dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-eb92e10054a6426ebcb60995047ce53d | Cc1cc(SCC=C(c2ccc(Br)cc2)c2ccc(Br)cc2)ccc1OCC(=O)O.OB(O)c1ccc(-c2ccccc2)cc1>>Cc1cc(SCC=C(c2ccc(-c3ccc(-c4ccccc4)cc3)cc2)c2ccc(-c3ccc(-c4ccccc4)cc3)cc2)ccc1OCC(=O)O | BrC1=CC=C(C=C1)C(=CCSC1=CC(=C(OCC(=O)O)C=C1)C)C1=CC=C(C=C1)Br.B(C=1C=CC(=CC1)C=2C=CC=CC2)(O)O.[F-].[K+].[Cl-].[NH4+]>>C1(=CC=C(C=C1)C(=CCSC1=CC(=C(OCC(=O)O)C=C1)C)C1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=CC=C1)C1=CC=C(C=C1)C1=CC=CC=C1 | Br[c:12]1[cH:11][cH:10][c:9]([C:8](=[CH:7][CH2:6][S:5][c:4]2[cH:3][c:2]([CH3:1])[c:47]([O:48][CH2:49][C:50](=[O:51])[OH:52])[cH:46][cH:45]2)[c:27]2[cH:13][cH:29][c:30](Br)[cH:43][cH:44]2)[cH:26][cH:25]1.OB(O)[c:34]1[cH:14][cH:15][c:16](-[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[cH:23][cH:41]1>>[CH3:1][c:2]1[cH:3][c:... | Cc1cc(SCC=C(c2ccc(Br)cc2)c2ccc(Br)cc2)ccc1OCC(=O)O.OB(O)c1ccc(-c2ccccc2)cc1 | Cc1cc(SCC=C(c2ccc(-c3ccc(-c4ccccc4)cc3)cc2)c2ccc(-c3ccc(-c4ccccc4)cc3)cc2)ccc1OCC(=O)O | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C | C1CCOC1 | C-C Coupling | OtherReaction | a52ac3e68168ca2e107f5652b3de2c779a4e5fb59258bdf298eab75ddc044749 | b431b00445693c7ae33759145152dfe407ee85c3562148bfc9cb7e8a06213bb6 | C(CSc1ccccc1)=C(c1ccc(-c2ccc(-c3ccccc3)cc2)cc1)c1ccc(-c2ccc(-c3ccccc3)cc2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](-[C:5](=[C:6]-[C:7])-[c;H0;D3;+0:8]2:[c:9]:[c:10]:[c;H0;D3;+0:11](-Br):[cH;D2;+0:12]:[cH;D2;+0:13]:2):[c:14]:[c:15]:1.O-B(-O)-[c;H0;D3;+0:16]1:[cH;D2;+0:17]:[c:18]:[c:19](-[c:20]):[cH;D2;+0:21]:[cH;D2;+0:22]:1>>[C:7]-[C:6]=[C:5](-[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:13]2:[... | null | [] | 50 | CELSIUS | 2 | HOUR | In an evaporated schlenk flask kept under nitrogen atmosphere were added {4-[3,3-bis-(4-bromo-phenyl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid (225 mg, 0.41 mmol, example 1, step A–B, biphenylboronic acid (163 mg, 0.8 mmol), KF (79 mg, 1.35 mmol), Pd2(dba)3 (23 mg, 25 mmol) and Pd(P(t-Bu)3)2 (26 mg, 51 mmol). THF (... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | Br-.B | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.C1CCOC1 | 50 | 2 | Cc1cc(SCC=C(c2ccc(Br)cc2)c2ccc(Br)cc2)ccc1OCC(=O)O.OB(O)c1ccc(-c2ccccc2)cc1>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.C1CCOC1>Cc1cc(SCC=C(c2ccc(-c3ccc(-c4ccccc4)cc3)... |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c5ebe0b0aed846cc89d4466e7663f9a1 | CCOC(=O)COc1ccc(S)cc1C(F)(F)F.OCC=C(c1ccc(-c2cccnc2)cc1)c1ccc(-c2cccnc2)cc1>>CCOC(=O)COc1ccc(SCC=C(c2ccc(-c3cccnc3)cc2)c2ccc(-c3cccnc3)cc2)cc1C(F)(F)F | C(C)OC(COC1=C(C=C(C=C1)S)C(F)(F)F)=O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1CCN(CC1)C(=O)N=NC(=O)N2CCCCC2.N1=CC(=CC=C1)C1=CC=C(C=C1)C(=CCO)C1=CC=C(C=C1)C=1C=NC=CC1>>C(C)OC(COC1=C(C=C(C=C1)SCC=C(C1=CC=C(C=C1)C=1C=NC=CC1)C1=CC=C(C=C1)C=1C=NC=CC1)C(F)(F)F)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([SH:12])[cH:40][c:41]1[C:42]([F:43])([F:44])[F:45].O[CH2:13][CH:14]=[C:15]([c:16]1[cH:17][cH:18][c:19](-[c:20]2[cH:21][cH:22][cH:23][n:24][cH:25]2)[cH:26][cH:27]1)[c:28]1[cH:29][cH:30][c:31](-[c:32]2[cH:33][cH:34][cH:35][n:36][cH:37]2)[cH:38][cH:39]1... | CCOC(=O)COc1ccc(S)cc1C(F)(F)F.OCC=C(c1ccc(-c2cccnc2)cc1)c1ccc(-c2cccnc2)cc1 | CCOC(=O)COc1ccc(SCC=C(c2ccc(-c3cccnc3)cc2)c2ccc(-c3cccnc3)cc2)cc1C(F)(F)F | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | c119424abb7b621e5fb126e8156c5e4310815e8f2d609f48f2eb427b327d29ac | c1ccf05c97341d9cf75acae4c03f7d5a8212340a35905af6c8d60b4ccc775d1f | C(CSc1ccccc1)=C(c1ccc(-c2cccnc2)cc1)c1ccc(-c2cccnc2)cc1 | O-[CH2;D2;+0:1]-[C:2]=[C:3](-[c:4])-[c:5].[SH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[S;H0;D2;+0:6]-[CH2;D2;+0:1]-[C:2]=[C:3](-[c:4])-[c:5]):[c:9] | null | [] | null | null | 5 | MINUTE | Triphenylphosphine (138 mg, 0.68 mmol) and ADDP (173 mg, 0.68 mmol) were added to a solution of 3,3-bis-(4-pyridin-3-yl-phenyl)-prop-2-en-1-ol (100 mg, 0.27 mmol) in THF (5 ml) at 0° C. The reaction mixture was stirred for 5 min under nitrogen atmosphere. (4-Mercapto-2-trifluoromethyl-phenoxy)-acetic acid ethyl ester (... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic thiol | Monosulfide | null | null | c1ccccc1.c1ccccc1.c1ccncc1.c1ccccc1.c1ccncc1 | HO- | C1CCOC1 | null | 0.083333 | CCOC(=O)COc1ccc(S)cc1C(F)(F)F.OCC=C(c1ccc(-c2cccnc2)cc1)c1ccc(-c2cccnc2)cc1>C1CCOC1>CCOC(=O)COc1ccc(SCC=C(c2ccc(-c3cccnc3)cc2)c2ccc(-c3cccnc3)cc2)cc1C(F)(F)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e72a29a49a7e4e14b6c97a72e07036ea | CCOC(=O)COc1ccc(SCC=C(c2ccc(-c3cccnc3)cc2)c2ccc(-c3cccnc3)cc2)cc1C(F)(F)F>>O=C(O)COc1ccc(SCC=C(c2ccc(-c3cccnc3)cc2)c2ccc(-c3cccnc3)cc2)cc1C(F)(F)F | C(C)OC(COC1=C(C=C(C=C1)SCC=C(C1=CC=C(C=C1)C=1C=NC=CC1)C1=CC=C(C=C1)C=1C=NC=CC1)C(F)(F)F)=O>>N1=CC(=CC=C1)C1=CC=C(C=C1)C(=CCSC1=CC(=C(OCC(=O)O)C=C1)C(F)(F)F)C1=CC=C(C=C1)C=1C=NC=CC1 | CC[O:3][C:2](=[O:1])[CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([S:10][CH2:11][CH:12]=[C:13]([c:14]2[cH:15][cH:16][c:17](-[c:18]3[cH:19][cH:20][cH:21][n:22][cH:23]3)[cH:24][cH:25]2)[c:26]2[cH:27][cH:28][c:29](-[c:30]3[cH:31][cH:32][cH:33][n:34][cH:35]3)[cH:36][cH:37]2)[cH:38][c:39]1[C:40]([F:41])([F:42])[F:43]>>[O:1]=[C:2]([OH... | CCOC(=O)COc1ccc(SCC=C(c2ccc(-c3cccnc3)cc2)c2ccc(-c3cccnc3)cc2)cc1C(F)(F)F | O=C(O)COc1ccc(SCC=C(c2ccc(-c3cccnc3)cc2)c2ccc(-c3cccnc3)cc2)cc1C(F)(F)F | null | null | [OH-].[Na+].C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | C(CSc1ccccc1)=C(c1ccc(-c2cccnc2)cc1)c1ccc(-c2cccnc2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | null | null | A solution of {4-[3,3-bis-(4-pyridin-3-yl-phenyl)-allylsulfanyl]-2-trifluoromethyl-phenoxy}-acetic acid ethyl ester (70 mg, 0.1 mmol) in ethanol (10 ml) and 1N NaOH (0.5 ml) was stirred at 75° C. for 1 h. The reaction mixture was evaporated and the residue was treated with 1N HCl (0.7 ml) and extracted with methylene c... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccncc1.c1ccccc1.c1ccncc1 | Other | [OH-].[Na+].C(C)O | null | null | CCOC(=O)COc1ccc(SCC=C(c2ccc(-c3cccnc3)cc2)c2ccc(-c3cccnc3)cc2)cc1C(F)(F)F>[OH-].[Na+].C(C)O>O=C(O)COc1ccc(SCC=C(c2ccc(-c3cccnc3)cc2)c2ccc(-c3cccnc3)cc2)cc1C(F)(F)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-25de6e20d68e4a01a05d61c43866a6f5 | CC1(C)OC(=O)CC(=O)O1.Nc1cccc(Br)c1>>CC1(C)OC(=O)C(=CNc2cccc(Br)c2)C(=O)O1 | C(OCC)(OCC)OCC.CC1(OC(=O)CC(=O)O1)C.BrC=1C=C(N)C=CC1.BrC=1C=C(N)C=CC1>>BrC=1C=C(C=CC1)NC=C1C(OC(OC1=O)(C)C)=O | [CH3:1][C:2]1([CH3:3])[O:4][C:5](=[O:6])[CH2:7][C:17](=[O:18])[O:19]1.[NH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]([Br:15])[cH:16]1>>[CH3:1][C:2]1([CH3:3])[O:4][C:5](=[O:6])[C:7](=[CH:8][NH:9][c:10]2[cH:11][cH:12][cH:13][c:14]([Br:15])[cH:16]2)[C:17](=[O:18])[O:19]1 | CC1(C)OC(=O)CC(=O)O1.Nc1cccc(Br)c1 | CC1(C)OC(=O)C(=CNc2cccc(Br)c2)C(=O)O1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 16f6e689ff4988a3075463cf8c372a4929ef73d83eb11dd6443a2ba775713df7 | cb45d3f2664ea1c07edca6192a95c91d6c98f4c61196cc5a896d41447e7a94b5 | O=C1OCOC(=O)C1=CNc1ccccc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[#8:7]-[C:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:5]=[C:6]1-[#8:7]-[C:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[C;H0;D3;+0:12]-1=[C:13]-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 55 | CELSIUS | null | null | A mixture of triethyl orthoformate (154 grams (g), 1.04 moles (mol) and Meldrum's acid (142 g, 0.983 mol) was heated to 55° C. for 4 hours (h). After cooling to 50° C., a solution of 3-bromoaniline (162.6 g, 0.945 mol) in ethanol (300 mL) was added such that the temperature of the reaction was maintained between 50–55°... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Primary amine | Enamine | C1COCOC1 | C1COCOC1 | C1COCOC1.c1ccccc1 | Other | C(C)O | 55 | null | CC1(C)OC(=O)CC(=O)O1.Nc1cccc(Br)c1>C(C)O>CC1(C)OC(=O)C(=CNc2cccc(Br)c2)C(=O)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b3f9f78625db481c835ecd681b30b45a | O=[N+]([O-])O.Oc1ccnc2cc(Br)ccc12>>O=[N+]([O-])c1cnc2cc(Br)ccc2c1O | BrC1=CC=C2C(=CC=NC2=C1)O.[N+](=O)(O)[O-].[N+](=O)(O)[O-]>>BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])O | O[N+:2](=[O:1])[O-:3].[cH:4]1[cH:5][n:6][c:7]2[cH:8][c:9]([Br:10])[cH:11][cH:12][c:13]2[c:14]1[OH:15]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][n:6][c:7]2[cH:8][c:9]([Br:10])[cH:11][cH:12][c:13]2[c:14]1[OH:15] | O=[N+]([O-])O.Oc1ccnc2cc(Br)ccc12 | O=[N+]([O-])c1cnc2cc(Br)ccc2c1O | null | null | C(CC)(=O)O | Functional Group Addition | Aromatic nitration with HNO3 | 93c60f395fb4f0e5be7b3c9f5aae0bbd322ad57344c0d8df26b336a54b906179 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccc2ncccc2c1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[O;D1;H1:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[cH;D2;+0:10]:1>>[O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[c;H0;D3;+0:10]1:[c:9]:[#7;a:8]:[c:7]:[c:6]:[c:5]:1-[O;D1;H1:4] | 78.1 | [{"value": 78.1, "product": "BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred suspension of 7-bromoquinolin-4-ol (162 g, 0.723 mol) in propionic acid (1500 mL) was brought to 110° C. 70% Nitric acid (85 g) was added dropwise over 1 h such that the temperature was maintained between 110–115° C. After half of the nitric acid had been added, stirring became difficult due to the formation ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HO- | C(CC)(=O)O | null | null | O=[N+]([O-])O.Oc1ccnc2cc(Br)ccc12>C(CC)(=O)O>O=[N+]([O-])c1cnc2cc(Br)ccc2c1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-124d1086d4d44e1a9c954932a0b1a5e1 | O=P(Cl)(Cl)Cl.O=[N+]([O-])c1cnc2cc(Br)ccc2c1O>>O=[N+]([O-])c1cnc2cc(Br)ccc2c1Cl | BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])O.O=P(Cl)(Cl)Cl>>BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])Cl | O=P(Cl)(Cl)[Cl:15].O[c:14]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][n:6][c:7]2[cH:8][c:9]([Br:10])[cH:11][cH:12][c:13]21>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][n:6][c:7]2[cH:8][c:9]([Br:10])[cH:11][cH:12][c:13]2[c:14]1[Cl:15] | O=P(Cl)(Cl)Cl.O=[N+]([O-])c1cnc2cc(Br)ccc2c1O | O=[N+]([O-])c1cnc2cc(Br)ccc2c1Cl | null | null | null | Functional Group Interconversion | Alcohol to chloride_POCl3_para | 27014e1419adc48e7dd5f2024d7f933bb85e42d4ec6c57e509da2884d477d689 | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1ccc2ncccc2c1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[c:3](:[c:4]):[c:5](:[c:6]):[#7;a:7]:[c:8]:[c:9]:1-[#7;+:10]>>[#7;+:10]-[c:9]1:[c:8]:[#7;a:7]:[c:5](:[c:6]):[c:3](:[c:4]):[c;H0;D3;+0:2]:1-[Cl;H0;D1;+0:1] | null | [] | null | null | 45 | MINUTE | 7-Bromo-3-nitroquinolin-4-ol (42 g, 156 millimoles (mmol)) was suspended in POCl3 (130 mL) and brought to 102° C. under an atmosphere of N2. After 45 min, all of the solids had dissolved, so the reaction was cooled to room temperature (RT). The resulting solids were collected by filtration, washed with H2O, and then pa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HCl | null | null | 0.75 | O=P(Cl)(Cl)Cl.O=[N+]([O-])c1cnc2cc(Br)ccc2c1O>>O=[N+]([O-])c1cnc2cc(Br)ccc2c1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-630f53709a7641e4abb79b3ac6370174 | CC(C)CNc1c([N+](=O)[O-])cnc2cc(Br)ccc12>>CC(C)CNc1c(N)cnc2cc(Br)ccc12 | [O-]S(=O)S(=O)[O-].[Na+].[Na+].BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])NCC(C)C>>BrC1=CC=C2C(=C(C=NC2=C1)N)NCC(C)C | O=[N+:8]([O-])[c:7]1[c:6]([NH:5][CH2:4][CH:2]([CH3:1])[CH3:3])[c:17]2[c:11]([n:10][cH:9]1)[cH:12][c:13]([Br:14])[cH:15][cH:16]2>>[CH3:1][CH:2]([CH3:3])[CH2:4][NH:5][c:6]1[c:7]([NH2:8])[cH:9][n:10][c:11]2[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]12 | CC(C)CNc1c([N+](=O)[O-])cnc2cc(Br)ccc12 | CC(C)CNc1c(N)cnc2cc(Br)ccc12 | null | null | O.C(C)(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2ncccc2c1 | 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] | 135.6 | [{"value": 135.6, "product": "BrC1=CC=C2C(=C(C=NC2=C1)N)NCC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of Na2S2O4 (193 g) in H2O (1 L) was added to a boiling solution of (7-bromo-3-nitroquinolin-4-yl)isobutylamine (32.0 g, 99 mmol) in isopropanol (1 L). Upon complete addition, the reaction mixture was cooled to room temperature and the bulk of the isopropanol was removed on a rotary evaporator. The resulting ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2ncccc2c1 | Other | O.C(C)(C)O | null | null | CC(C)CNc1c([N+](=O)[O-])cnc2cc(Br)ccc12>O.C(C)(C)O>CC(C)CNc1c(N)cnc2cc(Br)ccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-162be3fc5e3f4ed98a5683cec7677ead | CC(C)CNc1c(N)cnc2cc(Br)ccc12.CCCCC(OC)(OC)OC>>CCCCc1nc2cnc3cc(Br)ccc3c2n1CC(C)C | BrC1=CC=C2C(=C(C=NC2=C1)N)NCC(C)C.C(CCCC)(OC)(OC)OC>>BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CC(C)C)CCCC | [NH2:6][c:7]1[cH:8][n:9][c:10]2[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]2[c:17]1[NH:18][CH2:19][CH:20]([CH3:21])[CH3:22].CO[C:5](OC)(OC)[CH2:4][CH2:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]3[c:17]2[n:18]1[CH2:19][CH:20]([CH3:21])[CH3:22] | CC(C)CNc1c(N)cnc2cc(Br)ccc12.CCCCC(OC)(OC)OC | CCCCc1nc2cnc3cc(Br)ccc3c2n1CC(C)C | null | Cl.N1=CC=CC=C1 | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 8d87c769e65778c9400c7f523e0409ecf0ffad86543cd9fdd6ef4b239323db96 | a60e703c3cf5c0d933aa031358d338c45d96ec82dec3fc2d9f5dce06b9dcc651 | c1ccc2c(c1)ncc1nc[nH]c12 | C-O-[C;H0;D4;+0:1](-O-C)(-O-C)-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1-[NH2;D1;+0:13]>>[C:4]-[C:5]-[n;H0;D3;+0:6]1:[c:7]2:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:2:[n;H0;D2;+0:13]:[c;H0;D3;+0:1]:1-[C:2]-[C:3] | 43.9 | [{"value": 43.9, "product": "BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CC(C)C)CCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 7-Bromo-N4-isobutylquinoline-3,4-diamine (39.4 g of crude material), trimethyl orthovalerate (32 g, 0.20 mol), and pyridine hydrochloride (0.31 g, 2.7 mmol) were combined with anhydrous toluene (500 mL) and heated to reflux for 30 min. The reaction was cooled to room temperature, concentrated, and the residue was purif... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Primary amine.Secondary amine | null | c1ccc2ncccc2c1 | c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12 | HO- | Cl.N1=CC=CC=C1.C1(=CC=CC=C1)C | null | null | CC(C)CNc1c(N)cnc2cc(Br)ccc12.CCCCC(OC)(OC)OC>Cl.N1=CC=CC=C1.C1(=CC=CC=C1)C>CCCCc1nc2cnc3cc(Br)ccc3c2n1CC(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fbc47495747e4abfa9aa3c4624c34f3b | CCCCc1nc2c(N)nc3cc(Br)ccc3c2n1CC(C)C.OB(O)c1ccccc1>>CCCCc1nc2c(N)nc3cc(-c4ccccc4)ccc3c2n1CC(C)C | BrC=1C=CC=2C3=C(C(=NC2C1)N)N=C(N3CC(C)C)CCCC.C1(=CC=CC=C1)B(O)O>>C(CCC)C=1N(C2=C(C(=NC=3C=C(C=CC23)C2=CC=CC=C2)N)N1)CC(C)C | Br[c:13]1[cH:12][c:11]2[n:10][c:8]([NH2:9])[c:7]3[n:6][c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[n:24]([CH2:25][CH:26]([CH3:27])[CH3:28])[c:23]3[c:22]2[cH:21][cH:20]1.OB(O)[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13](-[c:14]4[cH:15][cH:16][c... | CCCCc1nc2c(N)nc3cc(Br)ccc3c2n1CC(C)C.OB(O)c1ccccc1 | CCCCc1nc2c(N)nc3cc(-c4ccccc4)ccc3c2n1CC(C)C | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 89ee2e97ba79660eddf3dfa788334e60a83082a3d4afa6ed050c5f1f85789150 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc3c(c2)ncc2nc[nH]c23)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[c:6](:[#7;a:7]):[c:8](:[#7;a:9]):[c:10]:2:[c:11]:[c:12]:1.O-B(-O)-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16]:[c:17]>>[#7;a:9]:[c:8]1:[c:10]2:[c:11]:[c:12]:[c;H0;D3;+0:1](-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16]:[c:17]):[c:2]:[c:3]:2:[#7;a:4]:[c:5]:[c:6]:1:[#7;a:7] | null | [] | null | null | null | null | 7-Bromo-2-butyl-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine and benzeneboronic acid were coupled according to the general procedure described in Part J of Example 1. Purification by chromatography on silica gel (20% acetone in toluene to 60% acetone in toluene gradient) afforded 2-butyl-1-isobutyl-7-phenyl-1H-imidazo[... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)ncc1[nH]cnc12.c1ccccc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccccc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccccc1 | HBr.B | null | null | null | CCCCc1nc2c(N)nc3cc(Br)ccc3c2n1CC(C)C.OB(O)c1ccccc1>>CCCCc1nc2c(N)nc3cc(-c4ccccc4)ccc3c2n1CC(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0657f11f0a2c4022942778090163fb5a | CCCCc1nc2cnc3cc(-c4ccc(OC)cc4OC)ccc3c2n1CC(C)C.CCCCc1nc2cnc3cc(Br)ccc3c2n1CC(C)C.COc1ccc(B(O)O)c(OC)c1>>CCCCc1nc2c(N)nc3cc(-c4ccc(OC)cc4OC)ccc3c2n1CC(C)C | BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CC(C)C)CCCC.COC1=C(C=CC(=C1)OC)B(O)O.C(CCC)C=1N(C2=C(C=NC=3C=C(C=CC23)C2=C(C=C(C=C2)OC)OC)N1)CC(C)C>>C(CCC)C=1N(C2=C(C(=NC=3C=C(C=CC23)C2=C(C=C(C=C2)OC)OC)N)N1)CC(C)C | COc1ccc(-[c:13]2[cH:12][c:11]3[n:9][cH:8][c:7]4[n:6][c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[n:28]([CH2:29][CH:30]([CH3:31])[CH3:32])[c:27]4[c:26]3[cH:25][cH:24]2)c(OC)c1.CCCCc1nc2c[n:10]c3cc(Br)ccc3c2n1CC(C)C.OB(O)[c:14]1[cH:15][cH:16][c:17]([O:18][CH3:19])[cH:20][c:21]1[O:22][CH3:23]>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:... | CCCCc1nc2cnc3cc(-c4ccc(OC)cc4OC)ccc3c2n1CC(C)C.CCCCc1nc2cnc3cc(Br)ccc3c2n1CC(C)C.COc1ccc(B(O)O)c(OC)c1 | CCCCc1nc2c(N)nc3cc(-c4ccc(OC)cc4OC)ccc3c2n1CC(C)C | null | null | null | C-C Coupling | OtherReaction | cb4cc0022a7341fde0f95bc21a175e59667459f7912fea6931da43876194ab9c | 211bc1f53e80deec1d6ffae932269931f18571c43be73f2a28a363359aa16d14 | c1ccc(-c2ccc3c(c2)ncc2nc[nH]c23)cc1 | Br-c1:c:c:c2:c(:[n;H0;D2;+0:1]:c:c3:n:c(-C-C-C-C):n(-C-C(-C)-C):c:3:2):c:1.C-O-c1:c:c:c(-[c;H0;D3;+0:2]2:[c:3]:[c;H0;D3;+0:4]3:[n;H0;D2;+0:5]:[cH;D2;+0:6]:[c:7]4:[#7;a:8]:[c:9]:[#7;a:10](-[C:11]):[c:12]:4:[c:13]:3:[c:14]:[c:15]:2):c(-O-C):c:1.O-B(-O)-[c;H0;D3;+0:16](:[c:17]:[c:18]):[c:19](-[#8:20]):[c:21]>>[#8:20]-[c:1... | null | [] | null | null | null | null | 7-Bromo-2-butyl-1-isobutyl-1H-imidazo[4,5-c]quinoline and 2,4-dimethoxybenzeneboronic acid were coupled according to the general procedure described in Part J of Example 1. The resulting 2-butyl-7-(2,4-dimethoxyphenyl)-1-isobutyl-1H-imidazo[4,5-c]quinoline was oxidized and then aminated according to the general procedu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Ether.Boronic acid | Primary amine | c1ccccc1.c1ccc2c(c1)ncc1[nH]cnc12.c1ccc2c(c1)ncc1[nH]cnc12.c1ccccc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccccc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccccc1 | HBr.B | null | null | null | CCCCc1nc2cnc3cc(-c4ccc(OC)cc4OC)ccc3c2n1CC(C)C.CCCCc1nc2cnc3cc(Br)ccc3c2n1CC(C)C.COc1ccc(B(O)O)c(OC)c1>>CCCCc1nc2c(N)nc3cc(-c4ccc(OC)cc4OC)ccc3c2n1CC(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-182ec36ce0ca4c7dba7b593a28732964 | CCCCc1nc2c(N)nc3cc(Br)ccc3c2n1CC(C)C.CCCOc1ccc(B(O)O)cc1>>CCCCc1nc2c(N)nc3cc(-c4ccc(OCCC)cc4)ccc3c2n1CC(C)C | BrC=1C=CC=2C3=C(C(=NC2C1)N)N=C(N3CC(C)C)CCCC.C(CC)OC1=CC=C(C=C1)B(O)O>>C(CCC)C=1N(C2=C(C(=NC=3C=C(C=CC23)C2=CC=C(C=C2)OCCC)N)N1)CC(C)C | Br[c:13]1[cH:12][c:11]2[n:10][c:8]([NH2:9])[c:7]3[n:6][c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[n:28]([CH2:29][CH:30]([CH3:31])[CH3:32])[c:27]3[c:26]2[cH:25][cH:24]1.OB(O)[c:14]1[cH:15][cH:16][c:17]([O:18][CH2:19][CH2:20][CH3:21])[cH:22][cH:23]1>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12]... | CCCCc1nc2c(N)nc3cc(Br)ccc3c2n1CC(C)C.CCCOc1ccc(B(O)O)cc1 | CCCCc1nc2c(N)nc3cc(-c4ccc(OCCC)cc4)ccc3c2n1CC(C)C | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 89ee2e97ba79660eddf3dfa788334e60a83082a3d4afa6ed050c5f1f85789150 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc3c(c2)ncc2nc[nH]c23)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[c:6](:[#7;a:7]):[c:8](:[#7;a:9]):[c:10]:2:[c:11]:[c:12]:1.O-B(-O)-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16]:[c:17]>>[#7;a:9]:[c:8]1:[c:10]2:[c:11]:[c:12]:[c;H0;D3;+0:1](-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16]:[c:17]):[c:2]:[c:3]:2:[#7;a:4]:[c:5]:[c:6]:1:[#7;a:7] | null | [] | null | null | null | null | 7-Bromo-2-butyl-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine and 4-propoxybenzeneboronic acid were coupled according to the general procedure described in Part J of Example 1. The product was recrystallized from isopropanol, collected by filtration, dissolved in CH2Cl2, and then precipitated with hexanes to afford 2-bu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)ncc1[nH]cnc12.c1ccccc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccccc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccccc1 | HBr.B | null | null | null | CCCCc1nc2c(N)nc3cc(Br)ccc3c2n1CC(C)C.CCCOc1ccc(B(O)O)cc1>>CCCCc1nc2c(N)nc3cc(-c4ccc(OCCC)cc4)ccc3c2n1CC(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c102d39a905743a7a2a47a58a5ea662c | CCCCc1nc2c(N)nc3cc(Br)ccc3c2n1CC(C)C.CCCOc1ccccc1B(O)O>>CCCCc1nc2c(N)nc3cc(-c4ccccc4OCCC)ccc3c2n1CC(C)C | BrC=1C=CC=2C3=C(C(=NC2C1)N)N=C(N3CC(C)C)CCCC.C(CC)OC1=C(C=CC=C1)B(O)O>>C(CCC)C=1N(C2=C(C(=NC=3C=C(C=CC23)C2=C(C=CC=C2)OCCC)N)N1)CC(C)C | Br[c:13]1[cH:12][c:11]2[n:10][c:8]([NH2:9])[c:7]3[n:6][c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[n:28]([CH2:29][CH:30]([CH3:31])[CH3:32])[c:27]3[c:26]2[cH:25][cH:24]1.OB(O)[c:14]1[cH:15][cH:16][cH:17][cH:18][c:19]1[O:20][CH2:21][CH2:22][CH3:23]>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c... | CCCCc1nc2c(N)nc3cc(Br)ccc3c2n1CC(C)C.CCCOc1ccccc1B(O)O | CCCCc1nc2c(N)nc3cc(-c4ccccc4OCCC)ccc3c2n1CC(C)C | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 89ee2e97ba79660eddf3dfa788334e60a83082a3d4afa6ed050c5f1f85789150 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc3c(c2)ncc2nc[nH]c23)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[c:6](:[#7;a:7]):[c:8](:[#7;a:9]):[c:10]:2:[c:11]:[c:12]:1.O-B(-O)-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16](-[#8:17]):[c:18]>>[#7;a:9]:[c:8]1:[c:10]2:[c:11]:[c:12]:[c;H0;D3;+0:1](-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16](-[#8:17]):[c:18]):[c:2]:[c:3]:2:[#7;a:4]:[c:5]:[c:6]:1:[... | null | [] | null | null | null | null | 7-Bromo-2-butyl-1-isobutyl-1 H-imidazo[4,5-c]quinolin-4-amine and 2-propoxybenzeneboronic acid were coupled according to the general procedure described in Part J of Example 1. The product was recrystallized from isopropanol, collected by filtration, dissolved in CH2Cl2, and then precipitated with hexanes to afford 2-b... