dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5f42e2530e154a3096b9b9ddf20e8732 | BrP(Br)Br.CC(C)(C)OC(=O)n1ccc2c(CO)cccc21>>CC(C)(C)OC(=O)n1ccc2c(CBr)cccc21 | P(Br)(Br)Br.C(=O)(OC(C)(C)C)N1C=CC2=C(C=CC=C12)CO.C(=O)(O)[O-].[Na+]>>BrCC1=C2C=CN(C2=CC=C1)C(=O)OC(C)(C)C | BrP(Br)[Br:14].O[CH2:13][c:12]1[c:11]2[cH:10][cH:9][n:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[c:18]2[cH:17][cH:16][cH:15]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[n:8]1[cH:9][cH:10][c:11]2[c:12]([CH2:13][Br:14])[cH:15][cH:16][cH:17][c:18]12 | BrP(Br)Br.CC(C)(C)OC(=O)n1ccc2c(CO)cccc21 | CC(C)(C)OC(=O)n1ccc2c(CBr)cccc21 | null | null | C(Cl)Cl.CCOCC | Functional Group Interconversion | PBr3 and alcohol to alkyl bromide | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | c1ccc2[nH]ccc2c1 | Br-P(-Br)-[Br;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]:[c:6]:[#7;a:7]>>[#7;a:7]:[c:6]:[c:5]:[c:3](-[CH2;D2;+0:2]-[Br;H0;D1;+0:1]):[c:4] | 84 | [{"value": 84.0, "product": "BrCC1=C2C=CN(C2=CC=C1)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.6, "product": "BrCC1=C2C=CN(C2=CC=C1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | PBr3 (2.4 mL. 25.8 mmol) was added dropwise at 0° C. under nitrogen to a stirred solution of tert-butyl 4-(hydroxymethyl) 1H-1-indolecarboxylate 6 (6.0 g, 24.3 mmol) in ether (80 mL) and CH2Cl2 (20 mL) under nitrogen. The reaction was completed 30 minutes after the addition. The mixture was poured into a cold aqueous N... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1cccc2[nH]ccc12 | HBr | C(Cl)Cl.CCOCC | null | 0.5 | BrP(Br)Br.CC(C)(C)OC(=O)n1ccc2c(CO)cccc21>C(Cl)Cl.CCOCC>CC(C)(C)OC(=O)n1ccc2c(CBr)cccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7e08ad6461e04781b376d6f3d0f83053 | CC(C)(C)OC(=O)N1CCC(C=O)C1>>C=CC1CCN(C(=O)OC(C)(C)C)C1 | C(C)(C)(C)OC(=O)N1CC(CC1)C=O.C(CCC)[Li].[Br-].C1(=CC=CC=C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)[PH3+].[Cl-].[NH4+]>>C(C)(C)(C)OC(=O)N1CC(CC1)C=C | O=[CH:2][CH:3]1[CH2:4][CH2:5][N:6]([C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[CH2:14]1>>[CH2:1]=[CH:2][CH:3]1[CH2:4][CH2:5][N:6]([C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[CH2:14]1 | CC(C)(C)OC(=O)N1CCC(C=O)C1 | C=CC1CCN(C(=O)OC(C)(C)C)C1 | null | null | C(C)(=O)OCC.O1CCCC1.CCCCCC | Functional Group Interconversion | OtherReaction | dd6fb167b4e71f3ea190d18ad4e87d18c641d879b83b47beb9dc06bc791584b1 | 6b3ec9b506a5bb4882685e77a1e07fcb518f891061dfbc2d36767289330c841e | C1CCNC1 | O=[CH;D2;+0:1]-[C:2](-[C:3])-[C:4]-[#7:5]>>[#7:5]-[C:4]-[C:2](-[CH;D2;+0:1]=[C;D1;H2:6])-[C:3] | 89.7 | [{"value": 89.7, "product": "C(C)(C)(C)OC(=O)N1CC(CC1)C=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 0.5 | HOUR | n-Butyllithium in hexane (44 cm3 of a 1.6 N solution) was added drop-wise to a suspension of 25.5 g (71 mmol) of triphenylmethylphosphonium bromide in 300 cm3 of tetrahydrofuran, which was under argon and cooled to 0° C. The reaction mixture was stirred at 0° C. for 0.5 h and then admixed with a solution of 7.1 g (35.6... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Vinyl | null | null | C1CC[NH]C1 | null | C(C)(=O)OCC.O1CCCC1.CCCCCC | 0 | 0.5 | CC(C)(C)OC(=O)N1CCC(C=O)C1>C(C)(=O)OCC.O1CCCC1.CCCCCC>C=CC1CCN(C(=O)OC(C)(C)C)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ada3a438f89c4bfbbbdb163094b9a1cc | NCCC1=CC=C(O)C(O)C1>>NCCc1ccc(O)c(O)c1 | NCCC=1CC(O)C(O)=CC1.N1=CC=CC(=C1)C1N(C)CCC1>>NCCC1=CC(O)=C(O)C=C1 | [NH2:1][CH2:2][CH2:3][C:4]1=[CH:5][CH:6]=[C:7]([OH:8])[CH:9]([OH:10])[CH2:11]1>>[NH2:1][CH2:2][CH2:3][c:4]1[cH:5][cH:6][c:7]([OH:8])[c:9]([OH:10])[cH:11]1 | NCCC1=CC=C(O)C(O)C1 | NCCc1ccc(O)c(O)c1 | null | null | null | Miscellaneous | OtherReaction | d72dc877dbda7d080b263ebc2b8cd165e38d60ff56a667714eb8e3aa080aed81 | ef49430386e4c58f0f103ac84bb7f8be7a7fcba093512db68d8ff45186c8f6c2 | c1ccccc1 | [C:1]-[C:2]-[C;H0;D3;+0:3]1=[CH;D2;+0:4]-[CH;D2;+0:5]=[C;H0;D3;+0:6](-[O;D1;H1:7])-[CH;D3;+0:8](-[O;D1;H1:9])-[CH2;D2;+0:10]-1>>[C:1]-[C:2]-[c;H0;D3;+0:3]1:[cH;D2;+0:10]:[c;H0;D3;+0:8](-[O;D1;H1:9]):[c;H0;D3;+0:6](-[O;D1;H1:7]):[cH;D2;+0:5]:[cH;D2;+0:4]:1 | null | [] | null | null | 10 | MINUTE | The synaptosomal suspension was incubated for 10 minutes at 37° C. to restore metabolic activity. [3H]Dopamine ([3H]DA, specific activity=28.0 Ci/mmol, NEN Research Products) was added at a final concentration of 0.1 μM and the suspension was incubated at 37° C. for another 10 minutes. 50 μL aliquots of tissue +100 μL ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Enol.Conjugated diene | Aromatic alcohol.Aromatic alcohol | C1=CCCC=C1 | c1ccccc1 | c1ccccc1 | null | null | null | 0.166667 | NCCC1=CC=C(O)C(O)C1>>NCCc1ccc(O)c(O)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-328e756752e84921bd9155ec1c1ac88c | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccco1.Clc1nc(Cl)c2ccnc-2[nH]1>>Clc1nc(-c2ccco2)c2ccnc-2[nH]1 | ClC1=NC(=C2C(N1)=NC=C2)Cl.C(CCC)[Sn](C=1OC=CC1)(CCCC)CCCC>>ClC1=NC(=C2C(N1)=NC=C2)C=2OC=CC2 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:5]1[cH:6][cH:7][cH:8][o:9]1.Cl[c:4]1[n:3][c:2]([Cl:1])[nH:15][c:14]2[n:13][cH:12][cH:11][c:10]1-2>>[Cl:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][o:9]2)[c:10]2[cH:11][cH:12][n:13][c:14]-2[nH:15]1 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccco1.Clc1nc(Cl)c2ccnc-2[nH]1 | Clc1nc(-c2ccco2)c2ccnc-2[nH]1 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | C(C)OCC.CN(C)C=O | C-C Coupling | Stille reaction_aryl | 6aa8c09d3c0407c9aaf6499bf289fd57fe4b1f52b9fee773c7ce50acce18771d | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | c1coc(-c2nc[nH]c3nccc2-3)c1 | C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:1]1:[#8;a:2]:[c:3]:[c:4]:[c:5]:1.Cl-[c;H0;D3;+0:6]1:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]2:[#7;a:11]:[c:12]:[c:13]:[c:14]:1-2>>[#7;a:11]1:[c:12]:[c:13]:[c:14]2:[c;H0;D3;+0:6](-[c;H0;D3;+0:1]3:[#8;a:2]:[c:3]:[c:4]:[c:5]:3):[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:1-2 | 61.4 | [{"value": 61.0, "product": "ClC1=NC(=C2C(N1)=NC=C2)C=2OC=CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.4, "product": "ClC1=NC(=C2C(N1)=NC=C2)C=2OC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A solution of 2,4-dichloro-1H-pyrrolo[2,3-d]pyrimidine (4.1 g, 21.8 mmol) in DMF (20 mL) was treated with PdCl2(PPh3)2 (772 mg, 0.17 mmol) and 2-(tributylstannyl)-furan (6.9 mL, 21.8 mmol), stirred at room temperature for 16 h, diluted with diethyl ether and filtered to give the title compound (2.94 g, 61%) as a pale o... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1ccoc1.c1ncc2cc[nH]c2n1 | c1ccoc1.c1ncc2cc[nH]c2n1 | c1ccoc1.c1ncc2cc[nH]c2n1 | HCl.Sn | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.C(C)OCC.CN(C)C=O | null | 16 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccco1.Clc1nc(Cl)c2ccnc-2[nH]1>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.C(C)OCC.CN(C)C=O>Clc1nc(-c2ccco2)c2ccnc-2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-13d810c18f0c45ee97e9e518ee55d635 | Clc1nc(-c2ccco2)c2ccnc-2[nH]1.Fc1ccccc1CBr>>Fc1ccccc1Cn1ccc2c(-c3ccco3)nc(Cl)nc21 | FC1=C(CBr)C=CC=C1.ClC1=NC(=C2C(N1)=NC=C2)C=2OC=CC2.[H-].[Na+]>>ClC=1N=C(C2=C(N1)N(C=C2)CC2=C(C=CC=C2)F)C=2OC=CC2 | [n:9]1[cH:10][cH:11][c:12]2[c:13](-[c:14]3[cH:15][cH:16][cH:17][o:18]3)[n:19][c:20]([Cl:21])[nH:22][c:23]1-2.Br[CH2:8][c:7]1[c:2]([F:1])[cH:3][cH:4][cH:5][cH:6]1>>[F:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[CH2:8][n:9]1[cH:10][cH:11][c:12]2[c:13](-[c:14]3[cH:15][cH:16][cH:17][o:18]3)[n:19][c:20]([Cl:21])[n:22][c:23]12 | Clc1nc(-c2ccco2)c2ccnc-2[nH]1.Fc1ccccc1CBr | Fc1ccccc1Cn1ccc2c(-c3ccco3)nc(Cl)nc21 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | edd5857a15d7b36c5d4505944cd0264d067ed458a95f422fadba87dda59a933b | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cn2ccc3c(-c4ccco4)ncnc32)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#8;a:5]:[c:6]-[c:7]1:[#7;a:8]:[c:9](-[Cl;D1;H0:10]):[nH;D2;+0:11]:[c;H0;D3;+0:12]2:[n;H0;D2;+0:13]:[c:14]:[c:15]:[c;H0;D3;+0:16]:1-2>>[#8;a:5]:[c:6]-[c:7]1:[#7;a:8]:[c:9](-[Cl;D1;H0:10]):[n;H0;D2;+0:11]:[c;H0;D3;+0:12]2:[c;H0;D3;+0:16]:1:[c:15]:[c:14]:[n;H0;D3;+0:13]:2-[CH2;D2;+0:1... | 76.3 | [{"value": 76.0, "product": "ClC=1N=C(C2=C(N1)N(C=C2)CC2=C(C=CC=C2)F)C=2OC=CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.3, "product": "ClC=1N=C(C2=C(N1)N(C=C2)CC2=C(C=CC=C2)F)C=2OC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | A solution of 2-chloro-4-(2-furyl)-1H-pyrrolo[2,3-d]pyrimidine (219 mg, 1 mmol) in DMF (2 mL) at 0° C. was treated with NaH (40 mg, 60%, 1 mmol), stirred for 20 min, treated with 2-fluorobenzyl bromide (120 μL, 1 mmol), stirred at room temperature for 1 h, quenched with water, extracted with EtOAc, dried (MgSO4), conce... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2cc[nH]c2n1 | c1ncc2cc[nH]c2n1 | c1ccccc1.c1ccoc1.c1ncc2cc[nH]c2n1 | HBr | CN(C)C=O | null | 0.333333 | Clc1nc(-c2ccco2)c2ccnc-2[nH]1.Fc1ccccc1CBr>CN(C)C=O>Fc1ccccc1Cn1ccc2c(-c3ccco3)nc(Cl)nc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-24ae2260c3ff44c886402ed1bd64b0dd | COc1ccc(CN)cc1OC.Fc1ccccc1Cn1ccc2c(-c3ccco3)nc(Cl)nc21>>COc1ccc(CNc2nc(-c3ccco3)c3ccn(Cc4ccccc4F)c3n2)cc1OC | ClC=1N=C(C2=C(N1)N(C=C2)CC2=C(C=CC=C2)F)C=2OC=CC2.C(C1=CC(OC)=C(OC)C=C1)N>>COC=1C=C(CNC=2N=C(C3=C(N2)N(C=C3)CC3=C(C=CC=C3)F)C=3OC=CC3)C=CC1OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][NH2:8])[cH:31][c:32]1[O:33][CH3:34].Cl[c:9]1[n:10][c:11](-[c:12]2[cH:13][cH:14][cH:15][o:16]2)[c:17]2[cH:18][cH:19][n:20]([CH2:21][c:22]3[cH:23][cH:24][cH:25][cH:26][c:27]3[F:28])[c:29]2[n:30]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][NH:8][c:9]2[n:10][c:11](-[c:12]3[cH:1... | COc1ccc(CN)cc1OC.Fc1ccccc1Cn1ccc2c(-c3ccco3)nc(Cl)nc21 | COc1ccc(CNc2nc(-c3ccco3)c3ccn(Cc4ccccc4F)c3n2)cc1OC | null | null | CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 7d8cc6c05eda9dfa6bdabe6a29061e2976ad8c7049d801bee87af917df08c113 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2nc(-c3ccco3)c3ccn(Cc4ccccc4)c3n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:1):[#7;a:7](-[C:8]):[c:9].[NH2;D1;+0:10]-[C:11]-[c:12]>>[C:8]-[#7;a:7](:[c:9]):[c:5]1:[#7;a:6]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[C:11]-[c:12]):[#7;a:2]:[c:3]:[c:4]:1 | 88.4 | [{"value": 88.0, "product": "COC=1C=C(CNC=2N=C(C3=C(N2)N(C=C3)CC3=C(C=CC=C3)F)C=3OC=CC3)C=CC1OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.4, "product": "COC=1C=C(CNC=2N=C(C3=C(N2)N(C=C3)CC3=C(C=CC=C3)F)C=3OC=CC3)C=CC1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A solution of 2-chloro-7-(2-fluorobenzyl)4(2-furyl)-7H-pyrrolo[2,3-d]pyrimidine (254 mg, 0.78 mmol) in N-methylpyrrolidone (2 mL) was treated with veratrylamine (0.25 mL, 1.66 mmol), heated to 100° C. for 16 h and purified by chromatography (Heptane:EtOAc, 4:1) to give the title compound (316 mg, 88%) as a cream solid.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncc2cc[nH]c2n1 | c1ncc2cc[nH]c2n1 | c1ccccc1.c1ccoc1.c1ncc2cc[nH]c2n1.c1ccccc1 | HCl | CN1C(CCC1)=O | 100 | null | COc1ccc(CN)cc1OC.Fc1ccccc1Cn1ccc2c(-c3ccco3)nc(Cl)nc21>CN1C(CCC1)=O>COc1ccc(CNc2nc(-c3ccco3)c3ccn(Cc4ccccc4F)c3n2)cc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-33bf0de3f8aa48d1816747caea2ecde9 | COc1ccc(CNc2nc(-c3ccco3)c3ccn(Cc4ccccc4F)c3n2)cc1OC>>Nc1nc(-c2ccco2)c2ccn(Cc3ccccc3F)c2n1 | COC=1C=C(CNC=2N=C(C3=C(N2)N(C=C3)CC3=C(C=CC=C3)F)C=3OC=CC3)C=CC1OC>>FC1=C(CN2C=CC3=C2N=C(N=C3C=3OC=CC3)N)C=CC=C1 | COc1ccc(C[NH:1][c:2]2[n:3][c:4](-[c:5]3[cH:6][cH:7][cH:8][o:9]3)[c:10]3[cH:11][cH:12][n:13]([CH2:14][c:15]4[cH:16][cH:17][cH:18][cH:19][c:20]4[F:21])[c:22]3[n:23]2)cc1OC>>[NH2:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][o:9]2)[c:10]2[cH:11][cH:12][n:13]([CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[F:21])[c:22]2[... | COc1ccc(CNc2nc(-c3ccco3)c3ccn(Cc4ccccc4F)c3n2)cc1OC | Nc1nc(-c2ccco2)c2ccn(Cc3ccccc3F)c2n1 | null | null | C(=O)(C(F)(F)F)O | Reduction | OtherReaction | 93295f0bc4e4cc47e665b12bc7fe58c9728c9fb915c15424d06f1616b6912002 | 9fb4bdd681eea7aeb7e37bbfb0aa4538a773561d0c8ffc2bcfecd748c2197589 | c1ccc(Cn2ccc3c(-c4ccco4)ncnc32)cc1 | C-O-c1:c:c:c(-C-[NH;D2;+0:1]-[c:2](:[#7;a:3]:[c:4]:[#7;a:5]):[#7;a:6]:[c:7]):c:c:1-O-C>>[#7;a:5]:[c:4]:[#7;a:3]:[c:2](-[NH2;D1;+0:1]):[#7;a:6]:[c:7] | 51.4 | [{"value": 51.0, "product": "FC1=C(CN2C=CC3=C2N=C(N=C3C=3OC=CC3)N)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.4, "product": "FC1=C(CN2C=CC3=C2N=C(N=C3C=3OC=CC3)N)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of N-(3,4-dimethoxybenzyl)-7-(2-fluorobenzyl)4-(2-furyl)-7H-pyrrolo[2,3-d]pyrimidine-2-amine (110 mg, 0.24 mmol) in TFA (1 mL) was heated to 50° C. for 3 h, concentrated in vacuo, treated with saturated NaHCO3, extracted with EtOAc, dried (MgSO4), concentrated in vacuo, purified by chromatography (EtOAc:Hept... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Secondary amine | Primary amine | c1ccccc1 | null | c1ccoc1.c1ncc2cc[nH]c2n1.c1ccccc1 | HO- | C(=O)(C(F)(F)F)O | null | null | COc1ccc(CNc2nc(-c3ccco3)c3ccn(Cc4ccccc4F)c3n2)cc1OC>C(=O)(C(F)(F)F)O>Nc1nc(-c2ccco2)c2ccn(Cc3ccccc3F)c2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a071ae83731e44dba70337a8f6a9c26b | CN(C)c1nc(-c2ccco2)c2ccnc-2[nH]1.O=C(Cl)c1ccccc1>>CN(C)c1nc(-c2ccco2)c2ccn(C(=O)c3ccccc3)c2n1 | CN(C1=NC(=C2C(N1)=NC=C2)C=2OC=CC2)C.CCN(CC)CC.C(C1=CC=CC=C1)(=O)Cl>>C(C1=CC=CC=C1)(=O)N1C=CC2=C1N=C(N=C2C=2OC=CC2)N(C)C | [CH3:1][N:2]([CH3:3])[c:4]1[n:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][o:11]2)[c:12]2[cH:13][cH:14][n:15][c:24]-2[nH:25]1.Cl[C:16](=[O:17])[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][N:2]([CH3:3])[c:4]1[n:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][o:11]2)[c:12]2[cH:13][cH:14][n:15]([C:16](=[O:17])[c:18]3[cH:19][cH:20][cH:21... | CN(C)c1nc(-c2ccco2)c2ccnc-2[nH]1.O=C(Cl)c1ccccc1 | CN(C)c1nc(-c2ccco2)c2ccn(C(=O)c3ccccc3)c2n1 | null | CN(C)C=1C=CN=CC1 | C1CCOC1 | Acylation | OtherReaction | 138010d210cab22bc5a9617aec89dab5412792532bc7ffbfd582354a2e40c660 | edbcca52d877d662e04f0d6de1a7107a8eca1d366ee6da0d92e37eb02a291876 | O=C(c1ccccc1)n1ccc2c(-c3ccco3)ncnc21 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7:6]-[c:7]1:[#7;a:8]:[c:9](-[c:10]:[#8;a:11]):[c;H0;D3;+0:12]2:[c:13]:[c:14]:[n;H0;D2;+0:15]:[c;H0;D3;+0:16]-2:[nH;D2;+0:17]:1>>[#7:6]-[c:7]1:[#7;a:8]:[c:9](-[c:10]:[#8;a:11]):[c;H0;D3;+0:12]2:[c:13]:[c:14]:[n;H0;D3;+0:15](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4])... | 28.6 | [{"value": 28.6, "product": "C(C1=CC=CC=C1)(=O)N1C=CC2=C1N=C(N=C2C=2OC=CC2)N(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of N,N-dimethyl-4-(2-furyl)-1H-pyrrolo[2,3-d]pyrimidine-2-amine (181 mg, 0.8 mmol) in THF (3 mL) was treated with Et3N, (111 μL, 0.8 mmol), benzoyl chloride (93 μL, 0.8 mmol) and a catalytic amount of DMAP, stirred at room temperature for 16 h, quenched with water, extracted with EtOAc, dried (MgSO4), concen... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | null | c1ncc2cc[nH]c2n1 | c1ncc2cc[nH]c2n1 | c1ccoc1.c1ncc2cc[nH]c2n1.c1ccccc1 | HCl | CN(C)C=1C=CN=CC1.C1CCOC1 | null | null | CN(C)c1nc(-c2ccco2)c2ccnc-2[nH]1.O=C(Cl)c1ccccc1>CN(C)C=1C=CN=CC1.C1CCOC1>CN(C)c1nc(-c2ccco2)c2ccn(C(=O)c3ccccc3)c2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e3a6e51d909246489019c19083530959 | Nc1nc(-c2ccco2)c2ccnc-2[nH]1.O=C=NCc1ccccc1>>O=C(NCc1ccccc1)Nc1nc(-c2ccco2)c2ccnc-2[nH]1 | O1C(=CC=C1)C1=C2C(NC(=N1)N)=NC=C2.C(C1=CC=CC=C1)N=C=O>>C(C1=CC=CC=C1)NC(=O)NC1=NC(=C2C(N1)=NC=C2)C=2OC=CC2 | [NH2:11][c:12]1[n:13][c:14](-[c:15]2[cH:16][cH:17][cH:18][o:19]2)[c:20]2[cH:21][cH:22][n:23][c:24]-2[nH:25]1.[O:1]=[C:2]=[N:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[NH:11][c:12]1[n:13][c:14](-[c:15]2[cH:16][cH:17][cH:18][o:19]2)[c:20]2[cH:21][cH:2... | Nc1nc(-c2ccco2)c2ccnc-2[nH]1.O=C=NCc1ccccc1 | O=C(NCc1ccccc1)Nc1nc(-c2ccco2)c2ccnc-2[nH]1 | null | null | C1CCOC1 | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCc1ccccc1)Nc1nc(-c2ccco2)c2ccnc-2[nH]1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[#7;a:6]:[c:7].[O;D1;H0:8]=[C;H0;D2;+0:9]=[N;H0;D2;+0:10]-[C:11]-[c:12]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:9](=[O;D1;H0:8])-[NH;D2;+0:10]-[C:11]-[c:12]):[#7;a:6]:[c:7] | 19.1 | [{"value": 19.0, "product": "C(C1=CC=CC=C1)NC(=O)NC1=NC(=C2C(N1)=NC=C2)C=2OC=CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 19.1, "product": "C(C1=CC=CC=C1)NC(=O)NC1=NC(=C2C(N1)=NC=C2)C=2OC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A solution of 4-(2-furyl)-1H-pyrrolo[2,3-d]pyrimidine-2-amine (192 mg, 0.96 mmol) in THF (3 mL) was treated with benzyl isocyanate (118 μL, 0.96 mmol), stirred at room temperature for 16 h and the resulting solid filtered and washed with EtOAc to give the title compound (61 mg, 19%) as a yellow solid.
Conditions: See r... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1ccoc1.c1ncc2cc[nH]c2n1 | null | C1CCOC1 | null | 16 | Nc1nc(-c2ccco2)c2ccnc-2[nH]1.O=C=NCc1ccccc1>C1CCOC1>O=C(NCc1ccccc1)Nc1nc(-c2ccco2)c2ccnc-2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4602b66e6fc3458f9668186fafd743ef | C[Si](C)(C)CCCl.Clc1nc(Cl)c2ccnc-2[nH]1.O>>C[Si](C)(C)CCOCn1ccc2c(Cl)nc(Cl)nc21 | O.C[Si](C)(C)CCCl.ClC1=NC(=C2C(N1)=NC=C2)Cl.[H-].[Na+].CC#N>>ClC=1N=C(C2=C(N1)N(C=C2)COCC[Si](C)(C)C)Cl | Cl[CH2:6][CH2:5][Si:2]([CH3:1])([CH3:3])[CH3:4].[n:9]1[cH:10][cH:11][c:12]2[c:13]([Cl:14])[n:15][c:16]([Cl:17])[nH:18][c:19]1-2.[OH2:7]>>[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][O:7][CH2:8][n:9]1[cH:10][cH:11][c:12]2[c:13]([Cl:14])[n:15][c:16]([Cl:17])[n:18][c:19]12 | C[Si](C)(C)CCCl.Clc1nc(Cl)c2ccnc-2[nH]1.O | C[Si](C)(C)CCOCn1ccc2c(Cl)nc(Cl)nc21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 67c2afc52a9de03aa4479dd8b8b7a3e2e5f335bb0c6d666cea4c2e8ad04772f8 | 62c7c72c35b09d63ca1131e6cd8c0b88a31e29901d660456b77319cfd78354c7 | c1ncc2cc[nH]c2n1 | Cl-[CH2;D2;+0:1]-[C:2]-[#14:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[C;D1;H3:6].[Cl;D1;H0:7]-[c:8]1:[#7;a:9]:[c:10](-[Cl;D1;H0:11]):[nH;D2;+0:12]:[c;H0;D3;+0:13]2:[n;H0;D2;+0:14]:[c:15]:[c:16]:[c;H0;D3;+0:17]:1-2.[OH2;D0;+0:18]>>[C;D1;H3:4]-[#14:3](-[C;D1;H3:5])(-[C;D1;H3:6])-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:18]-[C:19]-[n;H0;D3;... | 104 | [{"value": 104.0, "product": "ClC=1N=C(C2=C(N1)N(C=C2)COCC[Si](C)(C)C)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 2,4-dichloro-1H-pyrrolo[2,3-d]pyrimidine (542 mg, 2.58 mmol) in MeCN (20 mL) was treated with NaH (113 mg, 2.84 mmol), stirred for 1 h, treated with trimethylsilylethyl chloride (502 μL, 2.84 mmol), stirred at room temperature for 3 h, poured into water, extracted with EtOAc, dried (MgSO4) and concentrate... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Ether | c1ncc2cc[nH]c2n1 | c1ncc2cc[nH]c2n1 | c1ncc2cc[nH]c2n1 | null | null | null | 1 | C[Si](C)(C)CCCl.Clc1nc(Cl)c2ccnc-2[nH]1.O>>C[Si](C)(C)CCOCn1ccc2c(Cl)nc(Cl)nc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7c74cc044148410e80873354e55e0c9e | CN(C)c1nc(-c2ccco2)c2ccn(COCC[Si](C)(C)C)c2n1>>CN(C)c1nc(-c2ccco2)c2ccnc-2[nH]1 | O.CN(C=1N=C(C2=C(N1)N(C=C2)COCC[Si](C)(C)C)C=2OC=CC2)C.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>CN(C1=NC(=C2C(N1)=NC=C2)C=2OC=CC2)C | C[Si](C)(C)CCOC[n:15]1[cH:14][cH:13][c:12]2[c:6](-[c:7]3[cH:8][cH:9][cH:10][o:11]3)[n:5][c:4]([N:2]([CH3:1])[CH3:3])[n:17][c:16]21>>[CH3:1][N:2]([CH3:3])[c:4]1[n:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][o:11]2)[c:12]2[cH:13][cH:14][n:15][c:16]-2[nH:17]1 | CN(C)c1nc(-c2ccco2)c2ccn(COCC[Si](C)(C)C)c2n1 | CN(C)c1nc(-c2ccco2)c2ccnc-2[nH]1 | null | null | C1CCOC1 | Reduction | OtherReaction | d7eb80c127bc5b6eb101f8e75644fc9947e9bb2ac217b88e4a795e634b7003a3 | d646edd3b1165ce8eea24b0587d24c565cf6371928b4879100704e7b3cd85ed9 | c1coc(-c2nc[nH]c3nccc2-3)c1 | C-[Si](-C)(-C)-C-C-O-C-[n;H0;D3;+0:1]1:[c:2]:[c:3]:[c;H0;D3;+0:4]2:[c:5](-[c:6]:[#8;a:7]):[#7;a:8]:[c:9](-[#7:10]):[n;H0;D2;+0:11]:[c;H0;D3;+0:12]:2:1>>[#7:10]-[c:9]1:[#7;a:8]:[c:5](-[c:6]:[#8;a:7]):[c;H0;D3;+0:4]2:[c:3]:[c:2]:[n;H0;D2;+0:1]:[c;H0;D3;+0:12]-2:[nH;D2;+0:11]:1 | 21.2 | [{"value": 21.0, "product": "CN(C1=NC(=C2C(N1)=NC=C2)C=2OC=CC2)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 21.2, "product": "CN(C1=NC(=C2C(N1)=NC=C2)C=2OC=CC2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of N,N-dimethyl4-(2-furyl)-7-(2-trimethylsilylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine-2-amine (370 mg, 0.97 mmol) in THF (3 mL) was treated with tetrabutylammonium fluoride (1 ml, 1-M in THF, 1 mmol), refluxed for 36 h, poured into water, extracted with EtOAc, dried (MgSO4), concentrated in vacuo and purif... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Silyl protective group | null | c1ncc2cc[nH]c2n1 | c1ncc2cc[nH]c2n1 | c1ccoc1.c1ncc2cc[nH]c2n1 | HO- | C1CCOC1 | null | null | CN(C)c1nc(-c2ccco2)c2ccn(COCC[Si](C)(C)C)c2n1>C1CCOC1>CN(C)c1nc(-c2ccco2)c2ccnc-2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-91a500af0c324fcda1988389295dd3f8 | CC(=O)c1ccccc1>>O=C(C=Cc1ccccc1)c1ccccc1 | C[O-].[Na+].C(C)(=O)C1=CC=CC=C1>>C1(=CC=CC=C1)C=CC(=O)C1=CC=CC=C1 | [O:1]=[C:2]([CH3:3])[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[O:1]=[C:2]([CH:3]=[CH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | CC(=O)c1ccccc1 | O=C(C=Cc1ccccc1)c1ccccc1 | null | null | C1CCOC1.CO | C-C Coupling | OtherReaction | 56c4f02478b08d261cea23de43f494776c78ec679e7e270a5eda4662f054aad8 | 6c72a64362b644ff7380f8d0c7bdda962edffb1f22535d7f0916fcd367b6b992 | O=C(C=Cc1ccccc1)c1ccccc1 | [CH3;D1;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[c:4])-[CH;D2;+0:1]=[C:5]-[c:6] | null | [] | null | null | 3 | DAY | Reaction of Aldehydes with Wang Resin-bound Acetophenones: Each packet of Acetophenone-Wang resin was transferred to a 250 mL PP bottle, to which a solution of NaOMe (51.2 mmol, 20 eq, 0.25 M) in 50% THF-MeOH (205 mL) and an aldehyde (51.2 mmol, 20 eq, 0.25 M) were added sequentially. After shaking at room temperature ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ketone | null | c1ccccc1 | c1ccccc1.c1ccccc1 | Other | C1CCOC1.CO | null | 72 | CC(=O)c1ccccc1>C1CCOC1.CO>O=C(C=Cc1ccccc1)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-058e86fe19104b3e93276368ff9bb7d7 | C=O.O=c1cc[nH]c(=O)[nH]1>>O=c1[nH]cc(CO)c(=O)[nH]1 | [OH-].[K+].Cl.NO.N1C(=O)NC(=O)C=C1.C=O>>OCC=1C(NC(NC1)=O)=O | [CH2:6]=[O:7].[O:1]=[c:2]1[nH:3][cH:4][cH:5][c:8](=[O:9])[nH:10]1>>[O:1]=[c:2]1[nH:3][cH:4][c:5]([CH2:6][OH:7])[c:8](=[O:9])[nH:10]1 | C=O.O=c1cc[nH]c(=O)[nH]1 | O=c1[nH]cc(CO)c(=O)[nH]1 | null | null | O | C-C Coupling | OtherReaction | 67448c64d4a30a61f5e502af4acf85fb4cc3d0f5db899aa52bfc35f9dce8fff1 | 4396295d899f5d4f5de2e844a80fc7d194b4da158f49df3d2717206b401b59bd | O=c1cc[nH]c(=O)[nH]1 | [CH2;D1;+0:1]=[O;H0;D1;+0:2].[O;D1;H0:3]=[c:4]1:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:[cH;D2;+0:9]:1>>[O;D1;H0:3]=[c:4]1:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:[c;H0;D3;+0:9]:1-[CH2;D2;+0:1]-[OH;D1;+0:2] | 14.5 | [{"value": 14.5, "product": "OCC=1C(NC(NC1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 68 | HOUR | A 2-L, three-necked flask equipped with a mechanical stirrer, thermometer, condenser, and nitrogen-inlet bubbler was charged with uracil (185.0 g, 1650 mmol) (Aldrich), paraformaldehyde (61.50 g, 2050 mmol as formaldehyde) (Aldrich), and a solution of potassium hydroxide (86.9%, 59.95 g, 928.5 mmol) (Aldrich) in water ... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde | Primary alcohol | c1ccncn1 | c1cncnc1 | c1cncnc1 | null | O | null | 68 | C=O.O=c1cc[nH]c(=O)[nH]1>O>O=c1[nH]cc(CO)c(=O)[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c65460f7404d4c359602cdb11f0d47b8 | ClCc1cnc(Cl)nc1Cl.[I-]>>Clc1ncc(CI)c(Cl)n1 | [I-].[Na+].ClC1=NC=C(C(=N1)Cl)CCl>>ClC1=NC=C(C(=N1)Cl)CI | Cl[CH2:6][c:5]1[cH:4][n:3][c:2]([Cl:1])[n:10][c:8]1[Cl:9].[I-:7]>>[Cl:1][c:2]1[n:3][cH:4][c:5]([CH2:6][I:7])[c:8]([Cl:9])[n:10]1 | ClCc1cnc(Cl)nc1Cl.[I-] | Clc1ncc(CI)c(Cl)n1 | null | null | CC(=O)C | Functional Group Interconversion | OtherReaction | e944a2acb95a43a23818321f2ac2f96ba2f2b8d34f52c1cfd1e3802d2403177f | e2ca6f9fe1078a3836d617896a4e5cc310fb155ca459b021e2b549b3e61f1df7 | c1cncnc1 | Cl-[CH2;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[Cl;D1;H0:8].[I-;H0;D0:9]>>[Cl;D1;H0:8]-[c:7]1:[#7;a:6]:[c:5]:[#7;a:4]:[c:3]:[c:2]:1-[CH2;D2;+0:1]-[I;H0;D1;+0:9] | null | [] | null | null | 20 | MINUTE | A 500-mL, round-bottom flask equipped with a magnetic stirrer, condenser, and nitrogen-inlet bubbler was charged with sodium iodide (38.5 g, 256.9 mmol) (Aldrich) and acetone (300 mL). After a clear solution was obtained, 2,4-dichloro-5-(chloromethyl)pyrimidine (50.0 g, 253.2 mmol) (from Example 1b supra) was added in ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Primary halide | null | null | c1cncnc1 | Other | CC(=O)C | null | 0.333333 | ClCc1cnc(Cl)nc1Cl.[I-]>CC(=O)C>Clc1ncc(CI)c(Cl)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1f20269900804e01908b99c9d221b00d | COC(=O)Cc1ccc(OC)cc1.Clc1ncc(CI)c(Cl)n1>>COC(=O)C(Cc1cnc(Cl)nc1Cl)c1ccc(OC)cc1 | ClC1=NC=C(C(=N1)Cl)CI.COC(CC1=CC=C(C=C1)OC)=O.C(C)(C)NC1CCCCC1.C(CCC)[Li]>>COC(C(CC=1C(=NC(=NC1)Cl)Cl)C1=CC=C(C=C1)OC)=O | [CH3:1][O:2][C:3](=[O:4])[CH2:5][c:15]1[cH:16][cH:17][c:18]([O:19][CH3:20])[cH:21][cH:22]1.I[CH2:6][c:7]1[cH:8][n:9][c:10]([Cl:11])[n:12][c:13]1[Cl:14]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8][n:9][c:10]([Cl:11])[n:12][c:13]1[Cl:14])[c:15]1[cH:16][cH:17][c:18]([O:19][CH3:20])[cH:21][cH:22]1 | COC(=O)Cc1ccc(OC)cc1.Clc1ncc(CI)c(Cl)n1 | COC(=O)C(Cc1cnc(Cl)nc1Cl)c1ccc(OC)cc1 | null | null | C(C)(=O)OCC.O1CCCC1 | C-C Coupling | OtherReaction | cce1a125a1ff1ac49e6bca841c71f39abbf2c962f7edb2747b8c98f3307cb502 | 0061a06af9fc64155952582b91b574e4abd8908ca14244f15179c2400b24dd08 | c1ccc(CCc2cncnc2)cc1 | I-[CH2;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[Cl;D1;H0:8].[C;D1;H3:9]-[#8:10]-[C:11](=[O;D1;H0:12])-[CH2;D2;+0:13]-[c:14](:[c:15]):[c:16]>>[C;D1;H3:9]-[#8:10]-[C:11](=[O;D1;H0:12])-[CH;D3;+0:13](-[CH2;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[Cl;D1;H0:8])-[c:14](:[c:15]):[c:16] | null | [] | -78 | CELSIUS | 30 | MINUTE | To a solution of N-isopropylcyclohexylamine (720 mg, 5.0 mmol) (Aldrich) in dry tetrahydrofuran (10 mL) was added n-butyllithium (2.5 M in hexanes, 2.0 mL, 5.0 mmol) (Aldrich) at −78° C. under argon. After 30 minutes, a solution of 4-methoxyphenylacetic acid methyl ester (900 mg, 5.0 mmol) (Aldrich) in tetrahydrofuran ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | null | null | c1cncnc1.c1ccccc1 | HI | C(C)(=O)OCC.O1CCCC1 | -78 | 0.5 | COC(=O)Cc1ccc(OC)cc1.Clc1ncc(CI)c(Cl)n1>C(C)(=O)OCC.O1CCCC1>COC(=O)C(Cc1cnc(Cl)nc1Cl)c1ccc(OC)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4afc1eb06a12450d987aa3451652d5af | COC(=O)C(Cc1cnc(Cl)nc1Cl)c1ccc(OC)cc1.Nc1ccccc1>>COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1ccc(OC)cc1 | COC(C(CC=1C(=NC(=NC1)Cl)Cl)C1=CC=C(C=C1)OC)=O.NC1=CC=CC=C1>>COC(C(CC=1C(=NC(=NC1)NC1=CC=CC=C1)NC1=CC=CC=C1)C1=CC=C(C=C1)OC)=O | Cl[c:10]1[n:9][cH:8][c:7]([CH2:6][CH:5]([C:3]([O:2][CH3:1])=[O:4])[c:27]2[cH:28][cH:29][c:30]([O:31][CH3:32])[cH:33][cH:34]2)[c:19](Cl)[n:18]1.[NH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8][n:9][c:10]([NH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[n:18][c:1... | COC(=O)C(Cc1cnc(Cl)nc1Cl)c1ccc(OC)cc1.Nc1ccccc1 | COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1ccc(OC)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 41f9322ec5df98feb4edb498f4e5a62751ab580c70737ba501d83b4465521e15 | 23c6396faba21bf6c4e9de50557b8d044c1caf35494930558fc3d2ba563143ac | c1ccc(CCc2cnc(Nc3ccccc3)nc2Nc2ccccc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c;H0;D3;+0:3](-Cl):[c:4](-[C:5]):[c:6]:[#7;a:7]:1.[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C:5]-[c:4]1:[c:6]:[#7;a:7]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]):[#7;a:2]:[c;H0;D3;+0:3]:1-[#7:12]-[c:13] | null | [] | 110 | CELSIUS | null | null | A mixture of 3-(2,4-dichloro-pyrimidin-5-yl)-2-(4-methoxy-phenyl)-propionic acid methyl ester (0.54 g, 1.58 mmol) (from Example 1d supra) and aniline (0.67 g, 7.11 mmol) (Aldrich) was heated at 110° C. for 30 minutes. The reaction mixture was washed with hexanes (50 mL×3) and the supernatant was decanted off after each... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine | Secondary amine.Secondary amine | c1cncnc1 | c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | null | 110 | null | COC(=O)C(Cc1cnc(Cl)nc1Cl)c1ccc(OC)cc1.Nc1ccccc1>>COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1ccc(OC)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-72569249a4644535976a717f79b97131 | COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1ccc(OC)cc1>>COc1ccc(C2Cc3cnc(Nc4ccccc4)nc3N(c3ccccc3)C2=O)cc1 | COC(C(CC=1C(=NC(=NC1)NC1=CC=CC=C1)NC1=CC=CC=C1)C1=CC=C(C=C1)OC)=O.S(O)(O)(=O)=O>>COC1=CC=C(C=C1)C1CC2=C(N=C(N=C2)NC2=CC=CC=C2)N(C1=O)C1=CC=CC=C1 | CO[C:29]([CH:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:32][cH:31]1)[CH2:8][c:9]1[cH:10][n:11][c:12]([NH:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[n:20][c:21]1[NH:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1)=[O:30]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]2[CH2:8][c:9]3[cH:10][n:11][c:12]([NH:13][c:14]4[cH:... | COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1ccc(OC)cc1 | COc1ccc(C2Cc3cnc(Nc4ccccc4)nc3N(c3ccccc3)C2=O)cc1 | null | null | C(C)(=O)O.C(C)(=O)OCC | Miscellaneous | OtherReaction | 4c156791040233b925f911d2344eae0f4fe404d66aa7be29ecbd3d34ec58b9ee | 9fb754180ed1affe0187ff01b0205aba264dc674a9ca4b55d9d8c90d1514940e | O=C1C(c2ccccc2)Cc2cnc(Nc3ccccc3)nc2N1c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[c:4])-[C:5]-[c:6]1:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1-[NH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[C:3](-[c:4])-[C:5]-[c:6]2:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:2-[N;H0;D3;+0:12]-1-[c:13](:[c:14]):[c:15] | null | [] | 80 | CELSIUS | null | null | To the solution of 3-(2,4-diphenylamino-pyrimidin-5-yl)-2-(4-methoxy-phenyl)-propionic acid methyl ester (227.3 mg, 0.5 mmol) (from Example 1e supra) in glacial acetic acid (15 mL) was added concentrated sulfuric acid (0.2 mL) in one portion. The reaction mixture was heated at 80° C. overnight. The reaction mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Tertiary amide | null | c1ncc2c(n1)[NH]CCC2 | c1ccccc1.c1ncc2c(n1)[NH]CCC2.c1ccccc1.c1ccccc1 | HO- | C(C)(=O)O.C(C)(=O)OCC | 80 | null | COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1ccc(OC)cc1>C(C)(=O)O.C(C)(=O)OCC>COc1ccc(C2Cc3cnc(Nc4ccccc4)nc3N(c3ccccc3)C2=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c522ce02ad534b87ac0c7d472d464fbf | COC(=O)Cc1c(Cl)cccc1Cl.Clc1ncc(CI)c(Cl)n1>>COC(=O)C(Cc1cnc(Cl)nc1Cl)c1c(Cl)cccc1Cl | COC(CC1=C(C=CC=C1Cl)Cl)=O.ClC1=NC=C(C(=N1)Cl)CI.C(C)(C)NC1CCCCC1.C(CCC)[Li]>>COC(C(CC=1C(=NC(=NC1)Cl)Cl)C1=C(C=CC=C1Cl)Cl)=O | [CH3:1][O:2][C:3](=[O:4])[CH2:5][c:15]1[c:16]([Cl:17])[cH:18][cH:19][cH:20][c:21]1[Cl:22].I[CH2:6][c:7]1[cH:8][n:9][c:10]([Cl:11])[n:12][c:13]1[Cl:14]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8][n:9][c:10]([Cl:11])[n:12][c:13]1[Cl:14])[c:15]1[c:16]([Cl:17])[cH:18][cH:19][cH:20][c:21]1[Cl:22] | COC(=O)Cc1c(Cl)cccc1Cl.Clc1ncc(CI)c(Cl)n1 | COC(=O)C(Cc1cnc(Cl)nc1Cl)c1c(Cl)cccc1Cl | null | null | C(C)(=O)OCC.O1CCCC1 | C-C Coupling | OtherReaction | cce1a125a1ff1ac49e6bca841c71f39abbf2c962f7edb2747b8c98f3307cb502 | 0061a06af9fc64155952582b91b574e4abd8908ca14244f15179c2400b24dd08 | c1ccc(CCc2cncnc2)cc1 | I-[CH2;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[Cl;D1;H0:8].[C;D1;H3:9]-[#8:10]-[C:11](=[O;D1;H0:12])-[CH2;D2;+0:13]-[c:14](:[c:15]):[c:16]>>[C;D1;H3:9]-[#8:10]-[C:11](=[O;D1;H0:12])-[CH;D3;+0:13](-[CH2;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[Cl;D1;H0:8])-[c:14](:[c:15]):[c:16] | null | [] | -78 | CELSIUS | 30 | MINUTE | To a solution of N-isopropylcyclohexylamine (1.44 g, 10.0 mmol) (Aldrich) in dry tetrahydrofuran (20 mL) was added n-butyllithium (2.5 M in hexanes, 4.0 mL, 10.0 mmol) (Aldrich) at −78° C. under argon. After 30 minutes, a solution of 2,6-dichloro-phenylacetic acid methyl ester (2.19 g, 10.0 mmol) (TCI-US) in tetrahydro... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | null | null | c1cncnc1.c1ccccc1 | HI | C(C)(=O)OCC.O1CCCC1 | -78 | 0.5 | COC(=O)Cc1c(Cl)cccc1Cl.Clc1ncc(CI)c(Cl)n1>C(C)(=O)OCC.O1CCCC1>COC(=O)C(Cc1cnc(Cl)nc1Cl)c1c(Cl)cccc1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a348e451808443f4981f4358045c1ae5 | COC(=O)C(Cc1cnc(Cl)nc1Cl)c1c(Cl)cccc1Cl.Nc1ccccc1>>COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1c(Cl)cccc1Cl | COC(C(CC=1C(=NC(=NC1)Cl)Cl)C1=C(C=CC=C1Cl)Cl)=O.NC1=CC=CC=C1>>COC(C(CC=1C(=NC(=NC1)NC1=CC=CC=C1)NC1=CC=CC=C1)C1=C(C=CC=C1Cl)Cl)=O | Cl[c:10]1[n:9][cH:8][c:7]([CH2:6][CH:5]([C:3]([O:2][CH3:1])=[O:4])[c:27]2[c:28]([Cl:29])[cH:30][cH:31][cH:21][c:33]2[Cl:34])[c:19](Cl)[n:18]1.[NH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8][n:9][c:10]([NH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[n:18][c:19... | COC(=O)C(Cc1cnc(Cl)nc1Cl)c1c(Cl)cccc1Cl.Nc1ccccc1 | COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1c(Cl)cccc1Cl | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 5915cc0a526f64cbddc143c41954b5b125975e4d919e164608d5a11a413b76fc | 45ae7d7d2972e3a9d0ff628eb6c7e0cac8c3e39c85da29f5c6439797c3fe97a5 | c1ccc(CCc2cnc(Nc3ccccc3)nc2Nc2ccccc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c;H0;D3;+0:3](-Cl):[c:4](-[C:5]-[C:6](-[C:7](-[#8:8])=[O;D1;H0:9])-[c:10]2:[c:11]:[c:12]:[cH;D2;+0:13]:[cH;D2;+0:14]:[c;H0;D3;+0:15]:2-[Cl;D1;H0:16]):[c:17]:[#7;a:18]:1.[NH2;D1;+0:19]-[c:20](:[c:21]):[c:22]>>[#8:8]-[C:7](=[O;D1;H0:9])-[C:6](-[C:5]-[c:4]1:[c:17]:[#7;a:18]:[c;H0;D3;+0:1](-[NH... | null | [] | 110 | CELSIUS | null | null | A mixture of 2-(2,6-dichloro-phenyl)-3-(2,4-dichloro-pyrimidin-5-yl)-propionic acid methyl ester (0.20 g, 0.53 mmol) (from Example 2a supra) and aniline (2.0 ml) (Aldrich) was heated at 110° C. for 2 hours. The reaction mixture was washed with hexanes (50 mL×3) and the supernatant was decanted off after each time. The ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Primary amine | Aromatic halide.Secondary amine.Secondary amine | c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1.c1ccccc1 | c1cncnc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | null | 110 | null | COC(=O)C(Cc1cnc(Cl)nc1Cl)c1c(Cl)cccc1Cl.Nc1ccccc1>>COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1c(Cl)cccc1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2ff6d305ccb84e36a219e0e4e3c0ef09 | COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1c(Cl)cccc1Cl>>O=C1C(c2c(Cl)cccc2Cl)Cc2cnc(Nc3ccccc3)nc2N1c1ccccc1 | COC(C(CC=1C(=NC(=NC1)NC1=CC=CC=C1)NC1=CC=CC=C1)C1=C(C=CC=C1Cl)Cl)=O.S(O)(O)(=O)=O>>ClC1=C(C(=CC=C1)Cl)C1CC2=C(N=C(N=C2)NC2=CC=CC=C2)N(C1=O)C1=CC=CC=C1 | CO[C:2](=[O:1])[CH:3]([c:4]1[c:5]([Cl:6])[cH:7][cH:8][cH:9][c:10]1[Cl:11])[CH2:12][c:13]1[cH:14][n:15][c:16]([NH:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[n:24][c:25]1[NH:26][c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1>>[O:1]=[C:2]1[CH:3]([c:4]2[c:5]([Cl:6])[cH:7][cH:8][cH:9][c:10]2[Cl:11])[CH2:12][c:13]2[cH:14][n... | COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1c(Cl)cccc1Cl | O=C1C(c2c(Cl)cccc2Cl)Cc2cnc(Nc3ccccc3)nc2N1c1ccccc1 | null | null | C(C)(=O)O.C(C)(=O)OCC | Miscellaneous | OtherReaction | 4c156791040233b925f911d2344eae0f4fe404d66aa7be29ecbd3d34ec58b9ee | 9fb754180ed1affe0187ff01b0205aba264dc674a9ca4b55d9d8c90d1514940e | O=C1C(c2ccccc2)Cc2cnc(Nc3ccccc3)nc2N1c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[c:4])-[C:5]-[c:6]1:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1-[NH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[C:3](-[c:4])-[C:5]-[c:6]2:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:2-[N;H0;D3;+0:12]-1-[c:13](:[c:14]):[c:15] | null | [] | 145 | CELSIUS | null | null | To a solution of 3-(2,4-diphenylamino-pyrimidin-5-yl)-2-(2,6-dichloro-phenyl)-propionic acid methyl ester (0.18 g, 0.36 mmol) (from Example 2b supra) in glacial acetic acid (2 mL) was added concentrated sulfuric acid (0.1 mL) in one portion. The reaction mixture was heated at 135° C. overnight and 145° C. for another 4... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Tertiary amide | null | c1ncc2c(n1)[NH]CCC2 | c1ccccc1.c1ncc2c(n1)[NH]CCC2.c1ccccc1.c1ccccc1 | HO- | C(C)(=O)O.C(C)(=O)OCC | 145 | null | COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1c(Cl)cccc1Cl>C(C)(=O)O.C(C)(=O)OCC>O=C1C(c2c(Cl)cccc2Cl)Cc2cnc(Nc3ccccc3)nc2N1c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-22aae1a312904b26991097295d0ce830 | CO.COc1cc(CC(=O)O)cc(OC)c1>>COC(=O)Cc1cc(OC)cc(OC)c1 | COC=1C=C(C=C(C1)OC)CC(=O)O.S(O)(O)(=O)=O.CO>>COC(CC1=CC(=CC(=C1)OC)OC)=O | O[CH3:1].[OH:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][c:8]([O:9][CH3:10])[cH:11][c:12]([O:13][CH3:14])[cH:15]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][c:8]([O:9][CH3:10])[cH:11][c:12]([O:13][CH3:14])[cH:15]1 | CO.COc1cc(CC(=O)O)cc(OC)c1 | COC(=O)Cc1cc(OC)cc(OC)c1 | null | null | null | Heteroatom Alkylation and Arylation | Esterification of Carboxylic Acids | 961bfcd5802efbb4a2d5a1e38cbfb6654b5b78f769c3570df49b858a6f105ab6 | 0a622556a49b258b9020bd3a5bdd1fa9237e7093cf9b09de3a6b575ffe935dcd | c1ccccc1 | O-[CH3;D1;+0:1].[C:2]-[C:3](=[O;D1;H0:4])-[OH;D1;+0:5]>>[C:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[CH3;D1;+0:1] | null | [] | null | null | null | null | To a solution of 3,5-dimethoxyphenylacetic acid (1.99 g, 10.0 mmol) (Transworld) in methanol (20 mL) was added concentrated sulfuric acid (1.0 mL) and the reaction mixture was heated at reflux for 24 hours. The reaction mixture was concentrated in vacuo. The residue was then diluted with ethyl acetate (100 mL) and succ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1 | HO- | null | null | null | CO.COc1cc(CC(=O)O)cc(OC)c1>>COC(=O)Cc1cc(OC)cc(OC)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ccebbc825e74486f8f8653f180c27aab | COC(=O)Cc1cc(OC)cc(OC)c1.Clc1ncc(CI)c(Cl)n1>>COC(=O)C(Cc1cnc(Cl)nc1Cl)c1cc(OC)cc(OC)c1 | ClC1=NC=C(C(=N1)Cl)CI.COC(CC1=CC(=CC(=C1)OC)OC)=O.C(C)(C)NC1CCCCC1.C(CCC)[Li]>>COC(C(CC=1C(=NC(=NC1)Cl)Cl)C1=CC(=CC(=C1)OC)OC)=O | [CH3:1][O:2][C:3](=[O:4])[CH2:5][c:15]1[cH:16][c:17]([O:18][CH3:19])[cH:20][c:21]([O:22][CH3:23])[cH:24]1.I[CH2:6][c:7]1[cH:8][n:9][c:10]([Cl:11])[n:12][c:13]1[Cl:14]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8][n:9][c:10]([Cl:11])[n:12][c:13]1[Cl:14])[c:15]1[cH:16][c:17]([O:18][CH3:19])[cH:20][c:21]([O:22][CH3... | COC(=O)Cc1cc(OC)cc(OC)c1.Clc1ncc(CI)c(Cl)n1 | COC(=O)C(Cc1cnc(Cl)nc1Cl)c1cc(OC)cc(OC)c1 | null | null | C(C)(=O)OCC.O1CCCC1 | C-C Coupling | OtherReaction | cce1a125a1ff1ac49e6bca841c71f39abbf2c962f7edb2747b8c98f3307cb502 | 0061a06af9fc64155952582b91b574e4abd8908ca14244f15179c2400b24dd08 | c1ccc(CCc2cncnc2)cc1 | I-[CH2;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[Cl;D1;H0:8].[C;D1;H3:9]-[#8:10]-[C:11](=[O;D1;H0:12])-[CH2;D2;+0:13]-[c:14](:[c:15]):[c:16]>>[C;D1;H3:9]-[#8:10]-[C:11](=[O;D1;H0:12])-[CH;D3;+0:13](-[CH2;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[Cl;D1;H0:8])-[c:14](:[c:15]):[c:16] | null | [] | -78 | CELSIUS | 30 | MINUTE | To a solution of N-isopropylcyclohexylamine (1.44 g, 10.0 mmol) (Aldrich) in dry tetrahydrofuran (20 mL) was added n-butyllithium (2.5 M in hexanes, 4.0 mL, 10.0 mmol) (Aldrich) at −78° C. under argon. After 30 minutes, a solution of 3,5-dimethoxy-phenyl-acetic acid methyl ester (2.05 g, 9.76 mmol) (from Example 3a sup... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | null | null | c1cncnc1.c1ccccc1 | HI | C(C)(=O)OCC.O1CCCC1 | -78 | 0.5 | COC(=O)Cc1cc(OC)cc(OC)c1.Clc1ncc(CI)c(Cl)n1>C(C)(=O)OCC.O1CCCC1>COC(=O)C(Cc1cnc(Cl)nc1Cl)c1cc(OC)cc(OC)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0190bb8d43134b739d7eeeeba6f57f89 | COC(=O)C(Cc1cnc(Cl)nc1Cl)c1cc(OC)cc(OC)c1.Nc1ccccc1>>COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1cc(OC)cc(OC)c1 | COC(C(CC=1C(=NC(=NC1)Cl)Cl)C1=CC(=CC(=C1)OC)OC)=O.NC1=CC=CC=C1>>COC(C(CC=1C(=NC(=NC1)NC1=CC=CC=C1)NC1=CC=CC=C1)C1=CC(=CC(=C1)OC)OC)=O | Cl[c:10]1[n:9][cH:8][c:7]([CH2:6][CH:5]([C:3]([O:2][CH3:1])=[O:4])[c:27]2[cH:28][c:29]([O:30][CH3:31])[cH:32][c:33]([O:34][CH3:35])[cH:36]2)[c:19](Cl)[n:18]1.[NH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8][n:9][c:10]([NH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:... | COC(=O)C(Cc1cnc(Cl)nc1Cl)c1cc(OC)cc(OC)c1.Nc1ccccc1 | COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1cc(OC)cc(OC)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 41f9322ec5df98feb4edb498f4e5a62751ab580c70737ba501d83b4465521e15 | 23c6396faba21bf6c4e9de50557b8d044c1caf35494930558fc3d2ba563143ac | c1ccc(CCc2cnc(Nc3ccccc3)nc2Nc2ccccc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c;H0;D3;+0:3](-Cl):[c:4](-[C:5]):[c:6]:[#7;a:7]:1.[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C:5]-[c:4]1:[c:6]:[#7;a:7]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]):[#7;a:2]:[c;H0;D3;+0:3]:1-[#7:12]-[c:13] | null | [] | 110 | CELSIUS | null | null | A mixture of 3-(2,4-dichloro-pyrimidin-5-yl)-2-(3,5-dimethoxy-phenyl)-propionic acid methyl ester (186 mg, 0.50 mmol) (from Example 3b supra) and aniline (2.0 mL) (Aldrich) was heated at 110° C. for 2 hours. The reaction mixture was washed with hexanes (50 mL×3) and the supernatant was decanted off after each time. The... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine | Secondary amine.Secondary amine | c1cncnc1 | c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | null | 110 | null | COC(=O)C(Cc1cnc(Cl)nc1Cl)c1cc(OC)cc(OC)c1.Nc1ccccc1>>COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1cc(OC)cc(OC)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-71202caef48949bf8ff4e43739e43746 | COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1cc(OC)cc(OC)c1>>COc1cc(OC)cc(C2Cc3cnc(Nc4ccccc4)nc3N(c3ccccc3)C2=O)c1 | COC(C(CC=1C(=NC(=NC1)NC1=CC=CC=C1)NC1=CC=CC=C1)C1=CC(=CC(=C1)OC)OC)=O.S(O)(O)(=O)=O.C(C)(=O)O>>COC=1C=C(C=C(C1)OC)C1CC2=C(N=C(N=C2)NC2=CC=CC=C2)N(C1=O)C1=CC=CC=C1 | CO[C:32]([CH:10]([c:9]1[cH:8][c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[cH:34]1)[CH2:11][c:12]1[cH:13][n:14][c:15]([NH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[n:23][c:24]1[NH:25][c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1)=[O:33]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[cH:8][c:9]([CH:10]2[CH2:11][c:12]3[... | COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1cc(OC)cc(OC)c1 | COc1cc(OC)cc(C2Cc3cnc(Nc4ccccc4)nc3N(c3ccccc3)C2=O)c1 | null | null | C(C)(=O)OCC | Miscellaneous | OtherReaction | 4c156791040233b925f911d2344eae0f4fe404d66aa7be29ecbd3d34ec58b9ee | 9fb754180ed1affe0187ff01b0205aba264dc674a9ca4b55d9d8c90d1514940e | O=C1C(c2ccccc2)Cc2cnc(Nc3ccccc3)nc2N1c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[c:4])-[C:5]-[c:6]1:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1-[NH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[C:3](-[c:4])-[C:5]-[c:6]2:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:2-[N;H0;D3;+0:12]-1-[c:13](:[c:14]):[c:15] | null | [] | 120 | CELSIUS | null | null | To a solution of 3-(2,4-diphenylamino-pyrimidin-5-yl)-2-(3,5-dimethoxy-phenyl)-propionic acid methyl ester (0.11 mg, 0.23 mmol) (from Example 3c supra) in glacial acetic acid (2 mL) was added concentrated sulfuric acid (0.1 mL) in one portion. The reaction mixture was heated at 120° C. overnight. The reaction mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Tertiary amide | null | c1ncc2c(n1)[NH]CCC2 | c1ccccc1.c1ncc2c(n1)[NH]CCC2.c1ccccc1.c1ccccc1 | HO- | C(C)(=O)OCC | 120 | null | COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1cc(OC)cc(OC)c1>C(C)(=O)OCC>COc1cc(OC)cc(C2Cc3cnc(Nc4ccccc4)nc3N(c3ccccc3)C2=O)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3047c52f326d4823ad745add3224ef15 | COC(=O)Cc1ccccc1.Clc1ncc(CI)c(Cl)n1>>COC(=O)C(Cc1cnc(Cl)nc1Cl)c1ccccc1 | ClC1=NC=C(C(=N1)Cl)CI.COC(CC1=CC=CC=C1)=O.C(C)(C)NC1CCCCC1.C(CCC)[Li]>>COC(C(CC=1C(=NC(=NC1)Cl)Cl)C1=CC=CC=C1)=O | [CH3:1][O:2][C:3](=[O:4])[CH2:5][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1.I[CH2:6][c:7]1[cH:8][n:9][c:10]([Cl:11])[n:12][c:13]1[Cl:14]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8][n:9][c:10]([Cl:11])[n:12][c:13]1[Cl:14])[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | COC(=O)Cc1ccccc1.Clc1ncc(CI)c(Cl)n1 | COC(=O)C(Cc1cnc(Cl)nc1Cl)c1ccccc1 | null | null | C(C)(=O)OCC.O1CCCC1 | C-C Coupling | OtherReaction | cce1a125a1ff1ac49e6bca841c71f39abbf2c962f7edb2747b8c98f3307cb502 | 0061a06af9fc64155952582b91b574e4abd8908ca14244f15179c2400b24dd08 | c1ccc(CCc2cncnc2)cc1 | I-[CH2;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[Cl;D1;H0:8].[C;D1;H3:9]-[#8:10]-[C:11](=[O;D1;H0:12])-[CH2;D2;+0:13]-[c:14](:[c:15]):[c:16]>>[C;D1;H3:9]-[#8:10]-[C:11](=[O;D1;H0:12])-[CH;D3;+0:13](-[CH2;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[Cl;D1;H0:8])-[c:14](:[c:15]):[c:16] | null | [] | -78 | CELSIUS | 30 | MINUTE | To a solution of N-isopropylcyclohexylamine (1.44 g, 10.0 mmol) (Aldrich) in dry tetrahydrofuran (20 mL) was added n-butyllithium (2.5 M in hexanes, 4.0 mL, 10.0 mmol) (Aldrich) at −78° C. under argon. After 30 minutes, a solution of phenylacetic acid methyl ester (1.50 g, 10.0 mmol) (Aldrich) in tetrahydrofuran (5 mL)... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | null | null | c1cncnc1.c1ccccc1 | HI | C(C)(=O)OCC.O1CCCC1 | -78 | 0.5 | COC(=O)Cc1ccccc1.Clc1ncc(CI)c(Cl)n1>C(C)(=O)OCC.O1CCCC1>COC(=O)C(Cc1cnc(Cl)nc1Cl)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-52bce4e4c8a344a39a7507d5991567b3 | COC(=O)C(Cc1cnc(Cl)nc1Cl)c1ccccc1.Nc1ccccc1>>COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1ccccc1 | COC(C(CC=1C(=NC(=NC1)Cl)Cl)C1=CC=CC=C1)=O.NC1=CC=CC=C1>>COC(C(CC=1C(=NC(=NC1)NC1=CC=CC=C1)NC1=CC=CC=C1)C1=CC=CC=C1)=O | Cl[c:10]1[n:9][cH:8][c:7]([CH2:6][CH:5]([C:3]([O:2][CH3:1])=[O:4])[c:27]2[cH:28][cH:29][cH:30][cH:31][cH:32]2)[c:19](Cl)[n:18]1.[NH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8][n:9][c:10]([NH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[n:18][c:19]1[NH:20][c:21... | COC(=O)C(Cc1cnc(Cl)nc1Cl)c1ccccc1.Nc1ccccc1 | COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1ccccc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 41f9322ec5df98feb4edb498f4e5a62751ab580c70737ba501d83b4465521e15 | 23c6396faba21bf6c4e9de50557b8d044c1caf35494930558fc3d2ba563143ac | c1ccc(CCc2cnc(Nc3ccccc3)nc2Nc2ccccc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c;H0;D3;+0:3](-Cl):[c:4](-[C:5]):[c:6]:[#7;a:7]:1.