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-096d773aff6c4128951312bff972383e | CCOC(=O)c1c(-c2cccc(C)n2)nn2c1CCC2>>Cc1cccc(-c2nn3c(c2C(=O)O)CCC3)n1 | C(C)OC(=O)C1=C2N(N=C1C1=NC(=CC=C1)C)CCC2.[OH-].[Na+]>>CC1=CC=CC(=N1)C=1C(=C2N(N1)CCC2)C(=O)O | CC[O:14][C:12]([c:11]1[c:7](-[c:6]2[cH:5][cH:4][cH:3][c:2]([CH3:1])[n:18]2)[n:8][n:9]2[c:10]1[CH2:15][CH2:16][CH2:17]2)=[O:13]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[n:8][n:9]3[c:10]([c:11]2[C:12](=[O:13])[OH:14])[CH2:15][CH2:16][CH2:17]3)[n:18]1 | CCOC(=O)c1c(-c2cccc(C)n2)nn2c1CCC2 | Cc1cccc(-c2nn3c(c2C(=O)O)CCC3)n1 | null | null | C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2cc3n(n2)CCC3)nc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[c:5]:[#7;a:6]:[#7;a:7]:[c:8]:1>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4]1:[c:5]:[#7;a:6]:[#7;a:7]:[c:8]:1 | null | [] | null | null | null | null | A solution of 2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylic acid ethyl ester (1.6 g, 5.9 mmol) and 2 N sodium hydroxide (6 mL, 29 mmol) in absolute ethanol (50 mL) is refluxed for 5 h. The mixture is cooled to room temperature and concentrated in vacuo. The residue is suspended in water a... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccncc1.c1cc2n(n1)CCC2 | Other | C(C)O | null | null | CCOC(=O)c1c(-c2cccc(C)n2)nn2c1CCC2>C(C)O>Cc1cccc(-c2nn3c(c2C(=O)O)CCC3)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-89e061fe72f54d6990f195745c8d82e2 | Cc1cccc(-c2nn3c(c2C(=O)O)CCC3)n1.NC(=O)CCC(=O)NBr>>Cc1cccc(-c2nn3c(c2Br)CCC3)n1 | CC1=CC=CC(=N1)C=1C(=C2N(N1)CCC2)C(=O)O.BrNC(CCC(=O)N)=O>>BrC1=C2N(N=C1C1=NC(=CC=C1)C)CCC2 | O=C(O)[c:11]1[c:7](-[c:6]2[cH:5][cH:4][cH:3][c:2]([CH3:1])[n:16]2)[n:8][n:9]2[c:10]1[CH2:13][CH2:14][CH2:15]2.NC(=O)CCC(=O)N[Br:12]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[n:8][n:9]3[c:10]([c:11]2[Br:12])[CH2:13][CH2:14][CH2:15]3)[n:16]1 | Cc1cccc(-c2nn3c(c2C(=O)O)CCC3)n1.NC(=O)CCC(=O)NBr | Cc1cccc(-c2nn3c(c2Br)CCC3)n1 | null | null | CN(C=O)C.C(C)(=O)OCC | Functional Group Interconversion | OtherReaction | 8b8c70d4e8bb4e0f48d8bd7b9fb1eea054fb2a9e5d3234fd49918ae3d5edf1a0 | 7152e548e20ab177ec9c36dcbd6278f9362f912f2d7a61ce80771f344eb64217 | c1ccc(-c2cc3n(n2)CCC3)nc1 | N-C(=O)-C-C-C(=O)-N-[Br;H0;D1;+0:1].O-C(=O)-[c;H0;D3;+0:2]1:[c:3](:[#7;a:4](:[#7;a:5]:[c:6]:1-[c:7]:[#7;a:8])-[C:9])-[C:10]>>[#7;a:8]:[c:7]-[c:6]1:[#7;a:5]:[#7;a:4](:[c:3](:[c;H0;D3;+0:2]:1-[Br;H0;D1;+0:1])-[C:10])-[C:9] | null | [] | null | null | 16 | HOUR | A solution of 2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylic acid (1.4 g, 5.8 mmol) in N,N-dimethylformamide (20 mL) is treated with N-bromosuccinamide (1 g, 5.6 mmol) and stirred at room temperature for 16 h. The mixture is diluted with ethyl acetate and washed three times with water, onc... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amide.Secondary amide | Aromatic halide | c1cc2n(n1)CCC2 | c1cc2n(n1)CCC2 | c1ccncc1.c1cc2n(n1)CCC2 | HO- | CN(C=O)C.C(C)(=O)OCC | null | 16 | Cc1cccc(-c2nn3c(c2C(=O)O)CCC3)n1.NC(=O)CCC(=O)NBr>CN(C=O)C.C(C)(=O)OCC>Cc1cccc(-c2nn3c(c2Br)CCC3)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-482e9e53739947068ed5441ee039ebd0 | COC(=O)c1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1>>O=C(O)c1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | O.[OH-].[Li+].COC(=O)C1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC=CC=C1)CCC2>>N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC(=CC=C21)C(=O)O | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]2[c:8](-[c:9]3[c:10](-[c:11]4[cH:12][cH:13][cH:14][cH:15][n:16]4)[n:17][n:18]4[c:19]3[CH2:20][CH2:21][CH2:22]4)[cH:23][cH:24][n:25][c:26]2[cH:27]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[c:8](-[c:9]3[c:10](-[c:11]4[cH:12][cH:13][cH:14][cH:15][n:16]4)[n:17][n:18]4[c:19]3[CH... | COC(=O)c1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | O=C(O)c1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | null | null | O1CCCC1.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)nc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | 18 | HOUR | Lithium hydroxide monohydrate (0.65 g, 15.6 mmol) is added to a solution of 4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline-7-carboxylic acid methyl ester (1.44 g, 3.89 mmol) in 2:1 tetrahydrofuran/water (30 mL), stirred at room temperature for 18 h, and concentrated in vacuo. The residue is puri... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccncc1.c1cc2n(n1)CCC2.c1ccc2ncccc2c1 | Other | O1CCCC1.O | null | 18 | COC(=O)c1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1>O1CCCC1.O>O=C(O)c1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f65978114b994b5ead93e25904dd8fe7 | ClC(Cl)(Cl)Cl.OCc1ccc2c(c1)OC(F)(F)O2>>FC1(F)Oc2ccc(CCl)cc2O1 | FC1(OC2=C(O1)C=CC(=C2)CO)F.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(Cl)(Cl)(Cl)Cl>>ClCC1=CC2=C(OC(O2)(F)F)C=C1 | ClC(Cl)(Cl)[Cl:10].O[CH2:9][c:8]1[cH:7][cH:6][c:5]2[c:12]([cH:11]1)[O:13][C:2]([F:1])([F:3])[O:4]2>>[F:1][C:2]1([F:3])[O:4][c:5]2[cH:6][cH:7][c:8]([CH2:9][Cl:10])[cH:11][c:12]2[O:13]1 | ClC(Cl)(Cl)Cl.OCc1ccc2c(c1)OC(F)(F)O2 | FC1(F)Oc2ccc(CCl)cc2O1 | null | null | null | Functional Group Interconversion | Alcohol to chloride_Other | c7645f5879ae909e3b297fc6726e5b7253e918a949dafa12692ea59b390e5913 | cadad225bb90b3f5f5246e3c4efc1bc11b99bbdc1142f65854e2e6aa61cf93e1 | c1ccc2c(c1)OCO2 | Cl-C(-Cl)(-Cl)-[Cl;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[Cl;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | 80 | CELSIUS | null | null | A solution of (2,2-difluoro-benzo[1,3]dioxol-5-yl)-methanol (1.0 g, 5.32 mmol) in carbon tetrachloride (10.6 mL) is added to polymer-supported triphenylphospine (3.5 g, 3 mmol/g, 10.6 mmol) at room temperature. The reaction is heated for 3 h at 80° C., cooled to room temperature, filtered, and the solids washed with di... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Trichloro group.Primary alcohol | Primary halide | null | null | c1ccc2c(c1)OCO2 | HCl | null | 80 | null | ClC(Cl)(Cl)Cl.OCc1ccc2c(c1)OC(F)(F)O2>>FC1(F)Oc2ccc(CCl)cc2O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4b3d4902b78f465d8d45d8b15e7477f9 | CS(=O)(=O)Cl.Cc1cccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3CO)n1>>CS(=O)(=O)OCC1CCc2c(-c3ccnc4ccccc34)c(-c3ccccn3)nn21 | CC1=CC=CC(=N1)C=1C(=C2N(N1)C(CC2)CO)C2=CC=NC1=CC=CC=C21.CS(=O)(=O)Cl>>N1=C(C=CC=C1)C=1C(=C2N(N1)C(CC2)COS(=O)(=O)C)C2=CC=NC1=CC=CC=C21 | Cl[S:2]([CH3:1])(=[O:3])=[O:4].C[c:27]1[cH:26][cH:25][cH:24][c:23](-[c:22]2[c:11](-[c:12]3[cH:13][cH:14][n:15][c:16]4[cH:17][cH:18][cH:19][cH:20][c:21]34)[c:10]3[n:30]([n:29]2)[CH:7]([CH2:6][OH:5])[CH2:8][CH2:9]3)[n:28]1>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][CH:7]1[CH2:8][CH2:9][c:10]2[c:11](-[c:12]3[cH:13][cH:14][... | CS(=O)(=O)Cl.Cc1cccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3CO)n1 | CS(=O)(=O)OCC1CCc2c(-c3ccnc4ccccc34)c(-c3ccccn3)nn21 | null | CN(C1=CC=NC=C1)C | C(C)(=O)OCC.N1=CC=CC=C1 | Acylation | OtherReaction | d0ad6f15b22ea4b9634e4b23b1719f09a7708073ef5940eab5940de4a135e799 | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1ccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)nc1 | C-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[#7;a:6]-[C:7]-[C:8]-[OH;D1;+0:9].Cl-[S;H0;D4;+0:10](-[C;D1;H3:11])(=[O;D1;H0:12])=[O;D1;H0:13]>>[#7;a:6]-[C:7]-[C:8]-[O;H0;D2;+0:9]-[S;H0;D4;+0:10](-[C;D1;H3:11])(=[O;D1;H0:12])=[O;D1;H0:13].[c:3]:[#7;a:2]:[cH;D2;+0:1]:[c:4]:[c:5] | null | [] | null | null | 30 | MINUTE | A solution of [2-(6-methyl-pyridin-2-yl)-3-quinolin-4-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-6-yl]-methanol (30 mg, 0.07 mmol) and 4-dimethylaminopyridine (catalytic) in pyridine (0.2 mL) is cooled to 0° C. and treated with methanesulfonyl chloride (8 mL, 0.105 mmol) and stirred for 30 min. The mixture is stirred at r... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | c1ccncc1 | c1ccncc1 | c1ccc2ncccc2c1.c1ccncc1.c1cc2n(n1)CCC2 | HCl | CN(C1=CC=NC=C1)C.C(C)(=O)OCC.N1=CC=CC=C1 | null | 0.5 | CS(=O)(=O)Cl.Cc1cccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3CO)n1>CN(C1=CC=NC=C1)C.C(C)(=O)OCC.N1=CC=CC=C1>CS(=O)(=O)OCC1CCc2c(-c3ccnc4ccccc34)c(-c3ccccn3)nn21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fd12723f3bbf4a11a7f816b10ab4001b | CC(C)(C)OC(=O)N1CCC(Br)CC1.Oc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1>>CC(C)(C)OC(=O)N1CCC(Oc2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)CC1 | N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC(=CC=C21)O.C(C)(C)(C)OC(=O)N1CCC(CC1)Br.C([O-])([O-])=O.[Cs+].[Cs+]>>C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC=CC=C1)CCC2 | Br[CH:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:38][CH2:37]1.[OH:12][c:13]1[cH:14][cH:15][c:16]2[c:17](-[c:18]3[c:19](-[c:20]4[cH:21][cH:22][cH:23][cH:24][n:25]4)[n:26][n:27]4[c:28]3[CH2:29][CH2:30][CH2:31]4)[cH:32][cH:33][n:34][c:35]2[cH:36]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:... | CC(C)(C)OC(=O)N1CCC(Br)CC1.Oc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | CC(C)(C)OC(=O)N1CCC(Oc2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)CC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 520184604251fadd2e7ca0e6b22c68b2959d8c521e7b919c705c33a3a657175c | cf768afb66ed5041aefdce1fa6d1e40995a1ab7c4b4a4ca47544fe49ee1e629f | c1ccc(-c2nn3c(c2-c2ccnc4cc(OC5CCNCC5)ccc24)CCC3)nc1 | Br-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[#7;a:7]:[c:8]:[c:9]:[c:10](-[OH;D1;+0:11]):[c:12]>>[#7;a:7]:[c:8]:[c:9]:[c:10](-[O;H0;D2;+0:11]-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1):[c:12] | null | [] | 80 | CELSIUS | null | null | To a suspension of 4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-ol (0.27 g, 0.84 mmol) in N,N-dimethylformamide (15 mL) is added 4-bromo-piperidine-1-carboxylic acid tert-butyl ester (0.29 mL, 2.28 mmol) and cesium carbonate (1.5 g, 4.57 mmol. The mixture is heated at 80° C. for 48 h and conc... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic alcohol | Ether | C1CC[NH]CC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccncc1.c1cc2n(n1)CCC2.c1ccc2ncccc2c1 | HBr | CN(C=O)C | 80 | null | CC(C)(C)OC(=O)N1CCC(Br)CC1.Oc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1>CN(C=O)C>CC(C)(C)OC(=O)N1CCC(Oc2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-53a452ae6cce4174b0f114354aea1e18 | O=C1OCCn2nc(-c3ccccn3)c(-c3ccnc4ccccc34)c21>>OCCn1nc(-c2ccccn2)c(-c2ccnc3ccccc23)c1CO | N1=C(C=CC=C1)C1=NN2C(C(OCC2)=O)=C1C1=CC=NC2=CC=CC=C12.