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-c3a75813d0b24864aa4f7cd526efd6aa | ord-8c5fd294e6cf401c9bc897f31628a4c5 | C[C@@H]1CC[C@@H](NC(=O)OC(C)(C)C)[C@H](O)CN1S(=O)(=O)c1ccccn1>>C[C@@H]1CC[C@@H](N)[C@H](O)CN1S(=O)(=O)c1ccccn1 | Cl.C(C)(C)(C)OC(N[C@H]1[C@@H](CN([C@@H](CC1)C)S(=O)(=O)C1=NC=CC=C1)O)=O>>N[C@H]1[C@@H](CN([C@@H](CC1)C)S(=O)(=O)C1=NC=CC=C1)O | CC(C)(C)OC(=O)[NH:6][C@@H:5]1[CH2:4][CH2:3][C@@H:2]([CH3:1])[N:10]([S:11](=[O:12])(=[O:13])[c:14]2[cH:15][cH:16][cH:17][cH:18][n:19]2)[CH2:9][C@H:7]1[OH:8]>>[CH3:1][C@@H:2]1[CH2:3][CH2:4][C@@H:5]([NH2:6])[C@H:7]([OH:8])[CH2:9][N:10]1[S:11](=[O:12])(=[O:13])[c:14]1[cH:15][cH:16][cH:17][cH:18][n:19]1 | C[C@@H]1CC[C@@H](NC(=O)OC(C)(C)C)[C@H](O)CN1S(=O)(=O)c1ccccn1 | C[C@@H]1CC[C@@H](N)[C@H](O)CN1S(=O)(=O)c1ccccn1 | null | null | O1CCOCC1.C1(=CC=CC=C1)C.CO | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=S(=O)(c1ccccn1)N1CCCCCC1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4] | null | [] | null | null | 1 | HOUR | HCl in dioxane (4.0 M, 10 ml) was added to a stirred solution. [(3R,4R,7R)-3-Hydroxy-7-methyl-1-(pyridine-2-sulfonyl)-azepan-4-yl]-carbamic acid tert-butyl ester (0.6 g, 1.55 mmol) in MeOH (10 ml). The reaction mixture was stirred for 1 h at RT, then was diluted with toluene (20 ml), concentrated in vacuo by rotary eva... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | C1CCC[NH]CC1.c1ccncc1 | HO- | O1CCOCC1.C1(=CC=CC=C1)C.CO | null | 1 | C[C@@H]1CC[C@@H](NC(=O)OC(C)(C)C)[C@H](O)CN1S(=O)(=O)c1ccccn1>O1CCOCC1.C1(=CC=CC=C1)C.CO>C[C@@H]1CC[C@@H](N)[C@H](O)CN1S(=O)(=O)c1ccccn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-88e1ce2fbff54f2cb450c53d5c5fc09d | CC(C)CC(C(=O)O)c1cccc(-c2ccccc2)c1.C[C@@H]1CC[C@@H](N)[C@H](O)CN1S(=O)(=O)c1ccccn1>>CC(C)CC(C(=O)N[C@@H]1CC[C@@H](C)N(S(=O)(=O)c2ccccn2)C[C@H]1O)c1cccc(-c2ccccc2)c1 | C1(=CC(=CC=C1)C(C(=O)O)CC(C)C)C1=CC=CC=C1.N[C@H]1[C@@H](CN([C@@H](CC1)C)S(=O)(=O)C1=NC=CC=C1)O.CCN=C=NCCCN(C)C.C=1C=CC2=C(C1)N=NN2O.C(C)(C)N(CC)C(C)C>>C[C@@H]1CC[C@H]([C@@H](CN1S(=O)(=O)C1=NC=CC=C1)O)NC(C(CC(C)C)C=1C=C(C=CC1)C1=CC=CC=C1)=O | O[C:6]([CH:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[c:27]1[cH:28][cH:29][cH:30][c:31](-[c:32]2[cH:33][cH:34][cH:35][cH:36][cH:37]2)[cH:38]1)=[O:7].[NH2:8][C@@H:9]1[CH2:10][CH2:11][C@@H:12]([CH3:13])[N:14]([S:15](=[O:16])(=[O:17])[c:18]2[cH:19][cH:20][cH:21][cH:22][n:23]2)[CH2:24][C@H:25]1[OH:26]>>[CH3:1][CH:2]([CH3:3])[CH2:4]... | CC(C)CC(C(=O)O)c1cccc(-c2ccccc2)c1.C[C@@H]1CC[C@@H](N)[C@H](O)CN1S(=O)(=O)c1ccccn1 | CC(C)CC(C(=O)N[C@@H]1CC[C@@H](C)N(S(=O)(=O)c2ccccn2)C[C@H]1O)c1cccc(-c2ccccc2)c1 | null | null | CN(C)C=O.CCOC(=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Cc1cccc(-c2ccccc2)c1)N[C@@H]1CCCN(S(=O)(=O)c2ccccn2)CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[c:5].[C:6]-[C:7](-[NH2;D1;+0:8])-[C:9]>>[C:6]-[C:7](-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[c:5])-[C:9] | 62 | [{"value": 62.0, "product": "C[C@@H]1CC[C@H]([C@@H](CN1S(=O)(=O)C1=NC=CC=C1)O)NC(C(CC(C)C)C=1C=C(C=CC1)C1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.6, "product": "C[C@@H]1CC[C@H]([C@@H](CN1S(=O)(=O)C1=NC=CC=C1)O)NC(C(CC(C)C)C=1C=C(C=CC1)C1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIE... | null | null | null | null | 2-Biphenyl-3-yl-4-methyl-pentanoic acid (270 mg, 1.0 mmol, preparation described in J. Am. Chem. Soc. 1997, 120, 9114), and (3R,4R,7R)-4-Amino-7-methyl-1-(pyridine-2-sulfonyl)-azepan-3-ol (320 mg, 1.0mmol, Example 1k), EDCI (190 mg, 1.0 mmol), HOBT (135 mg, 1.0 mmol) and diisopropylethylamine (1.7 g, 0.23 ml, 1.3 mmol)... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CCC[NH]CC1.c1ccncc1.c1ccccc1.c1ccccc1 | HO- | CN(C)C=O.CCOC(=O)C | null | null | CC(C)CC(C(=O)O)c1cccc(-c2ccccc2)c1.C[C@@H]1CC[C@@H](N)[C@H](O)CN1S(=O)(=O)c1ccccn1>CN(C)C=O.CCOC(=O)C>CC(C)CC(C(=O)N[C@@H]1CC[C@@H](C)N(S(=O)(=O)c2ccccn2)C[C@H]1O)c1cccc(-c2ccccc2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-963533c2871343e58992cbadacb6eca0 | CNC(=O)c1cc(Cl)ccn1.Nc1ccc(O)cc1[N+](=O)[O-]>>CNC(=O)c1cc(Oc2ccc(N)c([N+](=O)[O-])c2)ccn1 | NC1=C(C=C(C=C1)O)[N+](=O)[O-].C[Si](C)(C)[N-][Si](C)(C)C.[K+].ClC1=CC(=NC=C1)C(=O)NC.C([O-])([O-])=O.[K+].[K+]>>NC1=C(C=C(C=C1)OC1=CC(=NC=C1)C(=O)NC)[N+](=O)[O-] | Cl[c:7]1[cH:6][c:5]([C:3]([NH:2][CH3:1])=[O:4])[n:21][cH:20][cH:19]1.[OH:8][c:9]1[cH:10][cH:11][c:12]([NH2:13])[c:14]([N+:15](=[O:16])[O-:17])[cH:18]1>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][c:12]([NH2:13])[c:14]([N+:15](=[O:16])[O-:17])[cH:18]2)[cH:19][cH:20][n:21]1 | CNC(=O)c1cc(Cl)ccn1.Nc1ccc(O)cc1[N+](=O)[O-] | CNC(=O)c1cc(Oc2ccc(N)c([N+](=O)[O-])c2)ccn1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 99925b30dd2603ae575cba81b58435d015cd6b7267cf347380904f25833af5f2 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ccncc2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[C:6](-[#7:7])=[O;D1;H0:8]):[c:9]:1.[OH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[#7:7]-[C:6](=[O;D1;H0:8])-[c:5]1:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:10]-[c:11](:[c:12]):[c:13]):[c:9]:1 | null | [] | 90 | CELSIUS | 3 | DAY | A mixture containing 4-amino-3-nitrophenol (1 eq) and potassium bis(trimethylsilyl)amide (2 eq) was stirred in dimethylformamide for 2 hours at room temperature. To this mixture was added (4-chloro(2-pyridyl))-N-methylcarboxamide (1 eq) and potassium carbonate (1.2 eq) and stirred at 90° C. for 3 days. The reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | HCl | CN(C=O)C | 90 | 72 | CNC(=O)c1cc(Cl)ccn1.Nc1ccc(O)cc1[N+](=O)[O-]>CN(C=O)C>CNC(=O)c1cc(Oc2ccc(N)c([N+](=O)[O-])c2)ccn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-da96264e0f81436bab3b63be0e66a636 | CNC(=O)c1cc(Cl)ccn1.Oc1ccc2sc(Nc3ccc(Br)cc3)nc2c1>>CNC(=O)c1cc(Oc2ccc3sc(Nc4ccc(Br)cc4)nc3c2)ccn1 | BrC1=CC=C(C=C1)NC=1SC2=C(N1)C=C(C=C2)O.C[Si](C)(C)[N-][Si](C)(C)C.[K+].ClC1=CC(=NC=C1)C(=O)NC.C([O-])([O-])=O.[K+].[K+]>>BrC1=CC=C(C=C1)NC=1SC2=C(N1)C=C(C=C2)OC2=CC(=NC=C2)C(=O)NC | Cl[c:7]1[cH:6][c:5]([C:3]([NH:2][CH3:1])=[O:4])[n:28][cH:27][cH:26]1.[OH:8][c:9]1[cH:10][cH:11][c:12]2[s:13][c:14]([NH:15][c:16]3[cH:17][cH:18][c:19]([Br:20])[cH:21][cH:22]3)[n:23][c:24]2[cH:25]1>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][c:12]3[s:13][c:14]([NH:15][c:16]4[cH:17][cH:18][c:19]... | CNC(=O)c1cc(Cl)ccn1.Oc1ccc2sc(Nc3ccc(Br)cc3)nc2c1 | CNC(=O)c1cc(Oc2ccc3sc(Nc4ccc(Br)cc4)nc3c2)ccn1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 99925b30dd2603ae575cba81b58435d015cd6b7267cf347380904f25833af5f2 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Nc2nc3cc(Oc4ccncc4)ccc3s2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[C:6](-[#7:7])=[O;D1;H0:8]):[c:9]:1.[#7;a:10]:[c:11]:[c:12]:[c:13](-[OH;D1;+0:14]):[c:15]>>[#7:7]-[C:6](=[O;D1;H0:8])-[c:5]1:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:14]-[c:13](:[c:15]):[c:12]:[c:11]:[#7;a:10]):[c:9]:1 | null | [] | null | null | null | null | The mixture containing 2-[(4-bromophenyl)amino]benzothiazol-5-ol (1 eq), Potassiumbis(trimethylsilyl)amide (4 eq), was stirred in dimethylformamide for 30 min at room temperature. To this mixture was added (4-chloro(2-pyridyl)-N-methyl-carboxamide (1 eq) and Potassium carbonate (1.2 eq) and microwaved for 6 mins at 150... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccc2scnc2c1.c1ccccc1 | HCl | CN(C=O)C | null | null | CNC(=O)c1cc(Cl)ccn1.Oc1ccc2sc(Nc3ccc(Br)cc3)nc2c1>CN(C=O)C>CNC(=O)c1cc(Oc2ccc3sc(Nc4ccc(Br)cc4)nc3c2)ccn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-071bdbcaee6d468c9d5c289c3f9d91f7 | CNC(=O)c1cc(Cl)ccn1.Nc1ccc(O)cc1[N+](=O)[O-]>>CNC(=O)c1cc(Oc2ccc(N)c([N+](=O)[O-])c2)ccn1 | NC1=C(C=C(C=C1)O)[N+](=O)[O-].C[Si](C)(C)[N-][Si](C)(C)C.[K+].ClC1=CC(=NC=C1)C(=O)NC.C([O-])([O-])=O.[K+].[K+]>>NC1=C(C=C(OC2=CC(=NC=C2)C(=O)NC)C=C1)[N+](=O)[O-] | Cl[c:7]1[cH:6][c:5]([C:3]([NH:2][CH3:1])=[O:4])[n:21][cH:20][cH:19]1.[OH:8][c:9]1[cH:10][cH:11][c:12]([NH2:13])[c:14]([N+:15](=[O:16])[O-:17])[cH:18]1>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][c:12]([NH2:13])[c:14]([N+:15](=[O:16])[O-:17])[cH:18]2)[cH:19][cH:20][n:21]1 | CNC(=O)c1cc(Cl)ccn1.Nc1ccc(O)cc1[N+](=O)[O-] | CNC(=O)c1cc(Oc2ccc(N)c([N+](=O)[O-])c2)ccn1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 99925b30dd2603ae575cba81b58435d015cd6b7267cf347380904f25833af5f2 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ccncc2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[C:6](-[#7:7])=[O;D1;H0:8]):[c:9]:1.[OH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[#7:7]-[C:6](=[O;D1;H0:8])-[c:5]1:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:10]-[c:11](:[c:12]):[c:13]):[c:9]:1 | 72 | [{"value": 72.0, "product": "NC1=C(C=C(OC2=CC(=NC=C2)C(=O)NC)C=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.5, "product": "NC1=C(C=C(OC2=CC(=NC=C2)C(=O)NC)C=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 8 | HOUR | A mixture containing 4-amino-3-nitrophenol 5 (1.0 g, 6.4 mmol), potassium bis(trimethylsilyl)amide (2.58 g, 12.8mmol) was stirred in DMF (50 ml) for 2 hours at rt. To this mixture was added (4-chloro(2-pyridyl))-N-methylcarboxamide 4 (1.09 g, 6.4 mmol) and potassium carbonate (0.5 g, 7.6 mmol) and stirred at 90° C. ove... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | HCl | CN(C)C=O | 90 | 8 | CNC(=O)c1cc(Cl)ccn1.Nc1ccc(O)cc1[N+](=O)[O-]>CN(C)C=O>CNC(=O)c1cc(Oc2ccc(N)c([N+](=O)[O-])c2)ccn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ab655c226c6f4bdaa38913a1d9d27f6d | Cn1c(Nc2ccc(Cl)cc2)nc2cc(Oc3ccnc(C#N)c3)ccc21.NCCN>>Cn1c(Nc2ccc(Cl)cc2)nc2cc(Oc3ccnc(C4=NCCN4)c3)ccc21 | OS(=O)(=O)O.ClC1=CC=C(C=C1)NC1=NC2=C(N1C)C=CC(=C2)OC2=CC(=NC=C2)C#N.C(CN)N>>ClC1=CC=C(C=C1)NC1=NC2=C(N1C)C=CC(=C2)OC2=CC(=NC=C2)C=2NCCN2 | [CH3:1][n:2]1[c:3]([NH:4][c:5]2[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]2)[n:12][c:13]2[cH:14][c:15]([O:16][c:17]3[cH:18][cH:19][n:20][c:21]([C:22]#[N:23])[cH:27]3)[cH:28][cH:29][c:30]12.N[CH2:24][CH2:25][NH2:26]>>[CH3:1][n:2]1[c:3]([NH:4][c:5]2[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]2)[n:12][c:13]2[cH:14][c:15]([O:16][c:... | Cn1c(Nc2ccc(Cl)cc2)nc2cc(Oc3ccnc(C#N)c3)ccc21.NCCN | Cn1c(Nc2ccc(Cl)cc2)nc2cc(Oc3ccnc(C4=NCCN4)c3)ccc21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 44acbf70f9cc2ac0a229971bc6e7c77034e28fcd162de6449941e21cd576fef7 | e5ee524a9b0e5a2fe21766a24b1795b0d2b08a43f7dda8289a0ee59c7b4777e1 | c1ccc(Nc2nc3cc(Oc4ccnc(C5=NCCN5)c4)ccc3[nH]2)cc1 | N-[CH2;D2;+0:1]-[C:2]-[NH2;D1;+0:3].[N;H0;D1;+0:4]#[C;H0;D2;+0:5]-[c:6](:[c:7]):[#7;a:8]:[c:9]>>[c:9]:[#7;a:8]:[c:6](-[C;H0;D3;+0:5]1=[N;H0;D2;+0:4]-[CH2;D2;+0:1]-[C:2]-[NH;D2;+0:3]-1):[c:7] | null | [] | null | null | 72 | HOUR | H2SO4 (454 mg) was added cautiously to a suspension of 4-[2-(4-chloro-phenylamino)-1-methyl-1H-benzoimidazol-5-yloxy]-pyridine-2-carbonitrile (60.0 mg) in ethylenediamine (0.50 mL). The system was shaken at room temperature for 72 hrs, then poured onto ice/NaHCO3. The solid product was collected, washed (H2O) air-dried... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine.Primary amine | Secondary amine | null | C1=NCCN1 | c1ccccc1.c1ccc2[nH]cnc2c1.c1ccncc1.C1=NCCN1 | Other | null | null | 72 | Cn1c(Nc2ccc(Cl)cc2)nc2cc(Oc3ccnc(C#N)c3)ccc21.NCCN>>Cn1c(Nc2ccc(Cl)cc2)nc2cc(Oc3ccnc(C4=NCCN4)c3)ccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1795322710d64a18827233237661e114 | COc1ccc(O)c([N+](=O)[O-])c1>>COc1ccc(O)c(N)c1 | COC1=CC(=C(C=C1)O)[N+](=O)[O-]>>NC1=C(C=CC(=C1)OC)O | O=[N+:9]([O-])[c:8]1[c:6]([OH:7])[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:10]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[c:8]([NH2:9])[cH:10]1 | COc1ccc(O)c([N+](=O)[O-])c1 | COc1ccc(O)c(N)c1 | null | [Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The mixture containing 4-methoxy-2-nitrophenol in methanol with catalytic amount of 10% Pd/C was hydrogenated until disappearance of yellow color to yield 2-amino-4-methoxyphenol. MS: MH+=140.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Pd].CO | null | null | COc1ccc(O)c([N+](=O)[O-])c1>[Pd].CO>COc1ccc(O)c(N)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5bb9ac08edac4f298e8c88f6c4bce75c | CCOC(=S)S.COc1ccc(O)c(N)c1>>COc1ccc2oc(S)nc2c1 | Cl.NC1=C(C=CC(=C1)OC)O.C(C)OC(=S)S.[K]>>COC=1C=CC2=C(N=C(O2)S)C1 | CCO[C:8](S)=[S:9].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[c:11]([NH2:10])[cH:12]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[o:7][c:8]([SH:9])[n:10][c:11]2[cH:12]1 | CCOC(=S)S.COc1ccc(O)c(N)c1 | COc1ccc2oc(S)nc2c1 | null | null | N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | cbd796ad84a3d0f4f6a7a8057a682577715ca2073711c8f8b817da9ab6bfd06c | 823bc935aa85db31214f5df7ab28f890020dcca64ae332d898272b243d751e45 | c1ccc2ocnc2c1 | C-C-O-[C;H0;D3;+0:1](-S)=[S;H0;D1;+0:2].[NH2;D1;+0:3]-[c:4](:[c:5]):[c:6](-[OH;D1;+0:7]):[c:8]>>[SH;D1;+0:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:3]:[c:4](:[c:5]):[c:6](:[c:8]):[o;H0;D2;+0:7]:1 | null | [] | null | null | null | null | The mixture containing 2-amino-4-methoxyphenol(1 eq) and O-ethylxanthic acid, potassium salt (1.1 eq) in pyridine was refluxed for two hours. The resultant mixture was poured in to ice/water containing hydrochloric acid to yield a 5-methoxybenzoxazole-2-thiol as a tan solid. MS: MH+=182
Conditions: See reaction.notes.p... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Aromatic alcohol.Primary amine.Thiocarbonyl | Aromatic thiol | c1ccccc1 | c1ccc2ocnc2c1 | c1ccc2ocnc2c1 | Other | N1=CC=CC=C1 | null | null | CCOC(=S)S.COc1ccc(O)c(N)c1>N1=CC=CC=C1>COc1ccc2oc(S)nc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2e97f87fdbdf42edaf1ff767056716ef | COc1ccc2oc(S)nc2c1.O=S(Cl)Cl>>COc1ccc2oc(Cl)nc2c1 | COC=1C=CC2=C(N=C(O2)S)C1.CN(C)C=O.S(=O)(Cl)Cl>>ClC=1OC2=C(N1)C=C(C=C2)OC | S[c:8]1[o:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:12][c:11]2[n:10]1.O=S(Cl)[Cl:9]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[o:7][c:8]([Cl:9])[n:10][c:11]2[cH:12]1 | COc1ccc2oc(S)nc2c1.O=S(Cl)Cl | COc1ccc2oc(Cl)nc2c1 | null | null | null | Functional Group Interconversion | OtherReaction | 1c41bf5098d22e1f88c8b16e9d2c9e06b431e9e2ad47b4751567995db94396e2 | a58f0859c9c497bf36b64745c3cc5a524c946cefa35cff91cc1283f5fe2c360f | c1ccc2ocnc2c1 | Cl-S(=O)-[Cl;H0;D1;+0:1].S-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[c:5]:[#8;a:6]:1>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[c:5]:[#8;a:6]:1 | null | [] | null | null | null | null | The mixture containing 5-methoxybenzoxazole-2-thiol was heated in thionyl chloride with a drop of DMF. The resultant mixture was concentrated and partitioned between ethyl acetate and water. The organic layer was washed with brine and dried and concentrated. Purification on a silica gel column gave 2-chloro-5-methoxybe... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic thiol | Aromatic halide | c1ccc2ocnc2c1 | c1ccc2ocnc2c1 | c1ccc2ocnc2c1 | HCl | null | null | null | COc1ccc2oc(S)nc2c1.O=S(Cl)Cl>>COc1ccc2oc(Cl)nc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d46419144c4b457395c31c7c0a85f395 | COc1ccc2oc(Cl)nc2c1.Nc1ccc(Br)cc1>>COc1ccc2oc(Nc3ccc(Br)cc3)nc2c1 | ClC=1OC2=C(N1)C=C(C=C2)OC.BrC1=CC=C(N)C=C1.C(C)(C)N(CC)C(C)C>>BrC1=CC=C(C=C1)NC=1OC2=C(N1)C=C(C=C2)OC | Cl[c:8]1[o:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:19][c:18]2[n:17]1.[NH2:9][c:10]1[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[o:7][c:8]([NH:9][c:10]3[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]3)[n:17][c:18]2[cH:19]1 | COc1ccc2oc(Cl)nc2c1.Nc1ccc(Br)cc1 | COc1ccc2oc(Nc3ccc(Br)cc3)nc2c1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 56122dec6b9213d311e74462a865e17687f4178b6e2e5d6eb3cc0c5bc48da7a7 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nc3ccccc3o2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#8;a:5]:1.[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#8;a:5]:1):[c:9] | null | [] | null | null | null | null | The mixture containing 2-chloro-5-methoxybenzoxazole(1 eq), 4-bromoaniline (2 eq) and diisopropylethylamine was refluxed in dimethylformamide. The resultant mixture was concentrated and partitioned between ethyl acetate and water. The organic layer was washed with brine and dried. Purification on silica gel gave (4-bro... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ocnc2c1 | c1ccc2ocnc2c1 | c1ccc2ocnc2c1.c1ccccc1 | HCl | CN(C=O)C | null | null | COc1ccc2oc(Cl)nc2c1.Nc1ccc(Br)cc1>CN(C=O)C>COc1ccc2oc(Nc3ccc(Br)cc3)nc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-de00dfaa78694367b14596480705f5c0 | COc1ccc2oc(Nc3ccc(Br)cc3)nc2c1>>Oc1ccc2oc(Nc3ccc(Br)cc3)nc2c1 | BrC1=CC=C(C=C1)NC=1OC2=C(N1)C=C(C=C2)OC.Br>>BrC1=CC=C(C=C1)NC=1OC2=C(N1)C=C(C=C2)O | C[O:1][c:2]1[cH:3][cH:4][c:5]2[o:6][c:7]([NH:8][c:9]3[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]3)[n:16][c:17]2[cH:18]1>>[OH:1][c:2]1[cH:3][cH:4][c:5]2[o:6][c:7]([NH:8][c:9]3[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]3)[n:16][c:17]2[cH:18]1 | COc1ccc2oc(Nc3ccc(Br)cc3)nc2c1 | Oc1ccc2oc(Nc3ccc(Br)cc3)nc2c1 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(Nc2nc3ccccc3o2)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | null | [] | null | null | 6 | MINUTE | The mixture of (4-bromophenyl)(5-methoxybenzoxazol-2-yl)amine and hydrobromic acid (48%) was subjected to the microwave at 150° C. for 6 mins to yield 2-[(4-bromophenyl)amino]benzoxazol-5-ol. MS: MH+=305