[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C:5]-[c:4]1:[c:6]:[#7;a:7]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]):[#7;a:2]:[c;H0;D3;+0:3]:1-[#7:12]-[c:13] | null | [] | 120 | CELSIUS | null | null | The mixture of 3-(2,4-dichloro-pyrimidin-5-yl)-2-phenyl-propionic acid methyl ester (0.31 g, 1.0 mmol) (from Example 5a supra) and aniline (3.0 mL) (Aldrich) was heated at 120° C. for 1 hour. The reaction mixture was washed with hexanes (50 mL×3) and the supernatant was decanted off after each time. The residue was the... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine | Secondary amine.Secondary amine | c1cncnc1 | c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | null | 120 | null | COC(=O)C(Cc1cnc(Cl)nc1Cl)c1ccccc1.Nc1ccccc1>>COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9da8474bf2d249ce9a1f7b0c9cf31239 | COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1ccccc1>>O=C1C(c2ccccc2)Cc2cnc(Nc3ccccc3)nc2N1c1ccccc1 | COC(C(CC=1C(=NC(=NC1)NC1=CC=CC=C1)NC1=CC=CC=C1)C1=CC=CC=C1)=O.S(O)(O)(=O)=O>>C1(=CC=CC=C1)C1CC2=C(N=C(N=C2)NC2=CC=CC=C2)N(C1=O)C1=CC=CC=C1 | CO[C:2](=[O:1])[CH:3]([c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[CH2:10][c:11]1[cH:12][n:13][c:14]([NH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[n:22][c:23]1[NH:24][c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1>>[O:1]=[C:2]1[CH:3]([c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)[CH2:10][c:11]2[cH:12][n:13][c:14]([NH:15][c:16]3[cH... | COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1ccccc1 | O=C1C(c2ccccc2)Cc2cnc(Nc3ccccc3)nc2N1c1ccccc1 | null | null | C(C)(=O)O.C(C)(=O)OCC | Miscellaneous | OtherReaction | 4c156791040233b925f911d2344eae0f4fe404d66aa7be29ecbd3d34ec58b9ee | 9fb754180ed1affe0187ff01b0205aba264dc674a9ca4b55d9d8c90d1514940e | O=C1C(c2ccccc2)Cc2cnc(Nc3ccccc3)nc2N1c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[c:4])-[C:5]-[c:6]1:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1-[NH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[C:3](-[c:4])-[C:5]-[c:6]2:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:2-[N;H0;D3;+0:12]-1-[c:13](:[c:14]):[c:15] | null | [] | 60 | CELSIUS | null | null | To a solution of 3-(2,4-diphenylamino-pyrimidin-5-yl)-2-phenyl-propionic acid methyl ester (100 mg, 0.24 mmol) (from Example 5b supra) was added 5% concentrated sulfuric acid in glacial acetic acid (3 mL) in one portion. The reaction mixture was heated at 60° C. overnight. After cooling, the reaction mixture was dilute... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Tertiary amide | null | c1ncc2c(n1)[NH]CCC2 | c1ccccc1.c1ncc2c(n1)[NH]CCC2.c1ccccc1.c1ccccc1 | HO- | C(C)(=O)O.C(C)(=O)OCC | 60 | null | COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1ccccc1>C(C)(=O)O.C(C)(=O)OCC>O=C1C(c2ccccc2)Cc2cnc(Nc3ccccc3)nc2N1c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dd5c910e75e942149904f05634a4fdcf | CCOC(=O)Cc1cc(OC)ccc1OC.Clc1ncc(CI)c(Cl)n1>>CCOC(=O)C(Cc1cnc(Cl)nc1Cl)c1cc(OC)ccc1OC | ClC1=NC=C(C(=N1)Cl)CI.C(C)OC(CC1=C(C=CC(=C1)OC)OC)=O.C(C)(C)NC1CCCCC1.C(CCC)[Li]>>C(C)OC(C(CC=1C(=NC(=NC1)Cl)Cl)C1=C(C=CC(=C1)OC)OC)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:16]1[cH:17][c:18]([O:19][CH3:20])[cH:21][cH:22][c:23]1[O:24][CH3:25].I[CH2:7][c:8]1[cH:9][n:10][c:11]([Cl:12])[n:13][c:14]1[Cl:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][n:10][c:11]([Cl:12])[n:13][c:14]1[Cl:15])[c:16]1[cH:17][c:18]([O:19][CH3:20])[cH:21][cH... | CCOC(=O)Cc1cc(OC)ccc1OC.Clc1ncc(CI)c(Cl)n1 | CCOC(=O)C(Cc1cnc(Cl)nc1Cl)c1cc(OC)ccc1OC | null | null | C(C)(=O)OCC.O1CCCC1 | C-C Coupling | OtherReaction | cce1a125a1ff1ac49e6bca841c71f39abbf2c962f7edb2747b8c98f3307cb502 | 0061a06af9fc64155952582b91b574e4abd8908ca14244f15179c2400b24dd08 | c1ccc(CCc2cncnc2)cc1 | I-[CH2;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[Cl;D1;H0:8].[C:9]-[#8:10]-[C:11](=[O;D1;H0:12])-[CH2;D2;+0:13]-[c:14](:[c:15]):[c:16]>>[C:9]-[#8:10]-[C:11](=[O;D1;H0:12])-[CH;D3;+0:13](-[CH2;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[Cl;D1;H0:8])-[c:14](:[c:15]):[c:16] | null | [] | -78 | CELSIUS | 30 | MINUTE | To a solution of N-isopropylcyclohexylamine (1.44 g, 10.0 mmol) (Aldrich) in dry tetrahydrofuran (20 mL) was added n-butyllithium (2.5 M in hexanes, 4.0 mL, 10.0 mmol) (Aldrich) at −78° C. under argon. After 30 minutes, a solution of 2,5-dimethoxyphenylacetic acid ethyl ester (2.24 g, 10.0 mmol) (Aldrich) in tetrahydro... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | null | null | c1cncnc1.c1ccccc1 | HI | C(C)(=O)OCC.O1CCCC1 | -78 | 0.5 | CCOC(=O)Cc1cc(OC)ccc1OC.Clc1ncc(CI)c(Cl)n1>C(C)(=O)OCC.O1CCCC1>CCOC(=O)C(Cc1cnc(Cl)nc1Cl)c1cc(OC)ccc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-19608b27c86f40259bbd4f5626910edb | CCOC(=O)C(Cc1cnc(Cl)nc1Cl)c1cc(OC)ccc1OC>>CCOC(=O)C(C)c1cc(OC)ccc1OC | C(C)OC(C(CC=1C(=NC(=NC1)Cl)Cl)C1=C(C=CC(=C1)OC)OC)=O.NC1=CC=CC=C1>>C(C)OC(C(C)C1=C(C=CC(=C1)OC)OC)=O | Clc1ncc([CH2:7][CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:8]2[cH:9][c:10]([O:11][CH3:12])[cH:13][cH:14][c:15]2[O:16][CH3:17])c(Cl)n1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH3:7])[c:8]1[cH:9][c:10]([O:11][CH3:12])[cH:13][cH:14][c:15]1[O:16][CH3:17] | CCOC(=O)C(Cc1cnc(Cl)nc1Cl)c1cc(OC)ccc1OC | CCOC(=O)C(C)c1cc(OC)ccc1OC | null | null | null | Miscellaneous | OtherReaction | 5eb8f6bdb15093858a6bafe423a23140523d52d5508495a850272db0fe226c02 | 80942023042c2359d6ab4025ad40f6cb742b7cffd380c4ae9895b39a53e111e6 | c1ccccc1 | Cl-c1:n:c:c(-[CH2;D2;+0:1]-[C:2](-[c:3])-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7]):c(-Cl):n:1>>[C:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[C:2](-[CH3;D1;+0:1])-[c:3] | null | [] | 120 | CELSIUS | null | null | The mixture of 3-(2,4-dichloro-pyrimidin-5-yl)-2-(2,5-dimethoxy-phenyl)-propionic acid ethyl ester (0.36 g, 0.94 mmol) (from Example 6a supra) and aniline (2.0 mL) (Aldrich) was heated at 120° C. for 2 hours. The reaction mixture was washed with hexanes (50 mL×3), and the supernatant was decanted off after each time. T... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide | null | c1cncnc1 | null | c1ccccc1 | Other | null | 120 | null | CCOC(=O)C(Cc1cnc(Cl)nc1Cl)c1cc(OC)ccc1OC>>CCOC(=O)C(C)c1cc(OC)ccc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-aa434642a69645fba495e3907de3e968 | COC(=O)Cc1ccccc1OC.Clc1ncc(CI)c(Cl)n1>>COC(=O)C(Cc1cnc(Cl)nc1Cl)c1ccccc1OC | ClC1=NC=C(C(=N1)Cl)CI.COC(CC1=C(C=CC=C1)OC)=O.C(C)(C)NC1CCCCC1.C(CCC)[Li]>>COC(C(CC=1C(=NC(=NC1)Cl)Cl)C1=C(C=CC=C1)OC)=O | [CH3:1][O:2][C:3](=[O:4])[CH2:5][c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]1[O:21][CH3:22].I[CH2:6][c:7]1[cH:8][n:9][c:10]([Cl:11])[n:12][c:13]1[Cl:14]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8][n:9][c:10]([Cl:11])[n:12][c:13]1[Cl:14])[c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]1[O:21][CH3:22] | COC(=O)Cc1ccccc1OC.Clc1ncc(CI)c(Cl)n1 | COC(=O)C(Cc1cnc(Cl)nc1Cl)c1ccccc1OC | null | null | C(C)(=O)OCC.O1CCCC1 | C-C Coupling | OtherReaction | cce1a125a1ff1ac49e6bca841c71f39abbf2c962f7edb2747b8c98f3307cb502 | 0061a06af9fc64155952582b91b574e4abd8908ca14244f15179c2400b24dd08 | c1ccc(CCc2cncnc2)cc1 | I-[CH2;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[Cl;D1;H0:8].[C;D1;H3:9]-[#8:10]-[C:11](=[O;D1;H0:12])-[CH2;D2;+0:13]-[c:14](:[c:15]):[c:16]>>[C;D1;H3:9]-[#8:10]-[C:11](=[O;D1;H0:12])-[CH;D3;+0:13](-[CH2;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[Cl;D1;H0:8])-[c:14](:[c:15]):[c:16] | null | [] | -78 | CELSIUS | 30 | MINUTE | To a solution of N-isopropylcyclohexylamine (1.44 g, 10.0 mmol) (Aldrich) in dry tetrahydrofuran (20 mL) was added n-butyllithium (2.5 M in hexanes, 4.0 mL, 10.0 mmol) (Aldrich) at −78° C. under argon. After 30 minutes, a solution of 2-methoxyphenylacetic acid methyl ester (1.8 g, 10.0 mmol) (TCI-US) in tetrahydrofuran... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | null | null | c1cncnc1.c1ccccc1 | HI | C(C)(=O)OCC.O1CCCC1 | -78 | 0.5 | COC(=O)Cc1ccccc1OC.Clc1ncc(CI)c(Cl)n1>C(C)(=O)OCC.O1CCCC1>COC(=O)C(Cc1cnc(Cl)nc1Cl)c1ccccc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-03f9a95783854b8395a684e5c8db3095 | COC(=O)C(Cc1cnc(Cl)nc1Cl)c1ccccc1OC.Nc1ccccc1>>COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1ccccc1OC | COC(C(CC=1C(=NC(=NC1)Cl)Cl)C1=C(C=CC=C1)OC)=O.NC1=CC=CC=C1>>COC(C(CC=1C(=NC(=NC1)NC1=CC=CC=C1)NC1=CC=CC=C1)C1=C(C=CC=C1)OC)=O | Cl[c:10]1[n:9][cH:8][c:7]([CH2:6][CH:5]([C:3]([O:2][CH3:1])=[O:4])[c:27]2[cH:28][cH:29][cH:30][cH:31][c:32]2[O:33][CH3:34])[c:19](Cl)[n:18]1.[NH2:11][c:12]1[cH:13][cH:14][cH:24][cH:25][cH:26]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8][n:9][c:10]([NH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[n:18][c:19]... | COC(=O)C(Cc1cnc(Cl)nc1Cl)c1ccccc1OC.Nc1ccccc1 | COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1ccccc1OC | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 17063f9790599d9363915ef3b96d7a5711afaaf38fdeacf6e3cc163a0b39b4e5 | 23c6396faba21bf6c4e9de50557b8d044c1caf35494930558fc3d2ba563143ac | c1ccc(CCc2cnc(Nc3ccccc3)nc2Nc2ccccc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c;H0;D3;+0:3](-Cl):[c:4](-[C:5]):[c:6]:[#7;a:7]:1.[NH2;D1;+0:8]-[c;H0;D3;+0:9]1:[c:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[c:13]:[cH;D2;+0:14]:1>>[C:5]-[c:4]1:[c:6]:[#7;a:7]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[c;H0;D3;+0:9]2:[c:10]:[cH;D2;+0:11]:[c:15]:[c:16]:[c:17]:2):[#7;a:2]:[c;H0;D3;+0:3]:1-[#7:18]-... | null | [] | 120 | CELSIUS | null | null | A mixture of 3-(2,4-dichloro-pyrimidin-5-yl)-2-(2-methoxy-phenyl)-propionic acid methyl ester (0.34 g, 1.0 mmol) (from Example 7a supra) and aniline (2.0 mL) (Aldrich) was heated at 120° C. for 1 hour. The reaction mixture was washed with hexanes (50 mL×3) and the supernatant was decanted off after each time. The resid... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine | Secondary amine.Secondary amine | c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1.c1ccccc1 | c1cncnc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | null | 120 | null | COC(=O)C(Cc1cnc(Cl)nc1Cl)c1ccccc1OC.Nc1ccccc1>>COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1ccccc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8312e661429447d69f797ea2a7092eb8 | COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1ccccc1OC>>COc1ccccc1C1Cc2cnc(Nc3ccccc3)nc2N(c2ccccc2)C1=O | COC(C(CC=1C(=NC(=NC1)NC1=CC=CC=C1)NC1=CC=CC=C1)C1=C(C=CC=C1)OC)=O.S(O)(O)(=O)=O>>COC1=C(C=CC=C1)C1CC2=C(N=C(N=C2)NC2=CC=CC=C2)N(C1=O)C1=CC=CC=C1 | CO[C:31]([CH:9]([c:8]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]1)[CH2:10][c:11]1[cH:12][n:13][c:14]([NH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[n:22][c:23]1[NH:24][c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1)=[O:32]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH:9]1[CH2:10][c:11]2[cH:12][n:13][c:14]([NH:... | COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1ccccc1OC | COc1ccccc1C1Cc2cnc(Nc3ccccc3)nc2N(c2ccccc2)C1=O | null | null | C(C)(=O)O.C(C)(=O)OCC | Miscellaneous | OtherReaction | 4c156791040233b925f911d2344eae0f4fe404d66aa7be29ecbd3d34ec58b9ee | 9fb754180ed1affe0187ff01b0205aba264dc674a9ca4b55d9d8c90d1514940e | O=C1C(c2ccccc2)Cc2cnc(Nc3ccccc3)nc2N1c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[c:4])-[C:5]-[c:6]1:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1-[NH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[C:3](-[c:4])-[C:5]-[c:6]2:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:2-[N;H0;D3;+0:12]-1-[c:13](:[c:14]):[c:15] | null | [] | 110 | CELSIUS | null | null | To a solution of 3-(2,4-diphenylamino-pyrimidin-5-yl)-2-(2-dimethoxy-phenyl propionic acid methyl ester (181.8 mg, 0.40 mmol) (from Example 7b supra) was added 5% concentrated sulfuric acid in glacial acetic acid (3 mL) in one portion. The reaction mixture was heated at 110° C. for 3 hours. After cooling, the reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Tertiary amide | null | c1ncc2c(n1)[NH]CCC2 | c1ccccc1.c1ncc2c(n1)[NH]CCC2.c1ccccc1.c1ccccc1 | HO- | C(C)(=O)O.C(C)(=O)OCC | 110 | null | COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1ccccc1OC>C(C)(=O)O.C(C)(=O)OCC>COc1ccccc1C1Cc2cnc(Nc3ccccc3)nc2N(c2ccccc2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-410bce6426de4dcc9092dfffbf90a523 | CO.O=C(O)Cc1cc(C(F)(F)F)cc(C(F)(F)F)c1>>COC(=O)Cc1cc(C(F)(F)F)cc(C(F)(F)F)c1 | FC(C=1C=C(C=C(C1)C(F)(F)F)CC(=O)O)(F)F.S(O)(O)(=O)=O.CO>>COC(CC1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)=O | [CH3:1][OH:2].O[C:3](=[O:4])[CH2:5][c:6]1[cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19]1 | CO.O=C(O)Cc1cc(C(F)(F)F)cc(C(F)(F)F)c1 | COC(=O)Cc1cc(C(F)(F)F)cc(C(F)(F)F)c1 | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[C;D1;H3:5]-[OH;D1;+0:6]>>[C;D1;H3:5]-[O;H0;D2;+0:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4] | null | [] | null | null | null | null | To a solution of 3,5-bis-trifluoromethylphenylacetic acid (3.0 g, 11.03 mmol) (Aldrich) in methanol (20 mL) was added concentrated sulfuric acid (1.0 mL) and the reaction mixture was heated at reflux overnight. The reaction mixture was concentrated in vacuo. The residue was then diluted with ethyl acetate (100 mL) and ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1 | HO- | null | null | null | CO.O=C(O)Cc1cc(C(F)(F)F)cc(C(F)(F)F)c1>>COC(=O)Cc1cc(C(F)(F)F)cc(C(F)(F)F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f440d966f1894a53b2308e1677ea1004 | COC(=O)Cc1cc(C(F)(F)F)cc(C(F)(F)F)c1.Clc1ncc(CI)c(Cl)n1>>COC(=O)C(Cc1cnc(Cl)nc1Cl)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 | ClC1=NC=C(C(=N1)Cl)CI.COC(CC1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)=O.C(C)(C)NC1CCCCC1.C(CCC)[Li]>>COC(C(CC=1C(=NC(=NC1)Cl)Cl)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)=O | [CH3:1][O:2][C:3](=[O:4])[CH2:5][c:15]1[cH:16][c:17]([C:18]([F:19])([F:20])[F:21])[cH:22][c:23]([C:24]([F:25])([F:26])[F:27])[cH:28]1.I[CH2:6][c:7]1[cH:8][n:9][c:10]([Cl:11])[n:12][c:13]1[Cl:14]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8][n:9][c:10]([Cl:11])[n:12][c:13]1[Cl:14])[c:15]1[cH:16][c:17]([C:18]([F:1... | COC(=O)Cc1cc(C(F)(F)F)cc(C(F)(F)F)c1.Clc1ncc(CI)c(Cl)n1 | COC(=O)C(Cc1cnc(Cl)nc1Cl)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 | null | null | C(C)(=O)OCC.O1CCCC1 | C-C Coupling | OtherReaction | cce1a125a1ff1ac49e6bca841c71f39abbf2c962f7edb2747b8c98f3307cb502 | 0061a06af9fc64155952582b91b574e4abd8908ca14244f15179c2400b24dd08 | c1ccc(CCc2cncnc2)cc1 | I-[CH2;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[Cl;D1;H0:8].[C;D1;H3:9]-[#8:10]-[C:11](=[O;D1;H0:12])-[CH2;D2;+0:13]-[c:14](:[c:15]):[c:16]>>[C;D1;H3:9]-[#8:10]-[C:11](=[O;D1;H0:12])-[CH;D3;+0:13](-[CH2;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[Cl;D1;H0:8])-[c:14](:[c:15]):[c:16] | null | [] | -78 | CELSIUS | 10 | MINUTE | To a solution of N-isopropylcyclohexylamine (1.44 g, 10.0 mmol) (Aldrich) in dry tetrahydrofuran (20 mL) was added n-butyllithium (2.5 M in hexanes, 4.0 mL, 10.0 mmol) (Aldrich) at −78° C. under argon. After 10 minutes, a solution of 3,5-bis-trifluoromethylphenylacetic acid methyl ester (2.20 g, 7.7 mmol) (from Example... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | null | null | c1cncnc1.c1ccccc1 | HI | C(C)(=O)OCC.O1CCCC1 | -78 | 0.166667 | COC(=O)Cc1cc(C(F)(F)F)cc(C(F)(F)F)c1.Clc1ncc(CI)c(Cl)n1>C(C)(=O)OCC.O1CCCC1>COC(=O)C(Cc1cnc(Cl)nc1Cl)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1bfc78b0e9c34df2912beabf6aeef46e | COC(=O)C(Cc1cnc(Cl)nc1Cl)c1cc(C(F)(F)F)cc(C(F)(F)F)c1.Nc1ccccc1>>COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 | COC(C(CC=1C(=NC(=NC1)Cl)Cl)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)=O.NC1=CC=CC=C1>>COC(C(CC=1C(=NC(=NC1)NC1=CC=CC=C1)NC1=CC=CC=C1)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)=O | Cl[c:10]1[n:9][cH:8][c:7]([CH2:6][CH:5]([C:3]([O:2][CH3:1])=[O:4])[c:27]2[cH:28][c:29]([C:30]([F:31])([F:32])[F:33])[cH:34][c:35]([C:21]([F:37])([F:38])[F:39])[cH:40]2)[c:19](Cl)[n:18]1.[NH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8][n:9][c:10]([NH:11][c:12]2[cH:... | COC(=O)C(Cc1cnc(Cl)nc1Cl)c1cc(C(F)(F)F)cc(C(F)(F)F)c1.Nc1ccccc1 | COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | b4dee609a389ff7f843d73232772b98d4a12787647b142169d0155e38d213758 | 9ea777f6eec6d1dd352e8ec268b374f330238735f05383c104bdeece6906e400 | c1ccc(CCc2cnc(Nc3ccccc3)nc2Nc2ccccc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c;H0;D3;+0:3](-Cl):[c:4](-[C:5]):[c:6]:[#7;a:7]:1.[F;H0;D1;+0:8]-[C;H0;D4;+0:9](-[F;H0;D1;+0:10])(-[F;H0;D1;+0:11])-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16].[NH2;D1;+0:17]-[c:18](:[c:19]):[c:20]>>[C:5]-[c:4]1:[c:6]:[#7;a:7]:[c;H0;D3;+0:1](-[NH;D2;+0:17]-[c:18](:[c:19]):[c:20]):[#7;a:2]... | null | [] | 120 | CELSIUS | null | null | A mixture of 2-(3,5-bis-trifluoromethyl-phenyl)-3-(2,4-dichloro-pyrimidin-5-yl)-propionic acid methyl ester (0.35 g, 0.78 mmol) (from Example 8b supra) and aniline (2.0 mL) (Aldrich) was heated at 120° C. for 1 hour. The reaction mixture was washed with hexanes (50 mL×3) and the supernatant was decanted off after each ... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Aromatic halide.Aromatic halide.Primary amine | Trifluoro group.Secondary amine.Secondary amine | c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1.c1ccccc1 | c1cncnc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | null | 120 | null | COC(=O)C(Cc1cnc(Cl)nc1Cl)c1cc(C(F)(F)F)cc(C(F)(F)F)c1.Nc1ccccc1>>COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fd307c631251414fb63b7d58f5f8cce4 | COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1cc(C(F)(F)F)cc(C(F)(F)F)c1>>O=C1C(c2cc(C(F)(F)F)cc(C(F)(F)F)c2)Cc2cnc(Nc3ccccc3)nc2N1c1ccccc1 | COC(C(CC=1C(=NC(=NC1)NC1=CC=CC=C1)NC1=CC=CC=C1)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)=O.S(O)(O)(=O)=O>>FC(C=1C=C(C=C(C1)C(F)(F)F)C1CC2=C(N=C(N=C2)NC2=CC=CC=C2)N(C1=O)C1=CC=CC=C1)(F)F | CO[C:2](=[O:1])[CH:3]([c:4]1[cH:5][c:6]([C:7]([F:8])([F:9])[F:10])[cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17]1)[CH2:18][c:19]1[cH:20][n:21][c:22]([NH:23][c:24]2[cH:25][cH:26][cH:27][cH:28][cH:29]2)[n:30][c:31]1[NH:32][c:33]1[cH:34][cH:35][cH:36][cH:37][cH:38]1>>[O:1]=[C:2]1[CH:3]([c:4]2[cH:5][c:6]([C:7]([F:8])([... | COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 | O=C1C(c2cc(C(F)(F)F)cc(C(F)(F)F)c2)Cc2cnc(Nc3ccccc3)nc2N1c1ccccc1 | null | null | C(C)(=O)O.C(C)(=O)OCC | Miscellaneous | OtherReaction | 4c156791040233b925f911d2344eae0f4fe404d66aa7be29ecbd3d34ec58b9ee | 9fb754180ed1affe0187ff01b0205aba264dc674a9ca4b55d9d8c90d1514940e | O=C1C(c2ccccc2)Cc2cnc(Nc3ccccc3)nc2N1c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[c:4])-[C:5]-[c:6]1:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1-[NH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[C:3](-[c:4])-[C:5]-[c:6]2:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:2-[N;H0;D3;+0:12]-1-[c:13](:[c:14]):[c:15] | null | [] | 120 | CELSIUS | null | null | To a solution of 3-(2,4-diphenylamino-pyrimidin-5-yl)-2-(3,5-bis-trifluoromethyl-phenyl)-propionic acid methyl ester (0.20 g, 0.36 mmol) (from Example 8c supra) was added 5% concentrated sulfuric acid in glacial acetic acid (3 mL) in one portion. The reaction mixture was heated at 120° C. for 3 hours. The reaction mixt... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Tertiary amide | null | c1ncc2c(n1)[NH]CCC2 | c1ccccc1.c1ncc2c(n1)[NH]CCC2.c1ccccc1.c1ccccc1 | HO- | C(C)(=O)O.C(C)(=O)OCC | 120 | null | COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1cc(C(F)(F)F)cc(C(F)(F)F)c1>C(C)(=O)O.C(C)(=O)OCC>O=C1C(c2cc(C(F)(F)F)cc(C(F)(F)F)c2)Cc2cnc(Nc3ccccc3)nc2N1c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-014700ab78b24173b0516adc76ae8891 | CCOC(=O)Cc1ccncc1.Clc1ncc(CI)c(Cl)n1>>CCOC(=O)C(Cc1cnc(Cl)nc1Cl)c1ccncc1 | ClC1=NC=C(C(=N1)Cl)CI.C(C)OC(CC1=CC=NC=C1)=O.C(C)(C)NC1CCCCC1.C(CCC)[Li]>>C(C)OC(C(CC=1C(=NC(=NC1)Cl)Cl)C1=CC=NC=C1)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:16]1[cH:17][cH:18][n:19][cH:20][cH:21]1.I[CH2:7][c:8]1[cH:9][n:10][c:11]([Cl:12])[n:13][c:14]1[Cl:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][n:10][c:11]([Cl:12])[n:13][c:14]1[Cl:15])[c:16]1[cH:17][cH:18][n:19][cH:20][cH:21]1 | CCOC(=O)Cc1ccncc1.Clc1ncc(CI)c(Cl)n1 | CCOC(=O)C(Cc1cnc(Cl)nc1Cl)c1ccncc1 | null | null | C(C)(=O)OCC.O1CCCC1 | C-C Coupling | OtherReaction | cce1a125a1ff1ac49e6bca841c71f39abbf2c962f7edb2747b8c98f3307cb502 | 0061a06af9fc64155952582b91b574e4abd8908ca14244f15179c2400b24dd08 | c1cc(CCc2cncnc2)ccn1 | I-[CH2;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[Cl;D1;H0:8].[C:9]-[#8:10]-[C:11](=[O;D1;H0:12])-[CH2;D2;+0:13]-[c:14]1:[c:15]:[c:16]:[#7;a:17]:[c:18]:[c:19]:1>>[C:9]-[#8:10]-[C:11](=[O;D1;H0:12])-[CH;D3;+0:13](-[CH2;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[Cl;D1;H0:8])-[c:14]1:[c:15]:[c:16]:... | null | [] | -78 | CELSIUS | 30 | MINUTE | To a solution of N-isopropylcyclohexylamine (720 mg, 5.0 mmol) (Aldrich) in dry tetrahydrofuran (10 mL) was added n-butyllithium (2.5 M in hexanes, 2.0 mL, 5.0 mmol) (Aldrich) at −78° C. under argon. After 30 minutes, a solution of 4-pyridylacetic acid ethyl ester (826 mg, 5.0 mmol) (Lancaster) in tetrahydrofuran (3 mL... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | null | null | c1cncnc1.c1ccncc1 | HI | C(C)(=O)OCC.O1CCCC1 | -78 | 0.5 | CCOC(=O)Cc1ccncc1.Clc1ncc(CI)c(Cl)n1>C(C)(=O)OCC.O1CCCC1>CCOC(=O)C(Cc1cnc(Cl)nc1Cl)c1ccncc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c8b46ff25274422d8d420363821a71ce | CCOC(=O)C(Cc1cnc(Cl)nc1Cl)c1ccncc1.Nc1ccccc1>>CCOC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1ccncc1 | C(C)OC(C(CC=1C(=NC(=NC1)Cl)Cl)C1=CC=NC=C1)=O.NC1=CC=CC=C1>>C(C)OC(C(CC=1C(=NC(=NC1)NC1=CC=CC=C1)NC1=CC=CC=C1)C1=CC=NC=C1)=O | Cl[c:11]1[n:10][cH:9][c:8]([CH2:7][CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:28]2[cH:29][cH:30][n:31][cH:32][cH:33]2)[c:20](Cl)[n:19]1.[NH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][n:10][c:11]([NH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[n:19][c:2... | CCOC(=O)C(Cc1cnc(Cl)nc1Cl)c1ccncc1.Nc1ccccc1 | CCOC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1ccncc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 41f9322ec5df98feb4edb498f4e5a62751ab580c70737ba501d83b4465521e15 | 23c6396faba21bf6c4e9de50557b8d044c1caf35494930558fc3d2ba563143ac | c1ccc(Nc2ncc(CCc3ccncc3)c(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4](-[C:5]):[c;H0;D3;+0:6](-Cl):[#7;a:7]:1.[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C:5]-[c:4]1:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]):[#7;a:7]:[c;H0;D3;+0:6]:1-[#7:12]-[c:13] | null | [] | 120 | CELSIUS | null | null | A mixture of 3-(2,4-dichloro-pyrimidin-5-yl)-2-pyridin-4-yl-propionic acid ethyl ester (0.68 g, 2.0 mmol) (from Example 9a supra) and aniline (3.0 mL) (Aldrich) was heated at 120° C. for 2 hours. The reaction mixture was washed with hexanes (50 mL×3) and the supernatant was decanted off after each time. The residue was... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine | Secondary amine.Secondary amine | c1cncnc1 | c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1.c1ccccc1.c1ccncc1 | null | null | 120 | null | CCOC(=O)C(Cc1cnc(Cl)nc1Cl)c1ccncc1.Nc1ccccc1>>CCOC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1ccncc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-49cc03df8cc74ace9a5489774bcf36d0 | CCOC(=O)Cc1cccnc1.Clc1ncc(CI)c(Cl)n1>>CCOC(=O)C(Cc1cnc(Cl)nc1Cl)c1cccnc1 | ClC1=NC=C(C(=N1)Cl)CI.C(C)OC(CC=1C=NC=CC1)=O.C(C)(C)NC1CCCCC1.C(CCC)[Li]>>C(C)OC(C(CC=1C(=NC(=NC1)Cl)Cl)C=1C=NC=CC1)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:16]1[cH:17][cH:18][cH:19][n:20][cH:21]1.I[CH2:7][c:8]1[cH:9][n:10][c:11]([Cl:12])[n:13][c:14]1[Cl:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][n:10][c:11]([Cl:12])[n:13][c:14]1[Cl:15])[c:16]1[cH:17][cH:18][cH:19][n:20][cH:21]1 | CCOC(=O)Cc1cccnc1.Clc1ncc(CI)c(Cl)n1 | CCOC(=O)C(Cc1cnc(Cl)nc1Cl)c1cccnc1 | null | null | C(C)(=O)OCC.O1CCCC1 | C-C Coupling | OtherReaction | cce1a125a1ff1ac49e6bca841c71f39abbf2c962f7edb2747b8c98f3307cb502 | 0061a06af9fc64155952582b91b574e4abd8908ca14244f15179c2400b24dd08 | c1cncc(CCc2cncnc2)c1 | I-[CH2;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[Cl;D1;H0:8].[C:9]-[#8:10]-[C:11](=[O;D1;H0:12])-[CH2;D2;+0:13]-[c:14](:[c:15]):[c:16]:[#7;a:17]:[c:18]>>[C:9]-[#8:10]-[C:11](=[O;D1;H0:12])-[CH;D3;+0:13](-[CH2;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[Cl;D1;H0:8])-[c:14](:[c:15]):[c:16]:[#7;a:1... | null | [] | -78 | CELSIUS | 10 | MINUTE | To a solution of N-isopropylcyclohexylamine (1.44 g, 10.0 mmol) (Aldrich) in dry tetrahydrofuran (20 mL) was added n-butyllithium (2.5 M in hexanes, 4.0 mL, 10.0 mmol) (Aldrich) at −78° C. under argon. After 10 minutes, a solution of 2-pyridin-3-yl-acetic acid ethyl ester (1.65 g, 10.0 mmol) (Acros) in tetrahydrofuran ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | null | null | c1cncnc1.c1ccncc1 | HI | C(C)(=O)OCC.O1CCCC1 | -78 | 0.166667 | CCOC(=O)Cc1cccnc1.Clc1ncc(CI)c(Cl)n1>C(C)(=O)OCC.O1CCCC1>CCOC(=O)C(Cc1cnc(Cl)nc1Cl)c1cccnc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-574db29389fe441fb2573534e99b8d0c | CCOC(=O)C(Cc1cnc(Cl)nc1Cl)c1cccnc1.Nc1ccccc1>>CCOC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1cccnc1 | C(C)OC(C(CC=1C(=NC(=NC1)Cl)Cl)C=1C=NC=CC1)=O.NC1=CC=CC=C1>>C(C)OC(C(CC=1C(=NC(=NC1)NC1=CC=CC=C1)NC1=CC=CC=C1)C=1C=NC=CC1)=O | Cl[c:11]1[n:10][cH:9][c:8]([CH2:7][CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:28]2[cH:29][cH:30][cH:31][n:32][cH:33]2)[c:20](Cl)[n:19]1.[NH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][n:10][c:11]([NH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[n:19][c:2... | CCOC(=O)C(Cc1cnc(Cl)nc1Cl)c1cccnc1.Nc1ccccc1 | CCOC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1cccnc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 41f9322ec5df98feb4edb498f4e5a62751ab580c70737ba501d83b4465521e15 | 23c6396faba21bf6c4e9de50557b8d044c1caf35494930558fc3d2ba563143ac | c1ccc(Nc2ncc(CCc3cccnc3)c(Nc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4](-[C:5]):[c;H0;D3;+0:6](-Cl):[#7;a:7]:1.[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C:5]-[c:4]1:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]):[#7;a:7]:[c;H0;D3;+0:6]:1-[#7:12]-[c:13] | null | [] | 120 | CELSIUS | null | null | A mixture of 3-(2,4-dichloro-pyrimidin-5-yl)-2-pyridin-3-yl-propionic acid ethyl ester (326 mg, 1.0 mmol) (from Example 10a supra) and aniline (2.0 mL) (Aldrich) was heated at 120° C. for 1 hour. The reaction mixture was washed with hexanes (50 mL×3) and the supernatant was decanted off after each time. The residue was... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine | Secondary amine.Secondary amine | c1cncnc1 | c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1.c1ccccc1.c1ccncc1 | null | null | 120 | null | CCOC(=O)C(Cc1cnc(Cl)nc1Cl)c1cccnc1.Nc1ccccc1>>CCOC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1cccnc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-710b344f3c0a4faa858fdd396076bad7 | CCOC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1cccnc1>>O=C1C(c2cccnc2)Cc2cnc(Nc3ccccc3)nc2N1c1ccccc1 | C(C)OC(C(CC=1C(=NC(=NC1)NC1=CC=CC=C1)NC1=CC=CC=C1)C=1C=NC=CC1)=O.S(O)(O)(=O)=O>>C1(=CC=CC=C1)N1C(C(CC2=C1N=C(N=C2)NC2=CC=CC=C2)C=2C=NC=CC2)=O | CCO[C:2](=[O:1])[CH:3]([c:4]1[cH:5][cH:6][cH:7][n:8][cH:9]1)[CH2:10][c:11]1[cH:12][n:13][c:14]([NH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[n:22][c:23]1[NH:24][c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1>>[O:1]=[C:2]1[CH:3]([c:4]2[cH:5][cH:6][cH:7][n:8][cH:9]2)[CH2:10][c:11]2[cH:12][n:13][c:14]([NH:15][c:16]3[cH:... | CCOC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1cccnc1 | O=C1C(c2cccnc2)Cc2cnc(Nc3ccccc3)nc2N1c1ccccc1 | null | null | C(C)(=O)O.C(C)(=O)OCC | Miscellaneous | OtherReaction | 4c156791040233b925f911d2344eae0f4fe404d66aa7be29ecbd3d34ec58b9ee | 9fb754180ed1affe0187ff01b0205aba264dc674a9ca4b55d9d8c90d1514940e | O=C1C(c2cccnc2)Cc2cnc(Nc3ccccc3)nc2N1c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4]-[c:5]1:[c:6]:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:1-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14])-[c:15]:[c:16]:[#7;a:17]>>[#7;a:17]:[c:16]:[c:15]-[C:3]1-[C:4]-[c:5]2:[c:6]:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:2-[N;H0;D3;+0:11](-[c:12](:[c:13]):[c:14])-[C;H0;D3;+0:1]-1=[O;D1;H0:2] | null | [] | 120 | CELSIUS | null | null | To a solution of 3-(2,4-diphenylamino-pyrimidin-5-yl)-2-pyridin-3-yl-propionic acid ethyl ester (60 mg, 0.36 mmol) (from Example 10b supra) was added 5% concentrated sulfuric acid in glacial acetic acid (3 mL) in one portion. The reaction mixture was heated at 120° C. for 3 hours. The reaction mixture was then diluted ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Tertiary amide | null | c1ncc2c(n1)[NH]CCC2 | c1ccncc1.c1ncc2c(n1)[NH]CCC2.c1ccccc1.c1ccccc1 | HO- | C(C)(=O)O.C(C)(=O)OCC | 120 | null | CCOC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1cccnc1>C(C)(=O)O.C(C)(=O)OCC>O=C1C(c2cccnc2)Cc2cnc(Nc3ccccc3)nc2N1c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6595dcbcaa4e4ea4ba99ea2f8bf33099 | CCOC(=O)Cc1ccc(OC)c(OC)c1.Clc1ncc(CI)c(Cl)n1>>CCOC(=O)C(Cc1cnc(Cl)nc1Cl)c1ccc(OC)c(OC)c1 | ClC1=NC=C(C(=N1)Cl)CI.C(C)OC(CC1=CC(=C(C=C1)OC)OC)=O.C(C)(C)NC1CCCCC1.C(CCC)[Li]>>C(C)OC(C(CC=1C(=NC(=NC1)Cl)Cl)C1=CC(=C(C=C1)OC)OC)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:16]1[cH:17][cH:18][c:19]([O:20][CH3:21])[c:22]([O:23][CH3:24])[cH:25]1.I[CH2:7][c:8]1[cH:9][n:10][c:11]([Cl:12])[n:13][c:14]1[Cl:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][n:10][c:11]([Cl:12])[n:13][c:14]1[Cl:15])[c:16]1[cH:17][cH:18][c:19]([O:20][CH3:21])[... | CCOC(=O)Cc1ccc(OC)c(OC)c1.Clc1ncc(CI)c(Cl)n1 | CCOC(=O)C(Cc1cnc(Cl)nc1Cl)c1ccc(OC)c(OC)c1 | null | null | C(C)(=O)OCC.O1CCCC1 | C-C Coupling | OtherReaction | cce1a125a1ff1ac49e6bca841c71f39abbf2c962f7edb2747b8c98f3307cb502 | 0061a06af9fc64155952582b91b574e4abd8908ca14244f15179c2400b24dd08 | c1ccc(CCc2cncnc2)cc1 | I-[CH2;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[Cl;D1;H0:8].[C:9]-[#8:10]-[C:11](=[O;D1;H0:12])-[CH2;D2;+0:13]-[c:14](:[c:15]):[c:16]>>[C:9]-[#8:10]-[C:11](=[O;D1;H0:12])-[CH;D3;+0:13](-[CH2;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[Cl;D1;H0:8])-[c:14](:[c:15]):[c:16] | null | [] | -78 | CELSIUS | 30 | MINUTE | To a solution of N-isopropylcyclohexylamine (720 mg, 5.0 mmol) (Aldrich) in dry tetrahydrofuran (10 mL) was added n-butyllithium (2.5 M in hexanes, 2.0 mL, 5.0 mmol) (Aldrich) at −78° C. under argon. After 30 minutes, a solution of 3,4-dimethoxyphenylacetic acid ethyl ester (1.12 g, 5.0 mmol) (Lancaster) in tetrahydrof... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | null | null | c1cncnc1.c1ccccc1 | HI | C(C)(=O)OCC.O1CCCC1 | -78 | 0.5 | CCOC(=O)Cc1ccc(OC)c(OC)c1.Clc1ncc(CI)c(Cl)n1>C(C)(=O)OCC.O1CCCC1>CCOC(=O)C(Cc1cnc(Cl)nc1Cl)c1ccc(OC)c(OC)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7e15299e24944a1ea8f3d98132393c75 | CCOC(=O)C(Cc1cnc(Cl)nc1Cl)c1ccc(OC)c(OC)c1.Nc1ccccc1>>CCOC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1ccc(OC)c(OC)c1 | C(C)OC(C(CC=1C(=NC(=NC1)Cl)Cl)C1=CC(=C(C=C1)OC)OC)=O.NC1=CC=CC=C1>>C(C)OC(C(CC=1C(=NC(=NC1)NC1=CC=CC=C1)NC1=CC=CC=C1)C1=CC(=C(C=C1)OC)OC)=O | Cl[c:11]1[n:10][cH:9][c:8]([CH2:7][CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:28]2[cH:29][cH:30][c:31]([O:32][CH3:33])[c:34]([O:35][CH3:36])[cH:37]2)[c:20](Cl)[n:19]1.[NH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][n:10][c:11]([NH:12][c:13]2[cH:14][cH:15][c... | CCOC(=O)C(Cc1cnc(Cl)nc1Cl)c1ccc(OC)c(OC)c1.Nc1ccccc1 | CCOC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1ccc(OC)c(OC)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 41f9322ec5df98feb4edb498f4e5a62751ab580c70737ba501d83b4465521e15 | 23c6396faba21bf6c4e9de50557b8d044c1caf35494930558fc3d2ba563143ac | c1ccc(CCc2cnc(Nc3ccccc3)nc2Nc2ccccc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4](-[C:5]):[c;H0;D3;+0:6](-Cl):[#7;a:7]:1.[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C:5]-[c:4]1:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]):[#7;a:7]:[c;H0;D3;+0:6]:1-[#7:12]-[c:13] | null | [] | 110 | CELSIUS | null | null | A mixture of 3-(2,4-dichloro-pyrimidin-5-yl)-2-(3,4-dimethoxy-phenyl)-propionic acid ethyl ester (440 mg, 1.1 mmol) (from Example 11a supra) and aniline (2.0 mL) (Aldrich) was heated at 110° C. for 2 hours. The reaction mixture was washed with hexanes (50 mL×3) and the supernatant was decanted off after each time. The ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine | Secondary amine.Secondary amine | c1cncnc1 | c1cncnc1.c1ccccc1 | c1cncnc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | null | 110 | null | CCOC(=O)C(Cc1cnc(Cl)nc1Cl)c1ccc(OC)c(OC)c1.Nc1ccccc1>>CCOC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1ccc(OC)c(OC)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f879e793117f44abb15e98d9218b229e | CCOC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1ccc(OC)c(OC)c1>>COc1ccc(C2Cc3cnc(Nc4ccccc4)nc3N(c3ccccc3)C2=O)cc1OC | C(C)OC(C(CC=1C(=NC(=NC1)NC1=CC=CC=C1)NC1=CC=CC=C1)C1=CC(=C(C=C1)OC)OC)=O.S(O)(O)(=O)=O.C(C)(=O)O>>COC=1C=C(C=CC1OC)C1CC2=C(N=C(N=C2)NC2=CC=CC=C2)N(C1=O)C1=CC=CC=C1 | CCO[C:29]([CH:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:32]([O:33][CH3:34])[cH:31]1)[CH2:8][c:9]1[cH:10][n:11][c:12]([NH:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[n:20][c:21]1[NH:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1)=[O:30]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]2[CH2:8][c:9]3[cH:10][n:11][c:12]([N... | CCOC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1ccc(OC)c(OC)c1 | COc1ccc(C2Cc3cnc(Nc4ccccc4)nc3N(c3ccccc3)C2=O)cc1OC | null | null | C(C)(=O)OCC | Miscellaneous | OtherReaction | 4c156791040233b925f911d2344eae0f4fe404d66aa7be29ecbd3d34ec58b9ee | 9fb754180ed1affe0187ff01b0205aba264dc674a9ca4b55d9d8c90d1514940e | O=C1C(c2ccccc2)Cc2cnc(Nc3ccccc3)nc2N1c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[c:4])-[C:5]-[c:6]1:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1-[NH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[C:3](-[c:4])-[C:5]-[c:6]2:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:2-[N;H0;D3;+0:12]-1-[c:13](:[c:14]):[c:15] | null | [] | 80 | CELSIUS | null | null | To a solution of 3-(2,4-diphenylamino-pyrimidin-5-yl)-2-(3,4-dimethoxy-phenyl)-propionic acid ethyl ester (470 mg, 0.94 mmol) (from Example 11b supra) in glacial acetic acid (3 mL) was added concentrated sulfuric acid (0.1 mL) in one portion. The reaction mixture was heated at 80° C. overnight. After cooling, the react... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Tertiary amide | null | c1ncc2c(n1)[NH]CCC2 | c1ccccc1.c1ncc2c(n1)[NH]CCC2.c1ccccc1.c1ccccc1 | HO- | C(C)(=O)OCC | 80 | null | CCOC(=O)C(Cc1cnc(Nc2ccccc2)nc1Nc1ccccc1)c1ccc(OC)c(OC)c1>C(C)(=O)OCC>COc1ccc(C2Cc3cnc(Nc4ccccc4)nc3N(c3ccccc3)C2=O)cc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0fc233a13f9f4025aae8312c9520c8fc | COC(=O)C(Cc1cnc(Cl)nc1Cl)c1ccc(OC)cc1.Nc1ccccc1>>COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Cl)c1ccc(OC)cc1 | C(C)(C)N(C(C)C)CC.COC(C(CC=1C(=NC(=NC1)Cl)Cl)C1=CC=C(C=C1)OC)=O.NC1=CC=CC=C1>>COC(C(CC=1C(=NC(=NC1)NC1=CC=CC=C1)Cl)C1=CC=C(C=C1)OC)=O | Cl[c:10]1[n:9][cH:8][c:7]([CH2:6][CH:5]([C:3]([O:2][CH3:1])=[O:4])[c:21]2[cH:22][cH:23][c:24]([O:25][CH3:26])[cH:27][cH:28]2)[c:19]([Cl:20])[n:18]1.[NH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8][n:9][c:10]([NH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[n:18... | COC(=O)C(Cc1cnc(Cl)nc1Cl)c1ccc(OC)cc1.Nc1ccccc1 | COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Cl)c1ccc(OC)cc1 | null | null | C(CCC)O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CCc2cnc(Nc3ccccc3)nc2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | 100 | CELSIUS | null | null | To a solution of 3-(2,4-dichloro-pyrimidin-5-yl)-2-(4-methoxy-phenyl)-propionic acid methyl ester (341 mg, 1.0 mmol) (from Example 1d supra) in n-butanol (10 mL) was added aniline (200 mg, 2.15 mmol) (Aldrich) followed by N,N-diisopropylethylamine (258 mg, 2.0 mmol) (Aldrich) and the reaction mixture was heated at 100°... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1.c1ccccc1 | HCl | C(CCC)O.C(C)(=O)OCC | 100 | null | COC(=O)C(Cc1cnc(Cl)nc1Cl)c1ccc(OC)cc1.Nc1ccccc1>C(CCC)O.C(C)(=O)OCC>COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Cl)c1ccc(OC)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4ec5039ca5784a64aa34542cd4a45e8b | COC(=O)C(Cc1cnc(Cl)nc1Nc1ccccc1)c1ccc(OC)cc1.COc1ccc(N)cn1>>COC(=O)C(Cc1cnc(Nc2ccc(OC)nc2)nc1Nc1ccccc1)c1ccc(OC)cc1 | COC(C(CC=1C(=NC(=NC1)Cl)NC1=CC=CC=C1)C1=CC=C(C=C1)OC)=O.NC=1C=CC(=NC1)OC>>COC(C(CC=1C(=NC(=NC1)NC=1C=NC(=CC1)OC)NC1=CC=CC=C1)C1=CC=C(C=C1)OC)=O | Cl[c:10]1[n:9][cH:8][c:7]([CH2:6][CH:5]([C:3]([O:2][CH3:1])=[O:4])[c:29]2[cH:30][cH:31][c:32]([O:33][CH3:34])[cH:35][cH:36]2)[c:21]([NH:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[n:20]1.[NH2:11][c:12]1[cH:13][cH:14][c:15]([O:16][CH3:17])[n:18][cH:19]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8][n:9][c:10]... | COC(=O)C(Cc1cnc(Cl)nc1Nc1ccccc1)c1ccc(OC)cc1.COc1ccc(N)cn1 | COC(=O)C(Cc1cnc(Nc2ccc(OC)nc2)nc1Nc1ccccc1)c1ccc(OC)cc1 | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CCc2cnc(Nc3cccnc3)nc2Nc2ccccc2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]:[c:11]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9]:[#7;a:10]:[c:11] | null | [] | 110 | CELSIUS | null | null | A mixture of 3-(2-chloro-4-phenylamino-pyrimidin-5-yl)-2-(4-methoxy-phenyl)-propionic acid methyl ester (40 mg, 0.1 mmol) (from Example 12b supra) and 5-amino-2-methoxypyridine (37.2 mg, 0.3 mmol) (Aldrich) was heated at 110° C. for 4 hours. After cooling, the reaction mixture was diluted with ethyl acetate (50 mL) and... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccncc1.c1ccccc1.c1ccccc1 | HCl | C(C)(=O)OCC | 110 | null | COC(=O)C(Cc1cnc(Cl)nc1Nc1ccccc1)c1ccc(OC)cc1.COc1ccc(N)cn1>C(C)(=O)OCC>COC(=O)C(Cc1cnc(Nc2ccc(OC)nc2)nc1Nc1ccccc1)c1ccc(OC)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0cc76f6a46d14480921745d16f372339 | COC(=O)C(Cc1cnc(Nc2ccc(OC)nc2)nc1Nc1ccccc1)c1ccc(OC)cc1>>COc1ccc(C2Cc3cnc(Nc4ccc(OC)nc4)nc3N(c3ccccc3)C2=O)cc1 | COC(C(CC=1C(=NC(=NC1)NC=1C=NC(=CC1)OC)NC1=CC=CC=C1)C1=CC=C(C=C1)OC)=O.S(O)(O)(=O)=O>>COC1=CC=C(C=C1)C1CC2=C(N=C(N=C2)NC=2C=NC(=CC2)OC)N(C1=O)C1=CC=CC=C1 | CO[C:31]([CH:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:34][cH:33]1)[CH2:8][c:9]1[cH:10][n:11][c:12]([NH:13][c:14]2[cH:15][cH:16][c:17]([O:18][CH3:19])[n:20][cH:21]2)[n:22][c:23]1[NH:24][c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1)=[O:32]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]2[CH2:8][c:9]3[cH:10][n:11][c:12]([NH:... | COC(=O)C(Cc1cnc(Nc2ccc(OC)nc2)nc1Nc1ccccc1)c1ccc(OC)cc1 | COc1ccc(C2Cc3cnc(Nc4ccc(OC)nc4)nc3N(c3ccccc3)C2=O)cc1 | null | null | C(C)(=O)O.C(C)(=O)OCC | Miscellaneous | OtherReaction | 4c156791040233b925f911d2344eae0f4fe404d66aa7be29ecbd3d34ec58b9ee | 9fb754180ed1affe0187ff01b0205aba264dc674a9ca4b55d9d8c90d1514940e | O=C1C(c2ccccc2)Cc2cnc(Nc3cccnc3)nc2N1c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[c:4])-[C:5]-[c:6]1:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1-[NH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[C:3](-[c:4])-[C:5]-[c:6]2:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:2-[N;H0;D3;+0:12]-1-[c:13](:[c:14]):[c:15] | null | [] | 80 | CELSIUS | null | null | To a solution of 3-[2-(6-methoxy-pyridin-3-ylamino)-4-phenylamino-pyrimidin-5-yl]-2-(4-methoxy-phenyl)-propionic acid methyl ester (45.0 mg, 0.09 mmol) (from Example 12c supra) in glacial acetic acid (1 mL) was added concentrated sulfuric acid (0.1 mL) in one portion. After heating at 80° C. for 3 hours, the reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Tertiary amide | null | c1ncc2c(n1)[NH]CCC2 | c1ccccc1.c1ncc2c(n1)[NH]CCC2.c1ccncc1.c1ccccc1 | HO- | C(C)(=O)O.C(C)(=O)OCC | 80 | null | COC(=O)C(Cc1cnc(Nc2ccc(OC)nc2)nc1Nc1ccccc1)c1ccc(OC)cc1>C(C)(=O)O.C(C)(=O)OCC>COc1ccc(C2Cc3cnc(Nc4ccc(OC)nc4)nc3N(c3ccccc3)C2=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-16c01f2bbc1b441a947666da49a93695 | CC(C)CN.COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Cl)c1ccc(OC)cc1>>COc1ccc(C2Cc3cnc(Nc4ccccc4)nc3N(CC(C)C)C2=O)cc1 | COC(C(CC=1C(=NC(=NC1)NC1=CC=CC=C1)Cl)C1=CC=C(C=C1)OC)=O.C(C(C)C)N>>C(C(C)C)N1C(C(CC2=C1N=C(N=C2)NC2=CC=CC=C2)C2=CC=C(C=C2)OC)=O | [NH2:22][CH2:23][CH:24]([CH3:25])[CH3:26].CO[C:27]([CH:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:30][cH:29]1)[CH2:8][c:9]1[cH:10][n:11][c:12]([NH:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[n:20][c:21]1Cl)=[O:28]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]2[CH2:8][c:9]3[cH:10][n:11][c:12]([NH:13][c:14]4[cH:15][cH... | CC(C)CN.COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Cl)c1ccc(OC)cc1 | COc1ccc(C2Cc3cnc(Nc4ccccc4)nc3N(CC(C)C)C2=O)cc1 | null | null | null | Acylation | OtherReaction | bb5e32632e312fcbe72f0880005dd462f489b188b3c385ba5cdadc228b7765cb | dc9957f440a17324ed746bff6f1241dbafeab37444abd9e3d9de99ab08a9bd3f | O=C1Nc2nc(Nc3ccccc3)ncc2CC1c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[c:4])-[C:5]-[c:6]1:[c:7]:[#7;a:8]:[c:9](-[#7:10]):[#7;a:11]:[c;H0;D3;+0:12]:1-Cl.[C:13]-[C:14]-[NH2;D1;+0:15]>>[#7:10]-[c:9]1:[#7;a:8]:[c:7]:[c:6]2:[c;H0;D3;+0:12](:[#7;a:11]:1)-[N;H0;D3;+0:15](-[C:14]-[C:13])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[c:4])-[C:5]-2 | null | [] | null | null | null | null | A mixture of 3-(4-chloro-2-phenylamino-pyrimidin-5-yl)-2-(4-methoxy-phenyl)-propionic acid methyl ester (40 mg, 0.1 mmol) (from Example 12a supra) and isobutylamine (2.0 mL) (Aldrich) was heated at reflux for 3 hours. The reaction mixture was concentrated in vacuo and purified by preparative thin layer chromatography t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Primary amine | Tertiary amide | c1cncnc1 | c1ncc2c(n1)[NH]CCC2 | c1ccccc1.c1ncc2c(n1)[NH]CCC2.c1ccccc1 | HCl | null | null | null | CC(C)CN.COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Cl)c1ccc(OC)cc1>>COc1ccc(C2Cc3cnc(Nc4ccccc4)nc3N(CC(C)C)C2=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3442685734594738948d4f348ffe24c3 | COC(=O)C(Cc1cnc(Nc2ccccc2)nc1NCC(C)C)c1ccc(OC)cc1>>COc1ccc(C2Cc3cnc(Nc4ccccc4)nc3N(CC(C)C)C2=O)cc1 | COC(C(CC=1C(=NC(=NC1)NC1=CC=CC=C1)NCC(C)C)C1=CC=C(C=C1)OC)=O.S(O)(O)(=O)=O>>C(C(C)C)N1C(C(CC2=C1N=C(N=C2)NC2=CC=CC=C2)C2=CC=C(C=C2)OC)=O | CO[C:27]([CH:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:30][cH:29]1)[CH2:8][c:9]1[cH:10][n:11][c:12]([NH:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[n:20][c:21]1[NH:22][CH2:23][CH:24]([CH3:25])[CH3:26])=[O:28]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]2[CH2:8][c:9]3[cH:10][n:11][c:12]([NH:13][c:14]4[cH:15][cH:16]... | COC(=O)C(Cc1cnc(Nc2ccccc2)nc1NCC(C)C)c1ccc(OC)cc1 | COc1ccc(C2Cc3cnc(Nc4ccccc4)nc3N(CC(C)C)C2=O)cc1 | null | null | C(C)(=O)O.C(C)(=O)OCC | Miscellaneous | OtherReaction | 4c156791040233b925f911d2344eae0f4fe404d66aa7be29ecbd3d34ec58b9ee | 9fb754180ed1affe0187ff01b0205aba264dc674a9ca4b55d9d8c90d1514940e | O=C1Nc2nc(Nc3ccccc3)ncc2CC1c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[c:4])-[C:5]-[c:6]1:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1-[NH;D2;+0:12]-[C:13]-[C:14]>>[C:14]-[C:13]-[N;H0;D3;+0:12]1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[c:4])-[C:5]-[c:6]2:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:2-1 | null | [] | 85 | CELSIUS | null | null | To the solution of 3-(2-phenylamino-4-isobutylamino-pyrimidin-5-yl)-2-(4-methoxy-phenyl)-propionic acid methyl ester (17.1 mg, 0.04 mmol) in glacial acetic acid (1 mL) was added concentrated sulfuric acid (0.1 mL) in one portion. The reaction mixture was heated at 85° C. overnight. After cooling, the reaction mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Tertiary amide | null | c1ncc2c(n1)[NH]CCC2 | c1ccccc1.c1ncc2c(n1)[NH]CCC2.c1ccccc1 | HO- | C(C)(=O)O.C(C)(=O)OCC | 85 | null | COC(=O)C(Cc1cnc(Nc2ccccc2)nc1NCC(C)C)c1ccc(OC)cc1>C(C)(=O)O.C(C)(=O)OCC>COc1ccc(C2Cc3cnc(Nc4ccccc4)nc3N(CC(C)C)C2=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-38451a5aa7434de7b8a658e3baae8e64 | COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Cl)c1ccc(OC)cc1.NCC1CC1>>COC(=O)C(Cc1cnc(Nc2ccccc2)nc1NCC1CC1)c1ccc(OC)cc1 | COC(C(CC=1C(=NC(=NC1)NC1=CC=CC=C1)Cl)C1=CC=C(C=C1)OC)=O.C1(CC1)CN>>COC(C(CC=1C(=NC(=NC1)NC1=CC=CC=C1)NCC1CC1)C1=CC=C(C=C1)OC)=O | Cl[c:19]1[c:7]([CH2:6][CH:5]([C:3]([O:2][CH3:1])=[O:4])[c:25]2[cH:26][cH:27][c:28]([O:29][CH3:30])[cH:31][cH:32]2)[cH:8][n:9][c:10]([NH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[n:18]1.[NH2:20][CH2:21][CH:22]1[CH2:23][CH2:24]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8][n:9][c:10]([NH:11][c:12]2[cH:13][c... | COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Cl)c1ccc(OC)cc1.NCC1CC1 | COC(=O)C(Cc1cnc(Nc2ccccc2)nc1NCC1CC1)c1ccc(OC)cc1 | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CCc2cnc(Nc3ccccc3)nc2NCC2CC2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8].[C:9]-[C:10]-[NH2;D1;+0:11]>>[#7:4]-[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:11]-[C:10]-[C:9]):[c:7](-[C:8]):[c:6]:[#7;a:5]:1 | null | [] | null | null | 24 | HOUR | A mixture of 3-(4-chloro-2-phenylamino-pyrimidin-5-yl)-2-(4-methoxy-phenyl)-propionic acid methyl ester (45 mg, 0.11 mmol) (from Example 12a supra) and cyclopropylmethylamine (1.0 mL) (Lancaster) was stirred at room temperature for 24 hours. The reaction mixture was then diluted with ethyl acetate (50 mL) and successiv... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1.C1CC1.c1ccccc1 | HCl | C(C)(=O)OCC | null | 24 | COC(=O)C(Cc1cnc(Nc2ccccc2)nc1Cl)c1ccc(OC)cc1.NCC1CC1>C(C)(=O)OCC>COC(=O)C(Cc1cnc(Nc2ccccc2)nc1NCC1CC1)c1ccc(OC)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4c05c88a2a714ca08093234ae20c2763 | COC(=O)C(Cc1cnc(Nc2ccccc2)nc1NCC1CC1)c1ccc(OC)cc1>>COc1ccc(C2Cc3cnc(Nc4ccccc4)nc3N(CC3CC3)C2=O)cc1 | COC(C(CC=1C(=NC(=NC1)NC1=CC=CC=C1)NCC1CC1)C1=CC=C(C=C1)OC)=O.S(O)(O)(=O)=O>>C1(CC1)CN1C(C(CC2=C1N=C(N=C2)NC2=CC=CC=C2)C2=CC=C(C=C2)OC)=O | CO[C:27]([CH:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:30][cH:29]1)[CH2:8][c:9]1[cH:10][n:11][c:12]([NH:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[n:20][c:21]1[NH:22][CH2:23][CH:24]1[CH2:25][CH2:26]1)=[O:28]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]2[CH2:8][c:9]3[cH:10][n:11][c:12]([NH:13][c:14]4[cH:15][cH:16]... | COC(=O)C(Cc1cnc(Nc2ccccc2)nc1NCC1CC1)c1ccc(OC)cc1 | COc1ccc(C2Cc3cnc(Nc4ccccc4)nc3N(CC3CC3)C2=O)cc1 | null | null | C(C)(=O)O.C(C)(=O)OCC | Miscellaneous | OtherReaction | 4c156791040233b925f911d2344eae0f4fe404d66aa7be29ecbd3d34ec58b9ee | 9fb754180ed1affe0187ff01b0205aba264dc674a9ca4b55d9d8c90d1514940e | O=C1C(c2ccccc2)Cc2cnc(Nc3ccccc3)nc2N1CC1CC1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[c:4])-[C:5]-[c:6]1:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1-[NH;D2;+0:12]-[C:13]-[C:14]>>[C:14]-[C:13]-[N;H0;D3;+0:12]1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[c:4])-[C:5]-[c:6]2:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:2-1 | null | [] | 85 | CELSIUS | null | null | To a solution of crude 3-(2-phenylamino-4-cyclopropylmethylamino-pyrimidin-5-yl)-2-(4-methoxy-phenyl)-propionic acid methyl ester (51.3 mg) (from Example 14a supra) in glacial acetic acid (1 mL) was added concentrated sulfuric acid (0.1 mL) in one portion. The reaction mixture was heated at 85° C. for 3 hours. The reac... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Tertiary amide | null | c1ncc2c(n1)[NH]CCC2 | c1ccccc1.c1ncc2c(n1)[NH]CCC2.c1ccccc1.C1CC1 | HO- | C(C)(=O)O.C(C)(=O)OCC | 85 | null | COC(=O)C(Cc1cnc(Nc2ccccc2)nc1NCC1CC1)c1ccc(OC)cc1>C(C)(=O)O.C(C)(=O)OCC>COc1ccc(C2Cc3cnc(Nc4ccccc4)nc3N(CC3CC3)C2=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6250fc794fad4744874872c3b677d7df | CCOC(=O)CC(=O)C(F)(F)F.Oc1ccc(Cc2ccccc2)cc1>>O=c1cc(C(F)(F)F)c2cc(Cc3ccccc3)ccc2o1 | C(C1=CC=CC=C1)C1=CC=C(C=C1)O.C(F)(F)(F)C(=O)CC(=O)OCC.CS(=O)(=O)O>>C(C1=CC=CC=C1)C=1C=C2C(=CC(OC2=CC1)=O)C(F)(F)F | CCO[C:2](=[O:1])[CH2:3][C:4](=O)[C:5]([F:6])([F:7])[F:8].[cH:9]1[cH:10][c:11]([CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][cH:20][c:21]1[OH:22]>>[O:1]=[c:2]1[cH:3][c:4]([C:5]([F:6])([F:7])[F:8])[c:9]2[cH:10][c:11]([CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19][cH:20][c:21]2[o:22]1 | CCOC(=O)CC(=O)C(F)(F)F.Oc1ccc(Cc2ccccc2)cc1 | O=c1cc(C(F)(F)F)c2cc(Cc3ccccc3)ccc2o1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | c2797b9482351455dfd80600e9316aa63917d1f2fdbd6de4297ad8f5b4bfbe49 | 89a9e45776dbe9070f40025f4f55f2a7b9907ff5b9cebad1727718d85938e303 | O=c1ccc2cc(Cc3ccccc3)ccc2o1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[C;H0;D3;+0:4](=O)-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8].[OH;D1;+0:9]-[c:10](:[c:11]):[cH;D2;+0:12]:[c:13]:[c:14]>>[F;D1;H0:6]-[C:5](-[F;D1;H0:7])(-[F;D1;H0:8])-[c;H0;D3;+0:4]1:[cH;D2;+0:3]:[c;H0;D3;+0:1](=[O;D1;H0:2]):[o;H0;D2;+0:9]:[c:10](:[c:11]):[c;H0;D3;+0:1... | 44.3 | [{"value": 44.0, "product": "C(C1=CC=CC=C1)C=1C=C2C(=CC(OC2=CC1)=O)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.3, "product": "C(C1=CC=CC=C1)C=1C=C2C(=CC(OC2=CC1)=O)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | null | null | A stirred suspension of 4-benzylphenol (4.67 g, 25.4 mmol), CF3COCH2CO2Et (7.00 g, 38.0 mmol), & MeSO3H (8.5 mL, 130.9 mmol) was heated at 65° C. for 9 h. On cooling, the mixture was partitioned between Et2O (200 mL) & H2O (50 mL), then the aqueous phase was basicified with 2 M NaOH. The organic layer was separated & w... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Aromatic alcohol | null | c1ccccc1 | c1ccc2occcc2c1 | c1ccc2occcc2c1.c1ccccc1 | HO- | null | 65 | null | CCOC(=O)CC(=O)C(F)(F)F.Oc1ccc(Cc2ccccc2)cc1>>O=c1cc(C(F)(F)F)c2cc(Cc3ccccc3)ccc2o1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9d9accae0f0f4ed7971d30ee908f5890 | CC(C)N.O=c1cc(C(F)(F)F)c2cc(Cc3ccc(S(=O)(=O)Cl)cc3)ccc2[nH]1>>CC(C)NS(=O)(=O)c1ccc(Cc2ccc3[nH]c(=O)cc(C(F)(F)F)c3c2)cc1 | CCOC(=O)C.O=C1NC2=CC=C(C=C2C(=C1)C(F)(F)F)CC1=CC=C(C=C1)S(=O)(=O)Cl.C(C)(C)N>>C(C)(C)NS(=O)(=O)C1=CC=C(C=C1)CC=1C=C2C(=CC(NC2=CC1)=O)C(F)(F)F | [CH3:1][CH:2]([CH3:3])[NH2:4].Cl[S:5](=[O:6])(=[O:7])[c:8]1[cH:9][cH:10][c:11]([CH2:12][c:13]2[cH:14][cH:15][c:16]3[nH:17][c:18](=[O:19])[cH:20][c:21]([C:22]([F:23])([F:24])[F:25])[c:26]3[cH:27]2)[cH:28][cH:29]1>>[CH3:1][CH:2]([CH3:3])[NH:4][S:5](=[O:6])(=[O:7])[c:8]1[cH:9][cH:10][c:11]([CH2:12][c:13]2[cH:14][cH:15][c:... | CC(C)N.O=c1cc(C(F)(F)F)c2cc(Cc3ccc(S(=O)(=O)Cl)cc3)ccc2[nH]1 | CC(C)NS(=O)(=O)c1ccc(Cc2ccc3[nH]c(=O)cc(C(F)(F)F)c3c2)cc1 | null | null | C(Cl)Cl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=c1ccc2cc(Cc3ccccc3)ccc2[nH]1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C;D1;H3:7]-[C:8](-[C;D1;H3:9])-[NH2;D1;+0:10]>>[C;D1;H3:7]-[C:8](-[C;D1;H3:9])-[NH;D2;+0:10]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 45 | [{"value": 45.0, "product": "C(C)(C)NS(=O)(=O)C1=CC=C(C=C1)CC=1C=C2C(=CC(NC2=CC1)=O)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.9, "product": "C(C)(C)NS(=O)(=O)C1=CC=C(C=C1)CC=1C=C2C(=CC(NC2=CC1)=O)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 10 | MINUTE | A stirred solution of 4-(2-oxo4-trifluoromethyl-1,2-dihydroquinolin-6-ylmethyl)-benzenesulfonyl chloride (Preparation 1, 17 mg, 42 μmol) in anhydrous CH2Cl2 (0.5 mL) was treated dropwise with an excess of i-PrNH2 (145 μL, 1680 μmol). After stirring at 20° C. for 10 min, the reaction mixture was submitted to column chro... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccc2ncccc2c1 | HCl | C(Cl)Cl | 20 | 0.166667 | CC(C)N.O=c1cc(C(F)(F)F)c2cc(Cc3ccc(S(=O)(=O)Cl)cc3)ccc2[nH]1>C(Cl)Cl>CC(C)NS(=O)(=O)c1ccc(Cc2ccc3[nH]c(=O)cc(C(F)(F)F)c3c2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c0c4244a11c84b8bb0979a414d3e20be | CCCCN.O=c1cc(C(F)(F)F)c2cc(Cc3ccc(S(=O)(=O)Cl)cc3)ccc2[nH]1>>CCCCNS(=O)(=O)c1ccc(Cc2ccc3[nH]c(=O)cc(C(F)(F)F)c3c2)cc1 | O=C1NC2=CC=C(C=C2C(=C1)C(F)(F)F)CC1=CC=C(C=C1)S(=O)(=O)Cl.C(CCC)N>>C(CCC)NS(=O)(=O)C1=CC=C(C=C1)CC=1C=C2C(=CC(NC2=CC1)=O)C(F)(F)F | [CH3:1][CH2:2][CH2:3][CH2:4][NH2:5].Cl[S:6](=[O:7])(=[O:8])[c:9]1[cH:10][cH:11][c:12]([CH2:13][c:14]2[cH:15][cH:16][c:17]3[nH:18][c:19](=[O:20])[cH:21][c:22]([C:23]([F:24])([F:25])[F:26])[c:27]3[cH:28]2)[cH:29][cH:30]1>>[CH3:1][CH2:2][CH2:3][CH2:4][NH:5][S:6](=[O:7])(=[O:8])[c:9]1[cH:10][cH:11][c:12]([CH2:13][c:14]2[cH... | CCCCN.O=c1cc(C(F)(F)F)c2cc(Cc3ccc(S(=O)(=O)Cl)cc3)ccc2[nH]1 | CCCCNS(=O)(=O)c1ccc(Cc2ccc3[nH]c(=O)cc(C(F)(F)F)c3c2)cc1 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=c1ccc2cc(Cc3ccccc3)ccc2[nH]1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 91.2 | [{"value": 84.0, "product": "C(CCC)NS(=O)(=O)C1=CC=C(C=C1)CC=1C=C2C(=CC(NC2=CC1)=O)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.2, "product": "C(CCC)NS(=O)(=O)C1=CC=C(C=C1)CC=1C=C2C(=CC(NC2=CC1)=O)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-(2-oxo-4-trifluoromethyl-1,2-dihydroquinolin-6-ylmethyl)benzenesulfonyl chloride (Preparation 1, 26 mg, 65 μmol) was reacted with an excess of n-BuNH2 (190 mg, 2600 μmol) by the same procedure used for Example 1. After reaction, the solvents were evaporated off under reduced pressure & the residue partitioned between... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccc2ncccc2c1 | HCl | null | null | null | CCCCN.O=c1cc(C(F)(F)F)c2cc(Cc3ccc(S(=O)(=O)Cl)cc3)ccc2[nH]1>>CCCCNS(=O)(=O)c1ccc(Cc2ccc3[nH]c(=O)cc(C(F)(F)F)c3c2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cbdf752bc7c248abbc942b21d3cffc35 | NCc1ccccc1.O=c1cc(C(F)(F)F)c2cc(Cc3ccc(S(=O)(=O)Cl)cc3)ccc2[nH]1>>O=c1cc(C(F)(F)F)c2cc(Cc3ccc(S(=O)(=O)NCc4ccccc4)cc3)ccc2[nH]1 | O=C1NC2=CC=C(C=C2C(=C1)C(F)(F)F)CC1=CC=C(C=C1)S(=O)(=O)Cl.C(C1=CC=CC=C1)N>>C(C1=CC=CC=C1)NS(=O)(=O)C1=CC=C(C=C1)CC=1C=C2C(=CC(NC2=CC1)=O)C(F)(F)F | [NH2:20][CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1.Cl[S:17]([c:16]1[cH:15][cH:14][c:13]([CH2:12][c:11]2[cH:10][c:9]3[c:4]([C:5]([F:6])([F:7])[F:8])[cH:3][c:2](=[O:1])[nH:33][c:32]3[cH:31][cH:30]2)[cH:29][cH:28]1)(=[O:18])=[O:19]>>[O:1]=[c:2]1[cH:3][c:4]([C:5]([F:6])([F:7])[F:8])[c:9]2[cH:10][c:11]([CH2:12][c:1... | NCc1ccccc1.O=c1cc(C(F)(F)F)c2cc(Cc3ccc(S(=O)(=O)Cl)cc3)ccc2[nH]1 | O=c1cc(C(F)(F)F)c2cc(Cc3ccc(S(=O)(=O)NCc4ccccc4)cc3)ccc2[nH]1 | null | null | null | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=c1ccc2cc(Cc3ccc(S(=O)(=O)NCc4ccccc4)cc3)ccc2[nH]1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[C:8]-[c:9]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:7]-[C:8]-[c:9])-[c:4](:[c:5]):[c:6] | 61.9 | [{"value": 61.0, "product": "C(C1=CC=CC=C1)NS(=O)(=O)C1=CC=C(C=C1)CC=1C=C2C(=CC(NC2=CC1)=O)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.9, "product": "C(C1=CC=CC=C1)NS(=O)(=O)C1=CC=C(C=C1)CC=1C=C2C(=CC(NC2=CC1)=O)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of 4-(2-oxo-4-trifluoromethyl-1,2-dihydroquinolin-6-ylmethyl)benzene-sulfonyl chloride (Preparation 1, 26 mg, 65 μmol) with an excess of BnNH2 (280 mg, 2600 μmol), by the method described for Example 1, generated the title compound (19 mg, 61%): δH ((CD3)2SO)=3.95 (d, 2H), 4.15 (s, 2H), 7.00 (s, 1H), 7.15–7.25... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccc2ncccc2c1.c1ccccc1.c1ccccc1 | HCl | null | null | null | NCc1ccccc1.O=c1cc(C(F)(F)F)c2cc(Cc3ccc(S(=O)(=O)Cl)cc3)ccc2[nH]1>>O=c1cc(C(F)(F)F)c2cc(Cc3ccc(S(=O)(=O)NCc4ccccc4)cc3)ccc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1b0ea0d9e5564b47bba4617ca3b34571 | Oc1ccccc1>>CCCC(=O)O.CCCCCC | C(=O)([O-])[O-].[K+].[K+].C1(=CC=CC=C1)O>>CCCCCC.C(C)CC(=O)O | O[c:1]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[CH3:1][CH2:2][CH2:3][C:4](=[O:5])[OH:6].[CH3:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12] | Oc1ccccc1 | CCCC(=O)O.CCCCCC | null | null | C(C)#N | Miscellaneous | OtherReaction | fa618f5452cf8d39f77ddf913f06d82fa923daf39ff606905a5341ace0bd65f7 | 45b5980231007c8958a67317ea24d97c426ebaa02282f06c70b75eb4ce8f769b | null | O-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1>>[C;D1;H3:7]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[CH3;D1;+0:6].[C:8]-[C:9]-[CH3;D1;+0:1] | null | [] | null | null | 1 | HOUR | O-methyl(ethyl) O-aryl chlorothiophosphate, which was obtained by reacting O-methyl(ethyl) dichlorothiophosphate with phenol, was reacted with aminocarboxylic acid to give a hapten for immunoassay of phosphorothioate pesticides: to 46 mmol of O-methyl(ethyl) dichlorothiophosphate (10) dissolved in 30 mL of acetonitrile... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Carboxylic acid | c1ccccc1 | null | null | null | C(C)#N | null | 1 | Oc1ccccc1>C(C)#N>CCCC(=O)O.CCCCCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9ddc7e8714f848aa8be681a6021447c6 | CCOc1nc2cccc(C(=O)OC(C)OC(=O)OC3CCCCC3)c2n1Cc1ccc(-c2ccccc2-c2nnnn2C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1>>CCOc1nc2cccc(C(=O)OC(C)OC(=O)OC3CCCCC3)c2n1Cc1ccc(-c2ccccc2-c2nn[nH]n2)cc1 | C1(=CC=CC=C1)C.CCOC1=NC2=CC=CC(=C2N1CC3=CC=C(C=C3)C4=CC=CC=C4C5=NN=NN5C(C6=CC=CC=C6)(C7=CC=CC=C7)C8=CC=CC=C8)C(=O)OC(C)OC(=O)OC9CCCCC9.C(=O)O>>CCOC1=NC=2C=CC=C(C2N1CC=3C=CC(=CC3)C=4C=CC=CC4C5=NNN=N5)C(=O)OC(C)OC(=O)OC6CCCCC6 | c1ccc(C(c2ccccc2)(c2ccccc2)[n:43]2[c:39](-[c:38]3[c:33](-[c:32]4[cH:31][cH:30][c:29]([CH2:28][n:27]5[c:4]([O:3][CH2:2][CH3:1])[n:5][c:6]6[cH:7][cH:8][cH:9][c:10]([C:11](=[O:12])[O:13][CH:14]([CH3:15])[O:16][C:17](=[O:18])[O:19][CH:20]7[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]7)[c:26]65)[cH:45][cH:44]4)[cH:34][cH:35][cH:... | CCOc1nc2cccc(C(=O)OC(C)OC(=O)OC3CCCCC3)c2n1Cc1ccc(-c2ccccc2-c2nnnn2C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | CCOc1nc2cccc(C(=O)OC(C)OC(=O)OC3CCCCC3)c2n1Cc1ccc(-c2ccccc2-c2nn[nH]n2)cc1 | null | null | CO | Deprotection | OtherReaction | bee75b2c80e33b32bc1cd2f4da11999883aae9c37547c33804aee63f103057c6 | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | O=C(OCOC(=O)c1cccc2ncn(Cc3ccc(-c4ccccc4-c4nn[nH]n4)cc3)c12)OC1CCCCC1 | [c:1]-[c:2]1:[#7;a:3]:[#7;a:4]:[n;H0;D2;+0:5]:[n;H0;D3;+0:6]:1-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[c:1]-[c:2]1:[#7;a:3]:[#7;a:4]:[nH;D2;+0:5]:[n;H0;D2;+0:6]:1 | null | [] | null | null | null | null | Typically, the deprotection step comprises heating to reflux trityl candesartan cilexetil in methanol. Optionally, the deprotection solvent mixture further comprises an organic solvent, such as toluene, and/or an acid, such as formic acid. The cilexetil trityl candesartan is heated to reflux until a clear solution is o... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1nnn[nH]1 | c1nnn[nH]1 | c1nc2ccccc2[nH]1.C1CCCCC1.c1ccccc1.c1ccccc1.c1nnn[nH]1 | Other | CO | null | null | CCOc1nc2cccc(C(=O)OC(C)OC(=O)OC3CCCCC3)c2n1Cc1ccc(-c2ccccc2-c2nnnn2C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1>CO>CCOc1nc2cccc(C(=O)OC(C)OC(=O)OC3CCCCC3)c2n1Cc1ccc(-c2ccccc2-c2nn[nH]n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cf2755c8bda948af8d1a138c3269dbe4 | CCOc1nc2cccc(C(=O)OC(C)OC(=O)OC3CCCCC3)c2n1Cc1ccc(-c2ccccc2-c2nnnn2C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1>>CCOc1nc2cccc(C(=O)OC(C)OC(=O)OC3CCCCC3)c2n1Cc1ccc(-c2ccccc2-c2nn[nH]n2)cc1 | CCOC1=NC2=CC=CC(=C2N1CC3=CC=C(C=C3)C4=CC=CC=C4C5=NN=NN5C(C6=CC=CC=C6)(C7=CC=CC=C7)C8=CC=CC=C8)C(=O)OC(C)OC(=O)OC9CCCCC9.C1(=CC=CC=C1)C.CO>>CCOC1=NC=2C=CC=C(C2N1CC=3C=CC(=CC3)C=4C=CC=CC4C5=NNN=N5)C(=O)OC(C)OC(=O)OC6CCCCC6 | c1ccc(C(c2ccccc2)(c2ccccc2)[n:43]2[c:39](-[c:38]3[c:33](-[c:32]4[cH:31][cH:30][c:29]([CH2:28][n:27]5[c:4]([O:3][CH2:2][CH3:1])[n:5][c:6]6[cH:7][cH:8][cH:9][c:10]([C:11](=[O:12])[O:13][CH:14]([CH3:15])[O:16][C:17](=[O:18])[O:19][CH:20]7[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]7)[c:26]65)[cH:45][cH:44]4)[cH:34][cH:35][cH:... | CCOc1nc2cccc(C(=O)OC(C)OC(=O)OC3CCCCC3)c2n1Cc1ccc(-c2ccccc2-c2nnnn2C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | CCOc1nc2cccc(C(=O)OC(C)OC(=O)OC3CCCCC3)c2n1Cc1ccc(-c2ccccc2-c2nn[nH]n2)cc1 | null | null | O | Deprotection | OtherReaction | bee75b2c80e33b32bc1cd2f4da11999883aae9c37547c33804aee63f103057c6 | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | O=C(OCOC(=O)c1cccc2ncn(Cc3ccc(-c4ccccc4-c4nn[nH]n4)cc3)c12)OC1CCCCC1 | [c:1]-[c:2]1:[#7;a:3]:[#7;a:4]:[n;H0;D2;+0:5]:[n;H0;D3;+0:6]:1-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[c:1]-[c:2]1:[#7;a:3]:[#7;a:4]:[nH;D2;+0:5]:[n;H0;D2;+0:6]:1 | null | [] | null | null | null | null | A mixture of trityl candesartan cilexetil (20 g, 23.45 mmol), toluene (60 ml), methanol (60 ml), and water (1 ml) was gently refluxed for about 12 h. The reaction was monitored by HPLC. The solution volume was reduced by evaporation under reduced pressure (30 mbar) at a temperature of about 55° C. 60° C. to obtain visc... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1nnn[nH]1 | c1nnn[nH]1 | c1nc2ccccc2[nH]1.C1CCCCC1.c1ccccc1.c1ccccc1.c1nnn[nH]1 | Other | O | null | null | CCOc1nc2cccc(C(=O)OC(C)OC(=O)OC3CCCCC3)c2n1Cc1ccc(-c2ccccc2-c2nnnn2C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1>O>CCOc1nc2cccc(C(=O)OC(C)OC(=O)OC3CCCCC3)c2n1Cc1ccc(-c2ccccc2-c2nn[nH]n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-81a6ecf14d144689918ebb497d08a2d5 | CCOc1nc2cccc(C(=O)OC(C)OC(=O)OC3CCCCC3)c2n1Cc1ccc(-c2ccccc2-c2nnnn2C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1>>CCOc1nc2cccc(C(=O)OC(C)OC(=O)OC3CCCCC3)c2n1Cc1ccc(-c2ccccc2-c2nn[nH]n2)cc1 | CCOC1=NC2=CC=CC(=C2N1CC3=CC=C(C=C3)C4=CC=CC=C4C5=NN=NN5C(C6=CC=CC=C6)(C7=CC=CC=C7)C8=CC=CC=C8)C(=O)OC(C)OC(=O)OC9CCCCC9.C1(=CC=CC=C1)C.CO>>CCOC1=NC=2C=CC=C(C2N1CC=3C=CC(=CC3)C=4C=CC=CC4C5=NNN=N5)C(=O)OC(C)OC(=O)OC6CCCCC6 | c1ccc(C(c2ccccc2)(c2ccccc2)[n:43]2[c:39](-[c:38]3[c:33](-[c:32]4[cH:31][cH:30][c:29]([CH2:28][n:27]5[c:4]([O:3][CH2:2][CH3:1])[n:5][c:6]6[cH:7][cH:8][cH:9][c:10]([C:11](=[O:12])[O:13][CH:14]([CH3:15])[O:16][C:17](=[O:18])[O:19][CH:20]7[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]7)[c:26]65)[cH:45][cH:44]4)[cH:34][cH:35][cH:... | CCOc1nc2cccc(C(=O)OC(C)OC(=O)OC3CCCCC3)c2n1Cc1ccc(-c2ccccc2-c2nnnn2C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | CCOc1nc2cccc(C(=O)OC(C)OC(=O)OC3CCCCC3)c2n1Cc1ccc(-c2ccccc2-c2nn[nH]n2)cc1 | null | null | O | Deprotection | OtherReaction | bee75b2c80e33b32bc1cd2f4da11999883aae9c37547c33804aee63f103057c6 | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | O=C(OCOC(=O)c1cccc2ncn(Cc3ccc(-c4ccccc4-c4nn[nH]n4)cc3)c12)OC1CCCCC1 | [c:1]-[c:2]1:[#7;a:3]:[#7;a:4]:[n;H0;D2;+0:5]:[n;H0;D3;+0:6]:1-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[c:1]-[c:2]1:[#7;a:3]:[#7;a:4]:[nH;D2;+0:5]:[n;H0;D2;+0:6]:1 | null | [] | null | null | null | null | A mixture of trityl candesartan cilexetil (20 g, 23.45 mmol), toluene (60 ml), methanol (120 ml), and water (1 ml) was gently refluxed for about 5 h. The reaction progress was monitored by HPLC. The solution volume was reduced by evaporation under reduced pressure (30 mbar) at a temperature of about 55° C. to 60° C. to... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1nnn[nH]1 | c1nnn[nH]1 | c1nc2ccccc2[nH]1.C1CCCCC1.c1ccccc1.c1ccccc1.c1nnn[nH]1 | Other | O | null | null | CCOc1nc2cccc(C(=O)OC(C)OC(=O)OC3CCCCC3)c2n1Cc1ccc(-c2ccccc2-c2nnnn2C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1>O>CCOc1nc2cccc(C(=O)OC(C)OC(=O)OC3CCCCC3)c2n1Cc1ccc(-c2ccccc2-c2nn[nH]n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-058db254e82c45b7899abb07338a96ad | CCOc1nc2cccc(C(=O)OC(C)OC(=O)OC3CCCCC3)c2n1Cc1ccc(-c2ccccc2-c2nnnn2C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1>>CCOc1nc2cccc(C(=O)OC(C)OC(=O)OC3CCCCC3)c2n1Cc1ccc(-c2ccccc2-c2nn[nH]n2)cc1 | CCOC1=NC2=CC=CC(=C2N1CC3=CC=C(C=C3)C4=CC=CC=C4C5=NN=NN5C(C6=CC=CC=C6)(C7=CC=CC=C7)C8=CC=CC=C8)C(=O)OC(C)OC(=O)OC9CCCCC9.CO>>CCOC1=NC=2C=CC=C(C2N1CC=3C=CC(=CC3)C=4C=CC=CC4C5=NNN=N5)C(=O)OC(C)OC(=O)OC6CCCCC6 | c1ccc(C(c2ccccc2)(c2ccccc2)[n:43]2[c:39](-[c:38]3[c:33](-[c:32]4[cH:31][cH:30][c:29]([CH2:28][n:27]5[c:4]([O:3][CH2:2][CH3:1])[n:5][c:6]6[cH:7][cH:8][cH:9][c:10]([C:11](=[O:12])[O:13][CH:14]([CH3:15])[O:16][C:17](=[O:18])[O:19][CH:20]7[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]7)[c:26]65)[cH:45][cH:44]4)[cH:34][cH:35][cH:... | CCOc1nc2cccc(C(=O)OC(C)OC(=O)OC3CCCCC3)c2n1Cc1ccc(-c2ccccc2-c2nnnn2C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | CCOc1nc2cccc(C(=O)OC(C)OC(=O)OC3CCCCC3)c2n1Cc1ccc(-c2ccccc2-c2nn[nH]n2)cc1 | null | null | O | Deprotection | OtherReaction | bee75b2c80e33b32bc1cd2f4da11999883aae9c37547c33804aee63f103057c6 | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | O=C(OCOC(=O)c1cccc2ncn(Cc3ccc(-c4ccccc4-c4nn[nH]n4)cc3)c12)OC1CCCCC1 | [c:1]-[c:2]1:[#7;a:3]:[#7;a:4]:[n;H0;D2;+0:5]:[n;H0;D3;+0:6]:1-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[c:1]-[c:2]1:[#7;a:3]:[#7;a:4]:[nH;D2;+0:5]:[n;H0;D2;+0:6]:1 | null | [] | null | null | null | null | A mixture of trityl candesartan cilexetil (20 g, 23.45 mmol), methanol (200 ml), and water (1 ml) was gently refluxed for about 16–17 h. The reaction progress was monitored by HPLC. The solution volume was reduced by evaporation under reduced pressure (30 mbar) at a temperature of 55° C. to 60° C. to obtain viscous oil... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1nnn[nH]1 | c1nnn[nH]1 | c1nc2ccccc2[nH]1.C1CCCCC1.c1ccccc1.c1ccccc1.c1nnn[nH]1 | Other | O | null | null | CCOc1nc2cccc(C(=O)OC(C)OC(=O)OC3CCCCC3)c2n1Cc1ccc(-c2ccccc2-c2nnnn2C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1>O>CCOc1nc2cccc(C(=O)OC(C)OC(=O)OC3CCCCC3)c2n1Cc1ccc(-c2ccccc2-c2nn[nH]n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c3f0ffdbe3a147e5b8c4869da58c2e70 | O=C(O)[C@H]1CN(C(=O)OCc2ccccc2)CCN1.O=[N+]([O-])c1cc(F)c(Cl)c(Cl)c1>>O=C(O)[C@H]1CN(C(=O)OCc2ccccc2)CCN1c1cc(Cl)c(Cl)cc1[N+](=O)[O-] | C(=O)(OCC1=CC=CC=C1)N1C[C@@H](NCC1)C(=O)O.ClC1=C(C(=CC(=C1)[N+](=O)[O-])F)Cl.O.CN(C=O)C>>C(=O)(OCC1=CC=CC=C1)N1C[C@@H](N(CC1)C1=C(C=C(C(=C1)Cl)Cl)[N+](=O)[O-])C(=O)O | [O:1]=[C:2]([OH:3])[C@H:4]1[CH2:5][N:6]([C:7](=[O:8])[O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH2:17][CH2:18][NH:19]1.F[c:24]1[c:22]([Cl:23])[c:21]([Cl:25])[cH:20][c:27]([N+:28](=[O:29])[O-:30])[cH:26]1>>[O:1]=[C:2]([OH:3])[C@H:4]1[CH2:5][N:6]([C:7](=[O:8])[O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:1... | O=C(O)[C@H]1CN(C(=O)OCc2ccccc2)CCN1.O=[N+]([O-])c1cc(F)c(Cl)c(Cl)c1 | O=C(O)[C@H]1CN(C(=O)OCc2ccccc2)CCN1c1cc(Cl)c(Cl)cc1[N+](=O)[O-] | null | null | C(C)N(CC)CC | Functional Group Interconversion | OtherReaction | dd7353043b9be5eeb7c17f31c462d2a9bc114e2e9d3d13fac984a45e43d4b2cd | f53962194c2216e08e7685a4ca49aa3deb09685291e557c1a0b20a4dc85a77b5 | O=C(OCc1ccccc1)N1CCN(c2ccccc2)CC1 | F-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[#7;+:4]):[cH;D2;+0:5]:[c;H0;D3;+0:6](-[Cl;H0;D1;+0:7]):[c:8]:1-[Cl;D1;H0:9].[O;D1;H0:10]=[C:11](-[O;D1;H1:12])-[C:13]1-[C:14]-[#7:15]-[C:16]-[C:17]-[NH;D2;+0:18]-1>>[#7;+:4]-[c:3]1:[c:2]:[c;H0;D3;+0:1](-[Cl;H0;D1;+0:7]):[c:8](-[Cl;D1;H0:9]):[cH;D2;+0:6]:[c;H0;D3;+0:5]:1-[N;H0;D3;+0:18]1-... | 94.2 | [{"value": 94.2, "product": "C(=O)(OCC1=CC=CC=C1)N1C[C@@H](N(CC1)C1=C(C=C(C(=C1)Cl)Cl)[N+](=O)[O-])C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.2, "product": "C(=O)(OCC1=CC=CC=C1)N1C[C@@H](N(CC1)C1=C(C=C(C(=C1)Cl)Cl)[N+](=O)[O-])C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | 50 | CELSIUS | null | null | To a slurry containing 5.0 g of (R)-4-carbobenzyloxypiperazine-2-carboxylic acid, 4.2 g of 1,2-dichloro-fluoro-5-nitrobenzene, 85 mL of water and 170 mL of dimethylformamide is added slowly 5.3 mL of triethylamine. The solution is heated to 50° C. for 5 hours, then at ambient temperature overnight. The dark orange solu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Secondary amine | Aromatic halide.Tertiary amine | C1CNCC[NH]1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | HF | C(C)N(CC)CC | 50 | null | O=C(O)[C@H]1CN(C(=O)OCc2ccccc2)CCN1.O=[N+]([O-])c1cc(F)c(Cl)c(Cl)c1>C(C)N(CC)CC>O=C(O)[C@H]1CN(C(=O)OCc2ccccc2)CCN1c1cc(Cl)c(Cl)cc1[N+](=O)[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5afd81cea1474aa1b6e2b9885c61c1a1 | O=C(O)C1CN(C(=O)OCc2ccccc2)CCN1.O=[N+]([O-])c1ccc(Cl)c(Cl)c1Cl>>O=C(O)C1CN(C(=O)OCc2ccccc2)CCN1c1c([N+](=O)[O-])ccc(Cl)c1Cl | ClC1=C(C=CC(=C1Cl)Cl)[N+](=O)[O-].C(=O)(OCC1=CC=CC=C1)N1CC(NCC1)C(=O)O>>C(=O)(OCC1=CC=CC=C1)N1CC(N(CC1)C1=C(C=CC(=C1Cl)Cl)[N+](=O)[O-])C(=O)O | [O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][N:6]([C:7](=[O:8])[O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH2:17][CH2:18][NH:19]1.Cl[c:20]1[c:21]([N+:22](=[O:23])[O-:24])[cH:25][cH:26][c:27]([Cl:28])[c:29]1[Cl:30]>>[O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][N:6]([C:7](=[O:8])[O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][... | O=C(O)C1CN(C(=O)OCc2ccccc2)CCN1.O=[N+]([O-])c1ccc(Cl)c(Cl)c1Cl | O=C(O)C1CN(C(=O)OCc2ccccc2)CCN1c1c([N+](=O)[O-])ccc(Cl)c1Cl | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 75de53007ec0cb91435746fdefbf3b121f745fc71ddebd19c6e45a5212b3f56a | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=C(OCc1ccccc1)N1CCN(c2ccccc2)CC1 | Cl-[c;H0;D3;+0:1](:[c:2](-[#7;+:3]):[c:4]):[c:5](-[Cl;D1;H0:6]):[c:7].[O;D1;H0:8]=[C:9](-[O;D1;H1:10])-[C:11]1-[C:12]-[#7:13]-[C:14]-[C:15]-[NH;D2;+0:16]-1>>[#7;+:3]-[c:2](:[c:4]):[c;H0;D3;+0:1](-[N;H0;D3;+0:16]1-[C:15]-[C:14]-[#7:13]-[C:12]-[C:11]-1-[C:9](=[O;D1;H0:8])-[O;D1;H1:10]):[c:5](-[Cl;D1;H0:6]):[c:7] | 43.6 | [{"value": 43.6, "product": "C(=O)(OCC1=CC=CC=C1)N1CC(N(CC1)C1=C(C=CC(=C1Cl)Cl)[N+](=O)[O-])C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | By the same procedure described for Example 7 A, from 0.86 g of 2,3,4-trichloro-nitro-benzene and 1.0 g of 4-carbobenzyloxypiperazine-2-carboxylic acid, there was obtained 0.75 g of the desired product as a brown oil.