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>OCCN1N=C(C(=C1CO)C1=CC=NC2=CC=CC=C12)C1=NC=CC=C1 | [O:1]1[CH2:2][CH2:3][n:4]2[n:5][c:6](-[c:7]3[cH:8][cH:9][cH:10][cH:11][n:12]3)[c:13](-[c:14]3[cH:15][cH:16][n:17][c:18]4[cH:19][cH:20][cH:21][cH:22][c:23]34)[c:24]2[C:25]1=[O:26]>>[OH:1][CH2:2][CH2:3][n:4]1[n:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][n:12]2)[c:13](-[c:14]2[cH:15][cH:16][n:17][c:18]3[cH:19][cH:20][cH:21... | O=C1OCCn2nc(-c3ccccn3)c(-c3ccnc4ccccc34)c21 | OCCn1nc(-c2ccccn2)c(-c2ccnc3ccccc23)c1CO | null | null | O1CCCC1 | Reduction | OtherReaction | b6eaeb5935e4635f5fe693dc6dc29bbba88650e4c9fd915e5249ff3b52aa4ad3 | a3624cf369c1b01c8e22beb245d0aaa35dfcfbb232db9fd45f04a556bfa196ec | c1ccc(-c2n[nH]cc2-c2ccnc3ccccc23)nc1 | [O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[O;H0;D2;+0:3]-[C:4]-[C:5]-[#7;a:6]2:[#7;a:7]:[c:8]:[c:9]:[c:10]:2-1>>[OH;D1;+0:3]-[C:4]-[C:5]-[#7;a:6]1:[#7;a:7]:[c:8]:[c:9]:[c:10]:1-[CH2;D2;+0:2]-[OH;D1;+0:1] | null | [] | null | null | 2 | HOUR | To a solution of 2-pyridin-2-yl-3-quinolin-4-yl-pyrazolo[5,1-c]morpholin-4-one (0.50 g, 1.46 mmol) in tetrahydrofuran (20 mL) is added LiAlH4 (0.50 g, 13.1 mmol) at room temperature. The mixture is stirred for 2 h quenched with 1 N sodium hydroxide solution, and partitioned between dichloromethane and water. The organi... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol.Primary alcohol | c1cc2n(n1)CCOC2 | null | c1cn[nH]c1.c1ccncc1.c1ccc2ncccc2c1 | null | O1CCCC1 | null | 2 | O=C1OCCn2nc(-c3ccccn3)c(-c3ccnc4ccccc34)c21>O1CCCC1>OCCn1nc(-c2ccccn2)c(-c2ccnc3ccccc23)c1CO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c51fe6fbce314d199d31f9750821f276 | CCOC(=O)Cl.NN=C(Cc1ccnc2ccccc12)c1ccccn1>>Oc1[nH]nc(-c2ccccn2)c1-c1ccnc2ccccc12 | N1=C(C=CC=C1)C(CC1=CC=NC2=CC=CC=C12)=NN.ClC(=O)OCC>>N1=C(C=CC=C1)C=1C(=C(NN1)O)C1=CC=NC2=CC=CC=C12 | CCO[C:2](Cl)=[O:1].[NH2:3][N:4]=[C:5]([c:6]1[cH:7][cH:8][cH:9][cH:10][n:11]1)[CH2:12][c:13]1[cH:14][cH:15][n:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]12>>[OH:1][c:2]1[nH:3][n:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][n:11]2)[c:12]1-[c:13]1[cH:14][cH:15][n:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]12 | CCOC(=O)Cl.NN=C(Cc1ccnc2ccccc12)c1ccccn1 | Oc1[nH]nc(-c2ccccn2)c1-c1ccnc2ccccc12 | null | null | N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | b4a17acc65df6e86e016c101f7b0341241b272c4710bcd7445274210e9ae73ed | 4d54bd818747be6501481bd49f6f937f672611f124526aae384d41d887f203dd | c1ccc(-c2n[nH]cc2-c2ccnc3ccccc23)nc1 | C-C-O-[C;H0;D3;+0:1](-Cl)=[O;H0;D1;+0:2].[NH2;D1;+0:3]-[N;H0;D2;+0:4]=[C;H0;D3;+0:5](-[CH2;D2;+0:6]-[c;H0;D3;+0:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11](:[c:12]):[c:13]:1:[c:14])-[c;H0;D3;+0:15](:[#7;a:16]:[c:17]):[c:18]:[c:19]>>[OH;D1;+0:2]-[c;H0;D3;+0:1]1:[nH;D2;+0:3]:[n;H0;D2;+0:4]:[c;H0;D3;+0:5](-[c;H0;D3;+0:15](:[#7;a:16]... | null | [] | null | null | 2 | HOUR | To a solution of (1-pyridin-2-yl-2-quinolin-4-yl-ethylidene)-hydrazine (2.0 g, 7.6 mmol) in pyridine (20 mL) at 0° C. is added ethyl chloroformate (2 mL) dropwise. The mixture is warmed to room temperature and stirred for 2 h. The solution is refluxed for 12 h and concentrated in vacuo. The residue is treated with dich... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Hydrazone.Ether | Aromatic alcohol | null | c1cn[nH]c1 | c1cn[nH]c1.c1ccncc1.c1ccc2ncccc2c1 | HCl | N1=CC=CC=C1 | null | 2 | CCOC(=O)Cl.NN=C(Cc1ccnc2ccccc12)c1ccccn1>N1=CC=CC=C1>Oc1[nH]nc(-c2ccccn2)c1-c1ccnc2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-30f0c1b87db9430091f5e9eccc27e8b7 | CC(C)(N)CNC(=O)OC(C)(C)C.Cc1cccc(-c2nn3c(c2-c2ccnc4cc(C(=O)O)ccc24)CCC3)n1>>Cc1cccc(-c2nn3c(c2-c2ccnc4cc(C(=O)NC(C)(C)CNC(=O)OC(C)(C)C)ccc24)CCC3)n1 | CC1=CC=CC(=N1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC(=CC=C21)C(=O)O.C(C)(C)(C)OC(NCC(C)(C)N)=O.C(CCl)Cl.ON1N=NC2=C1C=CC=C2.C(C)(C)N(C(C)C)CC>>C(C)(C)(C)OC(NCC(C)(NC(=O)C1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC(=CC=C1)C)CCC2)C)=O | [NH2:21][C:22]([CH3:23])([CH3:24])[CH2:25][NH:26][C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33].O[C:19]([c:18]1[cH:17][c:16]2[n:15][cH:14][cH:13][c:12](-[c:11]3[c:7](-[c:6]4[cH:5][cH:4][cH:3][c:2]([CH3:1])[n:40]4)[n:8][n:9]4[c:10]3[CH2:37][CH2:38][CH2:39]4)[c:36]2[cH:35][cH:34]1)=[O:20]>>[CH3:1][c:2]1[cH:3][cH... | CC(C)(N)CNC(=O)OC(C)(C)C.Cc1cccc(-c2nn3c(c2-c2ccnc4cc(C(=O)O)ccc24)CCC3)n1 | Cc1cccc(-c2nn3c(c2-c2ccnc4cc(C(=O)NC(C)(C)CNC(=O)OC(C)(C)C)ccc24)CCC3)n1 | null | null | ClCCl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)nc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[c:6]:[#7;a:7].[C:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[NH2;D1;+0:12]>>[#7;a:7]:[c:6]:[c:5]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:12]-[C:9](-[C:8])(-[C;D1;H3:10])-[C;D1;H3:11]):[c:4] | 91 | [{"value": 91.0, "product": "C(C)(C)(C)OC(NCC(C)(NC(=O)C1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC(=CC=C1)C)CCC2)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.3, "product": "C(C)(C)(C)OC(NCC(C)(NC(=O)C1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC(=CC=C1)C)CCC2)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_des... | null | null | null | null | To a solution of 4-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinoline-7-carboxylic acid (0.16 g, 0.43 mmol), (2-amino-2-methyl-propyl)-carbamic acid tert-butyl ester (0.09 g, 0.47 mmol), EDC (0.09 g, 0.47 mmol), 1-hydroxybenzotriazole (0.06 g, 0.47 mmol) in dichloromethane (8.6 mL) is added... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccc2ncccc2c1.c1cc2n(n1)CCC2 | HO- | ClCCl | null | null | CC(C)(N)CNC(=O)OC(C)(C)C.Cc1cccc(-c2nn3c(c2-c2ccnc4cc(C(=O)O)ccc24)CCC3)n1>ClCCl>Cc1cccc(-c2nn3c(c2-c2ccnc4cc(C(=O)NC(C)(C)CNC(=O)OC(C)(C)C)ccc24)CCC3)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c500204820b146478e6852cd150b3ce0 | CC(C)(C)OC(=O)N1CCC(Br)CC1.Oc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1>>CC(C)(C)OC(=O)N1CCC(Oc2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)CC1 | N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC(=CC=C21)O.C(C)(C)(C)OC(=O)N1CCC(CC1)Br.C([O-])([O-])=O.[Cs+].[Cs+]>>C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC=CC=C1)CCC2 | Br[CH:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:38][CH2:37]1.[OH:12][c:13]1[cH:14][cH:15][c:16]2[c:17](-[c:18]3[c:19](-[c:20]4[cH:21][cH:22][cH:23][cH:24][n:25]4)[n:26][n:27]4[c:28]3[CH2:29][CH2:30][CH2:31]4)[cH:32][cH:33][n:34][c:35]2[cH:36]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:... | CC(C)(C)OC(=O)N1CCC(Br)CC1.Oc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | CC(C)(C)OC(=O)N1CCC(Oc2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)CC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 520184604251fadd2e7ca0e6b22c68b2959d8c521e7b919c705c33a3a657175c | cf768afb66ed5041aefdce1fa6d1e40995a1ab7c4b4a4ca47544fe49ee1e629f | c1ccc(-c2nn3c(c2-c2ccnc4cc(OC5CCNCC5)ccc24)CCC3)nc1 | Br-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[#7;a:7]:[c:8]:[c:9]:[c:10](-[OH;D1;+0:11]):[c:12]>>[#7;a:7]:[c:8]:[c:9]:[c:10](-[O;H0;D2;+0:11]-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1):[c:12] | null | [] | 80 | CELSIUS | null | null | To a suspension of 4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-ol (0.27 g, 0.84 mmol) in N,N-dimethylformamide (15 mL) is added 4-bromo-piperidine-1-carboxylic acid tert-butyl ester (0.29 mL, 2.28 mmol) and cesium carbonate (1.5 g, 4.57 mmol). The mixture is heated at 80° C. for 48 h and con... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic alcohol | Ether | C1CC[NH]CC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccncc1.c1cc2n(n1)CCC2.c1ccc2ncccc2c1 | HBr | CN(C=O)C | 80 | null | CC(C)(C)OC(=O)N1CCC(Br)CC1.Oc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1>CN(C=O)C>CC(C)(C)OC(=O)N1CCC(Oc2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7dc08d5b00874fdcadab0f0a65ef94c2 | CCOC(=O)COc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1>>O=C(O)COc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | C(C)OC(COC1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC=CC=C1)CCC2)=O.[OH-].[Li+]>>N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC(=CC=C21)OCC(=O)O | CC[O:3][C:2](=[O:1])[CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]2[c:10](-[c:11]3[c:12](-[c:13]4[cH:14][cH:15][cH:16][cH:17][n:18]4)[n:19][n:20]4[c:21]3[CH2:22][CH2:23][CH2:24]4)[cH:25][cH:26][n:27][c:28]2[cH:29]1>>[O:1]=[C:2]([OH:3])[CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]2[c:10](-[c:11]3[c:12](-[c:13]4[cH:14][cH:15][cH:16][cH:17][n... | CCOC(=O)COc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | O=C(O)COc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | null | null | CO | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)nc1 | 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 | [] | 60 | CELSIUS | null | null | To a solution of [4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-yloxy]-acetic acid ethyl ester (250 mg, 0.6 mmol) in methanol (4 mL) at room temperature is added 1 N lithium hydroxide (1.2 mL, 1.2 mmol). The mixture is heated at 60° C. for 4 h. The mixture is cooled to room temperature and con... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccncc1.c1cc2n(n1)CCC2.c1ccc2ncccc2c1 | Other | CO | 60 | null | CCOC(=O)COc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1>CO>O=C(O)COc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1f71017f179349fd95bf52de87aca6aa | CS(=O)(=O)OCC1CCCO1.Oc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1>>c1ccc(-c2nn3c(c2-c2ccnc4cc(OCC5CCCO5)ccc24)CCC3)nc1 | O1C(CCC1)COS(=O)(=O)C.N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC(=CC=C21)O.C([O-])([O-])=O.[Cs+].[Cs+]>>N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC(=CC=C21)OCC2OCCC2 | CS(=O)(=O)O[CH2:18][CH:19]1[CH2:20][CH2:21][CH2:22][O:23]1.[cH:1]1[cH:2][cH:3][c:4](-[c:5]2[n:6][n:7]3[c:8]([c:9]2-[c:10]2[cH:11][cH:12][n:13][c:14]4[cH:15][c:16]([OH:17])[cH:24][cH:25][c:26]24)[CH2:27][CH2:28][CH2:29]3)[n:30][cH:31]1>>[cH:1]1[cH:2][cH:3][c:4](-[c:5]2[n:6][n:7]3[c:8]([c:9]2-[c:10]2[cH:11][cH:12][n:13][... | CS(=O)(=O)OCC1CCCO1.Oc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | c1ccc(-c2nn3c(c2-c2ccnc4cc(OCC5CCCO5)ccc24)CCC3)nc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 57201f1afbda3b7775282ca8e3c59a4fb8e542f888bbdbfa994f08238598f88e | b300ae9ac00448343b04f8595ac10c40ddc175401f75ad1a9cb423839305bb59 | c1ccc(-c2nn3c(c2-c2ccnc4cc(OCC5CCCO5)ccc24)CCC3)nc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[C:3])-[#8:4]-[C:5].[#7;a:6]:[c:7]:[c:8]:[c:9](-[OH;D1;+0:10]):[c:11]>>[#7;a:6]:[c:7]:[c:8]:[c:9](-[O;H0;D2;+0:10]-[CH2;D2;+0:1]-[C:2](-[C:3])-[#8:4]-[C:5]):[c:11] | null | [] | 60 | CELSIUS | null | null | A mixture of methanesulfonic acid tetrahydro-furan-2-ylmethyl ester (0.70 g, 3.66 mmol), 4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-ol (400 mg, 1.22 mmol), and cesium carbonate (2.38 g, 7.32 mmol) in N,N-dimethylformamide (2.5 mL) is heated at 60° C. for 42 h. The mixture is concentrated in... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Aromatic alcohol | Ether | null | null | c1ccncc1.c1ccc2ncccc2c1.C1CCOC1.c1cc2n(n1)CCC2 | MsOH.HO- | CN(C=O)C | 60 | null | CS(=O)(=O)OCC1CCCO1.Oc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1>CN(C=O)C>c1ccc(-c2nn3c(c2-c2ccnc4cc(OCC5CCCO5)ccc24)CCC3)nc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-07ff4df06c1946268840014ad806ef34 | Cc1cccc(-c2nn3c(c2Br)CCC3)n1.OB(O)c1ccc2c(c1)OCO2>>Cc1cccc(-c2nn3c(c2-c2ccc4c(c2)OCO4)CCC3)n1 | BrC1=C2N(N=C1C1=NC(=CC=C1)C)CCC2.C1OC=2C=C(C=CC2O1)B(O)O.C([O-])([O-])=O.