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)ncc1[nH]cnc12.c1ccccc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccccc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccccc1 | HBr.B | null | null | null | CCCCc1nc2c(N)nc3cc(Br)ccc3c2n1CC(C)C.CCCOc1ccccc1B(O)O>>CCCCc1nc2c(N)nc3cc(-c4ccccc4OCCC)ccc3c2n1CC(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-df44df3856b445519b7fa8f4529264dd | CCCCc1nc2c(N)nc3cc(Br)ccc3c2n1CC(C)C.OB(O)/C=C/c1ccccc1>>CCCCc1nc2c(N)nc3cc(/C=C/c4ccccc4)ccc3c2n1CC(C)C | BrC=1C=CC=2C3=C(C(=NC2C1)N)N=C(N3CC(C)C)CCCC.C1(=CC=CC=C1)/C=C/B(O)O>>C(CCC)C=1N(C2=C(C(=NC=3C=C(C=CC23)\C=C\C2=CC=CC=C2)N)N1)CC(C)C | Br[c:13]1[cH:12][c:11]2[n:10][c:8]([NH2:9])[c:7]3[n:6][c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[n:26]([CH2:27][CH:28]([CH3:29])[CH3:30])[c:25]3[c:24]2[cH:23][cH:22]1.OB(O)/[CH:14]=[CH:15]/[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13](/[CH:14... | CCCCc1nc2c(N)nc3cc(Br)ccc3c2n1CC(C)C.OB(O)/C=C/c1ccccc1 | CCCCc1nc2c(N)nc3cc(/C=C/c4ccccc4)ccc3c2n1CC(C)C | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 31390bd58c61a8b3a63a0fcb56e173272a33417778faf6071248245ca26329ae | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | C(=C/c1ccc2c(c1)ncc1nc[nH]c12)\c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[c:6](:[#7;a:7]):[c:8](:[#7;a:9]):[c:10]:2:[c:11]:[c:12]:1.O-B(-O)/[CH;D2;+0:13]=[C:14]/[c:15](:[c:16]):[c:17]>>[#7;a:9]:[c:8]1:[c:10]2:[c:11]:[c:12]:[c;H0;D3;+0:1](/[CH;D2;+0:13]=[C:14]/[c:15](:[c:16]):[c:17]):[c:2]:[c:3]:2:[#7;a:4]:[c:5]:[c:6]:1:[#7;a:7] | null | [] | null | null | null | null | 7-Bromo-2-butyl-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine and trans-2-phenylvinylboronic acid were coupled according to the general procedure described in Part J of Example 1. Recrystallization from toluene followed by chromatography on silica gel (8% methanol in CH2Cl2) afforded 2-butyl-1-isobutyl-7-[(E)-2-phenylet... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccccc1 | HBr.B | null | null | null | CCCCc1nc2c(N)nc3cc(Br)ccc3c2n1CC(C)C.OB(O)/C=C/c1ccccc1>>CCCCc1nc2c(N)nc3cc(/C=C/c4ccccc4)ccc3c2n1CC(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a10c8fa6f2f44d2892a4bdf1b6af3582 | CCCCc1nc2c(N)nc3cc(/C=C/c4ccccc4)ccc3c2n1CC(C)C>>CCCCc1nc2c(N)nc3cc(CCc4ccccc4)ccc3c2n1CC(C)C | C(CCC)C=1N(C2=C(C(=NC=3C=C(C=CC23)\C=C\C2=CC=CC=C2)N)N1)CC(C)C>>C(CCC)C=1N(C2=C(C(=NC=3C=C(C=CC23)CCC2=CC=CC=C2)N)N1)CC(C)C | [CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13](/[CH:14]=[CH:15]/[c:16]4[cH:17][cH:18][cH:19][cH:20][cH:21]4)[cH:22][cH:23][c:24]3[c:25]2[n:26]1[CH2:27][CH:28]([CH3:29])[CH3:30]>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13]([CH2:14][CH2:15][... | CCCCc1nc2c(N)nc3cc(/C=C/c4ccccc4)ccc3c2n1CC(C)C | CCCCc1nc2c(N)nc3cc(CCc4ccccc4)ccc3c2n1CC(C)C | null | [Pd] | null | Reduction | Hydrogenation (double to single) | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccc(CCc2ccc3c(c2)ncc2nc[nH]c23)cc1 | [#7;a:1]:[c:2]:[c:3]:[c:4](/[CH;D2;+0:5]=[CH;D2;+0:6]/[c:7](:[c:8]):[c:9]):[c:10]>>[#7;a:1]:[c:2]:[c:3]:[c:4](-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9]):[c:10] | 26.6 | [{"value": 26.6, "product": "C(CCC)C=1N(C2=C(C(=NC=3C=C(C=CC23)CCC2=CC=CC=C2)N)N1)CC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Butyl-1-isobutyl-7-[(E)-2-phenylethenyl]-1H-imidazo[4,5-c]quinolin-4-amine (562 mg, 1.41 mmol) was hydrogenated in a Parr bottle over palladium on carbon (10%) until the starting material was consumed as judged by high performance liquid chromatography (HPLC) and thin layer chromatography (TLC) analyses. Purification... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2c(c1)ncc1[nH]cnc12.c1ccccc1 | null | [Pd] | null | null | CCCCc1nc2c(N)nc3cc(/C=C/c4ccccc4)ccc3c2n1CC(C)C>[Pd]>CCCCc1nc2c(N)nc3cc(CCc4ccccc4)ccc3c2n1CC(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dbeb3e2c5d2e43e88e3b4fdfc8b56049 | CC(C)CNc1c(N)cnc2cc(Br)ccc12.CCOCC(=O)Cl>>CCOCc1nc2cnc3cc(Br)ccc3c2n1CC(C)C | BrC1=CC=C2C(=C(C=NC2=C1)N)NCC(C)C.C(C)OCC(=O)Cl>>BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CC(C)C)COCC | [NH2:6][c:7]1[cH:8][n:9][c:10]2[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]2[c:17]1[NH:18][CH2:19][CH:20]([CH3:21])[CH3:22].O=[C:5](Cl)[CH2:4][O:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]3[c:17]2[n:18]1[CH2:19][CH:20]([CH3:21])[CH3:22] | CC(C)CNc1c(N)cnc2cc(Br)ccc12.CCOCC(=O)Cl | CCOCc1nc2cnc3cc(Br)ccc3c2n1CC(C)C | null | null | N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 101a087a520f159c722ba3d78ed38f5c3c1cf154206e5edbeb1e6397c929560f | 56ef83dfadec35a1cf1db968b807e178cc4924ce15bf36d774883783cef0f450 | c1ccc2c(c1)ncc1nc[nH]c12 | Cl-[C;H0;D3;+0:1](=O)-[C:2]-[#8:3].[C:4]-[C:5]-[NH;D2;+0:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1-[NH2;D1;+0:13]>>[#8:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:13]:[c:12]2:[c:11]:[#7;a:10]:[c:9]:[c:8]:[c:7]:2:[n;H0;D3;+0:6]:1-[C:5]-[C:4] | 41.1 | [{"value": 41.1, "product": "BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CC(C)C)COCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3.5 | HOUR | A solution of 7-bromo—N4-isobutylquinoline-3,4-diamine (85 g, prepared according to Part F of Example 1) in anhydrous pyridine (413 mL) was immersed in an ice bath, and ethoxyacetyl chloride (36.9 g, 300 mmol) was added. The reaction was allowed to warm to room temperature and was then heated in an oil bath held at 85°... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine.Secondary amine | null | c1ccc2ncccc2c1 | c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12 | HCl | N1=CC=CC=C1 | null | 3.5 | CC(C)CNc1c(N)cnc2cc(Br)ccc12.CCOCC(=O)Cl>N1=CC=CC=C1>CCOCc1nc2cnc3cc(Br)ccc3c2n1CC(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cf064ee4162445c1a8b080a1ce1d6cbd | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CC(C)C.OB(O)c1ccsc1>>CCOCc1nc2c(N)nc3cc(-c4ccsc4)ccc3c2n1CC(C)C | BrC=1C=CC=2C3=C(C(=NC2C1)N)N=C(N3CC(C)C)COCC.S1C=C(C=C1)B(O)O>>C(C)OCC=1N(C2=C(C(=NC=3C=C(C=CC23)C2=CSC=C2)N)N1)CC(C)C | Br[c:13]1[cH:12][c:11]2[n:10][c:8]([NH2:9])[c:7]3[n:6][c:5]([CH2:4][O:3][CH2:2][CH3:1])[n:23]([CH2:24][CH:25]([CH3:26])[CH3:27])[c:22]3[c:21]2[cH:20][cH:19]1.OB(O)[c:14]1[cH:15][cH:16][s:17][cH:18]1>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13](-[c:14]4[cH:15][cH:16][s:17][cH:18]4... | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CC(C)C.OB(O)c1ccsc1 | CCOCc1nc2c(N)nc3cc(-c4ccsc4)ccc3c2n1CC(C)C | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 71675559eb4d0d484707d6905401f948ae6ef7d05b7d29e48ea037255a256d18 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1nc2cnc3cc(-c4ccsc4)ccc3c2[nH]1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[c:6](:[#7;a:7]):[c:8](:[#7;a:9]):[c:10]:2:[c:11]:[c:12]:1.O-B(-O)-[c;H0;D3;+0:13]1:[c:14]:[c:15]:[#16;a:16]:[c:17]:1>>[#7;a:9]:[c:8]1:[c:10]2:[c:11]:[c:12]:[c;H0;D3;+0:1](-[c;H0;D3;+0:13]3:[c:14]:[c:15]:[#16;a:16]:[c:17]:3):[c:2]:[c:3]:2:[#7;a:4]:[c:5]:[c:6]:1:[#7;a:7] | null | [] | null | null | null | null | 7-Bromo-2-ethoxymethyl-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine and thiophene-3-boronic acid were coupled according to the general procedure described in Part J of Example 1. Recrystallization from isopropanol followed by purification on silica gel (5% methanol in CH2Cl2 to 7% methanol in CH2Cl2 gradient) afforded ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)ncc1[nH]cnc12.c1ccsc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccsc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccsc1 | HBr.B | null | null | null | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CC(C)C.OB(O)c1ccsc1>>CCOCc1nc2c(N)nc3cc(-c4ccsc4)ccc3c2n1CC(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-90677ea3c633433eb22e37de2541dc36 | CC1(C)OC(=O)CC(=O)O1.Nc1cccc(-c2ccccc2)c1>>CC1(C)OC(=O)C(=CNc2cccc(-c3ccccc3)c2)C(=O)O1 | C(OCC)(OCC)OCC.CC1(OC(=O)CC(=O)O1)C.C1(=CC(=CC=C1)N)C1=CC=CC=C1>>C1(=CC(=CC=C1)NC=C1C(OC(OC1=O)(C)C)=O)C1=CC=CC=C1 | [CH3:1][C:2]1([CH3:3])[O:4][C:5](=[O:6])[CH2:7][C:22](=[O:23])[O:24]1.[NH2:9][c:10]1[cH:11][cH:12][cH:13][c:14](-[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[cH:21]1>>[CH3:1][C:2]1([CH3:3])[O:4][C:5](=[O:6])[C:7](=[CH:8][NH:9][c:10]2[cH:11][cH:12][cH:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[cH:21]2)[C:22... | CC1(C)OC(=O)CC(=O)O1.Nc1cccc(-c2ccccc2)c1 | CC1(C)OC(=O)C(=CNc2cccc(-c3ccccc3)c2)C(=O)O1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 16f6e689ff4988a3075463cf8c372a4929ef73d83eb11dd6443a2ba775713df7 | cb45d3f2664ea1c07edca6192a95c91d6c98f4c61196cc5a896d41447e7a94b5 | O=C1OCOC(=O)C1=CNc1cccc(-c2ccccc2)c1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[#8:7]-[C:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[CH2;D2;+0:12]-1>>[O;D1;H0:5]=[C:6]1-[#8:7]-[C:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[C;H0;D3;+0:12]-1=[C:13]-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 95.5 | [{"value": 95.5, "product": "C1(=CC(=CC=C1)NC=C1C(OC(OC1=O)(C)C)=O)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Triethyl orthoformate (148 g, 1.00 mol), Meldrum's acid (137 g, 0.95 mol), and biphenyl-3-ylamine (155 g, 0.916 mol) were combined and treated according to the general procedure described in Part A of Example 1 to obtain 283 g of 5-(biphenyl-3-ylaminomethylene)-2,2-dimethyl-[1,3]dioxane-4,6-dione as a yellow solid.
Con... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Primary amine | Enamine | C1COCOC1 | C1COCOC1 | C1COCOC1.c1ccccc1.c1ccccc1 | Other | null | null | null | CC1(C)OC(=O)CC(=O)O1.Nc1cccc(-c2ccccc2)c1>>CC1(C)OC(=O)C(=CNc2cccc(-c3ccccc3)c2)C(=O)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0c1767eb462a4ef8a4aafe3f59af607c | CC1(C)OC(=O)C(=CNc2cccc(-c3ccccc3)c2)C(=O)O1>>Oc1ccnc2cc(-c3ccccc3)ccc12 | C1(=CC(=CC=C1)NC=C1C(OC(OC1=O)(C)C)=O)C1=CC=CC=C1>>C1(=CC=CC=C1)C1=CC=C2C(=CC=NC2=C1)O | CC1(C)OC(=O)[C:3](=[CH:4][NH:5][c:6]2[cH:7][c:8](-[c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[cH:15][cH:16][cH:17]2)[C:2](=[O:1])O1>>[OH:1][c:2]1[cH:3][cH:4][n:5][c:6]2[cH:7][c:8](-[c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[cH:15][cH:16][c:17]12 | CC1(C)OC(=O)C(=CNc2cccc(-c3ccccc3)c2)C(=O)O1 | Oc1ccnc2cc(-c3ccccc3)ccc12 | null | null | C1=CC=C(C=C1)C2=CC=CC=C2.C1=CC=C(C=C1)OC2=CC=CC=C2 | Reduction | OtherReaction | 60da20daff3794d62e19d3191423fbc1080fe07b8a447f857ff8933cfafabe89 | 61086c5a1f033ee6da72542244d080a3c3d1d71db445f7bf1dc4b7c5fe1fe33e | c1ccc(-c2ccc3cccnc3c2)cc1 | C-C1(-C)-O-C(=O)-[C;H0;D3;+0:1](=[CH;D2;+0:2]-[NH;D2;+0:3]-[c:4](:[c:5]):[cH;D2;+0:6]:[c:7]:[c:8])-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-O-1>>[OH;D1;+0:10]-[c;H0;D3;+0:9]1:[cH;D2;+0:1]:[cH;D2;+0:2]:[n;H0;D2;+0:3]:[c:4](:[c:5]):[c;H0;D3;+0:6]:1:[c:7]:[c:8] | 96.7 | [{"value": 96.7, "product": "C1(=CC=CC=C1)C1=CC=C2C(=CC=NC2=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 90 | MINUTE | 5-(Biphenyl-3-ylaminomethylene)-2,2-dimethyl-[1,3]dioxane-4,6-dione (160.2 g, 496 mmol) was dissolved in 800 mL of DOWTHERM A heat transfer fluid at 100° C. and added over 40 min by way of a cannula line to 1.3 L of preheated DOWTHERM A heat transfer fluid to 215° C. After complete addition, the reaction was held at 21... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ester.Ester | Aromatic alcohol | C1COCOC1.c1ccccc1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccccc1 | HO- | C1=CC=C(C=C1)C2=CC=CC=C2.C1=CC=C(C=C1)OC2=CC=CC=C2 | 100 | 1.5 | CC1(C)OC(=O)C(=CNc2cccc(-c3ccccc3)c2)C(=O)O1>C1=CC=C(C=C1)C2=CC=CC=C2.C1=CC=C(C=C1)OC2=CC=CC=C2>Oc1ccnc2cc(-c3ccccc3)ccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e52aec0cac81483fa1aff8a997e54a25 | O=[N+]([O-])O.Oc1ccnc2cc(-c3ccccc3)ccc12>>O=[N+]([O-])c1cnc2cc(-c3ccccc3)ccc2c1O | C1(=CC=CC=C1)C1=CC=C2C(=CC=NC2=C1)O.[N+](=O)(O)[O-]>>[N+](=O)([O-])C=1C=NC2=CC(=CC=C2C1O)C1=CC=CC=C1 | O[N+:2](=[O:1])[O-:3].[cH:4]1[cH:5][n:6][c:7]2[cH:8][c:9](-[c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[cH:16][cH:17][c:18]2[c:19]1[OH:20]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][n:6][c:7]2[cH:8][c:9](-[c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[cH:16][cH:17][c:18]2[c:19]1[OH:20] | O=[N+]([O-])O.Oc1ccnc2cc(-c3ccccc3)ccc12 | O=[N+]([O-])c1cnc2cc(-c3ccccc3)ccc2c1O | null | null | C(CC)(=O)O | Functional Group Addition | Aromatic nitration with HNO3 | 93c60f395fb4f0e5be7b3c9f5aae0bbd322ad57344c0d8df26b336a54b906179 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccc(-c2ccc3cccnc3c2)cc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[O;D1;H1:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[cH;D2;+0:10]:1>>[O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[c;H0;D3;+0:10]1:[c:9]:[#7;a:8]:[c:7]:[c:6]:[c:5]:1-[O;D1;H1:4] | 81.4 | [{"value": 81.4, "product": "[N+](=O)([O-])C=1C=NC2=CC(=CC=C2C1O)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 129 | CELSIUS | 3 | HOUR | A stirred suspension of 7-phenylquinolin-4-ol (84.9 g, 384 mmol) in propionic acid (850 mL) was heated to 129° C. Nitric acid (70%, 45.0 g) was added dropwise over 25 min, during which the temperature dropped to 124° C. The reaction was stirred an additional 3 h at that temperature and then cooled to 5° C. on an ice ba... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccccc1 | HO- | C(CC)(=O)O | 129 | 3 | O=[N+]([O-])O.Oc1ccnc2cc(-c3ccccc3)ccc12>C(CC)(=O)O>O=[N+]([O-])c1cnc2cc(-c3ccccc3)ccc2c1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ba70021346be4b7b8d28ff373488a299 | O=P(Cl)(Cl)Cl.O=[N+]([O-])c1cnc2cc(-c3ccccc3)ccc2c1O>>O=[N+]([O-])c1cnc2cc(-c3ccccc3)ccc2c1Cl | P(=O)(Cl)(Cl)Cl.[N+](=O)([O-])C=1C=NC2=CC(=CC=C2C1O)C1=CC=CC=C1>>ClC1=C(C=NC2=CC(=CC=C12)C1=CC=CC=C1)[N+](=O)[O-] | O=P(Cl)(Cl)[Cl:20].O[c:19]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][n:6][c:7]2[cH:8][c:9](-[c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[cH:16][cH:17][c:18]21>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][n:6][c:7]2[cH:8][c:9](-[c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[cH:16][cH:17][c:18]2[c:19]1[Cl:20] | O=P(Cl)(Cl)Cl.O=[N+]([O-])c1cnc2cc(-c3ccccc3)ccc2c1O | O=[N+]([O-])c1cnc2cc(-c3ccccc3)ccc2c1Cl | null | null | CN(C=O)C | Functional Group Interconversion | Alcohol to chloride_POCl3_para | 27014e1419adc48e7dd5f2024d7f933bb85e42d4ec6c57e509da2884d477d689 | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1ccc(-c2ccc3cccnc3c2)cc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[c:3](:[c:4]):[c:5](:[c:6]):[#7;a:7]:[c:8]:[c:9]:1-[#7;+:10]>>[#7;+:10]-[c:9]1:[c:8]:[#7;a:7]:[c:5](:[c:6]):[c:3](:[c:4]):[c;H0;D3;+0:2]:1-[Cl;H0;D1;+0:1] | null | [] | null | null | 1.5 | HOUR | A solution of phosphorous oxychloride (3.1 g, 20 mmol) in anhydrous N,N-dimethylformamide (DMF, 14 mL) was added to a suspension of 3-nitro-7-phenylquinolin-4-ol (5.0 g, 18.8 mmol) in 80 mL of DMF over 3 min. The reaction was allowed to stir for 1.5 h and then poured into 250 mL crushed ice. The resulting precipitate w... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccccc1 | HCl | CN(C=O)C | null | 1.5 | O=P(Cl)(Cl)Cl.O=[N+]([O-])c1cnc2cc(-c3ccccc3)ccc2c1O>CN(C=O)C>O=[N+]([O-])c1cnc2cc(-c3ccccc3)ccc2c1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8075df8866694ec781accd5f264a85a4 | CSCCCN.O=[N+]([O-])c1cnc2cc(-c3ccccc3)ccc2c1Cl>>CSCCCNc1c([N+](=O)[O-])cnc2cc(-c3ccccc3)ccc12 | ClC1=C(C=NC2=CC(=CC=C12)C1=CC=CC=C1)[N+](=O)[O-].CSCCCN>>CSCCCNC1=C(C=NC2=CC(=CC=C12)C1=CC=CC=C1)[N+](=O)[O-] | [CH3:1][S:2][CH2:3][CH2:4][CH2:5][NH2:6].Cl[c:7]1[c:8]([N+:9](=[O:10])[O-:11])[cH:12][n:13][c:14]2[cH:15][c:16](-[c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[cH:23][cH:24][c:25]12>>[CH3:1][S:2][CH2:3][CH2:4][CH2:5][NH:6][c:7]1[c:8]([N+:9](=[O:10])[O-:11])[cH:12][n:13][c:14]2[cH:15][c:16](-[c:17]3[cH:18][cH:19][cH:20][c... | CSCCCN.O=[N+]([O-])c1cnc2cc(-c3ccccc3)ccc2c1Cl | CSCCCNc1c([N+](=O)[O-])cnc2cc(-c3ccccc3)ccc12 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 45e8470a78418ade39424f40732aa5ecf6717a7e5d47830a67429c5970ebd551 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(-c2ccc3cccnc3c2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]:[c:8]:1-[#7;+:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[#7;+:9]-[c:8]1:[c:7]:[#7;a:6]:[c:4](:[c:5]):[c:2](:[c:3]):[c;H0;D3;+0:1]:1-[NH;D2;+0:12]-[C:11]-[C:10] | 93.3 | [{"value": 93.3, "product": "CSCCCNC1=C(C=NC2=CC(=CC=C12)C1=CC=CC=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4—Chloro-3-nitro-7-phenylquinoline (5.3 g, 18.8 mmol) and 3-methylsulfanyl-propylamine (2.17 g, 20.6 mmol) were combined and treated according to the general procedure described in Part E of Example 1. Recrystallization from isopropanol afforded 6.2 g of (3-methylsulfanylpropyl)-(3-nitro-7-phenylquinolin-4-yl)amine as ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccccc1 | HCl | null | null | null | CSCCCN.O=[N+]([O-])c1cnc2cc(-c3ccccc3)ccc2c1Cl>>CSCCCNc1c([N+](=O)[O-])cnc2cc(-c3ccccc3)ccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c0fe02b4047447469750fe6ff08d67db | CSCCCNc1c([N+](=O)[O-])cnc2cc(-c3ccccc3)ccc12>>CSCCCNc1c(N)cnc2cc(-c3ccccc3)ccc12 | CSCCCNC1=C(C=NC2=CC(=CC=C12)C1=CC=CC=C1)[N+](=O)[O-]>>CSCCCNC1=C(C=NC2=CC(=CC=C12)C1=CC=CC=C1)N | O=[N+:9]([O-])[c:8]1[c:7]([NH:6][CH2:5][CH2:4][CH2:3][S:2][CH3:1])[c:23]2[c:12]([n:11][cH:10]1)[cH:13][c:14](-[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[cH:21][cH:22]2>>[CH3:1][S:2][CH2:3][CH2:4][CH2:5][NH:6][c:7]1[c:8]([NH2:9])[cH:10][n:11][c:12]2[cH:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[cH:21][cH:... | CSCCCNc1c([N+](=O)[O-])cnc2cc(-c3ccccc3)ccc12 | CSCCCNc1c(N)cnc2cc(-c3ccccc3)ccc12 | null | [Pt] | C1(=CC=CC=C1)C | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(-c2ccc3cccnc3c2)cc1 | 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] | 100 | [{"value": 100.0, "product": "CSCCCNC1=C(C=NC2=CC(=CC=C12)C1=CC=CC=C1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | (3-Methylsulfanylpropyl)-(3-nitro-7-phenylquinolin-4-yl)amine (3.0 g, 8.5 mmol) was hydrogenated in a Parr bottle over Pt/C (0.3 g of 5%) in 42 mL of toluene for 1 h. The reaction mixture was filtered through CELITE filter agent, washed with methanol (100 mL) and CHCl3 (50 mL), and then concentrated to afford 2.75 g of... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2ncccc2c1.c1ccccc1 | Other | [Pt].C1(=CC=CC=C1)C | null | null | CSCCCNc1c([N+](=O)[O-])cnc2cc(-c3ccccc3)ccc12>[Pt].C1(=CC=CC=C1)C>CSCCCNc1c(N)cnc2cc(-c3ccccc3)ccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-db8fbeb70dec4320954face4762c20da | CCCCC(OC)(OC)OC.CSCCCNc1c(N)cnc2cc(-c3ccccc3)ccc12>>CCCCc1nc2cnc3cc(-c4ccccc4)ccc3c2n1CCCSC | CSCCCNC1=C(C=NC2=CC(=CC=C12)C1=CC=CC=C1)N.C(CCCC)(OC)(OC)OC.Cl.N1=CC=CC=C1>>C(CCC)C=1N(C2=C(C=NC=3C=C(C=CC23)C2=CC=CC=C2)N1)CCCSC | CO[C:5](OC)(OC)[CH2:4][CH2:3][CH2:2][CH3:1].[NH2:6][c:7]1[cH:8][n:9][c:10]2[cH:11][c:12](-[c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19][cH:20][c:21]2[c:22]1[NH:23][CH2:24][CH2:25][CH2:26][S:27][CH3:28]>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:9][c:10]3[cH:11][c:12](-[c:13]4[cH:14][cH:15][cH:16][cH:1... | CCCCC(OC)(OC)OC.CSCCCNc1c(N)cnc2cc(-c3ccccc3)ccc12 | CCCCc1nc2cnc3cc(-c4ccccc4)ccc3c2n1CCCSC | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 8d87c769e65778c9400c7f523e0409ecf0ffad86543cd9fdd6ef4b239323db96 | a60e703c3cf5c0d933aa031358d338c45d96ec82dec3fc2d9f5dce06b9dcc651 | c1ccc(-c2ccc3c(c2)ncc2nc[nH]c23)cc1 | C-O-[C;H0;D4;+0:1](-O-C)(-O-C)-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1-[NH2;D1;+0:13]>>[C:4]-[C:5]-[n;H0;D3;+0:6]1:[c:7]2:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:2:[n;H0;D2;+0:13]:[c;H0;D3;+0:1]:1-[C:2]-[C:3] | 90.7 | [{"value": 90.7, "product": "C(CCC)C=1N(C2=C(C=NC=3C=C(C=CC23)C2=CC=CC=C2)N1)CCCSC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | N4-(3-Methylsulfanylpropyl)-7-phenylquinoline-3,4-diamine (2.75 g, 8.49 mmol), trimethyl orthovalerate (1.7 g, 10 mmol), and pyridine hydrochloride (0.3 g) were dissolved in toluene (28 mL) and heated to reflux for 1.5 h, collecting the volatiles in a Dean—Stark trap. Upon cooling to room temperature, the solvent was r... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Primary amine.Secondary amine | null | c1ccc2ncccc2c1 | c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccccc1 | HO- | C1(=CC=CC=C1)C | null | 1 | CCCCC(OC)(OC)OC.CSCCCNc1c(N)cnc2cc(-c3ccccc3)ccc12>C1(=CC=CC=C1)C>CCCCc1nc2cnc3cc(-c4ccccc4)ccc3c2n1CCCSC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ed8f627f3e2042acae8a94dcfcac827a | BrBr.CC(C)Cn1cnc2c(N)nc3ccccc3c21>>CC(C)Cn1cnc2c(N)nc3ccc(Br)cc3c21 | C(C(C)C)N1C=NC=2C(=NC=3C=CC=CC3C21)N.BrBr>>BrC1=CC=2C3=C(C(=NC2C=C1)N)N=CN3CC(C)C | Br[Br:16].[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]([NH2:10])[n:11][c:12]3[cH:13][cH:14][cH:15][cH:17][c:18]3[c:19]12>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]([NH2:10])[n:11][c:12]3[cH:13][cH:14][c:15]([Br:16])[cH:17][c:18]3[c:19]12 | BrBr.CC(C)Cn1cnc2c(N)nc3ccccc3c21 | CC(C)Cn1cnc2c(N)nc3ccc(Br)cc3c21 | null | null | C(C)(=O)O | Functional Group Interconversion | Bromination | 203112cf446e25794477b3f4b62b35c5de4ca920eba5ece53260bfccbd7b9ebb | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc2c(c1)ncc1nc[nH]c12 | Br-[Br;H0;D1;+0:1].[#7;a:2]:[c:3]1:[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]:1:[c:9]:[#7;a:10]>>[#7;a:2]:[c:3]1:[c:4]:[c:5]:[c;H0;D3;+0:6](-[Br;H0;D1;+0:1]):[c:7]:[c:8]:1:[c:9]:[#7;a:10] | 25.6 | [{"value": 25.6, "product": "BrC1=CC=2C3=C(C(=NC2C=C1)N)N=CN3CC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a solution of 1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine (10.0 g, 41.6 mmol) in acetic acid (150 mL) was added Br2 (10.0 g, 62.6 mmol), and after 24 h, the resulting solid was collected by filtration and washed with H2O. The orange solid was suspended in a saturated aqueous solution of NaHSO3, after which it was a... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1nc2ccccc2c2[nH]cnc12 | c1ccc2ncc3nc[nH]c3c2c1 | c1ccc2ncc3nc[nH]c3c2c1 | HBr | C(C)(=O)O | null | 24 | BrBr.CC(C)Cn1cnc2c(N)nc3ccccc3c21>C(C)(=O)O>CC(C)Cn1cnc2c(N)nc3ccc(Br)cc3c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6fe7ec3643804528b4183e666763a9a5 | CC(C)(C)c1ccc(B(O)O)cc1.CC(C)Cn1cnc2c(N)nc3ccc(Br)cc3c21>>CC(C)Cn1cnc2c(N)nc3ccc(-c4ccc(C(C)(C)C)cc4)cc3c21 | BrC1=CC=2C3=C(C(=NC2C=C1)N)N=CN3CC(C)C.C(C)(C)(C)C1=CC=C(C=C1)B(O)O>>C(C)(C)(C)C1=CC=C(C=C1)C1=CC=2C3=C(C(=NC2C=C1)N)N=CN3CC(C)C | OB(O)[c:16]1[cH:17][cH:18][c:19]([C:20]([CH3:21])([CH3:22])[CH3:23])[cH:24][cH:25]1.Br[c:15]1[cH:14][cH:13][c:12]2[n:11][c:9]([NH2:10])[c:8]3[n:7][cH:6][n:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[c:28]3[c:27]2[cH:26]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]([NH2:10])[n:11][c:12]3[cH:13][cH:14][c:15](-[c:16]... | CC(C)(C)c1ccc(B(O)O)cc1.CC(C)Cn1cnc2c(N)nc3ccc(Br)cc3c21 | CC(C)Cn1cnc2c(N)nc3ccc(-c4ccc(C(C)(C)C)cc4)cc3c21 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | d7a5947e9b277585517ecdc572044d33fd140be4e78d7cb7b0c07b7ea0ac1fa0 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc3ncc4nc[nH]c4c3c2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6](:[c:7]:1):[c:8]:[#7;a:9].O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[#7;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[c:7]:[c:6]:1:[c:8]:[#7;a:9] | null | [] | null | null | null | null | 8-Bromo-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine and 4-tert-butylbenzeneboronic acid were coupled according to the general procedure described in Part J of Example 1. Recrystallization from isopropanol followed by chromatography on silica gel (7% methanol in CH2Cl2) afforded 8-(4-tert-butylphenyl)-1-isobutyl-1H-imi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2ncc3[nH]cnc3c2c1 | c1ccc2ncc3nc[nH]c3c2c1.c1ccccc1 | c1ccc2ncc3nc[nH]c3c2c1.c1ccccc1 | HBr.B | null | null | null | CC(C)(C)c1ccc(B(O)O)cc1.CC(C)Cn1cnc2c(N)nc3ccc(Br)cc3c21>>CC(C)Cn1cnc2c(N)nc3ccc(-c4ccc(C(C)(C)C)cc4)cc3c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b5404f3d81c74fca9c293d91f37982f0 | CC(C)Cn1cnc2c(N)nc3ccc(Br)cc3c21.OB(O)c1ccsc1>>CC(C)Cn1cnc2c(N)nc3ccc(-c4ccsc4)cc3c21 | BrC1=CC=2C3=C(C(=NC2C=C1)N)N=CN3CC(C)C.S1C=C(C=C1)B(O)O>>C(C(C)C)N1C=NC=2C(=NC=3C=CC(=CC3C21)C2=CSC=C2)N | Br[c:15]1[cH:14][cH:13][c:12]2[n:11][c:9]([NH2:10])[c:8]3[n:7][cH:6][n:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[c:23]3[c:22]2[cH:21]1.OB(O)[c:16]1[cH:17][cH:18][s:19][cH:20]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]([NH2:10])[n:11][c:12]3[cH:13][cH:14][c:15](-[c:16]4[cH:17][cH:18][s:19][cH:20]4)[cH:21][c:22]... | CC(C)Cn1cnc2c(N)nc3ccc(Br)cc3c21.OB(O)c1ccsc1 | CC(C)Cn1cnc2c(N)nc3ccc(-c4ccsc4)cc3c21 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 0e414bfed961d165ada2a874b7e33ecaa27275bfea10ab6af1b945af426022ad | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1nc2cnc3ccc(-c4ccsc4)cc3c2[nH]1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6](:[c:7]:1):[c:8]:[#7;a:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[c:12]:[#16;a:13]:[c:14]:1>>[#7;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10]2:[c:11]:[c:12]:[#16;a:13]:[c:14]:2):[c:7]:[c:6]:1:[c:8]:[#7;a:9] | null | [] | null | null | null | null | 8-Bromo-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine and thiophene-3-boronic acid were coupled according to the general procedure described in Part J of Example 1. Recrystallization from isopropanol followed by chromatography on silica gel (7% methanol in CH2Cl2) afforded 1-isobutyl-8-(thiophen-3-yl)-1H-imidazo[4,5-c]q... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2ncc3[nH]cnc3c2c1.c1ccsc1 | c1ccc2ncc3nc[nH]c3c2c1.c1ccsc1 | c1ccc2ncc3nc[nH]c3c2c1.c1ccsc1 | HBr.B | null | null | null | CC(C)Cn1cnc2c(N)nc3ccc(Br)cc3c21.OB(O)c1ccsc1>>CC(C)Cn1cnc2c(N)nc3ccc(-c4ccsc4)cc3c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5f0e7f0c7f184036b62819e4b30b2546 | CC(C)Cn1cnc2c(N)nc3ccc(Br)cc3c21.COc1ccc(B(O)O)c(OC)c1>>COc1ccc(-c2ccc3nc(N)c4ncn(CC(C)C)c4c3c2)c(OC)c1 | BrC1=CC=2C3=C(C(=NC2C=C1)N)N=CN3CC(C)C.COC1=C(C=CC(=C1)OC)B(O)O>>COC1=C(C=CC(=C1)OC)C1=CC=2C3=C(C(=NC2C=C1)N)N=CN3CC(C)C | Br[c:7]1[cH:8][cH:9][c:10]2[n:11][c:12]([NH2:13])[c:14]3[n:15][cH:16][n:17]([CH2:18][CH:19]([CH3:20])[CH3:21])[c:22]3[c:23]2[cH:24]1.OB(O)[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:28][c:25]1[O:26][CH3:27]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]3[n:11][c:12]([NH2:13])[c:14]4[n:15][cH:16][n:17]([CH2... | CC(C)Cn1cnc2c(N)nc3ccc(Br)cc3c21.COc1ccc(B(O)O)c(OC)c1 | COc1ccc(-c2ccc3nc(N)c4ncn(CC(C)C)c4c3c2)c(OC)c1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 53cc9ca90227d2908951e3024c95de9c6c3fb7608365c04a68b45ee49e2f3f42 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc3ncc4nc[nH]c4c3c2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[c:4]:[#7;a:5]):[c:6](:[#7;a:7]):[c:8]:[c:9]:1.O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13](-[#8:14]):[c:15]>>[#7;a:7]:[c:6]1:[c:8]:[c:9]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13](-[#8:14]):[c:15]):[c:2]:[c:3]:1:[c:4]:[#7;a:5] | null | [] | null | null | null | null | 8-Bromo-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine and 2,4-dimethoxybenzeneboronic acid were coupled according to the general procedure described in Part J of Example 1. Purification by chromatography on silica gel (7% methanol in CH2Cl2) afforded 8-(2,4-dimethoxyphenyl)-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2ncc3[nH]cnc3c2c1.c1ccccc1 | c1ccccc1.c1ccc2ncc3[nH]cnc3c2c1 | c1ccccc1.c1ccc2ncc3[nH]cnc3c2c1 | HBr.B | null | null | null | CC(C)Cn1cnc2c(N)nc3ccc(Br)cc3c21.COc1ccc(B(O)O)c(OC)c1>>COc1ccc(-c2ccc3nc(N)c4ncn(CC(C)C)c4c3c2)c(OC)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c043e8636e5b4027bb6bf5e022ac7a37 | CC(C)Cn1cnc2c(N)nc3ccc(Br)cc3c21.OB(O)c1cccnc1>>CC(C)Cn1cnc2c(N)nc3ccc(-c4cccnc4)cc3c21 | BrC1=CC=2C3=C(C(=NC2C=C1)N)N=CN3CC(C)C.N1=CC(=CC=C1)B(O)O>>C(C(C)C)N1C=NC=2C(=NC=3C=CC(=CC3C21)C=2C=NC=CC2)N | Br[c:15]1[cH:14][cH:13][c:12]2[n:11][c:9]([NH2:10])[c:8]3[n:7][cH:6][n:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[c:24]3[c:23]2[cH:22]1.OB(O)[c:16]1[cH:17][cH:18][cH:19][n:20][cH:21]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]([NH2:10])[n:11][c:12]3[cH:13][cH:14][c:15](-[c:16]4[cH:17][cH:18][cH:19][n:20][cH:21]4... | CC(C)Cn1cnc2c(N)nc3ccc(Br)cc3c21.OB(O)c1cccnc1 | CC(C)Cn1cnc2c(N)nc3ccc(-c4cccnc4)cc3c21 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 5d3693fe08abbbc8184547f1e504a72adf7c4cbfcff89e5476d430c2e1e9dea5 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1cncc(-c2ccc3ncc4nc[nH]c4c3c2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6](:[c:7]:1):[c:8]:[#7;a:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[c:12]:[c:13]:[#7;a:14]:[c:15]:1>>[#7;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10]2:[c:11]:[c:12]:[c:13]:[#7;a:14]:[c:15]:2):[c:7]:[c:6]:1:[c:8]:[#7;a:9] | null | [] | null | null | null | null | 8-Bromo-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine and pyridine-3-boronic acid were coupled according to the general procedure described in Part J of Example 1. Purification by chromatography on silica gel (7%–10% methanol in CH2Cl2 gradient) afforded 1-isobutyl-8-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine as a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2ncc3[nH]cnc3c2c1.c1ccncc1 | c1ccc2ncc3nc[nH]c3c2c1.c1ccncc1 | c1ccc2ncc3nc[nH]c3c2c1.c1ccncc1 | HBr.B | null | null | null | CC(C)Cn1cnc2c(N)nc3ccc(Br)cc3c21.OB(O)c1cccnc1>>CC(C)Cn1cnc2c(N)nc3ccc(-c4cccnc4)cc3c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ea48b66e88164bddafa0c996a8011a44 | CC(C)Cn1cnc2c(N)nc3ccc(Br)cc3c21.OB(O)c1ccccc1>>CC(C)Cn1cnc2c(N)nc3ccc(-c4ccccc4)cc3c21 | BrC1=CC=2C3=C(C(=NC2C=C1)N)N=CN3CC(C)C.C1(=CC=CC=C1)B(O)O>>C(C(C)C)N1C=NC=2C(=NC=3C=CC(=CC3C21)C2=CC=CC=C2)N | Br[c:15]1[cH:14][cH:13][c:12]2[n:11][c:9]([NH2:10])[c:8]3[n:7][cH:6][n:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[c:24]3[c:23]2[cH:22]1.OB(O)[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]([NH2:10])[n:11][c:12]3[cH:13][cH:14][c:15](-[c:16]4[cH:17][cH:18][cH:19][cH:20][cH:21... | CC(C)Cn1cnc2c(N)nc3ccc(Br)cc3c21.OB(O)c1ccccc1 | CC(C)Cn1cnc2c(N)nc3ccc(-c4ccccc4)cc3c21 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | d7a5947e9b277585517ecdc572044d33fd140be4e78d7cb7b0c07b7ea0ac1fa0 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc3ncc4nc[nH]c4c3c2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6](:[c:7]:1):[c:8]:[#7;a:9].O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[#7;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[c:7]:[c:6]:1:[c:8]:[#7;a:9] | null | [] | null | null | null | null | 8-Bromo-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine and benzeneboronic acid were coupled according to the general procedure described in Part J of Example 1. Recrystallization from isopropanol followed by recrystallization from methanol afforded 1-isobutyl-8-phenyl-1H-imidazo[4,5-c]quinolin-4-amine as a beige solid, m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2ncc3[nH]cnc3c2c1.c1ccccc1 | c1ccc2ncc3nc[nH]c3c2c1.c1ccccc1 | c1ccc2ncc3nc[nH]c3c2c1.c1ccccc1 | HBr.B | null | null | null | CC(C)Cn1cnc2c(N)nc3ccc(Br)cc3c21.OB(O)c1ccccc1>>CC(C)Cn1cnc2c(N)nc3ccc(-c4ccccc4)cc3c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-81344968fab24210b3c08586347dafa4 | CCc1nc2c(N)nc3ccc(Br)cc3c2n1CC(C)C.OB(O)c1ccccc1>>CCc1nc2c(N)nc3ccc(-c4ccccc4)cc3c2n1CC(C)C | BrC1=CC=2C3=C(C(=NC2C=C1)N)N=C(N3CC(C)C)CC.C1(=CC=CC=C1)B(O)O>>C(C)C=1N(C2=C(C(=NC=3C=CC(=CC23)C2=CC=CC=C2)N)N1)CC(C)C | Br[c:12]1[cH:11][cH:10][c:9]2[n:8][c:6]([NH2:7])[c:5]3[n:4][c:3]([CH2:2][CH3:1])[n:22]([CH2:23][CH:24]([CH3:25])[CH3:26])[c:21]3[c:20]2[cH:19]1.OB(O)[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]2[c:6]([NH2:7])[n:8][c:9]3[cH:10][cH:11][c:12](-[c:13]4[cH:14][cH:15][cH:16][cH:17][cH:18]4)[cH:... | CCc1nc2c(N)nc3ccc(Br)cc3c2n1CC(C)C.OB(O)c1ccccc1 | CCc1nc2c(N)nc3ccc(-c4ccccc4)cc3c2n1CC(C)C | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 53cc9ca90227d2908951e3024c95de9c6c3fb7608365c04a68b45ee49e2f3f42 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc3ncc4nc[nH]c4c3c2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6](:[c:7]:1):[c:8]:[#7;a:9].O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[#7;a:9]:[c:8]:[c:6]1:[c:7]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[c:2]:[c:3]:[c:4]:1:[#7;a:5] | null | [] | null | null | null | null | 8-Bromo-2-ethyl-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine and benzeneboronic acid were coupled according to the general procedure described in Part J of Example 1. Chromatography on silica gel (5%–7% methanol in CH2Cl2 gradient) afforded 2-ethyl-1-isobutyl-8-phenyl-1H-imidazo[4,5-c]quinolin-4-amine as a white solid,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2ncc3[nH]cnc3c2c1.c1ccccc1 | c1ccc2ncc3[nH]cnc3c2c1.c1ccccc1 | c1ccc2ncc3[nH]cnc3c2c1.c1ccccc1 | HBr.B | null | null | null | CCc1nc2c(N)nc3ccc(Br)cc3c2n1CC(C)C.OB(O)c1ccccc1>>CCc1nc2c(N)nc3ccc(-c4ccccc4)cc3c2n1CC(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b911d3355fd84051988e9ff9322156c6 | CCc1nc2c(N)nc3ccc(Br)cc3c2n1CC(C)C.OB(O)c1cccnc1>>CCc1nc2c(N)nc3ccc(-c4cccnc4)cc3c2n1CC(C)C | BrC1=CC=2C3=C(C(=NC2C=C1)N)N=C(N3CC(C)C)CC.N1=CC(=CC=C1)B(O)O>>C(C)C=1N(C2=C(C(=NC=3C=CC(=CC23)C=2C=NC=CC2)N)N1)CC(C)C | Br[c:12]1[cH:11][cH:10][c:9]2[n:8][c:6]([NH2:7])[c:5]3[n:4][c:3]([CH2:2][CH3:1])[n:22]([CH2:23][CH:24]([CH3:25])[CH3:26])[c:21]3[c:20]2[cH:19]1.OB(O)[c:13]1[cH:14][cH:15][cH:16][n:17][cH:18]1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]2[c:6]([NH2:7])[n:8][c:9]3[cH:10][cH:11][c:12](-[c:13]4[cH:14][cH:15][cH:16][n:17][cH:18]4)[cH:19... | CCc1nc2c(N)nc3ccc(Br)cc3c2n1CC(C)C.OB(O)c1cccnc1 | CCc1nc2c(N)nc3ccc(-c4cccnc4)cc3c2n1CC(C)C | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | bc9cd5af0d1465da413bcba1dea78360c9cd1c2208ec56a2c19fa0e80e6b9c1f | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1cncc(-c2ccc3ncc4nc[nH]c4c3c2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6](:[c:7]:1):[c:8]:[#7;a:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[c:12]:[c:13]:[#7;a:14]:[c:15]:1>>[#7;a:9]:[c:8]:[c:6]1:[c:7]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10]2:[c:11]:[c:12]:[c:13]:[#7;a:14]:[c:15]:2):[c:2]:[c:3]:[c:4]:1:[#7;a:5] | null | [] | null | null | null | null | 8-Bromo-2-ethyl-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine and pyridine-3-boronic acid were coupled according to the general procedure described in Part J of Example 1. Chromatography on silica gel (5%–7% methanol in CH2Cl2 gradient) followed by recrystallization from isopropanol afforded 2-ethyl-1-isobutyl-8-(pyridi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2ncc3[nH]cnc3c2c1.c1ccncc1 | c1ccc2ncc3[nH]cnc3c2c1.c1ccncc1 | c1ccc2ncc3[nH]cnc3c2c1.c1ccncc1 | HBr.B | null | null | null | CCc1nc2c(N)nc3ccc(Br)cc3c2n1CC(C)C.OB(O)c1cccnc1>>CCc1nc2c(N)nc3ccc(-c4cccnc4)cc3c2n1CC(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-42e4e7a533e14cb8940c0844c4da9573 | CCCCn1c(COCC)nc2c(N)nc3ccc(Br)cc3c21.OB(O)c1ccccc1>>CCCCn1c(COCC)nc2c(N)nc3ccc(-c4ccccc4)cc3c21 | BrC1=CC=2C3=C(C(=NC2C=C1)N)N=C(N3CCCC)COCC.C1(=CC=CC=C1)B(O)O>>C(CCC)N1C(=NC=2C(=NC=3C=CC(=CC3C21)C2=CC=CC=C2)N)COCC | Br[c:19]1[cH:18][cH:17][c:16]2[n:15][c:13]([NH2:14])[c:12]3[n:11][c:6]([CH2:7][O:8][CH2:9][CH3:10])[n:5]([CH2:4][CH2:3][CH2:2][CH3:1])[c:28]3[c:27]2[cH:26]1.OB(O)[c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[c:6]([CH2:7][O:8][CH2:9][CH3:10])[n:11][c:12]2[c:13]([NH2:14])[n:15][c:16]3[cH... | CCCCn1c(COCC)nc2c(N)nc3ccc(Br)cc3c21.OB(O)c1ccccc1 | CCCCn1c(COCC)nc2c(N)nc3ccc(-c4ccccc4)cc3c21 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | d7a5947e9b277585517ecdc572044d33fd140be4e78d7cb7b0c07b7ea0ac1fa0 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc3ncc4nc[nH]c4c3c2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6](:[c:7]:1):[c:8]:[#7;a:9].O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[#7;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[c:7]:[c:6]:1:[c:8]:[#7;a:9] | null | [] | null | null | null | null | 8-Bromo-1-butyl-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine and benzeneboronic acid were coupled according to the general procedure described in Part J of Example 1. Chromatography on silica gel (10% methanol in CH2Cl2) followed by recrystallization from isopropanol afforded 1-butyl-2-ethoxymethyl-8-phenyl-1H-imid... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2ncc3[nH]cnc3c2c1.c1ccccc1 | c1ccc2ncc3nc[nH]c3c2c1.c1ccccc1 | c1ccc2ncc3nc[nH]c3c2c1.c1ccccc1 | HBr.B | null | null | null | CCCCn1c(COCC)nc2c(N)nc3ccc(Br)cc3c21.OB(O)c1ccccc1>>CCCCn1c(COCC)nc2c(N)nc3ccc(-c4ccccc4)cc3c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c28838e1bbc145a798736594e16b04cc | CCCCn1c(COCC)nc2c(N)nc3ccc(Br)cc3c21.OB(O)c1cccnc1>>CCCCn1c(COCC)nc2c(N)nc3ccc(-c4cccnc4)cc3c21 | BrC1=CC=2C3=C(C(=NC2C=C1)N)N=C(N3CCCC)COCC.N1=CC(=CC=C1)B(O)O>>C(CCC)N1C(=NC=2C(=NC=3C=CC(=CC3C21)C=2C=NC=CC2)N)COCC | Br[c:19]1[cH:18][cH:17][c:16]2[n:15][c:13]([NH2:14])[c:12]3[n:11][c:6]([CH2:7][O:8][CH2:9][CH3:10])[n:5]([CH2:4][CH2:3][CH2:2][CH3:1])[c:28]3[c:27]2[cH:26]1.OB(O)[c:20]1[cH:21][cH:22][cH:23][n:24][cH:25]1>>[CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[c:6]([CH2:7][O:8][CH2:9][CH3:10])[n:11][c:12]2[c:13]([NH2:14])[n:15][c:16]3[cH:... | CCCCn1c(COCC)nc2c(N)nc3ccc(Br)cc3c21.OB(O)c1cccnc1 | CCCCn1c(COCC)nc2c(N)nc3ccc(-c4cccnc4)cc3c21 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 5d3693fe08abbbc8184547f1e504a72adf7c4cbfcff89e5476d430c2e1e9dea5 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1cncc(-c2ccc3ncc4nc[nH]c4c3c2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6](:[c:7]:1):[c:8]:[#7;a:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[c:12]:[c:13]:[#7;a:14]:[c:15]:1>>[#7;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10]2:[c:11]:[c:12]:[c:13]:[#7;a:14]:[c:15]:2):[c:7]:[c:6]:1:[c:8]:[#7;a:9] | null | [] | null | null | null | null | 8-Bromo-1-butyl-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine and pyridine-3-boronic acid were coupled according to the general procedure described in Part J of Example 1. Chromatography on silica gel (8%–10% methanol in CH2Cl2 gradient) followed by recrystallization from isopropanol (3×) and chromatography as above... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2ncc3[nH]cnc3c2c1.c1ccncc1 | c1ccc2ncc3nc[nH]c3c2c1.c1ccncc1 | c1ccc2ncc3nc[nH]c3c2c1.c1ccncc1 | HBr.B | null | null | null | CCCCn1c(COCC)nc2c(N)nc3ccc(Br)cc3c21.OB(O)c1cccnc1>>CCCCn1c(COCC)nc2c(N)nc3ccc(-c4cccnc4)cc3c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5d4c45ec99c44e3195ba265c9d851613 | CC(C)(C)[Si](C)(C)OCc1cncc(Br)c1.CC(C)OB(OC(C)C)OC(C)C.[Li][CH2]CCC.[NH4+]>>CC(C)(C)[Si](C)(C)OCc1cncc(B(O)O)c1.CC(C)(C)[Si](C)(C)OCc1cncc(Br)c1 | [Cl-].[NH4+].BrC=1C=NC=C(C1)CO[Si](C)(C)C(C)(C)C.B(OC(C)C)(OC(C)C)OC(C)C.C(CCC)[Li]>>BrC=1C=NC=C(C1)CO[Si](C)(C)C(C)(C)C.[Si](C)(C)(C(C)(C)C)OCC=1C=C(C=NC1)B(O)O | [CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][c:10]1[cH:11][n:12][cH:31][c:32]([Br:33])[cH:34]1.C([O:16][B:15]([O:17][CH:20]([CH3:21])[CH3:22])[O:26][CH:27]([CH3:19])[CH3:28])([CH3:24])[CH3:25].[Li][CH2:13][CH2:14][CH2:18][CH3:29].[NH4+:30]>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:... | CC(C)(C)[Si](C)(C)OCc1cncc(Br)c1.CC(C)OB(OC(C)C)OC(C)C.[Li][CH2]CCC.[NH4+] | CC(C)(C)[Si](C)(C)OCc1cncc(B(O)O)c1.CC(C)(C)[Si](C)(C)OCc1cncc(Br)c1 | null | null | C1CCOC1.O | Aromatic Heterocycle Formation | OtherReaction | 760ffe1126c708fb30f687132fd5f9d9d71261d64559658713a72c3632875204 | 05caca3ab5e3f1ac57dd8889f11d62a26dead3dbc27832571298c14785df3016 | c1ccncc1.c1ccncc1 | [#8:1]-[C:2]-[c;H0;D3;+0:3]1:[c:4]:[n;H0;D2;+0:5]:[cH;D2;+0:6]:[c:7](-[Br;D1;H0:8]):[cH;D2;+0:9]:1.[C;D1;H3:10]-[CH;D3;+0:11](-[C;D1;H3:12])-[O;H0;D2;+0:13]-[B;H0;D3;+0:14](-[O;H0;D2;+0:15]-C(-[CH3;D1;+0:16])-[CH3;D1;+0:17])-[O;H0;D2;+0:18]-[CH;D3;+0:19](-[CH3;D1;+0:20])-[CH3;D1;+0:21].[CH3;D1;+0:22]-[CH2;D2;+0:23]-[CH... | 143.4 | [{"value": 143.4, "product": "[Si](C)(C)(C(C)(C)C)OCC=1C=C(C=NC1)B(O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -20 | CELSIUS | 30 | MINUTE | 3-Bromo-5-(tert-butyldimethylsilanyloxymethyl)pyridine was prepared according to the published procedure (Zhang, N. et al, J. Med. Chem., 45, 2832–2840 (2002)). Under a nitrogen atmosphere, a solution of 3-bromo-5-(tert-butyldimethylsilanyloxymethyl)pyridine (28.70 g, 94.94 mmol) and triisopropyl borate (26.3 mL, 114 m... | 10.6084/m9.figshare.5104873.v1 | null | Alkyl lithium | Boronic acid.TMS ether protective group | c1ccncc1 | c1ccncc1.c1ccncc1 | c1ccncc1.c1ccncc1 | Li | C1CCOC1.O | -20 | 0.5 | CC(C)(C)[Si](C)(C)OCc1cncc(Br)c1.CC(C)OB(OC(C)C)OC(C)C.[Li][CH2]CCC.[NH4+]>C1CCOC1.O>CC(C)(C)[Si](C)(C)OCc1cncc(B(O)O)c1.CC(C)(C)[Si](C)(C)OCc1cncc(Br)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ce608b941e714b91967ecf915812fdb8 | CC(C)Cn1cnc2c(N)nc3ccc(C=Cc4ccccc4)cc3c21>>CC(C)Cn1cnc2c(N)nc3ccc(CCc4ccccc4)cc3c21 | CC(CN1C=NC=2C(=NC=3C=CC(=CC3C21)C=CC2=CC=CC=C2)N)C>>CC(CN1C=NC=2C(=NC=3C=CC(=CC3C21)CCC2=CC=CC=C2)N)C | [CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]([NH2:10])[n:11][c:12]3[cH:13][cH:14][c:15]([CH:16]=[CH:17][c:18]4[cH:19][cH:20][cH:21][cH:22][cH:23]4)[cH:24][c:25]3[c:26]12>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]([NH2:10])[n:11][c:12]3[cH:13][cH:14][c:15]([CH2:16][CH2:17][c:18]4[cH:19][cH:2... | CC(C)Cn1cnc2c(N)nc3ccc(C=Cc4ccccc4)cc3c21 | CC(C)Cn1cnc2c(N)nc3ccc(CCc4ccccc4)cc3c21 | null | [Pd] | C(C)O | Reduction | Hydrogenation (double to single) | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccc(CCc2ccc3ncc4nc[nH]c4c3c2)cc1 | [c:1]:[c:2](-[CH;D2;+0:3]=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7]):[c:8]>>[c:1]:[c:2](-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7]):[c:8] | 21.8 | [{"value": 21.8, "product": "CC(CN1C=NC=2C(=NC=3C=CC(=CC3C21)CCC2=CC=CC=C2)N)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 1-(2-methylpropyl)-8-styryl-1H-imidazo[4,5-c]quinolin-4-amine (1.37 g, 4.00 mmol) in ethanol (40 mL) was added to a Parr vessel charged with 10% palladium on carbon (137 mg). The reaction was placed under hydrogen pressure (40 psi, 2.8×105 Pa) for six days. The reaction mixture was filtered through a laye... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2ncc3nc[nH]c3c2c1.c1ccccc1 | null | [Pd].C(C)O | null | null | CC(C)Cn1cnc2c(N)nc3ccc(C=Cc4ccccc4)cc3c21>[Pd].C(C)O>CC(C)Cn1cnc2c(N)nc3ccc(CCc4ccccc4)cc3c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-264de42745e6441b818c0fd73a192dd5 | CC(C)(O)CN.O=[N+]([O-])c1cnc2cc(Br)ccc2c1Cl>>CC(C)(O)CNc1c([N+](=O)[O-])cnc2cc(Br)ccc12 | C(C)N(CC)CC.BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])Cl.NCC(C)(O)C>>BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])NCC(C)(O)C | [CH3:1][C:2]([CH3:3])([OH:4])[CH2:5][NH2:6].Cl[c:7]1[c:8]([N+:9](=[O:10])[O-:11])[cH:12][n:13][c:14]2[cH:15][c:16]([Br:17])[cH:18][cH:19][c:20]12>>[CH3:1][C:2]([CH3:3])([OH:4])[CH2:5][NH:6][c:7]1[c:8]([N+:9](=[O:10])[O-:11])[cH:12][n:13][c:14]2[cH:15][c:16]([Br:17])[cH:18][cH:19][c:20]12 | CC(C)(O)CN.O=[N+]([O-])c1cnc2cc(Br)ccc2c1Cl | CC(C)(O)CNc1c([N+](=O)[O-])cnc2cc(Br)ccc12 | null | null | ClCCl | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 45e8470a78418ade39424f40732aa5ecf6717a7e5d47830a67429c5970ebd551 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc2ncccc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]:[c:8]:1-[#7;+:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[#7;+:9]-[c:8]1:[c:7]:[#7;a:6]:[c:4](:[c:5]):[c:2](:[c:3]):[c;H0;D3;+0:1]:1-[NH;D2;+0:12]-[C:11]-[C:10] | 78.5 | [{"value": 78.5, "product": "BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])NCC(C)(O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 8 | HOUR | Triethylamine (17.35 mL, 124 mmol) was added to a solution of 7-bromo-4-chloro-3-nitroquinoline (29.84 g, 104 mmol) in dichloromethane (253 mL), and the reaction was cooled to 0° C. 1-Amino-2-methylpropan-2-ol (10.17 g, 114 mmol) was added dropwise, and then the reaction was allowed to warm to ambient temperature and s... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HCl | ClCCl | 0 | 8 | CC(C)(O)CN.O=[N+]([O-])c1cnc2cc(Br)ccc2c1Cl>ClCCl>CC(C)(O)CNc1c([N+](=O)[O-])cnc2cc(Br)ccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1a6beef3a19343c4ac3cbf90e4bc2e18 | CC(C)(O)CNc1c([N+](=O)[O-])cnc2cc(Br)ccc12>>CC(C)(O)CNc1c(N)cnc2cc(Br)ccc12 | BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])NCC(C)(O)C>>NC=1C=NC2=CC(=CC=C2C1NCC(C)(O)C)Br | O=[N+:9]([O-])[c:8]1[c:7]([NH:6][CH2:5][C:2]([CH3:1])([CH3:3])[OH:4])[c:18]2[c:12]([n:11][cH:10]1)[cH:13][c:14]([Br:15])[cH:16][cH:17]2>>[CH3:1][C:2]([CH3:3])([OH:4])[CH2:5][NH:6][c:7]1[c:8]([NH2:9])[cH:10][n:11][c:12]2[cH:13][c:14]([Br:15])[cH:16][cH:17][c:18]12 | CC(C)(O)CNc1c([N+](=O)[O-])cnc2cc(Br)ccc12 | CC(C)(O)CNc1c(N)cnc2cc(Br)ccc12 | null | [Pt] | C(C)#N | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2ncccc2c1 | 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] | 85.7 | [{"value": 85.7, "product": "NC=1C=NC2=CC(=CC=C2C1NCC(C)(O)C)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 1-(7-bromo-3-nitroquinolin-4-ylamino)-2-methylpropan-2-ol (27.78 g, 81.66 mmol) in acetonitrile (1.2 L) was added to a Parr vessel charged with 5% platinum on carbon (0.84 g), and the reaction was placed under hydrogen pressure (50 psi, 3.4×105 Pa) for two days. The reaction mixture was filtered through a... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2ncccc2c1 | Other | [Pt].C(C)#N | null | null | CC(C)(O)CNc1c([N+](=O)[O-])cnc2cc(Br)ccc12>[Pt].C(C)#N>CC(C)(O)CNc1c(N)cnc2cc(Br)ccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-408b6bd98e6c455a89225c1e8c5e9238 | CC(C)(O)CNc1c(N)cnc2cc(Br)ccc12.CCOCC(=O)Cl>>CCOCC(=O)Nc1cnc2cc(Br)ccc2c1NCC(C)(C)O | NC=1C=NC2=CC(=CC=C2C1NCC(C)(O)C)Br.C(C)OCC(=O)Cl>>BrC1=CC=C2C(=C(C=NC2=C1)NC(COCC)=O)NCC(C)(C)O | [NH2:7][c:8]1[cH:9][n:10][c:11]2[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]2[c:18]1[NH:19][CH2:20][C:21]([CH3:22])([CH3:23])[OH:24].Cl[C:5]([CH2:4][O:3][CH2:2][CH3:1])=[O:6]>>[CH3:1][CH2:2][O:3][CH2:4][C:5](=[O:6])[NH:7][c:8]1[cH:9][n:10][c:11]2[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]2[c:18]1[NH:19][CH2:20][C:21]([CH3... | CC(C)(O)CNc1c(N)cnc2cc(Br)ccc12.CCOCC(=O)Cl | CCOCC(=O)Nc1cnc2cc(Br)ccc2c1NCC(C)(C)O | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc2ncccc2c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]:[#7;a:9]:[c:10]>>[#8:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8]:[#7;a:9]:[c:10] | null | [] | null | null | 8 | HOUR | A solution of 1-(3-amino-7-bromoquinolin-4-ylamino)-2-methylpropan-2-ol (158.19 g, 0.510 mol) in dichloromethane (1.2 L) was cooled to 0° C. Ethoxyacetyl chloride (62.50 g, 0.510 mol) was added dropwise, and then the reaction was allowed to warm to ambient temperature and stirred overnight. A precipitate formed and was... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2ncccc2c1 | HCl | ClCCl | null | 8 | CC(C)(O)CNc1c(N)cnc2cc(Br)ccc12.CCOCC(=O)Cl>ClCCl>CCOCC(=O)Nc1cnc2cc(Br)ccc2c1NCC(C)(C)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2ad48777879c49898552a1d3c495787b | CCOCC(=O)Nc1cnc2cc(Br)ccc2c1NCC(C)(C)O>>CCOCc1nc2cnc3cc(Br)ccc3c2n1CC(C)(C)O | [OH-].