):[c:14]>>[F;D1;H0:13]-[c:12](:[c:14]):[c;H0;D3;+0:9](-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#16;a:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8]):[c:10]:[c:11] | 39 | [{"value": 39.0, "product": "FC1=C(C=CC=C1F)C=1N=C(SC1C(=O)O)N1C=NC2=C1C=C(C(=C2)OC)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In a similar manner as described for Example 26, 4-bromo-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid methyl ester (40 mg, 0.1 mmol) and 2,3-difluorophenylboronic acid (23.7 mg, 0.15 mmol) gave 4-(2,3-Difluoro-phenyl)-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid (16.2 39%) as a whi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1cscn1.c1ccccc1 | c1cscn1.c1ccccc1 | c1ccc2[nH]cnc2c1.c1cscn1.c1ccccc1 | HBr.B | null | null | null | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1cccc(F)c1F>>COc1cc2ncn(-c3nc(-c4cccc(F)c4F)c(C(=O)O)s3)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d9360d4309a44ed58a73f5b3e79e0c3c | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1cccc(Cl)c1>>COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)O)s3)c2cc1OC | COC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)Br.ClC=1C=C(C=CC1)B(O)O>>ClC=1C=C(C=CC1)C=1N=C(SC1C(=O)O)N1C=NC2=C1C=C(C(=C2)OC)OC | C[O:22][C:20]([c:19]1[c:11](Br)[n:10][c:9](-[n:8]2[cH:7][n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:26]([O:27][CH3:28])[cH:25][c:24]32)[s:23]1)=[O:21].OB(O)[c:12]1[cH:13][cH:14][cH:15][c:16]([Cl:17])[cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8](-[c:9]3[n:10][c:11](-[c:12]4[cH:13][cH:14][cH:15][c:16]([Cl:17])[cH:1... | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1cccc(Cl)c1 | COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)O)s3)c2cc1OC | null | null | null | C-C Coupling | OtherReaction | f263884194c3689072b842d9444db2ca155af322288a9afe28e6da9e83653e3c | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc(-c2csc(-n3cnc4ccccc43)n2)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#16;a:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C.O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[O;D1;H0:7]=[C:6](-[OH;D1;+0:8])-[c:5]1:[#16;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13] | 21 | [{"value": 21.0, "product": "ClC=1C=C(C=CC1)C=1N=C(SC1C(=O)O)N1C=NC2=C1C=C(C(=C2)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 20.7, "product": "ClC=1C=C(C=CC1)C=1N=C(SC1C(=O)O)N1C=NC2=C1C=C(C(=C2)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a similar manner as described for Example 26, 4-bromo-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid methyl ester (40 mg, 0.1 mmol) and 3-chlorophenylboronic acid (23.5 mg, 0.15 mmol) gave 4-(3-Chloro-phenyl)-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid (8.6 mg, 21%) as a white so... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1cscn1.c1ccccc1 | c1cscn1.c1ccccc1 | c1ccc2[nH]cnc2c1.c1cscn1.c1ccccc1 | HBr.B | null | null | null | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1cccc(Cl)c1>>COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)O)s3)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3443172873194b13957611ed3d24b997 | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1cccc2ccccc12>>COc1cc2ncn(-c3nc(-c4cccc5ccccc45)c(C(=O)O)s3)c2cc1OC | COC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)Br.C1(=CC=CC2=CC=CC=C12)B(O)O>>COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC=CC3=CC=CC=C23)C(=O)O)C=C1OC | C[O:25][C:23]([c:22]1[c:11](Br)[n:10][c:9](-[n:8]2[cH:7][n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:29]([O:30][CH3:31])[cH:28][c:27]32)[s:26]1)=[O:24].OB(O)[c:12]1[cH:13][cH:14][cH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]12>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8](-[c:9]3[n:10][c:11](-[c:12]4[cH:13][cH:14][cH:15]... | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1cccc2ccccc12 | COc1cc2ncn(-c3nc(-c4cccc5ccccc45)c(C(=O)O)s3)c2cc1OC | null | null | null | C-C Coupling | OtherReaction | c249834ead4e53af5cb050a81f13edb2a5778f7b441ec14f26aa07d5710a04ba | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc2c(-c3csc(-n4cnc5ccccc54)n3)cccc2c1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#16;a:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C.O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12](:[c:13]):[c:14]>>[O;D1;H0:7]=[C:6](-[OH;D1;+0:8])-[c:5]1:[#16;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12](:[c:13]):[c:14] | 37 | [{"value": 37.0, "product": "COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC=CC3=CC=CC=C23)C(=O)O)C=C1OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.9, "product": "COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC=CC3=CC=CC=C23)C(=O)O)C=C1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a similar manner as described for Example 26, 4-bromo-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid methyl ester (40 mg, 0.1 mmol) and 1-naphthaleneboronic acid (25.8 mg, 0.15 mmol) gave 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-naphthalen-1-yl-thiazole-5-carboxylic acid (15.9 mg, 37%) as a white soli... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1cscn1.c1ccc2ccccc2c1 | c1cscn1.c1ccc2ccccc2c1 | c1ccc2[nH]cnc2c1.c1cscn1.c1ccc2ccccc2c1 | HBr.B | null | null | null | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1cccc2ccccc12>>COc1cc2ncn(-c3nc(-c4cccc5ccccc45)c(C(=O)O)s3)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9bbef3dc2cee4b7ea9e5066d534c6f9a | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1cccnc1>>COc1cc2ncn(-c3nc(-c4cccnc4)c(C(=O)O)s3)c2cc1OC | COC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)Br.N1=CC(=CC=C1)B(O)O>>COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C=2C=NC=CC2)C(=O)O)C=C1OC | C[O:21][C:19]([c:18]1[c:11](Br)[n:10][c:9](-[n:8]2[cH:7][n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:25]([O:26][CH3:27])[cH:24][c:23]32)[s:22]1)=[O:20].OB(O)[c:12]1[cH:13][cH:14][cH:15][n:16][cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8](-[c:9]3[n:10][c:11](-[c:12]4[cH:13][cH:14][cH:15][n:16][cH:17]4)[c:18]([C:19](... | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1cccnc1 | COc1cc2ncn(-c3nc(-c4cccnc4)c(C(=O)O)s3)c2cc1OC | null | null | null | C-C Coupling | OtherReaction | 58a128499e1cf40b3d2acb49265b500ef6547a0f5f09ed85c82cab43505a2ce6 | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1cncc(-c2csc(-n3cnc4ccccc43)n2)c1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#16;a:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C.O-B(-O)-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[c:12]:[#7;a:13]:[c:14]:1>>[O;D1;H0:7]=[C:6](-[OH;D1;+0:8])-[c:5]1:[#16;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[c:12]:[#7;a:13]:[c:14]:1 | 7 | [{"value": 7.0, "product": "COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C=2C=NC=CC2)C(=O)O)C=C1OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 6.8, "product": "COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C=2C=NC=CC2)C(=O)O)C=C1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a similar manner as described for Example 26, 4-bromo-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid methyl ester (40 mg, 0.1 mmol) and pyridine-3-boronic acid (18.4 mg, 0.15 mmol) gave 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-pyridin-3-yl-thiazole-5-carboxylic acid (2.6 mg, 7%) as a white solid. 1H N... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1cscn1.c1ccncc1 | c1cscn1.c1ccncc1 | c1ccc2[nH]cnc2c1.c1cscn1.c1ccncc1 | HBr.B | null | null | null | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1cccnc1>>COc1cc2ncn(-c3nc(-c4cccnc4)c(C(=O)O)s3)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5e3294a138ba401099617042607b4b46 | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1cccc(O)c1>>COc1cc2ncn(-c3nc(-c4cccc(O)c4)c(C(=O)O)s3)c2cc1OC | COC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)Br.OC=1C=C(C=CC1)B(O)O>>COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC(=CC=C2)O)C(=O)O)C=C1OC | C[O:22][C:20]([c:19]1[c:11](Br)[n:10][c:9](-[n:8]2[cH:7][n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:26]([O:27][CH3:28])[cH:25][c:24]32)[s:23]1)=[O:21].OB(O)[c:12]1[cH:13][cH:14][cH:15][c:16]([OH:17])[cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8](-[c:9]3[n:10][c:11](-[c:12]4[cH:13][cH:14][cH:15][c:16]([OH:17])[cH:1... | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1cccc(O)c1 | COc1cc2ncn(-c3nc(-c4cccc(O)c4)c(C(=O)O)s3)c2cc1OC | null | null | null | C-C Coupling | OtherReaction | f263884194c3689072b842d9444db2ca155af322288a9afe28e6da9e83653e3c | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc(-c2csc(-n3cnc4ccccc43)n2)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#16;a:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C.O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[O;D1;H0:7]=[C:6](-[OH;D1;+0:8])-[c:5]1:[#16;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13] | 6 | [{"value": 6.0, "product": "COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC(=CC=C2)O)C(=O)O)C=C1OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 6.0, "product": "COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC(=CC=C2)O)C(=O)O)C=C1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a similar manner as described for Example 26, 4-bromo-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid methyl ester (40 mg, 0.1 mmol) and 3-hydroxyphenylboronic acid (20.7 mg, 0.15 mmol) gave 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-(3-hydroxy-phenyl)-thiazole-5-carboxylic acid (2.4 mg, 6%) as a white s... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1cscn1.c1ccccc1 | c1cscn1.c1ccccc1 | c1ccc2[nH]cnc2c1.c1cscn1.c1ccccc1 | HBr.B | null | null | null | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1cccc(O)c1>>COc1cc2ncn(-c3nc(-c4cccc(O)c4)c(C(=O)O)s3)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d3a109297a274f87aaf18a2099d36500 | COc1cc2ncn(-c3nc(-c4ccccc4)c(C(=O)O)s3)c2cc1OC.Nc1ccccc1>>COc1cc2ncn(-c3nc(-c4ccccc4)c(C(=O)Nc4ccccc4)s3)c2cc1OC | NC1=CC=CC=C1.COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC=CC=C2)C(=O)O)C=C1OC.C(C)N(C(C)C)CC.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F>>C1(=CC=CC=C1)NC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)C2=CC=CC=C2 | O[C:19]([c:18]1[c:11](-[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[n:10][c:9](-[n:8]2[cH:7][n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:31]([O:32][CH3:33])[cH:30][c:29]32)[s:28]1)=[O:20].[NH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8](-[c:9]3[n:10][c:11](-[c:12]4[cH:13][cH... | COc1cc2ncn(-c3nc(-c4ccccc4)c(C(=O)O)s3)c2cc1OC.Nc1ccccc1 | COc1cc2ncn(-c3nc(-c4ccccc4)c(C(=O)Nc4ccccc4)s3)c2cc1OC | null | null | CN(C=O)C.C(C)(=O)OCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1sc(-n2cnc3ccccc32)nc1-c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#16;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12])-[c:3]1:[#16;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[c:8] | 87.6 | [{"value": 86.4, "product": "C1(=CC=CC=C1)NC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.6, "product": "C1(=CC=CC=C1)NC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To a solution of 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-phenyl-thiazole-5-carboxylic acid (30 mg, 0.075 mmol) in dimethylformamide (1 ml) was added diethylisopropylamine (15.6 μL, 0.09 mmol) and HATU (28.5 mg, 0.075 mmol). The mixture was stirred under ambient temperature for 5 min. Aniline (6.8 μL, 0.075 mmol) was add... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2[nH]cnc2c1.c1cscn1.c1ccccc1.c1ccccc1 | HO- | CN(C=O)C.C(C)(=O)OCC | null | 0.083333 | COc1cc2ncn(-c3nc(-c4ccccc4)c(C(=O)O)s3)c2cc1OC.Nc1ccccc1>CN(C=O)C.C(C)(=O)OCC>COc1cc2ncn(-c3nc(-c4ccccc4)c(C(=O)Nc4ccccc4)s3)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ccc8952ed6af4a2db53bf5335c8373ae | CCOC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1-c1ccccc1>>CCOC(=O)c1sc(-n2cnc3cc(O)c(O)cc32)nc1-c1ccccc1 | CSC.B(F)(F)F.C(C)OC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)C2=CC=CC=C2>>C(C)OC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)O)O)C2=CC=CC=C2 | C[O:15][c:14]1[cH:13][c:12]2[n:11][cH:10][n:9](-[c:8]3[s:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:21](-[c:22]4[cH:23][cH:24][cH:25][cH:26][cH:27]4)[n:20]3)[c:19]2[cH:18][c:16]1[O:17]C>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[s:7][c:8](-[n:9]2[cH:10][n:11][c:12]3[cH:13][c:14]([OH:15])[c:16]([OH:17])[cH:18][c:19]23)[n:... | CCOC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1-c1ccccc1 | CCOC(=O)c1sc(-n2cnc3cc(O)c(O)cc32)nc1-c1ccccc1 | null | null | C(Cl)Cl | Deprotection | OtherReaction | a0f05885bbc65ae2846cad0ac34029941211b2ef3a426958b0c8aa83bb16fe86 | 9df751cd682ad9d54ed75d7313aaead6a019c5d37ede15c4672866d319b900ff | c1ccc(-c2csc(-n3cnc4ccccc43)n2)cc1 | C-[O;H0;D2;+0:1]-[c:2]1:[c:3]:[c:4](:[#7;a:5]):[c:6](:[#7;a:7]):[c:8]:[c:9]:1-[O;H0;D2;+0:10]-C>>[#7;a:5]:[c:4]1:[c:3]:[c:2](-[OH;D1;+0:1]):[c:9](-[OH;D1;+0:10]):[c:8]:[c:6]:1:[#7;a:7] | 90.4 | [{"value": 90.0, "product": "C(C)OC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)O)O)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.4, "product": "C(C)OC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)O)O)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 40 | MINUTE | Boron trifluoride dimethylsulfide (4.1 ml, 39 mmol) was added in multiportions over 5 hrs. to a suspension of 2-(5,6-Dimethoxybenzoimidazol-1-yl)-4-phenylthiazole-5-carboxylic acid ethyl ester (2.04 g, 4.99 mmol) in methylene chloride at RT. The mixture was stirred for an additional 40 mins. Ice water was added. Methyl... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1cscn1.c1ccc2[nH]cnc2c1.c1ccccc1 | Other | C(Cl)Cl | null | 0.666667 | CCOC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1-c1ccccc1>C(Cl)Cl>CCOC(=O)c1sc(-n2cnc3cc(O)c(O)cc32)nc1-c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c131f239de98446eb4a934f1e3e146c9 | C=Cc1cccc(B(O)O)c1.COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br>>C=Cc1cccc(-c2nc(-n3cnc4cc(OC)c(OC)cc43)sc2C(=O)O)c1 | COC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)Br.C(=C)C=1C=C(C=CC1)B(O)O>>COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC(=CC=C2)C=C)C(=O)O)C=C1OC | OB(O)[c:7]1[cH:6][cH:5][cH:4][c:3]([CH:2]=[CH2:1])[cH:29]1.C[O:28][C:26]([c:25]1[c:8](Br)[n:9][c:10](-[n:11]2[cH:12][n:13][c:14]3[cH:15][c:16]([O:17][CH3:18])[c:19]([O:20][CH3:21])[cH:22][c:23]23)[s:24]1)=[O:27]>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[n:9][c:10](-[n:11]3[cH:12][n:13][c:14]4[cH:15][c:16]([O... | C=Cc1cccc(B(O)O)c1.COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br | C=Cc1cccc(-c2nc(-n3cnc4cc(OC)c(OC)cc43)sc2C(=O)O)c1 | null | null | null | C-C Coupling | OtherReaction | f263884194c3689072b842d9444db2ca155af322288a9afe28e6da9e83653e3c | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc(-c2csc(-n3cnc4ccccc43)n2)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#16;a:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C.O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]-[C:12]=[C;D1;H2:13]):[c:14]:[c:15]>>[C;D1;H2:13]=[C:12]-[c:11]:[c:10]:[c;H0;D3;+0:9](-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#16;a:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8]):[c:14]:[c:15] | 64 | [{"value": 64.0, "product": "COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC(=CC=C2)C=C)C(=O)O)C=C1OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.8, "product": "COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC(=CC=C2)C=C)C(=O)O)C=C1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a similar manner as described for Example 26, 4-bromo-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid methyl ester (40 mg, 0.1 mmol) and 3-vinylphenylboronic acid (22 mg, 0.15 mmol) gave 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-(3-vinyl-phenyl)-thiazole-5-carboxylic acid (26 mg, 64%) as a white solid. ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1ccccc1.c1cscn1 | c1ccccc1.c1cscn1 | c1ccccc1.c1cscn1.c1ccc2[nH]cnc2c1 | HBr.B | null | null | null | C=Cc1cccc(B(O)O)c1.COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br>>C=Cc1cccc(-c2nc(-n3cnc4cc(OC)c(OC)cc43)sc2C(=O)O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e933b33566be4a8490467ce7b6bfd579 | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1cc(Cl)cc(Cl)c1>>COc1cc2ncn(-c3nc(-c4cc(Cl)cc(Cl)c4)c(C(=O)O)s3)c2cc1OC | COC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)Br.ClC=1C=C(C=C(C1)Cl)B(O)O>>ClC=1C=C(C=C(C1)Cl)C=1N=C(SC1C(=O)O)N1C=NC2=C1C=C(C(=C2)OC)OC | C[O:23][C:21]([c:20]1[c:11](Br)[n:10][c:9](-[n:8]2[cH:7][n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:27]([O:28][CH3:29])[cH:26][c:25]32)[s:24]1)=[O:22].OB(O)[c:12]1[cH:13][c:14]([Cl:15])[cH:16][c:17]([Cl:18])[cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8](-[c:9]3[n:10][c:11](-[c:12]4[cH:13][c:14]([Cl:15])[cH:16][c:1... | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1cc(Cl)cc(Cl)c1 | COc1cc2ncn(-c3nc(-c4cc(Cl)cc(Cl)c4)c(C(=O)O)s3)c2cc1OC | null | null | null | C-C Coupling | OtherReaction | f263884194c3689072b842d9444db2ca155af322288a9afe28e6da9e83653e3c | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc(-c2csc(-n3cnc4ccccc43)n2)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#16;a:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C.O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[O;D1;H0:7]=[C:6](-[OH;D1;+0:8])-[c:5]1:[#16;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13] | 51.1 | [{"value": 51.0, "product": "ClC=1C=C(C=C(C1)Cl)C=1N=C(SC1C(=O)O)N1C=NC2=C1C=C(C(=C2)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.1, "product": "ClC=1C=C(C=C(C1)Cl)C=1N=C(SC1C(=O)O)N1C=NC2=C1C=C(C(=C2)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a similar manner as described for Example 26, 4-bromo-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid methyl