[Na+].[Na+]>>O1COC2=C1C=CC(=C2)C2=C1N(N=C2C2=NC(=CC=C2)C)CCC1 | Br[c:11]1[c:7](-[c:6]2[cH:5][cH:4][cH:3][c:2]([CH3:1])[n:24]2)[n:8][n:9]2[c:10]1[CH2:21][CH2:22][CH2:23]2.OB(O)[c:12]1[cH:13][cH:14][c:15]2[c:16]([cH:17]1)[O:18][CH2:19][O:20]2>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[n:8][n:9]3[c:10]([c:11]2-[c:12]2[cH:13][cH:14][c:15]4[c:16]([cH:17]2)[O:18][CH2:19][O:20]4)[CH2:2... | Cc1cccc(-c2nn3c(c2Br)CCC3)n1.OB(O)c1ccc2c(c1)OCO2 | Cc1cccc(-c2nn3c(c2-c2ccc4c(c2)OCO4)CCC3)n1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | CO.C1(=CC=CC=C1)C | C-C Coupling | Suzuki | 547d6a1aa040c11e6137f73f25d559d1db044b9c28918cbe5f8cefea2bb822bf | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2nn3c(c2-c2ccc4c(c2)OCO4)CCC3)nc1 | Br-[c;H0;D3;+0:1]1:[c:2](:[#7;a:3](:[#7;a:4]:[c:5]:1-[c:6]:[#7;a:7])-[C:8])-[C:9].O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]-[#8:15]>>[#7;a:7]:[c:6]-[c:5]1:[#7;a:4]:[#7;a:3](:[c:2](:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]-[#8:15])-[C:9])-[C:8] | null | [] | 80 | CELSIUS | null | null | A mixture of 3-bromo-2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole (99 mg, 0.36 mmol), 3,4-methylenedioxyphenylboronic acid (65 mg, 0.39 mmol), (PPh3)4Pd (20 mg, 0.02 mmol), 1 N aqueous sodium carbonate solution (500 μL, 0.5 mmol) in toluene (5 mL) and methanol (1 mL) is purged with argon for 10 min a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc2n(n1)CCC2.c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2.c1cc2n(n1)CCC2 | c1ccncc1.c1ccc2c(c1)OCO2.c1cc2n(n1)CCC2 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.CO.C1(=CC=CC=C1)C | 80 | null | Cc1cccc(-c2nn3c(c2Br)CCC3)n1.OB(O)c1ccc2c(c1)OCO2>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.CO.C1(=CC=CC=C1)C>Cc1cccc(-c2nn3c(c2-c2ccc4c(c2)OCO4)CCC3)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8a78da593f264a14928d76c76ca79538 | Brc1ccc2nccc(-c3c(-c4ccccn4)nn4c3CCC4)c2c1.CC(=O)[O-].[C]=O>>COC(=O)c1ccc2nccc(-c3c(-c4ccccn4)nn4c3CCC4)c2c1 | [C]=O.C(C)(=O)[O-].[Na+].C(Cl)Cl.BrC=1C=C2C(=CC=NC2=CC1)C1=C2N(N=C1C1=NC=CC=C1)CCC2>>COC(=O)C=1C=C2C(=CC=NC2=CC1)C1=C2N(N=C1C1=NC=CC=C1)CCC2 | Br[c:5]1[cH:6][cH:7][c:8]2[n:9][cH:10][cH:11][c:12](-[c:13]3[c:14](-[c:15]4[cH:16][cH:17][cH:18][cH:19][n:20]4)[n:21][n:22]4[c:23]3[CH2:24][CH2:25][CH2:26]4)[c:27]2[cH:28]1.C[C:1](=O)[O-:2].[C:3]=[O:4]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[n:9][cH:10][cH:11][c:12](-[c:13]3[c:14](-[c:15]4[cH:16][cH:17][cH:1... | Brc1ccc2nccc(-c3c(-c4ccccn4)nn4c3CCC4)c2c1.CC(=O)[O-].[C]=O | COC(=O)c1ccc2nccc(-c3c(-c4ccccn4)nn4c3CCC4)c2c1 | null | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2] | CO | Acylation | OtherReaction | 517dbf7fc76916843949fb6f3b9dc8b1e0a8f0d12377f500e01a11ea907bc352 | 843b64a5a526f70107d024a7003b94aa750190d2759e9e4e7ac8f05f2eb068bc | c1ccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)nc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1.C-[C;H0;D3;+0:8](=O)-[O-;H0;D1:9].[C;H0;D1;+0:10]=[O;D1;H0:11]>>[#7;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[C;H0;D3;+0:10](=[O;D1;H0:11])-[O;H0;D2;+0:9]-[CH3;D1;+0:8]):[c:7]:[c:6]:1 | null | [] | null | null | null | null | To a mixture of sodium acetate (0.84 g, 10.2 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II):CH2Cl2 (42 mg, 0.05 mmol) in methanol (40 mL) is added 6-bromo-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline (1.0 g, 2.56 mmol). The mixture is heated at 90° C. under 68 psi carbo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Ester | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccncc1.c1cc2n(n1)CCC2 | Br- | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].CO | null | null | Brc1ccc2nccc(-c3c(-c4ccccn4)nn4c3CCC4)c2c1.CC(=O)[O-].[C]=O>C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].CO>COC(=O)c1ccc2nccc(-c3c(-c4ccccn4)nn4c3CCC4)c2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-be7a79edca974d11a6f6a3374a17c190 | OCCn1nc(-c2ccccn2)c(-c2ccnc3ccccc23)c1CO>>c1ccc(-c2nn3c(c2-c2ccnc4ccccc24)COCC3)nc1 | OCCN1N=C(C(=C1CO)C1=CC=NC2=CC=CC=C12)C1=NC=CC=C1.[H-].[Na+].CS(=O)(=O)Cl>>N1=C(C=CC=C1)C1=NN2C(COCC2)=C1C1=CC=NC2=CC=CC=C12 | O[CH2:20][c:8]1[n:7]([CH2:23][CH2:22][OH:21])[n:6][c:5](-[c:4]2[cH:3][cH:2][cH:1][cH:25][n:24]2)[c:9]1-[c:10]1[cH:11][cH:12][n:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]12>>[cH:1]1[cH:2][cH:3][c:4](-[c:5]2[n:6][n:7]3[c:8]([c:9]2-[c:10]2[cH:11][cH:12][n:13][c:14]4[cH:15][cH:16][cH:17][cH:18][c:19]24)[CH2:20][O:21][CH2... | OCCn1nc(-c2ccccn2)c(-c2ccnc3ccccc23)c1CO | c1ccc(-c2nn3c(c2-c2ccnc4ccccc24)COCC3)nc1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 0e6cf42c40d22bccad91f2a43e43609397c1970fe5800c1f32bde0a3f162a581 | 31a44c623e879cda50fc3ef399266dde4d5f7d364c38209e2960d8959326fbb0 | c1ccc(-c2nn3c(c2-c2ccnc4ccccc24)COCC3)nc1 | O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6]:1-[C:7]-[C:8]-[OH;D1;+0:9]>>[#7;a:5]1:[c:4]:[c:3]:[c:2]2:[#7;a:6]:1-[C:7]-[C:8]-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-2 | null | [] | null | null | 2 | HOUR | To a solution of 2-(2-hydroxyethyl)-3-hydroxymethyl-5-pyridin-2-yl-4-quinoline-4-yl-pyrazole, (0.10 g, 0.29 mmol) in tetrahydrofuran (10 mL) cooled at 0° C. is added NaH (0.04 g, 50% in mineral oil). The mixture is stirred for 2 h at room temperature and methanesulfonyl chloride (0.065 g, 0.57 mmol) is added dropwise o... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Primary alcohol | Ether | null | c1cc2n(n1)CCOC2 | c1ccncc1.c1ccc2ncccc2c1.c1cc2n(n1)CCOC2 | HO- | O1CCCC1 | null | 2 | OCCn1nc(-c2ccccn2)c(-c2ccnc3ccccc23)c1CO>O1CCCC1>c1ccc(-c2nn3c(c2-c2ccnc4ccccc24)COCC3)nc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c379553fdac94f1c90f2ccafb8db9214 | CCOC(=O)c1n[nH]c(-c2ccccn2)c1-c1ccnc2ccccc12.OCCBr>>O=C1OCCn2nc(-c3ccccn3)c(-c3ccnc4ccccc34)c21 | C(C)(=O)OCC.C(C)OC(=O)C1=NNC(=C1C1=CC=NC2=CC=CC=C12)C1=NC=CC=C1.BrCCO.C([O-])([O-])=O.[Cs+].[Cs+]>>N1=C(C=CC=C1)C1=NN2C(C(OCC2)=O)=C1C1=CC=NC2=CC=CC=C12 | CCO[C:2](=[O:1])[c:26]1[n:6][nH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][cH:13][n:14]2)[c:15]1-[c:16]1[cH:17][cH:18][n:19][c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]12.Br[CH2:5][CH2:4][OH:3]>>[O:1]=[C:2]1[O:3][CH2:4][CH2:5][n:6]2[n:7][c:8](-[c:9]3[cH:10][cH:11][cH:12][cH:13][n:14]3)[c:15](-[c:16]3[cH:17][cH:18][n:19][c:20]4[... | CCOC(=O)c1n[nH]c(-c2ccccn2)c1-c1ccnc2ccccc12.OCCBr | O=C1OCCn2nc(-c3ccccn3)c(-c3ccnc4ccccc34)c21 | null | null | CN(C=O)C | Protection | OtherReaction | f07a6125683b23f55df2796db03f5b5477d0172340fd987ee9bc7e1e535e7a62 | 6557a2049eaf1855ef9de5f364d31f6ceb45f92752d1dd754188a1245824b29b | O=C1OCCn2nc(-c3ccccn3)c(-c3ccnc4ccccc34)c21 | Br-[CH2;D2;+0:1]-[C:2]-[OH;D1;+0:3].C-C-O-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6]1:[c:7]:[c:8](-[c:9]:[#7;a:10]):[nH;D2;+0:11]:[n;H0;D2;+0:12]:1>>[#7;a:10]:[c:9]-[c:8]1:[c:7]:[c:6]2:[n;H0;D3;+0:12](:[n;H0;D2;+0:11]:1)-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-[C;H0;D3;+0:4]-2=[O;D1;H0:5] | null | [] | 60 | CELSIUS | null | null | A mixture of 3-ethoxycarbonyl-5-pyridin-2-yl-4-quinolin-4-yl-pyrazole (0.35 g, 1.00 mmol), 2-bromoethanol (0.15 g, 1.12 mmol), and cesium carbonate (0.50 g, 1.5 mmol) in N,N-dimethylformamide (20 mL) is heated at 60° C. for 2 h. The mixture is cooled to room temperature and poured into ethyl acetate (60 mL). The organi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Primary alcohol | Ester | c1cn[nH]c1 | c1cc2n(n1)CCOC2 | c1cc2n(n1)CCOC2.c1ccncc1.c1ccc2ncccc2c1 | HBr | CN(C=O)C | 60 | null | CCOC(=O)c1n[nH]c(-c2ccccn2)c1-c1ccnc2ccccc12.OCCBr>CN(C=O)C>O=C1OCCn2nc(-c3ccccn3)c(-c3ccnc4ccccc34)c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2037d4dea16e4b4ca6ee4112e129ee14 | CNC.ClCCCOc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1>>CN(C)CCCOc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | ClCCCOC1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC=CC=C1)CCC2.[I-].[Na+].CNC.O1CCCC1>>CN(CCCOC1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC=CC=C1)CCC2)C | [CH3:1][NH:2][CH3:3].Cl[CH2:4][CH2:5][CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]2[c:12](-[c:13]3[c:14](-[c:15]4[cH:16][cH:17][cH:18][cH:19][n:20]4)[n:21][n:22]4[c:23]3[CH2:24][CH2:25][CH2:26]4)[cH:27][cH:28][n:29][c:30]2[cH:31]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]2[c:12](-[c:13]3[c:14](-... | CNC.ClCCCOc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | CN(C)CCCOc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)nc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[NH;D2;+0:5]-[C;D1;H3:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:5](-[C;D1;H3:4])-[C;D1;H3:6] | null | [] | null | null | null | null | A solution of 7-(3-chloro-propoxy)-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline (54 mg, 0.13 mmol), sodium iodide (5 mg, 0.03 mmol), and 2 N dimethylamine in tetrahydrofuran (3 mL, 6 mmol) in N,N-dimethylformamide (5 mL) is heated at 100° C. for 48 h. The mixture is cooled and concentrated in ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1ccncc1.c1cc2n(n1)CCC2.c1ccc2ncccc2c1 | HCl | CN(C=O)C | null | null | CNC.ClCCCOc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1>CN(C=O)C>CN(C)CCCOc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a2755ef9035543b8ab8943dbf0a2beed | O=C1c2ccccc2C(=O)N1CCCBr.Oc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1>>O=C1c2ccccc2C(=O)N1CCCOc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC(=CC=C21)O.BrCCCN1C(C=2C(C1=O)=CC=CC2)=O.C([O-])([O-])=O.[Cs+].[Cs+]>>N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC(=CC=C21)OCCCN2C(C1=CC=CC=C1C2=O)=O | Br[CH2:14][CH2:13][CH2:12][N:11]1[C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9]1=[O:10].[OH:15][c:16]1[cH:17][cH:18][c:19]2[c:20](-[c:21]3[c:22](-[c:23]4[cH:24][cH:25][cH:26][cH:27][n:28]4)[n:29][n:30]4[c:31]3[CH2:32][CH2:33][CH2:34]4)[cH:35][cH:36][n:37][c:38]2[cH:39]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:... | O=C1c2ccccc2C(=O)N1CCCBr.Oc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | O=C1c2ccccc2C(=O)N1CCCOc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | null | null | O.CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C1c2ccccc2C(=O)N1CCCOc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#7;a:4]:[c:5]:[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[#7;a:4]:[c:5]:[c:6]:[c:7](-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[C:2]-[C:3]):[c:9] | null | [] | 60 | CELSIUS | null | null | 4-(2-Pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-ol (0.100 g, 0.305 mmol), N-(3-bromopropyl)-phthalimide (0.163 g, 0.609 mmol, 2.0 equiv) and cesium carbonate (0.248 g, 0.761 mmol, 2.50 equiv) are combined in N,N-dimethylformamide (1.0 mL) and the reaction is heated at 60° C. for 48 hours. The re... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2c(c1)C[NH]C2.c1ccncc1.c1cc2n(n1)CCC2.c1ccc2ncccc2c1 | HBr | O.CN(C=O)C | 60 | null | O=C1c2ccccc2C(=O)N1CCCBr.Oc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1>O.CN(C=O)C>O=C1c2ccccc2C(=O)N1CCCOc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ba620833bb654b8b8301ec37ef3e1997 | O=C1CC[C@H](CO)N1.Oc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1>>O=C1CCC(COc2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)N1 | N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC(=CC=C21)O.OC[C@H]1CCC(N1)=O.CS(=O)(=O)Cl>>N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC(=CC=C21)OCC2CCC(N2)=O | O[CH2:6][C@H:5]1[CH2:4][CH2:3][C:2](=[O:1])[NH:32]1.[OH:7][c:8]1[cH:9][cH:10][c:11]2[c:12](-[c:13]3[c:14](-[c:15]4[cH:16][cH:17][cH:18][cH:19][n:20]4)[n:21][n:22]4[c:23]3[CH2:24][CH2:25][CH2:26]4)[cH:27][cH:28][n:29][c:30]2[cH:31]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([CH2:6][O:7][c:8]2[cH:9][cH:10][c:11]3[c:12](-[c:13]4[... | O=C1CC[C@H](CO)N1.Oc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | O=C1CCC(COc2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)N1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | O=C1CCC(COc2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)N1 | O-[CH2;D2;+0:1]-[C@@H;D3;+0:2]1-[#7:3]-[C:4](=[O;D1;H0:5])-[C:6]-[C:7]-1.[#7;a:8]:[c:9]:[c:10]:[c:11](-[OH;D1;+0:12]):[c:13]>>[#7;a:8]:[c:9]:[c:10]:[c:11](-[O;H0;D2;+0:12]-[CH2;D2;+0:1]-[CH;D3;+0:2]1-[#7:3]-[C:4](=[O;D1;H0:5])-[C:6]-[C:7]-1):[c:13] | null | [] | 60 | CELSIUS | 16 | HOUR | A solution of (R)-(−)-5-(hydroxymethyl)-2-pyrrolidinone (315 mg, 2.74 mmol) in N,N-dimethylformamide (3 mL) is treated with methansulfonyl chloride (320 mg, 2.74 mmol) and heated at 60° C. for 5 h. The reaction mixture is diluted with N,N-dimethylformamide (1 mL) and 4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyraz... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | C1CCNC1.c1ccncc1.c1cc2n(n1)CCC2.c1ccc2ncccc2c1 | HO- | CN(C=O)C | 60 | 16 | O=C1CC[C@H](CO)N1.Oc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1>CN(C=O)C>O=C1CCC(COc2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e7e385e0055b4b74a462f5b25feca342 | C=CC(=O)OC.Cc1cccc(-c2nn3c(c2-c2ccnc4cc(Br)ccc24)CCC3)n1>>COC(=O)C=Cc1ccc2c(-c3c(-c4cccc(C)n4)nn4c3CCC4)ccnc2c1 | C1(=C(C=CC=C1)P(C1=C(C=CC=C1)C)C1=C(C=CC=C1)C)C.C1(=C(C=CC=C1)P(C1=C(C=CC=C1)C)C1=C(C=CC=C1)C)C.BrC1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC(=CC=C1)C)CCC2.C(CCC)N(CCCC)CCCC.C(C=C)(=O)OC>>COC(C=CC1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC(=CC=C1)C)CCC2)=O | [CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH2:6].Br[c:7]1[cH:8][cH:9][c:10]2[c:11](-[c:12]3[c:13](-[c:14]4[cH:15][cH:16][cH:17][c:18]([CH3:19])[n:20]4)[n:21][n:22]4[c:23]3[CH2:24][CH2:25][CH2:26]4)[cH:27][cH:28][n:29][c:30]2[cH:31]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH:6][c:7]1[cH:8][cH:9][c:10]2[c:11](-[c:12]3[c:13](-[c:14]4[c... | C=CC(=O)OC.Cc1cccc(-c2nn3c(c2-c2ccnc4cc(Br)ccc24)CCC3)n1 | COC(=O)C=Cc1ccc2c(-c3c(-c4cccc(C)n4)nn4c3CCC4)ccnc2c1 | null | CC(=O)[O-].CC(=O)[O-].[Pd+2].CC(=O)[O-].CC(=O)[O-].[Pd+2] | CN(C=O)C.C1(=CC=CC=C1)C | C-C Coupling | Heck terminal vinyl | a87d881b4c1880689693d296001ccd251ba98c523b412e68ce627333ac531f30 | 4b186811a4930853b446d93d9faa39b267bddb9ce0b8021bda5c5a3b2bc69f0b | c1ccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)nc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[#7;a:4]:[c:5]):[c:6]:[c:7]:[c:8]:1.[C;D1;H3:9]-[#8:10]-[C:11](=[O;D1;H0:12])-[C:13]=[CH2;D1;+0:14]>>[C;D1;H3:9]-[#8:10]-[C:11](=[O;D1;H0:12])-[C:13]=[CH;D2;+0:14]-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[#7;a:4]:[c:5]):[c:6]:[c:7]:[c:8]:1 | null | [] | 80 | CELSIUS | 24 | HOUR | Nitrogen is bubbled through a solution of 7-bromo-4-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinoline (0.050 g, 0.12 mmol), tributylamine (0.032 mL, 0.17 mmol), methyl acrylate (0.027 mL, 0.24 mmol), and N,N-dimethylformamide (0.5 mL) in toluene (1.0 mL) for 20 min. Pd(OAc)2 (0.002 g, 0.00... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Vinyl | null | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccncc1.c1cc2n(n1)CCC2.c1ccc2ncccc2c1 | HBr | CC(=O)[O-].CC(=O)[O-].[Pd+2].CC(=O)[O-].CC(=O)[O-].[Pd+2].CN(C=O)C.C1(=CC=CC=C1)C | 80 | 24 | C=CC(=O)OC.Cc1cccc(-c2nn3c(c2-c2ccnc4cc(Br)ccc24)CCC3)n1>CC(=O)[O-].CC(=O)[O-].[Pd+2].CC(=O)[O-].CC(=O)[O-].[Pd+2].CN(C=O)C.C1(=CC=CC=C1)C>COC(=O)C=Cc1ccc2c(-c3c(-c4cccc(C)n4)nn4c3CCC4)ccnc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c897dfbfc774455391dabcde64d6a518 | CCCC[C]([Sn])=C(CCCC)CCCC.Cc1cccc(-c2nn3c(c2-c2ccnc4cc(Br)ccc24)CCC3)n1>>C=Cc1ccc2c(-c3c(-c4cccc(C)n4)nn4c3CCC4)ccnc2c1 | BrC1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC(=CC=C1)C)CCC2.C(CCC)C(=C(CCCC)CCCC)[Sn]>>CC1=CC=CC(=N1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC(=CC=C21)C=C | CCCC[C]([Sn])=[C:2](CCCC)[CH2:1]CCC.Br[c:3]1[cH:4][cH:5][c:6]2[c:7](-[c:8]3[c:9](-[c:10]4[cH:11][cH:12][cH:13][c:14]([CH3:15])[n:16]4)[n:17][n:18]4[c:19]3[CH2:20][CH2:21][CH2:22]4)[cH:23][cH:24][n:25][c:26]2[cH:27]1>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]2[c:7](-[c:8]3[c:9](-[c:10]4[cH:11][cH:12][cH:13][c:14]([CH3:15])[... | CCCC[C]([Sn])=C(CCCC)CCCC.Cc1cccc(-c2nn3c(c2-c2ccnc4cc(Br)ccc24)CCC3)n1 | C=Cc1ccc2c(-c3c(-c4cccc(C)n4)nn4c3CCC4)ccnc2c1 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | ca61f9c8b43a7b861326ca1ef93def85a8a5caecd0553fc9152ea70cd8e2530b | 27ac22ec7469bd7f39cc3c50746346e388051103704091d8380f391d425a4ebf | c1ccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)nc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[#7;a:4]:[c:5]):[c:6]:[c:7]:[c:8]:1.C-C-C-C-[C;H0;D3;+0:9](-[CH2;D2;+0:10]-C-C-C)=[C](-[Sn])-C-C-C-C>>[CH2;D1;+0:10]=[CH;D2;+0:9]-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[#7;a:4]:[c:5]):[c:6]:[c:7]:[c:8]:1 | null | [] | 90 | CELSIUS | null | null | Nitrogen is bubbled through a solution of 7-bromo-4-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinoline (0.050 g, 0.14 mmol) and tributylvinyltin (0.079 mL, 0.22 mmol) in toluene (2.0 mL) for 20 min. Pd(PPh3)2Cl2 is added and nitrogen bubbled through the reaction mixture for another 10 min. ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Vinyl | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccncc1.c1cc2n(n1)CCC2.c1ccc2ncccc2c1 | HBr.Sn | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.C1(=CC=CC=C1)C | 90 | null | CCCC[C]([Sn])=C(CCCC)CCCC.Cc1cccc(-c2nn3c(c2-c2ccnc4cc(Br)ccc24)CCC3)n1>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.C1(=CC=CC=C1)C>C=Cc1ccc2c(-c3c(-c4cccc(C)n4)nn4c3CCC4)ccnc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-12f27f75f99d47e4a40c92fcb9b23588 | Brc1cccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)n1.[Cl][Mg][CH2]c1ccccc1>>c1ccc(Cc2cccc(-c3nn4c(c3-c3ccnc5ccccc35)CCC4)n2)cc1 | C(C1=CC=CC=C1)[Mg]Cl.BrC1=CC=CC(=N1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC=CC=C21>>C(C1=CC=CC=C1)C1=CC=CC(=N1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC=CC=C21 | Br[c:6]1[cH:7][cH:8][cH:9][c:10](-[c:11]2[n:12][n:13]3[c:14]([c:15]2-[c:16]2[cH:17][cH:18][n:19][c:20]4[cH:21][cH:22][cH:23][cH:24][c:25]24)[CH2:26][CH2:27][CH2:28]3)[n:29]1.[Cl][Mg][CH2:5][c:4]1[cH:3][cH:2][cH:1][cH:31][cH:30]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][c:6]2[cH:7][cH:8][cH:9][c:10](-[c:11]3[n:12][n:13]4[c:14]... | Brc1cccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)n1.[Cl][Mg][CH2]c1ccccc1 | c1ccc(Cc2cccc(-c3nn4c(c3-c3ccnc5ccccc35)CCC4)n2)cc1 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cl-].[Zn+2].[Cl-] | O1CCCC1 | C-C Coupling | OtherReaction | f9b2f4479b8b6c16ab97e2edf92167aac959f81f2164feea9937b72c55f0512b | 7eab41b7d498a9b6e898b07b0e0d9b3528044390091411fce2a435b647d0bc46 | c1ccc(Cc2cccc(-c3nn4c(c3-c3ccnc5ccccc35)CCC4)n2)cc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[Cl]-[Mg]-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9]):[c:4]:[c:5] | null | [] | null | null | 15 | MINUTE | Zinc(II) chloride (0.34 mL, 1.0 M solution, 0.34 mmol) is added, at room temperature with stirring, to a solution of benzyl magnesium chloride (0.15 mL, 2.0 M solution, 0.31 mmol) in tetrahydrofuran (1 mL). After 15 min, Pd(PPh3)2Cl2 (5.4 mg, 0.0076 mmol) is added followed by a solution of 4-[2-(6-bromo-pyridin-2-yl)-5... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Aromatic halide | null | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccc2ncccc2c1.c1cc2n(n1)CCC2 | Br-.Mg | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cl-].[Zn+2].[Cl-].O1CCCC1 | null | 0.25 | Brc1cccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)n1.[Cl][Mg][CH2]c1ccccc1>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cl-].[Zn+2].[Cl-].O1CCCC1>c1ccc(Cc2cccc(-c3nn4c(c3-c3ccnc5ccccc35)CCC4)n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2b84cbe4087445e9a83ca73bab924620 | CCOC(=O)c1ccc2c(-c3c(-c4cccc(C)n4)nn4c3CCC4)ccnc2c1>>Cc1cccc(-c2nn3c(c2-c2ccnc4cc(C(=O)O)ccc24)CCC3)n1 | C(C)OC(=O)C1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC(=CC=C1)C)CCC2.[OH-].[Li+]>>CC1=CC=CC(=N1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC(=CC=C21)C(=O)O | CC[O:21][C:19]([c:18]1[cH:17][c:16]2[n:15][cH:14][cH:13][c:12](-[c:11]3[c:7](-[c:6]4[cH:5][cH:4][cH:3][c:2]([CH3:1])[n:28]4)[n:8][n:9]4[c:10]3[CH2:25][CH2:26][CH2:27]4)[c:24]2[cH:23][cH:22]1)=[O:20]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[n:8][n:9]3[c:10]([c:11]2-[c:12]2[cH:13][cH:14][n:15][c:16]4[cH:17][c:18]([C... | CCOC(=O)c1ccc2c(-c3c(-c4cccc(C)n4)nn4c3CCC4)ccnc2c1 | Cc1cccc(-c2nn3c(c2-c2ccnc4cc(C(=O)O)ccc24)CCC3)n1 | null | null | CO | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)nc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | 60 | CELSIUS | null | null | To a solution of 4-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinoline-7-carboxylic acid ethyl ester (250 mg, 0.6 mmol) in methanol (4 mL) at room temperature is added 1 N lithium hydroxide (1.2 mL, 1.2 mmol). The mixture is heated at 60° C. for 4 h. The mixture is cooled to room temperature... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccncc1.c1ccc2ncccc2c1.c1cc2n(n1)CCC2 | Other | CO | 60 | null | CCOC(=O)c1ccc2c(-c3c(-c4cccc(C)n4)nn4c3CCC4)ccnc2c1>CO>Cc1cccc(-c2nn3c(c2-c2ccnc4cc(C(=O)O)ccc24)CCC3)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7e43ca3ac0294abfb9cc8c732e641078 | NC1CCCC1.O=C(O)c1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1>>O=C(NC1CCCC1)c1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | Cl.CN(CCCN=C=NCC)C.C=1C=CC2=C(C1)N=NN2O.C1(CCCC1)N.N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC(=CC=C21)C(=O)O>>C1(CCCC1)NC(=O)C1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC=CC=C1)CCC2 | [NH2:3][CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8]1.O[C:2](=[O:1])[c:9]1[cH:10][cH:11][c:12]2[c:13](-[c:14]3[c:15](-[c:16]4[cH:17][cH:18][cH:19][cH:20][n:21]4)[n:22][n:23]4[c:24]3[CH2:25][CH2:26][CH2:27]4)[cH:28][cH:29][n:30][c:31]2[cH:32]1>>[O:1]=[C:2]([NH:3][CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8]1)[c:9]1[cH:10][cH:11][c:12]2[c:1... | NC1CCCC1.O=C(O)c1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | O=C(NC1CCCC1)c1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | null | null | ClCCl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NC1CCCC1)c1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[c:6]:[#7;a:7].