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccc2ocnc2c1.c1ccccc1 | Other | null | null | 0.1 | COc1ccc2oc(Nc3ccc(Br)cc3)nc2c1>>Oc1ccc2oc(Nc3ccc(Br)cc3)nc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-045c50a29b284c05a2fc9504042be566 | CNC(=O)c1cc(Cl)ccn1.Oc1ccc2oc(Nc3ccc(Br)cc3)nc2c1>>CNC(=O)c1cc(Oc2ccc3oc(Nc4ccc(Br)cc4)nc3c2)ccn1 | BrC1=CC=C(C=C1)NC=1OC2=C(N1)C=C(C=C2)O.C[Si](C)(C)[N-][Si](C)(C)C.[K+].ClC1=CC(=NC=C1)C(=O)NC.C([O-])([O-])=O.[K+].[K+]>>BrC1=CC=C(C=C1)NC=1OC2=C(N1)C=C(C=C2)OC2=CC(=NC=C2)C(=O)NC | Cl[c:7]1[cH:6][c:5]([C:3]([NH:2][CH3:1])=[O:4])[n:28][cH:27][cH:26]1.[OH:8][c:9]1[cH:10][cH:11][c:12]2[o:13][c:14]([NH:15][c:16]3[cH:17][cH:18][c:19]([Br:20])[cH:21][cH:22]3)[n:23][c:24]2[cH:25]1>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][c:12]3[o:13][c:14]([NH:15][c:16]4[cH:17][cH:18][c:19]... | CNC(=O)c1cc(Cl)ccn1.Oc1ccc2oc(Nc3ccc(Br)cc3)nc2c1 | CNC(=O)c1cc(Oc2ccc3oc(Nc4ccc(Br)cc4)nc3c2)ccn1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 99925b30dd2603ae575cba81b58435d015cd6b7267cf347380904f25833af5f2 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Nc2nc3cc(Oc4ccncc4)ccc3o2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[C:6](-[#7:7])=[O;D1;H0:8]):[c:9]:1.[#7;a:10]:[c:11]:[c:12]:[c:13](-[OH;D1;+0:14]):[c:15]>>[#7:7]-[C:6](=[O;D1;H0:8])-[c:5]1:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:14]-[c:13](:[c:15]):[c:12]:[c:11]:[#7;a:10]):[c:9]:1 | null | [] | null | null | null | null | The mixture containing 2-[(4-bromophenyl)amino]benzoxazol-5-ol (1 eq), potassium bis(trimethylsilyl)amide (4 eq), was stirred in dimethylformamide for 30 min at room temperature. To this mixture was added (4-chloro(2-pyridyl)-N-methyl-carboxamide (1 eq) and Potassium carbonate (1.2 eq) and microwaved for 6 mins at 150°... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccc2ocnc2c1.c1ccccc1 | HCl | CN(C=O)C | null | null | CNC(=O)c1cc(Cl)ccn1.Oc1ccc2oc(Nc3ccc(Br)cc3)nc2c1>CN(C=O)C>CNC(=O)c1cc(Oc2ccc3oc(Nc4ccc(Br)cc4)nc3c2)ccn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4deca450243547aba33d3679d2121b53 | CN(C)c1ccc(Nc2nc3cc(OC4(C(=O)O)C=CC=CN4)ccc3n2C)cc1.NCCN1CCCC1>>CN(C)c1ccc(Nc2nc3cc(OC4(C5CCN(CCNC=O)C5)C=CC=CN4)ccc3n2C)cc1 | CN(C1=CC=C(C=C1)NC1=NC2=C(N1C)C=CC(=C2)OC2(NC=CC=C2)C(=O)O)C.N1(CCCC1)CCN.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=C2)N=N1.F[P-](F)(F)(F)(F)F.C(C)(C)N(C(C)C)CC>>CN(C1=CC=C(C=C1)NC1=NC2=C(N1C)C=CC(=C2)OC2(NC=CC=C2)C2CCN(C2)CCNC=O)C | O[C:23]([C:15]1([O:14][c:13]2[cH:12][c:11]3[n:10][c:9]([NH:8][c:7]4[cH:6][cH:5][c:4]([N:2]([CH3:1])[CH3:3])[cH:37][cH:36]4)[n:34]([CH3:35])[c:33]3[cH:32][cH:31]2)[CH:26]=[CH:27][CH:28]=[CH:29][NH:30]1)=[O:24].[CH2:16]1[CH2:17][CH2:18][N:19]([CH2:20][CH2:21][NH2:22])[CH2:25]1>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7... | CN(C)c1ccc(Nc2nc3cc(OC4(C(=O)O)C=CC=CN4)ccc3n2C)cc1.NCCN1CCCC1 | CN(C)c1ccc(Nc2nc3cc(OC4(C5CCN(CCNC=O)C5)C=CC=CN4)ccc3n2C)cc1 | null | null | O1CCCC1 | Acylation | OtherReaction | a5e50ac5b0783937f71374bd54d64dcd468b1cd9c3c46ff2fd13ac1969cb495f | 25b89026811e1b3313674b1746d98ae7463bb6ef1893abcfeee44f8692f48a05 | C1=CNC(Oc2ccc3[nH]c(Nc4ccccc4)nc3c2)(C2CCNC2)C=C1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D4;+0:3]1(-[#8:4]-[c:5])-[#7:6]-[C:7]=[C:8]-[C:9]=[C:10]-1.[NH2;D1;+0:11]-[C:12]-[C:13]-[#7:14]1-[C:15]-[C:16]-[CH2;D2;+0:17]-[C:18]-1>>[O;D1;H0:2]=[CH;D2;+0:1]-[NH;D2;+0:11]-[C:12]-[C:13]-[#7:14]1-[C:15]-[C:16]-[CH;D3;+0:17](-[C;H0;D4;+0:3]2(-[#8:4]-[c:5])-[#7:6]-[C:7]=[C:8]-[C:9]=... | null | [] | null | null | 16 | HOUR | To 4-(2-{[4-(dimethylamino)pheylamino)-1-methylbenzimidazol-5-yloxy)-pyridine-2-carboxylic acid (1 eq) in tetrahydrofuran was added 2-pyrrolidinylethylamine (2 eq), HBTU (2 eq) and N,N-diisopropylethylamine (4 eq) and stir at ambient temperature for 16 h. The mixture was then concentrated and partitioned between ethyl ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Primary amine | Ether.Secondary amide | C1=CCNC=C1.C1CC[NH]C1 | C1CC[NH]C1.C1=CCNC=C1 | c1ccccc1.c1ccc2nc[nH]c2c1.C1CC[NH]C1.C1=CCNC=C1 | HO- | O1CCCC1 | null | 16 | CN(C)c1ccc(Nc2nc3cc(OC4(C(=O)O)C=CC=CN4)ccc3n2C)cc1.NCCN1CCCC1>O1CCCC1>CN(C)c1ccc(Nc2nc3cc(OC4(C5CCN(CCNC=O)C5)C=CC=CN4)ccc3n2C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cf605cf541c748bcbfd63433e029fcd1 | CNc1ccc(Oc2ccnc(C(=O)OC(C)(C)C)c2)cc1N.Cc1cc(Nc2nc3cc(Oc4ccnc(C(=O)OC(C)(C)C)c4)ccc3n2C)ccc1Br>>Cc1cc(Nc2nc3cc(OC4(C(=O)O)C=CC=CN4)ccc3n2C)ccc1Br | C(C)(C)(C)OC(=O)C1=NC=CC(=C1)OC1=CC2=C(N(C(=N2)NC2=CC(=C(C=C2)Br)C)C)C=C1.C(C)(C)(C)OC(=O)C1=NC=CC(=C1)OC1=CC(=C(C=C1)NC)N.NC(=S)N.FC(C(=O)O)(F)F.IC>>BrC1=C(C=C(C=C1)NC1=NC2=C(N1C)C=CC(=C2)OC2(NC=CC=C2)C(=O)O)C | CNc1ccc(O[c:17]2[cH:16][c:12]([C:13](=[O:14])[O:15]C(C)(C)C)[n:20][cH:19][cH:18]2)cc1N.CC(C)(C)OC(=O)c1cc([O:11][c:10]2[cH:9][c:8]3[n:7][c:6]([NH:5][c:4]4[cH:3][c:2]([CH3:1])[c:28]([Br:29])[cH:27][cH:26]4)[n:24]([CH3:25])[c:23]3[cH:22][cH:21]2)ccn1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][c:8]3[cH:9][c:10]([O:11][C:... | CNc1ccc(Oc2ccnc(C(=O)OC(C)(C)C)c2)cc1N.Cc1cc(Nc2nc3cc(Oc4ccnc(C(=O)OC(C)(C)C)c4)ccc3n2C)ccc1Br | Cc1cc(Nc2nc3cc(OC4(C(=O)O)C=CC=CN4)ccc3n2C)ccc1Br | null | null | C(Cl)Cl.CO | Heteroatom Alkylation and Arylation | OtherReaction | c651282c0e9166458f7bf44c3131d44357e2ab966df1308b03eb64c1632e1461 | 927c5677be0d03bc697f830bd5a0b340e77c09e60abf567ee55f389e8726ded4 | C1=CNC(Oc2ccc3[nH]c(Nc4ccccc4)nc3c2)C=C1 | C-C(-C)(-C)-O-C(=O)-c1:c:c(-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6]):c:c:n:1.C-N-c1:c:c:c(-O-[c;H0;D3;+0:7]2:[cH;D2;+0:8]:[c;H0;D3;+0:9](-[C:10](=[O;D1;H0:11])-[O;H0;D2;+0:12]-C(-C)(-C)-C):[n;H0;D2;+0:13]:[cH;D2;+0:14]:[cH;D2;+0:15]:2):c:c:1-N>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[O;H0;D2;+0:1]-[C;H0;D4;+0:9]1(-[C:10... | null | [] | null | null | 16 | HOUR | To tert-butyl4-[3-amino-4-(methylamino)phenoxy]pyridine-2-carboxylate (1 eq) in methanol was added 4-bromo-3-methylbenzeneisothiocyanate (1 eq) and stir at ambient temperature for 16 h. Formation of the corresponding thiourea was followed by LC/MS. To it was then added iodomethane (1 eq) and heated to 60° C. for 2 h. F... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ether.Ether.Primary amine.Secondary amine.Boc.Boc | Enamine.Carboxylic acid.Ether.Conjugated diene | c1ccccc1.c1ccncc1.c1ccncc1 | C1=CCNC=C1 | c1ccccc1.c1ccc2nc[nH]c2c1.C1=CCNC=C1 | HO- | C(Cl)Cl.CO | null | 16 | CNc1ccc(Oc2ccnc(C(=O)OC(C)(C)C)c2)cc1N.Cc1cc(Nc2nc3cc(Oc4ccnc(C(=O)OC(C)(C)C)c4)ccc3n2C)ccc1Br>C(Cl)Cl.CO>Cc1cc(Nc2nc3cc(OC4(C(=O)O)C=CC=CN4)ccc3n2C)ccc1Br |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2068fbf5dc2e43fc95b2bf9dcc748188 | Cc1cc(Nc2nc3cc(OC4(C(=O)O)C=CC=CN4)ccc3n2C)ccc1Br.NCCN1CCCC1>>Cc1cc(Nc2nc3cc(OC4(C5CCN(CCNC=O)C5)C=CC=CN4)ccc3n2C)ccc1Br | BrC1=C(C=C(C=C1)NC1=NC2=C(N1C)C=CC(=C2)OC2(NC=CC=C2)C(=O)O)C.N1(CCCC1)CCN.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=C2)N=N1.F[P-](F)(F)(F)(F)F.C(C)(C)N(C(C)C)CC>>BrC1=C(C=C(C=C1)NC1=NC2=C(N1C)C=CC(=C2)OC2(NC=CC=C2)C2CCN(C2)CCNC=O)C | O[C:20]([C:12]1([O:11][c:10]2[cH:9][c:8]3[n:7][c:6]([NH:5][c:4]4[cH:3][c:2]([CH3:1])[c:35]([Br:36])[cH:34][cH:33]4)[n:31]([CH3:32])[c:30]3[cH:29][cH:28]2)[CH:23]=[CH:24][CH:25]=[CH:26][NH:27]1)=[O:21].[CH2:13]1[CH2:14][CH2:15][N:16]([CH2:17][CH2:18][NH2:19])[CH2:22]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][c:8]3[cH... | Cc1cc(Nc2nc3cc(OC4(C(=O)O)C=CC=CN4)ccc3n2C)ccc1Br.NCCN1CCCC1 | Cc1cc(Nc2nc3cc(OC4(C5CCN(CCNC=O)C5)C=CC=CN4)ccc3n2C)ccc1Br | null | null | O1CCCC1 | Acylation | OtherReaction | a5e50ac5b0783937f71374bd54d64dcd468b1cd9c3c46ff2fd13ac1969cb495f | 25b89026811e1b3313674b1746d98ae7463bb6ef1893abcfeee44f8692f48a05 | C1=CNC(Oc2ccc3[nH]c(Nc4ccccc4)nc3c2)(C2CCNC2)C=C1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D4;+0:3]1(-[#8:4]-[c:5])-[#7:6]-[C:7]=[C:8]-[C:9]=[C:10]-1.[NH2;D1;+0:11]-[C:12]-[C:13]-[#7:14]1-[C:15]-[C:16]-[CH2;D2;+0:17]-[C:18]-1>>[O;D1;H0:2]=[CH;D2;+0:1]-[NH;D2;+0:11]-[C:12]-[C:13]-[#7:14]1-[C:15]-[C:16]-[CH;D3;+0:17](-[C;H0;D4;+0:3]2(-[#8:4]-[c:5])-[#7:6]-[C:7]=[C:8]-[C:9]=... | null | [] | null | null | 16 | HOUR | To 4-(2-{[4-bromo-3-methylpheylamino)-1-methylbenzimidazol-5-yloxy)-pyridine-2-carboxylic acid(1 eq) in tetrahydrofuran was added 2-pyrrolidinylethylamine (2 eq), HBTU (2 eq) and N,N-diisopropylethylamine (4 eq) and stir at ambient temperature for 16 h. The mixture was then concentrated and partitioned between ethyl ac... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Primary amine | Ether.Secondary amide | C1=CCNC=C1.C1CC[NH]C1 | C1CC[NH]C1.C1=CCNC=C1 | c1ccccc1.c1ccc2nc[nH]c2c1.C1CC[NH]C1.C1=CCNC=C1 | HO- | O1CCCC1 | null | 16 | Cc1cc(Nc2nc3cc(OC4(C(=O)O)C=CC=CN4)ccc3n2C)ccc1Br.NCCN1CCCC1>O1CCCC1>Cc1cc(Nc2nc3cc(OC4(C5CCN(CCNC=O)C5)C=CC=CN4)ccc3n2C)ccc1Br |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-77af987f401e431faa61513a30c385ce | CNc1ccc(Oc2ccnc(C(=O)OC(C)(C)C)c2)cc1N.Cn1c(Nc2cc(C(F)(F)F)ccc2F)nc2cc(Oc3ccnc(C(=O)OC(C)(C)C)c3)ccc21.NC(N)=S>>Cn1c(Nc2cc(C(F)(F)F)ccc2F)nc2cc(OC3(C(=O)O)C=CC=CN3)ccc21 | C(C)(C)(C)OC(=O)C1=NC=CC(=C1)OC1=CC2=C(N(C(=N2)NC2=C(C=CC(=C2)C(F)(F)F)F)C)C=C1.C(C)(C)(C)OC(=O)C1=NC=CC(=C1)OC1=CC(=C(C=C1)NC)N.NC(=S)N.FC(C(=O)O)(F)F.IC>>FC1=C(C=C(C=C1)C(F)(F)F)NC1=NC2=C(N1C)C=CC(=C2)OC2(NC=CC=C2)C(=O)O | CNc1ccc(Oc2ccnc([C:22](=[O:23])[O:24]C(C)(C)C)c2)cc1N.CC(C)(C)OC(=O)[c:26]1n[cH:28][cH:27][c:21]([O:20][c:19]2[cH:18][c:17]3[n:16][c:3]([NH:4][c:5]4[cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[cH:12][cH:13][c:14]4[F:15])[n:2]([CH3:1])[c:32]3[cH:31][cH:30]2)[cH:25]1.NC(=S)[NH2:29]>>[CH3:1][n:2]1[c:3]([NH:4][c:5]2[cH:6][c:7](... | CNc1ccc(Oc2ccnc(C(=O)OC(C)(C)C)c2)cc1N.Cn1c(Nc2cc(C(F)(F)F)ccc2F)nc2cc(Oc3ccnc(C(=O)OC(C)(C)C)c3)ccc21.NC(N)=S | Cn1c(Nc2cc(C(F)(F)F)ccc2F)nc2cc(OC3(C(=O)O)C=CC=CN3)ccc21 | null | null | C(Cl)Cl.CO | C-C Coupling | OtherReaction | aea9c54fe4921815ac01c46586f27cf72b719e60f75bcb23786d01b4869c9824 | 67ed9599112c34fcf96cf445349b3d87559530f619170487474df0344ae446d4 | C1=CNC(Oc2ccc3[nH]c(Nc4ccccc4)nc3c2)C=C1 | C-C(-C)(-C)-O-C(=O)-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[c;H0;D3;+0:3](-[#8:4]-[c:5]):[cH;D2;+0:6]:[cH;D2;+0:7]:n:1.C-N-c1:c:c:c(-O-c2:c:c:n:c(-[C;H0;D3;+0:8](=[O;D1;H0:9])-[O;H0;D2;+0:10]-C(-C)(-C)-C):c:2):c:c:1-N.N-C(=S)-[NH2;D1;+0:11]>>[O;D1;H0:9]=[C;H0;D3;+0:8](-[OH;D1;+0:10])-[C;H0;D4;+0:3]1(-[#8:4]-[c:5])-[CH;D2;+0:2]=[... | null | [] | null | null | 16 | HOUR | To tert-butyl4-[3-amino-4-(methylamino)phenoxy]pyridine-2-carboxylate (1 eq) in methanol was added 2-fluro-5-(trifluromethyl)benzeneisothiocyanate (1 eq) and stir at ambient temperature for 16 h. Formation of the corresponding thiourea was followed by LC/MS. To it was then added iodomethane (1 eq) and heated to 60° C. ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ether.Ether.Thiourea.Primary amine.Secondary amine.Boc.Boc | Enamine.Carboxylic acid.Ether.Conjugated diene | c1ccccc1.c1ccncc1.c1ccncc1 | C1=CCNC=C1 | c1ccccc1.c1ccc2[nH]cnc2c1.C1=CCNC=C1 | Other | C(Cl)Cl.CO | null | 16 | CNc1ccc(Oc2ccnc(C(=O)OC(C)(C)C)c2)cc1N.Cn1c(Nc2cc(C(F)(F)F)ccc2F)nc2cc(Oc3ccnc(C(=O)OC(C)(C)C)c3)ccc21.NC(N)=S>C(Cl)Cl.CO>Cn1c(Nc2cc(C(F)(F)F)ccc2F)nc2cc(OC3(C(=O)O)C=CC=CN3)ccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c3fb996c828a4d13bda2ab66d028f62d | Cn1c(Nc2cc(C(F)(F)F)ccc2F)nc2cc(OC3(C(=O)O)C=CC=CN3)ccc21.NCCN1CCCC1>>Cn1c(Nc2cc(C(F)(F)F)ccc2F)nc2cc(OC3(C4CCN(CCNC=O)C4)C=CC=CN3)ccc21 | FC1=C(C=C(C=C1)C(F)(F)F)NC1=NC2=C(N1C)C=CC(=C2)OC2(NC=CC=C2)C(=O)O.N1(CCCC1)CCN.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=C2)N=N1.F[P-](F)(F)(F)(F)F.C(C)(C)N(C(C)C)CC>>FC1=C(C=C(C=C1)C(F)(F)F)NC1=NC2=C(N1C)C=CC(=C2)OC2(NC=CC=C2)C2CCN(C2)CCNC=O | O[C:29]([C:21]1([O:20][c:19]2[cH:18][c:17]3[n:16][c:3]([NH:4][c:5]4[cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[cH:12][cH:13][c:14]4[F:15])[n:2]([CH3:1])[c:39]3[cH:38][cH:37]2)[CH:32]=[CH:33][CH:34]=[CH:35][NH:36]1)=[O:30].[CH2:22]1[CH2:23][CH2:24][N:25]([CH2:26][CH2:27][NH2:28])[CH2:31]1>>[CH3:1][n:2]1[c:3]([NH:4][c:5]2[cH... | Cn1c(Nc2cc(C(F)(F)F)ccc2F)nc2cc(OC3(C(=O)O)C=CC=CN3)ccc21.NCCN1CCCC1 | Cn1c(Nc2cc(C(F)(F)F)ccc2F)nc2cc(OC3(C4CCN(CCNC=O)C4)C=CC=CN3)ccc21 | null | null | O1CCCC1 | Acylation | OtherReaction | a5e50ac5b0783937f71374bd54d64dcd468b1cd9c3c46ff2fd13ac1969cb495f | 25b89026811e1b3313674b1746d98ae7463bb6ef1893abcfeee44f8692f48a05 | C1=CNC(Oc2ccc3[nH]c(Nc4ccccc4)nc3c2)(C2CCNC2)C=C1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D4;+0:3]1(-[#8:4]-[c:5])-[#7:6]-[C:7]=[C:8]-[C:9]=[C:10]-1.[NH2;D1;+0:11]-[C:12]-[C:13]-[#7:14]1-[C:15]-[C:16]-[CH2;D2;+0:17]-[C:18]-1>>[O;D1;H0:2]=[CH;D2;+0:1]-[NH;D2;+0:11]-[C:12]-[C:13]-[#7:14]1-[C:15]-[C:16]-[CH;D3;+0:17](-[C;H0;D4;+0:3]2(-[#8:4]-[c:5])-[#7:6]-[C:7]=[C:8]-[C:9]=... | null | [] | null | null | 16 | HOUR | To 4-(2-{[2-fluro-5-(trifluromethyl)phenylamino)-1-methylbenzimidazol-5-yl-oxy)pyridine-2-carboxylic acid (1 eq) in tetrahydrofuran was added 2-pyrrolidinylethylamine (2 eq), HBTU (2 eq) and N,N-diisopropylethylamine (4 eq) and stir at ambient temperature for 16 h. The mixture was then concentrated and partitioned betw... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Primary amine | Ether.Secondary amide | C1=CCNC=C1.C1CC[NH]C1 | C1CC[NH]C1.C1=CCNC=C1 | c1ccccc1.c1ccc2[nH]cnc2c1.C1CC[NH]C1.C1=CCNC=C1 | HO- | O1CCCC1 | null | 16 | Cn1c(Nc2cc(C(F)(F)F)ccc2F)nc2cc(OC3(C(=O)O)C=CC=CN3)ccc21.NCCN1CCCC1>O1CCCC1>Cn1c(Nc2cc(C(F)(F)F)ccc2F)nc2cc(OC3(C4CCN(CCNC=O)C4)C=CC=CN3)ccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5e06cd34c97e405ab21ba84324b39d71 | CNc1ccc(Oc2ccnc(C(=O)OC(C)(C)C)c2)cc1N.Cn1c(Nc2ccc(Br)c(F)c2)nc2cc(Oc3ccnc(C(=O)OC(C)(C)C)c3)ccc21>>Cn1c(Nc2ccc(Br)c(F)c2)nc2cc(OC3(C(=O)O)C=CC=CN3)ccc21 | C(C)(C)(C)OC(=O)C1=NC=CC(=C1)OC1=CC2=C(N(C(=N2)NC2=CC(=C(C=C2)Br)F)C)C=C1.C(C)(C)(C)OC(=O)C1=NC=CC(=C1)OC1=CC(=C(C=C1)NC)N.NC(=S)N.FC(C(=O)O)(F)F.IC>>BrC1=C(C=C(C=C1)NC1=NC2=C(N1C)C=CC(=C2)OC2(NC=CC=C2)C(=O)O)F | CNc1ccc(Oc2cc([C:19](=[O:20])[O:21]C(C)(C)C)[n:26][cH:25][cH:24]2)cc1N.CC(C)(C)OC(=O)[c:23]1ncc[c:18]([O:17][c:16]2[cH:15][c:14]3[n:13][c:3]([NH:4][c:5]4[cH:6][cH:7][c:8]([Br:9])[c:10]([F:11])[cH:12]4)[n:2]([CH3:1])[c:29]3[cH:28][cH:27]2)[cH:22]1>>[CH3:1][n:2]1[c:3]([NH:4][c:5]2[cH:6][cH:7][c:8]([Br:9])[c:10]([F:11])[c... | CNc1ccc(Oc2ccnc(C(=O)OC(C)(C)C)c2)cc1N.Cn1c(Nc2ccc(Br)c(F)c2)nc2cc(Oc3ccnc(C(=O)OC(C)(C)C)c3)ccc21 | Cn1c(Nc2ccc(Br)c(F)c2)nc2cc(OC3(C(=O)O)C=CC=CN3)ccc21 | null | null | C(Cl)Cl.CO | C-C Coupling | OtherReaction | 69f76c3b8a2300e5b27a5f67d2c164aa6431c7e55762dde8b548912e55721d5b | 4edbc5aa10c177b20f61383c702da22155b87866fa39db7fef23ed8b6baa10fc | C1=CNC(Oc2ccc3[nH]c(Nc4ccccc4)nc3c2)C=C1 | C-C(-C)(-C)-O-C(=O)-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[c;H0;D3;+0:3](-[#8:4]-[c:5]):c:c:n:1.C-N-c1:c:c:c(-O-c2:[cH;D2;+0:6]:[cH;D2;+0:7]:[n;H0;D2;+0:8]:c(-[C;H0;D3;+0:9](=[O;D1;H0:10])-[O;H0;D2;+0:11]-C(-C)(-C)-C):c:2):c:c:1-N>>[O;D1;H0:10]=[C;H0;D3;+0:9](-[OH;D1;+0:11])-[C;H0;D4;+0:3]1(-[#8:4]-[c:5])-[CH;D2;+0:2]=[CH;D2;+0... | null | [] | null | null | 16 | HOUR | To tert-butyl4-[3-amino-4-(methylamino)phenoxy]pyridine-2-carboxylate (1 eq) in methanol was added 4-bromo-3-flurobenzeneisothiocyanate (1 eq) and stir at ambient temperature for 16 h. Formation of the corresponding thiourea was followed by LC/MS. To it was then added iodomethane (1 eq) and heated to 60° C. for 2 h. Fo... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ether.Ether.Primary amine.Secondary amine.Boc.Boc | Enamine.Carboxylic acid.Ether.Conjugated diene | c1ccccc1.c1ccncc1.c1ccncc1 | C1=CCNC=C1 | c1ccccc1.c1ccc2[nH]cnc2c1.C1=CCNC=C1 | HO- | C(Cl)Cl.CO | null | 16 | CNc1ccc(Oc2ccnc(C(=O)OC(C)(C)C)c2)cc1N.Cn1c(Nc2ccc(Br)c(F)c2)nc2cc(Oc3ccnc(C(=O)OC(C)(C)C)c3)ccc21>C(Cl)Cl.CO>Cn1c(Nc2ccc(Br)c(F)c2)nc2cc(OC3(C(=O)O)C=CC=CN3)ccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-091680e93d774347987231f23e16a93f | Cn1c(Nc2ccc(Br)c(F)c2)nc2cc(OC3(C(=O)O)C=CC=CN3)ccc21.NCCC1CCCCN1>>Cn1c(Nc2ccc(Br)c(F)c2)nc2cc(OC3(C4CCNC(CCNC=O)C4)C=CC=CN3)ccc21 | BrC1=C(C=C(C=C1)NC1=NC2=C(N1C)C=CC(=C2)OC2(NC=CC=C2)C(=O)O)F.N1C(CCCC1)CCN.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=C2)N=N1.F[P-](F)(F)(F)(F)F.C(C)(C)N(C(C)C)CC>>BrC1=C(C=C(C=C1)NC1=NC2=C(N1C)C=CC(=C2)OC2(NC=CC=C2)C2CC(NCC2)CCNC=O)F | O[C:27]([C:18]1([O:17][c:16]2[cH:15][c:14]3[n:13][c:3]([NH:4][c:5]4[cH:6][cH:7][c:8]([Br:9])[c:10]([F:11])[cH:12]4)[n:2]([CH3:1])[c:37]3[cH:36][cH:35]2)[CH:30]=[CH:31][CH:32]=[CH:33][NH:34]1)=[O:28].[CH2:19]1[CH2:20][CH2:21][NH:22][CH:23]([CH2:24][CH2:25][NH2:26])[CH2:29]1>>[CH3:1][n:2]1[c:3]([NH:4][c:5]2[cH:6][cH:7][c... | Cn1c(Nc2ccc(Br)c(F)c2)nc2cc(OC3(C(=O)O)C=CC=CN3)ccc21.NCCC1CCCCN1 | Cn1c(Nc2ccc(Br)c(F)c2)nc2cc(OC3(C4CCNC(CCNC=O)C4)C=CC=CN3)ccc21 | null | null | O1CCCC1 | Acylation | OtherReaction | bf1a936de3976a9cfd7abaadcadfdba07ae9915b3d8a8e69219619eaa53c3590 | 25b89026811e1b3313674b1746d98ae7463bb6ef1893abcfeee44f8692f48a05 | C1=CNC(Oc2ccc3[nH]c(Nc4ccccc4)nc3c2)(C2CCNCC2)C=C1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D4;+0:3]1(-[#8:4]-[c:5])-[#7:6]-[C:7]=[C:8]-[C:9]=[C:10]-1.[NH2;D1;+0:11]-[C:12]-[C:13]-[C:14]1-[#7:15]-[C:16]-[C:17]-[CH2;D2;+0:18]-[C:19]-1>>[O;D1;H0:2]=[CH;D2;+0:1]-[NH;D2;+0:11]-[C:12]-[C:13]-[C:14]1-[#7:15]-[C:16]-[C:17]-[CH;D3;+0:18](-[C;H0;D4;+0:3]2(-[#8:4]-[c:5])-[#7:6]-[C:7... | null | [] | null | null | 16 | HOUR | To 4-(2-{[4-bromo-3-fluropheylamino)-1-methylbenzimidazol-5-yloxy)pyridine-2-carboxylic acid (1 eq) in tetrahydrofuran was added 2-piperidylethylamine (2 eq), HBTU (2 eq) and N,N-diisopropylethylamine (4 eq) and stir at ambient temperature for 16 h. The mixture was then concentrated and partitioned between ethyl acetat... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Primary amine | Ether.Secondary amide | C1=CCNC=C1.C1CCNCC1 | C1CCNCC1.C1=CCNC=C1 | c1ccccc1.c1ccc2[nH]cnc2c1.C1CCNCC1.C1=CCNC=C1 | HO- | O1CCCC1 | null | 16 | Cn1c(Nc2ccc(Br)c(F)c2)nc2cc(OC3(C(=O)O)C=CC=CN3)ccc21.NCCC1CCCCN1>O1CCCC1>Cn1c(Nc2ccc(Br)c(F)c2)nc2cc(OC3(C4CCNC(CCNC=O)C4)C=CC=CN3)ccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e34ada74913c4bee92a02dcdd4f03e69 | CCc1ccc(Nc2nc3cc(Oc4ccnc(C(=O)OC(C)(C)C)c4)ccc3n2C)cc1>>CCc1ccc(Nc2nc3cc(OC4(C(=O)O)C=CC=CN4)ccc3n2C)cc1 | C(C)(C)(C)OC(=O)C1=NC=CC(=C1)OC1=CC2=C(N(C(=N2)NC2=CC=C(C=C2)CC)C)C=C1.C(C)(C)(C)OC(=O)C1=NC=CC(=C1)OC1=CC(=C(C=C1)NC)N.NC(=S)N.FC(C(=O)O)(F)F.IC>>C(C)C1=CC=C(C=C1)NC1=NC2=C(N1C)C=CC(=C2)OC2(NC=CC=C2)C(=O)O | CC(C)(C)[O:17][C:15]([c:14]1[cH:18][c:19]([O:13][c:12]2[cH:11][c:10]3[n:9][c:8]([NH:7][c:6]4[cH:5][cH:4][c:3]([CH2:2][CH3:1])[cH:29][cH:28]4)[n:26]([CH3:27])[c:25]3[cH:24][cH:23]2)[cH:20][cH:21][n:22]1)=[O:16]>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][c:10]3[cH:11][c:12]([O:13][C:14]4([C:15](=[O:16])[OH:... | CCc1ccc(Nc2nc3cc(Oc4ccnc(C(=O)OC(C)(C)C)c4)ccc3n2C)cc1 | CCc1ccc(Nc2nc3cc(OC4(C(=O)O)C=CC=CN4)ccc3n2C)cc1 | null | null | C(Cl)Cl.CO | Reduction | OtherReaction | d3267c8cc68d2a5b89c3e6e8fab69387f9d7531c9843a66c036bcfaf2a30fb80 | 7af9e23356bd0e70bec1bc13ad619ccc3e02b9df9ac8a03ecfeb09c23c86c19e | C1=CNC(Oc2ccc3[nH]c(Nc4ccccc4)nc3c2)C=C1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c;H0;D3;+0:4]1:[cH;D2;+0:5]:[c;H0;D3;+0:6](-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]:[c:11]:[#7;a:12]):[cH;D2;+0:13]:[cH;D2;+0:14]:[n;H0;D2;+0:15]:1>>[#7;a:12]:[c:11]:[c:10]:[c:8](-[O;H0;D2;+0:7]-[C;H0;D4;+0:4]1(-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1])-[CH;D2;+0:5]=[CH;D2;+0:6]-[CH;... | null | [] | null | null | 16 | HOUR | To tert-butyl4-[3-amino-4-(methylamino)phenoxy]pyridine-2-carboxylate (1 eq) in methanol was added 4-ethylbenzeneisothiocyanate (1 eq) and stir at ambient temperature for 16 h. Formation of the corresponding thiourea was followed by LC/MS. To it was then added iodomethane (1 eq) and heated to 60° C. for 2 h. Formation ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Boc | Enamine.Carboxylic acid.Ether.Conjugated diene | c1ccncc1 | C1=CCNC=C1 | c1ccccc1.c1ccc2nc[nH]c2c1.C1=CCNC=C1 | Other | C(Cl)Cl.CO | null | 16 | CCc1ccc(Nc2nc3cc(Oc4ccnc(C(=O)OC(C)(C)C)c4)ccc3n2C)cc1>C(Cl)Cl.CO>CCc1ccc(Nc2nc3cc(OC4(C(=O)O)C=CC=CN4)ccc3n2C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6fb29f1c20dc42d685c70611cd0567a6 | CCc1ccc(Nc2nc3cc(Oc4ccnc(C(=O)O)c4)ccc3n2C)cc1.NCCN1CCCC1>>CCc1ccc(Nc2nc3cc(OC4(C5CCN(CCNC=O)C5)C=CC=CN4)ccc3n2C)cc1 | C(C)C1=CC=C(C=C1)NC1=NC2=C(N1C)C=CC(=C2)OC2=CC(=NC=C2)C(=O)O.N1(CCCC1)CCN.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=C2)N=N1.F[P-](F)(F)(F)(F)F.C(C)(C)N(C(C)C)CC>>C(C)C1=CC=C(C=C1)NC1=NC2=C(N1C)C=CC(=C2)OC2(NC=CC=C2)C2CCN(C2)CCNC=O | O[C:22](=[O:23])[c:26]1[cH:25][c:14]([O:13][c:12]2[cH:11][c:10]3[n:9][c:8]([NH:7][c:6]4[cH:5][cH:4][c:3]([CH2:2][CH3:1])[cH:36][cH:35]4)[n:33]([CH3:34])[c:32]3[cH:31][cH:30]2)[cH:27][cH:28][n:29]1.[CH2:15]1[CH2:16][CH2:17][N:18]([CH2:19][CH2:20][NH2:21])[CH2:24]1>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[n:9]... | CCc1ccc(Nc2nc3cc(Oc4ccnc(C(=O)O)c4)ccc3n2C)cc1.NCCN1CCCC1 | CCc1ccc(Nc2nc3cc(OC4(C5CCN(CCNC=O)C5)C=CC=CN4)ccc3n2C)cc1 | null | null | O1CCCC1 | Acylation | OtherReaction | 43c7c99d7b02bd3a4807c6f78ebd3df0228169d9aeb5e4dde71257220982421b | 1deae815888eed473c5335f3c03e53789c06dcbb831fcceb524365d2bc97aa94 | C1=CNC(Oc2ccc3[nH]c(Nc4ccccc4)nc3c2)(C2CCNC2)C=C1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[#8:6]-[c:7]):[cH;D2;+0:8]:[cH;D2;+0:9]:[n;H0;D2;+0:10]:1.[NH2;D1;+0:11]-[C:12]-[C:13]-[#7:14]1-[C:15]-[C:16]-[CH2;D2;+0:17]-[C:18]-1>>[O;D1;H0:2]=[CH;D2;+0:1]-[NH;D2;+0:11]-[C:12]-[C:13]-[#7:14]1-[C:15]-[C:16]-[CH;D3;+0:17](-[C;H0;D4;+0:5]2(-[... | null | [] | null | null | 16 | HOUR | To 4-(2-{[4-ethylpheyl]amino)-1-methylbenzimidazol-5-yloxy)pyridine-2-carboxylic acid (1 eq) in tetrahydrofuran was added 2-pyrrolidinylethylamine (2 eq), HBTU (2 eq) and N,N-diisopropylethylamine (4 eq) and stir at ambient temperature for 16 h. The mixture was then concentrated and partitioned between ethyl acetate an... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Primary amine | Enamine.Ether.Secondary amide.Conjugated diene | c1ccncc1.C1CC[NH]C1 | C1CC[NH]C1.C1=CCNC=C1 | c1ccccc1.c1ccc2nc[nH]c2c1.C1CC[NH]C1.C1=CCNC=C1 | Other | O1CCCC1 | null | 16 | CCc1ccc(Nc2nc3cc(Oc4ccnc(C(=O)O)c4)ccc3n2C)cc1.NCCN1CCCC1>O1CCCC1>CCc1ccc(Nc2nc3cc(OC4(C5CCN(CCNC=O)C5)C=CC=CN4)ccc3n2C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e07ae407e2ad4211b517156c3f50540b | CNc1ccc(Oc2ccnc(C(=O)OC(C)(C)C)c2)cc1N.Cn1c(Nc2cccc(C(C)(C)C)c2)nc2cc(Oc3ccnc(C(=O)OC(C)(C)C)c3)ccc21>>Cn1c(Nc2cccc(C(C)(C)C)c2)nc2cc(OC3(C(=O)O)C=CC=CN3)ccc21 | C(C)(C)(C)OC(=O)C1=NC=CC(=C1)OC1=CC2=C(N(C(=N2)NC2=CC(=CC=C2)C(C)(C)C)C)C=C1.C(C)(C)(C)OC(=O)C1=NC=CC(=C1)OC1=CC(=C(C=C1)NC)N.NC(=S)N.FC(C(=O)O)(F)F.IC>>C(C)(C)(C)C=1C=C(C=CC1)NC1=NC2=C(N1C)C=CC(=C2)OC2(NC=CC=C2)C(=O)O | CNc1ccc(Oc2cc([C:21](=[O:22])[O:23]C(C)(C)C)[n:28][cH:27][cH:26]2)cc1N.CC(C)(C)OC(=O)[c:25]1ncc[c:20]([O:19][c:18]2[cH:17][c:16]3[n:15][c:3]([NH:4][c:5]4[cH:6][cH:7][cH:8][c:9]([C:10]([CH3:11])([CH3:12])[CH3:13])[cH:14]4)[n:2]([CH3:1])[c:31]3[cH:30][cH:29]2)[cH:24]1>>[CH3:1][n:2]1[c:3]([NH:4][c:5]2[cH:6][cH:7][cH:8][c:... | CNc1ccc(Oc2ccnc(C(=O)OC(C)(C)C)c2)cc1N.Cn1c(Nc2cccc(C(C)(C)C)c2)nc2cc(Oc3ccnc(C(=O)OC(C)(C)C)c3)ccc21 | Cn1c(Nc2cccc(C(C)(C)C)c2)nc2cc(OC3(C(=O)O)C=CC=CN3)ccc21 | null | null | C(Cl)Cl.CO | C-C Coupling | OtherReaction | 69f76c3b8a2300e5b27a5f67d2c164aa6431c7e55762dde8b548912e55721d5b | 4edbc5aa10c177b20f61383c702da22155b87866fa39db7fef23ed8b6baa10fc | C1=CNC(Oc2ccc3[nH]c(Nc4ccccc4)nc3c2)C=C1 | C-C(-C)(-C)-O-C(=O)-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[c;H0;D3;+0:3](-[#8:4]-[c:5]):c:c:n:1.C-N-c1:c:c:c(-O-c2:[cH;D2;+0:6]:[cH;D2;+0:7]:[n;H0;D2;+0:8]:c(-[C;H0;D3;+0:9](=[O;D1;H0:10])-[O;H0;D2;+0:11]-C(-C)(-C)-C):c:2):c:c:1-N>>[O;D1;H0:10]=[C;H0;D3;+0:9](-[OH;D1;+0:11])-[C;H0;D4;+0:3]1(-[#8:4]-[c:5])-[CH;D2;+0:2]=[CH;D2;+0... | null | [] | null | null | 16 | HOUR | To tert-butyl4-[3-amino-4-(methylamino)phenoxy]pyridine-2-carboxylate (1 eq) in methanol was added 3-(tert-butyl)benzeneisothiocyanate (1 eq) and stir at ambient temperature for 16 h. Formation of the corresponding thiourea was followed by LC/MS. To it was then added iodomethane (1 eq) and heated to 60° C. for 2 h. For... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ether.Ether.Primary amine.Secondary amine.Boc.Boc | Enamine.Carboxylic acid.Ether.Conjugated diene | c1ccccc1.c1ccncc1.c1ccncc1 | C1=CCNC=C1 | c1ccccc1.c1ccc2[nH]cnc2c1.C1=CCNC=C1 | HO- | C(Cl)Cl.CO | null | 16 | CNc1ccc(Oc2ccnc(C(=O)OC(C)(C)C)c2)cc1N.Cn1c(Nc2cccc(C(C)(C)C)c2)nc2cc(Oc3ccnc(C(=O)OC(C)(C)C)c3)ccc21>C(Cl)Cl.CO>Cn1c(Nc2cccc(C(C)(C)C)c2)nc2cc(OC3(C(=O)O)C=CC=CN3)ccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-31884a28b2674f72abfb5151acc15a1a | Cn1c(Nc2cccc(C(C)(C)C)c2)nc2cc(OC3(C(=O)O)C=CC=CN3)ccc21.NCCC1CCCCN1>>Cn1c(Nc2cccc(C(C)(C)C)c2)nc2cc(OC3(C4CCNC(CCNC=O)C4)C=CC=CN3)ccc21 | C(C)(C)(C)C=1C=C(C=CC1)NC1=NC2=C(N1C)C=CC(=C2)OC2(NC=CC=C2)C(=O)O.N1C(CCCC1)CCN.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=C2)N=N1.F[P-](F)(F)(F)(F)F.C(C)(C)N(C(C)C)CC>>C(C)(C)(C)C=1C=C(C=CC1)NC1=NC2=C(N1C)C=CC(=C2)OC2(NC=CC=C2)C2CC(NCC2)CCNC=O | O[C:29]([C:20]1([O:19][c:18]2[cH:17][c:16]3[n:15][c:3]([NH:4][c:5]4[cH:6][cH:7][cH:8][c:9]([C:10]([CH3:11])([CH3:12])[CH3:13])[cH:14]4)[n:2]([CH3:1])[c:39]3[cH:38][cH:37]2)[CH:32]=[CH:33][CH:34]=[CH:35][NH:36]1)=[O:30].[CH2:21]1[CH2:22][CH2:23][NH:24][CH:25]([CH2:26][CH2:27][NH2:28])[CH2:31]1>>[CH3:1][n:2]1[c:3]([NH:4]... | Cn1c(Nc2cccc(C(C)(C)C)c2)nc2cc(OC3(C(=O)O)C=CC=CN3)ccc21.NCCC1CCCCN1 | Cn1c(Nc2cccc(C(C)(C)C)c2)nc2cc(OC3(C4CCNC(CCNC=O)C4)C=CC=CN3)ccc21 | null | null | O1CCCC1 | Acylation | OtherReaction | bf1a936de3976a9cfd7abaadcadfdba07ae9915b3d8a8e69219619eaa53c3590 | 25b89026811e1b3313674b1746d98ae7463bb6ef1893abcfeee44f8692f48a05 | C1=CNC(Oc2ccc3[nH]c(Nc4ccccc4)nc3c2)(C2CCNCC2)C=C1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D4;+0:3]1(-[#8:4]-[c:5])-[#7:6]-[C:7]=[C:8]-[C:9]=[C:10]-1.[NH2;D1;+0:11]-[C:12]-[C:13]-[C:14]1-[#7:15]-[C:16]-[C:17]-[CH2;D2;+0:18]-[C:19]-1>>[O;D1;H0:2]=[CH;D2;+0:1]-[NH;D2;+0:11]-[C:12]-[C:13]-[C:14]1-[#7:15]-[C:16]-[C:17]-[CH;D3;+0:18](-[C;H0;D4;+0:3]2(-[#8:4]-[c:5])-[#7:6]-[C:7... | null | [] | null | null | 16 | HOUR | To 4-(2-{[3-(tert-butyl)phenylamino)-1-methylbenzimidazol-5-yloxy)pyridine-2-carboxylic acid (1 eq) in tetrahydrofuran was added 2-piperidylethylamine (2 eq), HBTU (2 eq) and N,N-diisopropylethylamine (4 eq) and stir at ambient temperature for 16 h. The mixture was then concentrated and partitioned between ethyl acetat... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Primary amine | Ether.Secondary amide | C1=CCNC=C1.C1CCNCC1 | C1CCNCC1.C1=CCNC=C1 | c1ccccc1.c1ccc2[nH]cnc2c1.C1CCNCC1.C1=CCNC=C1 | HO- | O1CCCC1 | null | 16 | Cn1c(Nc2cccc(C(C)(C)C)c2)nc2cc(OC3(C(=O)O)C=CC=CN3)ccc21.NCCC1CCCCN1>O1CCCC1>Cn1c(Nc2cccc(C(C)(C)C)c2)nc2cc(OC3(C4CCNC(CCNC=O)C4)C=CC=CN3)ccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c8ae1da528ce40c6b1958b78eb9caaca | CNc1ccc(Oc2ccnc(C(=O)OC(C)(C)C)c2)cc1N.Cn1c(Nc2ccc(Cl)c(C(F)(F)F)c2)nc2cc(Oc3ccnc(C(=O)OC(C)(C)C)c3)ccc21>>Cn1c(Nc2ccc(Cl)c(C(F)(F)F)c2)nc2cc(OC3(C(=O)O)C=CC=CN3)ccc21 | C(C)(C)(C)OC(=O)C1=NC=CC(=C1)OC1=CC2=C(N(C(=N2)NC2=CC(=C(C=C2)Cl)C(F)(F)F)C)C=C1.C(C)(C)(C)OC(=O)C1=NC=CC(=C1)OC1=CC(=C(C=C1)NC)N.NC(=S)N.FC(C(=O)O)(F)F.IC>>ClC1=C(C=C(C=C1)NC1=NC2=C(N1C)C=CC(=C2)OC2(NC=CC=C2)C(=O)O)C(F)(F)F | CNc1ccc(Oc2cc([C:22](=[O:23])[O:24]C(C)(C)C)[n:29][cH:28][cH:27]2)cc1N.CC(C)(C)OC(=O)[c:26]1ncc[c:21]([O:20][c:19]2[cH:18][c:17]3[n:16][c:3]([NH:4][c:5]4[cH:6][cH:7][c:8]([Cl:9])[c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]4)[n:2]([CH3:1])[c:32]3[cH:31][cH:30]2)[cH:25]1>>[CH3:1][n:2]1[c:3]([NH:4][c:5]2[cH:6][cH:7][c:8]([... | CNc1ccc(Oc2ccnc(C(=O)OC(C)(C)C)c2)cc1N.Cn1c(Nc2ccc(Cl)c(C(F)(F)F)c2)nc2cc(Oc3ccnc(C(=O)OC(C)(C)C)c3)ccc21 | Cn1c(Nc2ccc(Cl)c(C(F)(F)F)c2)nc2cc(OC3(C(=O)O)C=CC=CN3)ccc21 | null | null | C(Cl)Cl.CO | C-C Coupling | OtherReaction | 69f76c3b8a2300e5b27a5f67d2c164aa6431c7e55762dde8b548912e55721d5b | 4edbc5aa10c177b20f61383c702da22155b87866fa39db7fef23ed8b6baa10fc | C1=CNC(Oc2ccc3[nH]c(Nc4ccccc4)nc3c2)C=C1 | C-C(-C)(-C)-O-C(=O)-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[c;H0;D3;+0:3](-[#8:4]-[c:5]):c:c:n:1.C-N-c1:c:c:c(-O-c2:[cH;D2;+0:6]:[cH;D2;+0:7]:[n;H0;D2;+0:8]:c(-[C;H0;D3;+0:9](=[O;D1;H0:10])-[O;H0;D2;+0:11]-C(-C)(-C)-C):c:2):c:c:1-N>>[O;D1;H0:10]=[C;H0;D3;+0:9](-[OH;D1;+0:11])-[C;H0;D4;+0:3]1(-[#8:4]-[c:5])-[CH;D2;+0:2]=[CH;D2;+0... | null | [] | null | null | 16 | HOUR | To tert-butyl4-[3-amino-4-(methylamino)phenoxy]pyridine-2-carboxylate (1 eq) in methanol was added 4-chloro-3-(trifluromethyl)benzeneisothiocyanate (1 eq) and stir at ambient temperature for 16 h. Formation of the corresponding thiourea was followed by LC/MS. To it was then added iodomethane (1 eq) and heated to 60° C.... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ether.Ether.Primary amine.Secondary amine.Boc.Boc | Enamine.Carboxylic acid.Ether.Conjugated diene | c1ccccc1.c1ccncc1.c1ccncc1 | C1=CCNC=C1 | c1ccccc1.c1ccc2[nH]cnc2c1.C1=CCNC=C1 | HO- | C(Cl)Cl.CO | null | 16 | CNc1ccc(Oc2ccnc(C(=O)OC(C)(C)C)c2)cc1N.Cn1c(Nc2ccc(Cl)c(C(F)(F)F)c2)nc2cc(Oc3ccnc(C(=O)OC(C)(C)C)c3)ccc21>C(Cl)Cl.CO>Cn1c(Nc2ccc(Cl)c(C(F)(F)F)c2)nc2cc(OC3(C(=O)O)C=CC=CN3)ccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0a79efa2b0854b679e5635cea251931d | CNC(=O)c1cc(Oc2ccc(NC)c(N)c2)ccn1.O=C(Cl)c1ccc(CCl)cc1>>CNC(=O)c1cc(Oc2ccc3c(c2)nc(NC(=O)c2ccc(CCl)cc2)n3C)ccn1 | [S-]C#N.[Na+].ClCC1=CC=C(C(=O)Cl)C=C1.NC=1C=C(OC2=CC(=NC=C2)C(=O)NC)C=CC1NC.Cl.C(C)N=C=NCCCN(C)C>>ClCC1=CC=C(C=C1)C(=O)NC1=NC2=C(N1C)C=CC(=C2)OC2=CC(=NC=C2)C(=O)NC | [CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][c:12]([NH:28][CH3:29])[c:13]([NH2:15])[cH:14]2)[cH:30][cH:31][n:32]1.Cl[C:18](=[O:19])[c:20]1[cH:21][cH:22][c:23]([CH2:24][Cl:25])[cH:26][cH:27]1>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14]2)[n:15][c:16... | CNC(=O)c1cc(Oc2ccc(NC)c(N)c2)ccn1.O=C(Cl)c1ccc(CCl)cc1 | CNC(=O)c1cc(Oc2ccc3c(c2)nc(NC(=O)c2ccc(CCl)cc2)n3C)ccn1 | null | null | CC(=O)C | Aromatic Heterocycle Formation | OtherReaction | 6007ce27c8fab5f5472c061eb36aa5e117a23e5c5c565f74ceb6415f1e4399f6 | f9acae1c78587942b501ef34ad83c994b8601ae314b6fafb351abe1b05ec8565 | O=C(Nc1nc2cc(Oc3ccncc3)ccc2[nH]1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10](-[NH2;D1;+0:11]):[c:12]>>[C;D1;H3:6]-[n;H0;D3;+0:7]1:[c:8](:[c:9]):[c:10](:[c:12]):[n;H0;D2;+0:11]:[c:13]:1-[#7:14]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 16 | HOUR | A solution of sodium thiocyanate (1 eq) in acetone was added slowly in to a solution of 4-(chloromethyl)benzoylchloride (1 eq) in acetone at 0° C. The mixture was then filtered in to a solution of {4-[3-amino-4-(methylamino)phenoxy](2-pyridyl)}-N-methylcarboxamide (1 eq) in acetone. Formation of N-acylthiourea was foll... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine.Secondary amine | Secondary amide | c1ccccc1 | c1ccc2nc[nH]c2c1 | c1ccncc1.c1ccc2nc[nH]c2c1.c1ccccc1 | HCl | CC(=O)C | null | 16 | CNC(=O)c1cc(Oc2ccc(NC)c(N)c2)ccn1.O=C(Cl)c1ccc(CCl)cc1>CC(=O)C>CNC(=O)c1cc(Oc2ccc3c(c2)nc(NC(=O)c2ccc(CCl)cc2)n3C)ccn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-07dd05e6ebd64ac0b8c02b2d0f84ec50 | Clc1ccnc(Cl)n1.OB(O)c1cccnc1>>Clc1nccc(-c2cccnc2)n1 | ClC1=NC=CC(=N1)Cl.N1=CC(=CC=C1)B(O)O.C([O-])([O-])=O.[Na+].[Na+]>>ClC1=NC=CC(=N1)C=1C=NC=CC1 | Cl[c:6]1[cH:5][cH:4][n:3][c:2]([Cl:1])[n:13]1.OB(O)[c:7]1[cH:8][cH:9][cH:10][n:11][cH:12]1>>[Cl:1][c:2]1[n:3][cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][n:11][cH:12]2)[n:13]1 | Clc1ccnc(Cl)n1.OB(O)c1cccnc1 | Clc1nccc(-c2cccnc2)n1 | null | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)[C-]1C=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2] | O1CCCC1.O | C-C Coupling | Suzuki coupling with boronic acids | 51855f0568b0c9a2f03c51034f8881daa4aef477007bbafb8803ff38f26b4c50 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1cncc(-c2ccncn2)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1.O-B(-O)-[c;H0;D3;+0:8]1:[c:9]:[#7;a:10]:[c:11]:[c:12]:[c:13]:1>>[Cl;D1;H0:4]-[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8]2:[c:9]:[#7;a:10]:[c:11]:[c:12]:[c:13]:2):[c:7]:[c:6]:[#7;a:5]:1 | null | [] | 60 | CELSIUS | null | null | Nitrogen was bubbled through a solution of 2,4-dichloropyrimidine (1 eq) in tetrahydrofuran and water (3:1) for 0.5 h. Bis(diphenylphosphino)ferrocene Palladium(II)chloride (0.05 eq) followed by pyridine-3-boronic acid (1 eq) and sodium carbonate (3 eq) was added and the mixture was heated to 60° C. for 16 h under nitr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cncnc1.c1ccncc1 | c1cncnc1.c1ccncc1 | c1cncnc1.c1ccncc1 | HCl.B | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)[C-]1C=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2].O1CCCC1.O | 60 | null | Clc1ccnc(Cl)n1.OB(O)c1cccnc1>[Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)[C-]1C=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2].O1CCCC1.O>Clc1nccc(-c2cccnc2)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-489fdd3767e74cdab1836ba0effdcde5 | Clc1nccc(-c2cccnc2)n1.Nc1ccc(O)cc1[N+](=O)[O-]>>Nc1ccc(Oc2nccc(-c3cccnc3)n2)cc1[N+](=O)[O-] | NC1=C(C=C(C=C1)O)[N+](=O)[O-].ClC1=NC=CC(=N1)C=1C=NC=CC1>>[N+](=O)([O-])C1=C(C=CC(=C1)OC1=NC=CC(=N1)C=1C=NC=CC1)N | Cl[c:7]1[n:8][cH:9][cH:10][c:11](-[c:12]2[cH:13][cH:14][cH:15][n:16][cH:17]2)[n:18]1.[NH2:1][c:2]1[cH:3][cH:4][c:5]([OH:6])[cH:19][c:20]1[N+:21](=[O:22])[O-:23]>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[n:8][cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][n:16][cH:17]3)[n:18]2)[cH:19][c:20]1[N+:21](=[O:22])[O-:23] | Clc1nccc(-c2cccnc2)n1.Nc1ccc(O)cc1[N+](=O)[O-] | Nc1ccc(Oc2nccc(-c3cccnc3)n2)cc1[N+](=O)[O-] | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 38da1e480b17968341fc50d07104da93d31f20765e3b36e5a0790cb6b1d88a10 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2nccc(-c3cccnc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | A solution of 4-amino-3-nitro-phenol (1 eq) and 2-chloro-4-(3-pyridyl)pyrimidine (1 eq) in N,N-dimethylformamide was microwaved at 150° C. for 10 mins. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was concentrated and purified on silica gel to yield 2-nitro-4-(4-(3-pyridyl)pyr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccncc1 | HCl | CN(C=O)C | null | null | Clc1nccc(-c2cccnc2)n1.Nc1ccc(O)cc1[N+](=O)[O-]>CN(C=O)C>Nc1ccc(Oc2nccc(-c3cccnc3)n2)cc1[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a7fcc24149aa4eb08f3039f2959434d8 | Nc1ccc(Oc2nccc(-c3cccnc3)n2)cc1[N+](=O)[O-]>>Nc1ccc(Oc2nccc(-c3cccnc3)n2)cc1N | [N+](=O)([O-])C1=C(C=CC(=C1)OC1=NC=CC(=N1)C=1C=NC=CC1)N>>N1=CC(=CC=C1)C1=NC(=NC=C1)OC=1C=C(C(=CC1)N)N | O=[N+:21]([O-])[c:20]1[c:2]([NH2:1])[cH:3][cH:4][c:5]([O:6][c:7]2[n:8][cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][n:16][cH:17]3)[n:18]2)[cH:19]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([O:6][c:7]2[n:8][cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][n:16][cH:17]3)[n:18]2)[cH:19][c:20]1[NH2:21] | Nc1ccc(Oc2nccc(-c3cccnc3)n2)cc1[N+](=O)[O-] | Nc1ccc(Oc2nccc(-c3cccnc3)n2)cc1N | null | [Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(Oc2nccc(-c3cccnc3)n2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The mixture containing 2-nitro-4-(4-(3-pyridyl)pyrimidin-2-yloxy)phenylamine in methanol with catalytic amount of 10% Pd/C was hydrogenated until disappearance of yellow color to yield 4-(4-(3-pyridyl)pyrimidin-2-yloxy)benzene-1,2-diamine. MS: MH+=279.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1cncnc1.c1ccncc1 | Other | [Pd].CO | null | null | Nc1ccc(Oc2nccc(-c3cccnc3)n2)cc1[N+](=O)[O-]>[Pd].CO>Nc1ccc(Oc2nccc(-c3cccnc3)n2)cc1N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-084fb7b4da67426aa581b30a57eee387 | Nc1ccc(Oc2nccc(-c3cccnc3)n2)cc1N.O=C(Cl)c1ccc(CCl)cc1>>O=C(Nc1nc2ccc(Oc3nccc(-c4cccnc4)n3)cc2[nH]1)c1ccc(CCl)cc1 | [S-]C#N.[Na+].ClCC1=CC=C(C(=O)Cl)C=C1.N1=CC(=CC=C1)C1=NC(=NC=C1)OC=1C=C(C(=CC1)N)N.Cl.C(C)N=C=NCCCN(C)C>>ClCC1=CC=C(C=C1)C(=O)NC=1NC2=C(N1)C=CC(=C2)OC2=NC=CC(=N2)C=2C=NC=CC2 | [NH2:5][c:6]1[cH:7][cH:8][c:9]([O:10][c:11]2[n:12][cH:13][cH:14][c:15](-[c:16]3[cH:17][cH:18][cH:19][n:20][cH:21]3)[n:22]2)[cH:23][c:24]1[NH2:25].Cl[C:2](=[O:1])[c:26]1[cH:27][cH:28][c:29]([CH2:30][Cl:31])[cH:32][cH:33]1>>[O:1]=[C:2]([NH:3][c:4]1[n:5][c:6]2[cH:7][cH:8][c:9]([O:10][c:11]3[n:12][cH:13][cH:14][c:15](-[c:1... | Nc1ccc(Oc2nccc(-c3cccnc3)n2)cc1N.O=C(Cl)c1ccc(CCl)cc1 | O=C(Nc1nc2ccc(Oc3nccc(-c4cccnc4)n3)cc2[nH]1)c1ccc(CCl)cc1 | null | null | CC(=O)C | Aromatic Heterocycle Formation | OtherReaction | 84492309ebd88369b38543aed3a10403ecb24f9be5ac8e8d692194c41bfc42f5 | e3e959b05bda8dad38bcefce5939efac6b07ca7f2b99a15789ad53e999a19964 | O=C(Nc1nc2ccc(Oc3nccc(-c4cccnc4)n3)cc2[nH]1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9](-[NH2;D1;+0:10]):[c:11]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[#7:12]-[c:13]1:[n;H0;D2;+0:10]:[c:9](:[c:11]):[c:7](:[c:8]):[nH;D2;+0:6]:1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | 16 | HOUR | A solution of sodium thiocyanate (1 eq) in acetone was added slowly in to a solution of 4-(chloromethyl)benzoylchloride (1 eq) in acetone at 0° C. The mixture was then filtered in to a solution of 4-(4-(3-pyridyl)pyrimidin-2-yloxy)benzene-1,2-diamine (1 eq) in acetone. Formation of N-acylthiourea was followed by LC/MS.... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine.Primary amine | Secondary amide | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1.c1cncnc1.c1ccncc1.c1ccccc1 | HCl | CC(=O)C | null | 16 | Nc1ccc(Oc2nccc(-c3cccnc3)n2)cc1N.O=C(Cl)c1ccc(CCl)cc1>CC(=O)C>O=C(Nc1nc2ccc(Oc3nccc(-c4cccnc4)n3)cc2[nH]1)c1ccc(CCl)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b9a59be9cda948e58ac95e309bfa0a86 | CCN1CCNCC1.O=[N+]([O-])c1ccc(F)cc1>>CCN1CCN(c2ccc([N+](=O)[O-])cc2)CC1 | FC1=CC=C(C=C1)[N+](=O)[O-].C(C)N1CCNCC1.C(C)(C)N(C(C)C)CC>>C(C)N1CCN(CC1)C1=CC=C(C=C1)[N+](=O)[O-] | [CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][NH:6][CH2:16][CH2:17]1.F[c:7]1[cH:8][cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14][cH:15]1>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][N:6]([c:7]2[cH:8][cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14][cH:15]2)[CH2:16][CH2:17]1 | CCN1CCNCC1.O=[N+]([O-])c1ccc(F)cc1 | CCN1CCN(c2ccc([N+](=O)[O-])cc2)CC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | d687b31bdda9f407fdde6ca57e67eee0681e173646c617afef7770c56d05bab9 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | null | [] | 80 | CELSIUS | null | null | To 4-fluro-1-nitrobenzene(1 eq) in N,N-dimethylformamide was added Ethyl piperazine (2 eq) and N,N-diisopropylethyl amine (2 eq) and heated at 80° C. for 16 h. Concentrated the resultant mixture and partitioned between ethyl acetate and water. The organic layer was then washed with brine and dried with sodium sulfate a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | HF | CN(C=O)C | 80 | null | CCN1CCNCC1.O=[N+]([O-])c1ccc(F)cc1>CN(C=O)C>CCN1CCN(c2ccc([N+](=O)[O-])cc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-81e578f4f7604e9c85bdfe9dfa76cfd4 | CCN1CCN(c2ccc([N+](=O)[O-])cc2)CC1>>CCN1CCN(c2ccc(N)cc2)CC1 | C(C)N1CCN(CC1)C1=CC=C(C=C1)[N+](=O)[O-]>>C(C)N1CCN(CC1)C1=CC=C(C=C1)N | O=[N+:11]([O-])[c:10]1[cH:9][cH:8][c:7]([N:6]2[CH2:5][CH2:4][N:3]([CH2:2][CH3:1])[CH2:15][CH2:14]2)[cH:13][cH:12]1>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][N:6]([c:7]2[cH:8][cH:9][c:10]([NH2:11])[cH:12][cH:13]2)[CH2:14][CH2:15]1 | CCN1CCN(c2ccc([N+](=O)[O-])cc2)CC1 | CCN1CCN(c2ccc(N)cc2)CC1 | null | [Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(N2CCNCC2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The mixture containing 4-ethyl-1-(4-nitrophenyl)piperazine in methanol with catalytic amount of 10% Pd/C was hydrogenated to yield 4-(4-ethylpiperazinyl)phenylamine. MS: MH+=205.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | C1C[NH]CC[NH]1.c1ccccc1 | Other | [Pd].CO | null | null | CCN1CCN(c2ccc([N+](=O)[O-])cc2)CC1>[Pd].CO>CCN1CCN(c2ccc(N)cc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c9a54c6438a5492985c4aac36f9c2b88 | C1COCCN1.O=[N+]([O-])c1ccc(CCBr)cc1>>O=[N+]([O-])c1ccc(CCN2CCOCC2)cc1 | BrCCC1=CC=C(C=C1)[N+](=O)[O-].N1CCOCC1>>[N+](=O)([O-])C1=CC=C(C=C1)CCN1CCOCC1 | [NH:10]1[CH2:11][CH2:12][O:13][CH2:14][CH2:15]1.Br[CH2:9][CH2:8][c:7]1[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:17][cH:16]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)[cH:16][cH:17]1 | C1COCCN1.O=[N+]([O-])c1ccc(CCBr)cc1 | O=[N+]([O-])c1ccc(CCN2CCOCC2)cc1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 2bad30dcdb0a20edb8ce877f072b133eedfd870621da393ec393128bfee00977 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CCN2CCOCC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[c:3].[#8:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[c:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#8:4]-[C:9]-[C:8]-1 | null | [] | null | null | 16 | HOUR | To 4-(2-bromoethyl)-1-nitrobenzene(1 eq) in tetrahydrofuran was added morpholine (3 eq) and stir for 16 h at ambient temperature. Concentrating and passing through a plug of silica gave 4-[2-(4-nitrophenyl)ethylmorpholine. MS: MH+=236.
Conditions: See reaction.notes.procedure_details.