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | HCl | null | null | null | O=C(O)C1CN(C(=O)OCc2ccccc2)CCN1.O=[N+]([O-])c1ccc(Cl)c(Cl)c1Cl>>O=C(O)C1CN(C(=O)OCc2ccccc2)CCN1c1c([N+](=O)[O-])ccc(Cl)c1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e737455c44f54ee7a737fd439bc448cd | O=C(O)C1CN(C(=O)OCc2ccccc2)CCN1c1c([N+](=O)[O-])ccc(Cl)c1Cl>>O=C1Nc2ccc(Cl)c(Cl)c2N2CCN(C(=O)OCc3ccccc3)CC12 | C(=O)(OCC1=CC=CC=C1)N1CC(N(CC1)C1=C(C=CC(=C1Cl)Cl)[N+](=O)[O-])C(=O)O>>C(=O)(OCC1=CC=CC=C1)N1CC2N(C3=C(C(=CC=C3NC2=O)Cl)Cl)CC1 | O=[N+:3]([O-])[c:4]1[cH:5][cH:6][c:7]([Cl:8])[c:9]([Cl:10])[c:11]1[N:12]1[CH2:13][CH2:14][N:15]([C:16](=[O:17])[O:18][CH2:19][c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[CH2:26][CH:27]1[C:2](O)=[O:1]>>[O:1]=[C:2]1[NH:3][c:4]2[cH:5][cH:6][c:7]([Cl:8])[c:9]([Cl:10])[c:11]2[N:12]2[CH2:13][CH2:14][N:15]([C:16](=[O:17])[O:1... | O=C(O)C1CN(C(=O)OCc2ccccc2)CCN1c1c([N+](=O)[O-])ccc(Cl)c1Cl | O=C1Nc2ccc(Cl)c(Cl)c2N2CCN(C(=O)OCc3ccccc3)CC12 | null | [Fe] | null | Functional Group Interconversion | OtherReaction | 7913e2370debe9ca401402b204be4fcb57433cf616af0012527eda5fc5434821 | 98c112fcc8dd821704dc378798368c2081a2acc574356674c70af3e59954ee0d | O=C1Nc2ccccc2N2CCN(C(=O)OCc3ccccc3)CC12 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4]-[#7:5])-[#7:6](-[c:7]:[c:8](-[N+;H0;D3:9](=O)-[O-]):[c:10])-[C:11]>>[#7:5]-[C:4]-[C:3]1-[#7:6](-[C:11])-[c:7]:[c:8](:[c:10])-[NH;D2;+0:9]-[C;H0;D3;+0:1]-1=[O;D1;H0:2] | 50.7 | [{"value": 49.0, "product": "C(=O)(OCC1=CC=CC=C1)N1CC2N(C3=C(C(=CC=C3NC2=O)Cl)Cl)CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.7, "product": "C(=O)(OCC1=CC=CC=C1)N1CC2N(C3=C(C(=CC=C3NC2=O)Cl)Cl)CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | By the same procedure described for Example 7B, from 0.75 g of 4-carbobenzyloxy-1-(5,6-dichloro-2-nitrophenyl)piperazine-2-carboxylic acid and 0.28 g of iron powder, there was obtained 0.34 g (49%) of the desired product as a brown solid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | c1ccc2c(c1)NCC1C[NH]CCN21 | c1ccc2c(c1)NCC1C[NH]CCN21.c1ccccc1 | Other | [Fe] | null | null | O=C(O)C1CN(C(=O)OCc2ccccc2)CCN1c1c([N+](=O)[O-])ccc(Cl)c1Cl>[Fe]>O=C1Nc2ccc(Cl)c(Cl)c2N2CCN(C(=O)OCc3ccccc3)CC12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0b831c4cee1d41bab17511239d6c8b09 | O=C(O)C1CN(C(=O)OCc2ccccc2)CCN1.O=[N+]([O-])c1cc(F)c(F)cc1F>>O=C(O)C1CN(C(=O)OCc2ccccc2)CCN1c1cc(F)c(F)cc1[N+](=O)[O-] | C(=O)(OCC1=CC=CC=C1)N1CC(NCC1)C(=O)O.FC1=C(C=C(C(=C1)[N+](=O)[O-])F)F>>C(=O)(OCC1=CC=CC=C1)N1CC(N(CC1)C1=C(C=C(C(=C1)F)F)[N+](=O)[O-])C(=O)O | [O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][N:6]([C:7](=[O:8])[O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH2:17][CH2:18][NH:19]1.F[c:20]1[cH:21][c:22]([F:23])[c:24]([F:25])[cH:26][c:27]1[N+:28](=[O:29])[O-:30]>>[O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][N:6]([C:7](=[O:8])[O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:... | O=C(O)C1CN(C(=O)OCc2ccccc2)CCN1.O=[N+]([O-])c1cc(F)c(F)cc1F | O=C(O)C1CN(C(=O)OCc2ccccc2)CCN1c1cc(F)c(F)cc1[N+](=O)[O-] | null | null | null | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 75de53007ec0cb91435746fdefbf3b121f745fc71ddebd19c6e45a5212b3f56a | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=C(OCc1ccccc1)N1CCN(c2ccccc2)CC1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[O;D1;H0:7]=[C:8](-[O;D1;H1:9])-[C:10]1-[C:11]-[#7:12]-[C:13]-[C:14]-[NH;D2;+0:15]-1>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:15]1-[C:14]-[C:13]-[#7:12]-[C:11]-[C:10]-1-[C:8](=[O;D1;H0:7])-[O;D1;H1:9]):[c:2]:[c:3] | 16.7 | [{"value": 16.7, "product": "C(=O)(OCC1=CC=CC=C1)N1CC(N(CC1)C1=C(C=C(C(=C1)F)F)[N+](=O)[O-])C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By the same procedure described for example 2 method 2B, from 1.5 g of racemic 4-carbobenzyloxypiperazine-2-carboxylic acid and 1,2,4-trifluoro-5-nitro-benzene, there was obtained 0.4 g (16.7%) of title compound as an orange-red residue.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1 | HF | null | null | null | O=C(O)C1CN(C(=O)OCc2ccccc2)CCN1.O=[N+]([O-])c1cc(F)c(F)cc1F>>O=C(O)C1CN(C(=O)OCc2ccccc2)CCN1c1cc(F)c(F)cc1[N+](=O)[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c6bf3ab9737a4f4b86487ecc57403964 | CN(C)CC1CCc2c(c3ccccc3n2C)C1=O.Cc1ncc[nH]1>>Cc1nccn1CC1CCc2c(c3ccccc3n2C)C1=O | Cl.CN(C)CC1CCC=2N(C3=CC=CC=C3C2C1=O)C.CC=1NC=CN1.O>>CC1=NC=CN1CC2CCC3=C(C=4C=CC=CC4N3C)C2=O | CN(C)[CH2:7][CH:8]1[CH2:9][CH2:10][c:11]2[c:12]([c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[n:19]2[CH3:20])[C:21]1=[O:22].[CH3:1][c:2]1[n:3][cH:4][cH:5][nH:6]1>>[CH3:1][c:2]1[n:3][cH:4][cH:5][n:6]1[CH2:7][CH:8]1[CH2:9][CH2:10][c:11]2[c:12]([c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[n:19]2[CH3:20])[C:21]1=[O:22] | CN(C)CC1CCc2c(c3ccccc3n2C)C1=O.Cc1ncc[nH]1 | Cc1nccn1CC1CCc2c(c3ccccc3n2C)C1=O | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | baea70c3ed4e23fb3981a811d0c5d5797285f34961f974af088dbe9c4c60dd14 | 7c33147a6170e63e1fbe1110c4ce069481be57a96b70c4a5a6d7e8253f321bd2 | O=C1c2c([nH]c3ccccc23)CCC1Cn1ccnc1 | C-N(-C)-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[c:6]:[c:7]:[#7;a:8].[C;D1;H3:9]-[c:10]1:[#7;a:11]:[c:12]:[c:13]:[nH;D2;+0:14]:1>>[#7;a:8]:[c:7]:[c:6]-[C:4](=[O;D1;H0:5])-[C:2](-[CH2;D2;+0:1]-[n;H0;D3;+0:14]1:[c:13]:[c:12]:[#7;a:11]:[c:10]:1-[C;D1;H3:9])-[C:3] | 97 | [{"value": 96.4, "product": "CC1=NC=CN1CC2CCC3=C(C=4C=CC=CC4N3C)C2=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.0, "product": "CC1=NC=CN1CC2CCC3=C(C=4C=CC=CC4N3C)C2=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | 3-[(Dimethylamino)methyl]-1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one hydrochloride (10 g, 34 mmol) and 2-methylimidazole (16.8 g, 205 mmol, 6.0 eq.) were suspended in mixture of water (75 ml) and dimethyl formamide (37.5 ml). The reaction mixture was heated to reflux (102–103° C.) and stirred for a further 6 hours a... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | c1c[nH]cn1 | c1ncc[nH]1 | c1ncc[nH]1.C1[CH]CCc2[nH]c3ccccc3c21 | Other | CN(C=O)C | null | 6 | CN(C)CC1CCc2c(c3ccccc3n2C)C1=O.Cc1ncc[nH]1>CN(C=O)C>Cc1nccn1CC1CCc2c(c3ccccc3n2C)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4fddb17bac00436194745b17dd4dce0d | CN(C)CC1CCc2c(c3ccccc3n2C)C1=O.Cc1ncc[nH]1>>Cc1nccn1CC1CCc2c(c3ccccc3n2C)C1=O | Cl.CN(C)CC1CCC=2N(C3=CC=CC=C3C2C1=O)C.CC=1NC=CN1.O>>CC1=NC=CN1CC2CCC3=C(C=4C=CC=CC4N3C)C2=O | CN(C)[CH2:7][CH:8]1[CH2:9][CH2:10][c:11]2[c:12]([c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[n:19]2[CH3:20])[C:21]1=[O:22].[CH3:1][c:2]1[n:3][cH:4][cH:5][nH:6]1>>[CH3:1][c:2]1[n:3][cH:4][cH:5][n:6]1[CH2:7][CH:8]1[CH2:9][CH2:10][c:11]2[c:12]([c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[n:19]2[CH3:20])[C:21]1=[O:22] | CN(C)CC1CCc2c(c3ccccc3n2C)C1=O.Cc1ncc[nH]1 | Cc1nccn1CC1CCc2c(c3ccccc3n2C)C1=O | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | baea70c3ed4e23fb3981a811d0c5d5797285f34961f974af088dbe9c4c60dd14 | 7c33147a6170e63e1fbe1110c4ce069481be57a96b70c4a5a6d7e8253f321bd2 | O=C1c2c([nH]c3ccccc23)CCC1Cn1ccnc1 | C-N(-C)-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[c:6]:[c:7]:[#7;a:8].[C;D1;H3:9]-[c:10]1:[#7;a:11]:[c:12]:[c:13]:[nH;D2;+0:14]:1>>[#7;a:8]:[c:7]:[c:6]-[C:4](=[O;D1;H0:5])-[C:2](-[CH2;D2;+0:1]-[n;H0;D3;+0:14]1:[c:13]:[c:12]:[#7;a:11]:[c:10]:1-[C;D1;H3:9])-[C:3] | 83.1 | [{"value": 83.0, "product": "CC1=NC=CN1CC2CCC3=C(C=4C=CC=CC4N3C)C2=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.1, "product": "CC1=NC=CN1CC2CCC3=C(C=4C=CC=CC4N3C)C2=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | 3-[(Dimethylamino)methyl]-1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one hydrochloride (12 kg, 41 mol) and 2-methylimidazole (20.2 kg, 246 mol, 6 eq.) were suspended in mixture of water (120 L) and DMF (30 L). The reaction mixture was heated to reflux (100–102° C.) and stirred for 5 hours at this temperature. The reacti... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | c1c[nH]cn1 | c1ncc[nH]1 | c1ncc[nH]1.C1[CH]CCc2[nH]c3ccccc3c21 | Other | CN(C)C=O | null | 5 | CN(C)CC1CCc2c(c3ccccc3n2C)C1=O.Cc1ncc[nH]1>CN(C)C=O>Cc1nccn1CC1CCc2c(c3ccccc3n2C)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9b8e8ee433ae4003923410d0cc30e418 | Cc1cc(N)n[nH]1.Clc1nc(Cl)c2ccccc2n1>>Cc1cc(Nc2nc(Cl)nc3ccccc23)n[nH]1 | ClC1=NC2=CC=CC=C2C(=N1)Cl.CC1=CC(=NN1)N>>ClC1=NC2=CC=CC=C2C(=N1)NC1=NNC(=C1)C | [CH3:1][c:2]1[cH:3][c:4]([NH2:5])[n:17][nH:18]1.Cl[c:6]1[n:7][c:8]([Cl:9])[n:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]12>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][c:8]([Cl:9])[n:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]23)[n:17][nH:18]1 | Cc1cc(N)n[nH]1.Clc1nc(Cl)c2ccccc2n1 | Cc1cc(Nc2nc(Cl)nc3ccccc23)n[nH]1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc2c(Nc3cc[nH]n3)ncnc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[NH2;D1;+0:9]-[c:10]1:[#7;a:11]:[#7;a:12]:[c:13]:[c:14]:1>>[c:6]:[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10]2:[#7;a:11]:[#7;a:12]:[c:13]:[c:14]:2):[c:7]:1:[c:8] | null | [] | null | null | 4 | HOUR | To a solution of 2,4-dichloro-quinazoline (3.3 g, 16.6 mmol) in anhydrous ethanol (150 mL) is added 5-methyl-1H-pyrazol-3-yl amine (3.2 g, 32.9 mmol). The mixture is stirred at room temperature for 4 h, and the resulting precipitate is collected by filtration, washed with ethanol, and dried under vacuum to afford (2-ch... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1cn[nH]c1.c1ccc2ncncc2c1 | HCl | C(C)O | null | 4 | Cc1cc(N)n[nH]1.Clc1nc(Cl)c2ccccc2n1>C(C)O>Cc1cc(Nc2nc(Cl)nc3ccccc23)n[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7f2377b602104b21a0f343502473fa9e | Nc1ncccc1C(=O)O.O=C(Cl)c1ccccc1C(F)(F)F>>O=c1oc(-c2ccccc2C(F)(F)F)nc2ncccc12 | FC(C1=C(C(=O)Cl)C=CC=C1)(F)F.NC1=C(C(=O)O)C=CC=N1.O>>FC(C1=C(C=CC=C1)C=1OC(C2=C(N1)N=CC=C2)=O)(F)F | [O:1]=[C:2]([OH:3])[c:21]1[c:16]([NH2:15])[n:17][cH:18][cH:19][cH:20]1.O=[C:4](Cl)[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[C:11]([F:12])([F:13])[F:14]>>[O:1]=[c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[C:11]([F:12])([F:13])[F:14])[n:15][c:16]2[n:17][cH:18][cH:19][cH:20][c:21]12 | Nc1ncccc1C(=O)O.O=C(Cl)c1ccccc1C(F)(F)F | O=c1oc(-c2ccccc2C(F)(F)F)nc2ncccc12 | null | null | N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 2dbd5bdc66d7edcd4601a60f389f4af1f471a8c5eb4f9da081529e62f2da61d0 | bd3eed28c8485f0d5a54b9572c189e3c1ddb148eaacd326cd875cdab2e64ffc8 | O=c1oc(-c2ccccc2)nc2ncccc12 | Cl-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5](-[C:6](-[F;D1;H0:7])(-[F;D1;H0:8])-[F;D1;H0:9]):[c:10].[NH2;D1;+0:11]-[c:12](:[#7;a:13]:[c:14]):[c:15](-[C;H0;D3;+0:16](=[O;D1;H0:17])-[OH;D1;+0:18]):[c:19]>>[F;D1;H0:7]-[C:6](-[F;D1;H0:8])(-[F;D1;H0:9])-[c:5](:[c:10]):[c;H0;D3;+0:2](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:... | 60 | [{"value": 60.0, "product": "FC(C1=C(C=CC=C1)C=1OC(C2=C(N1)N=CC=C2)=O)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.4, "product": "FC(C1=C(C=CC=C1)C=1OC(C2=C(N1)N=CC=C2)=O)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-(Trifluoromethyl)benzoyl chloride (4.2 ml, 29.2 mmol) is added dropwise to a solution of 2-aminonicotinic acid (2.04 g, 14.76 mmol) in 20 ml of pyridine. The reaction mixture is heated at 158 C for 30 min then cooled to room temperature. The reaction is poured into 200 ml of water and an oil forms which solidifies up... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Carboxylic acid.Primary amine | null | c1ccncc1 | c1nc2ncccc2co1 | c1ccccc1.c1nc2ncccc2co1 | HCl | N1=CC=CC=C1 | null | null | Nc1ncccc1C(=O)O.O=C(Cl)c1ccccc1C(F)(F)F>N1=CC=CC=C1>O=c1oc(-c2ccccc2C(F)(F)F)nc2ncccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9eb608089fd14276a75b55fb5c01adb8 | O=c1oc(-c2ccccc2C(F)(F)F)nc2ncccc12.[NH4+]>>NC(=O)c1cccnc1NC(=O)c1ccccc1C(F)(F)F | FC(C1=C(C=CC=C1)C=1OC(C2=C(N1)N=CC=C2)=O)(F)F.[OH-].[NH4+]>>FC(C1=C(C(=O)NC2=C(C(=O)N)C=CC=N2)C=CC=C1)(F)F | [c:2]1(=[O:3])[c:4]2[cH:5][cH:6][cH:7][n:8][c:9]2[n:10][c:11](-[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[C:19]([F:20])([F:21])[F:22])[o:12]1.[NH4+:1]>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][n:8][c:9]1[NH:10][C:11](=[O:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[C:19]([F:20])([F:21])[F:22] | O=c1oc(-c2ccccc2C(F)(F)F)nc2ncccc12.[NH4+] | NC(=O)c1cccnc1NC(=O)c1ccccc1C(F)(F)F | null | null | null | Functional Group Addition | OtherReaction | a6332fb803d8fc078e4dda8e27ec0146c21ce74941638af256736c803ace2b4c | 962c8fe172bf467290cc03d27e3658940d6bee2d517209cffaa45b73a5cca1f8 | O=C(Nc1ccccn1)c1ccccc1 | [F;D1;H0:1]-[C:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[c:5](:[c:6]):[c;H0;D3;+0:7](-[c;H0;D3;+0:8]1:[n;H0;D2;+0:9]:[c:10](:[#7;a:11]:[c:12]):[c:13](:[c:14]):[c;H0;D3;+0:15](=[O;D1;H0:16]):[o;H0;D2;+0:17]:1):[c:18]:[c:19].[NH4+;D0:20]>>[F;D1;H0:1]-[C:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[c:5](:[c:6]):[c;H0;D3;+0:7](-[C;H0;D3;+0:8](=[... | 33 | [{"value": 33.0, "product": "FC(C1=C(C(=O)NC2=C(C(=O)N)C=CC=N2)C=CC=C1)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-(2-Trifluoromethyl-phenyl)-pyrido[2,3-d][1,3]oxazin-4-one (2.51 g) is stirred in 30% ammonium hydroxide (25 ml) at room temperature overnight. The resulting precipitate is filtered and rinsed with water and diethyl ether. The precipitate is dried under vacuum at 50 C overnight to give 2-(2-trifluoromethyl-benzoylamin... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary amide.Secondary amide | c1nc2ncccc2co1 | c1ccncc1 | c1ccncc1.c1ccccc1 | null | null | null | null | O=c1oc(-c2ccccc2C(F)(F)F)nc2ncccc12.[NH4+]>>NC(=O)c1cccnc1NC(=O)c1ccccc1C(F)(F)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ad07cb21f6bc41b9acab444e1cee39e1 | NC(=O)c1cccnc1NC(=O)c1ccccc1C(F)(F)F>>O=c1[nH]c(-c2ccccc2C(F)(F)F)nc2ncccc12 | FC(C1=C(C(=O)NC2=C(C(=O)N)C=CC=N2)C=CC=C1)(F)F.[O-]CC.[K+].S(=O)(=O)(O)[O-].[Na+]>>FC(C1=C(C=CC=C1)C=1NC(C2=C(N1)N=CC=C2)=O)(F)F | O=[C:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[C:11]([F:12])([F:13])[F:14])[NH:15][c:16]1[n:17][cH:18][cH:19][cH:20][c:21]1[C:2](=[O:1])[NH2:3]>>[O:1]=[c:2]1[nH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[C:11]([F:12])([F:13])[F:14])[n:15][c:16]2[n:17][cH:18][cH:19][cH:20][c:21]12 | NC(=O)c1cccnc1NC(=O)c1ccccc1C(F)(F)F | O=c1[nH]c(-c2ccccc2C(F)(F)F)nc2ncccc12 | null | null | O.C(C)O | Aromatic Heterocycle Formation | OtherReaction | e0ec58765b5a7ee3c266c0242348b15638d7e3c71f4e3b76437818b4ad2829ea | 9d5aef0cada2072f52eb60b6996e8c9e376baa92104aa4e87786338b6493e605 | O=c1[nH]c(-c2ccccc2)nc2ncccc12 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[#7;a:4]:[c:5]):[c:6](-[C;H0;D3;+0:7](-[NH2;D1;+0:8])=[O;D1;H0:9]):[c:10])-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14](-[C:15](-[F;D1;H0:16])(-[F;D1;H0:17])-[F;D1;H0:18]):[c:19]>>[F;D1;H0:16]-[C:15](-[F;D1;H0:17])(-[F;D1;H0:18])-[c:14](:[c:19]):[c;H0;D3;+0:11](-[c;H0;D3;+0:1]1:[n;H0;D2;... | null | [] | null | null | null | null | 2-(2-Trifluoromethyl-benzoylamino)-nicotinamide (800 mg, 2.6 mmol) is dissolved in 10 ml of ethanol. Potassium ethoxide (435 mg, 5.2 mmol) is added to the solution which is heated to reflux for 16 h. The reaction mixture is evaporated in vacuo to afford a gummy residue that is dissolved in water and acidified with 10% ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Secondary amide | null | c1ccncc1 | c1ncc2cccnc2n1 | c1ccccc1.c1ncc2cccnc2n1 | HO- | O.C(C)O | null | null | NC(=O)c1cccnc1NC(=O)c1ccccc1C(F)(F)F>O.C(C)O>O=c1[nH]c(-c2ccccc2C(F)(F)F)nc2ncccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c773c44bb45845f98c56eecf02d8c1d4 | Cc1cc(Nc2nc(-c3ccc(Br)cc3)nc3ccccc23)[nH]n1.OB(O)c1ccccc1>>Cc1cc(Nc2nc(-c3ccc(-c4ccccc4)cc3)nc3ccccc23)[nH]n1 | BrC1=CC=C(C=C1)C1=NC2=CC=CC=C2C(=N1)NC=1NN=C(C1)C.C1(=CC=CC=C1)B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>C1(=CC=C(C=C1)C1=NC2=CC=CC=C2C(=N1)NC=1NN=C(C1)C)C1=CC=CC=C1 | Br[c:12]1[cH:11][cH:10][c:9](-[c:8]2[n:7][c:6]([NH:5][c:4]3[cH:3][c:2]([CH3:1])[n:29][nH:28]3)[c:27]3[c:22]([n:21]2)[cH:23][cH:24][cH:25][cH:26]3)[cH:20][cH:19]1.OB(O)[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][c:8](-[c:9]3[cH:10][cH:11][c:12](-[c:13]4[cH:14][cH:15][cH:16][cH... | Cc1cc(Nc2nc(-c3ccc(Br)cc3)nc3ccccc23)[nH]n1.OB(O)c1ccccc1 | Cc1cc(Nc2nc(-c3ccc(-c4ccccc4)cc3)nc3ccccc23)[nH]n1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | C1CCOC1.O | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc(-c3nc(Nc4ccn[nH]4)c4ccccc4n3)cc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 51.4 | [{"value": 51.0, "product": "C1(=CC=C(C=C1)C1=NC2=CC=CC=C2C(=N1)NC=1NN=C(C1)C)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.4, "product": "C1(=CC=C(C=C1)C1=NC2=CC=CC=C2C(=N1)NC=1NN=C(C1)C)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | Method H(i). To a mixture of [2-(4-bromo-phenyl)-quinazolin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine (196 mg, 0.51 mmol) and phenylboronic acid (75 mg, 0.62 mmol) in THF/water (1/1, 4 mL) is added Na2CO3 (219 mg, 2.06 mmol), triphenylphosphine (9 mg, 1/15 mol %) and palladium acetate (1 mg, 1/135 mol %). The mixture is h... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1cn[nH]c1.c1ccccc1.c1ccccc1.c1ccc2ncncc2c1 | HBr.B | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1CCOC1.O | 80 | null | Cc1cc(Nc2nc(-c3ccc(Br)cc3)nc3ccccc23)[nH]n1.OB(O)c1ccccc1>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1CCOC1.O>Cc1cc(Nc2nc(-c3ccc(-c4ccccc4)cc3)nc3ccccc23)[nH]n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4b1bcbd19517494f9bf9a403dd2b9886 | CC1CCN(c2ccnc(Cl)n2)CC1.Cc1cc(N)[nH]n1>>Cc1cc(Nc2nccc(N3CCC(C)CC3)n2)[nH]n1 | NC=1NN=C(C1)C.ClC1=NC=CC(=N1)N1CCC(CC1)C.C([O-])([O-])=O.[K+].[K+]>>CC1CCN(CC1)C1=NC(=NC=C1)NC=1NN=C(C1)C | Cl[c:6]1[n:7][cH:8][cH:9][c:10]([N:11]2[CH2:12][CH2:13][CH:14]([CH3:15])[CH2:16][CH2:17]2)[n:18]1.[CH3:1][c:2]1[cH:3][c:4]([NH2:5])[nH:19][n:20]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][cH:8][cH:9][c:10]([N:11]3[CH2:12][CH2:13][CH:14]([CH3:15])[CH2:16][CH2:17]3)[n:18]2)[nH:19][n:20]1 | CC1CCN(c2ccnc(Cl)n2)CC1.Cc1cc(N)[nH]n1 | Cc1cc(Nc2nccc(N3CCC(C)CC3)n2)[nH]n1 | null | null | C(CCC)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2nccc(N3CCCCC3)n2)[nH]n1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7]1:[#7;a:8]:[#7;a:9]:[c:10]:[c:11]:1>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7]1:[#7;a:8]:[#7;a:9]:[c:10]:[c:11]:1):[#7;a:4]:[c:5] | 50 | [{"value": 50.0, "product": "CC1CCN(CC1)C1=NC(=NC=C1)NC=1NN=C(C1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 2-chloro-4-(4-methylpiperidin-1-yl)-pyrimidine (prepared using a procedure similar to the one reported in Eur. J. Med. Chem., 26(7) 729(1991))(222 mg, 1.05 mmol) in BuOH (5 mL) was added 3-amino-5-methyl-2H-pyrazole (305 mg, 3.15 mmol) and the reaction mixture was then heated under reflux overnight. Th... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cn[nH]c1.c1cncnc1.C1CC[NH]CC1 | HCl | C(CCC)O | null | 2 | CC1CCN(c2ccnc(Cl)n2)CC1.Cc1cc(N)[nH]n1>C(CCC)O>Cc1cc(Nc2nccc(N3CCC(C)CC3)n2)[nH]n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d802451e51154590a52dc727551dba05 | Clc1ccccc1-c1nc(Cl)c2cccnc2n1.Nc1n[nH]c2c(F)cccc12>>Fc1cccc2c(Nc3nc(-c4ccccc4Cl)nc4ncccc34)n[nH]c12 | ClC=1C2=C(N=C(N1)C1=C(C=CC=C1)Cl)N=CC=C2.FC=1C=CC=C2C(=NNC12)N>>ClC1=C(C=CC=C1)C=1N=C(C2=C(N1)N=CC=C2)NC2=NNC1=C(C=CC=C21)F | Cl[c:9]1[n:10][c:11](-[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[Cl:18])[n:19][c:20]2[n:21][cH:22][cH:23][cH:24][c:25]12.[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]([NH2:8])[n:26][nH:27][c:28]12>>[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]([NH:8][c:9]3[n:10][c:11](-[c:12]4[cH:13][cH:14][cH:15][cH:16][c:17]4[Cl:18])[n:19][c:2... | Clc1ccccc1-c1nc(Cl)c2cccnc2n1.Nc1n[nH]c2c(F)cccc12 | Fc1cccc2c(Nc3nc(-c4ccccc4Cl)nc4ncccc34)n[nH]c12 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 95363dd4f7eaf5ca3b2b81ca3d4d6901dabfa76417ca700d29bf339c0c5e8fb0 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(-c2nc(Nc3n[nH]c4ccccc34)c3cccnc3n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[#7;a:6]:[c:7]):[c:8]:1:[c:9].[NH2;D1;+0:10]-[c:11]1:[#7;a:12]:[#7;a:13]:[c:14]:[c:15]:1>>[c:7]:[#7;a:6]:[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11]2:[#7;a:12]:[#7;a:13]:[c:14]:[c:15]:2):[c:8]:1:[c:9] | 46 | [{"value": 46.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Prepared from 4-Chloro-2-(2-chloro-phenyl)-pyrido[2,3-d]pyrimidine (100 mg, 0.36 mmol) and 7-Fluoro-1H-indazol-3-ylamine (108 mg, 0.72 mmol). Purification by preparative HPLC afforded the title compound as a yellow, di-TFA salt (93 mg, 46% yield). HPLC-Method A, Rt 3.04 min; 1H NMR (DMSO, 500 MHz): δ 13.67 (1H, s), 11.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1.c1ccc2n[nH]cc2c1 | HCl | null | null | null | Clc1ccccc1-c1nc(Cl)c2cccnc2n1.Nc1n[nH]c2c(F)cccc12>>Fc1cccc2c(Nc3nc(-c4ccccc4Cl)nc4ncccc34)n[nH]c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5c74c9c08b834259ac387d996b46fb8b | Clc1ccccc1-c1nc(Cl)c2ccncc2n1.Nc1n[nH]c2ccccc12>>Clc1ccccc1-c1nc(Nc2n[nH]c3ccccc23)c2ccncc2n1 | ClC=1C2=C(N=C(N1)C1=C(C=CC=C1)Cl)C=NC=C2.N1N=C(C2=CC=CC=C12)N>>ClC1=C(C=CC=C1)C=1N=C(C2=C(N1)C=NC=C2)NC2=NNC1=CC=CC=C21 | Cl[c:10]1[n:9][c:8](-[c:7]2[c:2]([Cl:1])[cH:3][cH:4][cH:5][cH:6]2)[n:27][c:26]2[c:21]1[cH:22][cH:23][n:24][cH:25]2.[NH2:11][c:12]1[n:13][nH:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]12>>[Cl:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1-[c:8]1[n:9][c:10]([NH:11][c:12]2[n:13][nH:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]23)... | Clc1ccccc1-c1nc(Cl)c2ccncc2n1.Nc1n[nH]c2ccccc12 | Clc1ccccc1-c1nc(Nc2n[nH]c3ccccc23)c2ccncc2n1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | d7e80981ec4355d1692da3210ded123ee4151f1f202c481ca7dd6b10037b54ac | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(-c2nc(Nc3n[nH]c4ccccc34)c3ccncc3n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[#7;a:7]:[c:8]:[c:9]:[c:10]:2:1.[NH2;D1;+0:11]-[c:12]1:[#7;a:13]:[#7;a:14]:[c:15]:[c:16]:1>>[#7;a:13]1:[#7;a:14]:[c:15]:[c:16]:[c:12]:1-[NH;D2;+0:11]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[#7;a:7]:[c:8]:[c:9]:[c:10]:2:1 | 33 | [{"value": 33.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Prepared from 4-Chloro-2-(2-chloro-phenyl)-pyrido[3,4-d]pyrimidine (100 mg, 0.36 mmol) and 1H-indazol-3-ylamine (88 mg, 0.66 mmol). Purification by preparative HPLC afforded the title compound as a yellow, di-TFA salt (72 mg, 33% yield). HPLC-Method A, Rt 3.21 min; 1H NMR (DMSO, 500 MHz): δ 12.95 (1H, s), 10.90 (1H, bs... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cc2cncnc2cn1 | c1cc2cncnc2cn1 | c1ccccc1.c1ccc2n[nH]cc2c1.c1cc2cncnc2cn1 | HCl | null | null | null | Clc1ccccc1-c1nc(Cl)c2ccncc2n1.Nc1n[nH]c2ccccc12>>Clc1ccccc1-c1nc(Nc2n[nH]c3ccccc23)c2ccncc2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b134537bc4c643eabbfe65a48bec7bec | COc1cccc2c(=O)[nH]c(-c3ccccc3C(F)(F)F)nc12.O=P(Cl)(Cl)Cl>>COc1cccc2c(Cl)nc(-c3ccccc3C(F)(F)F)nc12 | COC=1C=CC=C2C(NC(=NC12)C1=C(C=CC=C1)C(F)(F)F)=O.Cl.C(C)N(CC)CC.O=P(Cl)(Cl)Cl>>ClC1=NC(=NC2=C(C=CC=C12)OC)C1=C(C=CC=C1)C(F)(F)F | O=[c:8]1[c:7]2[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[c:23]2[n:22][c:11](-[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[C:18]([F:19])([F:20])[F:21])[nH:10]1.O=P(Cl)(Cl)[Cl:9]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]([Cl:9])[n:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[C:18]([F:19])([F:20])[F:21])[n:22][c:... | COc1cccc2c(=O)[nH]c(-c3ccccc3C(F)(F)F)nc12.O=P(Cl)(Cl)Cl | COc1cccc2c(Cl)nc(-c3ccccc3C(F)(F)F)nc12 | null | null | null | Functional Group Interconversion | OtherReaction | 6f0285013e3068fc43dc9b72286fa243f9715611831aa1bdc0252411e07fdbf3 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc(-c2ncc3ccccc3n2)cc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4](-[c:5]):[#7;a:6]:[c:7](:[c:8]):[c:9]:1:[c:10]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c:4](-[c:5]):[#7;a:6]:[c:7](:[c:8]):[c:9]:1:[c:10] | 89 | [{"value": 89.0, "product": "ClC1=NC(=NC2=C(C=CC=C12)OC)C1=C(C=CC=C1)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Prepared from 8-methoxy-2-(2-trifluoromethyl-phenyl)-3H-quinazolin-4-one (1.0 g, 3.12 mmol), triethylamine hydrochloride (472 mg, 3.43 mmol), and POCl3. Purification by flash chromatography afforded a white solid (89% yield). HPLC-Method A, Rt 4.10 min, (98%), MS (m/z) 258.08 (M+H).