[C:8]-[C:9](-[NH2;D1;+0:10])-[C:11]>>[#7;a:7]:[c:6]:[c:5]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[C:9](-[C:8])-[C:11]):[c:4] | null | [] | null | null | 18 | HOUR | A mixture of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, (53 mg, 0.30 mmol), HOBT, (24 mg, 0.28 mmol), cyclopentylamine (0.03 mL, 0.30 mmol), and 4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline-7-carboxylic acid (90 mg, 0.25 mmol) in dichloromethane (1 mL) is stirred room tempera... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CCCC1.c1ccncc1.c1cc2n(n1)CCC2.c1ccc2ncccc2c1 | HO- | ClCCl | null | 18 | NC1CCCC1.O=C(O)c1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1>ClCCl>O=C(NC1CCCC1)c1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3de5308c4fcb4270b00c547ea313c58d | O=C(Cl)C(=O)Cl.O=C(O)COc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1>>O=C(Cl)COc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC(=CC=C21)OCC(=O)O.C(C(=O)Cl)(=O)Cl>>N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC(=CC=C21)OCC(=O)Cl | O=C(Cl)C(=O)[Cl:3].O[C:2](=[O:1])[CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]2[c:10](-[c:11]3[c:12](-[c:13]4[cH:14][cH:15][cH:16][cH:17][n:18]4)[n:19][n:20]4[c:21]3[CH2:22][CH2:23][CH2:24]4)[cH:25][cH:26][n:27][c:28]2[cH:29]1>>[O:1]=[C:2]([Cl:3])[CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]2[c:10](-[c:11]3[c:12](-[c:13]4[cH:14][cH:15][cH... | O=C(Cl)C(=O)Cl.O=C(O)COc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | O=C(Cl)COc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | null | CN(C=O)C | ClCCl | Functional Group Interconversion | Alcohol to chloride_Other | 013cec2edeb273a7a148f349d36a52d99ff4e7bcf8eed78085df830088e387ac | aedb1f68dc5b7eb0583043e1125b741382b17974140a2f46554f0110e2ddc884 | c1ccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)nc1 | Cl-C(=O)-C(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]-[#8:5]>>[#8:5]-[C:4]-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3] | null | [] | null | null | 5 | HOUR | To a solution of [4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-yloxy]-acetic acid (150 mg, 0.39 mmol) in dichloromethane (3 mL) is added oxalyl chloride (490 mg, 3.9 mmol) and 1 drop of N,N-dimethylformamide. The mixture is stirred at room temperature for 5 h, concentrated in vacuo, and resid... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Carboxylic acid | Acyl halide | null | null | c1ccncc1.c1cc2n(n1)CCC2.c1ccc2ncccc2c1 | HCl | CN(C=O)C.ClCCl | null | 5 | O=C(Cl)C(=O)Cl.O=C(O)COc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1>CN(C=O)C.ClCCl>O=C(Cl)COc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4b6bad24d7774a1ebf5c4e999f5f4b57 | CN1CCNCC1.O=C(Cl)COc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1>>CN1CCN(C(=O)COc2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)CC1 | N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC(=CC=C21)OCC(=O)Cl.CN1CCNCC1>>CN1CCN(CC1)C(COC1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC=CC=C1)CCC2)=O | [CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:34][CH2:35]1.Cl[C:6](=[O:7])[CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]2[c:14](-[c:15]3[c:16](-[c:17]4[cH:18][cH:19][cH:20][cH:21][n:22]4)[n:23][n:24]4[c:25]3[CH2:26][CH2:27][CH2:28]4)[cH:29][cH:30][n:31][c:32]2[cH:33]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[CH2:8][O:9][c:10]2... | CN1CCNCC1.O=C(Cl)COc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | CN1CCN(C(=O)COc2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)CC1 | null | null | ClCCl | Acylation | N-alkylation of secondary amines with alkyl halides | 008ee4368afbd52034630a2410a1738f53049b314574435184e4e0be81b96642 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(COc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1)N1CCNCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[#8:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1 | null | [] | null | null | 2.5 | HOUR | To a solution of [4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-yloxy]-acetic acid (150 mg, 0.39 mmol) in dichloromethane (3 mL) is added oxalyl chloride (490 mg, 3.9 mmol) and 1 drop of N,N-dimethylformamide. The mixture is stirred at room temperature for 5 h, concentrated in vacuo, and resid... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccncc1.c1cc2n(n1)CCC2.c1ccc2ncccc2c1 | HCl | ClCCl | null | 2.5 | CN1CCNCC1.O=C(Cl)COc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1>ClCCl>CN1CCN(C(=O)COc2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e9568a52249c4b2fbdc93d52e5bffe68 | CN(C)CC(=O)Cl.Nc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1>>CN(C)CC(=O)Nc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | C([O-])(O)=O.[Na+].CN(C)CC(=O)Cl.N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC(=CC=C21)N>>CN(CC(=O)NC1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC=CC=C1)CCC2)C | Cl[C:5]([CH2:4][N:2]([CH3:1])[CH3:3])=[O:6].[NH2:7][c:8]1[cH:9][cH:10][c:11]2[c:12](-[c:13]3[c:14](-[c:15]4[cH:16][cH:17][cH:18][cH:19][n:20]4)[n:21][n:22]4[c:23]3[CH2:24][CH2:25][CH2:26]4)[cH:27][cH:28][n:29][c:30]2[cH:31]1>>[CH3:1][N:2]([CH3:3])[CH2:4][C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][c:11]2[c:12](-[c:13]3[c:14]... | CN(C)CC(=O)Cl.Nc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | CN(C)CC(=O)Nc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | null | null | N1=CC=CC=C1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)nc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4].[#7;a:5]:[c:6]:[c:7]:[c:8](-[NH2;D1;+0:9]):[c:10]>>[#7:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[c:8](:[c:10]):[c:7]:[c:6]:[#7;a:5] | null | [] | null | null | null | null | A mixture of dimethylamino-acetyl chloride (620.0 mg, 13.33 mmol), 4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-ylamine (75 mg, 0.23 mmol), and 4-N,N-dimethylaminopyridine (10.2 mg, 0.09 mmol) in dry pyridine (1 mL) is refluxed for 72 h. The mixture is treated with saturated sodium bicarbonat... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1.c1cc2n(n1)CCC2.c1ccc2ncccc2c1 | HCl | N1=CC=CC=C1 | null | null | CN(C)CC(=O)Cl.Nc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1>N1=CC=CC=C1>CN(C)CC(=O)Nc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b587c4a0071e4ce489f217f216631641 | Brc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1.C[CH](C)[Mg][Cl]>>CC(C)c1cc(-c2c(-c3ccccn3)nn3c2CCC3)c2ccc(Br)cc2n1 | C(C)(C)[Mg]Cl.BrC1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC=CC=C1)CCC2.C(C)N(CC)CC.CS(=O)(=O)Cl>>BrC1=CC=C2C(=CC(=NC2=C1)C(C)C)C1=C2N(N=C1C1=NC=CC=C1)CCC2 | [cH:4]1[cH:5][c:6](-[c:7]2[c:8](-[c:9]3[cH:10][cH:11][cH:12][cH:13][n:14]3)[n:15][n:16]3[c:17]2[CH2:18][CH2:19][CH2:20]3)[c:21]2[cH:22][cH:23][c:24]([Br:25])[cH:26][c:27]2[n:28]1.[Cl][Mg][CH:2]([CH3:1])[CH3:3]>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][c:6](-[c:7]2[c:8](-[c:9]3[cH:10][cH:11][cH:12][cH:13][n:14]3)[n:15][n:16]3... | Brc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1.C[CH](C)[Mg][Cl] | CC(C)c1cc(-c2c(-c3ccccn3)nn3c2CCC3)c2ccc(Br)cc2n1 | null | null | O.O1CCCC1 | C-C Coupling | OtherReaction | 0071d8bd31a0025a6f0d3de986f7143c0c016889a482626ef3e3873cc4cfae78 | 8bca8ca721f0288f0875e75b7f264133e86623956746bda21982177c5da407f2 | c1ccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)nc1 | [C;D1;H3:1]-[CH;D3;+0:2](-[C;D1;H3:3])-[Mg]-[Cl].[c:4]:[#7;a:5]:[cH;D2;+0:6]:[c:7]:[c:8]>>[C;D1;H3:1]-[CH;D3;+0:2](-[C;D1;H3:3])-[c;H0;D3;+0:6](:[#7;a:5]:[c:4]):[c:7]:[c:8] | null | [] | -78 | CELSIUS | 2 | HOUR | A 2 M solution of isopropyl magnesium chloride in tetrahydrofuran (65 μL, 0.13 mmol) is added to solution of 7-bromo-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline (50.0 mg, 0.13 mmol) in tetrahydrofuran (1 mL) at room, temperature with stirring for 2 h. The mixture is cooled to −78° C. and trie... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide | null | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccncc1.c1cc2n(n1)CCC2.c1ccc2ncccc2c1 | HCl.Mg | O.O1CCCC1 | -78 | 2 | Brc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1.C[CH](C)[Mg][Cl]>O.O1CCCC1>CC(C)c1cc(-c2c(-c3ccccn3)nn3c2CCC3)c2ccc(Br)cc2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cb9b6c262d904ba286a664c696baaedc | Cc1ccccc1S(=O)(=O)Cl.OCCCSc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1>>ClCCCSc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC(=CC=C21)SCCCO.C=1(C(=CC=CC1)S(=O)(=O)Cl)C.C([O-])(O)=O.[Na+]>>ClCCCSC1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC=CC=C1)CCC2 | Cc1ccccc1S(=O)(=O)[Cl:1].O[CH2:2][CH2:3][CH2:4][S:5][c:6]1[cH:7][cH:8][c:9]2[c:10](-[c:11]3[c:12](-[c:13]4[cH:14][cH:15][cH:16][cH:17][n:18]4)[n:19][n:20]4[c:21]3[CH2:22][CH2:23][CH2:24]4)[cH:25][cH:26][n:27][c:28]2[cH:29]1>>[Cl:1][CH2:2][CH2:3][CH2:4][S:5][c:6]1[cH:7][cH:8][c:9]2[c:10](-[c:11]3[c:12](-[c:13]4[cH:14][c... | Cc1ccccc1S(=O)(=O)Cl.OCCCSc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | ClCCCSc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | null | null | N1=CC=CC=C1 | Functional Group Interconversion | Alcohol to chloride_sulfonyl chloride | f0b80ccbf0001ae0965c62d59e0826b6dbda23f9c7301586520c7d9ce64eea5a | d5d71bad4297b1f4f93dd1d1d9cddf0bb6fadb3f4dca1f84369c4074a39097d6 | c1ccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)nc1 | C-c1:c:c:c:c:c:1-S(=O)(=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 | [] | null | null | 72 | HOUR | To a solution of Preparation #21, 3-[4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-ylsulfanyl]-propan-1-ol (25.0 mg, 0.062 mmol) in dry pyridine (0.1 mL) is added toluene sulfonyl chloride (60.0 mg, 0.31 mmol) and the resulting mixture stirred at room temperature for 72 h. Saturated sodium bic... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Primary halide | c1ccccc1 | null | c1ccncc1.c1cc2n(n1)CCC2.c1ccc2ncccc2c1 | HO- | N1=CC=CC=C1 | null | 72 | Cc1ccccc1S(=O)(=O)Cl.OCCCSc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1>N1=CC=CC=C1>ClCCCSc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5117de9338de4a369384dbd7fc1bb107 | Brc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1.O=S(=O)(Cl)Cl>>ClC1CCn2nc(-c3ccccn3)c(-c3ccnc4cc(Br)ccc34)c21 | S(=O)(=O)(Cl)Cl.ClCCl.BrC1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC=CC=C1)CCC2>>BrC1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC=CC=C1)CCC2Cl | [CH2:2]1[CH2:3][CH2:4][n:5]2[n:6][c:7](-[c:8]3[cH:9][cH:10][cH:11][cH:12][n:13]3)[c:14](-[c:15]3[cH:16][cH:17][n:18][c:19]4[cH:20][c:21]([Br:22])[cH:23][cH:24][c:25]34)[c:26]21.O=S(=O)(Cl)[Cl:1]>>[Cl:1][CH:2]1[CH2:3][CH2:4][n:5]2[n:6][c:7](-[c:8]3[cH:9][cH:10][cH:11][cH:12][n:13]3)[c:14](-[c:15]3[cH:16][cH:17][n:18][c:... | Brc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1.O=S(=O)(Cl)Cl | ClC1CCn2nc(-c3ccccn3)c(-c3ccnc4cc(Br)ccc34)c21 | null | null | N1=CC=CC=C1 | Functional Group Interconversion | Chlorination | 144241665da317df64bdb7f450fe1776876d78dbb193a49afb9dfe62d4f27bf2 | 0c353a1260488c22c3ffb72de5623420c3ec35470a0b3a2045b11c29224f458e | c1ccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)nc1 | Cl-S(=O)(=O)-[Cl;H0;D1;+0:1].