Workup: Concentrating | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1COCCN1 | C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1 | HBr | O1CCCC1 | null | 16 | C1COCCN1.O=[N+]([O-])c1ccc(CCBr)cc1>O1CCCC1>O=[N+]([O-])c1ccc(CCN2CCOCC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ff93e64ab2394f70bb775a9f0729521e | O=[N+]([O-])c1ccc(CCN2CCOCC2)cc1>>Nc1ccc(CCN2CCOCC2)cc1 | [N+](=O)([O-])C1=CC=C(C=C1)CCN1CCOCC1>>N1(CCOCC1)CCC1=CC=C(C=C1)N | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[cH:14][cH:15]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[cH:14][cH:15]1 | O=[N+]([O-])c1ccc(CCN2CCOCC2)cc1 | Nc1ccc(CCN2CCOCC2)cc1 | null | [Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(CCN2CCOCC2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The mixture containing 4-[2-(4-nitrophenyl)ethyl]morpholine in methanol with catalytic amount of 10% Pd/C was hydrogenated to yield 4-(2-morpholin-4-ylethyl)phenylamine. MS: MH+=206.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.C1COCC[NH]1 | Other | [Pd].CO | null | null | O=[N+]([O-])c1ccc(CCN2CCOCC2)cc1>[Pd].CO>Nc1ccc(CCN2CCOCC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2ddcd16f5d4e40acba51d53f18999402 | CC(=O)c1ccc([N+](=O)[O-])cc1.NCc1ccccc1>>O=[N+]([O-])c1ccc(CCNCc2ccccc2)cc1 | [N+](=O)([O-])C1=CC=C(C=C1)C(C)=O.C1(=CC=CC=C1)CN.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>[N+](=O)([O-])C1=CC=C(C=C1)CCNCC1=CC=CC=C1 | O=[C:8]([c:7]1[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:19][cH:18]1)[CH3:9].[NH2:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][CH2:9][NH:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18][cH:19]1 | CC(=O)c1ccc([N+](=O)[O-])cc1.NCc1ccccc1 | O=[N+]([O-])c1ccc(CCNCc2ccccc2)cc1 | null | null | CO | Functional Group Addition | OtherReaction | 19fd62cf2098e96a4130feef29e9bf81adb1ccfebe3387cc1f5e2935ebb7056f | b485541a30741fb92d734951552491c7748625ed3b5658b6b29d788a0e8f8e57 | c1ccc(CCNCc2ccccc2)cc1 | O=[C;H0;D3;+0:1](-[CH3;D1;+0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[c:8]-[C:7]-[NH;D2;+0:6]-[CH2;D2;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | null | [] | null | null | 16 | HOUR | To a solution of 1-(4-nitrophenyl)ethan-1-one (1 eq) and phenylmethylamine (1 eq) in methanol was added sodiumtriacetoxyborohydride (1.2 eq). The resulting mixture was stirred at ambient temperature for 16 h. The mixture was concentrated and partitioned between ethyl acetate and water. The organic layer was concentrate... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | Other | CO | null | 16 | CC(=O)c1ccc([N+](=O)[O-])cc1.NCc1ccccc1>CO>O=[N+]([O-])c1ccc(CCNCc2ccccc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-72aac1ae9609429b8f12400afb045713 | O=[N+]([O-])c1ccc(CCNCc2ccccc2)cc1>>Nc1ccc(CCNCc2ccccc2)cc1 | [N+](=O)([O-])C1=CC=C(C=C1)CCNCC1=CC=CC=C1>>NC1=CC=C(C=C1)CCNCC1=CC=CC=C1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][NH:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][cH:17]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][NH:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][cH:17]1 | O=[N+]([O-])c1ccc(CCNCc2ccccc2)cc1 | Nc1ccc(CCNCc2ccccc2)cc1 | null | [Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(CCNCc2ccccc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The mixture containing [(4-nitrophenyl)ethyl]benzylamine in methanol with catalytic amount of 10% Pd/C was hydrogenated until disappearance of yellow color to yield [(4-aminophenyl)ethyl]benzylamine. MS: MH+=226.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | [Pd].CO | null | null | O=[N+]([O-])c1ccc(CCNCc2ccccc2)cc1>[Pd].CO>Nc1ccc(CCNCc2ccccc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2d2c569091a24068afd16715b91f3390 | NC(=O)C(F)(F)F.Nc1cc(F)ccc1[N+](=O)[O-]>>NCc1cc(F)ccc1[N+](=O)[O-] | S(=O)(=O)(OC)OC.FC=1C=CC(=C(C1)N)[N+](=O)[O-].FC(C(=O)OC(C(F)(F)F)=O)(F)F.FC(C(=O)N)(F)F.[OH-].[Na+]>>FC=1C=CC(=C(C1)CN)[N+](=O)[O-] | O=[C:2](C(F)(F)F)[NH2:1].N[c:3]1[cH:4][c:5]([F:6])[cH:7][cH:8][c:9]1[N+:10](=[O:11])[O-:12]>>[NH2:1][CH2:2][c:3]1[cH:4][c:5]([F:6])[cH:7][cH:8][c:9]1[N+:10](=[O:11])[O-:12] | NC(=O)C(F)(F)F.Nc1cc(F)ccc1[N+](=O)[O-] | NCc1cc(F)ccc1[N+](=O)[O-] | null | [Cl-].C(C1=CC=CC=C1)[N+](C)(C)C | C(C)#N.C1(=CC=CC=C1)C.C(Cl)Cl | C-C Coupling | OtherReaction | 57eeb6cb444d729ea25c9af40d90b2b85339cfcfa01a82f89f645f8d3327247a | c6562711aeb2bb6c0ed826650c3482d37ecfc2f4b0030c6f964c1758331569dd | c1ccccc1 | F-C(-F)(-F)-[C;H0;D3;+0:1](=O)-[N;D1;H2:2].N-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6](-[#7;+:7]):[c:8]>>[#7;+:7]-[c:6](:[c:8]):[c;H0;D3;+0:3](-[CH2;D2;+0:1]-[N;D1;H2:2]):[c:4]:[c:5] | null | [] | 0 | CELSIUS | 10 | MINUTE | A solution of 5-fluro-2-nitrophenylamine (1 eq) in methylenechloride was treated with trifluoroacetic anhydride (1 eq) and stirred for 10 minutes at 0° C. The mixture was quenched with saturated sodium bicarbonate solution. The organic layer was separated and washed with water, brine, dried and evaporated. To the solut... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Primary amide.Primary amine | null | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | [Cl-].C(C1=CC=CC=C1)[N+](C)(C)C.C(C)#N.C1(=CC=CC=C1)C.C(Cl)Cl | 0 | 0.166667 | NC(=O)C(F)(F)F.Nc1cc(F)ccc1[N+](=O)[O-]>[Cl-].C(C1=CC=CC=C1)[N+](C)(C)C.C(C)#N.C1(=CC=CC=C1)C.C(Cl)Cl>NCc1cc(F)ccc1[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-40acfaf085a14c889f79846a72fdd46b | CN(C)C=O.CNC(=O)c1cccc(O)c1.C[Si](C)(C)[N-][Si](C)(C)C.Nc1cc(F)ccc1[N+](=O)[O-]>>CNC(=O)c1cc(Oc2ccc([N+](=O)[O-])c(NC)c2)ccn1 | CN(C=O)C.FC=1C=CC(=C(C1)N)[N+](=O)[O-].C[Si](C)(C)[N-][Si](C)(C)C.[K+].OC=1C=C(C=CC1)C(=O)NC.C([O-])([O-])=O.[K+].[K+]>>CNC(=O)C1=NC=CC(=C1)OC1=CC(=C(C=C1)[N+](=O)[O-])NC | CN(C=O)[CH3:18].c1[c:5]([C:3]([NH:2][CH3:1])=[O:4])[cH:6][c:7]([OH:8])[cH:20][cH:21]1.C[Si](C)(C)[N-:22][Si](C)(C)C.F[c:9]1[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[c:16]([NH2:17])[cH:19]1>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[c:16]([NH:17][CH3:18])[cH... | CN(C)C=O.CNC(=O)c1cccc(O)c1.C[Si](C)(C)[N-][Si](C)(C)C.Nc1cc(F)ccc1[N+](=O)[O-] | CNC(=O)c1cc(Oc2ccc([N+](=O)[O-])c(NC)c2)ccn1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | c634879a8d4528500fc2be3de37e4a0ee8d423d97c1d4f23bc31c4f4d8266e30 | 54c57484907ba531ad2d669934ec72f5a32e91a9ba1ac88e7bbfd9456582c8a2 | c1ccc(Oc2ccncc2)cc1 | C-N(-[CH3;D1;+0:1])-C=O.C-[Si](-C)(-C)-[N-;H0;D2:2]-[Si](-C)(-C)-C.F-[c;H0;D3;+0:3]1:[c:4]:[c:5]:[c:6]:[c:7](-[NH2;D1;+0:8]):[c:9]:1.[C;D1;H3:10]-[#7:11]-[C:12](=[O;D1;H0:13])-[c;H0;D3;+0:14]1:[c:15]:[c:16](-[OH;D1;+0:17]):[c:18]:[cH;D2;+0:19]:c:1>>[C;D1;H3:10]-[#7:11]-[C:12](=[O;D1;H0:13])-[c;H0;D3;+0:14]1:[c:15]:[c:1... | null | [] | 90 | CELSIUS | 16 | HOUR | The mixture containing 5-fluro-2-nitrophenylamine (1 eq), Potassium bis(trimethylsilyl)amide (2 eq) was stirred in dimethylformamide for 2 hours at room temperature. To this mixture was added (3-hydroxyphenyl)-N-methylcarboxamide (1 eq) and Potassium carbonate (1.2 eq) and stirred at 90° C. for 16 h. The reaction mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amide.Aromatic alcohol.Primary amine.Silyl protective group.Silyl protective group | Ether.Secondary amine | c1ccccc1.c1ccccc1 | c1ccncc1.c1ccccc1 | c1ccncc1.c1ccccc1 | HF | null | 90 | 16 | CN(C)C=O.CNC(=O)c1cccc(O)c1.C[Si](C)(C)[N-][Si](C)(C)C.Nc1cc(F)ccc1[N+](=O)[O-]>>CNC(=O)c1cc(Oc2ccc([N+](=O)[O-])c(NC)c2)ccn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-204e0e7bf12a4fd99666168d14b4e1c1 | CNC(=O)c1cc(Oc2ccc(N)c(NC)c2)ccn1.S=C=Nc1ccc(Br)cc1>>CNC(=O)c1cc(Oc2ccc3nc(Nc4ccc(Br)cc4)n(C)c3c2)ccn1 | IC.NC1=C(C=C(OC2=CC(=NC=C2)C(=O)NC)C=C1)NC.BrC1=CC=C(C=C1)N=C=S>>BrC1=CC=C(C=C1)NC1=NC2=C(N1C)C=C(C=C2)OC2=CC(=NC=C2)C(=O)NC | [CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][c:12]([NH2:13])[c:25]([NH:23][CH3:24])[cH:26]2)[cH:27][cH:28][n:29]1.S=[C:14]=[N:15][c:16]1[cH:17][cH:18][c:19]([Br:20])[cH:21][cH:22]1>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][c:12]3[n:13][c:14]([NH:15][c:16]4[cH:17][cH... | CNC(=O)c1cc(Oc2ccc(N)c(NC)c2)ccn1.S=C=Nc1ccc(Br)cc1 | CNC(=O)c1cc(Oc2ccc3nc(Nc4ccc(Br)cc4)n(C)c3c2)ccn1 | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | 4b3e260fa6094641dfa114b35f3471079a338332f41031b31ba4b7bb465b4139 | c2745d0d96944794048cb0a435469fb3c0efa689f6d5e8d4fd6447372cabc5f8 | c1ccc(Nc2nc3ccc(Oc4ccncc4)cc3[nH]2)cc1 | S=[C;H0;D2;+0:1]=[N;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10](-[NH2;D1;+0:11]):[c:12]>>[C;D1;H3:6]-[n;H0;D3;+0:7]1:[c:8](:[c:9]):[c:10](:[c:12]):[n;H0;D2;+0:11]:[c;H0;D3;+0:1]:1-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | 60 | CELSIUS | 2 | HOUR | A solution of the {4-[4-amino-3-(methylamino)phenoxy](2-pyridyl)}-N-methyl-carboxamide(1 eq) in methanol was treated with 4-bromophenylisothiocyanate (1 eq) and stirred at 60° C. for 2 hours. The reaction mixture was cooled down to room temperature and iodomethane (1 eq) was added and stirred overnight at 60° C. The re... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine.Isothiocyanate | Secondary amine | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccncc1.c1ccc2[nH]cnc2c1.c1ccccc1 | Other | CO | 60 | 2 | CNC(=O)c1cc(Oc2ccc(N)c(NC)c2)ccn1.S=C=Nc1ccc(Br)cc1>CO>CNC(=O)c1cc(Oc2ccc3nc(Nc4ccc(Br)cc4)n(C)c3c2)ccn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b2672337f49f4fea831bf1a6c0ab6f63 | Nc1ccc([N+](=O)[O-])cc1N.S=C=Nc1ccc(Br)cc1>>O=[N+]([O-])c1ccc2nc(Nc3ccc(Br)cc3)[nH]c2c1 | IC.[N+](=O)([O-])C=1C=C(C(=CC1)N)N.BrC1=CC=C(C=C1)N=C=S>>BrC1=CC=C(C=C1)NC=1NC2=C(N1)C=CC(=C2)[N+](=O)[O-] | [O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([NH2:8])[c:19]([NH2:18])[cH:20]1.S=[C:9]=[N:10][c:11]1[cH:12][cH:13][c:14]([Br:15])[cH:16][cH:17]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[n:8][c:9]([NH:10][c:11]3[cH:12][cH:13][c:14]([Br:15])[cH:16][cH:17]3)[nH:18][c:19]2[cH:20]1 | Nc1ccc([N+](=O)[O-])cc1N.S=C=Nc1ccc(Br)cc1 | O=[N+]([O-])c1ccc2nc(Nc3ccc(Br)cc3)[nH]c2c1 | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | b379a633a6d6a7ef71a4ec729ac27ffb0470b0a7feb5a79c5b4b49860868cf5b | 85c21648c239f13e3de224b3880be5fbcc059dde8446f4822bf814f376b11c25 | c1ccc(Nc2nc3ccccc3[nH]2)cc1 | S=[C;H0;D2;+0:1]=[N;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9](-[NH2;D1;+0:10]):[c:11]>>[c:4]:[c:3](-[NH;D2;+0:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:10]:[c:9](:[c:11]):[c:7](:[c:8]):[nH;D2;+0:6]:1):[c:5] | null | [] | 60 | CELSIUS | 2 | HOUR | A solution of the 4-nitrobenzene-1,2-diamine in methanol was treated with 4-bromo phenyl isothiocyanate (1 eq) and stirred at 60° C. for 2 hours. The reaction mixture was cooled down to room temperature and iodomethane (1 eq) was added and stirred overnight at 60° C. The reaction was concentrated and purified on silica... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine.Isothiocyanate | Secondary amine | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccc2[nH]cnc2c1.c1ccccc1 | Other | CO | 60 | 2 | Nc1ccc([N+](=O)[O-])cc1N.S=C=Nc1ccc(Br)cc1>CO>O=[N+]([O-])c1ccc2nc(Nc3ccc(Br)cc3)[nH]c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f7c4bbc0a17847169a23efc66b8dd681 | CCN(CC)CC.CNC(=O)c1cc(Oc2ccc(N)c(N)c2)ccn1.O=C(O)Cc1ccc(Br)cc1>>CNC(=O)c1cc(Oc2ccc3c(c2)nc(Cc2ccc(Br)cc2)n3C)ccn1 | BrC1=CC=C(C=C1)CC(=O)O.C(C(=O)Cl)(=O)Cl.NC=1C=C(OC2=CC(=NC=C2)C(=O)NC)C=CC1N.C(C)N(CC)CC>>BrC1=CC=C(C=C1)CC1=NC2=C(N1C)C=CC(=C2)OC2=CC(=NC=C2)C(=O)NC | CCN(CC)C[CH3:26].[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][c:12]([NH2:25])[c:13]([NH2:15])[cH:14]2)[cH:27][cH:28][n:29]1.O=[C:16](O)[CH2:17][c:18]1[cH:19][cH:20][c:21]([Br:22])[cH:23][cH:24]1>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14]2)[n:15][... | CCN(CC)CC.CNC(=O)c1cc(Oc2ccc(N)c(N)c2)ccn1.O=C(O)Cc1ccc(Br)cc1 | CNC(=O)c1cc(Oc2ccc3c(c2)nc(Cc2ccc(Br)cc2)n3C)ccn1 | null | null | ClCCl.O1CCCC1.CN(C=O)C | Aromatic Heterocycle Formation | OtherReaction | 7bb2feb927f3b80cd9b65f74956a8f03463f56769daffd1fb82b38e5a408a8b2 | eb25e1adb2dda9b12f5be7597398e322af6c055fe8481cf7bc7c0f04aa065c68 | c1ccc(Cc2nc3cc(Oc4ccncc4)ccc3[nH]2)cc1 | C-C-N(-C-C)-C-[CH3;D1;+0:1].O-[C;H0;D3;+0:2](=O)-[C:3]-[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8](-[NH2;D1;+0:9]):[c:10]>>[CH3;D1;+0:1]-[n;H0;D3;+0:9]1:[c:8](:[c:10]):[c:6](:[c:7]):[n;H0;D2;+0:5]:[c;H0;D3;+0:2]:1-[C:3]-[c:4] | null | [] | 60 | CELSIUS | 2 | HOUR | To 4-bromophenyl acetic acid (1 eq) in dichoromethane containing a drop of N,N-dimethyl formamide at 0° C. was added oxalyl chloride (1.2 eq). The resulting mixture was then brought to ambient temperature and stirred for 2 h. The mixture was concentrated and to it was added tetrahydrofuran and [4-(3,4-diaminophenoxy)(2... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine.Primary amine.Tertiary amine | null | c1ccccc1 | c1ccc2nc[nH]c2c1 | c1ccncc1.c1ccc2nc[nH]c2c1.c1ccccc1 | HO- | ClCCl.O1CCCC1.CN(C=O)C | 60 | 2 | CCN(CC)CC.CNC(=O)c1cc(Oc2ccc(N)c(N)c2)ccn1.O=C(O)Cc1ccc(Br)cc1>ClCCl.O1CCCC1.CN(C=O)C>CNC(=O)c1cc(Oc2ccc3c(c2)nc(Cc2ccc(Br)cc2)n3C)ccn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4993b6bd45dd4b758422db41b7abca7f | O=C(O)c1ccc(N=C=S)cc1>>O=C(O)c1ccccc1 | IC.NC=1C=C(OC2=CC(=NC=C2)C(=O)NC)C=CC1NC.N(=C=S)C1=CC=C(C(=O)O)C=C1>>C(C1=CC=CC=C1)(=O)O | S=C=N[c:7]1[cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:9][cH:8]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1 | O=C(O)c1ccc(N=C=S)cc1 | O=C(O)c1ccccc1 | null | null | CO | Functional Group Interconversion | OtherReaction | 9f8c98612863acf953fea7ac735cf5ef5c9344111235f882da4aeae8bee29c12 | 4e930e84ca7a4b5a1b2ffdfd0ad5173746b70455a6634f66996611a6644c2fb6 | c1ccccc1 | S=C=N-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]>>[c:3]:[c:2]:[cH;D2;+0:1]:[c:4]:[c:5] | null | [] | 60 | CELSIUS | 3 | HOUR | To {4-[3-amino-4-(methylamino)phenoxy](2-pyridyl)}-N-methylcarboxamide (1 eq) in methanol was added 4-isothiocyanatobenzoic acid (1 eq) and stirred at 60° C. for 3 h. To it was then added iodomethane (1 eq) and heated to 60° C. for 3 h. and concentrated the solvent and purified on silica gel to yield 4-({1-methyl-5-[2-... | 10.6084/m9.figshare.5104873.v1 | null | Isothiocyanate | null | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | CO | 60 | 3 | O=C(O)c1ccc(N=C=S)cc1>CO>O=C(O)c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-29296f4d1995470382504a5d3d73f23e | O=C(O)c1cccc(N=C=S)c1>>O=C(O)c1ccccc1 | IC.CNC=O.N(=C=S)C=1C=C(C(=O)O)C=CC1>>C(C1=CC=CC=C1)(=O)O | S=C=N[c:6]1[cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:9][cH:8][cH:7]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1 | O=C(O)c1cccc(N=C=S)c1 | O=C(O)c1ccccc1 | null | null | CO | Functional Group Interconversion | OtherReaction | 9f8c98612863acf953fea7ac735cf5ef5c9344111235f882da4aeae8bee29c12 | 4e930e84ca7a4b5a1b2ffdfd0ad5173746b70455a6634f66996611a6644c2fb6 | c1ccccc1 | S=C=N-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](=[O;D1;H0:5])-[O;D1;H1:6]):[c:7]:[c:8]>>[O;D1;H0:5]=[C:4](-[O;D1;H1:6])-[c:3]:[c:2]:[cH;D2;+0:1]:[c:7]:[c:8] | null | [] | 60 | CELSIUS | 3 | HOUR | To 4-[3-amino-4-(methylamino)phenoxy](2-pyridyl)}-N-methylcarboxamide (1 eq) in methanol was added 3-isothiocyanatobenzoic acid (1 eq) and stirred at 60° C. for 3 h. To it was then added iodomethane (1 eq) and heated to 60° C. for 3 h and concentrated the solvent and purified on silica gel to yield 3-({1-methyl-5-[2-(N... | 10.6084/m9.figshare.5104873.v1 | null | Isothiocyanate | null | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | CO | 60 | 3 | O=C(O)c1cccc(N=C=S)c1>CO>O=C(O)c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7dedb8c1722640c2ab736f437c5820fd | CNC(=O)c1cccc(Cl)c1.CNc1cc(OC)c(O)cc1[N+](=O)[O-]>>CNC(=O)c1cc(Oc2cc([N+](=O)[O-])c(NC)cc2OC)ccn1 | ClC=1C=C(C=CC1)C(=O)NC.C([O-])([O-])=O.[K+].[K+].COC1=C(C=C(C(=C1)NC)[N+](=O)[O-])O.CC(C)([O-])C.[K+].CN(C(C)=O)C>>COC1=C(OC2=CC(=NC=C2)C(=O)NC)C=C(C(=C1)NC)[N+](=O)[O-] | Cl[c:7]1[cH:6][c:5]([C:3]([NH:2][CH3:1])=[O:4])c[cH:23][cH:22]1.[OH:8][c:9]1[cH:10][c:11]([N+:12](=[O:13])[O-:14])[c:15]([NH:16][CH3:17])[cH:18][c:19]1[O:20][CH3:21]>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([O:8][c:9]2[cH:10][c:11]([N+:12](=[O:13])[O-:14])[c:15]([NH:16][CH3:17])[cH:18][c:19]2[O:20][CH3:21])[cH:22][... | CNC(=O)c1cccc(Cl)c1.CNc1cc(OC)c(O)cc1[N+](=O)[O-] | CNC(=O)c1cc(Oc2cc([N+](=O)[O-])c(NC)cc2OC)ccn1 | null | null | null | Protection | OtherReaction | f0023f5cb78e4f43639596fb9d7e792c21b5d63a2c4e24a596c544a93eb8f3cf | cf1075be1c1ecf3bb8058899ddc12870a38487ecc9322d6e66205e53a46d9b16 | c1ccc(Oc2ccncc2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:c:[c;H0;D3;+0:4](-[C:5](=[O;D1;H0:6])-[#7:7]-[C;D1;H3:8]):[c:9]:1.[OH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C;D1;H3:8]-[#7:7]-[C:5](=[O;D1;H0:6])-[c;H0;D3;+0:4]1:[#7;a:14]:[cH;D2;+0:3]:[c:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:10]-[c:11](:[c:12]):[c:13]):[c:9]:1 | null | [] | null | null | null | null | To a stirred solution of 2-methoxy-4-(methylamino)-5-nitrophenol(1 eq) in N,N-dimethylacetamide was added potassium-t-butoxide (1.2 eq) and continued stirring at ambient temperature until it solidified. To it was then added (3-chlorophenyl)-N-methylcarboxamide (1 eq) and anhydrous potassium carbonate (1 eq) and the res... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccccc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | HCl | null | null | null | CNC(=O)c1cccc(Cl)c1.CNc1cc(OC)c(O)cc1[N+](=O)[O-]>>CNC(=O)c1cc(Oc2cc([N+](=O)[O-])c(NC)cc2OC)ccn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4060eb24e13c46d8965a91c2c6d0bd1f | CNc1cc(OC)c(Oc2ccnc(C(=O)OC(C)(C)C)c2)cc1N.Cn1c(Nc2ccc(Cl)cc2)nc2cc(Oc3ccnc(C(=O)OC(C)(C)C)c3)ccc21>>COc1cc2c(cc1OC1(C(=O)O)C=CC=CN1)nc(Nc1ccc(Cl)cc1)n2C | C(C)(C)(C)OC(=O)C1=NC=CC(=C1)OC1=CC2=C(N(C(=N2)NC2=CC=C(C=C2)Cl)C)C=C1.C(C)(C)(C)OC(=O)C1=NC=CC(=C1)OC1=CC(=C(C=C1OC)NC)N.NC(=S)N.FC(C(=O)O)(F)F.IC>>ClC1=CC=C(C=C1)NC1=NC2=C(N1C)C=C(C(=C2)OC2(NC=CC=C2)C(=O)O)OC | CNc1c(N)[cH:7][c:8]([O:9][c:10]2[cH:14][c:15]([C:11](=[O:12])[O:13]C(C)(C)C)[n:18][cH:17][cH:16]2)[c:3]([O:2][CH3:1])[cH:4]1.CC(C)(C)OC(=O)c1cc(Oc2cc[c:5]3[c:6](c2)[n:19][c:20]([NH:21][c:22]2[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]2)[n:29]3[CH3:30])ccn1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[O:9][C:10]1([... | CNc1cc(OC)c(Oc2ccnc(C(=O)OC(C)(C)C)c2)cc1N.Cn1c(Nc2ccc(Cl)cc2)nc2cc(Oc3ccnc(C(=O)OC(C)(C)C)c3)ccc21 | COc1cc2c(cc1OC1(C(=O)O)C=CC=CN1)nc(Nc1ccc(Cl)cc1)n2C | null | null | C(Cl)Cl.CO | C-C Coupling | OtherReaction | 29efb81d47594bacad1863038bfbc6613a20e196cacf2349980ec228b88f5977 | 4edbc5aa10c177b20f61383c702da22155b87866fa39db7fef23ed8b6baa10fc | C1=CNC(Oc2ccc3[nH]c(Nc4ccccc4)nc3c2)C=C1 | C-C(-C)(-C)-O-C(=O)-c1:c:c(-O-c2:c:c:[c;H0;D3;+0:1]3:[#7;a:2](-[C;D1;H3:3]):[c:4](-[#7:5]):[#7;a:6]:[c;H0;D3;+0:7]:3:c:2):c:c:n:1.C-N-c1:[cH;D2;+0:8]:[c:9](-[#8:10]):[c:11](-[#8:12]-[c;H0;D3;+0:13]2:[cH;D2;+0:14]:[c;H0;D3;+0:15](-[C;H0;D3;+0:16](=[O;D1;H0:17])-[O;H0;D2;+0:18]-C(-C)(-C)-C):[n;H0;D2;+0:19]:[cH;D2;+0:20]:... | null | [] | null | null | 16 | HOUR | To tert-butyl4-[3-amino-6-methoxy-4-(methylamino)phenoxy]pyridine-2-carboxylate(1 eq) in methanol was added 4-chlorobenzeneisothiocyanate (1 eq) and stir at ambient temperature for 16 h. Formation of the corresponding thiourea was followed by LC/MS. To it was then added iodomethane (1 eq) and heated to 60° C. for 2 h. ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ether.Ether.Primary amine.Secondary amine.Boc.Boc | Enamine.Carboxylic acid.Ether.Conjugated diene | c1ccccc1.c1ccncc1.c1ccncc1.c1nc2ccccc2[nH]1 | C1=CCNC=C1.c1ccc2[nH]cnc2c1 | C1=CCNC=C1.c1ccc2[nH]cnc2c1.c1ccccc1 | HO- | C(Cl)Cl.CO | null | 16 | CNc1cc(OC)c(Oc2ccnc(C(=O)OC(C)(C)C)c2)cc1N.Cn1c(Nc2ccc(Cl)cc2)nc2cc(Oc3ccnc(C(=O)OC(C)(C)C)c3)ccc21>C(Cl)Cl.CO>COc1cc2c(cc1OC1(C(=O)O)C=CC=CN1)nc(Nc1ccc(Cl)cc1)n2C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-25969f1c4fc64f5496562ec0d510d29a | COc1cc2c(cc1OC1(C(=O)O)C=CC=CN1)nc(Nc1ccc(Cl)cc1)n2C.NCCN1CCCC1>>COc1cc2c(cc1Oc1ccnc(C(=O)NCCN3CCCC3)c1)nc(Nc1ccc(Cl)cc1)n2C | ClC1=CC=C(C=C1)NC1=NC2=C(N1C)C=C(C(=C2)OC2(NC=CC=C2)C(=O)O)OC.N1(CCCC1)CCN.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=C2)N=N1.F[P-](F)(F)(F)(F)F.C(C)(C)N(C(C)C)CC>>ClC1=CC=C(C=C1)NC1=NC2=C(N1C)C=C(C(=C2)OC2=CC(=NC=C2)C(=O)NCCN2CCCC2)OC | O[C:15]([C:10]1([O:9][c:8]2[c:3]([O:2][CH3:1])[cH:4][c:5]3[c:6]([cH:7]2)[n:26][c:27]([NH:28][c:29]2[cH:30][cH:31][c:32]([Cl:33])[cH:34][cH:35]2)[n:36]3[CH3:37])[NH:13][CH:12]=[CH:11][CH:14]=[CH:25]1)=[O:16].