[Na+].BrC1=CC=C2C(=C(C=NC2=C1)NC(COCC)=O)NCC(C)(C)O>>BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CC(C)(O)C)COCC | O=[C:5]([CH2:4][O:3][CH2:2][CH3:1])[NH:6][c:7]1[cH:8][n:9][c:10]2[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]2[c:17]1[NH:18][CH2:19][C:20]([CH3:21])([CH3:22])[OH:23]>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]3[c:17]2[n:18]1[CH2:19][C:20]([CH3:21])([CH3:22])[OH... | CCOCC(=O)Nc1cnc2cc(Br)ccc2c1NCC(C)(C)O | CCOCc1nc2cnc3cc(Br)ccc3c2n1CC(C)(C)O | null | null | O.C(C)O | Aromatic Heterocycle Formation | OtherReaction | a6a1d4e36f45189361154011b48477e6e08494aa3d520e5d656bee23ebaa3d72 | 71fdeda1d5481ba7466e825735d29b5ffca597c091e9548c43a80a0aea31b8a0 | c1ccc2c(c1)ncc1nc[nH]c12 | O=[C;H0;D3;+0:1](-[C:2]-[#8:3])-[NH;D2;+0:4]-[c:5]1:[c:6]:[#7;a:7]:[c:8]:[c:9]:[c:10]:1-[NH;D2;+0:11]-[C:12]-[C:13]>>[#8:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:4]:[c:5]2:[c:6]:[#7;a:7]:[c:8]:[c:9]:[c:10]:2:[n;H0;D3;+0:11]:1-[C:12]-[C:13] | 49.3 | [{"value": 49.3, "product": "BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CC(C)(O)C)COCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of sodium hydroxide (25 g, 0.625 mol) in water (205 mL) was added to a solution of N-[7-bromo-4-(2-hydroxy-2-methylpropylamino)quinolin-3-yl]-2-ethoxyacetamide (170.88 g, 0.431 mol) in ethanol (700 mL), and the reaction was heated at reflux under a nitrogen atmosphere for two hours. Upon cooling the reaction... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Secondary amine | null | c1ccc2ncccc2c1 | c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12 | HO- | O.C(C)O | null | null | CCOCC(=O)Nc1cnc2cc(Br)ccc2c1NCC(C)(C)O>O.C(C)O>CCOCc1nc2cnc3cc(Br)ccc3c2n1CC(C)(C)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-db1f569af9f74fb396843cd058260599 | CCI.CN(C)C=O.C[Si](C)(C)[N-][Si](C)(C)C.OCc1cncc(Br)c1>>CCOCc1cncc(Br)c1.OCc1cncc(Br)c1 | BrC=1C=C(C=NC1)CO.ICC.CN(C)C=O.C[Si](C)(C)[N-][Si](C)(C)C.[Na+]>>BrC=1C=C(C=NC1)CO.BrC=1C=NC=C(C1)COCC | I[CH2:2][CH3:1].[CH3:6][N:7]([CH:13]=[O:12])[CH3:17].C[Si]([N-][Si](C)(C)[CH3:20])([CH3:14])[CH3:18].[OH:3][CH2:4][c:5]1[cH:11][c:9]([Br:10])[cH:8][n:16][cH:15]1>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[cH:6][n:7][cH:8][c:9]([Br:10])[cH:11]1.[OH:12][CH2:13][c:14]1[cH:15][n:16][cH:17][c:18]([Br:19])[cH:20]1 | CCI.CN(C)C=O.C[Si](C)(C)[N-][Si](C)(C)C.OCc1cncc(Br)c1 | CCOCc1cncc(Br)c1.OCc1cncc(Br)c1 | null | null | C1CCOC1.[Cl-].[Na+].O | Aromatic Heterocycle Formation | OtherReaction | fc04c4ae40dd12bafa2c8a65fc824c07c7ff335d0d21f5e538d55613c2190bc4 | e808c4eb1c226ff0e8ce0911837bdf7c02e220c858f4a3b662b483795bf854c7 | c1ccncc1.c1ccncc1 | C-[Si](-[CH3;D1;+0:1])(-[CH3;D1;+0:2])-[N-]-[Si](-C)(-C)-[CH3;D1;+0:3].I-[CH2;D2;+0:4]-[C;D1;H3:5].[Br;D1;H0:6]-[c:7]1:[c:8]:[c;H0;D3;+0:9](-[C:10]-[OH;D1;+0:11]):[cH;D2;+0:12]:[n;H0;D2;+0:13]:[cH;D2;+0:14]:1.[CH3;D1;+0:15]-[N;H0;D3;+0:16](-[CH3;D1;+0:17])-[CH;D2;+0:18]=[O;H0;D1;+0:19]>>[Br;D1;H0:20]-[c;H0;D3;+0:2]1:[c... | 120.4 | [{"value": 120.4, "product": "BrC=1C=NC=C(C1)COCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | (5-Bromopyridin-3-yl)methanol was prepared according to the published procedure (Zhang, N. et al, J. Med. Chem., 45, 2832–2840 (2002)). A solution of (5-bromopyridin-3-yl)methanol (7.39 g, 39.3 mmol) in THF was cooled to 0° C. Sodium bis(trimethylsilyl)amide (39.3 mL of a 1.0 M solution in THF) was added, and the react... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amide.Primary alcohol.Silyl protective group.Silyl protective group | Aromatic halide.Ether.Primary alcohol | c1ccncc1 | c1ccncc1.c1ccncc1 | c1ccncc1.c1ccncc1 | HI | C1CCOC1.[Cl-].[Na+].O | null | 0.333333 | CCI.CN(C)C=O.C[Si](C)(C)[N-][Si](C)(C)C.OCc1cncc(Br)c1>C1CCOC1.[Cl-].[Na+].O>CCOCc1cncc(Br)c1.OCc1cncc(Br)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-395c3b609d4b49cb8302ff782ff91fc2 | CC(C)(O)CNc1c(N)cnc2cc(Br)ccc12.COCCC(=O)Cl>>COCCc1nc2cnc3cc(Br)ccc3c2n1CC(C)(C)O | NC=1C=NC2=CC(=CC=C2C1NCC(C)(O)C)Br.COCCC(=O)Cl>>BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CC(C)(O)C)CCOC | [NH2:6][c:7]1[cH:8][n:9][c:10]2[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]2[c:17]1[NH:18][CH2:19][C:20]([CH3:21])([CH3:22])[OH:23].O=[C:5](Cl)[CH2:4][CH2:3][O:2][CH3:1]>>[CH3:1][O:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]3[c:17]2[n:18]1[CH2:19][C:20]([CH3:21])([CH3:22]... | CC(C)(O)CNc1c(N)cnc2cc(Br)ccc12.COCCC(=O)Cl | COCCc1nc2cnc3cc(Br)ccc3c2n1CC(C)(C)O | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 101a087a520f159c722ba3d78ed38f5c3c1cf154206e5edbeb1e6397c929560f | 56ef83dfadec35a1cf1db968b807e178cc4924ce15bf36d774883783cef0f450 | c1ccc2c(c1)ncc1nc[nH]c12 | Cl-[C;H0;D3;+0:1](=O)-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1-[NH2;D1;+0:13]>>[C:4]-[C:5]-[n;H0;D3;+0:6]1:[c:7]2:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:2:[n;H0;D2;+0:13]:[c;H0;D3;+0:1]:1-[C:2]-[C:3] | 37.6 | [{"value": 37.6, "product": "BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CC(C)(O)C)CCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The method described in Part A of Example 9 was used to react 1-(3-amino-7-bromoquinolin-4-ylamino)-2-methylpropan-2-ol (29.0 g, 93.5 mmol) with 3-methoxypropionyl chloride (11.5 g, 93.5 mmol). The crude product was recrystallized from 2:1 ethyl acetate:hexane and then purified by flash column chromatography on silica ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine.Secondary amine | null | c1ccc2ncccc2c1 | c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12 | HCl | null | null | null | CC(C)(O)CNc1c(N)cnc2cc(Br)ccc12.COCCC(=O)Cl>>COCCc1nc2cnc3cc(Br)ccc3c2n1CC(C)(C)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-02ae989cd742463bb79e291df0179b6e | CC(C)(O)CNc1c(N)cnc2cc(Br)ccc12.CCOC(CC)(OCC)OCC>>CCc1nc2cnc3cc(Br)ccc3c2n1CC(C)(C)O | C(CC)(OCC)(OCC)OCC.NC=1C=NC2=CC(=CC=C2C1NCC(C)(O)C)Br>>BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CC(C)(O)C)CC | [NH2:4][c:5]1[cH:6][n:7][c:8]2[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]2[c:15]1[NH:16][CH2:17][C:18]([CH3:19])([CH3:20])[OH:21].CCO[C:3](OCC)(OCC)[CH2:2][CH3:1]>>[CH3:1][CH2:2][c:3]1[n:4][c:5]2[cH:6][n:7][c:8]3[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]3[c:15]2[n:16]1[CH2:17][C:18]([CH3:19])([CH3:20])[OH:21] | CC(C)(O)CNc1c(N)cnc2cc(Br)ccc12.CCOC(CC)(OCC)OCC | CCc1nc2cnc3cc(Br)ccc3c2n1CC(C)(C)O | null | Cl.N1=CC=CC=C1 | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 8d87c769e65778c9400c7f523e0409ecf0ffad86543cd9fdd6ef4b239323db96 | a60e703c3cf5c0d933aa031358d338c45d96ec82dec3fc2d9f5dce06b9dcc651 | c1ccc2c(c1)ncc1nc[nH]c12 | C-C-O-[C;H0;D4;+0:1](-O-C-C)(-O-C-C)-[C:2]-[C;D1;H3:3].[C:4]-[C:5]-[NH;D2;+0:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1-[NH2;D1;+0:13]>>[C:4]-[C:5]-[n;H0;D3;+0:6]1:[c:7]2:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:2:[n;H0;D2;+0:13]:[c;H0;D3;+0:1]:1-[C:2]-[C;D1;H3:3] | 74.9 | [{"value": 74.9, "product": "BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CC(C)(O)C)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Triethyl orthopropionate (12.9 g, 73.2 mmol) and pyridine hydrochloride (220 mg) were added to a solution of 1-(3-amino-7-bromoquinolin-4-ylamino)-2-methylpropan-2-ol (22.1 g, 70.6 mmol) in anhydrous toluene (300 mL), and the reaction was heated at reflux for three hours. The reaction was allowed to cool to ambient tem... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Primary amine.Secondary amine | null | c1ccc2ncccc2c1 | c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12 | HO- | Cl.N1=CC=CC=C1.C1(=CC=CC=C1)C | null | 8 | CC(C)(O)CNc1c(N)cnc2cc(Br)ccc12.CCOC(CC)(OCC)OCC>Cl.N1=CC=CC=C1.C1(=CC=CC=C1)C>CCc1nc2cnc3cc(Br)ccc3c2n1CC(C)(C)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-27157f317997486caae24016ad7f66b9 | COCCC(=O)Cl.COCCc1nc2c(N)nc3cc(Br)ccc3c2n1CC(C)C.c1cncc(B2OCCCO2)c1>>COCCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC(C)C.COCCc1nc2c(N)nc3cc(Br)ccc3c2n1CC(C)C | B1(OCCCO1)C2=CN=CC=C2.COCCC(=O)Cl.BrC=1C=CC=2C3=C(C(=NC2C1)N)N=C(N3CC(C)C)CCOC>>BrC=1C=CC=2C3=C(C(=NC2C1)N)N=C(N3CC(C)C)CCOC.COCCC=1N(C2=C(C(=NC=3C=C(C=CC23)C=2C=NC=CC2)N)N1)CC(C)C | O=[C:36](Cl)[CH2:32][CH2:33][O:30][CH3:29].[CH3:1][O:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:38][c:39]3[cH:40][c:41]([Br:42])[cH:43][cH:44][c:45]3[c:23]2[n:24]1[CH2:25][CH:26]([CH3:11])[CH3:28].O1B([c:14]2[cH:15][cH:16][cH:17][n:18][cH:19]2)O[CH2:21][CH2:13][CH2:12]1>>[CH3:1][O:2][CH2:3][CH2:4][c:5]1[n:6][c:7... | COCCC(=O)Cl.COCCc1nc2c(N)nc3cc(Br)ccc3c2n1CC(C)C.c1cncc(B2OCCCO2)c1 | COCCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC(C)C.COCCc1nc2c(N)nc3cc(Br)ccc3c2n1CC(C)C | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 22eeef8d2867cd46bc9b0334f40a3c9f431e063346a181dfca12853c8e7a4524 | 8a03c963f30a59ff1b31f4b4b4c7ea5336540579bac90f8751e8dead2fccdf88 | c1ccc2c(c1)ncc1nc[nH]c12.c1cncc(-c2ccc3c(c2)ncc2nc[nH]c23)c1 | Cl-[C;H0;D3;+0:1](=O)-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[O;H0;D2;+0:4]-[C;D1;H3:5].O1-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-O-B-1-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[c:12]:[#7;a:13]:[c:14]:1.[C:15]-[c:16]1:[#7;a:17]:[c:18]2:[c;H0;D3;+0:19](:[#7;a:20]:1-[C:21]-[CH;D3;+0:22](-[C;D1;H3:23])-[CH3;D1;+0:24]):[c;H0;D3;+0:25](:[c:26... | null | [] | null | null | null | null | 7-Bromo-2-(2-methoxyethyl)-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine was prepared according to the procedures described in Parts A and B of Example 9 using methoxypropanoyl chloride instead of ethoxyacetyl chloride. 7-Bromo-2-(2-methoxyethyl)-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine was coupled w... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether | Ether.Primary amine | c1ccc2c(c1)ncc1[nH]cnc12.B1OCCCO1.c1ccncc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1.c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1.c1ccc2c(c1)ncc1[nH]cnc12 | B | null | null | null | COCCC(=O)Cl.COCCc1nc2c(N)nc3cc(Br)ccc3c2n1CC(C)C.c1cncc(B2OCCCO2)c1>>COCCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC(C)C.COCCc1nc2c(N)nc3cc(Br)ccc3c2n1CC(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-89710722be634071be32e1e455135d49 | CC(C)(C)[Si](C)(C)OCc1cncc(B(O)O)c1.COCCc1nc2c(N)nc3cc(Br)ccc3c2n1CC(C)C>>COCCc1nc2c(N)nc3cc(-c4cncc(CO)c4)ccc3c2n1CC(C)C | BrC=1C=CC=2C3=C(C(=NC2C1)N)N=C(N3CC(C)C)CCOC.[Si](C)(C)(C(C)(C)C)OCC=1C=C(C=NC1)B(O)O>>NC1=NC=2C=C(C=CC2C2=C1N=C(N2CC(C)C)CCOC)C=2C=C(C=NC2)CO | CC(C)(C)[Si](C)(C)[O:20][CH2:19][c:18]1[cH:17][n:16][cH:15][c:14](B(O)O)[cH:21]1.Br[c:13]1[cH:12][c:11]2[n:10][c:8]([NH2:9])[c:7]3[n:6][c:5]([CH2:4][CH2:3][O:2][CH3:1])[n:26]([CH2:27][CH:28]([CH3:29])[CH3:30])[c:25]3[c:24]2[cH:23][cH:22]1>>[CH3:1][O:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:... | CC(C)(C)[Si](C)(C)OCc1cncc(B(O)O)c1.COCCc1nc2c(N)nc3cc(Br)ccc3c2n1CC(C)C | COCCc1nc2c(N)nc3cc(-c4cncc(CO)c4)ccc3c2n1CC(C)C | null | null | null | C-C Coupling | OtherReaction | 7e8e494468fec989e28e71c5f1c2fd0a84fe5aaf7514dc78f19f4105e118149d | a06ef17bc21d1c24abf9db7738e014318bfc7beb94875100ee37eca1fd591678 | c1cncc(-c2ccc3c(c2)ncc2nc[nH]c23)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[c:6](:[#7;a:7]):[c:8](:[#7;a:9]):[c:10]:2:[c:11]:[c:12]:1.C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:13]-[C:14]-[c:15]1:[c:16]:[#7;a:17]:[c:18]:[c;H0;D3;+0:19](-B(-O)-O):[c:20]:1>>[#7;a:9]:[c:8]1:[c:10]2:[c:11]:[c:12]:[c;H0;D3;+0:1](-[c;H0;D3;+0:19]3:[c:18]:[#7;a:17]:[c:16]:[c:... | null | [] | null | null | null | null | 7-Bromo-2-(2-methoxyethyl)-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine was coupled with 5-(tert-butyldimethylsilanyloxymethyl)pyridine-3-boronic acid according to the method described in Examples 118–121. The reaction was heated at reflux for 2.25 hours, and the work-up procedure described in Part F of Example... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid.TMS ether protective group | Primary alcohol | c1ccncc1.c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1 | HBr.B | null | null | null | CC(C)(C)[Si](C)(C)OCc1cncc(B(O)O)c1.COCCc1nc2c(N)nc3cc(Br)ccc3c2n1CC(C)C>>COCCc1nc2c(N)nc3cc(-c4cncc(CO)c4)ccc3c2n1CC(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ab593658aea3483d87d1ad57cc97e475 | CC(C)(C)OC(=O)NCCCCNc1c([N+](=O)[O-])cnc2cc(Br)ccc12>>CC(C)(C)OC(=O)NCCCCNc1c(N)cnc2cc(Br)ccc12 | S(=O)([O-])S(=O)[O-].[Na+].[Na+].C([O-])([O-])=O.[K+].[K+].C(C)(C)(C)OC(NCCCCNC1=C(C=NC2=CC(=CC=C12)Br)[N+](=O)[O-])=O>>C(C)(C)(C)OC(NCCCCNC1=C(C=NC2=CC(=CC=C12)Br)N)=O | O=[N+:16]([O-])[c:15]1[c:14]([NH:13][CH2:12][CH2:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[c:25]2[c:19]([n:18][cH:17]1)[cH:20][c:21]([Br:22])[cH:23][cH:24]2>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][c:14]1[c:15]([NH2:16])[cH:17][n:18][c... | CC(C)(C)OC(=O)NCCCCNc1c([N+](=O)[O-])cnc2cc(Br)ccc12 | CC(C)(C)OC(=O)NCCCCNc1c(N)cnc2cc(Br)ccc12 | null | [Br-].[Br-].C(C)[N+]1=CC=C(C=C1)C1=CC=[N+](C=C1)CC | ClCCl.O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2ncccc2c1 | 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] | 99 | [{"value": 99.0, "product": "C(C)(C)(C)OC(NCCCCNC1=C(C=NC2=CC(=CC=C12)Br)N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of sodium hydrosulfite (43.35 g, 249 mmol) and potassium carbonate (38.28 g, 277 mmol) in water (300 mL) was added to a mixture of tert-butyl[4-(7-bromo-3-nitroquinolin-4-ylamino)butyl]carbamate (24.3 g, 55.3 mmol) and 1,1′-diethyl-4,4′-bipyridinium dibromide (1.03 g, 2.76 mmol) in dichloromethane (368 mL) a... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2ncccc2c1 | Other | [Br-].[Br-].C(C)[N+]1=CC=C(C=C1)C1=CC=[N+](C=C1)CC.ClCCl.O | null | 8 | CC(C)(C)OC(=O)NCCCCNc1c([N+](=O)[O-])cnc2cc(Br)ccc12>[Br-].[Br-].C(C)[N+]1=CC=C(C=C1)C1=CC=[N+](C=C1)CC.ClCCl.O>CC(C)(C)OC(=O)NCCCCNc1c(N)cnc2cc(Br)ccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7fc97130c44c4ab6862ae4441f6c5ab3 | CCOCc1nc2cnc3cc(Br)ccc3c2n1CCCCNC(=O)OC(C)(C)C>>CCOCc1nc2cnc3cc(Br)ccc3c2n1CCCCN | Cl.C(C)(C)(C)OC(NCCCCN1C(=NC=2C=NC=3C=C(C=CC3C21)Br)COCC)=O>>BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CCCCN)COCC | CC(C)(C)OC(=O)[NH:23][CH2:22][CH2:21][CH2:20][CH2:19][n:18]1[c:5]([CH2:4][O:3][CH2:2][CH3:1])[n:6][c:7]2[cH:8][n:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]3[c:17]21>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]3[c:17]2[n:18]1[CH2:19][CH2:20][CH2:21][CH... | CCOCc1nc2cnc3cc(Br)ccc3c2n1CCCCNC(=O)OC(C)(C)C | CCOCc1nc2cnc3cc(Br)ccc3c2n1CCCCN | null | null | C(C)O | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc2c(c1)ncc1nc[nH]c12 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | 93.9 | [{"value": 93.9, "product": "BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CCCCN)COCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Concentrated hydrochloric acid (15.6 mL, 0.194 mol) was added to a solution of tert-butyl[4-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]carbamate (23.2 g, 48 mmol) in ethanol, and the reaction was heated at reflux for 20 minutes. A precipitate formed, and the reaction was allowed to cool to ambient tem... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2c(c1)ncc1[nH]cnc12 | HO- | C(C)O | null | null | CCOCc1nc2cnc3cc(Br)ccc3c2n1CCCCNC(=O)OC(C)(C)C>C(C)O>CCOCc1nc2cnc3cc(Br)ccc3c2n1CCCCN |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5987f786235c405b8c7944aed4cb6087 | CC(C)(C)OC(=O)NCCCCNc1c(N)cnc2cc(Br)ccc12.CCCc1nc2cnc3cc(Br)ccc3c2n1CCCCNC(=O)OC(C)(C)C>>CCCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCNC(=O)OC(C)(C)C | C(C)(C)(C)OC(NCCCCNC1=C(C=NC2=CC(=CC=C12)Br)N)=O.C(CCC)(=O)Cl.C(C)(C)(C)OC(NCCCCN1C(=NC=2C=NC=3C=C(C=CC3C21)Br)CCC)=O>>C(C)(C)(C)OC(NCCCCN1C(=NC=2C(=NC=3C=C(C=CC3C21)Br)N)CCC)=O | CC(C)(C)OC(=O)NCCCCNc1c2ccc(Br)cc2nc[c:7]1[NH2:8].c1[c:6]2[n:5][c:4]([CH2:3][CH2:2][CH3:1])[n:18]([CH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])[c:17]2[c:16]2[c:10]([n:9]1)[cH:11][c:12]([Br:13])[cH:14][cH:15]2>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]2[c:7]([NH2:8])[n:9][c:... | CC(C)(C)OC(=O)NCCCCNc1c(N)cnc2cc(Br)ccc12.CCCc1nc2cnc3cc(Br)ccc3c2n1CCCCNC(=O)OC(C)(C)C | CCCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCNC(=O)OC(C)(C)C | null | null | null | Miscellaneous | OtherReaction | fb10f8a85b614d4ce380f86b388af3e848211ee5aa02ec6cfb04b5e4266c42a3 | b8bf564d25195599ebf41896df823cfdb0e024456b80eb954e12ecfad8055d4d | c1ccc2c(c1)ncc1nc[nH]c12 | Br-c1:c:c:c2:c(-N-C-C-C-C-N-C(=O)-O-C(-C)(-C)-C):[c;H0;D3;+0:1](-[N;D1;H2:2]):c:n:c:2:c:1.[C:3]-[#7;a:4]1:[c:5]:[#7;a:6]:[c;H0;D3;+0:7]2:c:[n;H0;D2;+0:8]:[c:9](:[c:10]):[c:11]:[c:12]:1:2>>[C:3]-[#7;a:4]1:[c:5]:[#7;a:6]:[c;H0;D3;+0:7]2:[c:12]:1:[c:11]:[c:9](:[c:10]):[n;H0;D2;+0:8]:[c;H0;D3;+0:1]:2-[N;D1;H2:2] | null | [] | null | null | null | null | tert-Butyl[4-(3-amino-7-bromoquinolin-4-ylamino)butyl]carbamate was treated with butyryl chloride and cyclized according to the methods described in Part C and D of Examples 125–135. The resulting product, tert-butyl[4-(7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]carbamate was oxidized and aminated according ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester.Ether.Secondary amine.Boc | null | c1ccc2ncccc2c1.c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12 | HBr | null | null | null | CC(C)(C)OC(=O)NCCCCNc1c(N)cnc2cc(Br)ccc12.CCCc1nc2cnc3cc(Br)ccc3c2n1CCCCNC(=O)OC(C)(C)C>>CCCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCNC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-64210660bf0948f5bd7e03f4a92c51a0 | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC1COC(C)(C)O1>>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC(O)CO | Cl.CC1(OCC(O1)CN1C(=NC=2C(=NC=3C=C(C=CC3C21)C=2C=NC=CC2)N)COCC)C>>NC1=NC=2C=C(C=CC2C2=C1N=C(N2CC(CO)O)COCC)C=2C=NC=CC2 | CC1(C)[O:27][CH:26]([CH2:25][n:24]2[c:5]([CH2:4][O:3][CH2:2][CH3:1])[n:6][c:7]3[c:8]([NH2:9])[n:10][c:11]4[cH:12][c:13](-[c:14]5[cH:15][cH:16][cH:17][n:18][cH:19]5)[cH:20][cH:21][c:22]4[c:23]32)[CH2:28][O:29]1>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13](-[c:14]4[cH:15][cH:16][cH... | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC1COC(C)(C)O1 | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC(O)CO | null | null | C1CCOC1 | Deprotection | Acetal hydrolysis to diol | 5f7e1daa6b91d1ca6716348acae46f804565b19cb8bd8a05be2ed6c083743e87 | d0de49ebcb43eafba55a762f6d5237c53d7a87b3a882d6753f793a17a3c3a120 | c1cncc(-c2ccc3c(c2)ncc2nc[nH]c23)c1 | C-C1(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])-[C:4]-[O;H0;D2;+0:5]-1>>[C:3]-[C:2](-[OH;D1;+0:1])-[C:4]-[OH;D1;+0:5] | 89.6 | [{"value": 89.6, "product": "NC1=NC=2C=C(C=CC2C2=C1N=C(N2CC(CO)O)COCC)C=2C=NC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Hydrochloric acid (12 mL of 1 N) was added to a solution of 1-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine (0.75 g, 1.73 mmol) in THF, and the reaction was stirred overnight at ambient temperature. The THF was removed under reduced pressure, and 1% aqueous s... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Primary alcohol.Secondary alcohol | C1COCO1 | null | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1 | Other | C1CCOC1 | null | 8 | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC1COC(C)(C)O1>C1CCOC1>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC(O)CO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-808e43500c7f426ea4c6f20f0b65c5de | COCCCN.O=[N+]([O-])c1cnc2cc(Br)ccc2c1Cl>>COCCCNc1c([N+](=O)[O-])cnc2cc(Br)ccc12 | BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])Cl.COCCCN>>BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])NCCCOC | [CH3:1][O:2][CH2:3][CH2:4][CH2:5][NH2:6].Cl[c:7]1[c:8]([N+:9](=[O:10])[O-:11])[cH:12][n:13][c:14]2[cH:15][c:16]([Br:17])[cH:18][cH:19][c:20]12>>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][NH:6][c:7]1[c:8]([N+:9](=[O:10])[O-:11])[cH:12][n:13][c:14]2[cH:15][c:16]([Br:17])[cH:18][cH:19][c:20]12 | COCCCN.O=[N+]([O-])c1cnc2cc(Br)ccc2c1Cl | COCCCNc1c([N+](=O)[O-])cnc2cc(Br)ccc12 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 45e8470a78418ade39424f40732aa5ecf6717a7e5d47830a67429c5970ebd551 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc2ncccc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]:[c:8]:1-[#7;+:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[#7;+:9]-[c:8]1:[c:7]:[#7;a:6]:[c:4](:[c:5]):[c:2](:[c:3]):[c;H0;D3;+0:1]:1-[NH;D2;+0:12]-[C:11]-[C:10] | 94.2 | [{"value": 94.2, "product": "BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])NCCCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 7-Bromo-4-chloro-3-nitroquinoline (29.54 g, 102.7 mmol) was reacted with 3-methoxy propyl amine (10.07 g, 113.0 mmol) according to the method described in Part A of Examples 125–135 to provide 32.9 g of (7-bromo-3-nitroquinolin-4-yl)-(3-methoxypropyl)amine as a yellow solid. The product was not recrystallized.