ester (40 mg, 0.1 mmol) and 3,5-dichlorophenylboronic acid (27 mg, 0.15 mmol) gave 4-(3,5-Dichloro-phenyl)-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid (23 mg, 51%) as a whi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1cscn1.c1ccccc1 | c1cscn1.c1ccccc1 | c1ccc2[nH]cnc2c1.c1cscn1.c1ccccc1 | HBr.B | null | null | null | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1cc(Cl)cc(Cl)c1>>COc1cc2ncn(-c3nc(-c4cc(Cl)cc(Cl)c4)c(C(=O)O)s3)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c124c4e5794b44b4af072d5cc6728dfd | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1cccc(Br)c1>>COc1cc2ncn(-c3nc(-c4cccc(Br)c4)c(C(=O)O)s3)c2cc1OC | COC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)Br.BrC=1C=C(C=CC1)B(O)O>>BrC=1C=C(C=CC1)C=1N=C(SC1C(=O)O)N1C=NC2=C1C=C(C(=C2)OC)OC | C[O:22][C:20]([c:19]1[c:11](Br)[n:10][c:9](-[n:8]2[cH:7][n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:26]([O:27][CH3:28])[cH:25][c:24]32)[s:23]1)=[O:21].OB(O)[c:12]1[cH:13][cH:14][cH:15][c:16]([Br:17])[cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8](-[c:9]3[n:10][c:11](-[c:12]4[cH:13][cH:14][cH:15][c:16]([Br:17])[cH:1... | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1cccc(Br)c1 | COc1cc2ncn(-c3nc(-c4cccc(Br)c4)c(C(=O)O)s3)c2cc1OC | null | null | null | C-C Coupling | OtherReaction | f263884194c3689072b842d9444db2ca155af322288a9afe28e6da9e83653e3c | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc(-c2csc(-n3cnc4ccccc43)n2)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#16;a:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C.O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[O;D1;H0:7]=[C:6](-[OH;D1;+0:8])-[c:5]1:[#16;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13] | 9 | [{"value": 9.0, "product": "BrC=1C=C(C=CC1)C=1N=C(SC1C(=O)O)N1C=NC2=C1C=C(C(=C2)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 8.7, "product": "BrC=1C=C(C=CC1)C=1N=C(SC1C(=O)O)N1C=NC2=C1C=C(C(=C2)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a similar manner as described for Example 26, 4-bromo-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid methyl ester (40 mg, 0.1 mmol) and 3-bromophenylboronic acid (30 mg, 0.15 mmol) gave 4-(3-Bromo-phenyl)-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid (4.0 mg, 9%) as a white solid. ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1cscn1.c1ccccc1 | c1cscn1.c1ccccc1 | c1ccc2[nH]cnc2c1.c1cscn1.c1ccccc1 | HBr.B | null | null | null | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1cccc(Br)c1>>COc1cc2ncn(-c3nc(-c4cccc(Br)c4)c(C(=O)O)s3)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d6bdc22d77c04d9da84b1af804deef63 | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1cccc(C(F)(F)F)c1>>COc1cc2ncn(-c3nc(-c4cccc(C(F)(F)F)c4)c(C(=O)O)s3)c2cc1OC | COC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)Br.FC(C=1C=C(C=CC1)B(O)O)(F)F>>COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC(=CC=C2)C(F)(F)F)C(=O)O)C=C1OC | C[O:25][C:23]([c:22]1[c:11](Br)[n:10][c:9](-[n:8]2[cH:7][n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:29]([O:30][CH3:31])[cH:28][c:27]32)[s:26]1)=[O:24].OB(O)[c:12]1[cH:13][cH:14][cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8](-[c:9]3[n:10][c:11](-[c:12]4[cH:13][cH:14][cH:15... | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1cccc(C(F)(F)F)c1 | COc1cc2ncn(-c3nc(-c4cccc(C(F)(F)F)c4)c(C(=O)O)s3)c2cc1OC | null | null | null | C-C Coupling | OtherReaction | f263884194c3689072b842d9444db2ca155af322288a9afe28e6da9e83653e3c | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc(-c2csc(-n3cnc4ccccc43)n2)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#16;a:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C.O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[O;D1;H0:7]=[C:6](-[OH;D1;+0:8])-[c:5]1:[#16;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13] | 58.1 | [{"value": 58.0, "product": "COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC(=CC=C2)C(F)(F)F)C(=O)O)C=C1OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.1, "product": "COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC(=CC=C2)C(F)(F)F)C(=O)O)C=C1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a similar manner as described for Example 26, 4-bromo-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid methyl ester (40 mg, 0.1 mmol) and 3-trifluoromethylphenylboronic acid (28.5 mg, 0.15 mmol) gave 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-(3-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid (26.1 mg,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1cscn1.c1ccccc1 | c1cscn1.c1ccccc1 | c1ccc2[nH]cnc2c1.c1cscn1.c1ccccc1 | HBr.B | null | null | null | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1cccc(C(F)(F)F)c1>>COc1cc2ncn(-c3nc(-c4cccc(C(F)(F)F)c4)c(C(=O)O)s3)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-740ec3c68917421da89ffd6a67458490 | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1ccc(C(F)(F)F)c(Cl)c1>>COc1cc2ncn(-c3nc(-c4ccc(C(F)(F)F)c(Cl)c4)c(C(=O)O)s3)c2cc1OC | COC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)Br.ClC=1C=C(C=CC1C(F)(F)F)B(O)O>>ClC=1C=C(C=CC1C(F)(F)F)C=1N=C(SC1C(=O)O)N1C=NC2=C1C=C(C(=C2)OC)OC | C[O:26][C:24]([c:23]1[c:11](Br)[n:10][c:9](-[n:8]2[cH:7][n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:30]([O:31][CH3:32])[cH:29][c:28]32)[s:27]1)=[O:25].OB(O)[c:12]1[cH:13][cH:14][c:15]([C:16]([F:17])([F:18])[F:19])[c:20]([Cl:21])[cH:22]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8](-[c:9]3[n:10][c:11](-[c:12]4[cH:13][cH:1... | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1ccc(C(F)(F)F)c(Cl)c1 | COc1cc2ncn(-c3nc(-c4ccc(C(F)(F)F)c(Cl)c4)c(C(=O)O)s3)c2cc1OC | null | null | null | C-C Coupling | OtherReaction | f263884194c3689072b842d9444db2ca155af322288a9afe28e6da9e83653e3c | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc(-c2csc(-n3cnc4ccccc43)n2)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#16;a:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C.O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[O;D1;H0:7]=[C:6](-[OH;D1;+0:8])-[c:5]1:[#16;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13] | 16 | [{"value": 16.0, "product": "ClC=1C=C(C=CC1C(F)(F)F)C=1N=C(SC1C(=O)O)N1C=NC2=C1C=C(C(=C2)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 15.9, "product": "ClC=1C=C(C=CC1C(F)(F)F)C=1N=C(SC1C(=O)O)N1C=NC2=C1C=C(C(=C2)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a similar manner as described for Example 26, 4-bromo-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid methyl ester (40 mg, 0.1 mmol) and 3-chloro-4-trifluoromethylphenylboronic acid (33.7 mg, 0.15 mmol) gave 4-(3-Chloro-4-trifluoromethyl-phenyl)-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxy... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1cscn1.c1ccccc1 | c1cscn1.c1ccccc1 | c1ccc2[nH]cnc2c1.c1cscn1.c1ccccc1 | HBr.B | null | null | null | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1ccc(C(F)(F)F)c(Cl)c1>>COc1cc2ncn(-c3nc(-c4ccc(C(F)(F)F)c(Cl)c4)c(C(=O)O)s3)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ce2172ac60ee41dc908fb5a9b301b45b | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.Cn1ccc2cc(B(O)O)ccc21>>COc1cc2ncn(-c3nc(-c4ccc5c(ccn5C)c4)c(C(=O)O)s3)c2cc1OC | COC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)Br.CN1C=CC2=CC(=CC=C12)B(O)O>>COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C=2C=C3C=CN(C3=CC2)C)C(=O)O)C=C1OC | C[O:25][C:23]([c:22]1[c:11](Br)[n:10][c:9](-[n:8]2[cH:7][n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:29]([O:30][CH3:31])[cH:28][c:27]32)[s:26]1)=[O:24].OB(O)[c:12]1[cH:13][cH:14][c:15]2[c:16]([cH:17][cH:18][n:19]2[CH3:20])[cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8](-[c:9]3[n:10][c:11](-[c:12]4[cH:13][cH:14][c:15... | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.Cn1ccc2cc(B(O)O)ccc21 | COc1cc2ncn(-c3nc(-c4ccc5c(ccn5C)c4)c(C(=O)O)s3)c2cc1OC | null | null | null | C-C Coupling | OtherReaction | ceebcf352d77229d3b9c14eff09e7aac88aca94d5d4385b9ea0d401292d74f92 | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc2c(c1)ncn2-c1nc(-c2ccc3[nH]ccc3c2)cs1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#16;a:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C.O-B(-O)-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[c:12](:[#7;a:13]):[c:14]:[c:15]:1>>[#7;a:13]:[c:12]1:[c:11]:[c:10]:[c;H0;D3;+0:9](-[c;H0;D3;+0:1]2:[#7;a:2]:[c:3]:[#16;a:4]:[c:5]:2-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8]):[c:15]:[c:14]:1 | 12 | [{"value": 12.0, "product": "COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C=2C=C3C=CN(C3=CC2)C)C(=O)O)C=C1OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 11.7, "product": "COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C=2C=C3C=CN(C3=CC2)C)C(=O)O)C=C1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a similar manner as described for Example 26, 4-bromo-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid methyl ester (40 mg, 0.1 mmol) and N-methylindole-5-boronic