[NH2:17][CH2:18][CH2:19][N:20]1[CH2:21][CH2:22][CH2:23][CH2:24]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]... | COc1cc2c(cc1OC1(C(=O)O)C=CC=CN1)nc(Nc1ccc(Cl)cc1)n2C.NCCN1CCCC1 | COc1cc2c(cc1Oc1ccnc(C(=O)NCCN3CCCC3)c1)nc(Nc1ccc(Cl)cc1)n2C | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | 94a4caa66bccd8e91e7b580a9f4a3c5157ecfe3b07bd32b3f62ac4bbe934c768 | 41c50182f03618bf5d6f37d7b2d64e215c63c1f5eafd63156eb9376a8393c769 | O=C(NCCN1CCCC1)c1cc(Oc2ccc3[nH]c(Nc4ccccc4)nc3c2)ccn1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D4;+0:3]1(-[#8:4]-[c:5])-[CH;D2;+0:6]=[CH;D2;+0:7]-[CH;D2;+0:8]=[CH;D2;+0:9]-[NH;D2;+0:10]-1.[C:11]-[C:12]-[NH2;D1;+0:13]>>[C:11]-[C:12]-[NH;D2;+0:13]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:7]1:[cH;D2;+0:6]:[c;H0;D3;+0:3](-[#8:4]-[c:5]):[cH;D2;+0:8]:[cH;D2;+0:9]:[n;H0;D2;+0:10]:1 | null | [] | null | null | 16 | HOUR | To 4-(2-{[4-chloropheylamino)-6-methoxy-1-methylbenzimidazol-5-yloxy)-pyridine-2-carboxylic acid(1 eq) in tetrahydrofuran was added 2-pyrrolidinylethylamine (2 eq), HBTU (2 eq) and N,N-diisopropylethylamine (4 eq) and stir at ambient temperature for 16 h. The mixture was then concentrated and partitioned between ethyl ... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Carboxylic acid.Ether.Primary amine.Conjugated diene | Ether.Secondary amide | C1=CCNC=C1 | c1ccncc1 | c1ccncc1.C1CC[NH]C1.c1ccc2[nH]cnc2c1.c1ccccc1 | HO- | O1CCCC1 | null | 16 | COc1cc2c(cc1OC1(C(=O)O)C=CC=CN1)nc(Nc1ccc(Cl)cc1)n2C.NCCN1CCCC1>O1CCCC1>COc1cc2c(cc1Oc1ccnc(C(=O)NCCN3CCCC3)c1)nc(Nc1ccc(Cl)cc1)n2C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fafcfcb36bd240f0b0d7485f30e31c96 | CNc1cc(OC)c(Oc2ccnc(C(=O)OC(C)(C)C)c2)cc1N.Cc1cc(Nc2nc3cc(Oc4ccnc(C(=O)OC(C)(C)C)c4)ccc3n2C)ccc1Br>>COc1cc2c(cc1OC1(C(=O)O)C=CC=CN1)nc(Nc1ccc(Br)c(C)c1)n2C | C(C)(C)(C)OC(=O)C1=NC=CC(=C1)OC1=CC2=C(N(C(=N2)NC2=CC(=C(C=C2)Br)C)C)C=C1.C(C)(C)(C)OC(=O)C1=NC=CC(=C1)OC1=CC(=C(C=C1OC)NC)N.NC(=S)N.FC(C(=O)O)(F)F.IC>>BrC1=C(C=C(C=C1)NC1=NC2=C(N1C)C=C(C(=C2)OC2(NC=CC=C2)C(=O)O)OC)C | CNc1c(N)[cH:7][c:8]([O:9][c:10]2[cH:14][c:15]([C:11](=[O:12])[O:13]C(C)(C)C)[n:18][cH:17][cH:16]2)[c:3]([O:2][CH3:1])[cH:4]1.CC(C)(C)OC(=O)c1cc(Oc2cc[c:5]3[c:6](c2)[n:19][c:20]([NH:21][c:22]2[cH:23][cH:24][c:25]([Br:26])[c:27]([CH3:28])[cH:29]2)[n:30]3[CH3:31])ccn1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[O:9]... | CNc1cc(OC)c(Oc2ccnc(C(=O)OC(C)(C)C)c2)cc1N.Cc1cc(Nc2nc3cc(Oc4ccnc(C(=O)OC(C)(C)C)c4)ccc3n2C)ccc1Br | COc1cc2c(cc1OC1(C(=O)O)C=CC=CN1)nc(Nc1ccc(Br)c(C)c1)n2C | null | null | C(Cl)Cl.CO | C-C Coupling | OtherReaction | 29efb81d47594bacad1863038bfbc6613a20e196cacf2349980ec228b88f5977 | 4edbc5aa10c177b20f61383c702da22155b87866fa39db7fef23ed8b6baa10fc | C1=CNC(Oc2ccc3[nH]c(Nc4ccccc4)nc3c2)C=C1 | C-C(-C)(-C)-O-C(=O)-c1:c:c(-O-c2:c:c:[c;H0;D3;+0:1]3:[#7;a:2](-[C;D1;H3:3]):[c:4](-[#7:5]):[#7;a:6]:[c;H0;D3;+0:7]:3:c:2):c:c:n:1.C-N-c1:[cH;D2;+0:8]:[c:9](-[#8:10]):[c:11](-[#8:12]-[c;H0;D3;+0:13]2:[cH;D2;+0:14]:[c;H0;D3;+0:15](-[C;H0;D3;+0:16](=[O;D1;H0:17])-[O;H0;D2;+0:18]-C(-C)(-C)-C):[n;H0;D2;+0:19]:[cH;D2;+0:20]:... | null | [] | null | null | 16 | HOUR | To tert-butyl4-[3-amino-6-methoxy-4-(methylamino)phenoxy]pyridine-2-carboxylate(1 eq) in methanol was added 4-bromo-3-methylbenzeneisothiocyanate (1 eq) and stir at ambient temperature for 16 h. Formation of the corresponding thiourea was followed by LC/MS. To it was then added iodomethane (1 eq) and heated to 60° C. f... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ether.Ether.Primary amine.Secondary amine.Boc.Boc | Enamine.Carboxylic acid.Ether.Conjugated diene | c1ccccc1.c1ccncc1.c1ccncc1.c1nc2ccccc2[nH]1 | C1=CCNC=C1.c1ccc2[nH]cnc2c1 | C1=CCNC=C1.c1ccc2[nH]cnc2c1.c1ccccc1 | HO- | C(Cl)Cl.CO | null | 16 | CNc1cc(OC)c(Oc2ccnc(C(=O)OC(C)(C)C)c2)cc1N.Cc1cc(Nc2nc3cc(Oc4ccnc(C(=O)OC(C)(C)C)c4)ccc3n2C)ccc1Br>C(Cl)Cl.CO>COc1cc2c(cc1OC1(C(=O)O)C=CC=CN1)nc(Nc1ccc(Br)c(C)c1)n2C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6577e9885f96489091e1c86056a89b32 | COc1cc2c(cc1OC1(C(=O)O)C=CC=CN1)nc(Nc1ccc(Br)c(C)c1)n2C.NCCN1CCCC1>>COc1cc2c(cc1Oc1ccnc(C(=O)NCCN3CCCC3)c1)nc(Nc1ccc(Br)c(C)c1)n2C | BrC1=C(C=C(C=C1)NC1=NC2=C(N1C)C=C(C(=C2)OC2(NC=CC=C2)C(=O)O)OC)C.N1(CCCC1)CCN.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=C2)N=N1.F[P-](F)(F)(F)(F)F.C(C)(C)N(C(C)C)CC>>BrC1=C(C=C(C=C1)NC1=NC2=C(N1C)C=C(C(=C2)OC2=CC(=NC=C2)C(=O)NCCN2CCCC2)OC)C | O[C:15]([C:10]1([O:9][c:8]2[c:3]([O:2][CH3:1])[cH:4][c:5]3[c:6]([cH:7]2)[n:26][c:27]([NH:28][c:29]2[cH:30][cH:31][c:32]([Br:33])[c:34]([CH3:35])[cH:36]2)[n:37]3[CH3:38])[NH:13][CH:12]=[CH:11][CH:14]=[CH:25]1)=[O:16].[NH2:17][CH2:18][CH2:19][N:20]1[CH2:21][CH2:22][CH2:23][CH2:24]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c... | COc1cc2c(cc1OC1(C(=O)O)C=CC=CN1)nc(Nc1ccc(Br)c(C)c1)n2C.NCCN1CCCC1 | COc1cc2c(cc1Oc1ccnc(C(=O)NCCN3CCCC3)c1)nc(Nc1ccc(Br)c(C)c1)n2C | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | 94a4caa66bccd8e91e7b580a9f4a3c5157ecfe3b07bd32b3f62ac4bbe934c768 | 41c50182f03618bf5d6f37d7b2d64e215c63c1f5eafd63156eb9376a8393c769 | O=C(NCCN1CCCC1)c1cc(Oc2ccc3[nH]c(Nc4ccccc4)nc3c2)ccn1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D4;+0:3]1(-[#8:4]-[c:5])-[CH;D2;+0:6]=[CH;D2;+0:7]-[CH;D2;+0:8]=[CH;D2;+0:9]-[NH;D2;+0:10]-1.[C:11]-[C:12]-[NH2;D1;+0:13]>>[C:11]-[C:12]-[NH;D2;+0:13]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:7]1:[cH;D2;+0:6]:[c;H0;D3;+0:3](-[#8:4]-[c:5]):[cH;D2;+0:8]:[cH;D2;+0:9]:[n;H0;D2;+0:10]:1 | null | [] | null | null | 16 | HOUR | To 4-(2-{[4-bromo-3-methylpheylamino)-6-methoxy-1-methylbenzimidazol-5-yloxy)pyridine-2-carboxylic acid(1 eq) in tetrahydrofuran was added 2-pyrrolidinylethylamine (2 eq), HBTU (2 eq) and N,N-diisopropylethylamine (4 eq) and stir at ambient temperature for 16 h. The mixture was then concentrated and partitioned between... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Carboxylic acid.Ether.Primary amine.Conjugated diene | Ether.Secondary amide | C1=CCNC=C1 | c1ccncc1 | c1ccncc1.C1CC[NH]C1.c1ccc2[nH]cnc2c1.c1ccccc1 | HO- | O1CCCC1 | null | 16 | COc1cc2c(cc1OC1(C(=O)O)C=CC=CN1)nc(Nc1ccc(Br)c(C)c1)n2C.NCCN1CCCC1>O1CCCC1>COc1cc2c(cc1Oc1ccnc(C(=O)NCCN3CCCC3)c1)nc(Nc1ccc(Br)c(C)c1)n2C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7dfe9877116b4fdba75da3ae47db6221 | Cc1ccc([N+](=O)[O-])cc1Br.OB(O)c1ccncc1Cl>>Cc1ccc([N+](=O)[O-])cc1-c1ccncc1Cl | BrC1=C(C=CC(=C1)[N+](=O)[O-])C.O.ClC=1C=NC=CC1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>>ClC=1C=NC=CC1C1=C(C=CC(=C1)[N+](=O)[O-])C | Br[c:10]1[c:2]([CH3:1])[cH:3][cH:4][c:5]([N+:6](=[O:7])[O-:8])[cH:9]1.OB(O)[c:11]1[cH:12][cH:13][n:14][cH:15][c:16]1[Cl:17]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([N+:6](=[O:7])[O-:8])[cH:9][c:10]1-[c:11]1[cH:12][cH:13][n:14][cH:15][c:16]1[Cl:17] | Cc1ccc([N+](=O)[O-])cc1Br.OB(O)c1ccncc1Cl | Cc1ccc([N+](=O)[O-])cc1-c1ccncc1Cl | null | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)[C-]1C=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2] | O.C(OC)COC | C-C Coupling | Suzuki coupling with boronic acids | 07e9b6e71d806aa92d4573f3838e77c7c8344de3e5d5735ebdb5fc6862ebf27d | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccncc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6].O-B(-O)-[c;H0;D3;+0:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1-[Cl;D1;H0:13]>>[C;D1;H3:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[c;H0;D3;+0:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1-[Cl;D1;H0:13]):[c:2]:[c:3] | null | [] | 90 | CELSIUS | null | null | Nitrogen was bubbled through a solution of 2-bromo-1-methyl-4-nitrobenzene (1 eq) in dimethoxyethane and water (3:1) for 0.5 h. Bis(diphenylphosphino)ferrocene Palladium(II)chloride (0.05 eq) followed by 3-chloro-4-pyridine boronic acid hydrate (1 eq) and sodium carbonate (3 eq) was added and the mixture was heated to ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | HBr.B | [Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)[C-]1C=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2].O.C(OC)COC | 90 | null | Cc1ccc([N+](=O)[O-])cc1Br.OB(O)c1ccncc1Cl>[Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)[C-]1C=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2].O.C(OC)COC>Cc1ccc([N+](=O)[O-])cc1-c1ccncc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a524bdbd092c48ae93d277d963df4803 | Cc1ccc([N+](=O)[O-])cc1-c1ccncc1Cl>>Cc1ccc(N)cc1-c1ccncc1Cl | ClC=1C=NC=CC1C1=C(C=CC(=C1)[N+](=O)[O-])C.C([O-])([O-])=O.[Na+].[Na+]>>ClC=1C=NC=CC1C=1C=C(C=CC1C)N | O=[N+:6]([O-])[c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:8](-[c:9]2[cH:10][cH:11][n:12][cH:13][c:14]2[Cl:15])[cH:7]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH2:6])[cH:7][c:8]1-[c:9]1[cH:10][cH:11][n:12][cH:13][c:14]1[Cl:15] | Cc1ccc([N+](=O)[O-])cc1-c1ccncc1Cl | Cc1ccc(N)cc1-c1ccncc1Cl | null | [Fe] | C(C)(=O)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(-c2ccncc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 6 | HOUR | To the mixture containing 3-chloro-4-(2-methyl-5-nitrophenyl)pyridine in acetic acid was added Fe dust (5 eq) and the resulting mixture was stirred at ambient temperature for 6 h. To it was then added saturated sodium carbonate to bring it to neutral pH and extracted with ethyl acetate. The organic layer was washed wit... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccncc1 | Other | [Fe].C(C)(=O)O | null | 6 | Cc1ccc([N+](=O)[O-])cc1-c1ccncc1Cl>[Fe].C(C)(=O)O>Cc1ccc(N)cc1-c1ccncc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-47ebf50a5cb54e36b6b88c98a9f9c59c | CNC(=O)c1cccc(Cl)c1.CNc1cc(OC)c(O)cc1[N+](=O)[O-]>>CNC(=O)c1cc(Oc2cc([N+](=O)[O-])c(NC)cc2OC)ccn1 | ClC=1C=C(C=CC1)C(=O)NC.C([O-])([O-])=O.[K+].[K+].COC1=C(C=C(C(=C1)NC)[N+](=O)[O-])O.CC(C)([O-])C.[K+].CN(C(C)=O)C>>COC1=C(OC2=CC(=NC=C2)C(=O)NC)C=C(C(=C1)NC)[N+](=O)[O-] | Cl[c:7]1[cH:6][c:5]([C:3]([NH:2][CH3:1])=[O:4])c[cH:23][cH:22]1.[OH:8][c:9]1[cH:10][c:11]([N+:12](=[O:13])[O-:14])[c:15]([NH:16][CH3:17])[cH:18][c:19]1[O:20][CH3:21]>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([O:8][c:9]2[cH:10][c:11]([N+:12](=[O:13])[O-:14])[c:15]([NH:16][CH3:17])[cH:18][c:19]2[O:20][CH3:21])[cH:22][... | CNC(=O)c1cccc(Cl)c1.CNc1cc(OC)c(O)cc1[N+](=O)[O-] | CNC(=O)c1cc(Oc2cc([N+](=O)[O-])c(NC)cc2OC)ccn1 | null | null | null | Protection | OtherReaction | f0023f5cb78e4f43639596fb9d7e792c21b5d63a2c4e24a596c544a93eb8f3cf | cf1075be1c1ecf3bb8058899ddc12870a38487ecc9322d6e66205e53a46d9b16 | c1ccc(Oc2ccncc2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[cH;D2;+0:3]:c:[c;H0;D3;+0:4](-[C:5](=[O;D1;H0:6])-[#7:7]-[C;D1;H3:8]):[c:9]:1.[OH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C;D1;H3:8]-[#7:7]-[C:5](=[O;D1;H0:6])-[c;H0;D3;+0:4]1:[#7;a:14]:[cH;D2;+0:3]:[c:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:10]-[c:11](:[c:12]):[c:13]):[c:9]:1 | null | [] | null | null | null | null | To a stirred solution of 2-methoxy-4-(methylamino)-5-nitrophenol(1 eq) in N,N-dimethylacetamide was added potassium-t-butoxide (1.2 eq) and continued stirring at ambient temperature until it solidified. To it was then added (3-chlorophenyl)-N-methylcarboxamide (1 eq) and anhydrous potassium carbonate (1 eq) and the res... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccccc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | HCl | null | null | null | CNC(=O)c1cccc(Cl)c1.CNc1cc(OC)c(O)cc1[N+](=O)[O-]>>CNC(=O)c1cc(Oc2cc([N+](=O)[O-])c(NC)cc2OC)ccn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ece00de1a8ae45ebb41ea31a86d1e23b | CNC(=O)c1cc(Oc2cc([N+](=O)[O-])c(NC)cc2OC)ccn1>>CNC(=O)c1cc(Oc2cc(N)c(NC)cc2OC)ccn1 | COC1=C(OC2=CC(=NC=C2)C(=O)NC)C=C(C(=C1)NC)[N+](=O)[O-]>>NC=1C=C(OC2=CC(=NC=C2)C(=O)NC)C(=CC1NC)OC | O=[N+:12]([O-])[c:11]1[cH:10][c:9]([O:8][c:7]2[cH:6][c:5]([C:3]([NH:2][CH3:1])=[O:4])[n:22][cH:21][cH:20]2)[c:17]([O:18][CH3:19])[cH:16][c:13]1[NH:14][CH3:15]>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([O:8][c:9]2[cH:10][c:11]([NH2:12])[c:13]([NH:14][CH3:15])[cH:16][c:17]2[O:18][CH3:19])[cH:20][cH:21][n:22]1 | CNC(=O)c1cc(Oc2cc([N+](=O)[O-])c(NC)cc2OC)ccn1 | CNC(=O)c1cc(Oc2cc(N)c(NC)cc2OC)ccn1 | null | [Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(Oc2ccncc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A solution of {4-[2-methoxy-4-(methylamino)-5-nitrophenoxy](2-pyridyl)}-N-methylcarboxamide. In methanol was hydrogenated with 10% Pd/C. The catalyst was filtered off and the solvent was concentrated to yield {4-[3-amino-6-methoxy-4-(methylamino)phenoxy](2-pyridyl)}-N-methylcarboxamide. MS :MH+: 302.
Conditions: See re... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccncc1.c1ccccc1 | Other | [Pd].CO | null | null | CNC(=O)c1cc(Oc2cc([N+](=O)[O-])c(NC)cc2OC)ccn1>[Pd].CO>CNC(=O)c1cc(Oc2cc(N)c(NC)cc2OC)ccn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f7c91842ad414fc4bf824d4efcc8346b | COC(=O)c1cncc(Oc2ccc([N+](=O)[O-])cc2)c1>>COC(=O)c1cncc(Oc2ccc(N)cc2)c1 | COC(=O)C=1C=NC=C(C1)OC1=CC=C(C=C1)[N+](=O)[O-]>>COC(=O)C=1C=NC=C(C1)OC1=CC=C(C=C1)N | O=[N+:15]([O-])[c:14]1[cH:13][cH:12][c:11]([O:10][c:9]2[cH:8][n:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:18]2)[cH:17][cH:16]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7][cH:8][c:9]([O:10][c:11]2[cH:12][cH:13][c:14]([NH2:15])[cH:16][cH:17]2)[cH:18]1 | COC(=O)c1cncc(Oc2ccc([N+](=O)[O-])cc2)c1 | COC(=O)c1cncc(Oc2ccc(N)cc2)c1 | null | [Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(Oc2cccnc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The mixture containing methyl-5-(4-nitrophenoxy)pyridine-3-carboxylate in methanol with catalytic amount of 10% Pd/C was hydrogenated to yield methyl5-[4-aminophenoxy]pyridine-3-carboxylate. MS: MH+=244.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccncc1.c1ccccc1 | Other | [Pd].CO | null | null | COC(=O)c1cncc(Oc2ccc([N+](=O)[O-])cc2)c1>[Pd].CO>COC(=O)c1cncc(Oc2ccc(N)cc2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bb9a850ef83945038bd3835d81d78414 | COC(=O)c1cncc(Oc2ccc(NC(=O)C(F)(F)F)c([N+](=O)[O-])c2)c1.COS(=O)(=O)OC>>CNc1ccc(Oc2ccncc2C(=O)OC)cc1[N+](=O)[O-] | S(=O)(=O)(OC)OC.COC(=O)C=1C=NC=C(C1)OC1=CC(=C(C=C1)NC(C(F)(F)F)=O)[N+](=O)[O-].C(C)#N.[OH-].[Na+].C1(=CC=CC=C1)C>>COC(=O)C=1C=NC=CC1OC1=CC(=C(C=C1)NC)[N+](=O)[O-] | O=C(C(F)(F)F)[NH:2][c:3]1[cH:4][cH:5][c:6]([O:7][c:8]2[cH:9][c:13]([C:14](=[O:15])[O:16][CH3:17])[cH:12][n:11][cH:10]2)[cH:18][c:19]1[N+:20](=[O:21])[O-:22].COS(=O)(=O)O[CH3:1]>>[CH3:1][NH:2][c:3]1[cH:4][cH:5][c:6]([O:7][c:8]2[cH:9][cH:10][n:11][cH:12][c:13]2[C:14](=[O:15])[O:16][CH3:17])[cH:18][c:19]1[N+:20](=[O:21])[... | COC(=O)c1cncc(Oc2ccc(NC(=O)C(F)(F)F)c([N+](=O)[O-])c2)c1.COS(=O)(=O)OC | CNc1ccc(Oc2ccncc2C(=O)OC)cc1[N+](=O)[O-] | null | [Cl-].C(C1=CC=CC=C1)[N+](C)(C)C | null | Functional Group Addition | OtherReaction | 4e8b58513939f305220516ba66a29c403383c4fdcb5862eba3a3a67db4b3baff | d1cd17b8c44f4dd4dd342fb29e5927608ceb97f81a8ca71bbe503b983f1461f9 | c1ccc(Oc2ccncc2)cc1 | C-O-S(=O)(=O)-O-[CH3;D1;+0:1].F-C(-F)(-F)-C(=O)-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[c;H0;D3;+0:10]1:[c:11]:[#7;a:12]:[cH;D2;+0:13]:[c;H0;D3;+0:14](-[#8:15]-[c:16]):[cH;D2;+0:17]:1>>[C;D1;H3:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[c;H0;D3;+0:10]1:[c:11]:[#7;a:12]:[cH;D2;+0:13]:[cH;D2;+0:17]:[... | null | [] | null | null | 8 | HOUR | To the solution of the methyl5-[3-nitro-4-(2,2,2-trifluroacetylamino)phenoxy]-pyridine-3-carboxylate (1 eq) in a mixture of toluene, acetonitrile and sodium hydroxide solution (50%) was added benzyltrimethylammonium chloride (1 eq) and dimethyl sulfate (1.2 eq). The biphasic mixture was stirred overnight at room temper... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Ester.Ether.Secondary amide | Ester.Ether.Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1 | HF | [Cl-].C(C1=CC=CC=C1)[N+](C)(C)C | null | 8 | COC(=O)c1cncc(Oc2ccc(NC(=O)C(F)(F)F)c([N+](=O)[O-])c2)c1.COS(=O)(=O)OC>[Cl-].C(C1=CC=CC=C1)[N+](C)(C)C>CNc1ccc(Oc2ccncc2C(=O)OC)cc1[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f88b00a854de4ae3bb737e32aeb6ea63 | CNc1ccc(Oc2cncc(C(=O)OC)c2)cc1N.S=C=Nc1ccc(Br)cc1>>COC(=O)c1cncc(Oc2ccc3c(c2)nc(Nc2ccc(Br)cc2)n3C)c1 | CI.COC(=O)C=1C=NC=C(C1)OC1=CC(=C(C=C1)NC)N.BrC1=CC=C(C=C1)N=C=S>>COC(=O)C=1C=NC=C(C1)OC1=CC2=C(N(C(=N2)NC2=CC=C(C=C2)Br)C)C=C1 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7][cH:8][c:9]([O:10][c:11]2[cH:12][cH:13][c:14]([NH:27][CH3:28])[c:15]([NH2:17])[cH:16]2)[cH:29]1.S=[C:18]=[N:19][c:20]1[cH:21][cH:22][c:23]([Br:24])[cH:25][cH:26]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7][cH:8][c:9]([O:10][c:11]2[cH:12][cH:13][c:14]3[c:15]([cH:16]2)[n:17][c:1... | CNc1ccc(Oc2cncc(C(=O)OC)c2)cc1N.S=C=Nc1ccc(Br)cc1 | COC(=O)c1cncc(Oc2ccc3c(c2)nc(Nc2ccc(Br)cc2)n3C)c1 | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | d7416f6ffd0cf3a591ff39bb82719e0121b02095a886f4bf34a4bce30d165f53 | c2745d0d96944794048cb0a435469fb3c0efa689f6d5e8d4fd6447372cabc5f8 | c1ccc(Nc2nc3cc(Oc4cccnc4)ccc3[nH]2)cc1 | S=[C;H0;D2;+0:1]=[N;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10](-[NH2;D1;+0:11]):[c:12]>>[C;D1;H3:6]-[n;H0;D3;+0:7]1:[c:8](:[c:9]):[c:10](:[c:12]):[n;H0;D2;+0:11]:[c;H0;D3;+0:1]:1-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | 2 | HOUR | A solution of the methyl5-[3-amino-4-(methylamino)phenoxy]pyridine-3-carboxylate (1 eq) in methanol (8 ml) was treated with 4-bromophenylisothiocyanate (1 eq) and stirred at 60° C.–65° C. for 2 hours. The reaction mixture was cooled down to room temperature and methyl iodide (1 eq) was added and stirred overnight at 60... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine.Isothiocyanate | Secondary amine | c1ccccc1 | c1ccc2nc[nH]c2c1 | c1ccncc1.c1ccc2nc[nH]c2c1.c1ccccc1 | Other | CO | null | 2 | CNc1ccc(Oc2cncc(C(=O)OC)c2)cc1N.S=C=Nc1ccc(Br)cc1>CO>COC(=O)c1cncc(Oc2ccc3c(c2)nc(Nc2ccc(Br)cc2)n3C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3c5e0b6c49554f4aae13c05d3f715346 | CN.COC(=O)c1cncc(Oc2ccc3c(c2)nc(Nc2ccc(Br)cc2)n3C)c1>>CNC(=O)c1cncc(Oc2ccc3c(c2)nc(Nc2ccc(Br)cc2)n3C)c1 | COC(=O)C=1C=NC=C(C1)OC1=CC2=C(N(C(=N2)NC2=CC=C(C=C2)Br)C)C=C1.CN>>BrC1=CC=C(C=C1)NC1=NC2=C(N1C)C=CC(=C2)OC=2C=C(C=NC2)C(=O)NC | [CH3:1][NH2:2].CO[C:3](=[O:4])[c:5]1[cH:6][n:7][cH:8][c:9]([O:10][c:11]2[cH:12][cH:13][c:14]3[c:15]([cH:16]2)[n:17][c:18]([NH:19][c:20]2[cH:21][cH:22][c:23]([Br:24])[cH:25][cH:26]2)[n:27]3[CH3:28])[cH:29]1>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][n:7][cH:8][c:9]([O:10][c:11]2[cH:12][cH:13][c:14]3[c:15]([cH:16]2)[n:17][c... | CN.COC(=O)c1cncc(Oc2ccc3c(c2)nc(Nc2ccc(Br)cc2)n3C)c1 | CNC(=O)c1cncc(Oc2ccc3c(c2)nc(Nc2ccc(Br)cc2)n3C)c1 | null | null | null | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | c1ccc(Nc2nc3cc(Oc4cccnc4)ccc3[nH]2)cc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].[C;D1;H3:8]-[NH2;D1;+0:9]>>[C;D1;H3:8]-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | null | [] | null | null | null | null | To a solution of methyl5-{2-[(4-bromophenyl)amino]-1-methylbenzimidazol-5-yloxy}pyridine-3-carboxylate in added methylamine and the resulting mixture was stirred at ambient temperature for 16 h. It was then concentrated and purified by preparative chromatography to yield (5-{2-[(4-bromophenyl)amino]-1-methylbenzimidazo... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccc2nc[nH]c2c1.c1ccccc1 | HO- | null | null | null | CN.COC(=O)c1cncc(Oc2ccc3c(c2)nc(Nc2ccc(Br)cc2)n3C)c1>>CNC(=O)c1cncc(Oc2ccc3c(c2)nc(Nc2ccc(Br)cc2)n3C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0d4cc39a59824b21916c9f11a96a886e | CNC.O=[N+]([O-])c1ccc(Cl)nc1>>CN(C)c1ccc([N+](=O)[O-])cn1 | ClC1=NC=C(C=C1)[N+](=O)[O-].CNC.O>>CN(C1=NC=C(C=C1)[N+](=O)[O-])C | [CH3:1][NH:2][CH3:3].Cl[c:4]1[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][n:12]1>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][n:12]1 | CNC.O=[N+]([O-])c1ccc(Cl)nc1 | CN(C)c1ccc([N+](=O)[O-])cn1 | null | null | CN1CCCC1=O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | a0163952e7575991d15970b416e74bb56cf346e5420a42d8fb74b35140502d0d | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccncc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[NH;D2;+0:7]-[C;D1;H3:8]>>[C;D1;H3:6]-[N;H0;D3;+0:7](-[C;D1;H3:8])-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | 2-Chloro-5-nitropyridine (1.0 eq) and dimethylamine (2 M in EtOH, 4.6 eq) in NMP were heated for 2 h at 100° C. The solution was then poured slowly into H2O. The filtrate that formed was filtered and dried to give 2-(dimethylamino)-5-nitropyridine.
Conditions: See reaction.notes.procedure_details.