Conditions: See reaction.notes.proce... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ncc2ccccc2n1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccccc1 | HCl | null | null | null | COc1cccc2c(=O)[nH]c(-c3ccccc3C(F)(F)F)nc12.O=P(Cl)(Cl)Cl>>COc1cccc2c(Cl)nc(-c3ccccc3C(F)(F)F)nc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3832c318a13546e6a68603f494b26d32 | Cc1cc(Nc2nc(-c3ccc(Br)cc3)nc3ccccc23)[nH]n1.OB(O)c1ccccc1>>Cc1cc(Nc2nc(-c3ccc(-c4ccccc4)cc3)nc3ccccc23)[nH]n1 | BrC1=CC=C(C=C1)C1=NC2=CC=CC=C2C(=N1)NC=1NN=C(C1)C.C1(=CC=CC=C1)B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>C1(=CC=C(C=C1)C1=NC2=CC=CC=C2C(=N1)NC=1NN=C(C1)C)C1=CC=CC=C1 | Br[c:12]1[cH:11][cH:10][c:9](-[c:8]2[n:7][c:6]([NH:5][c:4]3[cH:3][c:2]([CH3:1])[n:29][nH:28]3)[c:27]3[c:22]([n:21]2)[cH:23][cH:24][cH:25][cH:26]3)[cH:20][cH:19]1.OB(O)[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][c:8](-[c:9]3[cH:10][cH:11][c:12](-[c:13]4[cH:14][cH:15][cH:16][cH... | Cc1cc(Nc2nc(-c3ccc(Br)cc3)nc3ccccc23)[nH]n1.OB(O)c1ccccc1 | Cc1cc(Nc2nc(-c3ccc(-c4ccccc4)cc3)nc3ccccc23)[nH]n1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | C1CCOC1.O | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc(-c3nc(Nc4ccn[nH]4)c4ccccc4n3)cc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 51.4 | [{"value": 51.0, "product": "C1(=CC=C(C=C1)C1=NC2=CC=CC=C2C(=N1)NC=1NN=C(C1)C)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.4, "product": "C1(=CC=C(C=C1)C1=NC2=CC=CC=C2C(=N1)NC=1NN=C(C1)C)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | To a mixture of [2-(4-bromo-phenyl)-quinazolin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine (III-34) (196 mg, 0.51 mmol) and phenylboronic acid (75 mg, 0.62 mmol) in THF:water (1:1, 4 mL) was added Na2CO3 (219 mg, 2.06 mmol), triphenylphosphine (9 mg, 1/15 mol %) and palladium acetate (1 mg, 1:135 mol %). The resulting mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1cn[nH]c1.c1ccccc1.c1ccccc1.c1ccc2ncncc2c1 | HBr.B | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1CCOC1.O | 80 | null | Cc1cc(Nc2nc(-c3ccc(Br)cc3)nc3ccccc23)[nH]n1.OB(O)c1ccccc1>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1CCOC1.O>Cc1cc(Nc2nc(-c3ccc(-c4ccccc4)cc3)nc3ccccc23)[nH]n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-033fb67cfd234c2db5036f5938eff4a9 | Cc1cc(N)n[nH]1.Clc1nc(Cl)c2ccccc2n1>>Cc1cc(Nc2nc(Cl)nc3ccccc23)n[nH]1 | ClC1=NC2=CC=CC=C2C(=N1)Cl.CC1=CC(=NN1)N>>ClC1=NC2=CC=CC=C2C(=N1)NC1=NNC(=C1)C | [CH3:1][c:2]1[cH:3][c:4]([NH2:5])[n:17][nH:18]1.Cl[c:6]1[n:7][c:8]([Cl:9])[n:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]12>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][c:8]([Cl:9])[n:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]23)[n:17][nH:18]1 | Cc1cc(N)n[nH]1.Clc1nc(Cl)c2ccccc2n1 | Cc1cc(Nc2nc(Cl)nc3ccccc23)n[nH]1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc2c(Nc3cc[nH]n3)ncnc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[NH2;D1;+0:9]-[c:10]1:[#7;a:11]:[#7;a:12]:[c:13]:[c:14]:1>>[c:6]:[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10]2:[#7;a:11]:[#7;a:12]:[c:13]:[c:14]:2):[c:7]:1:[c:8] | 93 | [{"value": 93.0, "product": "ClC1=NC2=CC=CC=C2C(=N1)NC1=NNC(=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.8, "product": "ClC1=NC2=CC=CC=C2C(=N1)NC1=NNC(=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A suspension of 1H-quinazoline-2,4-dione (10.0 g, 61.7 mmol) in POCl3 (60 mL, 644 mmol) and N,N-dimethylaniline (8 mL, 63.1 mmol) was heated under reflux for 2 h. The excess POCl3 was removed in vacuo, the residue poured into ice, and the resulting precipitate collected by filtration. The crude solid product 2,4-dichlo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1cn[nH]c1.c1ccc2ncncc2c1 | HCl | C(C)O | null | 4 | Cc1cc(N)n[nH]1.Clc1nc(Cl)c2ccccc2n1>C(C)O>Cc1cc(Nc2nc(Cl)nc3ccccc23)n[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d722e543915a4c2da4ccb700d9ffdc57 | Cc1cc(Nc2nc(Cl)nc3ccccc23)n[nH]1.Cc1cccc(B(O)O)c1>>Cc1cccc(-c2nc(Nc3cc(C)n[nH]3)c3ccccc3n2)c1 | ClC1=NC2=CC=CC=C2C(=N1)NC1=NNC(=C1)C.C1(=CC(=CC=C1)B(O)O)C.C(=O)([O-])[O-].[Na+].[Na+].C(C)(C)(C)P(C(C)(C)C)C(C)(C)C>>CC=1C=C(C=CC1)C1=NC2=CC=CC=C2C(=N1)NC=1NN=C(C1)C | Cl[c:7]1[n:8][c:9]([NH:10][c:11]2[cH:12][c:13]([CH3:14])[nH:15][n:16]2)[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2[n:23]1.OB(O)[c:6]1[cH:5][cH:4][cH:3][c:2]([CH3:1])[cH:24]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[n:8][c:9]([NH:10][c:11]3[cH:12][c:13]([CH3:14])[n:15][nH:16]3)[c:17]3[cH:18][cH:19][cH:20][cH:21][c:2... | Cc1cc(Nc2nc(Cl)nc3ccccc23)n[nH]1.Cc1cccc(B(O)O)c1 | Cc1cccc(-c2nc(Nc3cc(C)n[nH]3)c3ccccc3n2)c1 | 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.CN(C)C=O | C-C Coupling | OtherReaction | e11757e18e26f9674938ea5830aa7b8b9ca2f4d52a63db4dc23ddf9cfe7f2462 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2nc(Nc3ccn[nH]3)c3ccccc3n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]-[#7:6]-[c:7]1:[c:8]:[c:9](-[C;D1;H3:10]):[nH;D2;+0:11]:[n;H0;D2;+0:12]:1.O-B(-O)-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16]:[c:17]>>[C;D1;H3:10]-[c:9]1:[c:8]:[c:7](-[#7:6]-[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16]:[c:17]):[#7;a:2]:[c:3]):[nH;D2;+... | 101.8 | [{"value": 75.0, "product": "CC=1C=C(C=CC1)C1=NC2=CC=CC=C2C(=N1)NC=1NN=C(C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 101.8, "product": "CC=1C=C(C=CC1)C1=NC2=CC=CC=C2C(=N1)NC=1NN=C(C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A suspension of 1H-quinazoline-2,4-dione (10.0 g, 61.7 mmol) in POCl3 (60 mL, 644 mmol) and N,N-dimethylaniline (8 mL, 63.1 mmol) was heated under reflux for 2 h. The excess POCl3 was removed in vacuo, the residue poured into ice, and the resulting precipitate collected by filtration. The crude solid product 2,4-dichlo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2ncncc2c1.c1ccccc1 | c1ccccc1.c1ccc2ncncc2c1 | c1ccccc1.c1cn[nH]c1.c1ccc2ncncc2c1 | HCl.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.CN(C)C=O | 80 | null | Cc1cc(Nc2nc(Cl)nc3ccccc23)n[nH]1.Cc1cccc(B(O)O)c1>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.CN(C)C=O>Cc1cccc(-c2nc(Nc3cc(C)n[nH]3)c3ccccc3n2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2c4aae8e65dc4453b9a093bb758a2995 | COC(=O)c1cc(Nc2nc(-c3ccccc3)nc3ccccc23)[nH]n1>>O=C(O)c1cc(Nc2nc(-c3ccccc3)nc3ccccc23)[nH]n1 | COC(=O)C=1C=C(NN1)NC1=NC(=NC2=CC=CC=C12)C1=CC=CC=C1.[OH-].[Na+].Cl>>C(=O)(O)C=1C=C(NN1)NC1=NC(=NC2=CC=CC=C12)C1=CC=CC=C1 | C[O:3][C:2](=[O:1])[c:4]1[cH:5][c:6]([NH:7][c:8]2[n:9][c:10](-[c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[n:17][c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]23)[nH:24][n:25]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([NH:7][c:8]2[n:9][c:10](-[c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[n:17][c:18]3[cH:19][cH:20][cH:21][cH:22][... | COC(=O)c1cc(Nc2nc(-c3ccccc3)nc3ccccc23)[nH]n1 | O=C(O)c1cc(Nc2nc(-c3ccccc3)nc3ccccc23)[nH]n1 | null | null | null | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2nc(Nc3ccn[nH]3)c3ccccc3n2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#7;a:5]:[#7;a:6]>>[#7;a:6]:[#7;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 94.2 | [{"value": 94.0, "product": "C(=O)(O)C=1C=C(NN1)NC1=NC(=NC2=CC=CC=C12)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.2, "product": "C(=O)(O)C=1C=C(NN1)NC1=NC(=NC2=CC=CC=C12)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 5 | HOUR | (5-Methoxycarbonyl-2H-pyrazol-3-yl)-(2-phenyl-quinazolin-4-yl)-amine (III-73) (345 mg, 1 mmole in THF, 6 mL) was treated with NaOH (1M, 4.0 mL), stirred at 50° C. for 5 hours, cooled to room temperature, and neutralised with 1M HCl. The mixture was concentrated in vacuo to remove THF then diluted with water and the res... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cn[nH]c1.c1ccccc1.c1ccc2ncncc2c1 | Other | null | 50 | 5 | COC(=O)c1cc(Nc2nc(-c3ccccc3)nc3ccccc23)[nH]n1>>O=C(O)c1cc(Nc2nc(-c3ccccc3)nc3ccccc23)[nH]n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8f6d4d2b6d544574b77ff5bfc8e3f093 | COC(=O)c1cc(Nc2nc(-c3ccccc3)nc3ccccc23)[nH]n1>>OCc1cc(Nc2nc(-c3ccccc3)nc3ccccc23)[nH]n1 | C(O)([O-])=O.[Na+].Cl.COC(=O)C=1C=C(NN1)NC1=NC(=NC2=CC=CC=C12)C1=CC=CC=C1.[BH4-].[Li+]>>OCC=1C=C(NN1)NC1=NC(=NC2=CC=CC=C12)C1=CC=CC=C1 | CO[C:2](=[O:1])[c:3]1[cH:4][c:5]([NH:6][c:7]2[n:8][c:9](-[c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[n:16][c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]23)[nH:23][n:24]1>>[OH:1][CH2:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[n:8][c:9](-[c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[n:16][c:17]3[cH:18][cH:19][cH:20][cH:21][c:22]23)[nH:... | COC(=O)c1cc(Nc2nc(-c3ccccc3)nc3ccccc23)[nH]n1 | OCc1cc(Nc2nc(-c3ccccc3)nc3ccccc23)[nH]n1 | null | null | C1CCOC1.C(C)(=O)OCC | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(-c2nc(Nc3ccn[nH]3)c3ccccc3n2)cc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3]1:[#7;a:4]:[#7;a:5]:[c:6]:[c:7]:1>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3]1:[#7;a:4]:[#7;a:5]:[c:6]:[c:7]:1 | null | [] | null | null | null | null | A solution of (5-Methoxycarbonyl-2H-pyrazol-3-yl)-(2-phenyl-quinazolin-4-yl)-amine (III-73) (345 mg, 1 mmol) in anhydrous THF (10 mL) was treated with lithium borohydride (125 mg, 5.75 mmol) at 65° C. for 5 hours. The mixture was cooled to room temperature then combined with 2M HCl and ethyl acetate. Solid sodium hydro... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1cn[nH]c1.c1ccccc1.c1ccc2ncncc2c1 | Other | C1CCOC1.C(C)(=O)OCC | null | null | COC(=O)c1cc(Nc2nc(-c3ccccc3)nc3ccccc23)[nH]n1>C1CCOC1.C(C)(=O)OCC>OCc1cc(Nc2nc(-c3ccccc3)nc3ccccc23)[nH]n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c3de370c8f6940959561675cc6d590bf | CC(C)(C)OC(=O)NCCCc1cc(Nc2nc(-c3ccccc3)nc3ccccc23)[nH]n1>>NCCCc1cc(Nc2nc(-c3ccccc3)nc3ccccc23)[nH]n1 | C(C)(C)(C)OC(=O)NCCCC=1C=C(NN1)NC1=NC(=NC2=CC=CC=C12)C1=CC=CC=C1.C(=O)(C(F)(F)F)O>>NCCCC=1C=C(NN1)NC1=NC(=NC2=CC=CC=C12)C1=CC=CC=C1 | CC(C)(C)OC(=O)[NH:1][CH2:2][CH2:3][CH2:4][c:5]1[cH:6][c:7]([NH:8][c:9]2[n:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[n:18][c:19]3[cH:20][cH:21][cH:22][cH:23][c:24]23)[nH:25][n:26]1>>[NH2:1][CH2:2][CH2:3][CH2:4][c:5]1[cH:6][c:7]([NH:8][c:9]2[n:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[n:18][c:... | CC(C)(C)OC(=O)NCCCc1cc(Nc2nc(-c3ccccc3)nc3ccccc23)[nH]n1 | NCCCc1cc(Nc2nc(-c3ccccc3)nc3ccccc23)[nH]n1 | null | null | ClCCl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc(-c2nc(Nc3ccn[nH]3)c3ccccc3n2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | 63.3 | [{"value": 63.0, "product": "NCCCC=1C=C(NN1)NC1=NC(=NC2=CC=CC=C12)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.3, "product": "NCCCC=1C=C(NN1)NC1=NC(=NC2=CC=CC=C12)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of [5-(3-tert-butoxycarbonylaminoprop-1-yl)-2H-pyrazol-3-yl]-(2-phenyl-quinazolin-4-yl)-amine (III-80) (250 mg, 0.56 mmol), in dichloromethane (3 mL) at 0° C. was treated with TFA (2 mL). The mixture was warmed to room temperature then concentrated in vacuo. The residue was triturated and concentrated from d... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1cn[nH]c1.c1ccccc1.c1ccc2ncncc2c1 | HO- | ClCCl | null | null | CC(C)(C)OC(=O)NCCCc1cc(Nc2nc(-c3ccccc3)nc3ccccc23)[nH]n1>ClCCl>NCCCc1cc(Nc2nc(-c3ccccc3)nc3ccccc23)[nH]n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c7a7c6e1b27b425197b7322315a00e4d | CC1CCNCC1.Clc1nc(Nc2cc(C3CC3)[nH]n2)c2ccccc2n1>>CC1CCN(c2nc(Nc3cc(C4CC4)n[nH]3)c3ccccc3n2)CC1 | C([O-])([O-])=O.[K+].[K+].C1(CC1)C1=CC(=NN1)NC1=NC(=NC2=CC=CC=C12)Cl.CC1CCNCC1>>C1(CC1)C=1C=C(NN1)NC1=NC(=NC2=CC=CC=C12)N1CCC(CC1)C | [CH3:1][CH:2]1[CH2:3][CH2:4][NH:5][CH2:25][CH2:26]1.Cl[c:6]1[n:7][c:8]([NH:9][c:10]2[cH:11][c:12]([CH:13]3[CH2:14][CH2:15]3)[nH:16][n:17]2)[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2[n:24]1>>[CH3:1][CH:2]1[CH2:3][CH2:4][N:5]([c:6]2[n:7][c:8]([NH:9][c:10]3[cH:11][c:12]([CH:13]4[CH2:14][CH2:15]4)[n:16][nH:17]3)[c:18]3[cH:... | CC1CCNCC1.Clc1nc(Nc2cc(C3CC3)[nH]n2)c2ccccc2n1 | CC1CCN(c2nc(Nc3cc(C4CC4)n[nH]3)c3ccccc3n2)CC1 | null | null | C(C)(C)(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 2d4d37ff2a13382a8cb5903cac2202616d5c68a02b154ba28452de35ced25a57 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc2c(Nc3cc(C4CC4)n[nH]3)nc(N3CCCCC3)nc2c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]-[#7:6]-[c:7]1:[c:8]:[c:9](-[C:10]):[nH;D2;+0:11]:[n;H0;D2;+0:12]:1.[C:13]-[C:14]-[NH;D2;+0:15]-[C:16]-[C:17]>>[C:10]-[c:9]1:[c:8]:[c:7](-[#7:6]-[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[N;H0;D3;+0:15](-[C:14]-[C:13])-[C:16]-[C:17]):[#7;a:2]:[c:3]):[nH;D2;+0:12]:[n;H0;D2;+0:11]:1 | 86.1 | [{"value": 85.0, "product": "C1(CC1)C=1C=C(NN1)NC1=NC(=NC2=CC=CC=C12)N1CCC(CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.1, "product": "C1(CC1)C=1C=C(NN1)NC1=NC(=NC2=CC=CC=C12)N1CCC(CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of (5-cyclopropyl-1H-pyrazol-3-yl)-(2-chloro-quinazolin-4-yl)-amine (118 mg, 0.41 mmol) in tert-butanol (3.0 mL) was added 4-methylpiperidine (0.49 mL, 4.1 mmol) and the reaction mixture heated at reflux overnight. The reaction mixture was concentrated in vacuo and the residue dissolved in a mixture EtOH:... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNCC1.c1ccc2ncncc2c1 | C1CC[NH]CC1.c1ccc2ncncc2c1 | C1CC[NH]CC1.c1cn[nH]c1.C1CC1.c1ccc2ncncc2c1 | HCl | C(C)(C)(C)O | null | 2 | CC1CCNCC1.Clc1nc(Nc2cc(C3CC3)[nH]n2)c2ccccc2n1>C(C)(C)(C)O>CC1CCN(c2nc(Nc3cc(C4CC4)n[nH]3)c3ccccc3n2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-112cf652bf9f4a6688b28ac649f63860 | Cc1cc(N)n[nH]1.Clc1cc(Cl)nc(-c2ccccc2)n1>>Cc1cc(Nc2cc(Cl)nc(-c3ccccc3)n2)[nH]n1 | C=1C=CC(=CC1)C=2N=C(C=C(N2)Cl)Cl.NC1=NNC(=C1)C.C(C)(C)N(C(C)C)CC.[I-].[Na+]>>ClC1=CC(=NC(=N1)C1=CC=CC=C1)NC=1NN=C(C1)C | [CH3:1][c:2]1[cH:3][c:4]([NH2:5])[n:19][nH:20]1.Cl[c:6]1[cH:7][c:8]([Cl:9])[n:10][c:11](-[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[n:18]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[cH:7][c:8]([Cl:9])[n:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[n:18]2)[nH:19][n:20]1 | Cc1cc(N)n[nH]1.Clc1cc(Cl)nc(-c2ccccc2)n1 | Cc1cc(Nc2cc(Cl)nc(-c3ccccc3)n2)[nH]n1 | null | null | C(CCC)O | Heteroatom Alkylation and Arylation | OtherReaction | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(-c2nccc(Nc3ccn[nH]3)n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](-[Cl;D1;H0:7]):[c:8]:1.[C;D1;H3:9]-[c:10]1:[c:11]:[c:12](-[NH2;D1;+0:13]):[n;H0;D2;+0:14]:[nH;D2;+0:15]:1>>[C;D1;H3:9]-[c:10]1:[c:11]:[c:12](-[NH;D2;+0:13]-[c;H0;D3;+0:1]2:[#7;a:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](-[Cl;D1;H0:7]):[c:8]:2):[nH;D2;+0:14]:[n;H0;D2;+0:15]... | 29.4 | [{"value": 29.0, "product": "ClC1=CC(=NC(=N1)C1=CC=CC=C1)NC=1NN=C(C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 29.4, "product": "ClC1=CC(=NC(=N1)C1=CC=CC=C1)NC=1NN=C(C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 117 | CELSIUS | null | null | A suspension of Fenclorim (4,6-dichloro-2-phenylpyrimidine)(0.1 g, 0.44 mmol), 3-amino-5-methylpyrazole (0.045 g, 0.47 mmol), N,N-diisopropylethylamine (0.08 ml, 0.47 mmol) and sodium iodide (0.067 g, 0.44 mmol) in n-butanol (5 ml) were heated at 117° C. for 18 hours. The solvent was removed in vacuo and the crude prod... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cn[nH]c1.c1cncnc1.c1ccccc1 | HCl | C(CCC)O | 117 | null | Cc1cc(N)n[nH]1.Clc1cc(Cl)nc(-c2ccccc2)n1>C(CCC)O>Cc1cc(Nc2cc(Cl)nc(-c3ccccc3)n2)[nH]n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-74bd5f909fdd45cab060be5e2f1707cd | Cc1cc(N)n[nH]1.Clc1nc(-c2ccccc2)nc2ncccc12>>Cc1cc(Nc2nc(-c3ccccc3)nc3ncccc23)[nH]n1 | ClC=1C2=C(N=C(N1)C1=CC=CC=C1)N=CC=C2.NC1=NNC(=C1)C>>CC=1C=C(NN1)NC=1C2=C(N=C(N1)C1=CC=CC=C1)N=CC=C2 | [CH3:1][c:2]1[cH:3][c:4]([NH2:5])[n:22][nH:23]1.Cl[c:6]1[n:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[n:15][c:16]2[n:17][cH:18][cH:19][cH:20][c:21]12>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][c:8](-[c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[n:15][c:16]3[n:17][cH:18][cH:19][cH:20][c:21]23)[nH:22][n:23]1 | Cc1cc(N)n[nH]1.Clc1nc(-c2ccccc2)nc2ncccc12 | Cc1cc(Nc2nc(-c3ccccc3)nc3ncccc23)[nH]n1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 95363dd4f7eaf5ca3b2b81ca3d4d6901dabfa76417ca700d29bf339c0c5e8fb0 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(-c2nc(Nc3ccn[nH]3)c3cccnc3n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[#7;a:6]:[c:7]):[c:8]:1:[c:9].[C;D1;H3:10]-[c:11]1:[c:12]:[c:13](-[NH2;D1;+0:14]):[n;H0;D2;+0:15]:[nH;D2;+0:16]:1>>[C;D1;H3:10]-[c:11]1:[c:12]:[c:13](-[NH;D2;+0:14]-[c;H0;D3;+0:1]2:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[#7;a:6]:[c:7]):[c:8]:2:[c:9]):[nH;D2;+0:15]:[n;H0;D2;+0:1... | 50.7 | [{"value": 50.0, "product": "CC=1C=C(NN1)NC=1C2=C(N=C(N1)C1=CC=CC=C1)N=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.7, "product": "CC=1C=C(NN1)NC=1C2=C(N=C(N1)C1=CC=CC=C1)N=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | null | null | To a solution of 4-chloro-2-phenyl-pyrido[2,3-d]pyrimidine (J. Pharm. Belg., 29, 1974, 145–148) (109 mg, 0.45 mmol) in THF (15 mL) was added 3-amino-5-methyl pyrazole (48 mg, 0.5 mmol) and the resulting mixture heated at 65° C. overnight. The mixture was cooled to room temperature and the resulting suspension was filte... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1cn[nH]c1.c1ccccc1.c1cnc2ncncc2c1 | HCl | C1CCOC1 | 65 | null | Cc1cc(N)n[nH]1.Clc1nc(-c2ccccc2)nc2ncccc12>C1CCOC1>Cc1cc(Nc2nc(-c3ccccc3)nc3ncccc23)[nH]n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1df214bd9a1d4ad4b0661807b2b55fd6 | Cc1cc(N)n[nH]1.ClC1=NC2(Cl)N=CN=C2C=N1>>Cc1cc(NC23N=CN=C2C=NC(Cl)=N3)n[nH]1 | ClC=1N=CC2=NC=NC2(N1)Cl.CC1=CC(=NN1)N>>ClC=1N=CC2=NC=NC2(N1)NC1=NNC(=C1)C | [CH3:1][c:2]1[cH:3][c:4]([NH2:5])[n:16][nH:17]1.Cl[C:6]12[N:7]=[CH:8][N:9]=[C:10]1[CH:11]=[N:12][C:13]([Cl:14])=[N:15]2>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][C:6]23[N:7]=[CH:8][N:9]=[C:10]2[CH:11]=[N:12][C:13]([Cl:14])=[N:15]3)[n:16][nH:17]1 | Cc1cc(N)n[nH]1.ClC1=NC2(Cl)N=CN=C2C=N1 | Cc1cc(NC23N=CN=C2C=NC(Cl)=N3)n[nH]1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | 9f6414acc7dc8d92deef57b71c36c65409f27886ed6c04cda812b2c2b3e36d96 | eea9a5e587609dc5fd77390cd39192bf408374166fb31275d4a6d328d3b38b84 | C1=NC=NC2(Nc3cc[nH]n3)N=CN=C12 | Cl-[C;H0;D4;+0:1]12-[#7:2]=[C:3](-[Cl;D1;H0:4])-[#7:5]=[C:6]-[C:7]-1=[#7:8]-[C:9]=[#7:10]-2.[NH2;D1;+0:11]-[c:12]1:[#7;a:13]:[#7;a:14]:[c:15]:[c:16]:1>>[Cl;D1;H0:4]-[C:3]1=[#7:2]-[C;H0;D4;+0:1]2(-[NH;D2;+0:11]-[c:12]3:[#7;a:13]:[#7;a:14]:[c:15]:[c:16]:3)-[#7:10]=[C:9]-[#7:8]=[C:7]-2-[C:6]=[#7:5]-1 | 58 | [{"value": 58.0, "product": "ClC=1N=CC2=NC=NC2(N1)NC1=NNC(=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.6, "product": "ClC=1N=CC2=NC=NC2(N1)NC1=NNC(=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | To a suspension of 2,4-dichloro-purine (2.0 g, 10.6 mmol) in anhydrous ethanol (10 mL) was added 5-methyl-1H-pyrazol-3-yl amine (2.05 g, 21.2 mmol). The resulting mixture was stirred at room temperature for 48 h. The resulting precipitate was collected by filtration, washed with ethanol, and dried under vacuum to affor... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Primary amine | Secondary amine | C1=NC=NC2N=CN=C12 | C1=NC=NC2N=CN=C12 | c1cn[nH]c1.C1=NC=NC2N=CN=C12 | HCl | C(C)O | null | 48 | Cc1cc(N)n[nH]1.ClC1=NC2(Cl)N=CN=C2C=N1>C(C)O>Cc1cc(NC23N=CN=C2C=NC(Cl)=N3)n[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-033fb5014fbd4547a14bf5c0235026b0 | CC1CCNCC1.Cc1cc(NC23N=CN=C2C=NC(Cl)=N3)n[nH]1>>Cc1cc(NC23N=CN=C2C=NC(N2CCC(C)CC2)=N3)[nH]n1 | ClC=1N=CC2=NC=NC2(N1)NC1=NNC(=C1)C.CC1CCNCC1.C([O-])([O-])=O.[K+].[K+]>>CC1CCN(CC1)C=1N=CC2=NC=NC2(N1)NC=1NN=C(C1)C | [NH:14]1[CH2:15][CH2:16][CH:17]([CH3:18])[CH2:19][CH2:20]1.Cl[C:13]1=[N:21][C:6]2([NH:5][c:4]3[cH:3][c:2]([CH3:1])[nH:23][n:22]3)[N:7]=[CH:8][N:9]=[C:10]2[CH:11]=[N:12]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][C:6]23[N:7]=[CH:8][N:9]=[C:10]2[CH:11]=[N:12][C:13]([N:14]2[CH2:15][CH2:16][CH:17]([CH3:18])[CH2:19][CH2:20]2)=[N:21]... | CC1CCNCC1.Cc1cc(NC23N=CN=C2C=NC(Cl)=N3)n[nH]1 | Cc1cc(NC23N=CN=C2C=NC(N2CCC(C)CC2)=N3)[nH]n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | bd107ca2f0c4326411f18bbf4c383fd979f0c194e59e94f098fb780e597038c5 | f42712f62a63a0590ff88b97f02f7ce55443e44af887e4114dc924862f99ddaa | C1=NC(N2CCCCC2)=NC2(Nc3ccn[nH]3)N=CN=C12 | Cl-[C;H0;D3;+0:1]1=[#7:2]-[C:3](-[#7:4]-[c:5]2:[c:6]:[c:7](-[C;D1;H3:8]):[nH;D2;+0:9]:[n;H0;D2;+0:10]:2)(-[#7:11])-[C:12](=[#7:13])-[C:14]=[#7:15]-1.[C:16]-[C:17]-[NH;D2;+0:18]-[C:19]-[C:20]>>[#7:11]-[C:3]1(-[#7:4]-[c:5]2:[c:6]:[c:7](-[C;D1;H3:8]):[n;H0;D2;+0:9]:[nH;D2;+0:10]:2)-[#7:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:18](-... | 90 | [{"value": 90.0, "product": "CC1CCN(CC1)C=1N=CC2=NC=NC2(N1)NC=1NN=C(C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.0, "product": "CC1CCN(CC1)C=1N=CC2=NC=NC2(N1)NC=1NN=C(C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a suspension of 2,4-dichloro-purine (2.0 g, 10.6 mmol) in anhydrous ethanol (10 mL) was added 5-methyl-1H-pyrazol-3-yl amine (2.05 g, 21.2 mmol). The resulting mixture was stirred at room temperature for 48 h. The resulting precipitate was collected by filtration, washed with ethanol, and dried under vacuum to affor... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Substituted imine.Secondary amine | Substituted imine.Tertiary amine | C1CCNCC1.C1=NC=NC2N=CN=C12 | C1=NC=NC2N=CN=C12.C1CC[NH]CC1 | c1cn[nH]c1.C1=NC=NC2N=CN=C12.C1CC[NH]CC1 | HCl | null | null | 2 | CC1CCNCC1.Cc1cc(NC23N=CN=C2C=NC(Cl)=N3)n[nH]1>>Cc1cc(NC23N=CN=C2C=NC(N2CCC(C)CC2)=N3)[nH]n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-90706312daec4ca2b316204aeffe5753 | Cc1cc(N)n[nH]1.Clc1nc(-c2ccccc2)cc2ccccc12>>Cc1cc(Nc2nc(-c3ccccc3)cc3ccccc23)[nH]n1 | ClC1=NC(=CC2=CC=CC=C12)C1=CC=CC=C1.NC1=NNC(=C1)C.C([O-])([O-])=O.[K+].