[#7;a:2]1:[c:3]:[c:4]:[c:5]2:[#7;a:6]:1-[C:7]-[C:8]-[CH2;D2;+0:9]-2>>[Cl;H0;D1;+0:1]-[CH;D3;+0:9]1-[C:8]-[C:7]-[#7;a:6]2:[#7;a:2]:[c:3]:[c:4]:[c:5]:2-1 | null | [] | null | null | 18 | HOUR | A solution of 1 M sulfuryl chloride in dichloromethane (20 mL, 20 mmol) is added to a solution of 7-bromo-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline (2.2 g, 5.62 mmol) in dry pyridine (50 mL). The mixture is stirred for 18 h and concentrated in vacuo. The residue is partitioned between chlor... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary halide | c1cc2n(n1)CCC2 | c1cc2n(n1)CCC2 | c1cc2n(n1)CCC2.c1ccncc1.c1ccc2ncccc2c1 | HCl | N1=CC=CC=C1 | null | 18 | Brc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1.O=S(=O)(Cl)Cl>N1=CC=CC=C1>ClC1CCn2nc(-c3ccccn3)c(-c3ccnc4cc(Br)ccc34)c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-de463c15ccd6498c993b031cb7ea560c | CN1CCCC1=O.ClC1CCn2nc(-c3ccccn3)c(-c3ccnc4cc(Br)ccc34)c21>>OC1CCn2nc(-c3ccccn3)c(-c3ccnc4cc(Br)ccc34)c21 | BrC1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC=CC=C1)CCC2Cl.CN1CCCC1=O>>BrC1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC=CC=C1)CCC2O | CN1CCCC1=[O:1].Cl[CH:2]1[CH2:3][CH2:4][n:5]2[n:6][c:7](-[c:8]3[cH:9][cH:10][cH:11][cH:12][n:13]3)[c:14](-[c:15]3[cH:16][cH:17][n:18][c:19]4[cH:20][c:21]([Br:22])[cH:23][cH:24][c:25]34)[c:26]21>>[OH:1][CH:2]1[CH2:3][CH2:4][n:5]2[n:6][c:7](-[c:8]3[cH:9][cH:10][cH:11][cH:12][n:13]3)[c:14](-[c:15]3[cH:16][cH:17][n:18][c:19... | CN1CCCC1=O.ClC1CCn2nc(-c3ccccn3)c(-c3ccnc4cc(Br)ccc34)c21 | OC1CCn2nc(-c3ccccn3)c(-c3ccnc4cc(Br)ccc34)c21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 35fbb719d864e5c183e156e60c5bcb46ec963f07bdea739345cd4fc64d532277 | c70cbb64321f74fd4df33fed2e23e8f08f37afecc5b00730d73fdfac45c186be | c1ccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)nc1 | C-N1-C-C-C-C-1=[O;H0;D1;+0:1].Cl-[CH;D3;+0:2]1-[C:3]-[C:4]-[#7;a:5]2:[#7;a:6]:[c:7]:[c:8]:[c:9]:2-1>>[OH;D1;+0:1]-[CH;D3;+0:2]1-[C:3]-[C:4]-[#7;a:5]2:[#7;a:6]:[c:7]:[c:8]:[c:9]:2-1 | null | [] | null | null | null | null | A solution of 7-bromo-4-(4-chloro-2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline (765.0 mg, 1.80 mmol) in 15% (v/v) aqueous N-methyl pyrrolidinone (15 mL) is heated at 120° C. for 18 h. The mixture is concentrated in vacuo and the residue chromatographed on SiO2 (dichloromethane to 20% methanol in ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Tertiary amide | Secondary alcohol | C1CCNC1.c1cc2n(n1)CCC2 | c1cc2n(n1)CCC2 | c1cc2n(n1)CCC2.c1ccncc1.c1ccc2ncccc2c1 | HCl | null | null | null | CN1CCCC1=O.ClC1CCn2nc(-c3ccccn3)c(-c3ccnc4cc(Br)ccc34)c21>>OC1CCn2nc(-c3ccccn3)c(-c3ccnc4cc(Br)ccc34)c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-43ca1bcbc16d469a97431b90b39c825b | OC1CCn2nc(-c3ccccn3)c(-c3ccnc4cc(Br)ccc34)c21>>O=C1CCn2nc(-c3ccccn3)c(-c3ccnc4cc(Br)ccc34)c21 | BrC1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC=CC=C1)CCC2O.CC(=O)OI1(C=2C=CC=CC2C(=O)O1)(OC(=O)C)OC(=O)C>>BrC1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC=CC=C1)CCC2=O | [OH:1][CH:2]1[CH2:3][CH2:4][n:5]2[n:6][c:7](-[c:8]3[cH:9][cH:10][cH:11][cH:12][n:13]3)[c:14](-[c:15]3[cH:16][cH:17][n:18][c:19]4[cH:20][c:21]([Br:22])[cH:23][cH:24][c:25]34)[c:26]21>>[O:1]=[C:2]1[CH2:3][CH2:4][n:5]2[n:6][c:7](-[c:8]3[cH:9][cH:10][cH:11][cH:12][n:13]3)[c:14](-[c:15]3[cH:16][cH:17][n:18][c:19]4[cH:20][c:... | OC1CCn2nc(-c3ccccn3)c(-c3ccnc4cc(Br)ccc34)c21 | O=C1CCn2nc(-c3ccccn3)c(-c3ccnc4cc(Br)ccc34)c21 | null | null | ClCCl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 1087f8281e546488b283d7c96f2b375bbca23035c3f0d9dc52dc51bb2c7ad6fc | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C1CCn2nc(-c3ccccn3)c(-c3ccnc4ccccc34)c21 | [OH;D1;+0:1]-[CH;D3;+0:2]1-[C:3]-[C:4]-[#7;a:5]2:[#7;a:6]:[c:7]:[c:8]:[c:9]:2-1>>[O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:3]-[C:4]-[#7;a:5]2:[#7;a:6]:[c:7]:[c:8]:[c:9]:2-1 | null | [] | null | null | 18 | HOUR | To a solution of 3-(7-bromo-quinolin-4-yl)-2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-4-ol (89.0 mg, 0.22 mmol) in dry dichloromethane (2 mL) is added Dess-Martin periodinane (301.0 mg, 0.71 mmol) and the resulting mixture stirred for 18 h. The reaction mixture is chromatographed on SiO2 (dichloromethane to 20... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | c1cc2n(n1)CCC2 | c1cc2n(n1)CCC2 | c1cc2n(n1)CCC2.c1ccncc1.c1ccc2ncccc2c1 | null | ClCCl | null | 18 | OC1CCn2nc(-c3ccccn3)c(-c3ccnc4cc(Br)ccc34)c21>ClCCl>O=C1CCn2nc(-c3ccccn3)c(-c3ccnc4cc(Br)ccc34)c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-284abedd07c4462bb70a539a3f546733 | CN(C)C(=S)c1cccc(Oc2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)c1>>CN(C)Cc1cccc(Oc2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)c1 | CN(C(C1=CC(=CC=C1)OC1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC=CC=C1)CCC2)=S)C.O.NN>>CN(CC1=CC(=CC=C1)OC1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC=CC=C1)CCC2)C | S=[C:4]([N:2]([CH3:1])[CH3:3])[c:5]1[cH:6][cH:7][cH:8][c:9]([O:10][c:11]2[cH:12][cH:13][c:14]3[c:15](-[c:16]4[c:17](-[c:18]5[cH:19][cH:20][cH:21][cH:22][n:23]5)[n:24][n:25]5[c:26]4[CH2:27][CH2:28][CH2:29]5)[cH:30][cH:31][n:32][c:33]3[cH:34]2)[cH:35]1>>[CH3:1][N:2]([CH3:3])[CH2:4][c:5]1[cH:6][cH:7][cH:8][c:9]([O:10][c:1... | CN(C)C(=S)c1cccc(Oc2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)c1 | CN(C)Cc1cccc(Oc2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)c1 | null | [Ni] | CO | Reduction | OtherReaction | 7ffadaacd49bd8bccc4f7d5485d95a59a9f13952085058f2a919762fe4f8a152 | 4c27c0137d8ee8336b8af3dd4769459a8c07bdef125f776867b856a8a7878e36 | c1ccc(Oc2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)cc1 | S=[C;H0;D3;+0:1](-[#7:2](-[C;D1;H3:3])-[C;D1;H3:4])-[c:5](:[c:6]):[c:7]>>[C;D1;H3:3]-[#7:2](-[C;D1;H3:4])-[CH2;D2;+0:1]-[c:5](:[c:6]):[c:7] | null | [] | null | null | 10 | MINUTE | To a refluxing mixture of Raney-nickel and hydrazine-monohydrate (0.5 mL, 10.17 mmol) in methanol (5 mL) is added N,N-dimethyl-3-[4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-yloxy]-thiobenzamide (311.0 mg, 0.63 mmol) in methanol (20 mL). The mixture is stirred 10 min and cooled to room tempe... | 10.6084/m9.figshare.5104873.v1 | null | Thioamide | null | null | null | c1ccccc1.c1ccncc1.c1cc2n(n1)CCC2.c1ccc2ncccc2c1 | Other | [Ni].CO | null | 0.166667 | CN(C)C(=S)c1cccc(Oc2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)c1>[Ni].CO>CN(C)Cc1cccc(Oc2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3b0855e547304a38aa947adbcdb4ba35 | Cc1cccc(-c2nn3c(c2-c2cc[n+]([O-])c4ccccc24)CCC3)n1.O=C(OC(=O)C(F)(F)F)C(F)(F)F>>Cc1cccc(-c2nn3c(c2-c2cc(=O)[nH]c4ccccc24)CCC3)n1 | C([O-])(O)=O.[Na+].O.CC1=CC=CC(=N1)C=1C(=C2N(N1)CCC2)C2=CC=[N+](C1=CC=CC=C21)[O-].FC(C(=O)OC(C(F)(F)F)=O)(F)F>>CC1=CC=CC(=N1)C=1C(=C2N(N1)CCC2)C2=CC(NC1=CC=CC=C21)=O | [O-][n+:16]1[cH:14][cH:13][c:12](-[c:11]2[c:7](-[c:6]3[cH:5][cH:4][cH:3][c:2]([CH3:1])[n:26]3)[n:8][n:9]3[c:10]2[CH2:23][CH2:24][CH2:25]3)[c:22]2[c:17]1[cH:18][cH:19][cH:20][cH:21]2.O=C(OC(C(F)(F)F)=[O:15])C(F)(F)F>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[n:8][n:9]3[c:10]([c:11]2-[c:12]2[cH:13][c:14](=[O:15])[nH:1... | Cc1cccc(-c2nn3c(c2-c2cc[n+]([O-])c4ccccc24)CCC3)n1.O=C(OC(=O)C(F)(F)F)C(F)(F)F | Cc1cccc(-c2nn3c(c2-c2cc(=O)[nH]c4ccccc24)CCC3)n1 | null | null | CN(C=O)C | Miscellaneous | OtherReaction | 93973839a60e6e62a1ae2c3ae647d320866bdbc4aa2dff53273b5d838c16a450 | 2be017494be94930b119f759d4ba8a7e259b4cc47fdef4d7d2ddc06577df6aaf | O=c1cc(-c2c(-c3ccccn3)nn3c2CCC3)c2ccccc2[nH]1 | F-C(-F)(-F)-C(=O)-O-C(=[O;H0;D1;+0:1])-C(-F)(-F)-F.[O-]-[n+;H0;D3:2]1:[cH;D2;+0:3]:[c:4]:[c:5]:[c:6]:[c:7]:1:[c:8]>>[O;H0;D1;+0:1]=[c;H0;D3;+0:3]1:[c:4]:[c:5]:[c:6]:[c:7](:[c:8]):[nH;D2;+0:2]:1 | null | [] | null | null | 40 | HOUR | To a solution of 4-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinoline-1-oxide (103 mg, 0.30 mmol) in N,N-dimethylformamide (3 mL) is added trifluoroacetic anhydride (425 μL, 3.0 mmol). The mixture is stirred for 40 h, poured into water, and the pH adjusted to 8 with saturated aqueous sodium... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Trifluoro group.Anhydride | null | C1=Cc2ccccc2[NH+]=C1 | c1ccc2ccccc2n1 | c1ccncc1.c1ccc2ccccc2n1.c1cc2n(n1)CCC2 | Other | CN(C=O)C | null | 40 | Cc1cccc(-c2nn3c(c2-c2cc[n+]([O-])c4ccccc24)CCC3)n1.O=C(OC(=O)C(F)(F)F)C(F)(F)F>CN(C=O)C>Cc1cccc(-c2nn3c(c2-c2cc(=O)[nH]c4ccccc24)CCC3)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cf9a8429bbc34b0c827d1a9299d8cfdd | COc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1>>Oc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | COC1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC=CC=C1)CCC2.C(C)[S-].[Na+]>>N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC(=CC=C21)O | C[O:1][c:2]1[cH:3][cH:4][c:5]2[c:6](-[c:7]3[c:8](-[c:9]4[cH:10][cH:11][cH:12][cH:13][n:14]4)[n:15][n:16]4[c:17]3[CH2:18][CH2:19][CH2:20]4)[cH:21][cH:22][n:23][c:24]2[cH:25]1>>[OH:1][c:2]1[cH:3][cH:4][c:5]2[c:6](-[c:7]3[c:8](-[c:9]4[cH:10][cH:11][cH:12][cH:13][n:14]4)[n:15][n:16]4[c:17]3[CH2:18][CH2:19][CH2:20]4)[cH:21]... | COc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | Oc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | null | null | CN(C=O)C | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)nc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | null | [] | null | null | null | null | To a solution of 7-methoxy-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline (53 mg, 0.16 mmol) in N,N-dimethylformamide (3 mL) at room temperature is added sodium ethanthiolate (133 mg, 1.6 mmol). The solution is refluxed for 4 h, cooled, and concentrated in vacuo. The residue is dissolved in meth... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccncc1.c1cc2n(n1)CCC2.c1ccc2ncccc2c1 | Other | CN(C=O)C | null | null | COc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1>CN(C=O)C>Oc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9d786f881e0d48e38a4c78c9281d797b | COc1cc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2cc1OCc1ccccc1>>COc1cc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2cc1O | C(C1=CC=CC=C1)OC1=C(C=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC=CC=C1)CCC2)OC.C1=CCC=CC1.CO>>COC=1C=C2C(=CC=NC2=CC1O)C1=C2N(N=C1C1=NC=CC=C1)CCC2 | c1ccc(C[O:27][c:26]2[c:3]([O:2][CH3:1])[cH:4][c:5]3[c:6](-[c:7]4[c:8](-[c:9]5[cH:10][cH:11][cH:12][cH:13][n:14]5)[n:15][n:16]5[c:17]4[CH2:18][CH2:19][CH2:20]5)[cH:21][cH:22][n:23][c:24]3[cH:25]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6](-[c:7]3[c:8](-[c:9]4[cH:10][cH:11][cH:12][cH:13][n:14]4)[n:15][n:16]4[c:17]3[CH2:18]... | COc1cc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2cc1OCc1ccccc1 | COc1cc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2cc1O | null | [Pd] | C(C)O | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)nc1 | [#7;a:1]:[c:2]:[c:3]:[c:4](-[O;H0;D2;+0:5]-C-c1:c:c:c:c:c:1):[c:6]>>[#7;a:1]:[c:2]:[c:3]:[c:4](-[OH;D1;+0:5]):[c:6] | null | [] | null | null | 3 | HOUR | To a mixture of 7-benzyloxy-6-methoxy-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline (17 mg, 0.04 mmol) and 10% palladium on activated carbon (3 mg) in absolute ethanol (2 mL) is added 1,4-cyclohexadiene (100 mg, 1.2 mmol). The mixture is stirred at room temperature for 3 h, treated with methano... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccncc1.c1cc2n(n1)CCC2.c1ccc2ncccc2c1 | Other | [Pd].C(C)O | null | 3 | COc1cc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2cc1OCc1ccccc1>[Pd].C(C)O>COc1cc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2cc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b826b0c50ac4412799c09914093745af | COC(=O)C=Cc1ccc2c(-c3c(-c4cccc(C)n4)nn4c3CCC4)ccnc2c1>>COC(=O)CCc1ccc2c(-c3c(-c4cccc(C)n4)nn4c3CCC4)ccnc2c1 | COC(C=CC1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC(=CC=C1)C)CCC2)=O.[H][H]>>COC(CCC1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC(=CC=C1)C)CCC2)=O | [CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH:6][c:7]1[cH:8][cH:9][c:10]2[c:11](-[c:12]3[c:13](-[c:14]4[cH:15][cH:16][cH:17][c:18]([CH3:19])[n:20]4)[n:21][n:22]4[c:23]3[CH2:24][CH2:25][CH2:26]4)[cH:27][cH:28][n:29][c:30]2[cH:31]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]2[c:11](-[c:12]3[c:13](-[c:14]4[cH:1... | COC(=O)C=Cc1ccc2c(-c3c(-c4cccc(C)n4)nn4c3CCC4)ccnc2c1 | COC(=O)CCc1ccc2c(-c3c(-c4cccc(C)n4)nn4c3CCC4)ccnc2c1 | null | [Pd] | CO | Reduction | Hydrogenation (double to single) | c04c38f95d7b746e5bdb99c368a7a33956c97b95b54c7ad89be2a85526386ec9 | 9a50abf8d2e4cd9195d7a0cadbe97483a261a81cf70b653cfddd5ecf76d383a6 | c1ccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)nc1 | [#7;a:1]:[c:2]:[c:3]:[c:4](-[CH;D2;+0:5]=[CH;D2;+0:6]-[C:7](=[O;D1;H0:8])-[#8:9]-[C;D1;H3:10]):[c:11]>>[#7;a:1]:[c:2]:[c:3]:[c:4](-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[C:7](=[O;D1;H0:8])-[#8:9]-[C;D1;H3:10]):[c:11] | null | [] | null | null | 18 | HOUR | To a solution of 3-{4-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinolin-7-yl}-acrylic acid methyl ester (0.041 g, 0.1 mmol) in methanol (1 mL) is added 10% Pd/C (0.1 g). The resulting mixture is placed under one atmosphere of hydrogen and: stirred for 18 h. The mixture is filtered and conce... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | null | null | c1ccncc1.c1cc2n(n1)CCC2.c1ccc2ncccc2c1 | null | [Pd].CO | null | 18 | COC(=O)C=Cc1ccc2c(-c3c(-c4cccc(C)n4)nn4c3CCC4)ccnc2c1>[Pd].CO>COC(=O)CCc1ccc2c(-c3c(-c4cccc(C)n4)nn4c3CCC4)ccnc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-48783e86a64147d588437490851d74d4 | CNC.COC(=O)CCc1ccc2c(-c3c(-c4cccc(C)n4)nn4c3CCC4)ccnc2c1>>Cc1cccc(-c2nn3c(c2-c2ccnc4cc(CCC(=O)N(C)C)ccc24)CCC3)n1 | C(=O)([O-])C(O)C(O)C(=O)[O-].[Na+].[K+].COC(CCC1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC(=CC=C1)C)CCC2)=O.CNC.CO.C[Al](C)C.CCCCCC>>CN(C(CCC1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC(=CC=C1)C)CCC2)=O)C | [NH:23]([CH3:24])[CH3:25].CO[C:21]([CH2:20][CH2:19][c:18]1[cH:17][c:16]2[n:15][cH:14][cH:13][c:12](-[c:11]3[c:7](-[c:6]4[cH:5][cH:4][cH:3][c:2]([CH3:1])[n:32]4)[n:8][n:9]4[c:10]3[CH2:29][CH2:30][CH2:31]4)[c:28]2[cH:27][cH:26]1)=[O:22]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[n:8][n:9]3[c:10]([c:11]2-[c:12]2[cH:13]... | CNC.COC(=O)CCc1ccc2c(-c3c(-c4cccc(C)n4)nn4c3CCC4)ccnc2c1 | Cc1cccc(-c2nn3c(c2-c2ccnc4cc(CCC(=O)N(C)C)ccc24)CCC3)n1 | null | null | ClCCl | Acylation | Aminolysis of esters | d147787750807073759132276086de98566af6772417f9288b6300bf1de7801c | fa66342dd118fe5531ba6a998ac8fab92d2b0db4fd04688560eec7d04e9be0e4 | c1ccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)nc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:6](-[C;D1;H3:5])-[C;D1;H3:7] | null | [] | 40 | CELSIUS | 18 | HOUR | To a solution of 3-{4-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinolin-7-yl}-propionic acid methyl ester (0.30 g, 0.73 mmol) and 2M dimethylamine in methanol (1.05 mL, 2.1 mmol) in dichloromethane (1 mL) is added 2 M trimethylaluminum in hexane (1.64 mL, 3.25 mmol). The solution is heated ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Tertiary amide | null | null | c1ccncc1.c1ccc2ncccc2c1.c1cc2n(n1)CCC2 | HO- | ClCCl | 40 | 18 | CNC.COC(=O)CCc1ccc2c(-c3c(-c4cccc(C)n4)nn4c3CCC4)ccnc2c1>ClCCl>Cc1cccc(-c2nn3c(c2-c2ccnc4cc(CCC(=O)N(C)C)ccc24)CCC3)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6984952448a0457eb09d4bff5fc92657 | CC(=O)OC(C)=O.NCCCOc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1>>CC(=O)NCCCOc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC(=CC=C21)OCCCN.C(C)(=O)OC(C)=O>>N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC(=CC=C21)OCCCNC(C)=O | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][CH2:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]2[c:13](-[c:14]3[c:15](-[c:16]4[cH:17][cH:18][cH:19][cH:20][n:21]4)[n:22][n:23]4[c:24]3[CH2:25][CH2:26][CH2:27]4)[cH:28][cH:29][n:30][c:31]2[cH:32]1>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]2[c:1... | CC(=O)OC(C)=O.NCCCOc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | CC(=O)NCCCOc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | null | null | N1=CC=CC=C1 | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | c1ccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)nc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[C:4]-[C:5]-[NH;D2;+0:6]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | null | [] | null | null | 2 | HOUR | To a solution of 3-[4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-yloxy]-propylamine (25 mg, 0.06 mmol) in pyridine (1 mL) at room temperature is added acetic anhydride (500 μL, 5.3 mmol). The mixture is stirred for 2 h, concentrated in vacuo, and the residue chromatographed on SiO2 (89% dichl... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccncc1.c1cc2n(n1)CCC2.c1ccc2ncccc2c1 | HO- | N1=CC=CC=C1 | null | 2 | CC(=O)OC(C)=O.NCCCOc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1>N1=CC=CC=C1>CC(=O)NCCCOc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2b378efd3f46416db23ce81612080f39 | CC(=O)OC(C)=O.OC1CCCc2c(-c3ccnc4ccccc34)c(-c3ccccn3)nn21>>CC(=O)OC1CCCc2c(-c3ccnc4ccccc34)c(-c3ccccn3)nn21 | N1=C(C=CC=C1)C1=NN2C(CCCC2O)=C1C1=CC=NC2=CC=CC=C12.C(C)(=O)OC(C)=O>>C(C)(=O)OC1CCCC=2N1N=C(C2C2=CC=NC1=CC=CC=C21)C2=NC=CC=C2 | CC(=O)O[C:2]([CH3:1])=[O:3].[OH:4][CH:5]1[CH2:6][CH2:7][CH2:8][c:9]2[c:10](-[c:11]3[cH:12][cH:13][n:14][c:15]4[cH:16][cH:17][cH:18][cH:19][c:20]34)[c:21](-[c:22]3[cH:23][cH:24][cH:25][cH:26][n:27]3)[n:28][n:29]21>>[CH3:1][C:2](=[O:3])[O:4][CH:5]1[CH2:6][CH2:7][CH2:8][c:9]2[c:10](-[c:11]3[cH:12][cH:13][n:14][c:15]4[cH:1... | CC(=O)OC(C)=O.OC1CCCc2c(-c3ccnc4ccccc34)c(-c3ccccn3)nn21 | CC(=O)OC1CCCc2c(-c3ccnc4ccccc34)c(-c3ccccn3)nn21 | null | null | N1=CC=CC=C1 | Acylation | Transesterification | a7ad17dd333d7246e42d4632a0a7042db0b0d3b7f2adb7cdb2c46498a22ac4db | c98fee24664998fb42388f3a4804f79d763c5043c4f5565ea3b46913e3a86a6e | c1ccc(-c2nn3c(c2-c2ccnc4ccccc24)CCCC3)nc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#7;a:4]:[#7;a:5](:[c:6])-[C:7](-[OH;D1;+0:8])-[C:9]>>[#7;a:4]:[#7;a:5](:[c:6])-[C:7](-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[C:9] | null | [] | null | null | null | null | A solution of 2-pyridin-2-yl-3-quinolin-4-yl-pyrazolo[1,5-a]piperidin-7-ol (0.04 g, 0.12 mmol) and acetic anhydride (0.2 mL) in pyridine (2 mL) at room temperature is stirred for 24 h. The mixture is partitioned between ethyl acetate and water. The organic portion is washed with water and brine, dried (sodium sulfate),... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Secondary alcohol | Ester | null | null | c1ccc2ncccc2c1.c1ccncc1.c1cc2n(n1)CCCC2 | HO- | N1=CC=CC=C1 | null | null | CC(=O)OC(C)=O.OC1CCCc2c(-c3ccnc4ccccc34)c(-c3ccccn3)nn21>N1=CC=CC=C1>CC(=O)OC1CCCc2c(-c3ccnc4ccccc34)c(-c3ccccn3)nn21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-83d42c16ddd347fe8030d060c09fb854 | CN(CCCOc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1)C(=O)OC(C)(C)C>>CNCCCOc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | C(C)(C)(C)OC(N(CCCOC1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC=CC=C1)CCC2)C)=O>>CNCCCOC1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC=CC=C1)CCC2 | CC(C)(C)OC(=O)[N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]2[c:11](-[c:12]3[c:13](-[c:14]4[cH:15][cH:16][cH:17][cH:18][n:19]4)[n:20][n:21]4[c:22]3[CH2:23][CH2:24][CH2:25]4)[cH:26][cH:27][n:28][c:29]2[cH:30]1>>[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]2[c:11](-[c:12]3[c:13](-[c:14... | CN(CCCOc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1)C(=O)OC(C)(C)C | CNCCCOc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | null | null | FC(C(=O)O)(F)F | Reduction | Boc amine deprotection | bbda4640db5f48af4538caded12fdadd56eacd6d4e5f7aefe46282d665df167e | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)nc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[C:4]>>[C:4]-[C:3]-[NH;D2;+0:1]-[C;D1;H3:2] | null | [] | null | null | null | null | A solution of methyl-{3-[4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-yloxy]-propyl}-carbamic acid tert-butyl ester (100 mg, 0.2 mmol) in trifluoracetic acid (3 mL) is stirred at room temperature for 6 h. The mixture is concentrated in vacuo and traces of trifluoroacetic acid removed by repea... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | null | null | c1ccncc1.c1cc2n(n1)CCC2.c1ccc2ncccc2c1 | HO- | FC(C(=O)O)(F)F | null | null | CN(CCCOc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1)C(=O)OC(C)(C)C>FC(C(=O)O)(F)F>CNCCCOc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-01768c0751dd480d88612be8046d10c7 | COC(=O)c1cccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)n1>>OCc1cccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)n1 | Cl.[BH4-].[Li+].COC(=O)C1=NC(=CC=C1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC=CC=C21.[BH4-].