acid (26.2 mg, 0.15 mmol) gave 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-(1-methyl-1H-indol-5-yl)-thiazole-5-carboxylic acid (5.1 mg, 12%) as ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1cscn1.c1ccc2[nH]ccc2c1 | c1cscn1.c1ccc2[nH]ccc2c1 | c1ccc2[nH]cnc2c1.c1cscn1.c1ccc2[nH]ccc2c1 | HBr.B | null | null | null | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.Cn1ccc2cc(B(O)O)ccc21>>COc1cc2ncn(-c3nc(-c4ccc5c(ccn5C)c4)c(C(=O)O)s3)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-38f139cc1fb6484eb8bbcda09d1148c6 | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1ccc(F)c(F)c1>>COc1cc2ncn(-c3nc(-c4ccc(F)c(F)c4)c(C(=O)O)s3)c2cc1OC | COC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)Br.FC=1C=C(C=CC1F)B(O)O>>FC=1C=C(C=CC1F)C=1N=C(SC1C(=O)O)N1C=NC2=C1C=C(C(=C2)OC)OC | C[O:23][C:21]([c:20]1[c:11](Br)[n:10][c:9](-[n:8]2[cH:7][n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:27]([O:28][CH3:29])[cH:26][c:25]32)[s:24]1)=[O:22].OB(O)[c:12]1[cH:13][cH:14][c:15]([F:16])[c:17]([F:18])[cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8](-[c:9]3[n:10][c:11](-[c:12]4[cH:13][cH:14][c:15]([F:16])[c:17](... | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1ccc(F)c(F)c1 | COc1cc2ncn(-c3nc(-c4ccc(F)c(F)c4)c(C(=O)O)s3)c2cc1OC | null | null | null | C-C Coupling | OtherReaction | f263884194c3689072b842d9444db2ca155af322288a9afe28e6da9e83653e3c | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc(-c2csc(-n3cnc4ccccc43)n2)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#16;a:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C.O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[O;D1;H0:7]=[C:6](-[OH;D1;+0:8])-[c:5]1:[#16;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13] | 21 | [{"value": 21.0, "product": "FC=1C=C(C=CC1F)C=1N=C(SC1C(=O)O)N1C=NC2=C1C=C(C(=C2)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 20.8, "product": "FC=1C=C(C=CC1F)C=1N=C(SC1C(=O)O)N1C=NC2=C1C=C(C(=C2)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a similar manner as described for Example 26, 4-bromo-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid methyl ester (40 mg, 0.1 mmol) and 3,4-difluorophenylboronic acid (23.7 mg, 0.15 mmol) gave 4-(3,4-Difluoro-phenyl)-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid (8.7 mg, 21%) as a ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1cscn1.c1ccccc1 | c1cscn1.c1ccccc1 | c1ccc2[nH]cnc2c1.c1cscn1.c1ccccc1 | HBr.B | null | null | null | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1ccc(F)c(F)c1>>COc1cc2ncn(-c3nc(-c4ccc(F)c(F)c4)c(C(=O)O)s3)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e85216952b934b1c8df0c3f4ada64753 | CCOC(=O)c1sc(-n2cnc3cc(O)c(O)cc32)nc1-c1ccccc1.CN1CCCC1=O.COCCBr>>COCCOc1cc2ncn(-c3nc(-c4ccccc4)c(C(=O)O)s3)c2cc1OCCOC | O.C(C)OC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)O)O)C2=CC=CC=C2.COCCBr.C([O-])([O-])=O.[K+].[K+].CN1C(CCC1)=O>>COCCOC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC=CC=C2)C(=O)O)C=C1OCCOC | [CH3:3][CH2:4][O:24][C:22]([c:21]1[c:14](-[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[n:13][c:12](-[n:11]2[cH:10][n:9][c:8]3[cH:7][c:6]([OH:5])[c:28]([OH:29])[cH:27][c:26]32)[s:25]1)=[O:23].O=C1CCCN1[CH3:1].Br[CH2:30][CH2:31][O:32][CH3:33]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]2[n:9][cH:10][n:11](-[c:12]3[n... | CCOC(=O)c1sc(-n2cnc3cc(O)c(O)cc32)nc1-c1ccccc1.CN1CCCC1=O.COCCBr | COCCOc1cc2ncn(-c3nc(-c4ccccc4)c(C(=O)O)s3)c2cc1OCCOC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1f9d7dda6aa554619ebd2cce26e6d436fea7d5187b4ebc73c49c366581561a06 | 31b20b6e5ca29276309667336e59ba1c90635c7dc1b4092b9a2f6410a6a41368 | c1ccc(-c2csc(-n3cnc4ccccc43)n2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].O=C1-C-C-C-N-1-[CH3;D1;+0:4].[#16;a:5]:[c:6](-[C:7](=[O;D1;H0:8])-[O;H0;D2;+0:9]-[CH2;D2;+0:10]-[CH3;D1;+0:11]):[c:12]:[#7;a:13].[#7;a:14]:[c:15]1:[c:16]:[c:17](-[OH;D1;+0:18]):[c:19](-[OH;D1;+0:20]):[c:21]:[c:22]:1:[#7;a:23]>>[#16;a:5]:[c:6](-[C:7](=[O;D1;H0:8])-[OH;D1;+0:9]):[c:12]:[#7;a... | 17 | [{"value": 17.0, "product": "COCCOC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC=CC=C2)C(=O)O)C=C1OCCOC", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 4 | HOUR | A mixture of 2-(5,6-dihydroxy-benzoimidazol-1-yl)-4-phenyl-thiazole-5-carboxylic acid ethyl ester (118.8 mg, 0.31 mmol, intermediate for Example 39), bromoethyl methyl ether (0.1 ml) and potassium carbonate (200 mg) in N-methylpyrrolidone (2 ml) was stirred at RT overnight and 80° C. for 4 hr. Water was added, and the ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Tertiary amide.Aromatic alcohol.Aromatic alcohol | Carboxylic acid.Ether.Ether.Ether | C1CCNC1 | null | c1ccc2[nH]cnc2c1.c1cscn1.c1ccccc1 | HBr | null | 80 | 4 | CCOC(=O)c1sc(-n2cnc3cc(O)c(O)cc32)nc1-c1ccccc1.CN1CCCC1=O.COCCBr>>COCCOc1cc2ncn(-c3nc(-c4ccccc4)c(C(=O)O)s3)c2cc1OCCOC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1f7f72c44f7944dca4c7b3ae939ee678 | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OCc1cccc(B(O)O)c1>>COc1cc2ncn(-c3nc(-c4cccc(CO)c4)c(C(=O)O)s3)c2cc1OC | COC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)Br.OCC=1C=C(C=CC1)B(O)O>>COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC(=CC=C2)CO)C(=O)O)C=C1OC | C[O:23][C:21]([c:20]1[c:11](Br)[n:10][c:9](-[n:8]2[cH:7][n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:27]([O:28][CH3:29])[cH:26][c:25]32)[s:24]1)=[O:22].OB(O)[c:12]1[cH:13][cH:14][cH:15][c:16]([CH2:17][OH:18])[cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8](-[c:9]3[n:10][c:11](-[c:12]4[cH:13][cH:14][cH:15][c:16]([CH2:... | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OCc1cccc(B(O)O)c1 | COc1cc2ncn(-c3nc(-c4cccc(CO)c4)c(C(=O)O)s3)c2cc1OC | null | null | null | C-C Coupling | OtherReaction | f263884194c3689072b842d9444db2ca155af322288a9afe28e6da9e83653e3c | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc(-c2csc(-n3cnc4ccccc43)n2)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#16;a:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C.O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[O;D1;H0:7]=[C:6](-[OH;D1;+0:8])-[c:5]1:[#16;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13] | 2 | [{"value": 2.0, "product": "COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC(=CC=C2)CO)C(=O)O)C=C1OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 1.9, "product": "COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC(=CC=C2)CO)C(=O)O)C=C1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a similar manner as described for Example 26, 4-bromo-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid methyl ester (40 mg, 0.1 mmol) and 3-hydroxymethylphenylboronic acid (22.9 mg, 0.15 mmol) gave 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-(3-hydroxymethyl-phenyl)-thiazole-5-carboxylic acid (0.8 mg, 2.0%... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1cscn1.c1ccccc1 | c1cscn1.c1ccccc1 | c1ccc2[nH]cnc2c1.c1cscn1.c1ccccc1 | HBr.B | null | null | null | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OCc1cccc(B(O)O)c1>>COc1cc2ncn(-c3nc(-c4cccc(CO)c4)c(C(=O)O)s3)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b5b66d178564491d9f7645ea0d9be57e | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1ccc2c(c1)OCCO2>>COc1cc2ncn(-c3nc(-c4ccc5c(c4)OCCO5)c(C(=O)O)s3)c2cc1OC | COC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)Br.O1CCOC2=C1C=CC(=C2)B(O)O>>O1CCOC2=C1C=CC(=C2)C=2N=C(SC2C(=O)O)N2C=NC1=C2C=C(C(=C1)OC)OC | C[O:25][C:23]([c:22]1[c:11](Br)[n:10][c:9](-[n:8]2[cH:7][n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:29]([O:30][CH3:31])[cH:28][c:27]32)[s:26]1)=[O:24].OB(O)[c:12]1[cH:13][cH:14][c:15]2[c:16]([cH:17]1)[O:18][CH2:19][CH2:20][O:21]2>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8](-[c:9]3[n:10][c:11](-[c:12]4[cH:13][cH:14][c:15... | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1ccc2c(c1)OCCO2 | COc1cc2ncn(-c3nc(-c4ccc5c(c4)OCCO5)c(C(=O)O)s3)c2cc1OC | null | null | null | C-C Coupling | OtherReaction | f589e70e63409b9e35e63fa7758e87bfecd59dc704f8541cd1578b3741023d3c | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc2c(c1)ncn2-c1nc(-c2ccc3c(c2)OCCO3)cs1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#16;a:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C.O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]-[#8:14]>>[#8:14]-[c:13]:[c:12]:[c;H0;D3;+0:9](-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#16;a:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8]):[c:10]:[c:11] | 22 | [{"value": 22.0, "product": "O1CCOC2=C1C=CC(=C2)C=2N=C(SC2C(=O)O)N2C=NC1=C2C=C(C(=C1)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 21.6, "product": "O1CCOC2=C1C=CC(=C2)C=2N=C(SC2C(=O)O)N2C=NC1=C2C=C(C(=C1)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a similar manner as described for Example 26, 4-bromo-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid methyl ester (40 mg, 0.1 mmol) and 1,4-benzodioxane-6-boronic acid (27 mg, 0.15 mmol) gave 