[K+]>>CC=1C=C(NN1)NC1=NC(=CC2=CC=CC=C12)C1=CC=CC=C1 | [CH3:1][c:2]1[cH:3][c:4]([NH2:5])[n:22][nH:23]1.Cl[c:6]1[n:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]12>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][c:8](-[c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[cH:15][c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]23)[nH:22][n:23]1 | Cc1cc(N)n[nH]1.Clc1nc(-c2ccccc2)cc2ccccc12 | Cc1cc(Nc2nc(-c3ccccc3)cc3ccccc23)[nH]n1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 17c3dbb58f19c559a89452c2c52a32d81319b5dd6d11e225611cc478eba61c1b | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(-c2cc3ccccc3c(Nc3ccn[nH]3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5]):[c:6].[C;D1;H3:7]-[c:8]1:[c:9]:[c:10](-[NH2;D1;+0:11]):[n;H0;D2;+0:12]:[nH;D2;+0:13]:1>>[C;D1;H3:7]-[c:8]1:[c:9]:[c:10](-[NH;D2;+0:11]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5]):[c:6]):[nH;D2;+0:12]:[n;H0;D2;+0:13]:1 | null | [] | null | null | null | null | To a solution of 1-chloro-3-phenylisoquinoline (J. Het. Chem., 20, 1983, 121–128)(0.33 g, 1.37 mmol) in DMF (anhydrous, 5 mL) was added 3-amino-5-methylpyrazole (0.27 g, 2.74 mmol) and potassium carbonate (0.57 g, 4.13 mmol) and the resulting mixture was heated at reflux for 6 hours. The reaction mixture was then coole... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | c1cn[nH]c1.c1ccccc1.c1ccc2cnccc2c1 | HCl | CN(C)C=O | null | null | Cc1cc(N)n[nH]1.Clc1nc(-c2ccccc2)cc2ccccc12>CN(C)C=O>Cc1cc(Nc2nc(-c3ccccc3)cc3ccccc23)[nH]n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-020440c00af440c8b9cd3a3777146cf3 | FC(F)(F)c1ccccc1-c1cc2ccccc2c(Cl)n1.Nc1n[nH]c2ccccc12>>FC(F)(F)c1ccccc1-c1cc2ccccc2c(Nc2n[nH]c3ccccc23)n1 | ClC1=NC(=CC2=CC=CC=C12)C1=C(C=CC=C1)C(F)(F)F.N1N=C(C2=CC=CC=C12)N>>N1N=C(C2=CC=CC=C12)NC1=NC(=CC2=CC=CC=C12)C1=C(C=CC=C1)C(F)(F)F | Cl[c:19]1[c:18]2[c:13]([cH:12][c:11](-[c:10]3[c:5]([C:2]([F:1])([F:3])[F:4])[cH:6][cH:7][cH:8][cH:9]3)[n:30]1)[cH:14][cH:15][cH:16][cH:17]2.[NH2:20][c:21]1[n:22][nH:23][c:24]2[cH:25][cH:26][cH:27][cH:28][c:29]12>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1-[c:11]1[cH:12][c:13]2[cH:14][cH:15][cH:16][cH... | FC(F)(F)c1ccccc1-c1cc2ccccc2c(Cl)n1.Nc1n[nH]c2ccccc12 | FC(F)(F)c1ccccc1-c1cc2ccccc2c(Nc2n[nH]c3ccccc23)n1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 17c3dbb58f19c559a89452c2c52a32d81319b5dd6d11e225611cc478eba61c1b | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(-c2cc3ccccc3c(Nc3n[nH]c4ccccc34)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[c:8]1:[#7;a:9]:[#7;a:10]:[c:11]:[c:12]:1>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8]1:[#7;a:9]:[#7;a:10]:[c:11]:[c:12]:1):[c:4](:[c:5]):[c:6] | 27 | [{"value": 27.0, "product": "N1N=C(C2=CC=CC=C12)NC1=NC(=CC2=CC=CC=C12)C1=C(C=CC=C1)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 26.5, "product": "N1N=C(C2=CC=CC=C12)NC1=NC(=CC2=CC=CC=C12)C1=C(C=CC=C1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 1-chloro-3-(2-trifluoromethyl-phenyl)-isoquinoline (100 mg, 0.326 mmol) and 1H-indazol-3-ylamine (86 mg, 0.651 mmol) in ethanol (3 mL) was heated at 160 C and the solvent evaporated with a stream of nitrogen. The remaining oil was then heated at 160 C for 18 hours under nitrogen. The resulting melt was di... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | c1ccccc1.c1ccc2cnccc2c1.c1ccc2n[nH]cc2c1 | HCl | C(C)O | null | null | FC(F)(F)c1ccccc1-c1cc2ccccc2c(Cl)n1.Nc1n[nH]c2ccccc12>C(C)O>FC(F)(F)c1ccccc1-c1cc2ccccc2c(Nc2n[nH]c3ccccc23)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d2bf217eddca4257ae51da4d5cb2c928 | COC(=O)c1ccc(CN(Cc2ccccn2)C(=O)OC(C)(C)C)cc1>>CC(C)(C)OC(=O)N(Cc1ccc(C(=O)O)cc1)Cc1ccccn1 | C(=O)(OC(C)(C)C)N(CC1=NC=CC=C1)CC1=CC=C(C(=O)OC)C=C1.CO.[OH-].[Na+]>>C(=O)(OC(C)(C)C)N(CC1=NC=CC=C1)CC1=CC=C(C(=O)O)C=C1 | C[O:16][C:14]([c:13]1[cH:12][cH:11][c:10]([CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:19][c:20]2[cH:21][cH:22][cH:23][cH:24][n:25]2)[cH:18][cH:17]1)=[O:15]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]([CH2:9][c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[OH:16])[cH:17][cH:18]1)[CH2:19][c:2... | COC(=O)c1ccc(CN(Cc2ccccn2)C(=O)OC(C)(C)C)cc1 | CC(C)(C)OC(=O)N(Cc1ccc(C(=O)O)cc1)Cc1ccccn1 | null | null | C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(CNCc2ccccn2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 63.9 | [{"value": 63.9, "product": "C(=O)(OC(C)(C)C)N(CC1=NC=CC=C1)CC1=CC=C(C(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | DAY | The compound obtained in Example 1-1 (200.6 mg) was added with methanol (2 ml), THF (2 ml), and 1 mol/l aqueous solution of sodium hydroxide (2 ml), and the mixture was stirred for one day at room temperature. After the completion of the reaction, the solvent was removed by distillation and water (5 ml) was added. Aque... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccncc1 | Other | C1CCOC1 | null | 24 | COC(=O)c1ccc(CN(Cc2ccccn2)C(=O)OC(C)(C)C)cc1>C1CCOC1>CC(C)(C)OC(=O)N(Cc1ccc(C(=O)O)cc1)Cc1ccccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-639408831de942e6a598272ed67cc92c | COC(=O)Cc1ccc(CN(Cc2ccccn2)C(=O)OC(C)(C)C)cc1>>CC(C)(C)OC(=O)N(Cc1ccc(CC(=O)O)cc1)Cc1ccccn1 | C(=O)(OC(C)(C)C)N(CC1=NC=CC=C1)CC1=CC=C(C=C1)CC(=O)OC.[OH-].[Na+]>>C(=O)(OC(C)(C)C)N(CC1=NC=CC=C1)CC1=CC=C(C=C1)CC(=O)O | C[O:17][C:15]([CH2:14][c:13]1[cH:12][cH:11][c:10]([CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][n:26]2)[cH:19][cH:18]1)=[O:16]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]([CH2:9][c:10]1[cH:11][cH:12][c:13]([CH2:14][C:15](=[O:16])[OH:17])[cH:18][cH:1... | COC(=O)Cc1ccc(CN(Cc2ccccn2)C(=O)OC(C)(C)C)cc1 | CC(C)(C)OC(=O)N(Cc1ccc(CC(=O)O)cc1)Cc1ccccn1 | null | null | CO.C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(CNCc2ccccn2)cc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 98.3 | [{"value": 98.3, "product": "C(=O)(OC(C)(C)C)N(CC1=NC=CC=C1)CC1=CC=C(C=C1)CC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 35 | MINUTE | The compound obtained in Example 8-3 (83.2 mg) was dissolved in THF (0.8 ml) and methanol (0.8 ml). After the addition of 1 N aqueous solution of sodium hydroxide (0.8 ml), the mixture was stirred for 35 minutes at room temperature. After the reaction, the solvent was removed by distillation and the residue was dissolv... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccncc1 | Other | CO.C1CCOC1 | null | 0.583333 | COC(=O)Cc1ccc(CN(Cc2ccccn2)C(=O)OC(C)(C)C)cc1>CO.C1CCOC1>CC(C)(C)OC(=O)N(Cc1ccc(CC(=O)O)cc1)Cc1ccccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5fa1bf7313374de8b97081467abfed33 | O=C(NCCC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O)OCc1ccccc1>>N[C@@H](CCCNC(=O)OCc1ccccc1)C(=O)O | C(=O)(OCC1C2=CC=CC=C2C2=CC=CC=C12)N[C@@H](CCCNC(=O)OCC1=CC=CC=C1)C(=O)O.C(C)NCC>>C(=O)(OCC1=CC=CC=C1)NCCC[C@H](N)C(=O)O | O=C(OCC1c2ccccc2-c2ccccc21)[NH:1][C@@H:2]([CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:8])[O:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[C:17](=[O:18])[OH:19]>>[NH2:1][C@@H:2]([CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:8])[O:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[C:17](=[O:18])[OH:19] | O=C(NCCC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O)OCc1ccccc1 | N[C@@H](CCCNC(=O)OCc1ccccc1)C(=O)O | null | null | CN(C)C=O | Reduction | Hydrogenolysis of amides/imides/carbamates | 6b8c76d50ec667b483b13f7e325104eed6ba06fddb821da46e405c5dce0a3de5 | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | c1ccccc1 | O=C(-O-C-C1-c2:c:c:c:c:c:2-c2:c:c:c:c:c:2-1)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4](=[O;D1;H0:5])-[O;D1;H1:6] | 199.4 | [{"value": 199.4, "product": "C(=O)(OCC1=CC=CC=C1)NCCC[C@H](N)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | The compound obtained in Example 8-5 (122.8 mg) was dissolved in DMF (2.6 ml). After the addition of diethylamine (0.26 ml), the mixture was stirred for 2 hours at room temperature. After the reaction, the solvent was removed by distillation under reduced pressure and the residue was dried under vacuum to obtain the ti... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | c1ccc2c(c1)Cc1ccccc12 | null | c1ccccc1 | HO- | CN(C)C=O | null | 2 | O=C(NCCC[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O)OCc1ccccc1>CN(C)C=O>N[C@@H](CCCNC(=O)OCc1ccccc1)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-67abb265325d4c0db000f071744365b3 | CC(C)(C)OC(=O)N(Cc1ccc(CC(=O)N[C@@H](CCCNC2CCCc3cccnc32)C(=O)O)cc1)Cc1ccccn1>>O=C(Cc1ccc(CNCc2ccccn2)cc1)N[C@@H](CCCNC1CCCc2cccnc21)C(=O)O | C(=O)(OC(C)(C)C)N(CC1=NC=CC=C1)CC1=CC=C(C=C1)CC(=O)N[C@H](C(=O)O)CCCNC1CCCC=2C=CC=NC12.Cl.O1CCOCC1>>Cl.N1=C(C=CC=C1)CNCC1=CC=C(C=C1)CC(=O)N[C@H](C(=O)O)CCCNC1CCCC=2C=CC=NC12 | CC(C)(C)OC(=O)[N:10]([CH2:9][c:8]1[cH:7][cH:6][c:5]([CH2:4][C:3](=[O:2])[NH:20][C@@H:21]([CH2:22][CH2:23][CH2:24][NH:25][CH:26]2[CH2:27][CH2:28][CH2:29][c:30]3[cH:31][cH:32][cH:33][n:34][c:35]32)[C:36](=[O:37])[OH:38])[cH:19][cH:18]1)[CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][n:17]1>>[O:2]=[C:3]([CH2:4][c:5]1[cH:6][cH... | CC(C)(C)OC(=O)N(Cc1ccc(CC(=O)N[C@@H](CCCNC2CCCc3cccnc32)C(=O)O)cc1)Cc1ccccn1 | O=C(Cc1ccc(CNCc2ccccn2)cc1)N[C@@H](CCCNC1CCCc2cccnc21)C(=O)O | null | null | CO | Reduction | Boc amine deprotection | bbda4640db5f48af4538caded12fdadd56eacd6d4e5f7aefe46282d665df167e | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=C(Cc1ccc(CNCc2ccccn2)cc1)NCCCCNC1CCCc2cccnc21 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[c:3]:[#7;a:4])-[C:5]-[c:6]>>[#7;a:4]:[c:3]-[C:2]-[NH;D2;+0:1]-[C:5]-[c:6] | null | [] | null | null | 1.5 | HOUR | The compound obtained in Example 8-8 (18.0 mg) was dissolved in methanol (0.2 ml) and 4 mol/l hydrochloric acid/dioxane solution was added. The mixture was stirred for 1.5 hours at room temperature. After the reaction, the solvent was removed by distillation. The residue was purified by silica gel column chromatography... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | null | null | c1ccccc1.c1ccncc1.c1cnc2c(c1)CCCC2 | HO- | CO | null | 1.5 | CC(C)(C)OC(=O)N(Cc1ccc(CC(=O)N[C@@H](CCCNC2CCCc3cccnc32)C(=O)O)cc1)Cc1ccccn1>CO>O=C(Cc1ccc(CNCc2ccccn2)cc1)N[C@@H](CCCNC1CCCc2cccnc21)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3ccd70d7c63d4afe90a7dd07edba6d48 | O=C(O)c1ccc(CCBr)cc1>>COC(=O)c1ccc(CCBr)cc1 | BrCCC1=CC=C(C(=O)O)C=C1.CCN=C=NCCCN(C)C.Cl.C=1C=CC2=C(C1)N=NN2O>>BrCCC1=CC=C(C(=O)OC)C=C1 | [OH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][CH2:10][Br:11])[cH:12][cH:13]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][CH2:10][Br:11])[cH:12][cH:13]1 | O=C(O)c1ccc(CCBr)cc1 | COC(=O)c1ccc(CCBr)cc1 | null | null | CO | Miscellaneous | Protection of carboxylic acid | 56520e0abb4535dce9a663824ca803b71c2c0dd72dfd246317d953596a987bd2 | 2ccc7a30191c2c171b49e8a0217bee87430687dd0f567141eca025a75b7e3136 | c1ccccc1 | [O;D1;H0:1]=[C:2](-[OH;D1;+0:3])-[c:4]>>[C;D1;H3:5]-[O;H0;D2;+0:3]-[C:2](=[O;D1;H0:1])-[c:4] | 78.3 | [{"value": 78.3, "product": "BrCCC1=CC=C(C(=O)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 24 | HOUR | Commercially available 4-bromoethylbenzoic acid (997.9 mg) was dissolved in methanol (30 ml). After the addition of WSCI hydrochloride (1.2527 g) and HOBt (598.5 mg), the solution was stirred for 24 hours at 60° C. After the reaction, the solvent was removed by distillation. The residue was dissolved in chloroform, was... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | c1ccccc1 | Other | CO | 60 | 24 | O=C(O)c1ccc(CCBr)cc1>CO>COC(=O)c1ccc(CCBr)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a78758e5b0fc4b538301b9f611812224 | COC(=O)c1ccc(CCBr)cc1.NCc1ccccn1>>COC(=O)c1ccc(CCNCc2ccccn2)cc1 | N1=C(C=CC=C1)CN.C(C)(C)N(CC)C(C)C.BrCCC1=CC=C(C(=O)OC)C=C1>>N1=C(C=CC=C1)CNCCC1=CC=C(C(=O)OC)C=C1 | Br[CH2:10][CH2:9][c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:20][cH:19]1.[NH2:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][n:18]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][CH2:10][NH:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][n:18]2)[cH:19][cH:20]1 | COC(=O)c1ccc(CCBr)cc1.NCc1ccccn1 | COC(=O)c1ccc(CCNCc2ccccn2)cc1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CCNCc2ccccn2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[c:3].[#7;a:4]:[c:5]-[C:6]-[NH2;D1;+0:7]>>[#7;a:4]:[c:5]-[C:6]-[NH;D2;+0:7]-[CH2;D2;+0:1]-[C:2]-[c:3] | null | [] | 80 | CELSIUS | 2 | DAY | Commercially available 2-picolylamine (0.625 ml) was dissolved in toluene (15 ml) and diisopropylethylamine (0.715 ml) was added. After the addition of the compound obtained in Example 9-1 (499.7 mg), the mixture was stirred for two days at 80° C. After the reaction, toluene was added. The solution was washed with dist... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccncc1 | HBr | C1(=CC=CC=C1)C | 80 | 48 | COC(=O)c1ccc(CCBr)cc1.NCc1ccccn1>C1(=CC=CC=C1)C>COC(=O)c1ccc(CCNCc2ccccn2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1c9322052b654c65b143e6b66ad1272d | COC(=O)c1ccc(CCN(Cc2ccccn2)C(=O)OC(C)(C)C)cc1>>CC(C)(C)OC(=O)N(CCc1ccc(C(=O)O)cc1)Cc1ccccn1 | C(=O)(OC(C)(C)C)N(CC1=NC=CC=C1)CCC1=CC=C(C(=O)OC)C=C1.CO.[OH-].[Na+]>>C(=O)(OC(C)(C)C)N(CCC1=CC=C(C(=O)O)C=C1)CC1=NC=CC=C1 | C[O:17][C:15]([c:14]1[cH:13][cH:12][c:11]([CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][n:26]2)[cH:19][cH:18]1)=[O:16]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]([CH2:9][CH2:10][c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[OH:17])[cH:18][cH:1... | COC(=O)c1ccc(CCN(Cc2ccccn2)C(=O)OC(C)(C)C)cc1 | CC(C)(C)OC(=O)N(CCc1ccc(C(=O)O)cc1)Cc1ccccn1 | null | null | C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(CCNCc2ccccn2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 100.7 | [{"value": 100.7, "product": "C(=O)(OC(C)(C)C)N(CCC1=CC=C(C(=O)O)C=C1)CC1=NC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | The compound obtained in Example 9-3 (446.1 mg) was dissolved in THF (4.5 ml) and methanol (4.5 ml) After the addition of 1 mol/l aqueous solution of sodium hydroxide (4.5 ml), the mixture was stirred for 5 hours at room temperature. After the reaction, the solvent was removed by distillation and the residue was dissol... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccncc1 | Other | C1CCOC1 | null | 5 | COC(=O)c1ccc(CCN(Cc2ccccn2)C(=O)OC(C)(C)C)cc1>C1CCOC1>CC(C)(C)OC(=O)N(CCc1ccc(C(=O)O)cc1)Cc1ccccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f60a1a72dfff4c97885528a0b47a17df | CC(C)(C)OC(=O)N(CCc1ccc(C(=O)N[C@@H](CCCNCc2ccccn2)C(=O)O)cc1)Cc1ccccn1>>O=C(N[C@@H](CCCNCc1ccccn1)C(=O)O)c1ccc(CCNCc2ccccn2)cc1 | C(=O)(OC(C)(C)C)N(CC1=NC=CC=C1)CCC1=CC=C(C(=O)N[C@H](C(=O)O)CCCNCC2=NC=CC=C2)C=C1.Cl.O1CCOCC1>>Cl.N1=C(C=CC=C1)CNCCC1=CC=C(C(=O)N[C@H](C(=O)O)CCCNCC2=NC=CC=C2)C=C1 | CC(C)(C)OC(=O)[N:26]([CH2:25][CH2:24][c:23]1[cH:22][cH:21][c:20]([C:3](=[O:2])[NH:4][C@@H:5]([CH2:6][CH2:7][CH2:8][NH:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][n:16]2)[C:17](=[O:18])[OH:19])[cH:35][cH:34]1)[CH2:27][c:28]1[cH:29][cH:30][cH:31][cH:32][n:33]1>>[O:2]=[C:3]([NH:4][C@@H:5]([CH2:6][CH2:7][CH2:8][NH:9][CH2... | CC(C)(C)OC(=O)N(CCc1ccc(C(=O)N[C@@H](CCCNCc2ccccn2)C(=O)O)cc1)Cc1ccccn1 | O=C(N[C@@H](CCCNCc1ccccn1)C(=O)O)c1ccc(CCNCc2ccccn2)cc1 | null | null | CO | Reduction | Boc amine deprotection | bbda4640db5f48af4538caded12fdadd56eacd6d4e5f7aefe46282d665df167e | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=C(NCCCCNCc1ccccn1)c1ccc(CCNCc2ccccn2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]-[C:4]-[NH;D2;+0:1]-[C:2]-[C:3] | null | [] | null | null | 75 | MINUTE | The compound obtained in Example 10-1 (13.9 mg) was dissolved in methanol (0.28 ml) and 4 mol/l hydrochloric acid/dioxane solution (0.28 ml) was added to the solution. The mixture was stirred for 75 minutes at room temperature. After the completion of the reaction, the solvent was removed by distillation. The residue w... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | null | null | c1ccncc1.c1ccccc1.c1ccncc1 | HO- | CO | null | 1.25 | CC(C)(C)OC(=O)N(CCc1ccc(C(=O)N[C@@H](CCCNCc2ccccn2)C(=O)O)cc1)Cc1ccccn1>CO>O=C(N[C@@H](CCCNCc1ccccn1)C(=O)O)c1ccc(CCNCc2ccccn2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f9b2fbe11f024165adc3b05c701f2695 | CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1ccc(C(=O)N[C@@H](CCCNC2CCCc3cccnc32)C(=O)O)o1>>O=C(N[C@@H](CCCNC1CCCc2cccnc21)C(=O)O)c1ccc(CNCc2ccccn2)o1 | C(=O)(OC(C)(C)C)N(CC1=NC=CC=C1)CC1=CC=C(O1)C(=O)N[C@H](C(=O)O)CCCNC1CCCC=2C=CC=NC12.Cl.O1CCOCC1>>Cl.N1=C(C=CC=C1)CNCC1=CC=C(O1)C(=O)N[C@H](C(=O)O)CCCNC1CCCC=2C=CC=NC12 | CC(C)(C)OC(=O)[N:28]([CH2:27][c:26]1[cH:25][cH:24][c:23]([C:3](=[O:2])[NH:4][C@@H:5]([CH2:6][CH2:7][CH2:8][NH:9][CH:10]2[CH2:11][CH2:12][CH2:13][c:14]3[cH:15][cH:16][cH:17][n:18][c:19]32)[C:20](=[O:21])[OH:22])[o:36]1)[CH2:29][c:30]1[cH:31][cH:32][cH:33][cH:34][n:35]1>>[O:2]=[C:3]([NH:4][C@@H:5]([CH2:6][CH2:7][CH2:8][N... | CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1ccc(C(=O)N[C@@H](CCCNC2CCCc3cccnc32)C(=O)O)o1 | O=C(N[C@@H](CCCNC1CCCc2cccnc21)C(=O)O)c1ccc(CNCc2ccccn2)o1 | null | null | CO | Reduction | Boc amine deprotection | bbda4640db5f48af4538caded12fdadd56eacd6d4e5f7aefe46282d665df167e | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=C(NCCCCNC1CCCc2cccnc21)c1ccc(CNCc2ccccn2)o1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[c:3]:[#8;a:4])-[C:5]-[c:6]:[#7;a:7]>>[#7;a:7]:[c:6]-[C:5]-[NH;D2;+0:1]-[C:2]-[c:3]:[#8;a:4] | null | [] | null | null | 3 | HOUR | The compound obtained in Example 11-5 (30.6 mg) was dissolved in methanol (0.7 ml), and 4 mol/l hydrochloric acid/dioxane solution (0.7 ml) was added. The mixture was stirred for 3 hours at room temperature. After the reaction, the solvent was removed by distillation. The residue was purified by silica gel column chrom... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | null | null | c1cnc2c(c1)CCCC2.c1ccoc1.c1ccncc1 | HO- | CO | null | 3 | CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1ccc(C(=O)N[C@@H](CCCNC2CCCc3cccnc32)C(=O)O)o1>CO>O=C(N[C@@H](CCCNC1CCCc2cccnc21)C(=O)O)c1ccc(CNCc2ccccn2)o1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d50513840ecb42d3af2d9a84c664dac4 | COC(=O)c1ccc(C)nc1.NCc1ccccn1>>COC(=O)c1ccc(CNCc2ccccn2)nc1 | CC1=NC=C(C(=O)OC)C=C1.BrN1C(CCC1=O)=O.C([O-])([O-])=O.[K+].[K+].N1=C(C=CC=C1)CN>>N1=C(C=CC=C1)CNCC1=NC=C(C(=O)OC)C=C1 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH3:9])[n:18][cH:19]1.[NH2:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][n:17]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][NH:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][n:17]2)[n:18][cH:19]1 | COC(=O)c1ccc(C)nc1.NCc1ccccn1 | COC(=O)c1ccc(CNCc2ccccn2)nc1 | null | null | C(Cl)(Cl)Cl.CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 3c2788b3f372b76c1d2ee0d77963cb247b210aa8a28e76637b4e731826c4252a | c6874c6af41d3b1c4f7668e1cd342c90252d0e77f4317d31b3193ebc2f9501a3 | c1ccc(CNCc2ccccn2)nc1 | [#7;a:1]:[c:2]-[C:3]-[NH2;D1;+0:4].[CH3;D1;+0:5]-[c:6](:[c:7]):[#7;a:8]:[c:9]>>[#7;a:1]:[c:2]-[C:3]-[NH;D2;+0:4]-[CH2;D2;+0:5]-[c:6](:[c:7]):[#7;a:8]:[c:9] | null | [] | 70 | CELSIUS | 22 | HOUR | Commercially available methyl 6-methylnicotinate (2.5116 g) was dissolved in chloroform (50 ml), and N-bromosuccinimide (3.5682 g) and azoisobutylonitrile (290.4 mg) were added to the solution. The mixture was stirred for 22 hours at 70° C. After the reaction, the solvent was removed by distillation. The residue was pu... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary amine | null | null | c1ccncc1.c1ccncc1 | null | C(Cl)(Cl)Cl.CN(C)C=O | 70 | 22 | COC(=O)c1ccc(C)nc1.NCc1ccccn1>C(Cl)(Cl)Cl.CN(C)C=O>COC(=O)c1ccc(CNCc2ccccn2)nc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a78d72c6fe744272bcfd3a458c7ab371 | COC(=O)c1ccc(CN(Cc2ccccn2)C(=O)OC(C)(C)C)nc1>>CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1ccc(C(=O)O)cn1 | C(=O)(OC(C)(C)C)N(CC1=NC=CC=C1)CC1=NC=C(C(=O)OC)C=C1.[OH-].[Na+]>>C(=O)(OC(C)(C)C)N(CC1=NC=CC=C1)CC1=NC=C(C(=O)O)C=C1 | C[O:23][C:21]([c:20]1[cH:19][cH:18][c:17]([CH2:16][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][n:15]2)[n:25][cH:24]1)=[O:22]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]([CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][n:15]1)[CH2:16][c:17]1[cH:18][cH:19][c:20]([... | COC(=O)c1ccc(CN(Cc2ccccn2)C(=O)OC(C)(C)C)nc1 | CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1ccc(C(=O)O)cn1 | null | null | CO.C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(CNCc2ccccn2)nc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 82.3 | [{"value": 82.3, "product": "C(=O)(OC(C)(C)C)N(CC1=NC=CC=C1)CC1=NC=C(C(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | The compound obtained in Example 12-2 (351.3 mg) was dissolved in methanol (3.5 ml) and THF (3.5 ml). After the addition of 1 mol/l aqueous solution of sodium hydroxide (3.5 ml), the mixture was stirred for 2 hours at room temperature. After the reaction, the solvent was removed by distillation. The residue was dissolv... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccncc1.c1ccncc1 | Other | CO.C1CCOC1 | null | 2 | COC(=O)c1ccc(CN(Cc2ccccn2)C(=O)OC(C)(C)C)nc1>CO.C1CCOC1>CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1ccc(C(=O)O)cn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5d6d23489ab9488382c98bbf6eb9445a | CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1ccc(C(=O)O)cn1.N[C@@H](CCCNC(=O)OCc1ccccc1)C(=O)O>>CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1ccc(C(=O)N[C@@H](CCCNC(=O)OCc2ccccc2)C(=O)O)cn1 | C(=O)(OC(C)(C)C)N(CC1=NC=CC=C1)CC1=NC=C(C(=O)O)C=C1.CCN=C=NCCCN(C)C.Cl.C=1C=CC2=C(C1)N=NN2O.C(=O)(OCC1=CC=CC=C1)NCCC[C@H](N)C(=O)O>>C(=O)(OC(C)(C)C)N(CC1=NC=CC=C1)CC1=NC=C(C=C1)C(=O)N[C@@H](CCCNC(=O)OCC1=CC=CC=C1)C(=O)O | O[C:21]([c:20]1[cH:19][cH:18][c:17]([CH2:16][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][n:15]2)[n:43][cH:42]1)=[O:22].[NH2:23][C@@H:24]([CH2:25][CH2:26][CH2:27][NH:28][C:29](=[O:30])[O:31][CH2:32][c:33]1[cH:34][cH:35][cH:36][cH:37][cH:38]1)[C:39](=[O:40])[OH:41]>>[C... | CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1ccc(C(=O)O)cn1.N[C@@H](CCCNC(=O)OCc1ccccc1)C(=O)O | CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1ccc(C(=O)N[C@@H](CCCNC(=O)OCc2ccccc2)C(=O)O)cn1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCCCNC(=O)c1ccc(CNCc2ccccn2)nc1)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].[C:8]-[C:9](-[NH2;D1;+0:10])-[C:11](=[O;D1;H0:12])-[O;D1;H1:13]>>[C:8]-[C:9](-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7])-[C:11](=[O;D1;H0:12])-[O;D1;H1:13] | 107.6 | [{"value": 107.6, "product": "C(=O)(OC(C)(C)C)N(CC1=NC=CC=C1)CC1=NC=C(C=C1)C(=O)N[C@@H](CCCNC(=O)OCC1=CC=CC=C1)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The compound obtained in Example 8-6 (165.3 mg) was dissolved in DMF (3 ml). After the addition of WSCI hydrochloride (78.5 mg), HOBt (40.1 mg), and the compound obtained in Example 12-3 (90.4 mg), the mixture was stirred for 23 hours at room temperature. After the reaction, the solvent was removed by distillation. The... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccncc1.c1ccccc1 | HO- | CN(C)C=O | null | null | CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1ccc(C(=O)O)cn1.N[C@@H](CCCNC(=O)OCc1ccccc1)C(=O)O>CN(C)C=O>CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1ccc(C(=O)N[C@@H](CCCNC(=O)OCc2ccccc2)C(=O)O)cn1 |
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