Workup: The filtrate ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccncc1 | c1ccncc1 | c1ccncc1 | HCl | CN1CCCC1=O | null | null | CNC.O=[N+]([O-])c1ccc(Cl)nc1>CN1CCCC1=O>CN(C)c1ccc([N+](=O)[O-])cn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-646ee376cd9a44aaa4321c391e2fa201 | CN(C)c1ccc([N+](=O)[O-])cn1>>CN(C)c1ccc(N)cn1 | CN(C1=NC=C(C=C1)[N+](=O)[O-])C>>CN(C1=NC=C(C=C1)N)C | O=[N+:8]([O-])[c:7]1[cH:6][cH:5][c:4]([N:2]([CH3:1])[CH3:3])[n:10][cH:9]1>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([NH2:8])[cH:9][n:10]1 | CN(C)c1ccc([N+](=O)[O-])cn1 | CN(C)c1ccc(N)cn1 | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccncc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6] | null | [] | null | null | 8 | HOUR | A mixture of 2-(dimethylamino)-5-nitropyridine (1 eq) and 5% palladium on carbon (0.3 eq) in ethanol was stirred at room temperature and flushed with nitrogen. The reaction vessel was evacuated and purged with hydrogen three times. The reaction mixture was left under an atmosphere of hydrogen overnight. Nitrogen was fl... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccncc1 | Other | [Pd].C(C)O | null | 8 | CN(C)c1ccc([N+](=O)[O-])cn1>[Pd].C(C)O>CN(C)c1ccc(N)cn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8f82121579ef4eca9d6cf6b432beefbd | CNC(=O)c1cc(Oc2ccc(N)c([N+](=O)[O-])c2)ccn1.Nc1ccc(O)cc1[N+](=O)[O-]>>O=[N+]([O-])Nc1ccccc1 | C(Cl)Cl.NC1=C(C=C(C=C1)O)[N+](=O)[O-].NC1=C(C=C(OC2=CC(=NC=C2)C(=O)NC)C=C1)[N+](=O)[O-].C([O-])([O-])=O.[Na+].[Na+]>>[N+](=O)([O-])NC1=CC=CC=C1 | CNC(=O)c1cc(Oc2ccc(N)c([N+:2](=[O:1])[O-:3])c2)ccn1.O=[N+]([O-])[c:10]1[c:5]([NH2:4])[cH:6][cH:7][c:8](O)[cH:9]1>>[O:1]=[N+:2]([O-:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1 | CNC(=O)c1cc(Oc2ccc(N)c([N+](=O)[O-])c2)ccn1.Nc1ccc(O)cc1[N+](=O)[O-] | O=[N+]([O-])Nc1ccccc1 | null | null | O.COCCOC.O.C(C)(=O)OCC | Functional Group Addition | OtherReaction | 86bc2645c62da628c1b0f146568ee6ae2487f0b469dcadde2d0b02e61a45383c | 612c2322ffd5d165f8c3c7313c038638c8ba2e78bb7f92591a7ca3386f36d8f5 | c1ccccc1 | C-N-C(=O)-c1:c:c(-O-c2:c:c:c(-N):c(-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3]):c:2):c:c:n:1.O-[c;H0;D3;+0:4]1:[c:5]:[c:6]:[c:7](-[NH2;D1;+0:8]):[c;H0;D3;+0:9](-[N+](=O)-[O-]):[c:10]:1>>[O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[NH;D2;+0:8]-[c:7]1:[c:6]:[c:5]:[cH;D2;+0:4]:[c:10]:[cH;D2;+0:9]:1 | null | [] | 100 | CELSIUS | null | null | A solution of 5 (1 eq), 6 (1 eq), and sodium carbonate (1.2 eq) in DME/H2O (3:1) was degassed by bubbling argon through the solution for 10 minutes. Pd(II)(dppf)Cl2.MeCl2 (0.1 eq) was added to the reaction solution and the reaction was sealed. The reaction was heated at 100° C. overnight. The reaction was cooled to RT ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Nitro group.Nitro group.Secondary amide.Aromatic alcohol.Primary amine.Primary amine | Hydrazine | c1ccncc1.c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | O.COCCOC.O.C(C)(=O)OCC | 100 | null | CNC(=O)c1cc(Oc2ccc(N)c([N+](=O)[O-])c2)ccn1.Nc1ccc(O)cc1[N+](=O)[O-]>O.COCCOC.O.C(C)(=O)OCC>O=[N+]([O-])Nc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-33389ec7e72c4df3b9b8deccba4fd745 | CC(C)c1cccc(Nc2nc3cc(Oc4ccnc(C(=O)NCCN)c4)ccc3n2C)c1.O=S(=O)(Cl)Cc1ccccc1>>CC(C)c1cccc(Nc2nc3cc(Oc4ccnc(C(=O)NCCNS(=O)(=O)Cc5ccccc5)c4)ccc3n2C)c1 | C1(=CC=CC=C1)CS(=O)(=O)Cl.NCCNC(=O)C1=NC=CC(=C1)OC1=CC2=C(N(C(=N2)NC2=CC(=CC=C2)C(C)C)C)C=C1.C(=O)([O-])[O-].[K+].[K+].C(C)#N>>C1(=CC=CC=C1)CS(=O)(=O)NCCNC(=O)C1=NC=CC(=C1)OC1=CC2=C(N(C(=N2)NC2=CC(=CC=C2)C(C)C)C)C=C1 | [CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([NH:9][c:10]2[n:11][c:12]3[cH:13][c:14]([O:15][c:16]4[cH:17][cH:18][n:19][c:20]([C:21](=[O:22])[NH:23][CH2:24][CH2:25][NH2:26])[cH:37]4)[cH:38][cH:39][c:40]3[n:41]2[CH3:42])[cH:43]1.Cl[S:27](=[O:28])(=[O:29])[CH2:30][c:31]1[cH:32][cH:33][cH:34][cH:35][cH:36]1>>[CH3:1]... | CC(C)c1cccc(Nc2nc3cc(Oc4ccnc(C(=O)NCCN)c4)ccc3n2C)c1.O=S(=O)(Cl)Cc1ccccc1 | CC(C)c1cccc(Nc2nc3cc(Oc4ccnc(C(=O)NCCNS(=O)(=O)Cc5ccccc5)c4)ccc3n2C)c1 | null | null | O | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C(NCCNS(=O)(=O)Cc1ccccc1)c1cc(Oc2ccc3[nH]c(Nc4ccccc4)nc3c2)ccn1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[c:5] | null | [] | null | null | 1 | HOUR | To a mixture containing 4-[2-(3-Isopropyl-phenylamino)-1-methyl-1H-benzoimidazol-5-yloxy]-pyridine-2-carboxylic acid (2-amino-ethyl)-amide (1 eq) (prepared using previously described example 3), K2CO3 (5 eq), (0.2 M in a 5:1 mixture of acetonitrile and water) were added α-toluenesulfonyl chloride (1 eq) via syringe. Th... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccc2nc[nH]c2c1.c1ccncc1.c1ccccc1 | HCl | O | null | 1 | CC(C)c1cccc(Nc2nc3cc(Oc4ccnc(C(=O)NCCN)c4)ccc3n2C)c1.O=S(=O)(Cl)Cc1ccccc1>O>CC(C)c1cccc(Nc2nc3cc(Oc4ccnc(C(=O)NCCNS(=O)(=O)Cc5ccccc5)c4)ccc3n2C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d83a7c5eff9f4444938f5ef737900e22 | CCO.CNC(=O)c1cc(Oc2cc([N+](=O)[O-])c(NC)cc2OC)ccn1>>Nc1ccc(OCCCN2CCCC2)cc1N | COC1=C(OC2=CC(=NC=C2)C(=O)NC)C=C(C(=C1)NC)[N+](=O)[O-].CCO>>N1(CCCC1)CCCOC=1C=C(C(=CC1)N)N | O[CH2:7][CH3:8].C[NH:17][c:16]1[c:2]([N+:1](=O)[O-])[cH:3][c:4]([O:6]c2c[c:9](C(=O)N[CH3:11])[n:10][cH:13][cH:12]2)[c:5](O[CH3:14])[cH:15]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([O:6][CH2:7][CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][CH2:13][CH2:14]2)[cH:15][c:16]1[NH2:17] | CCO.CNC(=O)c1cc(Oc2cc([N+](=O)[O-])c(NC)cc2OC)ccn1 | Nc1ccc(OCCCN2CCCC2)cc1N | null | [Pd] | null | Functional Group Interconversion | OtherReaction | 5c8f9143e2e2766e0dc505bfc1f92c62f37241f237126605047aedf8c18ae9ef | 20fd7ea1b0d0bd4bb0c0bb94c83c721be4371db6d08d2db71c2fe642fc3b6a26 | c1ccc(OCCCN2CCCC2)cc1 | C-[NH;D2;+0:1]-[c:2]1:[c:3]:[c;H0;D3;+0:4](-O-[CH3;D1;+0:5]):[c;H0;D3;+0:6](-[O;H0;D2;+0:7]-c2:[cH;D2;+0:8]:[cH;D2;+0:9]:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-C(=O)-N-[CH3;D1;+0:12]):c:2):[c:13]:[c:14]:1-[N+;H0;D3:15](=O)-[O-].O-[CH2;D2;+0:16]-[CH3;D1;+0:17]>>[NH2;D1;+0:1]-[c:2]1:[c:3]:[c;H0;D3;+0:4](-[O;H0;D2;+0:7]-[CH2;D2... | null | [] | null | null | 18 | HOUR | To a solution 2-Nitro-4-(3-pyrrolidinylpropoxy)phenylamine 1 in EtOH, Pd/C (0.1 eq) is added. The reaction vessel is repeatedly purged (×3) with nitrogen, and then stirred under a hydrogen atmosphere for 18 h. The product is filtered through a Celite plug, and the plug washed with 25 mL of EtOH, to yield 2. LCMS 236.2 ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Nitro group.Secondary amide.Primary alcohol.Secondary amine | Ether.Primary amine.Primary amine.Tertiary amine | c1ccccc1.c1ccncc1 | c1ccccc1.C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1 | HO- | [Pd] | null | 18 | CCO.CNC(=O)c1cc(Oc2cc([N+](=O)[O-])c(NC)cc2OC)ccn1>[Pd]>Nc1ccc(OCCCN2CCCC2)cc1N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-93bd734cd93549c9ba3d48b9626f217f | CN1CCNCC1.Nc1cc(F)ccc1[N+](=O)[O-]>>CN1CCN(c2ccc([N+](=O)[O-])c(N)c2)CC1 | CN1CCNCC1.CN1CCCC1=O.C(C)N(CC)CC.FC=1C=CC(=C(C1)N)[N+](=O)[O-]>>CN1CCN(CC1)C=1C=CC(=C(C1)N)[N+](=O)[O-] | [CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:16][CH2:17]1.F[c:6]1[cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[c:13]([NH2:14])[cH:15]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[c:13]([NH2:14])[cH:15]2)[CH2:16][CH2:17]1 | CN1CCNCC1.Nc1cc(F)ccc1[N+](=O)[O-] | CN1CCN(c2ccc([N+](=O)[O-])c(N)c2)CC1 | null | null | O | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | d687b31bdda9f407fdde6ca57e67eee0681e173646c617afef7770c56d05bab9 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | null | [] | null | null | 12 | HOUR | A solution of N-methylpiperazine (1.0 eq), NMP, triethylamine (3.0 eq) and 5-fluoro-2-nitrophenylamine (1.0 eq) were heated at 90° C. for 1 hours. The reaction was allowed to cool to room temperature and then poured into water and let stand for 12 hours. The resulting solid was collected and dried and utilized without ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | HF | O | null | 12 | CN1CCNCC1.Nc1cc(F)ccc1[N+](=O)[O-]>O>CN1CCN(c2ccc([N+](=O)[O-])c(N)c2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9dd8ff5a8b8b41219f159bbebd81ad04 | CNC(=O)c1cc(Oc2cc([N+](=O)[O-])c(NC)cc2OC)ccn1.S=C=Nc1cccc(Oc2ccccc2)c1>>CNC(=O)c1cc(Oc2ccc3c(c2)nc(Nc2cccc(Oc4ccccc4)c2)n3C)ccn1 | O(C1=CC=CC=C1)C=1C=C(C=CC1)N=C=S.COC1=C(OC2=CC(=NC=C2)C(=O)NC)C=C(C(=C1)NC)[N+](=O)[O-].CI>>CNC(=O)C1=NC=CC(=C1)OC1=CC2=C(N(C(=N2)NC2=CC(=CC=C2)OC2=CC=CC=C2)C)C=C1 | CO[c:10]1[c:9]([O:8][c:7]2[cH:6][c:5]([C:3]([NH:2][CH3:1])=[O:4])[n:35][cH:34][cH:33]2)[cH:14][c:13]([N+:15](=O)[O-])[c:12]([NH:31][CH3:32])[cH:11]1.S=[C:16]=[N:17][c:18]1[cH:19][cH:20][cH:21][c:22]([O:23][c:24]2[cH:25][cH:26][cH:27][cH:28][cH:29]2)[cH:30]1>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([O:8][c:9]2[cH:10... | CNC(=O)c1cc(Oc2cc([N+](=O)[O-])c(NC)cc2OC)ccn1.S=C=Nc1cccc(Oc2ccccc2)c1 | CNC(=O)c1cc(Oc2ccc3c(c2)nc(Nc2cccc(Oc4ccccc4)c2)n3C)ccn1 | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | e01045c6582f8094924aa12a0ae4155a5e203c3b3b57eaca9716db280dbf92a5 | 3df5785608eefdb0973d9c896a6050fedd9fdf25c115a747f31ba5969e559ebc | c1ccc(Oc2cccc(Nc3nc4cc(Oc5ccncc5)ccc4[nH]3)c2)cc1 | C-O-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[NH;D2;+0:4]-[C;D1;H3:5]):[c:6](-[N+;H0;D3:7](=O)-[O-]):[c:8]:[c:9]:1-[#8:10].S=[C;H0;D2;+0:11]=[N;H0;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[#8:10]-[c:9]1:[c:8]:[c:6]2:[n;H0;D2;+0:7]:[c;H0;D3;+0:11](-[NH;D2;+0:12]-[c:13](:[c:14]):[c:15]):[n;H0;D3;+0:4](-[C;D1;H3:5]):[c:3]:2:[c:2]:[cH;D2;+0:... | null | [] | null | null | 8 | HOUR | A 1 dram vial was charged with a solution of 3-phenoxyphenylisothiocyanate (23 mg, 0.1 mmol), diamine 1 (27 mg, 0.1 mmol), and MeOH (0.5 mL) and the reaction was shaken at rt overnight. Methyl iodide (8 uL, 0.13 mmol) was added and the mixture shaken overnight. The reaction was concentrated and the resulting residue pu... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Nitro group.Secondary amine.Isothiocyanate | Secondary amine | c1ccccc1 | c1ccc2nc[nH]c2c1 | c1ccncc1.c1ccc2nc[nH]c2c1.c1ccccc1.c1ccccc1 | Other | CO | null | 8 | CNC(=O)c1cc(Oc2cc([N+](=O)[O-])c(NC)cc2OC)ccn1.S=C=Nc1cccc(Oc2ccccc2)c1>CO>CNC(=O)c1cc(Oc2ccc3c(c2)nc(Nc2cccc(Oc4ccccc4)c2)n3C)ccn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-578aafd6133147929ebb566b7654c689 | CNC(=O)c1cc(Oc2cc([N+](=O)[O-])c(NC)cc2OC)ccn1.O=Cc1ccc(Br)cc1>>CNC(=O)c1cc(Oc2ccc3c(c2)nc(-c2ccc(Br)cc2)n3C)ccn1 | COC1=C(OC2=CC(=NC=C2)C(=O)NC)C=C(C(=C1)NC)[N+](=O)[O-].BrC1=CC=C(C=O)C=C1>>CNC(=O)C1=NC=CC(=C1)OC1=CC2=C(N(C(=N2)C2=CC=C(C=C2)Br)C)C=C1 | CO[c:10]1[c:9]([O:8][c:7]2[cH:6][c:5]([C:3]([NH:2][CH3:1])=[O:4])[n:28][cH:27][cH:26]2)[cH:14][c:13]([N+:15](=O)[O-])[c:12]([NH:24][CH3:25])[cH:11]1.O=[CH:16][c:17]1[cH:18][cH:19][c:20]([Br:21])[cH:22][cH:23]1>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14]2)[n:15][c:16](-[c:... | CNC(=O)c1cc(Oc2cc([N+](=O)[O-])c(NC)cc2OC)ccn1.O=Cc1ccc(Br)cc1 | CNC(=O)c1cc(Oc2ccc3c(c2)nc(-c2ccc(Br)cc2)n3C)ccn1 | null | null | O1CCOCC1 | Aromatic Heterocycle Formation | OtherReaction | e451cfd55755e6b1044f1e94003171c7580983989ef49f333fe1628342897349 | 106c47f7abe58d817988fc6d996094606a2af5ef5c09dd35fea21b01eadf0288 | c1ccc(-c2nc3cc(Oc4ccncc4)ccc3[nH]2)cc1 | C-O-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[NH;D2;+0:4]-[C;D1;H3:5]):[c:6](-[N+;H0;D3:7](=O)-[O-]):[c:8]:[c:9]:1-[#8:10].O=[CH;D2;+0:11]-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[#8:10]-[c:9]1:[c:8]:[c:6]2:[n;H0;D2;+0:7]:[c;H0;D3;+0:11](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]):[n;H0;D3;+0:4](-[C;D1;H3:5]):[c:3]:2:[c... | null | [] | 100 | CELSIUS | null | null | A mixture of diamine 1 (137 mg, 0.36 mmol) and 4-bromobenzaldehyde (66 mg, 0.50 mmol) in dry dioxane (2 mL) was heated to 100° C. for 16 h. The reaction mixture was allowed to cool to rt and was then concentrated. The resulting residue was purified by reverse phase HPLC to finish 2 as the TFA salt: LCMS m/z 437.1, tR=2... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ether.Nitro group.Secondary amine | null | c1ccccc1 | c1ccc2nc[nH]c2c1 | c1ccncc1.c1ccc2nc[nH]c2c1.c1ccccc1 | HO- | O1CCOCC1 | 100 | null | CNC(=O)c1cc(Oc2cc([N+](=O)[O-])c(NC)cc2OC)ccn1.O=Cc1ccc(Br)cc1>O1CCOCC1>CNC(=O)c1cc(Oc2ccc3c(c2)nc(-c2ccc(Br)cc2)n3C)ccn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cc10fa94f3074812be93f370e5820499 | C1COOOC1.CC(=O)O[BH-](OC(C)=O)OC(C)=O.Nc1ccccc1-c1ccccc1>>C=C(c1ccccc1)C1COC2(CCC(Nc3ccccc3-c3ccccc3)CC2)OO1 | O.O1OOCCC1.NC1=C(C=CC=C1)C1=CC=CC=C1.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>C1(=C(C=CC=C1)NC1CCC2(OCC(OO2)C(=C)C2=CC=CC=C2)CC1)C1=CC=CC=C1 | [CH2:2]1[CH2:9][CH2:10][O:11][O:32][O:31]1.O=[C:1](O[BH-](O[C:8](=O)[CH3:3])O[C:15](=O)[CH3:29])[CH3:13].[NH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][c:22]1-[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[CH2:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[CH:9]1[CH2:10][O:11][C:12]2([CH2:13][CH2:14][CH:15]([NH:16][c:17]3... | C1COOOC1.CC(=O)O[BH-](OC(C)=O)OC(C)=O.Nc1ccccc1-c1ccccc1 | C=C(c1ccccc1)C1COC2(CCC(Nc3ccccc3-c3ccccc3)CC2)OO1 | null | null | ClCCl | Aromatic Heterocycle Formation | OtherReaction | e1ccf6effe82ed570627042fc7a202dfeff5db514191bfb6c0626713ad8ba185 | ab2c134b6353bbc2872cad7da7c653ff912491653702c9701526cbe073308159 | C=C(c1ccccc1)C1COC2(CCC(Nc3ccccc3-c3ccccc3)CC2)OO1 | O=[C;H0;D3;+0:1](-[CH3;D1;+0:2])-O-[BH-](-O-[C;H0;D3;+0:3](=O)-[CH3;D1;+0:4])-O-[C;H0;D3;+0:5](=O)-[CH3;D1;+0:6].[C:7]1-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[O;H0;D2;+0:10]-[O;H0;D2;+0:11]-[O;H0;D2;+0:12]-1.[NH2;D1;+0:13]-[c:14](:[c:15]):[c:16]>>[CH2;D1;+0:3]=[C;H0;D3;+0:9](-[CH;D3;+0:8]1-[C:7]-[O;H0;D2;+0:12]-[C:17]2(-[C:18]-[... | 21.8 | [{"value": 21.8, "product": "C1(=C(C=CC=C1)NC1CCC2(OCC(OO2)C(=C)C2=CC=CC=C2)CC1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To mixture of trioxane 3a (0.50 g, 1.82 mmol) and 2-aminobiphenyl (0.38 g, 2.27 mmol) in dichloromethane (20 ml) acetic acid was added (1 ml) and reaction mixture was stirred at room temp for half an hour. Sodium triacetoxyborohydride (0.58 g, 2.73 mmol) was added slowly and it was stirred for 3 h at room temperature. ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Peroxide.Peroxide | Ether.Secondary amine.Peroxide.Vinyl | C1COOOC1 | c1ccccc1.C1CCC2(CC1)OCCOO2 | c1ccccc1.C1CCC2(CC1)OCCOO2.c1ccccc1.c1ccccc1 | null | ClCCl | null | null | C1COOOC1.CC(=O)O[BH-](OC(C)=O)OC(C)=O.Nc1ccccc1-c1ccccc1>ClCCl>C=C(c1ccccc1)C1COC2(CCC(Nc3ccccc3-c3ccccc3)CC2)OO1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8e433fe3a5b94f9cb05d2594a2d623bf | C1COOOC1.CC(=O)O[BH-](OC(C)=O)OC(C)=O.Nc1ccc(-c2ccccc2)cc1>>C=C(c1ccccc1)C1COC2(CCC(Nc3ccc(-c4ccccc4)cc3)CC2)OO1 | O.O1OOCCC1.NC1=CC=C(C=C1)C1=CC=CC=C1.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>C1(=CC=C(C=C1)NC1CCC2(OCC(OO2)C(=C)C2=CC=CC=C2)CC1)C1=CC=CC=C1 | [CH2:2]1[CH2:9][CH2:10][O:11][O:32][O:31]1.O=[C:1](O[BH-](O[C:8](=O)[CH3:3])O[C:15](=O)[CH3:29])[CH3:13].[NH2:16][c:17]1[cH:18][cH:19][c:20](-[c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[cH:27][cH:28]1>>[CH2:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[CH:9]1[CH2:10][O:11][C:12]2([CH2:13][CH2:14][CH:15]([NH:16][c:17... | C1COOOC1.CC(=O)O[BH-](OC(C)=O)OC(C)=O.Nc1ccc(-c2ccccc2)cc1 | C=C(c1ccccc1)C1COC2(CCC(Nc3ccc(-c4ccccc4)cc3)CC2)OO1 | null | null | ClCCl | Aromatic Heterocycle Formation | OtherReaction | e1ccf6effe82ed570627042fc7a202dfeff5db514191bfb6c0626713ad8ba185 | ab2c134b6353bbc2872cad7da7c653ff912491653702c9701526cbe073308159 | C=C(c1ccccc1)C1COC2(CCC(Nc3ccc(-c4ccccc4)cc3)CC2)OO1 | O=[C;H0;D3;+0:1](-[CH3;D1;+0:2])-O-[BH-](-O-[C;H0;D3;+0:3](=O)-[CH3;D1;+0:4])-O-[C;H0;D3;+0:5](=O)-[CH3;D1;+0:6].[C:7]1-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[O;H0;D2;+0:10]-[O;H0;D2;+0:11]-[O;H0;D2;+0:12]-1.[NH2;D1;+0:13]-[c:14](:[c:15]):[c:16]>>[CH2;D1;+0:3]=[C;H0;D3;+0:9](-[CH;D3;+0:8]1-[C:7]-[O;H0;D2;+0:12]-[C:17]2(-[C:18]-[... | 70.5 | [{"value": 70.5, "product": "C1(=CC=C(C=C1)NC1CCC2(OCC(OO2)C(=C)C2=CC=CC=C2)CC1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of trioxane 3a (0.40 g, 1.45 mmol) and 4-aminobiphenyl (0.30 g, 1.82 mmol) in dichloromethane (20 ml) acetic acid (1 ml) was added and reaction mixture was stirred at room temp for half an hour. Sodium triacetoxyborohydride (0.46 g, 3.63 mmol) was added slowly and it was stirred for 3 h at room temperature... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Peroxide.Peroxide | Ether.Secondary amine.Peroxide.Vinyl | C1COOOC1 | c1ccccc1.C1CCC2(CC1)OCCOO2 | c1ccccc1.C1CCC2(CC1)OCCOO2.c1ccccc1.c1ccccc1 | null | ClCCl | null | null | C1COOOC1.CC(=O)O[BH-](OC(C)=O)OC(C)=O.Nc1ccc(-c2ccccc2)cc1>ClCCl>C=C(c1ccccc1)C1COC2(CCC(Nc3ccc(-c4ccccc4)cc3)CC2)OO1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-48f2f96693514efc95e18b49d57fb3dd | CCCCO.O=C([O-])[O-].OCCOCCCl.c1ccc2c(c1)N=C(N1CCNCC1)c1ccccc1S2>>O=C(O)/C=C/C(=O)O.OCCOCCN1CCN(C2=Nc3ccccc3Sc3ccccc32)CC1 | CCCCO.Cl.N1(CCNCC1)C1=NC2=C(SC3=C1C=CC=C3)C=CC=C2.C(=O)([O-])[O-].[Na+].[Na+].ClCCOCCO.CCCCO>>C=1C=CC2=C(C1)C(=NC=3C=CC=CC3S2)N4CCN(CC4)CCOCCO.C(=C/C(=O)O)\C(=O)O | C[CH2:5][CH2:4][CH2:2][OH:3].[O-:1][C:6](=[O:7])[O-:8].Cl[CH2:14][CH2:13][O:12][CH2:11][CH2:10][OH:9].[NH:15]1[CH2:16][CH2:17][N:18]([C:19]2=[N:20][c:21]3[cH:22][cH:23][cH:24][cH:25][c:26]3[S:27][c:28]3[cH:29][cH:30][cH:31][cH:32][c:33]32)[CH2:34][CH2:35]1>>[O:1]=[C:2]([OH:3])/[CH:4]=[CH:5]/[C:6](=[O:7])[OH:8].[OH:9][C... | CCCCO.O=C([O-])[O-].OCCOCCCl.c1ccc2c(c1)N=C(N1CCNCC1)c1ccccc1S2 | O=C(O)/C=C/C(=O)O.OCCOCCN1CCN(C2=Nc3ccccc3Sc3ccccc32)CC1 | null | CCCC[N+](CCCC)(CCCC)CCCC.[Br-] | O | C-C Coupling | OtherReaction | 966a01ea2948ed1407014be5aefa7081491af4535a35e3de6f886177953b0a8b | fc43d5d9d3dde9473af63a4f418948137903279c5609d3dff4eea459a1927335 | c1ccc2c(c1)N=C(N1CCNCC1)c1ccccc1S2 | C-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[O;D1;H1:4].Cl-[CH2;D2;+0:5]-[C:6]-[#8:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1.[O-;H0;D1:14]-[C;H0;D3;+0:15](-[O-;H0;D1:16])=[O;D1;H0:17]>>[#8:7]-[C:6]-[CH2;D2;+0:5]-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1.[O;D1;H0:17]=[C;H0;D3;+0:15](-[OH;D1;+0:16]... | null | [] | 25 | CELSIUS | null | null | A 100 liter reactor equipped with mechanical stirrer, condenser, and thermometer, was charged with n-BuOH (40.5 L), 11-piperazinyl dibenzo[b,f][1,4]thiazepinehydrochloride (15 kg), Na2CO3 (7.5 kg), TBAB (1.5 kg) and 2-(2-chloroethoxy)ethanol (5.25 L). The mixture was heated to 115° C. during which time a portion of the... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol.Secondary amine | Carboxylic acid.Carboxylic acid.Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.C1=Nc2ccccc2Sc2ccccc21 | HCl | CCCC[N+](CCCC)(CCCC)CCCC.[Br-].O | 25 | null | CCCCO.O=C([O-])[O-].OCCOCCCl.c1ccc2c(c1)N=C(N1CCNCC1)c1ccccc1S2>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].O>O=C(O)/C=C/C(=O)O.OCCOCCN1CCN(C2=Nc3ccccc3Sc3ccccc32)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e3b0a9e08bad46409dd0b43d168b1203 | CC1CCN(c2c(-c3c(F)cccc3Cl)c(Cl)nc3ncnn23)CC1.CO>>COc1nc2ncnn2c(NC(C)C)c1-c1c(F)cccc1Cl | CO.ClC1=NC=2N(C(=C1C1=C(C=CC=C1F)Cl)N1CCC(CC1)C)N=CN2.C[O-].[Na+].CO>>COC1=NC=2N(C(=C1C1=C(C=CC=C1F)Cl)NC(C)C)N=CN2 | Cl[c:3]1[n:4][c:5]2[n:6][cH:7][n:8][n:9]2[c:10]([N:11]2CC[CH:12]([CH3:13])[CH2:14]C2)[c:15]1-[c:16]1[c:17]([F:18])[cH:19][cH:20][cH:21][c:22]1[Cl:23].[CH3:1][OH:2]>>[CH3:1][O:2][c:3]1[n:4][c:5]2[n:6][cH:7][n:8][n:9]2[c:10]([NH:11][CH:12]([CH3:13])[CH3:14])[c:15]1-[c:16]1[c:17]([F:18])[cH:19][cH:20][cH:21][c:22]1[Cl:23] | CC1CCN(c2c(-c3c(F)cccc3Cl)c(Cl)nc3ncnn23)CC1.CO | COc1nc2ncnn2c(NC(C)C)c1-c1c(F)cccc1Cl | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | ffe2b968e00a78f2945d96650c55db0b64427327a267c0e622b9b7822b8fc548 | aa61c717c3decc4b9f621ca66f2e82546c76c601e61592e7a86272dd9f1df4b3 | c1ccc(-c2cnc3ncnn3c2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[#7;a:4]:[c:5]:[#7;a:6]:[#7;a:7]:2:[c:8](-[N;H0;D3;+0:9]2-C-C-[CH;D3;+0:10](-[C;D1;H3:11])-[CH2;D2;+0:12]-C-2):[c:13]:1-[c:14].[C;D1;H3:15]-[OH;D1;+0:16]>>[C;D1;H3:11]-[CH;D3;+0:10](-[CH3;D1;+0:12])-[NH;D2;+0:9]-[c:8]1:[#7;a:7]2:[#7;a:6]:[c:5]:[#7;a:4]:[c:3]:2:[#7;a:2]:[c;H0;D3;+0:1](... | null | [] | null | null | null | null | To a solution of 65 mmol 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(4-methylpiperidin-1-yl)-[1,2,4]-triazolo[1,5-α]pyrimidine [cf. EP-A 550 113] in dry methanol 71.5 mmol of a 30% solution of sodium methanolate were added at 20 to 25° C. After having stirred this mixture for about 16 hours at this temperature methanol ws ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amine.Methanol | Ether.Secondary amine | c1cnc2ncnn2c1.C1CC[NH]CC1 | c1cnc2ncnn2c1 | c1cnc2ncnn2c1.c1ccccc1 | HCl | null | null | null | CC1CCN(c2c(-c3c(F)cccc3Cl)c(Cl)nc3ncnn23)CC1.CO>>COc1nc2ncnn2c(NC(C)C)c1-c1c(F)cccc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b2a9f41eff9c4c85a0dfe07c22329aa1 | COC1=CC=C2[C@H]3Cc4ccc(OC)c5c4[C@@]2(CCN3C)[C@H]1O5.OO>>COc1ccc2c3c1OC1C(=O)C=C[C@@]4(O)[C@@H](C2)N(C)CC[C@]314 | OO.CN1CC[C@]23C4=C5C=CC(=C4O[C@H]2C(=CC=C3[C@H]1C5)OC)OC>>CN1CC[C@]23C4C(=O)C=C[C@]2([C@H]1CC5=C3C(=C(C=C5)OC)O4)O | C[O:12][C:11]1=[CH:13][CH:14]=[C:15]2[C@H:17]3[CH2:18][c:6]4[cH:5][cH:4][c:3]([O:2][CH3:1])[c:8]5[c:7]4[C@:23]2([C@H:10]1[O:9]5)[CH2:22][CH2:21][N:19]3[CH3:20].O[OH:16]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]3[c:8]1[O:9][CH:10]1[C:11](=[O:12])[CH:13]=[CH:14][C@@:15]4([OH:16])[C@@H:17]([CH2:18]2)[N:19]([CH3:20])[CH2:... | COC1=CC=C2[C@H]3Cc4ccc(OC)c5c4[C@@]2(CCN3C)[C@H]1O5.OO | COc1ccc2c3c1OC1C(=O)C=C[C@@]4(O)[C@@H](C2)N(C)CC[C@]314 | null | null | null | Acylation | OtherReaction | efa20ff62ebe876e24e2d2de28ad90cbb0a393b571a4ec8e98dc162b5cbea86b | 121b0afd551ef6c4ab30f4344a7aba9f94f7d29b2ba3ad55fde8838b38bea58c | O=C1C=CC2[C@H]3Cc4cccc5c4[C@@]2(CCN3)C1O5 | C-[O;H0;D2;+0:1]-[C;H0;D3;+0:2]1=[CH;D2;+0:3]-[CH;D2;+0:4]=[C;H0;D3;+0:5]2-[C:6](-[C:7])-[#7:8](-[C;D1;H3:9])-[C:10]-[C:11]-[C:12]-23-[c:13]:[c:14]-[#8:15]-[C@@H;D3;+0:16]-1-3.O-[OH;D1;+0:17]>>[C:7]-[C:6]1-[#7:8](-[C;D1;H3:9])-[C:10]-[C:11]-[C:12]23-[c:13]:[c:14]-[#8:15]-[CH;D3;+0:16]-2-[C;H0;D3;+0:2](=[O;H0;D1;+0:1])-... | null | [] | null | null | 3 | HOUR | A 0.10 L round bottom flask (RBF) is charged with 18.9 g of formic acid, 9.9 g of water, and 7.8 g of 2-propanol. This mixture is stirred at 20–30° C. for 5 minutes. Into this solution is added 5.0 g of thebaine bitartrate monohydrate. This is stirred magnetically at room temperature for 10 minutes until dissolution is... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Peroxide.Conjugated diene | Ketone.Tertiary alcohol | C1=C[C@@H]2Oc3cccc4c3[C@@]23CC[NH][C@H](C4)C3=C1 | C1=C[C@H]2[C@H]3Cc4cccc5c4[C@@]2(CC[NH]3)C(C1)O5 | C1=C[C@H]2[C@H]3Cc4cccc5c4[C@@]2(CC[NH]3)C(C1)O5 | HO- | null | null | 3 | COC1=CC=C2[C@H]3Cc4ccc(OC)c5c4[C@@]2(CCN3C)[C@H]1O5.OO>>COc1ccc2c3c1OC1C(=O)C=C[C@@]4(O)[C@@H](C2)N(C)CC[C@]314 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1fa2ba475a8c427c8914a6f9aa3a427b | COc1ccc2c3c1OC1C(=O)C=C[C@@]4(O)[C@@H](C2)N(C)CC[C@]314>>COc1ccc2c3c1O[C@H]1C(=O)CC[C@@]4(O)[C@@H](C2)N(C)CC[C@]314 | [H][H].[OH-].[Na+].NC(=S)N.[H][H].CN1CC[C@]23C4C(=O)C=C[C@]2([C@H]1CC5=C3C(=C(C=C5)OC)O4)O.P(O)(O)(O)=O.CN1CC[C@]23C4C(=O)C=C[C@]2([C@H]1CC5=C3C(=C(C=C5)OC)O4)O>>CN1CC[C@]23C4=C5C=CC(=C4O[C@H]2C(=O)CC[C@]3([C@H]1C5)O)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]3[c:8]1[O:9][CH:10]1[C:11](=[O:12])[CH:13]=[CH:14][C@@:15]4([OH:16])[C@@H:17]([CH2:18]2)[N:19]([CH3:20])[CH2:21][CH2:22][C@:23]314>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]3[c:8]1[O:9][C@H:10]1[C:11](=[O:12])[CH2:13][CH2:14][C@@:15]4([OH:16])[C@@H:17]([CH2:18]2)[N:19]([CH3:20])... | COc1ccc2c3c1OC1C(=O)C=C[C@@]4(O)[C@@H](C2)N(C)CC[C@]314 | COc1ccc2c3c1O[C@H]1C(=O)CC[C@@]4(O)[C@@H](C2)N(C)CC[C@]314 | null | [Pd] | C1CCOC1 | Reduction | Hydrogenation (double to single) | 752a5e0201ff34934d313f015d6a5a71e40fcc2b623f54907dfade159f526495 | 0e0db21233797ec1d2a9464a1f32cef94e53e6a41f96d680fa1307067bbf01f2 | O=C1CCC2[C@H]3Cc4cccc5c4[C@@]2(CCN3)[C@H]1O5 | [#7:1]-[C:2]-[C:3]1(-[O;D1;H1:4])-[C:5]-[C:6](-[#8:7])-[C:8](=[O;D1;H0:9])-[CH;D2;+0:10]=[CH;D2;+0:11]-1>>[#7:1]-[C:2]-[C:3]1(-[O;D1;H1:4])-[C:5]-[C:6](-[#8:7])-[C:8](=[O;D1;H0:9])-[CH2;D2;+0:10]-[CH2;D2;+0:11]-1 | 91.2 | [{"value": 91.0, "product": "CN1CC[C@]23C4=C5C=CC(=C4O[C@H]2C(=O)CC[C@]3([C@H]1C5)O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.2, "product": "CN1CC[C@]23C4=C5C=CC(=C4O[C@H]2C(=O)CC[C@]3([C@H]1C5)O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A known amount of THF (26.7 g) is charged into a 0.5 L RBF, and 3.05 g of 14-hydroxycodeinone is added into it. With stirring 120 g of aqueous phosphoric acid (1M, 9.8%) is added. The mixture is stirred until the entire solid dissolved. While stirring 40% aqueous sodium hydroxide is added (12.5 g) dropwise over a 30-mi... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ketone | C1=C[C@H]2[C@H]3Cc4cccc5c4[C@@]2(CC[NH]3)C(C1)O5 | c1cc2c3c(c1)O[C@H]1CCC[C@H]4[C@@H](C2)[NH]CC[C@]314 | c1cc2c3c(c1)O[C@H]1CCC[C@H]4[C@@H](C2)[NH]CC[C@]314 | null | [Pd].C1CCOC1 | null | null | COc1ccc2c3c1OC1C(=O)C=C[C@@]4(O)[C@@H](C2)N(C)CC[C@]314>[Pd].C1CCOC1>COc1ccc2c3c1O[C@H]1C(=O)CC[C@@]4(O)[C@@H](C2)N(C)CC[C@]314 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4f04d2a2c56b4b278b7210afb01bb875 | Cl>>Cl | CN1CC[C@]23C4=C5C=CC(=C4O[C@H]2C(=O)CC[C@]3([C@H]1C5)O)OC.Cl.C(C)O>>CN1CC[C@]23C4=C5C=CC(=C4O[C@H]2C(=O)CC[C@]3([C@H]1C5)O)OC.Cl | [ClH:24]>>[ClH:24] | Cl | Cl | null | null | C(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | 2 | HOUR | A known amount of oxycodone (2.80 g) is charged into a 100 mL round-bottom flask equipped with a magnetic stirrer, a reflux condenser, and a thermometer. Into this, 11 g of anhydrous ethanol is added. This is heated to reflux to form a white suspension. Into this hot suspension, 2.75 g of hydrochloride-ethanol solution... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)O | null | 2 | Cl>C(C)O>Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-190cfc1c9d394de69600f360139a158f | COc1ccc2c3c1OC1C(=O)C=C[C@@]4(O)[C@@H](C2)N(C)CC[C@]314>>COc1ccc2c3c1O[C@H]1C(=O)CC[C@@]4(O)[C@@H](C2)N(C)CC[C@]314 | CN1CC[C@]23C4C(=O)C=C[C@]2([C@H]1CC5=C3C(=C(C=C5)OC)O4)O>>CN1CC[C@]23C4=C5C=CC(=C4O[C@H]2C(=O)CC[C@]3([C@H]1C5)O)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]3[c:8]1[O:9][CH:10]1[C:11](=[O:12])[CH:13]=[CH:14][C@@:15]4([OH:16])[C@@H:17]([CH2:18]2)[N:19]([CH3:20])[CH2:21][CH2:22][C@:23]314>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]3[c:8]1[O:9][C@H:10]1[C:11](=[O:12])[CH2:13][CH2:14][C@@:15]4([OH:16])[C@@H:17]([CH2:18]2)[N:19]([CH3:20])... | COc1ccc2c3c1OC1C(=O)C=C[C@@]4(O)[C@@H](C2)N(C)CC[C@]314 | COc1ccc2c3c1O[C@H]1C(=O)CC[C@@]4(O)[C@@H](C2)N(C)CC[C@]314 | null | [Pd] | null | Reduction | Hydrogenation (double to single) | 752a5e0201ff34934d313f015d6a5a71e40fcc2b623f54907dfade159f526495 | 0e0db21233797ec1d2a9464a1f32cef94e53e6a41f96d680fa1307067bbf01f2 | O=C1CCC2[C@H]3Cc4cccc5c4[C@@]2(CCN3)[C@H]1O5 | [#7:1]-[C:2]-[C:3]1(-[O;D1;H1:4])-[C:5]-[C:6](-[#8:7])-[C:8](=[O;D1;H0:9])-[CH;D2;+0:10]=[CH;D2;+0:11]-1>>[#7:1]-[C:2]-[C:3]1(-[O;D1;H1:4])-[C:5]-[C:6](-[#8:7])-[C:8](=[O;D1;H0:9])-[CH2;D2;+0:10]-[CH2;D2;+0:11]-1 | 85 | [{"value": 85.0, "product": "CN1CC[C@]23C4=C5C=CC(=C4O[C@H]2C(=O)CC[C@]3([C@H]1C5)O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 21.5 | HOUR | To the solution of 14-hydroxycodeinone produced in Example 14 is added 0.5 g of 5% palladium on carbon, 50% wet. The mixture is hydrogenated at 30 to 40 psi for a period of 18 to 25 hours at ambient temperature. The catalyst is filtered off and is washed with 5 ml of water. The filtrate is cooled to 0–5° C. and with st... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ketone | C1=C[C@H]2[C@H]3Cc4cccc5c4[C@@]2(CC[NH]3)C(C1)O5 | c1cc2c3c(c1)O[C@H]1CCC[C@H]4[C@@H](C2)[NH]CC[C@]314 | c1cc2c3c(c1)O[C@H]1CCC[C@H]4[C@@H](C2)[NH]CC[C@]314 | null | [Pd] | null | 21.5 | COc1ccc2c3c1OC1C(=O)C=C[C@@]4(O)[C@@H](C2)N(C)CC[C@]314>[Pd]>COc1ccc2c3c1O[C@H]1C(=O)CC[C@@]4(O)[C@@H](C2)N(C)CC[C@]314 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5b665a2b43e14375b34a87ca38617832 | Cl>>Cl | Cl.CN1CC[C@]23C4=C5C=CC(=C4O[C@H]2C(=O)CC[C@]3([C@H]1C5)O)OC.C(C)O>>CN1CC[C@]23C4=C5C=CC(=C4O[C@H]2C(=O)CC[C@]3([C@H]1C5)O)OC.Cl | [ClH:24]>>[ClH:24] | Cl | Cl | null | null | C(C)(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 85 | [{"value": 85.0, "product": "CN1CC[C@]23C4=C5C=CC(=C4O[C@H]2C(=O)CC[C@]3([C@H]1C5)O)OC.Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 8.1 g of oxycodone obtained in Example 15 and 80 ml of ethanol are placed in a 250 ml round-bottomed flask. The mixture is heated to reflux. Into the hot mixture is added 10 ml of a concentrated solution of hydrogen chloride in isopropanol. The mixture is cooled and stirred at 0–5° C. for 1–2 hours. The product is filt... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)(C)O | null | null | Cl>C(C)(C)O>Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-23c53c47db3d41769913a28db1a35118 | N#Cc1ccc(-c2ccco2)cc1.NC(=NO)c1ccc(Br)cc1>>N#Cc1ccc(-c2ccc(-c3ccc(C#N)cc3)o2)cc1 | BrC1=CC=C(C(N)=NO)C=C1.BrC1=CC=C(C(N)=NO)C=C1.C(#N)C1=CC=C(C=C1)C=1OC=CC1>>C(#N)C1=CC=C(C=C1)C=1OC(=CC1)C1=CC=C(C=C1)C#N | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][o:19]2)[cH:20][cH:21]1.ON=[C:15]([c:14]1[cH:13][cH:12][c:11](Br)[cH:18][cH:17]1)[NH2:16]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][c:14]([C:15]#[N:16])[cH:17][cH:18]3)[o:19]2)[cH:20][cH:21]1 | N#Cc1ccc(-c2ccco2)cc1.NC(=NO)c1ccc(Br)cc1 | N#Cc1ccc(-c2ccc(-c3ccc(C#N)cc3)o2)cc1 | null | null | C(C1=CC=CC=C1)#N | C-C Coupling | OtherReaction | 1fa403af87c74b70ddf126f5f3d1d35552536a371b7dca5b886385e7398fd93e | 5a322521d2e37b68d2c1cdb2695844665e84a24d702c9cebff9cc44ba3f0b615 | c1ccc(-c2ccc(-c3ccccc3)o2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](-[C;H0;D3;+0:5](-[NH2;D1;+0:6])=N-O):[c:7]:[c:8]:1.[#8;a:9]1:[c:10]:[c:11]:[c:12]:[cH;D2;+0:13]:1>>[N;H0;D1;+0:6]#[C;H0;D2;+0:5]-[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:13]2:[#8;a:9]:[c:10]:[c:11]:[c:12]:2):[c:8]:[c:7]:1 | null | [] | null | null | null | null | in good yield. In contrast, under N-coupling conditions the benzamidoxime was converted to benzonitrile (Anbazhagan et al., (2002) Tetrahedron Lett. 43: 4221) and attempted Heck coupling of 4-bromobenzamidoxime with 2(4-cyanophenyl)furan yielded 2,5-bis(4-cyanophenyl)furan.
Conditions: See reaction.notes.procedure_deta... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine.Oxime | Nitrile | c1ccoc1.c1ccccc1 | c1ccoc1.c1ccccc1 | c1ccccc1.c1ccoc1.c1ccccc1 | HBr | C(C1=CC=CC=C1)#N | null | null | N#Cc1ccc(-c2ccco2)cc1.NC(=NO)c1ccc(Br)cc1>C(C1=CC=CC=C1)#N>N#Cc1ccc(-c2ccc(-c3ccc(C#N)cc3)o2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-74abcbab50d444e0b4279f6817692f42 | CC[C@H](C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCCl.[I-]>>CC[C@H](C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCI | ClCOC([C@@H](NC(=O)OC(C)(C)C)[C@@H](C)CC)=O.[I-].[Na+]>>ICOC([C@@H](NC(=O)OC(C)(C)C)[C@@H](C)CC)=O | Cl[CH2:17][O:16][C:14]([C@H:5]([C@H:3]([CH2:2][CH3:1])[CH3:4])[NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:15].[I-:18]>>[CH3:1][CH2:2][C@H:3]([CH3:4])[C@H:5]([NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[C:14](=[O:15])[O:16][CH2:17][I:18] | CC[C@H](C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCCl.[I-] | CC[C@H](C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCI | null | null | C(C)#N | Functional Group Interconversion | OtherReaction | 10bee13c50a4ba107934328c21250869f883899fc8944cf8a0ebee609aa1691d | fe69d77c5ffecf9aa0236c58528d10fdb0294a434868899e60e585d0629b72f9 | null | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3](-[C:4])=[O;D1;H0:5].[I-;H0;D0:6]>>[C:4]-[C:3](=[O;D1;H0:5])-[#8:2]-[CH2;D2;+0:1]-[I;H0;D1;+0:6] | 87 | [{"value": 87.0, "product": "ICOC([C@@H](NC(=O)OC(C)(C)C)[C@@H](C)CC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 4 | HOUR | To a solution of N-BOC-L-isoleucine chloromethyl ester (19.6 g, 70 mmol) in acetonitrile (300 mL), was added sodium iodide (31.5 g, 210 mmol). The solution was stirred for 4 h at 60° C. The resulting suspension was filtered and the filtrate was evaporated. The residue was dissolved in CH2Cl2 and washed with aqueous sod... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Primary halide | null | null | null | Other | C(C)#N | 60 | 4 | CC[C@H](C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCCl.[I-]>C(C)#N>CC[C@H](C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCI |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7438d544248847338e40decfde61667a | CC(C)(CO)C(=O)O.CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)O>>CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCC(C)(C)C(=O)O | C(=O)(OC(C)(C)C)N[C@@H](C(C)C)C(=O)O.C1CCC(CC1)N=C=NC2CCCCC2.CC(C(=O)O)(CO)C.N1=CC=CC=C1>>CC(C(=O)O)(COC([C@@H](NC(=O)OC(C)(C)C)C(C)C)=O)C | [OH:15][CH2:16][C:17]([CH3:18])([CH3:19])[C:20](=[O:21])[OH:22].O[C:13]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])=[O:14]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[C:13](=[O:14])[O:15][CH2:16][C:17]([CH3:18])([CH3:19])[C:20](... | CC(C)(CO)C(=O)O.CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)O | CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCC(C)(C)C(=O)O | null | CN(C1=CC=NC=C1)C | C(Cl)Cl | Acylation | Esterification of Carboxylic Acids | d9bd78214ee7dbc907e499722ae01849a72d188753963443e5df9fe42c31c43b | 3652e761944e8ef7ee40675a156c8ae39909c72166786934d88652debf2ec1ac | null | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12].[O;D1;H0:13]=[C:14](-[O;D1;H1:15])-[C:16]-[C:17]-[OH;D1;+0:18]>>[C:4]-[C:3](-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O... | null | [] | null | null | 2 | HOUR | N-Boc-L-valine (10.8 g, 50 mmole), 4-dimethylaminopyridine (610 mg, 5 mmole) and DCC (6.18 g, 30 mmole) were dissolved in methylene chloride (100 ml). After stirring for 2 hour the mixture was filtered. To the filtrate were added 2,2-dimethyl-3-hydroxy-propionic acid (3.54 g, 30 mmole) and pyridine (10 ml). After 18 hr... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | null | HO- | CN(C1=CC=NC=C1)C.C(Cl)Cl | null | 2 | CC(C)(CO)C(=O)O.CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)O>CN(C1=CC=NC=C1)C.C(Cl)Cl>CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCC(C)(C)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ed0635e891984285a69798f36ec59943 | CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCC(C)(C)C(=O)O.ClCI>>CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCC(C)(C)C(=O)OCCl | CC(C(=O)O)(COC([C@@H](NC(=O)OC(C)(C)C)C(C)C)=O)C.[OH-].C(CCC)[N+](CCCC)(CCCC)CCCC.ClCI>>ClCOC(C(COC([C@@H](NC(=O)OC(C)(C)C)C(C)C)=O)(C)C)=O | [CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[C:13](=[O:14])[O:15][CH2:16][C:17]([CH3:18])([CH3:19])[C:20](=[O:21])[OH:22].I[CH2:23][Cl:24]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[C:13](=[O:14])[O:15][CH2:16][C:17]([CH3:18])([C... | CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCC(C)(C)C(=O)O.ClCI | CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCC(C)(C)C(=O)OCCl | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2f16a3cac6d3c4085515a42267501b7a0eef68b042dbe72a334a9b3dd1458b44 | 20b23d23df2ca888376bbfdf646588e67491b315935b071cb9ba310488e4ee8f | null | I-[CH2;D2;+0:1]-[Cl;D1;H0:2].[C:3]-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6]>>[C:3]-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[Cl;D1;H0:2] | null | [] | null | null | 18 | HOUR | 2,2-dimethyl-3-(N-Boc-L-valyloxy)propionic acid (3.9 g, 12.3 mmole) was dissolved in dioxane (60 ml). To the solution was added tetrabutylammonium hydroxide aqueous solution (40%, 7.78 ml, 12 mmole). The solution was dried in vacuo, and it was coevaporated with toluene for several times. The residue was dissolved in me... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Carboxylic acid | Primary halide.Ester | null | null | null | HI | O1CCOCC1 | null | 18 | CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCC(C)(C)C(=O)O.ClCI>O1CCOCC1>CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCC(C)(C)C(=O)OCCl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-097a601cbd594cd3941a4a68eb987caa | CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCC(C)(C)C(=O)OCCl.[I-]>>CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCC(C)(C)C(=O)OCI | ClCOC(C(COC([C@@H](NC(=O)OC(C)(C)C)C(C)C)=O)(C)C)=O.[I-].[Na+]>>ICOC(C(COC([C@@H](NC(=O)OC(C)(C)C)C(C)C)=O)(C)C)=O | Cl[CH2:23][O:22][C:20]([C:17]([CH2:16][O:15][C:13]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])=[O:14])([CH3:18])[CH3:19])=[O:21].[I-:24]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[C:13](=[O:14])[O:15][CH2:16][C:17]([CH3:18])([C... | CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCC(C)(C)C(=O)OCCl.[I-] | CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCC(C)(C)C(=O)OCI | null | null | C(C)#N | Functional Group Interconversion | OtherReaction | 10bee13c50a4ba107934328c21250869f883899fc8944cf8a0ebee609aa1691d | fe69d77c5ffecf9aa0236c58528d10fdb0294a434868899e60e585d0629b72f9 | null | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3](-[C:4])=[O;D1;H0:5].[I-;H0;D0:6]>>[C:4]-[C:3](=[O;D1;H0:5])-[#8:2]-[CH2;D2;+0:1]-[I;H0;D1;+0:6] | 94.9 | [{"value": 94.9, "product": "ICOC(C(COC([C@@H](NC(=O)OC(C)(C)C)C(C)C)=O)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2,2-Dimethyl-3-(N-Boc-L-valyloxy)propionic acid chloromethyl ester (3.6 g, 10 mmole) was dissolved in acetonitrile (50 ml). Sodium iodide (2.1 g, 14 mmole) was added to the solution. After reaction at 70° C. for 2 hr, the reaction mixture was filtered and the residue was dissolved in methylene chloride (20 ml) and refi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Primary halide | null | null | null | Other | C(C)#N | null | null | CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCC(C)(C)C(=O)OCCl.[I-]>C(C)#N>CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCC(C)(C)C(=O)OCI |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-73befd23f9934808883731425e70cde4 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(=O)O.ClCI>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(=O)OCCl | C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCC(CC(=O)O)COC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O.[OH-].C(CCC)[N+](CCCC)(CCCC)CCCC.ClCI>>ClCOC(CC(COC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)COC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)=O | [CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[O:18][CH2:19][CH:20]([CH2:21][O:22][C:23](=[O:24])[C@@H:25]([NH:26][C:27](=[O:28])[O:29][CH2:30][c:31]1[cH:32][cH:33][cH:34][cH:35][cH:36]1)[CH:37]([CH3:38])[CH3:39])[CH2:40][C:41](=[O:42])[OH:43].I[... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(=O)O.ClCI | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(=O)OCCl | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2f16a3cac6d3c4085515a42267501b7a0eef68b042dbe72a334a9b3dd1458b44 | 20b23d23df2ca888376bbfdf646588e67491b315935b071cb9ba310488e4ee8f | O=C(CNC(=O)OCc1ccccc1)OCCCOC(=O)CNC(=O)OCc1ccccc1 | I-[CH2;D2;+0:1]-[Cl;D1;H0:2].[C:3]-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6]>>[C:3]-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[Cl;D1;H0:2] | null | [] | null | null | null | null | 3,3-bis (N-CBz-L-valyloxymethyl)-propionic acid (3 g, 5 mmole) was dissolved in dioxane (20 ml). To the solution was added tetrabutylammonium hydroxide aqueous solution (40%, 3.11 ml, 4.8 mmole). The solution was dried in vacuo, and it was coevaporated with toluene several times. The residue was dissolved in methylene ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Carboxylic acid | Primary halide.Ester | null | null | c1ccccc1.c1ccccc1 | HI | O1CCOCC1 | null | null | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(=O)O.ClCI>O1CCOCC1>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(=O)OCCl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-40bb33a7a90c41e19c53a6da20d2af1b | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(=O)OCCl.[I-]>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(=O)OCI | ClCOC(CC(COC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)COC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)=O.[I-].[Na+]>>ICOC(CC(COC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)COC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)=O | Cl[CH2:44][O:43][C:41]([CH2:40][CH:20]([CH2:19][O:18][C:16]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)=[O:17])[CH2:21][O:22][C:23](=[O:24])[C@@H:25]([NH:26][C:27](=[O:28])[O:29][CH2:30][c:31]1[cH:32][cH:33][cH:34][cH:35][cH:36]1)[CH:37]([CH3:38])[CH3:39])=... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(=O)OCCl.[I-] | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(=O)OCI | null | null | C(C)#N | Functional Group Interconversion | OtherReaction | 10bee13c50a4ba107934328c21250869f883899fc8944cf8a0ebee609aa1691d | fe69d77c5ffecf9aa0236c58528d10fdb0294a434868899e60e585d0629b72f9 | O=C(CNC(=O)OCc1ccccc1)OCCCOC(=O)CNC(=O)OCc1ccccc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3](-[C:4])=[O;D1;H0:5].[I-;H0;D0:6]>>[C:4]-[C:3](=[O;D1;H0:5])-[#8:2]-[CH2;D2;+0:1]-[I;H0;D1;+0:6] | null | [] | null | null | null | null | 3,3-bis (N-CBz-L-valyloxymethyl)-propionic acid chloromethyl ester (900 mg, 1.38 mmole) was dissolved in acetonitrile (5 ml). Sodium iodide (289 mg, 1.93 mmole) was added to the solution. After reaction at 70° C. for 3 hr, the reaction mixture was filtered and the residue was dissolved in methylene chloride (5 ml) and ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Primary halide | null | null | c1ccccc1.c1ccccc1 | Other | C(C)#N | null | null | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(=O)OCCl.[I-]>C(C)#N>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(COC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)CC(=O)OCI |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-00c0d255c13b4f788d44e347479860d8 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCOC(=O)OCCl.[I-]>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCOC(=O)OCI | C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCCOC(=O)OCCl.[I-].[Na+]>>C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OCCOC(=O)OCI | Cl[CH2:25][O:24][C:22]([O:21][CH2:20][CH2:19][O:18][C:16]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)=[O:17])=[O:23].[I-:26]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[O:18][CH2:... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCOC(=O)OCCl.[I-] | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCOC(=O)OCI | null | null | C(C)#N | Functional Group Interconversion | OtherReaction | 22e4ae0c85daffd0078fd40b928ca1a4ed497239b66c1b767f5c2602965f1e0a | e5953f4c2f3e929ebd5c80667db5cd8a1df5fb6bd8f8f4de947f99af74ff7227 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3](-[#8:4])=[O;D1;H0:5].[I-;H0;D0:6]>>[#8:4]-[C:3](=[O;D1;H0:5])-[#8:2]-[CH2;D2;+0:1]-[I;H0;D1;+0:6] | null | [] | null | null | null | null | 2-(N-CBz-L-valyloxy)ethoxycarbonyloxymethyl chloride (1.16 g, 3 mmole) was dissolved in acetonitrile (10 ml). Sodium iodide (630 g, 4.2 mmole) was added to the solution. After reaction at 65° C. for 2.5 hr, the reaction mixture was cooled down to room temperature and filtered and the residue was dissolved in methylene ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbonic Ester | Primary halide | null | null | c1ccccc1 | Other | C(C)#N | null | null | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCOC(=O)OCCl.[I-]>C(C)#N>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCCOC(=O)OCI |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5055b63534954acc80348260aa3b9b65 | CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)O.CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCC(O)CO>>CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCC(O)COC(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)C | C(C)(C)(C)OC(=O)N[C@@H](C(C)C)C(=O)OCC(O)CO.C(=O)(OC(C)(C)C)N[C@@H](C(C)C)C(=O)O.C1CCC(CC1)N=C=NC2CCCCC2>>C(C)(C)(C)OC(=O)N[C@@H](C(C)C)C(=O)OCC(O)COC([C@@H](NC(=O)OC(C)(C)C)C(C)C)=O | O[C:21](=[O:22])[C@@H:23]([NH:24][C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[CH:32]([CH3:33])[CH3:34].[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[C:13](=[O:14])[O:15][CH2:16][CH:17]([OH:18])[CH2:19][OH:20]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][... | CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)O.CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCC(O)CO | CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCC(O)COC(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)C | null | CN(C)C=1C=CN=CC1 | CN(C)C=O.C(Cl)Cl | Acylation | Esterification of Carboxylic Acids | d9bd78214ee7dbc907e499722ae01849a72d188753963443e5df9fe42c31c43b | 3652e761944e8ef7ee40675a156c8ae39909c72166786934d88652debf2ec1ac | null | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12].[C:13]-[C:14]-[OH;D1;+0:15]>>[C:13]-[C:14]-[O;H0;D2;+0:15]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12] | 49 | [{"value": 49.0, "product": "C(C)(C)(C)OC(=O)N[C@@H](C(C)C)C(=O)OCC(O)COC([C@@H](NC(=O)OC(C)(C)C)C(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.0, "product": "C(C)(C)(C)OC(=O)N[C@@H](C(C)C)C(=O)OCC(O)COC([C@@H](NC(=O)OC(C)(C)C)C(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | null | null | null | null | 1-O-(N-tert-butoxycarbonyl-L-valyl)glycerol (17.95 g. 61.6 mmol), Boc-L-valine (6.69 g, 30.8 mmol), DMAP (0.38 g, 3.1 mmol), and DCC (7.10 g, 34.4 mmol) in 240 mL CH2Cl2 and 60 mL DMF were stirred at rt under N2 for 18 h. The reaction mixture was filtered, concentrated under vacuum, and redissolved in 200 mL EtOAc. The... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | null | HO- | CN(C)C=1C=CN=CC1.CN(C)C=O.C(Cl)Cl | null | null | CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)O.CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCC(O)CO>CN(C)C=1C=CN=CC1.CN(C)C=O.C(Cl)Cl>CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCC(O)COC(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d739aa045e2e4984bbcf85756bd2cf59 | CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCC(O)COC(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)C.O=C(Cl)OCCl>>CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCC(COC(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)C)OC(=O)OCCl | ClC(=O)OCCl.C(C)(C)(C)OC(=O)N[C@@H](C(C)C)C(=O)OCC(O)COC([C@@H](NC(=O)OC(C)(C)C)C(C)C)=O.N1=CC=CC=C1>>ClCOC(=O)OC(COC([C@@H](NC(=O)OC(C)(C)C)C(C)C)=O)COC([C@@H](NC(=O)OC(C)(C)C)C(C)C)=O | [CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[C:13](=[O:14])[O:15][CH2:16][CH:17]([CH2:18][O:19][C:20](=[O:21])[C@@H:22]([NH:23][C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])[CH:31]([CH3:32])[CH3:33])[OH:34].Cl[C:35](=[O:36])[O:37][CH2:38][Cl:39]>>[CH3:1][CH:2]([CH3:... | CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCC(O)COC(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)C.O=C(Cl)OCCl | CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCC(COC(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)C)OC(=O)OCCl | null | null | C(Cl)Cl | Acylation | Schotten-Baumann to ester | 16a18aa130cea39a3a662ee8b6057b54f71a5546be78b0c40ff9ad2c1213d664 | 75f277925c316017cfa5d00758bde92cc568ffecb2651aae6fab24b6daa74c11 | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C:5]-[C:6](-[C:7])-[OH;D1;+0:8]>>[C:5]-[C:6](-[C:7])-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4] | 93.1 | [{"value": 93.0, "product": "ClCOC(=O)OC(COC([C@@H](NC(=O)OC(C)(C)C)C(C)C)=O)COC([C@@H](NC(=O)OC(C)(C)C)C(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.1, "product": "ClCOC(=O)OC(COC([C@@H](NC(=O)OC(C)(C)C)C(C)C)=O)COC([C@@H](NC(=O)OC(C)(C)C)C(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_d... | null | null | 45 | MINUTE | Chloromethyl chloroformate (2.70 mL, 30 mmol) was added to a solution of 1,3-di-O-(N-tert-butoxycarbonyl-L-valyl)glycerol (7.27 g, 14.8 mmol) and pyridine (7.2 mL, 89 mmol) in 60 mL dry CH2Cl2, in an ice bath, under N2. After stirring for 1 h 45 min, the reaction mixture was diluted with 100 mL CH2Cl2 and washed with 4... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary alcohol | Carbonic Ester | null | null | null | HCl | C(Cl)Cl | null | 0.75 | CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCC(O)COC(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)C.O=C(Cl)OCCl>C(Cl)Cl>CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCC(COC(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)C)OC(=O)OCCl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1b60864acca840c38135439a12de4209 | CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCC(COC(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)C)OC(=O)OCCl.[I-]>>CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCC(COC(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)C)OC(=O)OCI | ClCOC(=O)OC(COC([C@@H](NC(=O)OC(C)(C)C)C(C)C)=O)COC([C@@H](NC(=O)OC(C)(C)C)C(C)C)=O.[Na+].[I-]>>ICOC(=O)OC(COC([C@@H](NC(=O)OC(C)(C)C)C(C)C)=O)COC([C@@H](NC(=O)OC(C)(C)C)C(C)C)=O | Cl[CH2:38][O:37][C:35]([O:34][CH:17]([CH2:16][O:15][C:13]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])=[O:14])[CH2:18][O:19][C:20](=[O:21])[C@@H:22]([NH:23][C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])[CH:31]([CH3:32])[CH3:33])=[O:36].[I-:39]>>[CH3:1][CH:2]([CH3:3... | CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCC(COC(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)C)OC(=O)OCCl.[I-] | CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCC(COC(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)C)OC(=O)OCI | null | null | null | Functional Group Interconversion | OtherReaction | 22e4ae0c85daffd0078fd40b928ca1a4ed497239b66c1b767f5c2602965f1e0a | e5953f4c2f3e929ebd5c80667db5cd8a1df5fb6bd8f8f4de947f99af74ff7227 | null | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3](-[#8:4])=[O;D1;H0:5].[I-;H0;D0:6]>>[#8:4]-[C:3](=[O;D1;H0:5])-[#8:2]-[CH2;D2;+0:1]-[I;H0;D1;+0:6] | 92 | [{"value": 92.0, "product": "ICOC(=O)OC(COC([C@@H](NC(=O)OC(C)(C)C)C(C)C)=O)COC([C@@H](NC(=O)OC(C)(C)C)C(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.0, "product": "ICOC(=O)OC(COC([C@@H](NC(=O)OC(C)(C)C)C(C)C)=O)COC([C@@H](NC(=O)OC(C)(C)C)C(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_des... | 80 | CELSIUS | null | null | A solution of 2-O-chloromethoxycarbonyl-1,3-di-O-(N-tert-butoxycarbonyl-L-valyl)propane-1,2,3-triol (7.86 g, 13.5 mmol) and NaI (8.09 g, 54.0 mmol) in 135 mL dry acetonitirile was refluxed at 80° C. for 4 h under N2. The reaction mixture was concentrated under vacuum, and then partitioned between 150 mL diethyl ether a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbonic Ester | Primary halide | null | null | null | Other | null | 80 | null | CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCC(COC(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)C)OC(=O)OCCl.[I-]>>CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCC(COC(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)C)OC(=O)OCI |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0560d91a7a5847519b31a7e0a7966b24 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(OC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(=O)OC(C)(C)C>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(OC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(=O)O | C(C)(C)(C)OC(C(COC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)OC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)=O.FC(C(=O)O)(F)F>>C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OC(C(=O)O)COC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O | CC(C)(C)[O:41][C:39]([CH:20]([CH2:19][O:18][C:16]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)=[O:17])[O:21][C:22](=[O:23])[C@@H:24]([NH:25][C:26](=[O:27])[O:28][CH2:29][c:30]1[cH:31][cH:32][cH:33][cH:34][cH:35]1)[CH:36]([CH3:37])[CH3:38])=[O:40]>>[CH3:1][CH... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(OC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(=O)OC(C)(C)C | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(OC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(=O)O | null | null | ClCCl | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | O=C(CNC(=O)OCc1ccccc1)OCCOC(=O)CNC(=O)OCc1ccccc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | 5 | HOUR | To a solution of t-butyl -2,3-bis-(N-CBz-L-valyloxy)-propionate (7.2 g, 11.4 mmole) in dichloromethane (25 ml) was added trifluoroacetic acid (25 ml) and the solution was stirred for five hours at room temperature. The solution was evaporated under reduced pressure and coevaporated two times with toluene. The product w... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | ClCCl | null | 5 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(OC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(=O)OC(C)(C)C>ClCCl>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)OCC(OC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4078ad561ddb47a59a34b89ace3ee1ca | COc1ccc(CCl)cc1.C[C@H](O)C(=O)O>>COc1ccc(COC(=O)[C@H](C)O)cc1 | COC1=CC=C(CCl)C=C1.O[C@H](C(=O)O)C.CC(C)([O-])C.[K+]>>O[C@H](C(=O)OCC1=CC=C(C=C1)OC)C | Cl[CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:15][cH:14]1.[OH:8][C:9](=[O:10])[C@H:11]([CH3:12])[OH:13]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][C:9](=[O:10])[C@H:11]([CH3:12])[OH:13])[cH:14][cH:15]1 | COc1ccc(CCl)cc1.C[C@H](O)C(=O)O | COc1ccc(COC(=O)[C@H](C)O)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 06c4f868ad4646eea8208ecb83f54ca035dd62d04f0d8101641a4f487f2c695c | 8446834f0edd1e71a2dcaffc09b80c7367abf3407263a8998354a2d20c1766bb | c1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8]>>[C:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 25 | CELSIUS | 1 | HOUR | To a stirred solution of (S)(+)2 hydroxypropionic acid (9.0 g, 100 mmole) in 100 ml dry DMF was added potassium tert-butoxide (12.34 g, 110 mmole) and the mixture was stirred for one hour at 25° C. 4-Methoxybenzyl chloride (18.8 g 120 mmole) was added and the mixture was stirred for six hours at 60° C. The mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ester | null | null | c1ccccc1 | HCl | CN(C)C=O | 25 | 1 | COc1ccc(CCl)cc1.C[C@H](O)C(=O)O>CN(C)C=O>COc1ccc(COC(=O)[C@H](C)O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-305a509630c049e1b60a23777bf2b192 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.COc1ccc(COC(=O)[C@H](C)O)cc1>>COc1ccc(COC(=O)[C@H](C)OC(=O)[C@@H](NC(=O)OCc2ccccc2)C(C)C)cc1 | O[C@H](C(=O)OCC1=CC=C(C=C1)OC)C.C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)O.C1CCC(CC1)N=C=NC2CCCCC2>>C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)O[C@H](C(=O)OCC1=CC=C(C=C1)OC)C | O[C:14](=[O:15])[C@@H:16]([NH:17][C:18](=[O:19])[O:20][CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)[CH:28]([CH3:29])[CH3:30].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][C:9](=[O:10])[C@H:11]([CH3:12])[OH:13])[cH:31][cH:32]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][C:9](=[O:10])[C@H:11]([CH3:12])[O:... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.COc1ccc(COC(=O)[C@H](C)O)cc1 | COc1ccc(COC(=O)[C@H](C)OC(=O)[C@@H](NC(=O)OCc2ccccc2)C(C)C)cc1 | null | CN(C)C=1C=CN=CC1 | ClCCl | Acylation | Esterification of Carboxylic Acids | e916c5b009194e30c618975b40d7a233bfcf81339e65494c4e365f67cc5e011d | 12ba7405a548c6b1674f05065819c74f53f1b6165cd54e84e1f2f208042fe660 | O=C(CNC(=O)OCc1ccccc1)OCC(=O)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7].[C:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[C:12](-[C;D1;H3:13])-[OH;D1;+0:14]>>[C:4]-[C:3](-[#7:5]-[C:6]=[O;D1;H0:7])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:14]-[C:12](-[C;D1;H3:13])-[C:10](=[O;D1;H0:11])-[#8:9]-[C:8] | null | [] | null | null | 8 | HOUR | To a solution of 4-methoxybenzyl (S)-(+)-2-hydroxypropionate (7.6 g, 36 mmole), N-CBZ-L-valine (10.05 g, 40 mmole) and DMAP (0.98 g, 8 mmole) in 150 ml dichloromethane was added a solution of DCC (8.3 g, 40 mmole) and the mixture was stirred overnight at room temperature. The mixture was cooled to about 5° C. and the u... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary alcohol | Ester | null | null | c1ccccc1.c1ccccc1 | HO- | CN(C)C=1C=CN=CC1.ClCCl | null | 8 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.COc1ccc(COC(=O)[C@H](C)O)cc1>CN(C)C=1C=CN=CC1.ClCCl>COc1ccc(COC(=O)[C@H](C)OC(=O)[C@@H](NC(=O)OCc2ccccc2)C(C)C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7840512745e0442c8c468c30f3c605b0 | COc1ccc(COC(=O)[C@H](C)OC(=O)[C@@H](NC(=O)OCc2ccccc2)C(C)C)cc1>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O[C@@H](C)C(=O)O | C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)O[C@H](C(=O)OCC1=CC=C(C=C1)OC)C.FC(C(=O)O)(F)F>>C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)O[C@H](C(=O)O)C | COc1ccc(C[O:23][C:21]([C@@H:19]([O:18][C:16]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)=[O:17])[CH3:20])=[O:22])cc1>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[O:18][C@@H:19]([CH... | COc1ccc(COC(=O)[C@H](C)OC(=O)[C@@H](NC(=O)OCc2ccccc2)C(C)C)cc1 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O[C@@H](C)C(=O)O | null | null | ClCCl | Reduction | Ester saponification (alkyl deprotection) | af4a00273af84ecb3074b1842201a78a3aac9a41d2050132ad8c8c1c9d796dee | 8d997f8b7994d8c9cf23425771b3f80d4d4830ac4e3d6552f381db244a5a65c5 | c1ccccc1 | C-O-c1:c:c:c(-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]):c:c:1>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | 5 | HOUR | To a solution of 4-methoxybenzyl (S)-(+)-2-(N-CBz-L-valyloxy)propionate (14.0 g, 31.5 mmole) in dichloromethane (50 ml) was added trifluoroacetic acid (25 ml) and the solution was stirred for five hours at room temperature. The solution was evaporated under reduced pressure and coevaporated two times with toluene. The ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether | Carboxylic acid | c1ccccc1 | null | c1ccccc1 | HO- | ClCCl | null | 5 | COc1ccc(COC(=O)[C@H](C)OC(=O)[C@@H](NC(=O)OCc2ccccc2)C(C)C)cc1>ClCCl>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O[C@@H](C)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-456261c7dad64f4b82b109c7e26a8345 | CC(O)C(=O)O.COc1ccc(CCl)cc1>>COc1ccc(COC(=O)C(C)O)cc1 | COC1=CC=C(CCl)C=C1.OC(C(=O)O)C.CC(C)([O-])C.[K+]>>OC(C(=O)OCC1=CC=C(C=C1)OC)C | [OH:8][C:9](=[O:10])[CH:11]([CH3:12])[OH:13].Cl[CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:15][cH:14]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][C:9](=[O:10])[CH:11]([CH3:12])[OH:13])[cH:14][cH:15]1 | CC(O)C(=O)O.COc1ccc(CCl)cc1 | COc1ccc(COC(=O)C(C)O)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 06c4f868ad4646eea8208ecb83f54ca035dd62d04f0d8101641a4f487f2c695c | 8446834f0edd1e71a2dcaffc09b80c7367abf3407263a8998354a2d20c1766bb | c1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8]>>[C:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 60 | CELSIUS | 1 | HOUR | To a stirred solution of DL -2 hydroxypropionic acid (9.0 g, 100 mmole) in 100 ml dry DMF was added potassium tert-butoxide (12.34 g, 110 mmole) and the mixture was stirred for one hour at 60° C. 4-methoxybenzyl chloride (18.8 g 120 mmole) was added and the mixture was stirred for eight hours at 60° C. The mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ester | null | null | c1ccccc1 | HCl | CN(C)C=O | 60 | 1 | CC(O)C(=O)O.COc1ccc(CCl)cc1>CN(C)C=O>COc1ccc(COC(=O)C(C)O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-edeb5c0877c6433683ae07456348746b | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.COc1ccc(COC(=O)C(C)O)cc1>>COc1ccc(COC(=O)C(C)OC(=O)[C@@H](NC(=O)OCc2ccccc2)C(C)C)cc1 | OC(C(=O)OCC1=CC=C(C=C1)OC)C.C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)O.C1CCC(CC1)N=C=NC2CCCCC2>>C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OC(C(=O)OCC1=CC=C(C=C1)OC)C | O[C:14](=[O:15])[C@@H:16]([NH:17][C:18](=[O:19])[O:20][CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)[CH:28]([CH3:29])[CH3:30].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][C:9](=[O:10])[CH:11]([CH3:12])[OH:13])[cH:31][cH:32]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][C:9](=[O:10])[CH:11]([CH3:12])[O:13... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.COc1ccc(COC(=O)C(C)O)cc1 | COc1ccc(COC(=O)C(C)OC(=O)[C@@H](NC(=O)OCc2ccccc2)C(C)C)cc1 | null | CN(C)C=1C=CN=CC1 | ClCCl | Acylation | Esterification of Carboxylic Acids | e916c5b009194e30c618975b40d7a233bfcf81339e65494c4e365f67cc5e011d | 12ba7405a548c6b1674f05065819c74f53f1b6165cd54e84e1f2f208042fe660 | O=C(CNC(=O)OCc1ccccc1)OCC(=O)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7].[C:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[C:12](-[C;D1;H3:13])-[OH;D1;+0:14]>>[C:4]-[C:3](-[#7:5]-[C:6]=[O;D1;H0:7])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:14]-[C:12](-[C;D1;H3:13])-[C:10](=[O;D1;H0:11])-[#8:9]-[C:8] | null | [] | null | null | 8 | HOUR | To a solution of 4-methoxybenzyl 2-hydroxypropionate (4.2 g, 20 mmole), N-CBZ-L-valine (5.02 g, 20 mmole) and DMAP (0.24 g, 2 mmole) in 100 ml dichloromethane was added a solution of DCC (4.54 g, 22 mmole) and the mixture was stirred overnight at room temperature. The mixture was cooled to 5° C. and the urethane was fi... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary alcohol | Ester | null | null | c1ccccc1.c1ccccc1 | HO- | CN(C)C=1C=CN=CC1.ClCCl | null | 8 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.COc1ccc(COC(=O)C(C)O)cc1>CN(C)C=1C=CN=CC1.ClCCl>COc1ccc(COC(=O)C(C)OC(=O)[C@@H](NC(=O)OCc2ccccc2)C(C)C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e8eadd3b067844bca8812cc13ec1e10c | COc1ccc(COC(=O)C(C)OC(=O)[C@@H](NC(=O)OCc2ccccc2)C(C)C)cc1>>CC(OC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(=O)O | C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OC(C(=O)OCC1=CC=C(C=C1)OC)C.FC(C(=O)O)(F)F>>C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)OC(C(=O)O)C | COc1ccc(C[O:23][C:21]([CH:2]([CH3:1])[O:3][C:4](=[O:5])[C@@H:6]([NH:7][C:8](=[O:9])[O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[CH:18]([CH3:19])[CH3:20])=[O:22])cc1>>[CH3:1][CH:2]([O:3][C:4](=[O:5])[C@@H:6]([NH:7][C:8](=[O:9])[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[CH:18]([CH3:19])[CH3:... | COc1ccc(COC(=O)C(C)OC(=O)[C@@H](NC(=O)OCc2ccccc2)C(C)C)cc1 | CC(OC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(=O)O | null | null | ClCCl | Reduction | Ester saponification (alkyl deprotection) | af4a00273af84ecb3074b1842201a78a3aac9a41d2050132ad8c8c1c9d796dee | 8d997f8b7994d8c9cf23425771b3f80d4d4830ac4e3d6552f381db244a5a65c5 | c1ccccc1 | C-O-c1:c:c:c(-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]):c:c:1>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | 1 | HOUR | To a solution of 4-methoxybenzyl 2-(N-CBZ-L-valyloxy)-propionate (7.8 g, 17.5 mmole) in dichloromethane (100 ml) was added trifluoroacetic acid (10 ml) and the solution was stirred for one hour at room temperature. The solution was evaporated under reduced pressure and the product was isolated by silica gel column chro... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether | Carboxylic acid | c1ccccc1 | null | c1ccccc1 | HO- | ClCCl | null | 1 | COc1ccc(COC(=O)C(C)OC(=O)[C@@H](NC(=O)OCc2ccccc2)C(C)C)cc1>ClCCl>CC(OC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5ea8029c5565435aad47984724f08609 | O=C1CCC(=O)O1.OCc1ccccc1>>O=C(O)CCC(=O)OCc1ccccc1 | C(CC(O)(C(=O)O)CC(=O)O)(=O)O.C(C1=CC=CC=C1)O.N1=CC=CC=C1.C1(CCC(=O)O1)=O>>C(C1=CC=CC=C1)OC(CCC(=O)O)=O | [O:1]=[C:2]1[O:3][C:6](=[O:7])[CH2:5][CH2:4]1.[OH:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1 | O=C1CCC(=O)O1.OCc1ccccc1 | O=C(O)CCC(=O)OCc1ccccc1 | null | CN(C1=CC=NC=C1)C | C(Cl)Cl | Protection | OtherReaction | 4d42d7d8bd0730c96932c909b16e8978d1df708884f50ef85240f28185bc7156 | 270493bb1736fbee778267cc9a23b684a84d6981f75eccd61f548310bd2b7198 | c1ccccc1 | [O;D1;H0:1]=[C:2]1-[C:3]-[C:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-1.[OH;D1;+0:8]-[C:9]-[c:10]>>[O;D1;H0:1]=[C:2](-[OH;D1;+0:7])-[C:3]-[C:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[O;H0;D2;+0:8]-[C:9]-[c:10] | null | [] | null | null | 30 | MINUTE | Succinic anhydride (30 g, 300 mmole) was dissolved in methylene chloride (300 ml). To the solution were added benzyl alcohol (10.2 ml, 100 mmole), 4-dimethylaminopyridine (1.22 g, 10 mmole) and pyridine (48 ml). After 3 hours the reaction mixture was poured in to citric acid aqueous solution. The organic phase was conc... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary alcohol | Carboxylic acid.Ester | C1CCOC1 | null | c1ccccc1 | null | CN(C1=CC=NC=C1)C.C(Cl)Cl | null | 0.5 | O=C1CCC(=O)O1.OCc1ccccc1>CN(C1=CC=NC=C1)C.C(Cl)Cl>O=C(O)CCC(=O)OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a7826aa50cc047a29967dc9daa70be1e | ClCI.O=C(O)CCC(=O)OCc1ccccc1>>O=C(CCC(=O)OCc1ccccc1)OCCl | C(C1=CC=CC=C1)OC(CCC(=O)O)=O.[OH-].C(CCC)[N+](CCCC)(CCCC)CCCC.ClCI>>ClCOC(CCC(=O)OCC1=CC=CC=C1)=O | I[CH2:16][Cl:17].[O:1]=[C:2]([CH2:3][CH2:4][C:5](=[O:6])[O:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[OH:15]>>[O:1]=[C:2]([CH2:3][CH2:4][C:5](=[O:6])[O:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[O:15][CH2:16][Cl:17] | ClCI.O=C(O)CCC(=O)OCc1ccccc1 | O=C(CCC(=O)OCc1ccccc1)OCCl | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2f16a3cac6d3c4085515a42267501b7a0eef68b042dbe72a334a9b3dd1458b44 | 20b23d23df2ca888376bbfdf646588e67491b315935b071cb9ba310488e4ee8f | c1ccccc1 | I-[CH2;D2;+0:1]-[Cl;D1;H0:2].[C:3]-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6]>>[C:3]-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[Cl;D1;H0:2] | null | [] | null | null | 18 | HOUR | Succinic acid monobenzyl ester (4.16 g, 20 mmole) was dissolved in dioxane (20 ml). To the solution was added tetrabutylammonium hydroxide aqueous solution (40%, 11.6 ml, 18 mmole). The solution was dried in vacuo and coevaporated with toluene several times. The residue was dissolved in methylene chloride (60 ml) and t... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Carboxylic acid | Primary halide.Ester | null | null | c1ccccc1 | HI | O1CCOCC1 | null | 18 | ClCI.O=C(O)CCC(=O)OCc1ccccc1>O1CCOCC1>O=C(CCC(=O)OCc1ccccc1)OCCl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6670ce32e0b94bc78f210052339ddcd9 | O=C(CCC(=O)OCc1ccccc1)OCCl.[I-]>>O=C(CCC(=O)OCc1ccccc1)OCI | ClCOC(CCC(=O)OCC1=CC=CC=C1)=O.[I-].[Na+]>>ICOC(CCC(=O)OCC1=CC=CC=C1)=O | Cl[CH2:16][O:15][C:2](=[O:1])[CH2:3][CH2:4][C:5](=[O:6])[O:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[I-:17]>>[O:1]=[C:2]([CH2:3][CH2:4][C:5](=[O:6])[O:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[O:15][CH2:16][I:17] | O=C(CCC(=O)OCc1ccccc1)OCCl.[I-] | O=C(CCC(=O)OCc1ccccc1)OCI | null | null | C(C)#N | Functional Group Interconversion | OtherReaction | 10bee13c50a4ba107934328c21250869f883899fc8944cf8a0ebee609aa1691d | fe69d77c5ffecf9aa0236c58528d10fdb0294a434868899e60e585d0629b72f9 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3](-[C:4])=[O;D1;H0:5].[I-;H0;D0:6]>>[C:4]-[C:3](=[O;D1;H0:5])-[#8:2]-[CH2;D2;+0:1]-[I;H0;D1;+0:6] | null | [] | null | null | null | null | 3-Benzyloxycarbonylpropionic acid chloromethyl ester (2 g, 1.38 mmole) was dissolved in acetonitrile (30 ml). Sodium iodide (1.6 g, 10.9 mmole) was added to the solution. After reaction at 70° C. for 3 hr, the reaction mixture was filtered and the residue was dissolved in methylene chloride (20 ml) and refiltered. The ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Primary halide | null | null | c1ccccc1 | Other | C(C)#N | null | null | O=C(CCC(=O)OCc1ccccc1)OCCl.[I-]>C(C)#N>O=C(CCC(=O)OCc1ccccc1)OCI |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3d76282a1f9143b792bd2547fb2fed39 | O=C(O)CCCBr.OCc1ccccc1>>O=C(CCCBr)OCc1ccccc1 | C([O-])(O)=O.[Na+].C(C1=CC=CC=C1)O.BrCCCC(=O)O.C(C)N(CC)CC>>C(C1=CC=CC=C1)OC(CCCBr)=O | O[C:2](=[O:1])[CH2:3][CH2:4][CH2:5][Br:6].[OH:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][Br:6])[O:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1 | O=C(O)CCCBr.OCc1ccccc1 | O=C(CCCBr)OCc1ccccc1 | null | null | S(=O)(Cl)Cl | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[OH;D1;+0:5]-[C:6]-[c:7]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:5]-[C:6]-[c:7] | null | [] | -50 | CELSIUS | 4 | HOUR | 4-bromobutyric acid (10.6 g, 60 mmole) was dissolved in thionyl chloride (20 mml), and the reaction was kept for 4 hr. The solution was evaporated and coevaporated with toluene several times. The residue was redissolved in dichloromethane (120 ml), and then benzyl alcohol (4.14 ml, 40 mmole) was added. The solution was... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1 | HO- | S(=O)(Cl)Cl | -50 | 4 | O=C(O)CCCBr.OCc1ccccc1>S(=O)(Cl)Cl>O=C(CCCBr)OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-22938041f184471290a132a36fbb3439 | CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)O.O=C(CCCBr)OCc1ccccc1>>CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCCCC(=O)OCc1ccccc1 | C([O-])(O)=O.[Na+].[OH-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(=O)(OC(C)(C)C)N[C@@H](C(C)C)C(=O)O.C(C1=CC=CC=C1)OC(CCCBr)=O>>C(C1=CC=CC=C1)OC(CCCOC([C@@H](NC(=O)OC(C)(C)C)C(C)C)=O)=O | [CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[C:13](=[O:14])[OH:15].Br[CH2:16][CH2:17][CH2:18][C:19](=[O:20])[O:21][CH2:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[C:13](=[O:14])[O:15]... | CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)O.O=C(CCCBr)OCc1ccccc1 | CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCCCC(=O)OCc1ccccc1 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 06c4f868ad4646eea8208ecb83f54ca035dd62d04f0d8101641a4f487f2c695c | 8446834f0edd1e71a2dcaffc09b80c7367abf3407263a8998354a2d20c1766bb | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4](-[#8:5])=[O;D1;H0:6].[C:7]-[C:8](=[O;D1;H0:9])-[OH;D1;+0:10]>>[#8:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:10]-[C:8](-[C:7])=[O;D1;H0:9] | null | [] | null | null | 18 | HOUR | N-Boc-L-valine (1.3 g, 6 mmole) was dissolved in dioxane (5 ml). To the solution was added tetrabutylammonium hydroxide aqueous solution (40%, 3.8 ml, 6 mmole), and the solution was evaporated and coevaporated with toluene several times. The residue was dissolved in DMF (15 ml) and 4-bromobutyric acid benzyl ester (1.2... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ester | null | null | c1ccccc1 | HBr | O1CCOCC1 | null | 18 | CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)O.O=C(CCCBr)OCc1ccccc1>O1CCOCC1>CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCCCC(=O)OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-018eebc2a02e453fa7802c31187ef152 | CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCCCC(=O)OCc1ccccc1>>CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCCCC(=O)O | C(C1=CC=CC=C1)OC(CCCOC([C@@H](NC(=O)OC(C)(C)C)C(C)C)=O)=O>>C(=O)(OC(C)(C)C)N[C@@H](C(C)C)C(=O)OCCCC(=O)O | c1ccc(C[O:21][C:19]([CH2:18][CH2:17][CH2:16][O:15][C:13]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])=[O:14])=[O:20])cc1>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[C:13](=[O:14])[O:15][CH2:16][CH2:17][CH2:18][C:19](=[O:20])[OH:2... | CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCCCC(=O)OCc1ccccc1 | CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCCCC(=O)O | null | [Pd] | C(C)(=O)OCC.CO | Deprotection | Ester saponification (alkyl deprotection) | 86a971d3e4f88009ab4c98512e9f1deb51b2f0ce5cbd068cc61ae878c1e58e2a | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | null | [C:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-C-c1:c:c:c:c:c:1>>[C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4] | null | [] | null | null | 2 | HOUR | To a solution of 4-(N-Boc-L-valyloxy)butyric acid benzyl ester (1.2 g, 3 mmole) in ethyl acetate/methanol (5 ml/5 ml) was added palladium black (20 mg). The reaction mixture was kept under hydrogen at atmospheric pressure for 2 hr. The suspension was filtered through Celite and dried, giving the title product, 840 mg.
... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | c1ccccc1 | null | null | Other | [Pd].C(C)(=O)OCC.CO | null | 2 | CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCCCC(=O)OCc1ccccc1>[Pd].C(C)(=O)OCC.CO>CC(C)[C@H](NC(=O)OC(C)(C)C)C(=O)OCCCC(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-215cdc25fad843078f46ce018c15b5cb | CC(C)(O)C(=O)O.COc1ccc(CCl)cc1>>COc1ccc(COC(=O)C(C)(C)O)cc1 | C(C)O.OC(C(=O)O)(C)C.COC1=CC=C(CCl)C=C1>>OC(C(=O)OCC1=CC=C(C=C1)OC)(C)C | [OH:8][C:9](=[O:10])[C:11]([CH3:12])([CH3:13])[OH:14].Cl[CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:16][cH:15]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][C:9](=[O:10])[C:11]([CH3:12])([CH3:13])[OH:14])[cH:15][cH:16]1 | CC(C)(O)C(=O)O.COc1ccc(CCl)cc1 | COc1ccc(COC(=O)C(C)(C)O)cc1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 06c4f868ad4646eea8208ecb83f54ca035dd62d04f0d8101641a4f487f2c695c | 8446834f0edd1e71a2dcaffc09b80c7367abf3407263a8998354a2d20c1766bb | c1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8]>>[C:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | 2-hydroxy isobutyric acid (1.56 g) was esterified by alkylation with 4-methoxybenzyl chloride by the method described in Example A-I-1, step a). The title compound (2.65 g) was obtained after silica gel column chromatography (0, 1, 2% ethanol in dichloromethane). Rf (2% MeOH/CHCl3) 0.45.
Conditions: See reaction.notes.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ester | null | null | c1ccccc1 | HCl | ClCCl | null | null | CC(C)(O)C(=O)O.COc1ccc(CCl)cc1>ClCCl>COc1ccc(COC(=O)C(C)(C)O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cd103c8f4bed475198a3058a6dfc2bc0 | CC(C)[C@H](O)C(=O)O.COc1ccc(CCl)cc1>>COc1ccc(COC(=O)[C@@H](O)C(C)C)cc1 | C(C)O.O[C@H](C(=O)O)C(C)C.COC1=CC=C(CCl)C=C1>>O[C@H](C(=O)OCC1=CC=C(C=C1)OC)C(C)C | [OH:8][C:9](=[O:10])[C@@H:11]([OH:12])[CH:13]([CH3:14])[CH3:15].Cl[CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:17][cH:16]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][C:9](=[O:10])[C@@H:11]([OH:12])[CH:13]([CH3:14])[CH3:15])[cH:16][cH:17]1 | CC(C)[C@H](O)C(=O)O.COc1ccc(CCl)cc1 | COc1ccc(COC(=O)[C@@H](O)C(C)C)cc1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 06c4f868ad4646eea8208ecb83f54ca035dd62d04f0d8101641a4f487f2c695c | 8446834f0edd1e71a2dcaffc09b80c7367abf3407263a8998354a2d20c1766bb | c1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8]>>[C:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | 2-hydroxy-3-methyl-(S)-(+)-butyric acid (1.77 g) was esterified by alkylation with 4-methoxybenzyl chloride by the method described in Example A-I-1, step a. The title compound (3.10 g) was obtained after silica gel column chromatography (0, 1, 2% ethanol in dichloromethane). Rf (2% MeOH/CHCl3) 0.50.
Conditions: See re... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ester | null | null | c1ccccc1 | HCl | ClCCl | null | null | CC(C)[C@H](O)C(=O)O.COc1ccc(CCl)cc1>ClCCl>COc1ccc(COC(=O)[C@@H](O)C(C)C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d1f715994313416e96876e3bf88df36c | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.COc1ccc(COC(=O)[C@@H](O)C(C)C)cc1>>COc1ccc(COC(=O)[C@@H](OC(=O)[C@@H](NC(=O)OCc2ccccc2)C(C)C)C(C)C)cc1 | C(C)O.O[C@H](C(=O)OCC1=CC=C(C=C1)OC)C(C)C.C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)O>>C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)O[C@H](C(=O)OCC1=CC=C(C=C1)OC)C(C)C | O[C:13](=[O:14])[C@@H:15]([NH:16][C:17](=[O:18])[O:19][CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1)[CH:27]([CH3:28])[CH3:29].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][C:9](=[O:10])[C@@H:11]([OH:12])[CH:30]([CH3:31])[CH3:32])[cH:33][cH:34]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][C:9](=[O:10])[C@... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.COc1ccc(COC(=O)[C@@H](O)C(C)C)cc1 | COc1ccc(COC(=O)[C@@H](OC(=O)[C@@H](NC(=O)OCc2ccccc2)C(C)C)C(C)C)cc1 | null | null | ClCCl | Acylation | Esterification of Carboxylic Acids | e916c5b009194e30c618975b40d7a233bfcf81339e65494c4e365f67cc5e011d | 12ba7405a548c6b1674f05065819c74f53f1b6165cd54e84e1f2f208042fe660 | O=C(CNC(=O)OCc1ccccc1)OCC(=O)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7].[C:8]-[C:9](-[OH;D1;+0:10])-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14]>>[C:4]-[C:3](-[#7:5]-[C:6]=[O;D1;H0:7])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:10]-[C:9](-[C:8])-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14] | null | [] | null | null | null | null | 4-Methoxybenzyl 2-hydroxy-3-methyl-(S)-(+)-butyrate was acylated with N-benzyloxycarbonyl-L-valine by the method described in Example A-I-1, step b. The title compound (5.74 g) was obtained after silica gel column chromatography (0, 1, 1.5% ethanol in dichloromethane). Rf (2% MeOH/CHCl3) 0.70.
Conditions: See reaction.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary alcohol | Ester | null | null | c1ccccc1.c1ccccc1 | HO- | ClCCl | null | null | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O.COc1ccc(COC(=O)[C@@H](O)C(C)C)cc1>ClCCl>COc1ccc(COC(=O)[C@@H](OC(=O)[C@@H](NC(=O)OCc2ccccc2)C(C)C)C(C)C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-acbc843521ff4b1886d8f94e72a0578d | COc1ccc(COC(=O)[C@@H](OC(=O)[C@@H](NC(=O)OCc2ccccc2)C(C)C)C(C)C)cc1>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O[C@H](C(=O)O)C(C)C | C(C)O.C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)O[C@H](C(=O)OCC1=CC=C(C=C1)OC)C(C)C>>C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)O[C@H](C(=O)O)C(C)C | COc1ccc(C[O:22][C:20]([C@@H:19]([O:18][C:16]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)=[O:17])[CH:23]([CH3:24])[CH3:25])=[O:21])cc1>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C:16](=[O:17])[O... | COc1ccc(COC(=O)[C@@H](OC(=O)[C@@H](NC(=O)OCc2ccccc2)C(C)C)C(C)C)cc1 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O[C@H](C(=O)O)C(C)C | null | null | ClCCl | Reduction | Ester saponification (alkyl deprotection) | af4a00273af84ecb3074b1842201a78a3aac9a41d2050132ad8c8c1c9d796dee | 8d997f8b7994d8c9cf23425771b3f80d4d4830ac4e3d6552f381db244a5a65c5 | c1ccccc1 | C-O-c1:c:c:c(-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]):c:c:1>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | null | null | 4-methoxybenzyl 2-(N-benzyloxycarbonyl-L-valyloxy)-3-methyl-(S)-(+)-butyrate was de-esterified by the method described in Example A-I-1, step c. The title compound (3.41 g) was obtained after silica gel column chromatography (2, 10, 20% ethanol in dichloromethane). Rf (2% MeOH/CHCl3) 0.45. The compound may be activated... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether | Carboxylic acid | c1ccccc1 | null | c1ccccc1 | HO- | ClCCl | null | null | COc1ccc(COC(=O)[C@@H](OC(=O)[C@@H](NC(=O)OCc2ccccc2)C(C)C)C(C)C)cc1>ClCCl>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)O[C@H](C(=O)O)C(C)C |
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