4-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid (9.5 m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1cscn1.c1ccc2c(c1)OCCO2 | c1cscn1.c1ccc2c(c1)OCCO2 | c1ccc2[nH]cnc2c1.c1cscn1.c1ccc2c(c1)OCCO2 | HBr.B | null | null | null | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)c1ccc2c(c1)OCCO2>>COc1cc2ncn(-c3nc(-c4ccc5c(c4)OCCO5)c(C(=O)O)s3)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2601f61c18774ab7a121314b7e5cdd18 | C=Cc1ccc(B(O)O)cc1.COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br>>C=Cc1ccc(-c2nc(-n3cnc4cc(OC)c(OC)cc43)sc2C(=O)O)cc1 | COC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)Br.B(C1=CC=C(C=C1)C=C)(O)O>>COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC=C(C=C2)C=C)C(=O)O)C=C1OC | OB(O)[c:6]1[cH:5][cH:4][c:3]([CH:2]=[CH2:1])[cH:29][cH:28]1.C[O:27][C:25]([c:24]1[c:7](Br)[n:8][c:9](-[n:10]2[cH:11][n:12][c:13]3[cH:14][c:15]([O:16][CH3:17])[c:18]([O:19][CH3:20])[cH:21][c:22]23)[s:23]1)=[O:26]>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][c:9](-[n:10]3[cH:11][n:12][c:13]4[cH:14][c:15]([O:16][CH... | C=Cc1ccc(B(O)O)cc1.COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br | C=Cc1ccc(-c2nc(-n3cnc4cc(OC)c(OC)cc43)sc2C(=O)O)cc1 | null | null | null | C-C Coupling | OtherReaction | f263884194c3689072b842d9444db2ca155af322288a9afe28e6da9e83653e3c | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc(-c2csc(-n3cnc4ccccc43)n2)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#16;a:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C.O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[O;D1;H0:7]=[C:6](-[OH;D1;+0:8])-[c:5]1:[#16;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13] | 37.3 | [{"value": 37.0, "product": "COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC=C(C=C2)C=C)C(=O)O)C=C1OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 37.3, "product": "COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC=C(C=C2)C=C)C(=O)O)C=C1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a similar manner as described for Example 26, 4-bromo-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid methyl ester (40 mg, 0.1 mmol) and 4-vinylboronic acid (22.2 mg, 0.15 mmol) gave 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-(4-vinyl-phenyl)-thiazole-5-carboxylic acid (15.2 mg, 37%) as a white solid. 1H... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1ccccc1.c1cscn1 | c1ccccc1.c1cscn1 | c1ccccc1.c1cscn1.c1ccc2[nH]cnc2c1 | HBr.B | null | null | null | C=Cc1ccc(B(O)O)cc1.COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br>>C=Cc1ccc(-c2nc(-n3cnc4cc(OC)c(OC)cc43)sc2C(=O)O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-84897f4b243f4ede9a0f4e007c56cd65 | CN(C)C(=O)c1cccc(B(O)O)c1.COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br>>COc1cc2ncn(-c3nc(-c4cccc(C(=O)N(C)C)c4)c(C(=O)O)s3)c2cc1OC | COC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)Br.CN(C(=O)C=1C=C(C=CC1)B(O)O)C>>COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC(=CC=C2)C(N(C)C)=O)C(=O)O)C=C1OC | OB(O)[c:12]1[cH:13][cH:14][cH:15][c:16]([C:17](=[O:18])[N:19]([CH3:20])[CH3:21])[cH:22]1.C[O:26][C:24]([c:23]1[c:11](Br)[n:10][c:9](-[n:8]2[cH:7][n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:30]([O:31][CH3:32])[cH:29][c:28]32)[s:27]1)=[O:25]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8](-[c:9]3[n:10][c:11](-[c:12]4[cH:13][c... | CN(C)C(=O)c1cccc(B(O)O)c1.COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br | COc1cc2ncn(-c3nc(-c4cccc(C(=O)N(C)C)c4)c(C(=O)O)s3)c2cc1OC | null | null | null | C-C Coupling | OtherReaction | f263884194c3689072b842d9444db2ca155af322288a9afe28e6da9e83653e3c | 5af41468c321f267448297a8abdded64f3cc5543e523be88c60c8574c327b358 | c1ccc(-c2csc(-n3cnc4ccccc43)n2)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#16;a:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C.O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]-[C:14](-[#7:15])=[O;D1;H0:16]>>[#7:15]-[C:14](=[O;D1;H0:16])-[c:13]:[c:12]:[c;H0;D3;+0:9](-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#16;a:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8]):[c:1... | 4 | [{"value": 4.0, "product": "COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC(=CC=C2)C(N(C)C)=O)C(=O)O)C=C1OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 4.0, "product": "COC1=CC2=C(N(C=N2)C=2SC(=C(N2)C2=CC(=CC=C2)C(N(C)C)=O)C(=O)O)C=C1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a similar manner as described for Example 26, 4-bromo-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid methyl ester (40 mg, 0.1 mmol) and 3-dimethylcarbamoylphenylboronic acid (29 mg, 0.15 mmol) gave 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-(3-dimethylcarbamoyl-phenyl)-thiazole-5-carboxylic acid (1.8 mg... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Boronic acid | Carboxylic acid | c1ccccc1.c1cscn1 | c1cscn1.c1ccccc1 | c1ccc2[nH]cnc2c1.c1cscn1.c1ccccc1 | HBr.B | null | null | null | CN(C)C(=O)c1cccc(B(O)O)c1.COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br>>COc1cc2ncn(-c3nc(-c4cccc(C(=O)N(C)C)c4)c(C(=O)O)s3)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-79c97d7eb5cf42ed9c08b38a0ff2f9fc | COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)O)s3)c2cc1OC.NNC(=O)c1cccs1>>COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)NNC(=O)c4cccs4)s3)c2cc1OC | ClC=1C=C(C=CC1)C=1N=C(SC1C(=O)O)N1C=NC2=C1C=C(C(=C2)OC)OC.S1C(=CC=C1)C(=O)NN.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F.C(C)(C)N(CC)C(C)C>>ClC=1C=C(C=CC1)C=1N=C(SC1C(=O)NNC(=O)C=1SC=CC1)N1C=NC2=C1C=C(C(=C2)OC)OC | O[C:20]([c:19]1[c:11](-[c:12]2[cH:13][cH:14][cH:15][c:16]([Cl:17])[cH:18]2)[n:10][c:9](-[n:8]2[cH:7][n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:34]([O:35][CH3:36])[cH:33][c:32]32)[s:31]1)=[O:21].[NH2:22][NH:23][C:24](=[O:25])[c:26]1[cH:27][cH:28][cH:29][s:30]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8](-[c:9]3[n:10][c:... | COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)O)s3)c2cc1OC.NNC(=O)c1cccs1 | COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)NNC(=O)c4cccs4)s3)c2cc1OC | null | null | O.CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 1bfc5046b360bb38c235d234cdd252f03d34a0792ef57a2cdb032482310d9689 | 1f93e2b4a6ed796a4645f0486672499ca332a9bc5c180e504c9a46d8eb8d844d | O=C(NNC(=O)c1sc(-n2cnc3ccccc32)nc1-c1ccccc1)c1cccs1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#16;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[c:8].[#16;a:9]:[c:10]-[C:11](=[O;D1;H0:12])-[#7:13]-[NH2;D1;+0:14]>>[#16;a:9]:[c:10]-[C:11](=[O;D1;H0:12])-[#7:13]-[NH;D2;+0:14]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#16;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[c:8] | 70.2 | [{"value": 70.2, "product": "ClC=1C=C(C=CC1)C=1N=C(SC1C(=O)NNC(=O)C=1SC=CC1)N1C=NC2=C1C=C(C(=C2)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.2, "product": "ClC=1C=C(C=CC1)C=1N=C(SC1C(=O)NNC(=O)C=1SC=CC1)N1C=NC2=C1C=C(C(=C2)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 4-(3-Chloro-phenyl)-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid (41 mg, 0.1 mmol) and thiophene-2-carboxylic acid hydrazide (14.2 mg, 0.1 mmol, Aldrich) in N,N-dimethylformamide (1 ml) was added HATU (38 mg, 0.1 mmol) and diisopropylethylamine (26 μl, 0.15 mmol). The mixture was sti... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Carboxylic acid | Acylhydrazine.Acylhydrazine | null | null | c1ccc2[nH]cnc2c1.c1cscn1.c1ccccc1.c1ccsc1 | HO- | O.CN(C=O)C | null | 8 | COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)O)s3)c2cc1OC.NNC(=O)c1cccs1>O.CN(C=O)C>COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)NNC(=O)c4cccs4)s3)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fb4584ffdf00451db8c31b4290fac671 | COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)O)s3)c2cc1OC.Nc1ccncn1>>COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)Nc4ccncn4)s3)c2cc1OC | ClC=1C=C(C=CC1)C=1N=C(SC1C(=O)O)N1C=NC2=C1C=C(C(=C2)OC)OC.NC1=NC=NC=C1>>N1=CN=C(C=C1)NC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)C2=CC(=CC=C2)Cl | O[C:20]([c:19]1[c:11](-[c:12]2[cH:13][cH:14][cH:15][c:16]([Cl:17])[cH:18]2)[n:10][c:9](-[n:8]2[cH:7][n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:32]([O:33][CH3:34])[cH:31][c:30]32)[s:29]1)=[O:21].[NH2:22][c:23]1[cH:24][cH:25][n:26][cH:27][n:28]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8](-[c:9]3[n:10][c:11](-[c:12]4[cH:... | COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)O)s3)c2cc1OC.Nc1ccncn1 | COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)Nc4ccncn4)s3)c2cc1OC | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccncn1)c1sc(-n2cnc3ccccc32)nc1-c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#16;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[c:8].