Conditio... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HCl | null | null | null | COCCCN.O=[N+]([O-])c1cnc2cc(Br)ccc2c1Cl>>COCCCNc1c([N+](=O)[O-])cnc2cc(Br)ccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-04d591006e5b432d8b0818bceb09fc67 | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CC1CCN(C(=O)OC(C)(C)C)CC1.c1cncc(B2OCCCO2)c1>>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC1CCN(C(=O)OC(C)(C)C)CC1 | NC1=NC=2C=C(C=CC2C2=C1N=C(N2CC2CCN(CC2)C(=O)OC(C)(C)C)COCC)Br.B1(OCCCO1)C2=CN=CC=C2>>NC1=NC=2C=C(C=CC2C2=C1N=C(N2CC2CCN(CC2)C(=O)OC(C)(C)C)COCC)C=2C=NC=CC2 | Br[c:13]1[cH:12][c:11]2[n:10][c:8]([NH2:9])[c:7]3[n:6][c:5]([CH2:4][O:3][CH2:2][CH3:1])[n:24]([CH2:25][CH:26]4[CH2:27][CH2:28][N:29]([C:30](=[O:31])[O:32][C:33]([CH3:34])([CH3:35])[CH3:36])[CH2:37][CH2:38]4)[c:23]3[c:22]2[cH:21][cH:20]1.C1COB([c:14]2[cH:15][cH:16][cH:17][n:18][cH:19]2)OC1>>[CH3:1][CH2:2][O:3][CH2:4][c:... | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CC1CCN(C(=O)OC(C)(C)C)CC1.c1cncc(B2OCCCO2)c1 | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC1CCN(C(=O)OC(C)(C)C)CC1 | null | null | null | C-C Coupling | Suzuki coupling with boronic esters | 2cd1cbe6f17c98cb5223a75d20dfc144a6eae8461c4fe8a7e9cc4bc7ecadb166 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1cncc(-c2ccc3c(c2)ncc2ncn(CC4CCNCC4)c23)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[c:6](:[#7;a:7]):[c:8](:[#7;a:9]):[c:10]:2:[c:11]:[c:12]:1.C1-C-O-B(-[c;H0;D3;+0:13]2:[c:14]:[c:15]:[c:16]:[#7;a:17]:[c:18]:2)-O-C-1>>[#7;a:9]:[c:8]1:[c:10]2:[c:11]:[c:12]:[c;H0;D3;+0:1](-[c;H0;D3;+0:13]3:[c:14]:[c:15]:[c:16]:[#7;a:17]:[c:18]:3):[c:2]:[c:3]:2:[#7;a:4]:[c:5... | 85.4 | [{"value": 85.4, "product": "NC1=NC=2C=C(C=CC2C2=C1N=C(N2CC2CCN(CC2)C(=O)OC(C)(C)C)COCC)C=2C=NC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | tert-Butyl 4-[(4-amino-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]piperidine-1-carboxylate (12.79 g, 24.67 mmol) and pyrdine-3-boronic acid 1,3-propanediol cyclic ester (4.42 g, 27.14 mmol) were coupled according to the method described in Examples 118–121. The work-up procedure described in Part F of... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2c(c1)ncc1[nH]cnc12.B1OCCCO1.c1ccncc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1.C1CC[NH]CC1 | HBr.B | null | null | null | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CC1CCN(C(=O)OC(C)(C)C)CC1.c1cncc(B2OCCCO2)c1>>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC1CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7f6c6e3fc28f475d81766645384bb24d | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC1CCN(C(=O)OC(C)(C)C)CC1>>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC1CCNCC1.Cl.Cl | Cl.NC1=NC=2C=C(C=CC2C2=C1N=C(N2CC2CCN(CC2)C(=O)OC(C)(C)C)COCC)C=2C=NC=CC2>>Cl.Cl.Cl.C(C)OCC=1N(C2=C(C(=NC=3C=C(C=CC23)C=2C=NC=CC2)N)N1)CC1CCNCC1 | CC(C)(C)OC(=O)[N:29]1[CH2:28][CH2:27][CH:26]([CH2:25][n:24]2[c:5]([CH2:4][O:3][CH2:2][CH3:1])[n:6][c:7]3[c:8]([NH2:9])[n:10][c:11]4[cH:12][c:13](-[c:14]5[cH:15][cH:16][cH:17][n:18][cH:19]5)[cH:20][cH:21][c:22]4[c:23]32)[CH2:31][CH2:30]1>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13... | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC1CCN(C(=O)OC(C)(C)C)CC1 | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC1CCNCC1.Cl.Cl | null | null | C(C)O | Miscellaneous | Boc amine deprotection | 0d17b1cd8faa9642170a265595f8fea596067098aa2d20db6ef6a923fda4571d | c95e79e18f8ea11cf22745e0eab38cab98566b1b63e7d80ee200f4cb4f94f00c | c1cncc(-c2ccc3c(c2)ncc2ncn(CC4CCNCC4)c23)c1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | null | [] | null | null | null | null | Ethanolic hydrochloric acid (17.68 mL of 4.25 M) was added to a solution of tert-butyl 4-{[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}piperidine-1-carboxylate (9.71 g, 18.8 mmol) in anhydrous ethanol, and the reaction was heated at reflux for two hours. A precipitate formed, and the r... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1.C1CCNCC1 | HO- | C(C)O | null | null | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC1CCN(C(=O)OC(C)(C)C)CC1>C(C)O>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC1CCNCC1.Cl.Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-18c55e75a5c248f0a49de337c375323e | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC1CCNCC1.O=C(O)C1CCCO1>>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC1CCN(C(=O)C2CCCO2)CC1 | Cl.Cl.Cl.C(C)OCC=1N(C2=C(C(=NC=3C=C(C=CC23)C=2C=NC=CC2)N)N1)CC1CCNCC1.C(C)N(CC)CC.O1C(CCC1)C(=O)O.Cl.CON(CCCN=C=NCC)OC.ON1N=NC2=C1C=CC=C2>>C(C)OCC=1N(C2=C(C(=NC=3C=C(C=CC23)C=2C=NC=CC2)N)N1)CC1CCN(CC1)C(=O)C1OCCC1 | [CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13](-[c:14]4[cH:15][cH:16][cH:17][n:18][cH:19]4)[cH:20][cH:21][c:22]3[c:23]2[n:24]1[CH2:25][CH:26]1[CH2:27][CH2:28][NH:29][CH2:37][CH2:38]1.O[C:30](=[O:31])[CH:32]1[CH2:33][CH2:34][CH2:35][O:36]1>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2... | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC1CCNCC1.O=C(O)C1CCCO1 | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC1CCN(C(=O)C2CCCO2)CC1 | null | null | C(Cl)(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | fbfce93ec1ece674255bb96c5cec09ad611382b41cf117dfe580015e21744a71 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(C1CCCO1)N1CCC(Cn2cnc3cnc4cc(-c5cccnc5)ccc4c32)CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#8:5]-[C:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#8:5]-[C:6])-[C:10]-[C:11] | 69.5 | [{"value": 69.5, "product": "C(C)OCC=1N(C2=C(C(=NC=3C=C(C=CC23)C=2C=NC=CC2)N)N1)CC1CCN(CC1)C(=O)C1OCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 4 | CELSIUS | 2 | HOUR | A solution of 2-ethoxymethyl-1-(piperidin-4-ylmethyl)-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine trihydrochloride (1.0 g, 1.90 mmol) and triethylamine (1.35 mL, 9.50 mmol) in chloroform (80 mL) was cooled to 4° C. 2-Tetrahydrofuroic acid (0.243 g, 2.09 mmol) and 1-(3-dimethoxyaminopropyl)-3-ethylcarbodiimide hy... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1.C1CC[NH]CC1.C1CCOC1 | HO- | C(Cl)(Cl)Cl | 4 | 2 | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC1CCNCC1.O=C(O)C1CCCO1>C(Cl)(Cl)Cl>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC1CCN(C(=O)C2CCCO2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-430d0386e8414621b64afa9b24284926 | NCCCN1CCCC1=O.O=[N+]([O-])c1cnc2cc(Br)ccc2c1Cl>>O=C1CCCN1CCCNc1c([N+](=O)[O-])cnc2cc(Br)ccc12 | BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])Cl.NCCCN1C(CCC1)=O>>BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])NCCCN1C(CCC1)=O | [O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][CH2:9][NH2:10].Cl[c:11]1[c:12]([N+:13](=[O:14])[O-:15])[cH:16][n:17][c:18]2[cH:19][c:20]([Br:21])[cH:22][cH:23][c:24]12>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][CH2:9][NH:10][c:11]1[c:12]([N+:13](=[O:14])[O-:15])[cH:16][n:17][c:18]2[cH:19][c:20]([Br:21... | NCCCN1CCCC1=O.O=[N+]([O-])c1cnc2cc(Br)ccc2c1Cl | O=C1CCCN1CCCNc1c([N+](=O)[O-])cnc2cc(Br)ccc12 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 45e8470a78418ade39424f40732aa5ecf6717a7e5d47830a67429c5970ebd551 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C1CCCN1CCCNc1ccnc2ccccc12 | Cl-[c;H0;D3;+0:1]1:[c:2](-[#7;+:3]):[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[#7;+:3]-[c:2]1:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8](:[c:9]):[c;H0;D3;+0:1]:1-[NH;D2;+0:12]-[C:11]-[C:10] | 84 | [{"value": 84.0, "product": "BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])NCCCN1C(CCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 7-Bromo-4-chloro-3-nitroquinoline (35.26 g, 123.8 mmol) was treated with 1-(3-aminopropyl)pyrrolidin-2-one (19.1 mL, 136.2 mmol) according to the method described in Part E of Example 1 to provide 40.87 g of 1-[3-(7-bromo-3-nitroquinolin-4-ylamino)propyl]pyrrolidin-2-one as a yellow solid.
Conditions: See reaction.note... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | C1CC[NH]C1.c1ccc2ncccc2c1 | HCl | null | null | null | NCCCN1CCCC1=O.O=[N+]([O-])c1cnc2cc(Br)ccc2c1Cl>>O=C1CCCN1CCCNc1c([N+](=O)[O-])cnc2cc(Br)ccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-73b5eeb65ee0473787a827af92511bab | COCCC(=O)Cl.O=C1CCCN1CCCNc1c([N+](=O)[O-])cnc2cc(Br)ccc12>>COCCc1nc2cnc3cc(Br)ccc3c2n1CCCN1CCCC1=O | BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])NCCCN1C(CCC1)=O.COCCC(=O)Cl.C(C)N(CC)CC>>BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CCCN3C(CCC3)=O)CCOC | O=[C:5](Cl)[CH2:4][CH2:3][O:2][CH3:1].O=[N+:6]([O-])[c:7]1[cH:8][n:9][c:10]2[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]2[c:17]1[NH:18][CH2:19][CH2:20][CH2:21][N:22]1[CH2:23][CH2:24][CH2:25][C:26]1=[O:27]>>[CH3:1][O:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]3[c:17]2[n:18... | COCCC(=O)Cl.O=C1CCCN1CCCNc1c([N+](=O)[O-])cnc2cc(Br)ccc12 | COCCc1nc2cnc3cc(Br)ccc3c2n1CCCN1CCCC1=O | null | null | null | Aromatic Heterocycle Formation | OtherReaction | f5ccfa638b9ebde84faf3ed5ae8aa34e1d73a7445584b4a71cf926baaa6ffdb4 | 65afb0bd4703d35942ab9e6c52b2a1e949dd1e9f7cc47623826614e8c0ed673b | O=C1CCCN1CCCn1cnc2cnc3ccccc3c21 | Cl-[C;H0;D3;+0:1](=O)-[C:2]-[C:3].O=[N+;H0;D3:4](-[O-])-[c:5]1:[c:6]:[#7;a:7]:[c:8]:[c:9]:[c:10]:1-[NH;D2;+0:11]-[C:12]-[C:13]>>[C:13]-[C:12]-[n;H0;D3;+0:11]1:[c:10]2:[c:9]:[c:8]:[#7;a:7]:[c:6]:[c:5]:2:[n;H0;D2;+0:4]:[c;H0;D3;+0:1]:1-[C:2]-[C:3] | null | [] | null | null | null | null | 1-[3-(7-Bromo3-nitroquinolin-4-ylamino)propyl]pyrrolidin-2-one was treated according to the methods described in Parts B, C, and D of Examples 152–156. 3-Methoxypropionyl chloride was used in Part C, and triethylamine (1.3 equivalents) was added to the reaction mixture. The crude product obtained in Part D was purified... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Nitro group.Secondary amine | null | c1ccc2ncccc2c1 | c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12.C1CC[NH]C1 | HCl | null | null | null | COCCC(=O)Cl.O=C1CCCN1CCCNc1c([N+](=O)[O-])cnc2cc(Br)ccc12>>COCCc1nc2cnc3cc(Br)ccc3c2n1CCCN1CCCC1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9bc5d76282ce46f99fc9bea711c2f243 | NCCCN1CCCC1=O.O=[N+]([O-])c1cnc2ccc(Br)cc2c1Cl>>O=C1CCCN1CCCNc1c([N+](=O)[O-])cnc2ccc(Br)cc12 | BrC=1C=C2C(=C(C=NC2=CC1)[N+](=O)[O-])Cl.BrC1=CC=C(N)C=C1.NCCCN1C(CCC1)=O>>BrC=1C=C2C(=C(C=NC2=CC1)[N+](=O)[O-])NCCCN1C(CCC1)=O | [O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][CH2:9][NH2:10].Cl[c:11]1[c:12]([N+:13](=[O:14])[O-:15])[cH:16][n:17][c:18]2[cH:19][cH:20][c:21]([Br:22])[cH:23][c:24]12>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][CH2:9][NH:10][c:11]1[c:12]([N+:13](=[O:14])[O-:15])[cH:16][n:17][c:18]2[cH:19][cH:20][c:21]... | NCCCN1CCCC1=O.O=[N+]([O-])c1cnc2ccc(Br)cc2c1Cl | O=C1CCCN1CCCNc1c([N+](=O)[O-])cnc2ccc(Br)cc12 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 45e8470a78418ade39424f40732aa5ecf6717a7e5d47830a67429c5970ebd551 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C1CCCN1CCCNc1ccnc2ccccc12 | Cl-[c;H0;D3;+0:1]1:[c:2](-[#7;+:3]):[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[#7;+:3]-[c:2]1:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8](:[c:9]):[c;H0;D3;+0:1]:1-[NH;D2;+0:12]-[C:11]-[C:10] | 87.8 | [{"value": 87.8, "product": "BrC=1C=C2C(=C(C=NC2=CC1)[N+](=O)[O-])NCCCN1C(CCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 6-Bromo-4-chloro-3-nitroquinoline (50.62 g, 177.8 mmol), prepared from 4-bromoaniline according to the methods described in Parts A–D of Example 1, was treated with 1-(3-aminopropyl)pyrrolidin-2-one (27.5 mL, 196 mmol) according to the method described in Part E of Example 1 to provide 61.41 g of 1-[3-(6-bromo-3-nitroq... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | C1CC[NH]C1.c1ccc2ncccc2c1 | HCl | null | null | null | NCCCN1CCCC1=O.O=[N+]([O-])c1cnc2ccc(Br)cc2c1Cl>>O=C1CCCN1CCCNc1c([N+](=O)[O-])cnc2ccc(Br)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e0999a8e80fc4a5f8946b95e27730253 | COCCC(=O)Cl.O=C1CCCN1CCCNc1c([N+](=O)[O-])cnc2ccc(Br)cc12>>COCCc1nc2cnc3ccc(Br)cc3c2n1CCCN1CCCC1=O | BrC=1C=C2C(=C(C=NC2=CC1)[N+](=O)[O-])NCCCN1C(CCC1)=O.COCCC(=O)Cl>>BrC1=CC=2C3=C(C=NC2C=C1)N=C(N3CCCN3C(CCC3)=O)CCOC | O=[C:5](Cl)[CH2:4][CH2:3][O:2][CH3:1].O=[N+:6]([O-])[c:7]1[cH:8][n:9][c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][c:16]2[c:17]1[NH:18][CH2:19][CH2:20][CH2:21][N:22]1[CH2:23][CH2:24][CH2:25][C:26]1=[O:27]>>[CH3:1][O:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:9][c:10]3[cH:11][cH:12][c:13]([Br:14])[cH:15][c:16]3[c:17]2[n:18... | COCCC(=O)Cl.O=C1CCCN1CCCNc1c([N+](=O)[O-])cnc2ccc(Br)cc12 | COCCc1nc2cnc3ccc(Br)cc3c2n1CCCN1CCCC1=O | null | null | null | Aromatic Heterocycle Formation | OtherReaction | e5efb7579e56d5ca9ced81b81969524f7016f29e82a669fa5b2c9b856824998a | 65afb0bd4703d35942ab9e6c52b2a1e949dd1e9f7cc47623826614e8c0ed673b | O=C1CCCN1CCCn1cnc2cnc3ccccc3c21 | Cl-[C;H0;D3;+0:1](=O)-[C:2]-[C:3].O=[N+;H0;D3:4](-[O-])-[c:5]1:[c:6]:[#7;a:7]:[c:8]:[c:9]:[c:10]:1-[NH;D2;+0:11]-[C:12]-[C:13]>>[C:13]-[C:12]-[n;H0;D3;+0:11]1:[c:10]2:[c:9]:[c:8]:[#7;a:7]:[c:6]:[c:5]:2:[n;H0;D2;+0:4]:[c;H0;D3;+0:1]:1-[C:2]-[C:3] | null | [] | null | null | null | null | 1-[3-(6-Bromo3-nitroquinolin-4-ylamino)propyl]pyrrolidin-2-one was treated according to the methods described in Parts B, C, and D of Examples 152–156. 3-Methoxypropionyl chloride was used in Part C. The crude product obtained in Part D was recrystallized from acetonitrile. The crystals were washed with cold acetonitri... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Nitro group.Secondary amine | null | c1ccc2ncccc2c1 | c1ccc2ncc3[nH]cnc3c2c1 | c1ccc2ncc3[nH]cnc3c2c1.C1CC[NH]C1 | HCl | null | null | null | COCCC(=O)Cl.O=C1CCCN1CCCNc1c([N+](=O)[O-])cnc2ccc(Br)cc12>>COCCc1nc2cnc3ccc(Br)cc3c2n1CCCN1CCCC1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-49ad03b0f69c45cab1df976518211e4d | CC(C)(C)OC(=O)N1CCC(CN)CC1.O=[N+]([O-])c1cnc2cc(-c3ccccc3)ccc2c1Cl>>CC(C)(C)OC(=O)N1CCC(CNc2c([N+](=O)[O-])cnc3cc(-c4ccccc4)ccc23)CC1 | ClC1=C(C=NC2=CC(=CC=C12)C1=CC=CC=C1)[N+](=O)[O-].C(C)(C)(C)OC(=O)N1CCC(CC1)CN>>[N+](=O)([O-])C=1C=NC2=CC(=CC=C2C1NCC1CCN(CC1)C(=O)OC(C)(C)C)C1=CC=CC=C1 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([CH2:12][NH2:13])[CH2:33][CH2:34]1.Cl[c:14]1[c:15]([N+:16](=[O:17])[O-:18])[cH:19][n:20][c:21]2[cH:22][c:23](-[c:24]3[cH:25][cH:26][cH:27][cH:28][cH:29]3)[cH:30][cH:31][c:32]12>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2... | CC(C)(C)OC(=O)N1CCC(CN)CC1.O=[N+]([O-])c1cnc2cc(-c3ccccc3)ccc2c1Cl | CC(C)(C)OC(=O)N1CCC(CNc2c([N+](=O)[O-])cnc3cc(-c4ccccc4)ccc23)CC1 | null | null | C(C)OCC | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 45e8470a78418ade39424f40732aa5ecf6717a7e5d47830a67429c5970ebd551 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(-c2ccc3c(NCC4CCNCC4)ccnc3c2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2](-[#7;+:3]):[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[#7;+:3]-[c:2]1:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8](:[c:9]):[c;H0;D3;+0:1]:1-[NH;D2;+0:12]-[C:11]-[C:10] | 94.3 | [{"value": 94.3, "product": "[N+](=O)([O-])C=1C=NC2=CC(=CC=C2C1NCC1CCN(CC1)C(=O)OC(C)(C)C)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Chloro-3-nitro-7-phenylquinoline (8.35 g, 29.3 mmol) was treated with 1-(tert-butoxycarbonyl)-4-(aminomethyl)piperidine (7.54 g, 35.2 mmol) according to the method described in Part A of Examples 152–156. The crude solid was triturated with water, isolated by filtration, sonicated with diethyl ether, isolated by filt... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | C1CC[NH]CC1.c1ccc2ncccc2c1.c1ccccc1 | HCl | C(C)OCC | null | null | CC(C)(C)OC(=O)N1CCC(CN)CC1.O=[N+]([O-])c1cnc2cc(-c3ccccc3)ccc2c1Cl>C(C)OCC>CC(C)(C)OC(=O)N1CCC(CNc2c([N+](=O)[O-])cnc3cc(-c4ccccc4)ccc23)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c56825bcfe01483a83fa38235d7cbd81 | CCOCc1nc2c(N)nc3cc(-c4ccccc4)ccc3c2n1CC1CCN(C(=O)OC(C)(C)C)CC1>>CCOCc1nc2c(N)nc3cc(-c4ccccc4)ccc3c2n1CC1CCNCC1 | NC1=NC=2C=C(C=CC2C2=C1N=C(N2CC2CCN(CC2)C(=O)OC(C)(C)C)COCC)C2=CC=CC=C2.[OH-].[NH4+]>>C(C)OCC=1N(C2=C(C(=NC=3C=C(C=CC23)C2=CC=CC=C2)N)N1)CC1CCNCC1 | CC(C)(C)OC(=O)[N:29]1[CH2:28][CH2:27][CH:26]([CH2:25][n:24]2[c:5]([CH2:4][O:3][CH2:2][CH3:1])[n:6][c:7]3[c:8]([NH2:9])[n:10][c:11]4[cH:12][c:13](-[c:14]5[cH:15][cH:16][cH:17][cH:18][cH:19]5)[cH:20][cH:21][c:22]4[c:23]32)[CH2:31][CH2:30]1>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:1... | CCOCc1nc2c(N)nc3cc(-c4ccccc4)ccc3c2n1CC1CCN(C(=O)OC(C)(C)C)CC1 | CCOCc1nc2c(N)nc3cc(-c4ccccc4)ccc3c2n1CC1CCNCC1 | null | null | O | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(-c2ccc3c(c2)ncc2ncn(CC4CCNCC4)c23)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 54.3 | [{"value": 54.3, "product": "C(C)OCC=1N(C2=C(C(=NC=3C=C(C=CC23)C2=CC=CC=C2)N)N1)CC1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | tert-Butyl 4-[(4-amino-2-ethoxymethyl-7-phenyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]piperidine-1-carboxylate (0.64 g) was deprotected according to the method described in Example 177. The crude solid was dissolved in water (10 mL), and ammonium hydroxide was added until the solution was basic. The mixture was then ext... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccccc1.C1CCNCC1 | HO- | O | null | null | CCOCc1nc2c(N)nc3cc(-c4ccccc4)ccc3c2n1CC1CCN(C(=O)OC(C)(C)C)CC1>O>CCOCc1nc2c(N)nc3cc(-c4ccccc4)ccc3c2n1CC1CCNCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f72f99ec1a3a4a8dbe5376dce345964e | NCCOc1ccccc1.O=[N+]([O-])c1cnc2cc(-c3ccccc3)ccc2c1Cl>>O=[N+]([O-])c1cnc2cc(-c3ccccc3)ccc2c1NCCOc1ccccc1 | ClC1=C(C=NC2=CC(=CC=C12)C1=CC=CC=C1)[N+](=O)[O-].O(C1=CC=CC=C1)CCN>>[N+](=O)([O-])C=1C=NC2=CC(=CC=C2C1NCCOC1=CC=CC=C1)C1=CC=CC=C1 | [NH2:20][CH2:21][CH2:22][O:23][c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1.Cl[c:19]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][n:6][c:7]2[cH:8][c:9](-[c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[cH:16][cH:17][c:18]21>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][n:6][c:7]2[cH:8][c:9](-[c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[cH:16][cH:1... | NCCOc1ccccc1.O=[N+]([O-])c1cnc2cc(-c3ccccc3)ccc2c1Cl | O=[N+]([O-])c1cnc2cc(-c3ccccc3)ccc2c1NCCOc1ccccc1 | null | null | C(C)OCC | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 45e8470a78418ade39424f40732aa5ecf6717a7e5d47830a67429c5970ebd551 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(OCCNc2ccnc3cc(-c4ccccc4)ccc23)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]:[c:8]:1-[#7;+:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[#7;+:9]-[c:8]1:[c:7]:[#7;a:6]:[c:4](:[c:5]):[c:2](:[c:3]):[c;H0;D3;+0:1]:1-[NH;D2;+0:12]-[C:11]-[C:10] | 100.3 | [{"value": 100.3, "product": "[N+](=O)([O-])C=1C=NC2=CC(=CC=C2C1NCCOC1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Chloro-3-nitro-7-phenylquinoline (6.0 g, 21 mmol) was treated with 2-phenoxyethylamine (3.18 g, 23.2 mmol) according to the method described in Part A of Examples 125–135. The crude solid was triturated with water (100 mL), isolated by filtration, sonicated with diethyl ether, isolated by filtration, and dried for tw... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccccc1.c1ccccc1 | HCl | C(C)OCC | null | null | NCCOc1ccccc1.O=[N+]([O-])c1cnc2cc(-c3ccccc3)ccc2c1Cl>C(C)OCC>O=[N+]([O-])c1cnc2cc(-c3ccccc3)ccc2c1NCCOc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c6f8ff1a6e6447ae9d0992d40f4400f0 | O=[N+]([O-])c1cnc2cc(-c3ccccc3)ccc2c1NCCOc1ccccc1>>Nc1cnc2cc(-c3ccccc3)ccc2c1NCCOc1ccccc1 | [N+](=O)([O-])C=1C=NC2=CC(=CC=C2C1NCCOC1=CC=CC=C1)C1=CC=CC=C1>>O(C1=CC=CC=C1)CCNC1=C(C=NC2=CC(=CC=C12)C1=CC=CC=C1)N | O=[N+:1]([O-])[c:2]1[cH:3][n:4][c:5]2[cH:6][c:7](-[c:8]3[cH:9][cH:10][cH:11][cH:12][cH:13]3)[cH:14][cH:15][c:16]2[c:17]1[NH:18][CH2:19][CH2:20][O:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>>[NH2:1][c:2]1[cH:3][n:4][c:5]2[cH:6][c:7](-[c:8]3[cH:9][cH:10][cH:11][cH:12][cH:13]3)[cH:14][cH:15][c:16]2[c:17]1[NH:18][CH2:1... | O=[N+]([O-])c1cnc2cc(-c3ccccc3)ccc2c1NCCOc1ccccc1 | Nc1cnc2cc(-c3ccccc3)ccc2c1NCCOc1ccccc1 | null | [Pt] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(OCCNc2ccnc3cc(-c4ccccc4)ccc23)cc1 | 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 | null | null | A solution of (3-nitro-7-phenylquinolin-4-yl)-(2-phenoxyethyl)amine (7.25 g, 18.8 mmol) in methanol (150 mL) was added to a Parr vessel charged with 5% platinum on carbon (0.84 g), and the reaction was placed under hydrogen pressure (50 psi, 3.4×105 Pa) for three hours. The reaction mixture was filtered through a layer... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2ncccc2c1.c1ccccc1.c1ccccc1 | Other | [Pt].CO | null | null | O=[N+]([O-])c1cnc2cc(-c3ccccc3)ccc2c1NCCOc1ccccc1>[Pt].CO>Nc1cnc2cc(-c3ccccc3)ccc2c1NCCOc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6adf18b19dfd401ca036b2c8938a2b96 | CC(C)(C)OC(=O)NCCCCN.CS(=O)(=O)Cl>>CC(C)(C)OC(=O)NCCCCNS(C)(=O)=O | NCCCCNC(OC(C)(C)C)=O.C(C)N(CC)CC.CS(=O)(=O)Cl>>CS(=O)(=O)NCCCCNC(OC(C)(C)C)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][CH2:12][NH2:13].Cl[S:14]([CH3:15])(=[O:16])=[O:17]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][S:14]([CH3:15])(=[O:16])=[O:17] | CC(C)(C)OC(=O)NCCCCN.CS(=O)(=O)Cl | CC(C)(C)OC(=O)NCCCCNS(C)(=O)=O | null | null | C(C)(=O)O | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | null | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 96.7 | [{"value": 96.7, "product": "CS(=O)(=O)NCCCCNC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Under a nitrogen atmosphere, a solution of tert-butyl N-(4-aminobutyl)carbamate (13.8 g, 73.4 mmol) and triethylamine (15.3 mL, 110 mmol) was cooled to 0° C. Methanesulfonyl chloride (6.3 mL, 81 mmol) was added, and the reaction was allowed to warm to ambient temperature and stirred overnight. Aqueous acetic acid (200 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | null | HCl | C(C)(=O)O | null | 8 | CC(C)(C)OC(=O)NCCCCN.CS(=O)(=O)Cl>C(C)(=O)O>CC(C)(C)OC(=O)NCCCCNS(C)(=O)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3e1f5abfa6d942d1a82cf7baca23135b | CC(C)(C)OC(=O)NCCCCNS(C)(=O)=O>>CS(=O)(=O)NCCCCN | Cl.CS(=O)(=O)NCCCCNC(OC(C)(C)C)=O>>Cl.NCCCCNS(=O)(=O)C | CC(C)(C)OC(=O)[NH:10][CH2:9][CH2:8][CH2:7][CH2:6][NH:5][S:2]([CH3:1])(=[O:3])=[O:4]>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][CH2:6][CH2:7][CH2:8][CH2:9][NH2:10] | CC(C)(C)OC(=O)NCCCCNS(C)(=O)=O | CS(=O)(=O)NCCCCN | null | null | C(C)O | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | null | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | 100 | CELSIUS | null | null | A solution of hydrochloric acid in ethanol was added to a solution of tert-butyl [4-(methanesulfonylamino)butyl]carbamate (18.9 g, 71.1 mmol) in ethanol (100 mL), and the reaction was heated at 100° C. for two hours. The solvent was removed under reduced pressure. A mixture of dichloromethane:hexanes was added to the r... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | null | HO- | C(C)O | 100 | null | CC(C)(C)OC(=O)NCCCCNS(C)(=O)=O>C(C)O>CS(=O)(=O)NCCCCN |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8fccf99693c64fad9f96b1c8c8faeb9d | CS(=O)(=O)NCCCCN.O=[N+]([O-])c1cnc2cc(-c3ccccc3)ccc2c1Cl>>CS(=O)(=O)NCCCCNc1c([N+](=O)[O-])cnc2cc(-c3ccccc3)ccc12 | O.Cl.NCCCCNS(=O)(=O)C.ClC1=C(C=NC2=CC(=CC=C12)C1=CC=CC=C1)[N+](=O)[O-].C(C)N(CC)CC>>[N+](=O)([O-])C=1C=NC2=CC(=CC=C2C1NCCCCNS(=O)(=O)C)C1=CC=CC=C1 | [CH3:1][S:2](=[O:3])(=[O:4])[NH:5][CH2:6][CH2:7][CH2:8][CH2:9][NH2:10].Cl[c:11]1[c:12]([N+:13](=[O:14])[O-:15])[cH:16][n:17][c:18]2[cH:19][c:20](-[c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[cH:27][cH:28][c:29]12>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][CH2:6][CH2:7][CH2:8][CH2:9][NH:10][c:11]1[c:12]([N+:13](=[O:14])[O-:15]... | CS(=O)(=O)NCCCCN.O=[N+]([O-])c1cnc2cc(-c3ccccc3)ccc2c1Cl | CS(=O)(=O)NCCCCNc1c([N+](=O)[O-])cnc2cc(-c3ccccc3)ccc12 | null | null | CN1CCCC1=O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 45e8470a78418ade39424f40732aa5ecf6717a7e5d47830a67429c5970ebd551 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(-c2ccc3cccnc3c2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2](-[#7;+:3]):[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[#7;+:3]-[c:2]1:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8](:[c:9]):[c;H0;D3;+0:1]:1-[NH;D2;+0:12]-[C:11]-[C:10] | 82.7 | [{"value": 82.7, "product": "[N+](=O)([O-])C=1C=NC2=CC(=CC=C2C1NCCCCNS(=O)(=O)C)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | N-(4-aminobutyl)methanesulfonamide hydrochloride (7.8 g, 39 mmol) was added to a suspension of 4-chloro-3-nitro-7-phenylquinoline (35 mmol) and triethylamine (8.0 g, 79 mmol) in NMP (80 mL), and the reaction was stirred at ambient temperature overnight. The resulting solution was poured into water (350 mL) to form a so... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccccc1 | HCl | CN1CCCC1=O | null | 8 | CS(=O)(=O)NCCCCN.O=[N+]([O-])c1cnc2cc(-c3ccccc3)ccc2c1Cl>CN1CCCC1=O>CS(=O)(=O)NCCCCNc1c([N+](=O)[O-])cnc2cc(-c3ccccc3)ccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-488bb10254d64e94955ce5a59e9d54b2 | CC(C)(N)CN.O=[N+]([O-])c1cnc2cc(-c3ccccc3)ccc2c1Cl>>CC(C)(N)CNc1c([N+](=O)[O-])cnc2cc(-c3ccccc3)ccc12 | ClC1=C(C=NC2=CC(=CC=C12)C1=CC=CC=C1)[N+](=O)[O-].NCC(C)(C)N.C(C)N(CC)CC>>[N+](=O)([O-])C=1C=NC2=CC(=CC=C2C1NCC(C)(N)C)C1=CC=CC=C1 | [CH3:1][C:2]([CH3:3])([NH2:4])[CH2:5][NH2:6].Cl[c:7]1[c:8]([N+:9](=[O:10])[O-:11])[cH:12][n:13][c:14]2[cH:15][c:16](-[c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[cH:23][cH:24][c:25]12>>[CH3:1][C:2]([CH3:3])([NH2:4])[CH2:5][NH:6][c:7]1[c:8]([N+:9](=[O:10])[O-:11])[cH:12][n:13][c:14]2[cH:15][c:16](-[c:17]3[cH:18][cH:19][... | CC(C)(N)CN.O=[N+]([O-])c1cnc2cc(-c3ccccc3)ccc2c1Cl | CC(C)(N)CNc1c([N+](=O)[O-])cnc2cc(-c3ccccc3)ccc12 | null | null | ClCCl | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 45e8470a78418ade39424f40732aa5ecf6717a7e5d47830a67429c5970ebd551 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(-c2ccc3cccnc3c2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]:[c:8]:1-[#7;+:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[#7;+:9]-[c:8]1:[c:7]:[#7;a:6]:[c:4](:[c:5]):[c:2](:[c:3]):[c;H0;D3;+0:1]:1-[NH;D2;+0:12]-[C:11]-[C:10] | null | [] | null | null | null | null | A solution of 1,2-diamino-2-methylpropane (9.3 mL, 88.9 mmol) and triethylamine (5.0 mL, 35.5 mmol) in dichloromethane (100 mL) was cooled to 0° C. A solution of 4-chloro-3-nitro-7-phenylquinoline (5.06 g, 17.8 mmol) in dichloromethane (50 mL) was added over a period of 45 minutes, and then the reaction was allowed to ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccccc1 | HCl | ClCCl | null | null | CC(C)(N)CN.O=[N+]([O-])c1cnc2cc(-c3ccccc3)ccc2c1Cl>ClCCl>CC(C)(N)CNc1c([N+](=O)[O-])cnc2cc(-c3ccccc3)ccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b1f64bdf6e76463192b17da361ab9967 | CC(C)(CNc1c(N)cnc2cc(-c3ccccc3)ccc12)NS(C)(=O)=O.CCCC(OC)(OC)OC>>CCCc1nc2cnc3cc(-c4ccccc4)ccc3c2n1CC(C)(C)NS(C)(=O)=O | NC=1C=NC2=CC(=CC=C2C1NCC(C)(C)NS(=O)(=O)C)C1=CC=CC=C1.C(CCC)(OC)(OC)OC>>C1(=CC=CC=C1)C=1C=CC=2C3=C(C=NC2C1)N=C(N3CC(C)(C)NS(=O)(=O)C)CCC | [NH2:5][c:6]1[cH:7][n:8][c:9]2[cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[cH:18][cH:19][c:20]2[c:21]1[NH:22][CH2:23][C:24]([CH3:25])([CH3:26])[NH:27][S:28]([CH3:29])(=[O:30])=[O:31].CO[C:4](OC)(OC)[CH2:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]2[cH:7][n:8][c:9]3[cH:10][c:11](-[c:12]4[cH:13]... | CC(C)(CNc1c(N)cnc2cc(-c3ccccc3)ccc12)NS(C)(=O)=O.CCCC(OC)(OC)OC | CCCc1nc2cnc3cc(-c4ccccc4)ccc3c2n1CC(C)(C)NS(C)(=O)=O | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 8d87c769e65778c9400c7f523e0409ecf0ffad86543cd9fdd6ef4b239323db96 | a60e703c3cf5c0d933aa031358d338c45d96ec82dec3fc2d9f5dce06b9dcc651 | c1ccc(-c2ccc3c(c2)ncc2nc[nH]c23)cc1 | C-O-[C;H0;D4;+0:1](-O-C)(-O-C)-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1-[NH2;D1;+0:13]>>[C:4]-[C:5]-[n;H0;D3;+0:6]1:[c:7]2:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:2:[n;H0;D2;+0:13]:[c;H0;D3;+0:1]:1-[C:2]-[C:3] | 81.8 | [{"value": 81.8, "product": "C1(=CC=CC=C1)C=1C=CC=2C3=C(C=NC2C1)N=C(N3CC(C)(C)NS(=O)(=O)C)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | N-[2-(3-Amino-7-phenylquinolin-4-ylamino)-1,1-dimethylethyl]methanesulfonamide (2.20 g, 5.04 mmol) was treated with trimethyl orthobutyrate (0.90 mL, 5.5 mmol) according to the method described in Part G of Example 1. The chromatographic purification was carried out eluting with 92.5:7.5 dichloromethane:methanol to pro... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Primary amine.Secondary amine | null | c1ccc2ncccc2c1 | c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccccc1 | HO- | null | null | null | CC(C)(CNc1c(N)cnc2cc(-c3ccccc3)ccc12)NS(C)(=O)=O.CCCC(OC)(OC)OC>>CCCc1nc2cnc3cc(-c4ccccc4)ccc3c2n1CC(C)(C)NS(C)(=O)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f15ea28ffbee4c82a8f9b5a3dcec7661 | CC(C)(N)CNc1c([N+](=O)[O-])cnc2cc(-c3ccccc3)ccc12.O=C(Cl)C1CCCCC1>>C1CCCCC1.CC(C)(CNc1c([N+](=O)[O-])cnc2cc(-c3ccccc3)ccc12)NC=O | [N+](=O)([O-])C=1C=NC2=CC(=CC=C2C1NCC(C)(N)C)C1=CC=CC=C1.C(C)N(CC)CC.C1(CCCCC1)C(=O)Cl>>CC(CNC1=C(C=NC2=CC(=CC=C12)C1=CC=CC=C1)[N+](=O)[O-])(C)NC=O.C1CCCCC1 | [CH3:7][C:8]([CH3:9])([CH2:10][NH:11][c:12]1[c:13]([N+:14](=[O:15])[O-:16])[cH:17][n:18][c:19]2[cH:20][c:21](-[c:22]3[cH:23][cH:24][cH:25][cH:26][cH:27]3)[cH:28][cH:29][c:30]12)[NH2:31].Cl[C:32]([CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)=[O:33]>>[CH2:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1.[CH3:7][C:8]([CH3:9])([CH2:... | CC(C)(N)CNc1c([N+](=O)[O-])cnc2cc(-c3ccccc3)ccc12.O=C(Cl)C1CCCCC1 | C1CCCCC1.CC(C)(CNc1c([N+](=O)[O-])cnc2cc(-c3ccccc3)ccc12)NC=O | null | null | ClCCl | Acylation | OtherReaction | 8d2371177cf46fb9dc57ec883e4d22ded454c0442f6ab5d8c6007193fa4dba33 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | C1CCCCC1.c1ccc(-c2ccc3cccnc3c2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3](-[C:4]-[C:5])-[C:6]-[C:7].[C:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[NH2;D1;+0:12]>>[C:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[NH;D2;+0:12]-[CH;D2;+0:1]=[O;D1;H0:2].[C:5]-[C:4]-[CH2;D2;+0:3]-[C:6]-[C:7] | 70 | [{"value": 70.0, "product": "CC(CNC1=C(C=NC2=CC(=CC=C12)C1=CC=CC=C1)[N+](=O)[O-])(C)NC=O.C1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of N1-(3-nitro-7-phenylquinolin-4-yl)-2-methylpropane-1,2-diamine (3.56 g, 10.6 mmol) in dichloromethane (100 mL) was cooled to 0° C. Triethylamine (3.0 mL, 21 mmol) and cyclohexanecarbonyl chloride (1.55 mL, 11.6 mmol) were sequentially added. The reaction was allowed to warm to ambient temperature and stir... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | C1CCCCC1 | C1CCCCC1 | C1CCCCC1.c1ccc2ncccc2c1.c1ccccc1 | Other | ClCCl | null | 2 | CC(C)(N)CNc1c([N+](=O)[O-])cnc2cc(-c3ccccc3)ccc12.O=C(Cl)C1CCCCC1>ClCCl>C1CCCCC1.CC(C)(CNc1c([N+](=O)[O-])cnc2cc(-c3ccccc3)ccc12)NC=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9d81f920428647a890f47a570c783a86 | CC(C)(N)CNc1c([N+](=O)[O-])cnc2cc(-c3ccccc3)ccc12.O=C=NC1CCCCC1>>CC(C)(CNc1c([N+](=O)[O-])cnc2cc(-c3ccccc3)ccc12)NC(=O)NC1CCCCC1 | [N+](=O)([O-])C=1C=NC2=CC(=CC=C2C1NCC(C)(N)C)C1=CC=CC=C1.C1(CCCCC1)N=C=O>>C1(CCCCC1)NC(=O)NC(CNC1=C(C=NC2=CC(=CC=C12)C1=CC=CC=C1)[N+](=O)[O-])(C)C | [CH3:1][C:2]([CH3:3])([CH2:4][NH:5][c:6]1[c:7]([N+:8](=[O:9])[O-:10])[cH:11][n:12][c:13]2[cH:14][c:15](-[c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[cH:22][cH:23][c:24]12)[NH2:25].[C:26](=[O:27])=[N:28][CH:29]1[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]1>>[CH3:1][C:2]([CH3:3])([CH2:4][NH:5][c:6]1[c:7]([N+:8](=[O:9])[O-:10... | CC(C)(N)CNc1c([N+](=O)[O-])cnc2cc(-c3ccccc3)ccc12.O=C=NC1CCCCC1 | CC(C)(CNc1c([N+](=O)[O-])cnc2cc(-c3ccccc3)ccc12)NC(=O)NC1CCCCC1 | null | null | ClCCl | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCCNc1ccnc2cc(-c3ccccc3)ccc12)NC1CCCCC1 | [C:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[NH2;D1;+0:5].[C:6]-[C:7](-[N;H0;D2;+0:8]=[C;H0;D2;+0:9]=[O;D1;H0:10])-[C:11]>>[C:6]-[C:7](-[NH;D2;+0:8]-[C;H0;D3;+0:9](=[O;D1;H0:10])-[NH;D2;+0:5]-[C:2](-[C:1])(-[C;D1;H3:3])-[C;D1;H3:4])-[C:11] | null | [] | null | null | 3 | DAY | A solution of N1-(3-nitro-7-phenylquinolin-4-yl)-2-methylpropane-1,2-diamine (3.56 g, 10.6 mmol) in dichloromethane (100 mL) was cooled to 0° C. Cyclohexyl isocyanate (3.00 mL, 23.5 mmol) was added over the course of a day, and the reaction was stirred at ambient temperature for three days. The solvent was removed unde... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccc2ncccc2c1.c1ccccc1.C1CCCCC1 | null | ClCCl | null | 72 | CC(C)(N)CNc1c([N+](=O)[O-])cnc2cc(-c3ccccc3)ccc12.O=C=NC1CCCCC1>ClCCl>CC(C)(CNc1c([N+](=O)[O-])cnc2cc(-c3ccccc3)ccc12)NC(=O)NC1CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f0308dc5638740e99da368b42ceb3de7 | NCCCN1CCCC1=O.O=[N+]([O-])c1cnc2cc(-c3ccccc3)ccc2c1Cl>>O=C1CCCN1CCCNc1c([N+](=O)[O-])cnc2cc(-c3ccccc3)ccc12 | ClC1=C(C=NC2=CC(=CC=C12)C1=CC=CC=C1)[N+](=O)[O-].NCCCN1C(CCC1)=O>>[N+](=O)([O-])C=1C=NC2=CC(=CC=C2C1NCCCN1C(CCC1)=O)C1=CC=CC=C1 | [O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][CH2:9][NH2:10].Cl[c:11]1[c:12]([N+:13](=[O:14])[O-:15])[cH:16][n:17][c:18]2[cH:19][c:20](-[c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[cH:27][cH:28][c:29]12>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][CH2:9][NH:10][c:11]1[c:12]([N+:13](=[O:14])[O-:15])[cH... | NCCCN1CCCC1=O.O=[N+]([O-])c1cnc2cc(-c3ccccc3)ccc2c1Cl | O=C1CCCN1CCCNc1c([N+](=O)[O-])cnc2cc(-c3ccccc3)ccc12 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 45e8470a78418ade39424f40732aa5ecf6717a7e5d47830a67429c5970ebd551 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C1CCCN1CCCNc1ccnc2cc(-c3ccccc3)ccc12 | Cl-[c;H0;D3;+0:1]1:[c:2](-[#7;+:3]):[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[#7;+:3]-[c:2]1:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8](:[c:9]):[c;H0;D3;+0:1]:1-[NH;D2;+0:12]-[C:11]-[C:10] | 88.1 | [{"value": 88.1, "product": "[N+](=O)([O-])C=1C=NC2=CC(=CC=C2C1NCCCN1C(CCC1)=O)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Chloro-3-nitro-7-phenylquinoline (3.51 g, 12.3 mmol) was treated with 1-(3-aminopropyl)pyrrolidin-2-one (2.3 mL, 16 mmol) according to the method described in Part E of Example 1 to provide 4.23 g of 1-[3-(3-nitro-7-phenylquinolin-4-ylamino)propyl]pyrrolidin-2-one as a yellow solid.
Conditions: See reaction.notes.pro... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | C1CC[NH]C1.c1ccc2ncccc2c1.c1ccccc1 | HCl | null | null | null | NCCCN1CCCC1=O.O=[N+]([O-])c1cnc2cc(-c3ccccc3)ccc2c1Cl>>O=C1CCCN1CCCNc1c([N+](=O)[O-])cnc2cc(-c3ccccc3)ccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f18f803e88054fb58ebacb523833a126 | CCOCC(=O)Cl.Nc1cnc2cc(-c3ccccc3)ccc2c1NCCCN1CCCC1=O>>CCOCc1nc2cnc3cc(-c4ccccc4)ccc3c2n1CCCN1CCCC1=O | NC=1C=NC2=CC(=CC=C2C1NCCCN1C(CCC1)=O)C1=CC=CC=C1.C(C)OCC(=O)Cl.C(C)N(CC)CC>>C(C)OCC=1N(C2=C(C=NC=3C=C(C=CC23)C2=CC=CC=C2)N1)CCCN1C(CCC1)=O | O=[C:5](Cl)[CH2:4][O:3][CH2:2][CH3:1].[NH2:6][c:7]1[cH:8][n:9][c:10]2[cH:11][c:12](-[c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19][cH:20][c:21]2[c:22]1[NH:23][CH2:24][CH2:25][CH2:26][N:27]1[CH2:28][CH2:29][CH2:30][C:31]1=[O:32]>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:9][c:10]3[cH:11][c:12](-[c:13]4[cH... | CCOCC(=O)Cl.Nc1cnc2cc(-c3ccccc3)ccc2c1NCCCN1CCCC1=O | CCOCc1nc2cnc3cc(-c4ccccc4)ccc3c2n1CCCN1CCCC1=O | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 101a087a520f159c722ba3d78ed38f5c3c1cf154206e5edbeb1e6397c929560f | 56ef83dfadec35a1cf1db968b807e178cc4924ce15bf36d774883783cef0f450 | O=C1CCCN1CCCn1cnc2cnc3cc(-c4ccccc4)ccc3c21 | Cl-[C;H0;D3;+0:1](=O)-[C:2]-[#8:3].[C:4]-[C:5]-[NH;D2;+0:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1-[NH2;D1;+0:13]>>[#8:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:13]:[c:12]2:[c:11]:[#7;a:10]:[c:9]:[c:8]:[c:7]:2:[n;H0;D3;+0:6]:1-[C:5]-[C:4] | 56.7 | [{"value": 56.7, "product": "C(C)OCC=1N(C2=C(C=NC=3C=C(C=CC23)C2=CC=CC=C2)N1)CCCN1C(CCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-[3-(3-Amino-7-phenylquinolin-4-ylamino)propyl]pyrrolidin-2-one (2.21 g, 6.13 mmol) was treated with ethoxyacetyl chloride (0.95 mL, 8.76 mmol) according to the methods described in Parts C and D of Examples 152–156. Triethylamine (8.6 mmol) was added in Part C. The product from Part D was purified by column chromatog... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine.Secondary amine | null | c1ccc2ncccc2c1 | c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccccc1.C1CC[NH]C1 | HCl | null | null | null | CCOCC(=O)Cl.Nc1cnc2cc(-c3ccccc3)ccc2c1NCCCN1CCCC1=O>>CCOCc1nc2cnc3cc(-c4ccccc4)ccc3c2n1CCCN1CCCC1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-26d6796ecf234855b1356d51dc24084a | COCCC(=O)Cl.Nc1cnc2cc(-c3ccccc3)ccc2c1NCCCN1CCCC1=O>>COCCc1nc2cnc3cc(-c4ccccc4)ccc3c2n1CCCN1CCCC1=O | NC=1C=NC2=CC(=CC=C2C1NCCCN1C(CCC1)=O)C1=CC=CC=C1.COCCC(=O)Cl>>COCCC=1N(C2=C(C=NC=3C=C(C=CC23)C2=CC=CC=C2)N1)CCCN1C(CCC1)=O | O=[C:5](Cl)[CH2:4][CH2:3][O:2][CH3:1].[NH2:6][c:7]1[cH:8][n:9][c:10]2[cH:11][c:12](-[c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19][cH:20][c:21]2[c:22]1[NH:23][CH2:24][CH2:25][CH2:26][N:27]1[CH2:28][CH2:29][CH2:30][C:31]1=[O:32]>>[CH3:1][O:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:9][c:10]3[cH:11][c:12](-[c:13]4[cH... | COCCC(=O)Cl.Nc1cnc2cc(-c3ccccc3)ccc2c1NCCCN1CCCC1=O | COCCc1nc2cnc3cc(-c4ccccc4)ccc3c2n1CCCN1CCCC1=O | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 101a087a520f159c722ba3d78ed38f5c3c1cf154206e5edbeb1e6397c929560f | 56ef83dfadec35a1cf1db968b807e178cc4924ce15bf36d774883783cef0f450 | O=C1CCCN1CCCn1cnc2cnc3cc(-c4ccccc4)ccc3c21 | Cl-[C;H0;D3;+0:1](=O)-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1-[NH2;D1;+0:13]>>[C:4]-[C:5]-[n;H0;D3;+0:6]1:[c:7]2:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:2:[n;H0;D2;+0:13]:[c;H0;D3;+0:1]:1-[C:2]-[C:3] | null | [] | null | null | null | null | The methods described in Parts A of Example 204 were used to treat 1-[3-(3-amino-7-phenylquinolin-4-ylamino)propyl]pyrrolidin-2-one (1.19 g, 3.30 mmol) with 3-methoxypropionyl chloride (0.45 mL, 4.1 mmol) to afford 1-{3-[2-(2-methoxyethyl)-7-phenyl-1H-imidazo[4,5-c]quinolin-1-yl]propyl}pyrrolidin-2-one, which was oxidi... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine.Secondary amine | null | c1ccc2ncccc2c1 | c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccccc1.C1CC[NH]C1 | HCl | null | null | null | COCCC(=O)Cl.Nc1cnc2cc(-c3ccccc3)ccc2c1NCCCN1CCCC1=O>>COCCc1nc2cnc3cc(-c4ccccc4)ccc3c2n1CCCN1CCCC1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4e57e73174c846a0ad0b36fef32f9e8b | C=CS(C)(=O)=O.CCOCc1nc2cnc3cc(Br)ccc3c2n1CC(C)(C)O>>CCOCc1nc2cnc3cc(Br)ccc3c2n1CC(C)(C)OCCS(C)(=O)=O | O.C(=C)S(=O)(=O)C.BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CC(C)(O)C)COCC.[H-].[Na+]>>BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CC(C)(C)OCCS(=O)(=O)C)COCC | [CH2:24]=[CH:25][S:26]([CH3:27])(=[O:28])=[O:29].[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]3[c:17]2[n:18]1[CH2:19][C:20]([CH3:21])([CH3:22])[OH:23]>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]3[c:17]... | C=CS(C)(=O)=O.CCOCc1nc2cnc3cc(Br)ccc3c2n1CC(C)(C)O | CCOCc1nc2cnc3cc(Br)ccc3c2n1CC(C)(C)OCCS(C)(=O)=O | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | oxa-Michael addition | 714eaa0e6de1d85d58a88133b4d5e95857344ec278e90cde0496674a55b79739 | ea8641c928da9fe5f2bca5bb859dbb223e9e99eefdf70a15450fd2e768112e0a | c1ccc2c(c1)ncc1nc[nH]c12 | [C;D1;H3:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[CH;D2;+0:5]=[CH2;D1;+0:6].[C:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[OH;D1;+0:11]>>[C:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[O;H0;D2;+0:11]-[CH2;D2;+0:6]-[CH2;D2;+0:5]-[#16:2](-[C;D1;H3:1])(=[O;D1;H0:3])=[O;D1;H0:4] | null | [] | null | null | 70 | MINUTE | A solution of methyl vinyl sulfone (3.0 g, 29 mmol) and 1-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol (5.4 g, 14 mmol) in anhydrous THF (57 mL) was purged with nitrogen; solid sodium hydride (available as a 60% dispersion in mineral oil, 57 mg, 1.4 mmol) was added. The reaction was stirr... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol.Vinyl | Ether | null | null | c1ccc2c(c1)ncc1[nH]cnc12 | null | C1CCOC1 | null | 1.166667 | C=CS(C)(=O)=O.CCOCc1nc2cnc3cc(Br)ccc3c2n1CC(C)(C)O>C1CCOC1>CCOCc1nc2cnc3cc(Br)ccc3c2n1CC(C)(C)OCCS(C)(=O)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4e9c85fdd7b549379978a18932e2d098 | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CC(C)(C)OCCS(C)(=O)=O.c1cncc(B2OCCCO2)c1>>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC(C)(C)OCCS(C)(=O)=O | BrC=1C=CC=2C3=C(C(=NC2C1)N)N=C(N3CC(C)(C)OCCS(=O)(=O)C)COCC.B1(OCCCO1)C2=CN=CC=C2>>C(C)OCC=1N(C2=C(C(=NC=3C=C(C=CC23)C=2C=NC=CC2)N)N1)CC(C)(C)OCCS(=O)(=O)C | Br[c:13]1[cH:12][c:11]2[n:10][c:8]([NH2:9])[c:7]3[n:6][c:5]([CH2:4][O:3][CH2:2][CH3:1])[n:24]([CH2:25][C:26]([CH3:27])([CH3:28])[O:29][CH2:30][CH2:31][S:32]([CH3:33])(=[O:34])=[O:35])[c:23]3[c:22]2[cH:21][cH:20]1.C1COB([c:14]2[cH:15][cH:16][cH:17][n:18][cH:19]2)OC1>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2... | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CC(C)(C)OCCS(C)(=O)=O.c1cncc(B2OCCCO2)c1 | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC(C)(C)OCCS(C)(=O)=O | null | null | null | C-C Coupling | Suzuki coupling with boronic esters | 2cd1cbe6f17c98cb5223a75d20dfc144a6eae8461c4fe8a7e9cc4bc7ecadb166 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1cncc(-c2ccc3c(c2)ncc2nc[nH]c23)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[c:6](:[#7;a:7]):[c:8](:[#7;a:9]):[c:10]:2:[c:11]:[c:12]:1.C1-C-O-B(-[c;H0;D3;+0:13]2:[c:14]:[c:15]:[c:16]:[#7;a:17]:[c:18]:2)-O-C-1>>[#7;a:9]:[c:8]1:[c:10]2:[c:11]:[c:12]:[c;H0;D3;+0:1](-[c;H0;D3;+0:13]3:[c:14]:[c:15]:[c:16]:[#7;a:17]:[c:18]:3):[c:2]:[c:3]:2:[#7;a:4]:[c:5... | 58.6 | [{"value": 58.6, "product": "C(C)OCC=1N(C2=C(C(=NC=3C=C(C=CC23)C=2C=NC=CC2)N)N1)CC(C)(C)OCCS(=O)(=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 7-Bromo-2-ethoxymethyl-1-{2-[2-(methanesulfonyl)ethoxy]-2-methylpropyl}-1H-imidazo[4,5-c]quinolin-4-amine (1.2 g, 2.4 mmol) and pyridine-3-boronic acid 1,3-propanediol cyclic ester (0.47 g, 2.9 mmol) were coupled according to the method described in Part J of Example 1. The work-up procedure used in Part F of Examples ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2c(c1)ncc1[nH]cnc12.B1OCCCO1.c1ccncc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1 | HBr.B | null | null | null | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CC(C)(C)OCCS(C)(=O)=O.c1cncc(B2OCCCO2)c1>>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC(C)(C)OCCS(C)(=O)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-27596081b9574913b377010ca438e260 | NCCCCO.O=[N+]([O-])c1cnc2cc(Br)ccc2c1Cl>>O=[N+]([O-])c1cnc2cc(Br)ccc2c1NCCCCO | BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])Cl.NCCCCO.NCCCCO>>BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])NCCCCO | [NH2:15][CH2:16][CH2:17][CH2:18][CH2:19][OH:20].Cl[c:14]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][n:6][c:7]2[cH:8][c:9]([Br:10])[cH:11][cH:12][c:13]21>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][n:6][c:7]2[cH:8][c:9]([Br:10])[cH:11][cH:12][c:13]2[c:14]1[NH:15][CH2:16][CH2:17][CH2:18][CH2:19][OH:20] | NCCCCO.O=[N+]([O-])c1cnc2cc(Br)ccc2c1Cl | O=[N+]([O-])c1cnc2cc(Br)ccc2c1NCCCCO | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 45e8470a78418ade39424f40732aa5ecf6717a7e5d47830a67429c5970ebd551 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc2ncccc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]:[c:8]:1-[#7;+:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[#7;+:9]-[c:8]1:[c:7]:[#7;a:6]:[c:4](:[c:5]):[c:2](:[c:3]):[c;H0;D3;+0:1]:1-[NH;D2;+0:12]-[C:11]-[C:10] | 89.1 | [{"value": 89.1, "product": "BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])NCCCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A modification of the method described in Part E of Example 1 was used to treat 7-bromo-4-chloro-3-nitroquinoline (20.0 g, 69.6 mmol) with 4-amino-1-butanol (6.9 mL, 76.5 mmol). The addition of 4-amino-1-butanol was carried out at ambient temperature. The product, 4-(7-bromo-3-nitroquinolin-4-ylamino)butan-1-ol (21.1 g... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HCl | null | null | null | NCCCCO.O=[N+]([O-])c1cnc2cc(Br)ccc2c1Cl>>O=[N+]([O-])c1cnc2cc(Br)ccc2c1NCCCCO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b222e38a54a5496bb7a0423bbddccd3a | O=S(Cl)Cl.O=[N+]([O-])c1cnc2cc(Br)ccc2c1NCCCCO>>O=[N+]([O-])c1cnc2cc(Br)ccc2c1NCCCCCl | S(=O)(Cl)Cl.S(=O)(Cl)Cl.BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])NCCCCO.C([O-])(O)=O.[Na+]>>BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])NCCCCCl | O=S(Cl)[Cl:20].O[CH2:19][CH2:18][CH2:17][CH2:16][NH:15][c:14]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][n:6][c:7]2[cH:8][c:9]([Br:10])[cH:11][cH:12][c:13]21>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][n:6][c:7]2[cH:8][c:9]([Br:10])[cH:11][cH:12][c:13]2[c:14]1[NH:15][CH2:16][CH2:17][CH2:18][CH2:19][Cl:20] | O=S(Cl)Cl.O=[N+]([O-])c1cnc2cc(Br)ccc2c1NCCCCO | O=[N+]([O-])c1cnc2cc(Br)ccc2c1NCCCCCl | null | null | ClCCl | Functional Group Interconversion | Alcohol to chloride_SOCl2 | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | c1ccc2ncccc2c1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[CH2;D2;+0:2]-[C:3]-[C:4]>>[C:4]-[C:3]-[CH2;D2;+0:2]-[Cl;H0;D1;+0:1] | 37.9 | [{"value": 37.9, "product": "BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])NCCCCCl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 5 | MINUTE | A suspension of 4-(7-bromo-3-nitroquinolin-4-ylamino)butan-1-ol (20.75 g, 61.0 mmol) in dichloromethane (220 mL) was cooled to 0° C.; thionyl chloride (4.90 mL, 67.1 mmol) was added dropwise over a period of ten minutes. The reaction was stirred at 0° C. for five minutes, allowed to warm to ambient temperature, and sti... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccc2ncccc2c1 | HCl | ClCCl | 0 | 0.083333 | O=S(Cl)Cl.O=[N+]([O-])c1cnc2cc(Br)ccc2c1NCCCCO>ClCCl>O=[N+]([O-])c1cnc2cc(Br)ccc2c1NCCCCCl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-440122c60b11499ca2604e0ffa81145b | O=[N+]([O-])c1cnc2cc(Br)ccc2c1NCCCCCl>>Nc1cnc2cc(Br)ccc2c1NCCCCCl | BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])NCCCCCl.S(=O)([O-])S(=O)[O-].[Na+].[Na+]>>BrC1=CC=C2C(=C(C=NC2=C1)N)NCCCCCl | O=[N+:1]([O-])[c:2]1[cH:3][n:4][c:5]2[cH:6][c:7]([Br:8])[cH:9][cH:10][c:11]2[c:12]1[NH:13][CH2:14][CH2:15][CH2:16][CH2:17][Cl:18]>>[NH2:1][c:2]1[cH:3][n:4][c:5]2[cH:6][c:7]([Br:8])[cH:9][cH:10][c:11]2[c:12]1[NH:13][CH2:14][CH2:15][CH2:16][CH2:17][Cl:18] | O=[N+]([O-])c1cnc2cc(Br)ccc2c1NCCCCCl | Nc1cnc2cc(Br)ccc2c1NCCCCCl | null | null | CO.O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2ncccc2c1 | 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] | 98 | [{"value": 98.0, "product": "BrC1=CC=C2C(=C(C=NC2=C1)N)NCCCCCl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | A suspension of (7-bromo-3-nitroquinolin-4-yl)-(4-chlorobutyl)amine (8.05 g, 22.5 mmol) in methanol (250 mL) was cooled to 0° C.; a solution of sodium hydrosulfite (19.5 g, 112 mmol) in water (80 mL) was added dropwise over a period of 30 minutes. The reaction was stirred at ambient temperature for two hours and then c... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2ncccc2c1 | Other | CO.O | 0 | 2 | O=[N+]([O-])c1cnc2cc(Br)ccc2c1NCCCCCl>CO.O>Nc1cnc2cc(Br)ccc2c1NCCCCCl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5addcc65777f49a1b27a679dec305ec4 | CCOCC(=O)Cl.Nc1cnc2cc(Br)ccc2c1NCCCCCl>>CCOCC(=O)Nc1cnc2cc(Br)ccc2c1NCCCCCl.Cl | BrC1=CC=C2C(=C(C=NC2=C1)N)NCCCCCl.C(C)OCC(=O)Cl>>Cl.BrC1=CC=C2C(=C(C=NC2=C1)NC(COCC)=O)NCCCCCl | [CH3:1][CH2:2][O:3][CH2:4][C:5](=[O:6])[Cl:25].[NH2:7][c:8]1[cH:9][n:10][c:11]2[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]2[c:18]1[NH:19][CH2:20][CH2:21][CH2:22][CH2:23][Cl:24]>>[CH3:1][CH2:2][O:3][CH2:4][C:5](=[O:6])[NH:7][c:8]1[cH:9][n:10][c:11]2[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]2[c:18]1[NH:19][CH2:20][CH2:21]... | CCOCC(=O)Cl.Nc1cnc2cc(Br)ccc2c1NCCCCCl | CCOCC(=O)Nc1cnc2cc(Br)ccc2c1NCCCCCl.Cl | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc2ncccc2c1 | [#8:1]-[C:2]-[C;H0;D3;+0:3](-[Cl;H0;D1;+0:4])=[O;D1;H0:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]:[c:11]>>[#8:1]-[C:2]-[C;H0;D3;+0:3](=[O;D1;H0:5])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]:[c:11].[ClH;D0;+0:4] | null | [] | null | null | 1 | HOUR | A modification of the method described in Part C of Examples 125–135 was used to treat 7-bromo-N4-(4-chlorobutyl)quinoline-3,4-diamine (7.25 g, 22.1 mmol) with ethoxyacetyl chloride (2.76 mL, 24.3 mmol). After the reaction was stirred for one hour, it was concentrated under reduced pressure to provide N-[7-bromo-4-(4-c... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2ncccc2c1 | null | null | null | 1 | CCOCC(=O)Cl.Nc1cnc2cc(Br)ccc2c1NCCCCCl>>CCOCC(=O)Nc1cnc2cc(Br)ccc2c1NCCCCCl.Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b29e7842b37f4e659459e8c871f8b783 | CC([O-])=S.CCOCc1nc2cnc3cc(Br)ccc3c2n1CCCCCl>>CCOCc1nc2cnc3cc(Br)ccc3c2n1CCCCSC(C)=O | C(C)(=S)[O-].[K+].BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CCCCCl)COCC>>BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CCCCSC(C)=O)COCC | [S:23]=[C:24]([CH3:25])[O-:26].Cl[CH2:22][CH2:21][CH2:20][CH2:19][n:18]1[c:5]([CH2:4][O:3][CH2:2][CH3:1])[n:6][c:7]2[cH:8][n:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]3[c:17]21>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]3[c:17]2[n:18]1[CH2:19][CH2:20... | CC([O-])=S.CCOCc1nc2cnc3cc(Br)ccc3c2n1CCCCCl | CCOCc1nc2cnc3cc(Br)ccc3c2n1CCCCSC(C)=O | null | null | CN(C)C=O | Acylation | OtherReaction | 1f876542c8a2de0f0c93c1e55257e1922650fd69ea48617e41a961445109d4b2 | 00ab4047825d93b84a3dc255ab210414ba88fbe19a5ef7a3657605acca13230b | c1ccc2c(c1)ncc1nc[nH]c12 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[C;H0;D3;+0:5](-[O-;H0;D1:6])=[S;H0;D1;+0:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:7]-[C;H0;D3;+0:5](-[C;D1;H3:4])=[O;H0;D1;+0:6] | 103.4 | [{"value": 103.4, "product": "BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CCCCSC(C)=O)COCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 21 | HOUR | Potassium thioacetate (1.70 g, 14.9 mmol) was added in one portion to a stirred solution of 7-bromo-1-(4-chlorobutyl)-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline (5.37 g, 13.5 mmol) in DMF (65 mL), and the reaction was stirred at ambient temperature for 21 hours. The DMF was removed under reduced pressure, and the residu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Thiocarbonyl | Carbo-thioester | null | null | c1ccc2c(c1)ncc1[nH]cnc12 | Other | CN(C)C=O | null | 21 | CC([O-])=S.CCOCc1nc2cnc3cc(Br)ccc3c2n1CCCCCl>CN(C)C=O>CCOCc1nc2cnc3cc(Br)ccc3c2n1CCCCSC(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-01d1ddd9c69b40269354404d79ae9fd0 | CCOCc1nc2cnc3cc(Br)ccc3c2n1CCCCSC(C)=O>>CCOCc1nc2cnc3cc(Br)ccc3c2n1CCCCS | BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CCCCSC(C)=O)COCC.C[O-].[Na+]>>BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CCCCS)COCC | CC(=O)[S:23][CH2:22][CH2:21][CH2:20][CH2:19][n:18]1[c:5]([CH2:4][O:3][CH2:2][CH3:1])[n:6][c:7]2[cH:8][n:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]3[c:17]21>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]3[c:17]2[n:18]1[CH2:19][CH2:20][CH2:21][CH2:22][SH:... | CCOCc1nc2cnc3cc(Br)ccc3c2n1CCCCSC(C)=O | CCOCc1nc2cnc3cc(Br)ccc3c2n1CCCCS | null | null | CO | Reduction | OtherReaction | 7702cd666d5d9a9f1bdea3600e3b84cc62dd11d3f2cea261702317a39db4e581 | 18d802456fe85193570fdb3a00b25c8956a03b5a0210f708f961e42c1669d76e | c1ccc2c(c1)ncc1nc[nH]c12 | C-C(=O)-[S;H0;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[SH;D1;+0:1] | 99.3 | [{"value": 99.3, "product": "BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CCCCS)COCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Nitrogen was bubbled through a solution of thioacetic acid S-[4-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]ester (1.93 g, 4.42 mmol) in methanol (45 mL), and then sodium methoxide (2.5 mL of 25% by weight in methanol, 11.1 mmol) was added dropwise over a period of three minutes. The yellow solution wa... | 10.6084/m9.figshare.5104873.v1 | null | Carbo-thioester | Aliphatic thiol | null | null | c1ccc2c(c1)ncc1[nH]cnc12 | HO- | CO | null | 1 | CCOCc1nc2cnc3cc(Br)ccc3c2n1CCCCSC(C)=O>CO>CCOCc1nc2cnc3cc(Br)ccc3c2n1CCCCS |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-83171146c9b84b97aff0b1aa7d924e60 | CCOCc1nc2cnc3cc(Br)ccc3c2n1CCCC(C)(C)S(N)(=O)=O.[NH4+]>>CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCC(C)(C)S(N)(=O)=O | ClC=1C=C(C(=O)OO)C=CC1.CC(CCCN1C(=NC=2C=NC=3C=C(C=CC3C21)Br)COCC)(S(=O)(=O)N)C.[OH-].[NH4+].C1(=CC=C(C=C1)S(=O)(=O)Cl)C>>CC(CCCN1C(=NC=2C(=NC=3C=C(C=CC3C21)Br)N)COCC)(S(=O)(=O)N)C | [CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:10][c:11]3[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]3[c:18]2[n:19]1[CH2:20][CH2:21][CH2:22][C:23]([CH3:24])([CH3:25])[S:26]([NH2:27])(=[O:28])=[O:29].[NH4+:9]>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13]([Br:14])[cH:15][cH:16][c... | CCOCc1nc2cnc3cc(Br)ccc3c2n1CCCC(C)(C)S(N)(=O)=O.[NH4+] | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCC(C)(C)S(N)(=O)=O | null | null | ClCCl.C(Cl)(Cl)Cl | Functional Group Addition | OtherReaction | dc63235befaaf41df35292b6862b726098d8e1b79a2cef881f35b7cf9ff16606 | d69ce1fde4173969963123914389bef807fad83b73b8a587195a7122d5cdf1d2 | c1ccc2c(c1)ncc1nc[nH]c12 | [C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[cH;D2;+0:6]:[#7;a:7]:[c:8]:[c:9]:[c:10]:1:2.[NH4+;D0:11]>>[C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[c:10]:1:[c:9]:[c:8]:[#7;a:7]:[c;H0;D3;+0:6]:2-[NH2;D1;+0:11] | null | [] | null | null | 2 | HOUR | 3-Chloroperoxybenzoic acid (0.126 g of 70% pure material, 0.73 mmol) was added in one portion to a stirred solution of dimethyl 4-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butane-1-sulfonamide (0.30 g, 0.63 mmol) in chloroform (7 mL), and the solution was stirred for two hours at ambient temperature. Ammon... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary amine | c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12 | null | ClCCl.C(Cl)(Cl)Cl | null | 2 | CCOCc1nc2cnc3cc(Br)ccc3c2n1CCCC(C)(C)S(N)(=O)=O.[NH4+]>ClCCl.C(Cl)(Cl)Cl>CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCC(C)(C)S(N)(=O)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a616420e3c0545a6852c5145c960a6c0 | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCC(C)(C)S(N)(=O)=O.OB(O)c1ccccc1>>CCOCc1nc2c(N)nc3cc(-c4ccccc4)ccc3c2n1CCCC(C)(C)S(N)(=O)=O | CC(CCCN1C(=NC=2C(=NC=3C=C(C=CC3C21)Br)N)COCC)(S(=O)(=O)N)C.C1(=CC=CC=C1)B(O)O>>CC(CCCN1C(=NC=2C(=NC=3C=C(C=CC3C21)C2=CC=CC=C2)N)COCC)(S(=O)(=O)N)C | Br[c:13]1[cH:12][c:11]2[n:10][c:8]([NH2:9])[c:7]3[n:6][c:5]([CH2:4][O:3][CH2:2][CH3:1])[n:24]([CH2:25][CH2:26][CH2:27][C:28]([CH3:29])([CH3:30])[S:31]([NH2:32])(=[O:33])=[O:34])[c:23]3[c:22]2[cH:21][cH:20]1.OB(O)[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10]... | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCC(C)(C)S(N)(=O)=O.OB(O)c1ccccc1 | CCOCc1nc2c(N)nc3cc(-c4ccccc4)ccc3c2n1CCCC(C)(C)S(N)(=O)=O | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 89ee2e97ba79660eddf3dfa788334e60a83082a3d4afa6ed050c5f1f85789150 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc3c(c2)ncc2nc[nH]c23)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[c:6](:[#7;a:7]):[c:8](:[#7;a:9]):[c:10]:2:[c:11]:[c:12]:1.O-B(-O)-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16]:[c:17]>>[#7;a:9]:[c:8]1:[c:10]2:[c:11]:[c:12]:[c;H0;D3;+0:1](-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16]:[c:17]):[c:2]:[c:3]:2:[#7;a:4]:[c:5]:[c:6]:1:[#7;a:7] | 20.8 | [{"value": 20.8, "product": "CC(CCCN1C(=NC=2C(=NC=3C=C(C=CC3C21)C2=CC=CC=C2)N)COCC)(S(=O)(=O)N)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Dimethyl 4-(4-amino-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butane-1-sulfonamide (0.66 g, 1.4 mmol) and phenyl boronic acid (0.20 g, 1.6 mmol) were coupled according to the method described in Part J of Example 1. The reaction was heated at reflux for 14 hours, and the work-up procedure used in Part F of ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)ncc1[nH]cnc12.c1ccccc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccccc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccccc1 | HBr.B | null | null | null | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCC(C)(C)S(N)(=O)=O.OB(O)c1ccccc1>>CCOCc1nc2c(N)nc3cc(-c4ccccc4)ccc3c2n1CCCC(C)(C)S(N)(=O)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-600bf3d103d74d4c8b6ec0893592398f | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCC(Cc1ccc(OC)cc1)S(N)(=O)=O.OB(O)c1cccnc1>>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCCC(Cc1ccc(OC)cc1)S(N)(=O)=O | COC1=CC=C(CC(CCCN2C(=NC=3C(=NC=4C=C(C=CC4C32)Br)N)COCC)S(=O)(=O)N)C=C1.N1=CC(=CC=C1)B(O)O.N1=CC(=CC=C1)B(O)O>>COC1=CC=C(CC(CCCN2C(=NC=3C(=NC=4C=C(C=CC4C32)C=3C=NC=CC3)N)COCC)S(=O)(=O)N)C=C1 | Br[c:13]1[cH:12][c:11]2[n:10][c:8]([NH2:9])[c:7]3[n:6][c:5]([CH2:4][O:3][CH2:2][CH3:1])[n:24]([CH2:25][CH2:26][CH2:27][CH:28]([CH2:29][c:30]4[cH:31][cH:32][c:33]([O:34][CH3:35])[cH:36][cH:37]4)[S:38]([NH2:39])(=[O:40])=[O:41])[c:23]3[c:22]2[cH:21][cH:20]1.OB(O)[c:14]1[cH:15][cH:16][cH:17][n:18][cH:19]1>>[CH3:1][CH2:2][... | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCC(Cc1ccc(OC)cc1)S(N)(=O)=O.OB(O)c1cccnc1 | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCCC(Cc1ccc(OC)cc1)S(N)(=O)=O | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | d23a08b59b246d837a860414fc085402a8d785d2b981e3447d503da913f098ed | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(CCCCCn2cnc3cnc4cc(-c5cccnc5)ccc4c32)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[c:6](:[#7;a:7]):[c:8](:[#7;a:9]):[c:10]:2:[c:11]:[c:12]:1.O-B(-O)-[c;H0;D3;+0:13]1:[c:14]:[c:15]:[c:16]:[#7;a:17]:[c:18]:1>>[#7;a:9]:[c:8]1:[c:10]2:[c:11]:[c:12]:[c;H0;D3;+0:1](-[c;H0;D3;+0:13]3:[c:14]:[c:15]:[c:16]:[#7;a:17]:[c:18]:3):[c:2]:[c:3]:2:[#7;a:4]:[c:5]:[c:6]:1... | 53.9 | [{"value": 53.9, "product": "COC1=CC=C(CC(CCCN2C(=NC=3C(=NC=4C=C(C=CC4C32)C=3C=NC=CC3)N)COCC)S(=O)(=O)N)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Methoxybenzyl 4-(4-amino-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butane-1-sulfonamide (1.16 g, 2.0 mmol) and pyridine-3-boronic acid (0.30 g, 2.4 mmol) were coupled according to the method described in Part J of Example 1. The reaction was heated at reflux for 14 hours, at which time additional pyridine... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1.c1ccccc1 | HBr.B | null | null | null | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCC(Cc1ccc(OC)cc1)S(N)(=O)=O.OB(O)c1cccnc1>>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCCC(Cc1ccc(OC)cc1)S(N)(=O)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-24b232e9b29f4e4097636a3ef525cd72 | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCCC(Cc1ccc(OC)cc1)S(N)(=O)=O>>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCCCS(N)(=O)=O | COC1=CC=C(CC(CCCN2C(=NC=3C(=NC=4C=C(C=CC4C32)C=3C=NC=CC3)N)COCC)S(=O)(=O)N)C=C1>>NC1=NC=2C=C(C=CC2C2=C1N=C(N2CCCCS(=O)(=O)N)COCC)C=2C=NC=CC2 | COc1ccc(C[CH:28]([CH2:27][CH2:26][CH2:25][n:24]2[c:5]([CH2:4][O:3][CH2:2][CH3:1])[n:6][c:7]3[c:8]([NH2:9])[n:10][c:11]4[cH:12][c:13](-[c:14]5[cH:15][cH:16][cH:17][n:18][cH:19]5)[cH:20][cH:21][c:22]4[c:23]32)[S:29]([NH2:30])(=[O:31])=[O:32])cc1>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:1... | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCCC(Cc1ccc(OC)cc1)S(N)(=O)=O | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCCCS(N)(=O)=O | null | null | FC(C(=O)O)(F)F | Reduction | OtherReaction | 37db49c452d6ff08df3eff3ac1188585096100b032f2fef99660b7108114c4fd | 84394d34c591024a84d9393eb3e8adb8ada5a6225c3abafc4dae9aedd4568be4 | c1cncc(-c2ccc3c(c2)ncc2nc[nH]c23)c1 | C-O-c1:c:c:c(-C-[CH;D3;+0:1](-[C:2]-[C:3])-[#16:4](-[N;D1;H2:5])(=[O;D1;H0:6])=[O;D1;H0:7]):c:c:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[#16:4](-[N;D1;H2:5])(=[O;D1;H0:6])=[O;D1;H0:7] | 77.5 | [{"value": 77.5, "product": "NC1=NC=2C=C(C=CC2C2=C1N=C(N2CCCCS(=O)(=O)N)COCC)C=2C=NC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of 4-methoxybenzyl 4-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]butane-1-sulfonamide (0.50 g, 0.88 mmol) in trifluoroacetic acid (5 mL) was stirred at ambient temperature for four hours and then concentrated under reduced pressure. The residue was dissolved in methanol and concen... | 10.6084/m9.figshare.5104873.v1 | null | Ether | null | c1ccccc1 | null | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1 | HO- | FC(C(=O)O)(F)F | null | 0.5 | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCCC(Cc1ccc(OC)cc1)S(N)(=O)=O>FC(C(=O)O)(F)F>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCCCS(N)(=O)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-db20c0a683854d36b57eabfee6614a32 | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCC(C)S(N)(=O)=O.c1cncc(B2OCCCO2)c1>>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCCC(C)S(N)(=O)=O | CC(CCCN1C(=NC=2C(=NC=3C=C(C=CC3C21)Br)N)COCC)S(=O)(=O)N.B1(OCCCO1)C2=CN=CC=C2.B1(OCCCO1)C2=CN=CC=C2.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>CC(CCCN1C(=NC=2C(=NC=3C=C(C=CC3C21)C=2C=NC=CC2)N)COCC)S(=O)(=O)N | Br[c:13]1[cH:12][c:11]2[n:10][c:8]([NH2:9])[c:7]3[n:6][c:5]([CH2:4][O:3][CH2:2][CH3:1])[n:24]([CH2:25][CH2:26][CH2:27][CH:28]([CH3:29])[S:30]([NH2:31])(=[O:32])=[O:33])[c:23]3[c:22]2[cH:21][cH:20]1.C1COB([c:14]2[cH:15][cH:16][cH:17][n:18][cH:19]2)OC1>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11... | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCC(C)S(N)(=O)=O.c1cncc(B2OCCCO2)c1 | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCCC(C)S(N)(=O)=O | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | null | C-C Coupling | Suzuki coupling with boronic esters | 2cd1cbe6f17c98cb5223a75d20dfc144a6eae8461c4fe8a7e9cc4bc7ecadb166 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1cncc(-c2ccc3c(c2)ncc2nc[nH]c23)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[c:6](:[#7;a:7]):[c:8](:[#7;a:9]):[c:10]:2:[c:11]:[c:12]:1.C1-C-O-B(-[c;H0;D3;+0:13]2:[c:14]:[c:15]:[c:16]:[#7;a:17]:[c:18]:2)-O-C-1>>[#7;a:9]:[c:8]1:[c:10]2:[c:11]:[c:12]:[c;H0;D3;+0:1](-[c;H0;D3;+0:13]3:[c:14]:[c:15]:[c:16]:[#7;a:17]:[c:18]:3):[c:2]:[c:3]:2:[#7;a:4]:[c:5... | 97.9 | [{"value": 97.9, "product": "CC(CCCN1C(=NC=2C(=NC=3C=C(C=CC3C21)C=2C=NC=CC2)N)COCC)S(=O)(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Methyl 4-(4-amino-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butane-1-sulfonamide (0.78 g, 1.7 mmol) and pyridine-3-boronic acid 1,3-propanediol cyclic ester (0.33 g, 2.0 mmol) were coupled according to the method described in Part J of Example 1. The reaction was heated at reflux for 15 hours, at which time... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2c(c1)ncc1[nH]cnc12.B1OCCCO1.c1ccncc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1 | HBr.B | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | null | null | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCC(C)S(N)(=O)=O.c1cncc(B2OCCCO2)c1>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-]>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCCC(C)S(N)(=O)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-45a57d7b811b4b1789a26203d86721d9 | O=S(Cl)Cl.O=[N+]([O-])c1cnc2cc(Br)ccc2c1NCCCCCO>>O=[N+]([O-])c1cnc2cc(Br)ccc2c1NCCCCCCl | O.S(=O)(Cl)Cl.BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])NCCCCCO.C([O-])(O)=O.[Na+]>>BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])NCCCCCCl | O=S(Cl)[Cl:21].O[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][NH:15][c:14]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][n:6][c:7]2[cH:8][c:9]([Br:10])[cH:11][cH:12][c:13]21>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][n:6][c:7]2[cH:8][c:9]([Br:10])[cH:11][cH:12][c:13]2[c:14]1[NH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][Cl:21] | O=S(Cl)Cl.O=[N+]([O-])c1cnc2cc(Br)ccc2c1NCCCCCO | O=[N+]([O-])c1cnc2cc(Br)ccc2c1NCCCCCCl | null | null | ClCCl | Functional Group Interconversion | Alcohol to chloride_SOCl2 | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | c1ccc2ncccc2c1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[CH2;D2;+0:2]-[C:3]-[C:4]>>[C:4]-[C:3]-[CH2;D2;+0:2]-[Cl;H0;D1;+0:1] | null | [] | 0 | CELSIUS | 5 | MINUTE | A suspension of 5-(7-bromo-3-nitroquinolin-4-ylamino)pentan-1-ol (0.92 g, 2.6 mmol) in dichloromethane (13 mL) was cooled to 0° C.; thionyl chloride was added dropwise. The reaction was stirred for five minutes at 0° C. then allowed to warm to ambient temperature and stirred overnight. Saturated aqueous sodium bicarbon... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccc2ncccc2c1 | HCl | ClCCl | 0 | 0.083333 | O=S(Cl)Cl.O=[N+]([O-])c1cnc2cc(Br)ccc2c1NCCCCCO>ClCCl>O=[N+]([O-])c1cnc2cc(Br)ccc2c1NCCCCCCl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d3476380362741e8b181f688fb0be9e4 | CCOCc1nc2cnc3cc(Br)ccc3c2n1CCCCCCl.NC(N)=S>>CCOCc1nc2cnc3cc(Br)ccc3c2n1CCCCCSC(=N)N.Cl | NC(=S)N.[I-].[K+].BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CCCCCCl)COCC>>Cl.BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CCCCCSC(N)=N)COCC | [CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]3[c:17]2[n:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][Cl:28].[S:24]=[C:25]([NH2:26])[NH2:27]>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]3[c:17]2[n:18]1[CH... | CCOCc1nc2cnc3cc(Br)ccc3c2n1CCCCCCl.NC(N)=S | CCOCc1nc2cnc3cc(Br)ccc3c2n1CCCCCSC(=N)N.Cl | null | null | CN(C)C=O | Protection | OtherReaction | dae623ec10e42086cc0292009bc19d7d58877ce2428714b92cfbbb5102c39de2 | f72dba6c0cce6a796ff9aeda8637cc446706f96a34b889e05557c4a922c09746 | c1ccc2c(c1)ncc1nc[nH]c12 | [C:1]-[C:2]-[CH2;D2;+0:3]-[Cl;H0;D1;+0:4].[N;D1;H2:5]-[C;H0;D3;+0:6](-[NH2;D1;+0:7])=[S;H0;D1;+0:8]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[S;H0;D2;+0:8]-[C;H0;D3;+0:6](-[N;D1;H2:5])=[NH;D1;+0:7].[ClH;D0;+0:4] | 95.6 | [{"value": 95.6, "product": "Cl.BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CCCCCSC(N)=N)COCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | null | null | Thiourea (0.29 g, 3.8 mmol) and potassium iodide (0.052 g, 3.1 mmol) were sequentially added to a suspension of 7-bromo-1-(5-chloropentyl)-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline (1.3 g, 3.2 mmol) in DMF (15 mL), and the reaction was heated at 110° C. for 24 hours. The DMF was removed under reduced pressure, and the ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Thiourea | Monosulfide | null | null | c1ccc2c(c1)ncc1[nH]cnc12 | null | CN(C)C=O | 110 | null | CCOCc1nc2cnc3cc(Br)ccc3c2n1CCCCCCl.NC(N)=S>CN(C)C=O>CCOCc1nc2cnc3cc(Br)ccc3c2n1CCCCCSC(=N)N.Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f632421fc58442f9bc72226e808ac80b | CCOCc1nc2cnc3cc(Br)ccc3c2n1CCCCCSC(=N)N.Cl.O>>CCOCc1nc2cnc3cc(Br)ccc3c2n1CCCCCS(=O)(=O)Cl | Cl.BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CCCCCSC(N)=N)COCC.Cl(=O)(=O)[O-].[Na+].O>>BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CCCCCS(=O)(=O)Cl)COCC | N=C(N)[S:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][n:18]1[c:5]([CH2:4][O:3][CH2:2][CH3:1])[n:6][c:7]2[cH:8][n:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]3[c:17]21.[ClH:27].[OH2:26]>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]3[c:17]2[n:18]1[CH2:19][C... | CCOCc1nc2cnc3cc(Br)ccc3c2n1CCCCCSC(=N)N.Cl.O | CCOCc1nc2cnc3cc(Br)ccc3c2n1CCCCCS(=O)(=O)Cl | null | null | Cl | Oxidation | OtherReaction | c8e4f0823fd5da6f26236fd3ee99987b5fb983faa69924c535f5f775905feeb8 | 27319d95a096e5d4d5b1b326e21b5809676e06374d8e8d8ebb8a310f3ca2eedf | c1ccc2c(c1)ncc1nc[nH]c12 | N-C(=N)-[S;H0;D2;+0:1]-[C:2]-[C:3].[ClH;D0;+0:4].[OH2;D0;+0:5]>>[C:3]-[C:2]-[S;H0;D4;+0:1](-[Cl;H0;D1;+0:4])(=[O;D1;H0:6])=[O;H0;D1;+0:5] | null | [] | null | null | null | null | A solution of 2-[5-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)pentyl]isothiourea hydrochloride (1.49 g, 3.16 mmol) in 7 M hydrochloric acid (8 mL) was cooled to 0° C. A solution of sodium chlorate (0.44 g, 4.1 mmol) in water (1.0 mL) was added dropwise with stirring, and the reaction was stirred at 0° C. fo... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide | Sulfonyl halide | null | null | c1ccc2c(c1)ncc1[nH]cnc12 | Other | Cl | null | null | CCOCc1nc2cnc3cc(Br)ccc3c2n1CCCCCSC(=N)N.Cl.O>Cl>CCOCc1nc2cnc3cc(Br)ccc3c2n1CCCCCS(=O)(=O)Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0cf36a9b9fe846209e97efb76af17162 | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCC(C)(C)S(N)(=O)=O.OB(O)c1cccnc1>>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCCCC(C)(C)S(N)(=O)=O | CC(CCCCN1C(=NC=2C(=NC=3C=C(C=CC3C21)Br)N)COCC)(S(=O)(=O)N)C.N1=CC(=CC=C1)B(O)O.N1=CC(=CC=C1)B(O)O>>CC(CCCCN1C(=NC=2C(=NC=3C=C(C=CC3C21)C=2C=NC=CC2)N)COCC)(S(=O)(=O)N)C | Br[c:13]1[cH:12][c:11]2[n:10][c:8]([NH2:9])[c:7]3[n:6][c:5]([CH2:4][O:3][CH2:2][CH3:1])[n:24]([CH2:25][CH2:26][CH2:27][CH2:28][C:29]([CH3:30])([CH3:31])[S:32]([NH2:33])(=[O:34])=[O:35])[c:23]3[c:22]2[cH:21][cH:20]1.OB(O)[c:14]1[cH:15][cH:16][cH:17][n:18][cH:19]1>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9]... | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCC(C)(C)S(N)(=O)=O.OB(O)c1cccnc1 | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCCCC(C)(C)S(N)(=O)=O | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | null | C-C Coupling | Suzuki coupling with boronic acids | d23a08b59b246d837a860414fc085402a8d785d2b981e3447d503da913f098ed | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1cncc(-c2ccc3c(c2)ncc2nc[nH]c23)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[c:6](:[#7;a:7]):[c:8](:[#7;a:9]):[c:10]:2:[c:11]:[c:12]:1.O-B(-O)-[c;H0;D3;+0:13]1:[c:14]:[c:15]:[c:16]:[#7;a:17]:[c:18]:1>>[#7;a:9]:[c:8]1:[c:10]2:[c:11]:[c:12]:[c;H0;D3;+0:1](-[c;H0;D3;+0:13]3:[c:14]:[c:15]:[c:16]:[#7;a:17]:[c:18]:3):[c:2]:[c:3]:2:[#7;a:4]:[c:5]:[c:6]:1... | 34.2 | [{"value": 34.2, "product": "CC(CCCCN1C(=NC=2C(=NC=3C=C(C=CC3C21)C=2C=NC=CC2)N)COCC)(S(=O)(=O)N)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | Dimethyl 5-(4-amino-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)pentane-1-sulfonamide (0.26 g, 0.53 mmol) and pyridine-3-boronic acid (0.78 g, 0.63 mmol) were coupled according to the method described in Part J of Example 1. The reaction was heated at 100° C. for 31 hours, at which time additional palladium a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1 | HBr.B | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | null | 14 | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCC(C)(C)S(N)(=O)=O.OB(O)c1cccnc1>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-]>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCCCC(C)(C)S(N)(=O)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ce7e2c982b6d4f79bcb6c0ac461bd472 | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCC(C)S(N)(=O)=O.OB(O)c1cccnc1>>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCCCC(C)S(N)(=O)=O | CC(CCCCN1C(=NC=2C(=NC=3C=C(C=CC3C21)Br)N)COCC)S(=O)(=O)N.N1=CC(=CC=C1)B(O)O>>CC(CCCCN1C(=NC=2C(=NC=3C=C(C=CC3C21)C=2C=NC=CC2)N)COCC)S(=O)(=O)N | Br[c:13]1[cH:12][c:11]2[n:10][c:8]([NH2:9])[c:7]3[n:6][c:5]([CH2:4][O:3][CH2:2][CH3:1])[n:24]([CH2:25][CH2:26][CH2:27][CH2:28][CH:29]([CH3:30])[S:31]([NH2:32])(=[O:33])=[O:34])[c:23]3[c:22]2[cH:21][cH:20]1.OB(O)[c:14]1[cH:15][cH:16][cH:17][n:18][cH:19]1>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c... | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCC(C)S(N)(=O)=O.OB(O)c1cccnc1 | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCCCC(C)S(N)(=O)=O | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | d23a08b59b246d837a860414fc085402a8d785d2b981e3447d503da913f098ed | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1cncc(-c2ccc3c(c2)ncc2nc[nH]c23)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[c:6](:[#7;a:7]):[c:8](:[#7;a:9]):[c:10]:2:[c:11]:[c:12]:1.O-B(-O)-[c;H0;D3;+0:13]1:[c:14]:[c:15]:[c:16]:[#7;a:17]:[c:18]:1>>[#7;a:9]:[c:8]1:[c:10]2:[c:11]:[c:12]:[c;H0;D3;+0:1](-[c;H0;D3;+0:13]3:[c:14]:[c:15]:[c:16]:[#7;a:17]:[c:18]:3):[c:2]:[c:3]:2:[#7;a:4]:[c:5]:[c:6]:1... | 27.8 | [{"value": 27.8, "product": "CC(CCCCN1C(=NC=2C(=NC=3C=C(C=CC3C21)C=2C=NC=CC2)N)COCC)S(=O)(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Methyl 5-(4-amino-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)pentane-1-sulfonamide (0.47 g, 0.97 mmol) was coupled with pyridine-3-boronic acid (0.14 g, 1.2 mmol) according to the methods described in Part J of Example 1 and Part H of Example 370. The crude product was purified twice by HPFC (eluting with ch... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1 | HBr.B | null | null | null | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCC(C)S(N)(=O)=O.OB(O)c1cccnc1>>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCCCC(C)S(N)(=O)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-17aa753a322d4484be062a0385310189 | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCCCNC(=O)OC(C)(C)C>>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCCCN | NC1=NC=2C=C(C=CC2C2=C1N=C(N2CCCCNC(OC(C)(C)C)=O)COCC)C=2C=NC=CC2>>NCCCCN1C(=NC=2C(=NC=3C=C(C=CC3C21)C=2C=NC=CC2)N)COCC | CC(C)(C)OC(=O)[NH:29][CH2:28][CH2:27][CH2:26][CH2:25][n:24]1[c:5]([CH2:4][O:3][CH2:2][CH3:1])[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13](-[c:14]4[cH:15][cH:16][cH:17][n:18][cH:19]4)[cH:20][cH:21][c:22]3[c:23]21>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13](-[c:14]4[cH:15][... | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCCCNC(=O)OC(C)(C)C | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCCCN | null | null | Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1cncc(-c2ccc3c(c2)ncc2nc[nH]c23)c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | 113.6 | [{"value": 113.6, "product": "NCCCCN1C(=NC=2C(=NC=3C=C(C=CC3C21)C=2C=NC=CC2)N)COCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of tert-butyl {4-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl}carbamate (40.35 g, 82.24 mmol) in concentrated hydrochloric acid (400 mL) was stirred for one hour, filtered, and concentrated under reduced pressure. The residue was dissolved in a minimal amount of water, and 50... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1 | HO- | Cl | null | 0.5 | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCCCNC(=O)OC(C)(C)C>Cl>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCCCN |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8286c1f00f7142c681fea48b02e013db | CCCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCCCNC(=O)OC(C)(C)C>>CCCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCCCN | C([O-])(O)=O.[Na+].C([O-])([O-])=O.[Na+].[Na+].NC1=NC=2C=C(C=CC2C2=C1N=C(N2CCCCNC(OC(C)(C)C)=O)CCC)C=2C=NC=CC2.[OH-].[Na+].[Cl-].[Na+]>>NCCCCN1C(=NC=2C(=NC=3C=C(C=CC3C21)C=2C=NC=CC2)N)CCC | CC(C)(C)OC(=O)[NH:28][CH2:27][CH2:26][CH2:25][CH2:24][n:23]1[c:4]([CH2:3][CH2:2][CH3:1])[n:5][c:6]2[c:7]([NH2:8])[n:9][c:10]3[cH:11][c:12](-[c:13]4[cH:14][cH:15][cH:16][n:17][cH:18]4)[cH:19][cH:20][c:21]3[c:22]21>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]2[c:7]([NH2:8])[n:9][c:10]3[cH:11][c:12](-[c:13]4[cH:14][cH:15][cH:16... | CCCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCCCNC(=O)OC(C)(C)C | CCCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCCCN | null | null | C(Cl)(Cl)Cl.Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1cncc(-c2ccc3c(c2)ncc2nc[nH]c23)c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | 87 | [{"value": 87.0, "product": "NCCCCN1C(=NC=2C(=NC=3C=C(C=CC3C21)C=2C=NC=CC2)N)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of tert-butyl {4-[4-amino-2-propyl-7-(pyridin-3-yl)-1H-imidazol[4,5-c]quinolin-1-yl]butyl}carbamate (41.92 g, 88.32 mmol) in concentrated hydrochloric acid (210 mL) was stirred for ten minutes, and 50% aqueous sodium hydroxide was added to adjust the solution to pH 14. Cloroform (2.0 L) and a mixture of satu... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1 | HO- | C(Cl)(Cl)Cl.Cl | null | 8 | CCCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCCCNC(=O)OC(C)(C)C>C(Cl)(Cl)Cl.Cl>CCCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCCCN |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4c81e4ee6509425ba1349d592b141c5f | CC(C)(C)OC(=O)NCCNc1c([N+](=O)[O-])cnc2cc(Br)ccc12>>CC(C)(C)OC(=O)NCCNc1c(N)cnc2cc(Br)ccc12 | C(C)(C)(C)OC(NCCNC1=C(C=NC2=CC(=CC=C12)Br)[N+](=O)[O-])=O.C(C)(C)O>>NC=1C=NC2=CC(=CC=C2C1NCCNC(OC(C)(C)C)=O)Br | O=[N+:14]([O-])[c:13]1[c:12]([NH:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[c:23]2[c:17]([n:16][cH:15]1)[cH:18][c:19]([Br:20])[cH:21][cH:22]2>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][NH:11][c:12]1[c:13]([NH2:14])[cH:15][n:16][c:17]2[cH:18][c:19]([Br:20])[cH:2... | CC(C)(C)OC(=O)NCCNc1c([N+](=O)[O-])cnc2cc(Br)ccc12 | CC(C)(C)OC(=O)NCCNc1c(N)cnc2cc(Br)ccc12 | null | [Pt] | C(C)#N | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2ncccc2c1 | 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] | 91.1 | [{"value": 91.1, "product": "NC=1C=NC2=CC(=CC=C2C1NCCNC(OC(C)(C)C)=O)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of tert-butyl[2-(7-bromo-3-nitroquinolin-4-ylamino)ethyl]carbamate (165.0 g, 401.2 mmol) in acetonitrile (3.3 L) and, isopropanol (990 mL) and 5% platinum on carbon (13.2 g) were added to a Parr vessel, which was placed under hydrogen pressure (50 psi, 3.4×105 Pa) overnight. The mixture was filtered through ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2ncccc2c1 | Other | [Pt].C(C)#N | null | null | CC(C)(C)OC(=O)NCCNc1c([N+](=O)[O-])cnc2cc(Br)ccc12>[Pt].C(C)#N>CC(C)(C)OC(=O)NCCNc1c(N)cnc2cc(Br)ccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b4129340568849b5959a9ea21a3b9236 | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCNC(=O)OC(C)(C)C.OB(O)c1cccnc1>>CCOCc1nc2cnc3cc(-c4cccnc4)ccc3c2n1CCNC(=O)OC(C)(C)C | C(C)(C)(C)OC(NCCN1C(=NC=2C(=NC=3C=C(C=CC3C21)Br)N)COCC)=O.N1=CC(=CC=C1)B(O)O>>C(C)OCC=1N(C2=C(C=NC=3C=C(C=CC23)C=2C=NC=CC2)N1)CCNC(OC(C)(C)C)=O | N[c:8]1[c:7]2[n:6][c:5]([CH2:4][O:3][CH2:2][CH3:1])[n:23]([CH2:24][CH2:25][NH:26][C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33])[c:22]2[c:21]2[c:10]([n:9]1)[cH:11][c:12](Br)[cH:19][cH:20]2.OB(O)[c:13]1[cH:14][cH:15][cH:16][n:17][cH:18]1>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:9][c:10]3[cH:11][c:12... | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCNC(=O)OC(C)(C)C.OB(O)c1cccnc1 | CCOCc1nc2cnc3cc(-c4cccnc4)ccc3c2n1CCNC(=O)OC(C)(C)C | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | e9d881b426c9c0b8a93a40293c3d0b6c34b426c55c2d9cabdc9aa863bd3d8244 | 79fc43732b29814f22dd0a7cbc24a0ef705cb8e808911cfb2a64a2630fa44903 | c1cncc(-c2ccc3c(c2)ncc2nc[nH]c23)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c;H0;D3;+0:5](-N):[c:6]3:[#7;a:7]:[c:8]:[#7;a:9](-[C:10]):[c:11]:3:[c:12]:2:[c:13]:[c:14]:1.O-B(-O)-[c;H0;D3;+0:15]1:[c:16]:[c:17]:[c:18]:[#7;a:19]:[c:20]:1>>[C:10]-[#7;a:9]1:[c:8]:[#7;a:7]:[c:6]2:[cH;D2;+0:5]:[#7;a:4]:[c:3]3:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:15]4:[c:16]:[c:17]... | 51.4 | [{"value": 51.4, "product": "C(C)OCC=1N(C2=C(C=NC=3C=C(C=CC23)C=2C=NC=CC2)N1)CCNC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | tert-Butyl[2-(4-amino-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]carbamate (21.80 g, 46.94 mmol) and 3-pyridylboronic acid (6.64 g, 54.0 mmol) were coupled according to the method described in Part J of Example 1. Palladium (II) acetate was added as a 5 mg/mL solution in toluene. The reaction was termi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine.Boronic acid | null | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1 | HBr.B | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)C | null | null | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCNC(=O)OC(C)(C)C.OB(O)c1cccnc1>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)C>CCOCc1nc2cnc3cc(-c4cccnc4)ccc3c2n1CCNC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-300f431f77bb4ac1863898c99805673a | CC(C)C(=O)Cl.CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCN>>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCNC(=O)C(C)C | NCCN1C(=NC=2C(=NC=3C=C(C=CC3C21)C=2C=NC=CC2)N)COCC.C(C)N(CC)CC.C(C(C)C)(=O)Cl>>NC1=NC=2C=C(C=CC2C2=C1N=C(N2CCNC(C(C)C)=O)COCC)C=2C=NC=CC2 | Cl[C:28](=[O:29])[CH:30]([CH3:31])[CH3:32].[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13](-[c:14]4[cH:15][cH:16][cH:17][n:18][cH:19]4)[cH:20][cH:21][c:22]3[c:23]2[n:24]1[CH2:25][CH2:26][NH2:27]>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13](-[c:... | CC(C)C(=O)Cl.CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCN | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCNC(=O)C(C)C | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1cncc(-c2ccc3c(c2)ncc2nc[nH]c23)c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[C;D1;H3:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[C;D1;H3:5] | 32.8 | [{"value": 32.8, "product": "NC1=NC=2C=C(C=CC2C2=C1N=C(N2CCNC(C(C)C)=O)COCC)C=2C=NC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-(2-Aminoethyl)-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine (2.00 g, 5.50 mmol) was treated with triethylamine (1.00 mL, 7.20 mmol) and isobutyryl chloride (0.64 mL, 6.10 mmol) according to the method described in Part B of Examples 372–376. The crude product was recrystallized from 93:7 acetonit... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1 | HCl | null | null | null | CC(C)C(=O)Cl.CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCN>>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCNC(=O)C(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f821a871b0c34016a9207fe1cb068308 | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCN.CS(=O)(=O)Cl>>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCNS(C)(=O)=O | CS(=O)(=O)Cl.NCCN1C(=NC=2C(=NC=3C=C(C=CC3C21)C=2C=NC=CC2)N)COCC.C(C)N(CC)CC.CS(=O)(=O)Cl.O>>NC1=NC=2C=C(C=CC2C2=C1N=C(N2CCNS(=O)(=O)C)COCC)C=2C=NC=CC2 | [CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13](-[c:14]4[cH:15][cH:16][cH:17][n:18][cH:19]4)[cH:20][cH:21][c:22]3[c:23]2[n:24]1[CH2:25][CH2:26][NH2:27].Cl[S:28]([CH3:29])(=[O:30])=[O:31]>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13](-[c:14]4[cH:... | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCN.CS(=O)(=O)Cl | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCNS(C)(=O)=O | null | null | C(Cl)(Cl)Cl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | c1cncc(-c2ccc3c(c2)ncc2nc[nH]c23)c1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 26.8 | [{"value": 26.8, "product": "NC1=NC=2C=C(C=CC2C2=C1N=C(N2CCNS(=O)(=O)C)COCC)C=2C=NC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | A solution of 1-(2-aminoethyl)-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine (2.00 g, 5.50 mmol) in chloroform (40 mL) was treated with triethylamine (1.62 mL, 11.6 mmol) and methanesulfonyl chloride (0.47 mL, 6.05 mmol). The reaction was stirred for 1.5 hours, and additional methanesulfonyl chlorid... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1 | HCl | C(Cl)(Cl)Cl | null | 1.5 | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCN.CS(=O)(=O)Cl>C(Cl)(Cl)Cl>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCNS(C)(=O)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d16d8d902d0c45cfb7ea9fa85a26dbda | CC(C)N=C=O.CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCN>>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCNC(=O)NC(C)C | NCCN1C(=NC=2C(=NC=3C=C(C=CC3C21)C=2C=NC=CC2)N)COCC.C(C)(C)N=C=O>>NC1=NC=2C=C(C=CC2C2=C1N=C(N2CCNC(=O)NC(C)C)COCC)C=2C=NC=CC2 | [C:28](=[O:29])=[N:30][CH:31]([CH3:32])[CH3:33].[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13](-[c:14]4[cH:15][cH:16][cH:17][n:18][cH:19]4)[cH:20][cH:21][c:22]3[c:23]2[n:24]1[CH2:25][CH2:26][NH2:27]>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13]... | CC(C)N=C=O.CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCN | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCNC(=O)NC(C)C | null | null | C(Cl)(Cl)Cl | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1cncc(-c2ccc3c(c2)ncc2nc[nH]c23)c1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])-[N;H0;D2;+0:4]=[C;H0;D2;+0:5]=[O;D1;H0:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[NH;D2;+0:4]-[C:2](-[C;D1;H3:1])-[C;D1;H3:3] | 28.5 | [{"value": 28.5, "product": "NC1=NC=2C=C(C=CC2C2=C1N=C(N2CCNC(=O)NC(C)C)COCC)C=2C=NC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 1-(2-aminoethyl)-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine (2.50 g, 6.90 mmol) in chloroform (50 mL) was treated with isopropyl isocyanate (0.65 mL, 6.9 mmol) according to the method described in Examples 377–379. The crude product was purified by column chromatography on silica ge... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1 | null | C(Cl)(Cl)Cl | null | null | CC(C)N=C=O.CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCN>C(Cl)(Cl)Cl>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCNC(=O)NC(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bd2e3b5bb7384ffca222305e95fc44cb | CCCCc1nc2c(N)nc3cc(Br)ccc3c2n1CCNC(=O)OC(C)(C)C.OB(O)c1cccnc1>>CCCCc1nc2cnc3cc(-c4cccnc4)ccc3c2n1CCNC(=O)OC(C)(C)C | C(C)(C)(C)OC(NCCN1C(=NC=2C(=NC=3C=C(C=CC3C21)Br)N)CCCC)=O.N1=CC(=CC=C1)B(O)O>>C(C)(C)(C)OC(NCCN1C(=NC=2C=NC=3C=C(C=CC3C21)C=2C=NC=CC2)CCCC)=O | N[c:8]1[c:7]2[n:6][c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[n:23]([CH2:24][CH2:25][NH:26][C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33])[c:22]2[c:21]2[c:10]([n:9]1)[cH:11][c:12](Br)[cH:19][cH:20]2.OB(O)[c:13]1[cH:14][cH:15][cH:16][n:17][cH:18]1>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:9][c:10]3[cH:11][... | CCCCc1nc2c(N)nc3cc(Br)ccc3c2n1CCNC(=O)OC(C)(C)C.OB(O)c1cccnc1 | CCCCc1nc2cnc3cc(-c4cccnc4)ccc3c2n1CCNC(=O)OC(C)(C)C | null | null | null | C-C Coupling | OtherReaction | e9d881b426c9c0b8a93a40293c3d0b6c34b426c55c2d9cabdc9aa863bd3d8244 | 79fc43732b29814f22dd0a7cbc24a0ef705cb8e808911cfb2a64a2630fa44903 | c1cncc(-c2ccc3c(c2)ncc2nc[nH]c23)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c;H0;D3;+0:5](-N):[c:6]3:[#7;a:7]:[c:8]:[#7;a:9](-[C:10]):[c:11]:3:[c:12]:2:[c:13]:[c:14]:1.O-B(-O)-[c;H0;D3;+0:15]1:[c:16]:[c:17]:[c:18]:[#7;a:19]:[c:20]:1>>[C:10]-[#7;a:9]1:[c:8]:[#7;a:7]:[c:6]2:[cH;D2;+0:5]:[#7;a:4]:[c:3]3:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:15]4:[c:16]:[c:17]... | 83.2 | [{"value": 83.2, "product": "C(C)(C)(C)OC(NCCN1C(=NC=2C=NC=3C=C(C=CC3C21)C=2C=NC=CC2)CCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | tert-Butyl[2-(4-amino-7-bromo-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]carbamate (14.09 g, 30.5 mmol) and 3-pyridylboronic acid (4.31 g, 35.0 mmol) were coupled according to the method described in Part G of Example 386. The reaction was heated for 2.5 hours. The crude product was triturated with toluene (15 mL/g) ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine.Boronic acid | null | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1 | HBr.B | null | null | null | CCCCc1nc2c(N)nc3cc(Br)ccc3c2n1CCNC(=O)OC(C)(C)C.OB(O)c1cccnc1>>CCCCc1nc2cnc3cc(-c4cccnc4)ccc3c2n1CCNC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d4a7e716ac644acf804bc7c29619114a | CC(C)C(=O)Cl.CCCCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCN>>CCCCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCNC(=O)C(C)C | NCCN1C(=NC=2C(=NC=3C=C(C=CC3C21)C=2C=NC=CC2)N)CCCC.C(C)N(CC)CC.C(C(C)C)(=O)Cl>>NC1=NC=2C=C(C=CC2C2=C1N=C(N2CCNC(C(C)C)=O)CCCC)C=2C=NC=CC2 | Cl[C:28](=[O:29])[CH:30]([CH3:31])[CH3:32].[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13](-[c:14]4[cH:15][cH:16][cH:17][n:18][cH:19]4)[cH:20][cH:21][c:22]3[c:23]2[n:24]1[CH2:25][CH2:26][NH2:27]>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13](... | CC(C)C(=O)Cl.CCCCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCN | CCCCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCNC(=O)C(C)C | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1cncc(-c2ccc3c(c2)ncc2nc[nH]c23)c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[C;D1;H3:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[C;D1;H3:5] | 25.8 | [{"value": 25.8, "product": "NC1=NC=2C=C(C=CC2C2=C1N=C(N2CCNC(C(C)C)=O)CCCC)C=2C=NC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-(2-Aminoethyl)-2-butyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine (2.00 g, 5.50 mmol) was treated with triethylamine (1.01 mL, 7.26 mmol) and isobutyryl chloride (0.64 mL, 6.10 mmol) according to the method described in Part B of Examples 372–376. The crude product was recrystallized from isopropanol (4 mL/g)... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1 | HCl | null | null | null | CC(C)C(=O)Cl.CCCCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCN>>CCCCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCNC(=O)C(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3db7633c7790473bbf510fa12aa014cc | CC(C)N=C=O.CCCCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCN>>CCCCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCNC(=O)NC(C)C | C(C)(C)N=C=O.NCCN1C(=NC=2C(=NC=3C=C(C=CC3C21)C=2C=NC=CC2)N)CCCC>>NC1=NC=2C=C(C=CC2C2=C1N=C(N2CCNC(=O)NC(C)C)CCCC)C=2C=NC=CC2 | [C:28](=[O:29])=[N:30][CH:31]([CH3:32])[CH3:33].[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13](-[c:14]4[cH:15][cH:16][cH:17][n:18][cH:19]4)[cH:20][cH:21][c:22]3[c:23]2[n:24]1[CH2:25][CH2:26][NH2:27]>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c... | CC(C)N=C=O.CCCCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCN | CCCCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCNC(=O)NC(C)C | null | null | C(Cl)(Cl)Cl | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1cncc(-c2ccc3c(c2)ncc2nc[nH]c23)c1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])-[N;H0;D2;+0:4]=[C;H0;D2;+0:5]=[O;D1;H0:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[NH;D2;+0:4]-[C:2](-[C;D1;H3:1])-[C;D1;H3:3] | 47.8 | [{"value": 47.8, "product": "NC1=NC=2C=C(C=CC2C2=C1N=C(N2CCNC(=O)NC(C)C)CCCC)C=2C=NC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Isopropyl isocyanate (0.29 mL, 3.1 mmol) was added slowly to a suspension of 1-(2-aminoethyl)-2-butyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine (1.13 g, 3.1 mmol) in chloroform (113 mL). A precipitate formed within 15 minutes, was isolated by filtration, and was dried overnight in an oven to provide 0.66 g of ... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1 | null | C(Cl)(Cl)Cl | null | null | CC(C)N=C=O.CCCCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCN>C(Cl)(Cl)Cl>CCCCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCNC(=O)NC(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9ba31f07c1b444a68ce2aed691763f55 | CC(C)(C)OC(=O)N1CCC(CNc2c(N)cnc3cc(Br)ccc23)CC1.CCOC(CC)(OCC)OCC>>CCc1nc2cnc3cc(Br)ccc3c2n1CC1CCN(C(=O)OC(C)(C)C)CC1 | NC=1C=NC2=CC(=CC=C2C1NCC1CCN(CC1)C(=O)OC(C)(C)C)Br.C(CC)(OCC)(OCC)OCC>>BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CC3CCN(CC3)C(=O)OC(C)(C)C)CC | [NH2:4][c:5]1[cH:6][n:7][c:8]2[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]2[c:15]1[NH:16][CH2:17][CH:18]1[CH2:19][CH2:20][N:21]([C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[CH2:29][CH2:30]1.CCO[C:3](OCC)(OCC)[CH2:2][CH3:1]>>[CH3:1][CH2:2][c:3]1[n:4][c:5]2[cH:6][n:7][c:8]3[cH:9][c:10]([Br:11])[cH:12][cH:13][c:1... | CC(C)(C)OC(=O)N1CCC(CNc2c(N)cnc3cc(Br)ccc23)CC1.CCOC(CC)(OCC)OCC | CCc1nc2cnc3cc(Br)ccc3c2n1CC1CCN(C(=O)OC(C)(C)C)CC1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 8d87c769e65778c9400c7f523e0409ecf0ffad86543cd9fdd6ef4b239323db96 | a60e703c3cf5c0d933aa031358d338c45d96ec82dec3fc2d9f5dce06b9dcc651 | c1ccc2c(c1)ncc1ncn(CC3CCNCC3)c12 | C-C-O-[C;H0;D4;+0:1](-O-C-C)(-O-C-C)-[C:2]-[C;D1;H3:3].[C:4]-[C:5]-[NH;D2;+0:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1-[NH2;D1;+0:13]>>[C:4]-[C:5]-[n;H0;D3;+0:6]1:[c:7]2:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:2:[n;H0;D2;+0:13]:[c;H0;D3;+0:1]:1-[C:2]-[C;D1;H3:3] | 77.1 | [{"value": 77.1, "product": "BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CC3CCN(CC3)C(=O)OC(C)(C)C)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The method described in Part A of Examples 142–144 was used to treat tert-butyl 4-[(3-amino-7-bromoquinolin-4-ylamino)methyl]piperidine-1-carboxylate (15.0 g, 34.5 mmol) with triethyl orthopropionate (6.68 g, 37.9 mmol). After completion, the reaction mixture was concentrated under reduced pressure, and the residue was... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Primary amine.Secondary amine | null | c1ccc2ncccc2c1 | c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12.C1CC[NH]CC1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCC(CNc2c(N)cnc3cc(Br)ccc23)CC1.CCOC(CC)(OCC)OCC>>CCc1nc2cnc3cc(Br)ccc3c2n1CC1CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6ab58770b4c24ae7b57719be753f7eac | CCc1nc2c(N)nc3cc(Br)ccc3c2n1CC1CCN(C(=O)OC(C)(C)C)CC1.c1cncc(B2OCCCO2)c1>>CCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC1CCN(C(=O)OC(C)(C)C)CC1 | NC1=NC=2C=C(C=CC2C2=C1N=C(N2CC2CCN(CC2)C(=O)OC(C)(C)C)CC)Br.B1(OCCCO1)C2=CN=CC=C2>>NC1=NC=2C=C(C=CC2C2=C1N=C(N2CC2CCN(CC2)C(=O)OC(C)(C)C)CC)C=2C=NC=CC2 | Br[c:11]1[cH:10][c:9]2[n:8][c:6]([NH2:7])[c:5]3[n:4][c:3]([CH2:2][CH3:1])[n:22]([CH2:23][CH:24]4[CH2:25][CH2:26][N:27]([C:28](=[O:29])[O:30][C:31]([CH3:32])([CH3:33])[CH3:34])[CH2:35][CH2:36]4)[c:21]3[c:20]2[cH:19][cH:18]1.C1COB([c:12]2[cH:13][cH:14][cH:15][n:16][cH:17]2)OC1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]2[c:6]([NH2:7... | CCc1nc2c(N)nc3cc(Br)ccc3c2n1CC1CCN(C(=O)OC(C)(C)C)CC1.c1cncc(B2OCCCO2)c1 | CCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC1CCN(C(=O)OC(C)(C)C)CC1 | null | null | O | C-C Coupling | Suzuki coupling with boronic esters | 2cd1cbe6f17c98cb5223a75d20dfc144a6eae8461c4fe8a7e9cc4bc7ecadb166 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1cncc(-c2ccc3c(c2)ncc2ncn(CC4CCNCC4)c23)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[c:6](:[#7;a:7]):[c:8](:[#7;a:9]):[c:10]:2:[c:11]:[c:12]:1.C1-C-O-B(-[c;H0;D3;+0:13]2:[c:14]:[c:15]:[c:16]:[#7;a:17]:[c:18]:2)-O-C-1>>[#7;a:9]:[c:8]1:[c:10]2:[c:11]:[c:12]:[c;H0;D3;+0:1](-[c;H0;D3;+0:13]3:[c:14]:[c:15]:[c:16]:[#7;a:17]:[c:18]:3):[c:2]:[c:3]:2:[#7;a:4]:[c:5... | 59.2 | [{"value": 59.2, "product": "NC1=NC=2C=C(C=CC2C2=C1N=C(N2CC2CCN(CC2)C(=O)OC(C)(C)C)CC)C=2C=NC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | tert-Butyl 4-[(4-amino-7-bromo-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]piperidine-1-carboxylate (9.24 g, 18.9 mmol) and pyridine-3-boronic acid 1,3-propanediol cyclic ester (3.39 g, 20.8 mmol) were coupled according to the method described in Examples 118–121. Additional reagents were added after the reaction was... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2c(c1)ncc1[nH]cnc12.B1OCCCO1.c1ccncc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1.C1CC[NH]CC1 | HBr.B | O | null | 16 | CCc1nc2c(N)nc3cc(Br)ccc3c2n1CC1CCN(C(=O)OC(C)(C)C)CC1.c1cncc(B2OCCCO2)c1>O>CCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC1CCN(C(=O)OC(C)(C)C)CC1 |
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