[NH2;D1;+0:9]-[c:10]1:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]:[c:15]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10]1:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]:[c:15]:1)-[c:3]1:[#16;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[c:8] | 69.7 | [{"value": 69.7, "product": "N1=CN=C(C=C1)NC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)C2=CC(=CC=C2)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.6, "product": "N1=CN=C(C=C1)NC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)C2=CC(=CC=C2)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a similar manner as described for Example 53, 4-(3-Chloro-phenyl)-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid (41 mg, 0.1 mmol) and 4-aminopyrimidine (9.5 mg, 0.1 mmol, Aldrich) gave 4-(3-Chloro-phenyl)-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid pyrimidin-4-ylamide (34.3 mg, ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2[nH]cnc2c1.c1cscn1.c1ccccc1.c1cncnc1 | HO- | null | null | null | COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)O)s3)c2cc1OC.Nc1ccncn1>>COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)Nc4ccncn4)s3)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e6b268bfd146479a94fd857e3d4e9c59 | COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)O)s3)c2cc1OC.COc1cccc(N)c1>>COc1cccc(NC(=O)c2sc(-n3cnc4cc(OC)c(OC)cc43)nc2-c2cccc(Cl)c2)c1 | ClC=1C=C(C=CC1)C=1N=C(SC1C(=O)O)N1C=NC2=C1C=C(C(=C2)OC)OC.COC1=CC(=CC=C1)N>>COC=1C=C(C=CC1)NC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)C2=CC(=CC=C2)Cl | O[C:9](=[O:10])[c:11]1[s:12][c:13](-[n:14]2[cH:15][n:16][c:17]3[cH:18][c:19]([O:20][CH3:21])[c:22]([O:23][CH3:24])[cH:25][c:26]23)[n:27][c:28]1-[c:29]1[cH:30][cH:31][cH:32][c:33]([Cl:34])[cH:35]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH2:8])[cH:36]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH:8][C:9](=[O:10])[c... | COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)O)s3)c2cc1OC.COc1cccc(N)c1 | COc1cccc(NC(=O)c2sc(-n3cnc4cc(OC)c(OC)cc43)nc2-c2cccc(Cl)c2)c1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1)c1sc(-n2cnc3ccccc32)nc1-c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#16;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12])-[c:3]1:[#16;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[c:8] | 86.6 | [{"value": 86.6, "product": "COC=1C=C(C=CC1)NC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)C2=CC(=CC=C2)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.6, "product": "COC=1C=C(C=CC1)NC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)C2=CC(=CC=C2)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a similar manner as described for Example 53, 4-(3-Chloro-phenyl)-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid (41 mg, 0.1 mmol) and 3-anisidine (12.3 mg, 0.1 mmol, Aldrich) gave 4-(3-Chloro-phenyl)-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid (3-methoxy-phenyl)-amide (45.1 mg, ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1cscn1.c1ccc2[nH]cnc2c1.c1ccccc1 | HO- | null | null | null | COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)O)s3)c2cc1OC.COc1cccc(N)c1>>COc1cccc(NC(=O)c2sc(-n3cnc4cc(OC)c(OC)cc43)nc2-c2cccc(Cl)c2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dcf8546ca9be4051a5b5f5b06fbb71f0 | COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)O)s3)c2cc1OC.Nc1nccs1>>COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)Nc4nccs4)s3)c2cc1OC | ClC=1C=C(C=CC1)C=1N=C(SC1C(=O)O)N1C=NC2=C1C=C(C(=C2)OC)OC.NC=1SC=CN1>>S1C(=NC=C1)NC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)C2=CC(=CC=C2)Cl | O[C:20]([c:19]1[c:11](-[c:12]2[cH:13][cH:14][cH:15][c:16]([Cl:17])[cH:18]2)[n:10][c:9](-[n:8]2[cH:7][n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:31]([O:32][CH3:33])[cH:30][c:29]32)[s:28]1)=[O:21].[NH2:22][c:23]1[n:24][cH:25][cH:26][s:27]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8](-[c:9]3[n:10][c:11](-[c:12]4[cH:13][cH:... | COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)O)s3)c2cc1OC.Nc1nccs1 | COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)Nc4nccs4)s3)c2cc1OC | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1nccs1)c1sc(-n2cnc3ccccc32)nc1-c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#16;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[c:8].[NH2;D1;+0:9]-[c:10]1:[#16;a:11]:[c:12]:[c:13]:[#7;a:14]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10]1:[#16;a:11]:[c:12]:[c:13]:[#7;a:14]:1)-[c:3]1:[#16;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[c:8] | 79.5 | [{"value": 79.5, "product": "S1C(=NC=C1)NC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)C2=CC(=CC=C2)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.5, "product": "S1C(=NC=C1)NC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)C2=CC(=CC=C2)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a similar manner as described for Example 53, 4-(3-Chloro-phenyl)-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid (41 mg, 0.1 mmol) and 2-aminothiazole (10.0 mg, 0.1 mmol, Aldrich) gave 4-(3-Chloro-phenyl)-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid thiazol-2-ylamide (39.6 mg, 79.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2[nH]cnc2c1.c1cscn1.c1ccccc1.c1cscn1 | HO- | null | null | null | COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)O)s3)c2cc1OC.Nc1nccs1>>COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)Nc4nccs4)s3)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bfc0ee7048484136b0ef09ad3b98be1b | COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)O)s3)c2cc1OC.Nn1cnnc1>>COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)Nn4cnnc4)s3)c2cc1OC | ClC=1C=C(C=CC1)C=1N=C(SC1C(=O)O)N1C=NC2=C1C=C(C(=C2)OC)OC.NN1C=NN=C1>>N=1N=CN(C1)NC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)C2=CC(=CC=C2)Cl | O[C:20]([c:19]1[c:11](-[c:12]2[cH:13][cH:14][cH:15][c:16]([Cl:17])[cH:18]2)[n:10][c:9](-[n:8]2[cH:7][n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:31]([O:32][CH3:33])[cH:30][c:29]32)[s:28]1)=[O:21].[NH2:22][n:23]1[cH:24][n:25][n:26][cH:27]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8](-[c:9]3[n:10][c:11](-[c:12]4[cH:13][cH:... | COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)O)s3)c2cc1OC.Nn1cnnc1 | COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)Nn4cnnc4)s3)c2cc1OC | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nn1cnnc1)c1sc(-n2cnc3ccccc32)nc1-c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#16;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[c:8].[NH2;D1;+0:9]-[#7;a:10]1:[c:11]:[#7;a:12]:[#7;a:13]:[c:14]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:9]-[#7;a:10]1:[c:11]:[#7;a:12]:[#7;a:13]:[c:14]:1)-[c:3]1:[#16;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[c:8] | 5 | [{"value": 5.0, "product": "N=1N=CN(C1)NC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)C2=CC(=CC=C2)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 5.0, "product": "N=1N=CN(C1)NC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)C2=CC(=CC=C2)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a similar manner as described for Example 53, 4-(3-Chloro-phenyl)-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid (41 mg, 0.1 mmol) and 4-amino-1,2,4-triazole (8.4 mg, 0.1 mmol, Aldrich) gave 4-(3-Chloro-phenyl)-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid [1,2,4]triazol-4-ylamide ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2[nH]cnc2c1.c1cscn1.c1ccccc1.c1nnc[nH]1 | HO- | null | null | null | COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)O)s3)c2cc1OC.Nn1cnnc1>>COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)Nn4cnnc4)s3)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a9b9f7be58f945379c7e2def803e8dae | COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)O)s3)c2cc1OC.Cc1cccc(C(=O)NN)c1>>COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)NNC(=O)c4cccc(C)c4)s3)c2cc1OC | ClC=1C=C(C=CC1)C=1N=C(SC1C(=O)O)N1C=NC2=C1C=C(C(=C2)OC)OC.C1(=CC(=CC=C1)C(=O)NN)C>>ClC=1C=C(C=CC1)C=1N=C(SC1C(=O)NNC(C1=CC(=CC=C1)C)=O)N1C=NC2=C1C=C(C(=C2)OC)OC | O[C:20]([c:19]1[c:11](-[c:12]2[cH:13][cH:14][cH:15][c:16]([Cl:17])[cH:18]2)[n:10][c:9](-[n:8]2[cH:7][n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:36]([O:37][CH3:38])[cH:35][c:34]32)[s:33]1)=[O:21].[NH2:22][NH:23][C:24](=[O:25])[c:26]1[cH:27][cH:28][cH:29][c:30]([CH3:31])[cH:32]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8]... | COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)O)s3)c2cc1OC.Cc1cccc(C(=O)NN)c1 | COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)NNC(=O)c4cccc(C)c4)s3)c2cc1OC | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 1bfc5046b360bb38c235d234cdd252f03d34a0792ef57a2cdb032482310d9689 | 1f93e2b4a6ed796a4645f0486672499ca332a9bc5c180e504c9a46d8eb8d844d | O=C(NNC(=O)c1sc(-n2cnc3ccccc32)nc1-c1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#16;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[c:8].[NH2;D1;+0:9]-[#7:10]-[C:11](=[O;D1;H0:12])-[c:13]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:9]-[#7:10]-[C:11](=[O;D1;H0:12])-[c:13])-[c:3]1:[#16;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[c:8] | 3.8 | [{"value": 3.8, "product": "ClC=1C=C(C=CC1)C=1N=C(SC1C(=O)NNC(C1=CC(=CC=C1)C)=O)N1C=NC2=C1C=C(C(=C2)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 3.8, "product": "ClC=1C=C(C=CC1)C=1N=C(SC1C(=O)NNC(C1=CC(=CC=C1)C)=O)N1C=NC2=C1C=C(C(=C2)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | null | null | null | null | In a similar manner as described for Example 53, 4-(3-Chloro-phenyl)-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid (41 mg, 0.1 mmol) and m-toluic acid hydrazide (15.0 mg, 0.1 mmol, Lancaster) gave 3-Methyl-benzoic acid N′-[4-(3-chloro-phenyl)-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carbonyl]-h... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Carboxylic acid | Acylhydrazine.Acylhydrazine | null | null | c1ccc2[nH]cnc2c1.c1cscn1.c1ccccc1.c1ccccc1 | HO- | null | null | null | COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)O)s3)c2cc1OC.Cc1cccc(C(=O)NN)c1>>COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)NNC(=O)c4cccc(C)c4)s3)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cdfd204a5bc24d5ca42307623e861556 | COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)O)s3)c2cc1OC.Nc1cc[nH]c(=O)n1>>COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)Nc4cc[nH]c(=O)n4)s3)c2cc1OC | ClC=1C=C(C=CC1)C=1N=C(SC1C(=O)O)N1C=NC2=C1C=C(C(=C2)OC)OC.N1C(=O)N=C(N)C=C1>>O=C1NC=CC(=N1)NC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)C2=CC(=CC=C2)Cl | O[C:20]([c:19]1[c:11](-[c:12]2[cH:13][cH:14][cH:15][c:16]([Cl:17])[cH:18]2)[n:10][c:9](-[n:8]2[cH:7][n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:33]([O:34][CH3:35])[cH:32][c:31]32)[s:30]1)=[O:21].[NH2:22][c:23]1[cH:24][cH:25][nH:26][c:27](=[O:28])[n:29]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8](-[c:9]3[n:10][c:11](-[c... | COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)O)s3)c2cc1OC.Nc1cc[nH]c(=O)n1 | COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)Nc4cc[nH]c(=O)n4)s3)c2cc1OC | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1cc[nH]c(=O)n1)c1sc(-n2cnc3ccccc32)nc1-c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#16;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[c:8].[NH2;D1;+0:9]-[c:10]1:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]:[c:15]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10]1:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]:[c:15]:1)-[c:3]1:[#16;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[c:8] | 11 | [{"value": 11.0, "product": "O=C1NC=CC(=N1)NC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)C2=CC(=CC=C2)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 11.0, "product": "O=C1NC=CC(=N1)NC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)C2=CC(=CC=C2)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a similar manner as described for Example 53, 4-(3-Chloro-phenyl)-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid (41 mg, 0.1 mmol) and cytosine (11.1 mg, 0.1 mmol, Aldrich) gave 4-(3-Chloro-phenyl)-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid (2-oxo-1,2-dihydro-pyrimidin-4-yl)-ami... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2[nH]cnc2c1.c1cscn1.c1ccccc1.c1ccncn1 | HO- | null | null | null | COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)O)s3)c2cc1OC.Nc1cc[nH]c(=O)n1>>COc1cc2ncn(-c3nc(-c4cccc(Cl)c4)c(C(=O)Nc4cc[nH]c(=O)n4)s3)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-99e207888bd243beabf304f07f498f58 | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)C1(Cl)C=CC=CN1>>COc1cc2ncn(-c3nc(-c4ccnc(Cl)c4)c(C(=O)O)s3)c2cc1OC | COC(=O)C1=C(N=C(S1)N1C=NC2=C1C=C(C(=C2)OC)OC)Br.ClC1(NC=CC=C1)B(O)O>>ClC1=NC=CC(=C1)C=1N=C(SC1C(=O)O)N1C=NC2=C1C=C(C(=C2)OC)OC | C[O:22][C:20]([c:19]1[c:11](Br)[n:10][c:9](-[n:8]2[cH:7][n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:26]([O:27][CH3:28])[cH:25][c:24]32)[s:23]1)=[O:21].OB(O)[C:16]1([Cl:17])[NH:15][CH:14]=[CH:13][CH:12]=[CH:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8](-[c:9]3[n:10][c:11](-[c:12]4[cH:13][cH:14][n:15][c:16]([Cl:17])[cH... | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)C1(Cl)C=CC=CN1 | COc1cc2ncn(-c3nc(-c4ccnc(Cl)c4)c(C(=O)O)s3)c2cc1OC | null | null | null | C-C Coupling | OtherReaction | 48bc47ed9a4b0545686f380853b2598405ea077723a76e78c487ad11a319ba9c | 05e3eb4ca364d4dd5d7d9c0848a2b8e41d59224ac4a93bb541e406c3ea7919ef | c1ccc2c(c1)ncn2-c1nc(-c2ccncc2)cs1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#16;a:4]:[c:5]:1-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C.O-B(-O)-[C;H0;D4;+0:9]1(-[Cl;D1;H0:10])-[CH;D2;+0:11]=[CH;D2;+0:12]-[CH;D2;+0:13]=[CH;D2;+0:14]-[NH;D2;+0:15]-1>>[Cl;D1;H0:10]-[c;H0;D3;+0:9]1:[cH;D2;+0:11]:[c;H0;D3;+0:12](-[c;H0;D3;+0:1]2:[#7;a:2]:[c:3]:[#16;a:4]:[c:5]:2-[C:6](=[... | 46.4 | [{"value": 46.4, "product": "ClC1=NC=CC(=C1)C=1N=C(SC1C(=O)O)N1C=NC2=C1C=C(C(=C2)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.4, "product": "ClC1=NC=CC(=C1)C=1N=C(SC1C(=O)O)N1C=NC2=C1C=C(C(=C2)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In a similar manner as described for Example 26, 4-bromo-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid methyl ester (120 mg, 0.3 mmol) and 2-chloropyridine-2-boronic acid (71 mg, 0.45 mmol) gave 4-(2-Chloro-pyridin-4-yl)-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid (58 mg, 46.4%) as... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aromatic halide.Tertiary halide.Ester.Boronic acid.Conjugated diene | Aromatic halide.Carboxylic acid | c1cscn1.C1=CCNC=C1 | c1cscn1.c1ccncc1 | c1ccc2[nH]cnc2c1.c1cscn1.c1ccncc1 | HBr.B | null | null | null | COC(=O)c1sc(-n2cnc3cc(OC)c(OC)cc32)nc1Br.OB(O)C1(Cl)C=CC=CN1>>COc1cc2ncn(-c3nc(-c4ccnc(Cl)c4)c(C(=O)O)s3)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8c87d20b662440d4a55bb0bd3cc07d10 | O=C(OO)c1cccc(Cl)c1>>CC1(C)OC(=O)COC1=O | ClC1=CC(=CC=C1)C(=O)OO>>CC1(OC(COC1=O)=O)C | Cl[c:5]1[cH:3][c:2]([C:9]([O:8][OH:4])=[O:10])[cH:1]c[cH:7]1>>[CH3:1][C:2]1([CH3:3])[O:4][C:5](=[O:6])[CH2:7][O:8][C:9]1=[O:10] | O=C(OO)c1cccc(Cl)c1 | CC1(C)OC(=O)COC1=O | null | null | ClCCl | Miscellaneous | OtherReaction | 4400727cd1198764fe8b1969daa817e812a15f25c8b234ac111afebd28f75e4d | 08ae86020599855ef67800c69886dbf7915f83dafbd43cf0edc5db86fcf85ed8 | O=C1COC(=O)CO1 | Cl-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[c;H0;D3;+0:3](-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-[OH;D1;+0:7]):[cH;D2;+0:8]:c:[cH;D2;+0:9]:1>>[CH3;D1;+0:8]-[C;H0;D4;+0:3]1(-[CH3;D1;+0:2])-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:10])-[CH2;D2;+0:9]-[O;H0;D2;+0:6]-[C:4]-1=[O;D1;H0:5] | null | [] | -18 | CELSIUS | null | null | A solution of 5 g of cyclic keto-ester (39 mmol) and 8.1 g of metachloroperbenzoic acid (1.2 eq.) in 40 ml of dichloromethane is heated under reflux for 24 hours. The complete conversion of the ring with 5 members is monitored by NMR 1H on a sample. The reaction medium is then cooled down to −18° C. overnight then filt... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide | Ester.Ester | c1ccccc1 | C1COCCO1 | C1COCCO1 | Other | ClCCl | -18 | null | O=C(OO)c1cccc(Cl)c1>ClCCl>CC1(C)OC(=O)COC1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-888d8d47fb5c4f5f9649e35e4e8651bf | O=C(OO)c1cccc(Cl)c1.O=S(=O)(O)C(F)(F)F>>CC1(C)OC(=O)COC1=O | ClC1=CC(=CC=C1)C(=O)OO.FC(S(=O)(=O)O)(F)F>>CC1(OC(COC1=O)=O)C | Clc1[cH:3][c:2]([C:9]([O:8][OH:4])=[O:10])[cH:1]c[cH:7]1.O=S(O)([C:5](F)(F)F)=[O:6]>>[CH3:1][C:2]1([CH3:3])[O:4][C:5](=[O:6])[CH2:7][O:8][C:9]1=[O:10] | O=C(OO)c1cccc(Cl)c1.O=S(=O)(O)C(F)(F)F | CC1(C)OC(=O)COC1=O | null | null | ClCCl | Heteroatom Alkylation and Arylation | OtherReaction | 03f692efa2fbafa3dc3b5ecb485e08b376972c9c82d2ceb92cfd883696edd565 | 311d7bfa1bd9b6b7c60384461a4bc313a1f774cce7ab37764991ad07ffb60024 | O=C1COC(=O)CO1 | Cl-c1:[cH;D2;+0:1]:[c;H0;D3;+0:2](-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[OH;D1;+0:6]):[cH;D2;+0:7]:c:[cH;D2;+0:8]:1.F-[C;H0;D4;+0:9](-F)(-F)-S(-O)(=O)=[O;H0;D1;+0:10]>>[CH3;D1;+0:7]-[C;H0;D4;+0:2]1(-[CH3;D1;+0:1])-[O;H0;D2;+0:6]-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-[CH2;D2;+0:8]-[O;H0;D2;+0:5]-[C:3]-1=[O;D1;H0:4] | 60 | [{"value": 60.0, "product": "CC1(OC(COC1=O)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A solution of 1 g of cyclic keto-ester (7.8 mmol), 2.7 g of metachloroperbenzoic acid (2 eq.) and 70 μl of trifluoromethanesulphonic acid (0.1 eq.) in 20 ml of dichloromethane is left under stirring at ambient temperature for 3 hours. The solvent is eliminated under vacuum, then the medium is analyzed. NMR 1H reveals t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary halide.Tertiary halide.Tertiary halide.Peroxide.Sulfonic acid | Ester.Ester | c1ccccc1 | C1COCCO1 | C1COCCO1 | Other | ClCCl | null | 3 | O=C(OO)c1cccc(Cl)c1.O=S(=O)(O)C(F)(F)F>ClCCl>CC1(C)OC(=O)COC1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-19d94f0f1bb1409e909c25ac1d6bf545 | O=C(OO)c1cccc(Cl)c1>>CCC1(C)OC(=O)COC1=O | ClC1=CC(=CC=C1)C(=O)OO>>C(C)C1(OC(COC1=O)=O)C | Cl[c:3]1[cH:4][c:8]([C:6]([O:5][OH:7])=[O:11])[cH:2][cH:1][cH:10]1>>[CH3:1][CH2:2][C:3]1([CH3:4])[O:5][C:6](=[O:7])[CH2:8][O:9][C:10]1=[O:11] | O=C(OO)c1cccc(Cl)c1 | CCC1(C)OC(=O)COC1=O | null | null | ClCCl | Miscellaneous | OtherReaction | 4400727cd1198764fe8b1969daa817e812a15f25c8b234ac111afebd28f75e4d | 08ae86020599855ef67800c69886dbf7915f83dafbd43cf0edc5db86fcf85ed8 | O=C1COC(=O)CO1 | Cl-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[O;H0;D2;+0:8]-[OH;D1;+0:9]):[cH;D2;+0:10]:1>>[CH3;D1;+0:3]-[CH2;D2;+0:4]-[C;H0;D4;+0:1]1(-[CH3;D1;+0:10])-[O;H0;D2;+0:8]-[C;H0;D3;+0:6](=[O;H0;D1;+0:9])-[CH2;D2;+0:5]-[#8:11]-[C;H0;D3;+0:2]-1=[O;H0;D1;+0:7] | 75 | [{"value": 75.0, "product": "C(C)C1(OC(COC1=O)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 0.5 g of cyclic keto-ester (3.5 mmol) and 1.21 g of metachloroperbenzoic acid (2 eq.) in 10 ml of dichloromethane is heated under reflux for 48 hours. After returning to ambient temperature, the solvent is eliminated under vacuum. NMR 1H analysis reveals the complete conversion of the ring with 5 members ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide | Ester.Ester | c1ccccc1 | C1COCCO1 | C1COCCO1 | null | ClCCl | null | null | O=C(OO)c1cccc(Cl)c1>ClCCl>CCC1(C)OC(=O)COC1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-68dc893cc621422e8b91a7c12f815dad | BrBr.CC(=O)c1ccc(C(C)(C)C)cc1>>CC(C)(C)c1ccc(C(=O)CBr)cc1 | CC(=O)C1=CC=C(C=C1)C(C)(C)C.BrBr.Br>>BrCC(=O)C1=CC=C(C=C1)C(C)(C)C | Br[Br:12].[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[CH3:11])[cH:13][cH:14]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[CH2:11][Br:12])[cH:13][cH:14]1 | BrBr.CC(=O)c1ccc(C(C)(C)C)cc1 | CC(C)(C)c1ccc(C(=O)CBr)cc1 | null | null | C(C)(=O)O | Functional Group Interconversion | Bromination | 97ca6720945af5a02c450d33ec56e946521050f9771c27f9cfcb85f3477593f6 | cb3e14519230141aa015a4cf9c960def3e60f01997e61621f62506924bfa15de | c1ccccc1 | Br-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[C:3](=[O;D1;H0:4])-[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3](=[O;D1;H0:4])-[c:5] | null | [] | null | null | 4 | HOUR | A solution of 4-tert-butylacetophenone (5 g, 28.4 mmol) in acetic acid (2 mL) was carefully (the reaction was exothermic) treated with Br2 (1.46 mL, 28.5 mmol), followed by 48% aq. HBr (0.015 mL, 0.132 mmol). The reaction was stirred at room temperature for 4 hours, then was poured onto ice and was extracted with dieth... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary halide | null | null | c1ccccc1 | HBr | C(C)(=O)O | null | 4 | BrBr.CC(=O)c1ccc(C(C)(C)C)cc1>C(C)(=O)O>CC(C)(C)c1ccc(C(=O)CBr)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5d6baec4e8404978a184d19e768cdbb6 | CC(C)(C)c1ccc(C(=O)CBr)cc1.[N-]=[N+]=[N-]>>CC(C)(C)c1ccc(C(=O)CN=[N+]=[N-])cc1 | [Na+].[Cl-].BrCC(=O)C1=CC=C(C=C1)C(C)(C)C.[N-]=[N+]=[N-].[Na+]>>N(=[N+]=[N-])CC(=O)C1=CC=C(C=C1)C(C)(C)C | Br[CH2:11][C:9]([c:8]1[cH:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:16][cH:15]1)=[O:10].[N-:12]=[N+:13]=[N-:14]>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[CH2:11][N:12]=[N+:13]=[N-:14])[cH:15][cH:16]1 | CC(C)(C)c1ccc(C(=O)CBr)cc1.[N-]=[N+]=[N-] | CC(C)(C)c1ccc(C(=O)CN=[N+]=[N-])cc1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 7fe919211b759a1428a74cb1057710661d1d522f092678548e8299963d0e0365 | f47c52494d5e4df5ea8fcd9d0881525b7662fe98ccef006a42d77c12f4514758 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[N-;H0;D1:5]=[#7;+:6]=[N;-;D1;H0:7]>>[N;-;D1;H0:7]=[#7;+:6]=[N;H0;D2;+0:5]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4] | 85.3 | [{"value": 85.0, "product": "N(=[N+]=[N-])CC(=O)C1=CC=C(C=C1)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.3, "product": "N(=[N+]=[N-])CC(=O)C1=CC=C(C=C1)C(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of the product of Example 1A (985 mg, 3.86 mmol) in 45 mL acetone was added NaN3 (0.505 g, 7.07 mmol), and the mixture stirred overnight at room temperature. The reaction mixture was poured into saturated NaCl solution and extracted with dichloromethane. The extracts were washed with saturated NaCl soluti... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ketone.Azide | null | null | c1ccccc1 | Br- | CC(=O)C | null | 8 | CC(C)(C)c1ccc(C(=O)CBr)cc1.[N-]=[N+]=[N-]>CC(=O)C>CC(C)(C)c1ccc(C(=O)CN=[N+]=[N-])cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3cc7c50802ec48e0a693d4bfa31dc99d | CCOc1ccc2cccc(NC(=O)OC(C)(C)C)c2c1>>CCOc1ccc2cccc(N)c2c1 | C(C)OC1=CC=C2C=CC=C(C2=C1)NC(OC(C)(C)C)=O.Cl>>C(C)OC1=CC=C2C=CC=C(C2=C1)N | CC(C)(C)OC(=O)[NH:12][c:11]1[cH:10][cH:9][cH:8][c:7]2[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[cH:14][c:13]21>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]2[cH:8][cH:9][cH:10][c:11]([NH2:12])[c:13]2[cH:14]1 | CCOc1ccc2cccc(NC(=O)OC(C)(C)C)c2c1 | CCOc1ccc2cccc(N)c2c1 | null | null | O1CCOCC1.C(C)OCC | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc2ccccc2c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 52 | [{"value": 52.0, "product": "C(C)OC1=CC=C2C=CC=C(C2=C1)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.7, "product": "C(C)OC1=CC=C2C=CC=C(C2=C1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3.5 | HOUR | To a solution of the product of Example 1C (14.47 g, 50.4 mmol) in dioxane (30 mL) at 0° C. was added 4N HCl in dioxane (60 mL, 240 mmol). The reaction mixture was stirred at room temperature for 3.5 hours, diluted with 3 volumes of diethyl ether. The resulting dark brown precipitate was collected by filtration. It was... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2ccccc2c1 | HO- | O1CCOCC1.C(C)OCC | null | 3.5 | CCOc1ccc2cccc(NC(=O)OC(C)(C)C)c2c1>O1CCOCC1.C(C)OCC>CCOc1ccc2cccc(N)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-11a81ffe826b44e89ced61ff8a22bd07 | CCOc1ccc2cccc(N)c2c1>>CCOC1=CCc2cccc(N)c2C1 | [Li].C(C)OC1=CC=C2C=CC=C(C2=C1)N.C(C)(C)(C)O.N>>C(C)OC1=CCC=2C=CC=C(C2C1)N | [CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]2[cH:8][cH:9][cH:10][c:11]([NH2:12])[c:13]2[cH:14]1>>[CH3:1][CH2:2][O:3][C:4]1=[CH:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][c:11]([NH2:12])[c:13]2[CH2:14]1 | CCOc1ccc2cccc(N)c2c1 | CCOC1=CCc2cccc(N)c2C1 | null | null | O1CCCC1 | Miscellaneous | OtherReaction | 47cfb58d0c1d97c9a88a3f7fa92108ac5ffdcba9a9b8195e99d4dfecb292a8df | bced64702950df7cf56df22d8c2487b007734fece951727fd2c8a1c63fbcf6cc | C1=CCc2ccccc2C1 | [C:1]-[#8:2]-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[c:5](:[c:6]):[c:7](:[c:8]):[cH;D2;+0:9]:[cH;D2;+0:10]:1>>[C:1]-[#8:2]-[C;H0;D3;+0:3]1=[CH;D2;+0:10]-[CH2;D2;+0:9]-[c:7](:[c:8]):[c:5](:[c:6])-[CH2;D2;+0:4]-1 | 55 | [{"value": 55.0, "product": "C(C)OC1=CCC=2C=CC=C(C2C1)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.8, "product": "C(C)OC1=CCC=2C=CC=C(C2C1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 1 | HOUR | The product of Example 1D (1.8 g, 9.63 mmol) and tert-butanol (2.13 g, 28.8 mmol) were dissolved in tetrahydrofuran (20 mL) in a 3-neck 1000 mL round-bottom flask, and the solution was cooled to −78° C. Ammonia (˜35 mL) was condensed into the flask, then lithium metal was added (wire, 225 mg, 32.4 mmol) in portions ove... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Ether | c1ccc2ccccc2c1 | C1=CCc2ccccc2C1 | C1=CCc2ccccc2C1 | null | O1CCCC1 | -78 | 1 | CCOc1ccc2cccc(N)c2c1>O1CCCC1>CCOC1=CCc2cccc(N)c2C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5ba29fd898794ebf8e3230da2c8c99f0 | CCOC1=CCc2cccc(N)c2C1.S=C(Oc1ccccn1)Oc1ccccn1>>CCOC1=CCc2cccc(N=C=S)c2C1 | C(C)OC1=CCC=2C=CC=C(C2C1)N.C(OC1=NC=CC=C1)(OC1=NC=CC=C1)=S>>C(C)OC=1CC2=C(C=CC=C2CC1)N=C=S | [CH3:1][CH2:2][O:3][C:4]1=[CH:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][c:11]([NH2:12])[c:15]2[CH2:16]1.c1ccc(O[C:13](Oc2ccccn2)=[S:14])nc1>>[CH3:1][CH2:2][O:3][C:4]1=[CH:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][c:11]([N:12]=[C:13]=[S:14])[c:15]2[CH2:16]1 | CCOC1=CCc2cccc(N)c2C1.S=C(Oc1ccccn1)Oc1ccccn1 | CCOC1=CCc2cccc(N=C=S)c2C1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | OtherReaction | 9a80968abe70879a9369740fc6263b884e7d64cc7f090788997500a3069df240 | 0bc85fa9e96d94388afe13d389361cafe3d77a7182964e359eefb70b6e8160bc | C1=CCc2ccccc2C1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[S;D1;H0:5]=[C;H0;D3;+0:6](-O-c1:c:c:c:c:n:1)-O-c1:c:c:c:c:n:1>>[S;D1;H0:5]=[C;H0;D2;+0:6]=[N;H0;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 18 | HOUR | A solution of the product of Example 1E (200 mg, 1.06 mmol) in dichloromethane (2.5 mL) was added to a solution of O,O-dipyridin-2-yl thiocarbonate (246 mg, 1.06 mmol) in dichloromethane (5 mL) at room temperature. After stirring at room temperature for 18 hours, the mixture was concentrated, then filtered through sili... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Primary amine.Thiocarbonyl | Isothiocyanate | c1ccncc1.c1ccncc1 | null | C1=CCc2ccccc2C1 | HO- | ClCCl | null | 18 | CCOC1=CCc2cccc(N)c2C1.S=C(Oc1ccccn1)Oc1ccccn1>ClCCl>CCOC1=CCc2cccc(N=C=S)c2C1 |
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