[Li+]>>N1=CC=C(C2=CC=CC=C12)C1=C2N(N=C1C1=CC=CC(=N1)CO)CCC2 | CO[C:2](=[O:1])[c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[n:9][n:10]3[c:11]([c:12]2-[c:13]2[cH:14][cH:15][n:16][c:17]4[cH:18][cH:19][cH:20][cH:21][c:22]24)[CH2:23][CH2:24][CH2:25]3)[n:26]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[n:9][n:10]3[c:11]([c:12]2-[c:13]2[cH:14][cH:15][n:16][c:17]4[cH:18][cH:19][cH:20][cH... | COC(=O)c1cccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)n1 | OCc1cccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)n1 | null | null | CO | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)nc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[#7;a:5]:[c:6] | 58.4 | [{"value": 58.0, "product": "N1=CC=C(C2=CC=CC=C12)C1=C2N(N=C1C1=CC=CC(=N1)CO)CCC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.4, "product": "N1=CC=C(C2=CC=CC=C12)C1=C2N(N=C1C1=CC=CC(=N1)CO)CCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 6-(3-quinolin-4-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-2-yl)pyridine-2-carboxylic acid methyl ester (0.550 g, 1.48 mmol) in methanol (20 mL) is added lithium borohydride (35.5 mg, 1.63 mmol). The mixture is stirred 1 h, additional lithium borohydride (35.5 mg, 1.63 mmol) added, and the resulting mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccncc1.c1ccc2ncccc2c1.c1cc2n(n1)CCC2 | Other | CO | null | 1 | COC(=O)c1cccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)n1>CO>OCc1cccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-571984fd63f441349f74f0f050c8655d | COc1ccc(-c2c(-c3cccc(C)n3)nn3c2CCC3)cc1>>Cc1cccc(-c2nn3c(c2-c2ccc(O)cc2)CCC3)n1 | COC1=CC=C(C=C1)C1=C2N(N=C1C1=NC(=CC=C1)C)CCC2.B(Br)(Br)Br>>CC1=CC=CC(=N1)C=1C(=C2N(N1)CCC2)C2=CC=C(C=C2)O | C[O:16][c:15]1[cH:14][cH:13][c:12](-[c:11]2[c:7](-[c:6]3[cH:5][cH:4][cH:3][c:2]([CH3:1])[n:22]3)[n:8][n:9]3[c:10]2[CH2:19][CH2:20][CH2:21]3)[cH:18][cH:17]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[n:8][n:9]3[c:10]([c:11]2-[c:12]2[cH:13][cH:14][c:15]([OH:16])[cH:17][cH:18]2)[CH2:19][CH2:20][CH2:21]3)[n:22]1 | COc1ccc(-c2c(-c3cccc(C)n3)nn3c2CCC3)cc1 | Cc1cccc(-c2nn3c(c2-c2ccc(O)cc2)CCC3)n1 | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(-c2c(-c3ccccn3)nn3c2CCC3)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 5.8 | [{"value": 5.8, "product": "CC1=CC=CC(=N1)C=1C(=C2N(N1)CCC2)C2=CC=C(C=C2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 5.7, "product": "CC1=CC=CC(=N1)C=1C(=C2N(N1)CCC2)C2=CC=C(C=C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of 3-(4-methoxy-phenyl)-2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole (72 mg, 0.24 mmol) in methylene chloride (1 mL) is added boron tribromide (0.3 mL). The solution is stirred at ambient temperature for 3 h, then quenched with methanol. The mixture is concentrated in vacuo to a reddish... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccncc1.c1ccccc1.c1cc2n(n1)CCC2 | Other | C(Cl)Cl | null | 3 | COc1ccc(-c2c(-c3cccc(C)n3)nn3c2CCC3)cc1>C(Cl)Cl>Cc1cccc(-c2nn3c(c2-c2ccc(O)cc2)CCC3)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4c71d311966240d38a6e88fb07d5d068 | O=C(OCc1ccccc1)N1CCC(COc2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)C1>>CN1CCC(COc2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)C1 | [H-].[Al+3].[Li+].[H-].[H-].[H-].C(C1=CC=CC=C1)OC(=O)N1CC(CC1)COC1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC=CC=C1)CCC2>>CN1CC(CC1)COC1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC=CC=C1)CCC2 | O=[C:1](OCc1ccccc1)[N:2]1[CH2:3][CH2:4][CH:5]([CH2:6][O:7][c:8]2[cH:9][cH:10][c:11]3[c:12](-[c:13]4[c:14](-[c:15]5[cH:16][cH:17][cH:18][cH:19][n:20]5)[n:21][n:22]5[c:23]4[CH2:24][CH2:25][CH2:26]5)[cH:27][cH:28][n:29][c:30]3[cH:31]2)[CH2:32]1>>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([CH2:6][O:7][c:8]2[cH:9][cH:10][c:11]3[c:12... | O=C(OCc1ccccc1)N1CCC(COc2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)C1 | CN1CCC(COc2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)C1 | null | null | O1CCCC1.C(=O)([O-])C(O)C(O)C(=O)[O-].[K+].[Na+] | Reduction | OtherReaction | 81a372870d2403dcf41248d469703f52017dd1a2651b7f00ce4f90bb1a325b1a | f6bec327410058c9cba187636b48ed5ef90429f24bf839d7fb4e0588ab9ff83e | c1ccc(-c2nn3c(c2-c2ccnc4cc(OCC5CCNC5)ccc24)CCC3)nc1 | O=[C;H0;D3;+0:1](-O-C-c1:c:c:c:c:c:1)-[#7:2](-[C:3])-[C:4]>>[C:3]-[#7:2](-[CH3;D1;+0:1])-[C:4] | null | [] | 65 | CELSIUS | null | null | To a 1 M solution of lithium aluminum hydride in tetrahydrofuran (0.60 mL, 0.59 mmol) is added a solution of 3-[4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-yloxymethyl]-pyrrolidine-1-carboxylic acid benzyl ester (215 mg, 0.39 mmol) in tetrahydrofuran (2 mL). The mixture is heated at 65° C. f... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | null | c1ccccc1 | null | C1CC[NH]C1.c1ccncc1.c1cc2n(n1)CCC2.c1ccc2ncccc2c1 | HO- | O1CCCC1.C(=O)([O-])C(O)C(O)C(=O)[O-].[K+].[Na+] | 65 | null | O=C(OCc1ccccc1)N1CCC(COc2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)C1>O1CCCC1.C(=O)([O-])C(O)C(O)C(=O)[O-].[K+].[Na+]>CN1CCC(COc2ccc3c(-c4c(-c5ccccn5)nn5c4CCC5)ccnc3c2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-299b9a551a6048d98adae389038ab081 | C=O.Cc1cccc(-c2nn3c(c2-c2ccnc4cc(C(=O)NC(C)(C)CN)ccc24)CCC3)n1>>Cc1cccc(-c2nn3c(c2-c2ccnc4cc(C(=O)NC(C)(C)CN(C)C)ccc24)CCC3)n1 | NCC(C)(C)NC(=O)C1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC(=CC=C1)C)CCC2.C(#N)[BH3-].[Na+].C(C)(=O)O.C=O>>CN(CC(C)(C)NC(=O)C1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC(=CC=C1)C)CCC2)C | O=[CH2:27].[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[n:8][n:9]3[c:10]([c:11]2-[c:12]2[cH:13][cH:14][n:15][c:16]4[cH:17][c:18]([C:19](=[O:20])[NH:21][C:22]([CH3:23])([CH3:24])[CH2:25][NH2:26])[cH:29][cH:30][c:31]24)[CH2:32][CH2:33][CH2:34]3)[n:35]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[n:8][n:9]3[c:10]([c:11]... | C=O.Cc1cccc(-c2nn3c(c2-c2ccnc4cc(C(=O)NC(C)(C)CN)ccc24)CCC3)n1 | Cc1cccc(-c2nn3c(c2-c2ccnc4cc(C(=O)NC(C)(C)CN(C)C)ccc24)CCC3)n1 | null | null | CO | Heteroatom Alkylation and Arylation | Eschweiler-Clarke Primary Amine Methylation | 5bc40be4d4b4346801fbfcec480fec37de3ff2eecebe2990b3686fa4792d12b6 | 5cdbf447f632627824e84e0bcac2293ea9ebd70c19b0d56dea90691653b444c7 | c1ccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)nc1 | O=[CH2;D1;+0:1].[C:2]-[C:3]-[NH2;D1;+0:4]>>[C:2]-[C:3]-[N;H0;D3;+0:4](-[C;D1;H3:5])-[CH3;D1;+0:1] | null | [] | 0 | CELSIUS | 10 | MINUTE | A mixture of 4-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinoline-7-carboxylic acid(2-amino-1,1-dimethyl-ethyl)-amide (0.12 g, 0.27 mmol), sodium cyanoborohydride (0.038 g, 0.6 mmol), and acetic acid (0.077 mL, 1.3 mmol) in methanol (5 mL) is cooled to 0° C. and stirred for 10 min. A soluti... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Primary amine | Tertiary amine | null | null | c1ccncc1.c1ccc2ncccc2c1.c1cc2n(n1)CCC2 | null | CO | 0 | 0.166667 | C=O.Cc1cccc(-c2nn3c(c2-c2ccnc4cc(C(=O)NC(C)(C)CN)ccc24)CCC3)n1>CO>Cc1cccc(-c2nn3c(c2-c2ccnc4cc(C(=O)NC(C)(C)CN(C)C)ccc24)CCC3)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d2b49fdbf8f8460680519fe9c34d4e15 | Cc1cccc(-c2nn3c(c2-c2ccc(F)cc2)CC[C@H]3COCc2ccccc2)n1>>Cc1cccc(-c2nn3c(c2-c2ccc(F)cc2)CC[C@H]3CO)n1 | C(C1=CC=CC=C1)OC[C@@H]1CCC=2N1N=C(C2C2=CC=C(C=C2)F)C2=NC(=CC=C2)C.C[Si](C)(C)I>>FC1=CC=C(C=C1)C1=C2N(N=C1C1=NC(=CC=C1)C)[C@@H](CC2)CO | c1ccc(C[O:23][CH2:22][C@H:21]2[n:9]3[n:8][c:7](-[c:6]4[cH:5][cH:4][cH:3][c:2]([CH3:1])[n:24]4)[c:11](-[c:12]4[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]4)[c:10]3[CH2:19][CH2:20]2)cc1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[n:8][n:9]3[c:10]([c:11]2-[c:12]2[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]2)[CH2:19][CH2:20]... | Cc1cccc(-c2nn3c(c2-c2ccc(F)cc2)CC[C@H]3COCc2ccccc2)n1 | Cc1cccc(-c2nn3c(c2-c2ccc(F)cc2)CC[C@H]3CO)n1 | null | null | CO.C(Cl)(Cl)Cl | Deprotection | Hydroxyl benzyl deprotection | c8a6fd2e05b2d36256c76b73aaf4118f20eb14abce1c0289b554265e30b218aa | 29a81fd08d26edc3da6d72c4958026f5af2119326dc1b4714ee5be1c41835609 | c1ccc(-c2c(-c3ccccn3)nn3c2CCC3)cc1 | [#7;a:1]-[C:2]-[C:3]-[O;H0;D2;+0:4]-C-c1:c:c:c:c:c:1>>[#7;a:1]-[C:2]-[C:3]-[OH;D1;+0:4] | null | [] | null | null | 2 | HOUR | To a solution of (S)-6-benzyloxymethyl-3-(4-fluoro-phenyl)-2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole (0.3 g, 0.73 mmol) in chloroform (1.0 mL) is added trimethylsilyl iodide (0.173 mL, 1.21 mmol). The mixture is stirred 2 h, diluted with methanol (10 mL), stirred 10 min, and concentrated in vacuo.... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Primary alcohol | c1ccccc1 | null | c1ccncc1.c1ccccc1.c1cc2n(n1)CCC2 | Other | CO.C(Cl)(Cl)Cl | null | 2 | Cc1cccc(-c2nn3c(c2-c2ccc(F)cc2)CC[C@H]3COCc2ccccc2)n1>CO.C(Cl)(Cl)Cl>Cc1cccc(-c2nn3c(c2-c2ccc(F)cc2)CC[C@H]3CO)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5b953fa7674c4f19b380bf9e67c072b5 | Cc1cccc(-c2nn3c(c2-c2ccc(F)cc2)CC[C@H]3COS(C)(=O)=O)n1.[C-]#N>>Cc1cccc(-c2nn3c(c2-c2ccc(F)cc2)CC[C@H]3CC#N)n1 | [C-]#N.[K+].FC1=CC=C(C=C1)C1=C2N(N=C1C1=NC(=CC=C1)C)[C@@H](CC2)COS(=O)(=O)C>>FC1=CC=C(C=C1)C1=C2N(N=C1C1=NC(=CC=C1)C)[C@@H](CC2)CC#N | CS(=O)(=O)O[CH2:22][C@H:21]1[n:9]2[n:8][c:7](-[c:6]3[cH:5][cH:4][cH:3][c:2]([CH3:1])[n:25]3)[c:11](-[c:12]3[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]3)[c:10]2[CH2:19][CH2:20]1.[C-:23]#[N:24]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[n:8][n:9]3[c:10]([c:11]2-[c:12]2[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]2)[CH2:19... | Cc1cccc(-c2nn3c(c2-c2ccc(F)cc2)CC[C@H]3COS(C)(=O)=O)n1.[C-]#N | Cc1cccc(-c2nn3c(c2-c2ccc(F)cc2)CC[C@H]3CC#N)n1 | null | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC | O.CN(C=O)C.C(C)(=O)OCC | C-C Coupling | OtherReaction | 18f4bbb9c586d5002707644e5539611116bc9c01fc56c5a56ec0d1b0251f5f0b | 89d1e6e004e8ba10561e22cfb8893e96c375691951aae8f42243dfb0e0a04eec | c1ccc(-c2c(-c3ccccn3)nn3c2CCC3)cc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[C:3])-[#7;a:4](:[#7;a:5]):[c:6].[C-;H0;D1:7]#[N;D1;H0:8]>>[#7;a:5]:[#7;a:4](:[c:6])-[C:2](-[CH2;D2;+0:1]-[C;H0;D2;+0:7]#[N;D1;H0:8])-[C:3] | null | [] | 70 | CELSIUS | null | null | A mixture of potassium cyanide (44 mg, 0.67 mmol), tetrabutylammonium iodide (catalytic), and (S)-methanesulfonic acid 3-(4-fluoro-phenyl)-2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-6-ylmethyl ester (54 mg, 0.135 mmol) in N,N-dimethylformamide (0.35 mL) and water (0.13 mL) is heated at 70° C. for 4 ... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate | Nitrile | null | null | c1ccncc1.c1ccccc1.c1cc2n(n1)CCC2 | MsOH.HO- | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC.O.CN(C=O)C.C(C)(=O)OCC | 70 | null | Cc1cccc(-c2nn3c(c2-c2ccc(F)cc2)CC[C@H]3COS(C)(=O)=O)n1.[C-]#N>[I-].C(CCC)[N+](CCCC)(CCCC)CCCC.O.CN(C=O)C.C(C)(=O)OCC>Cc1cccc(-c2nn3c(c2-c2ccc(F)cc2)CC[C@H]3CC#N)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4764fcefb6504a36872261252b2115e7 | Oc1[nH]nc(-c2ccccn2)c1-c1ccnc2ccccc12>>c1ccc(-c2nn3c(c2-c2ccnc4ccccc24)OCC3)nc1 | N1=C(C=CC=C1)C=1C(=C(NN1)O)C1=CC=NC2=CC=CC=C12.C(CO)O.C(CCC)P(CCCC)CCCC.N(=NC(=O)N1CCCCC1)C(=O)N1CCCCC1>>N1=C(C=CC=C1)C1=NN2C(OCC2)=C1C1=CC=NC2=CC=CC=C12 | [cH:1]1[cH:2][cH:3][c:4](-[c:5]2[n:6][nH:7][c:8]([OH:20])[c:9]2-[c:10]2[cH:11][cH:12][n:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]23)[n:23][cH:24]1>>[cH:1]1[cH:2][cH:3][c:4](-[c:5]2[n:6][n:7]3[c:8]([c:9]2-[c:10]2[cH:11][cH:12][n:13][c:14]4[cH:15][cH:16][cH:17][cH:18][c:19]24)[O:20][CH2:21][CH2:22]3)[n:23][cH:24]1 | Oc1[nH]nc(-c2ccccn2)c1-c1ccnc2ccccc12 | c1ccc(-c2nn3c(c2-c2ccnc4ccccc24)OCC3)nc1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 00a5b371a667ab86966ad0d0ef805855ad61b9adb7934d1aba65fcb1bb2e0df2 | 0f0966e3597a58033417ecee71659f4d0c082f95d46b1e52c95541e6e4a59086 | c1ccc(-c2nn3c(c2-c2ccnc4ccccc24)OCC3)nc1 | [OH;D1;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[nH;D2;+0:6]:1>>[#7;a:5]1:[c:4]:[c:3]:[c:2]2:[n;H0;D3;+0:6]:1-[C:7]-[C:8]-[O;H0;D2;+0:1]-2 | 74.9 | [{"value": 46.0, "product": "N1=C(C=CC=C1)C1=NN2C(OCC2)=C1C1=CC=NC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.9, "product": "N1=C(C=CC=C1)C1=NN2C(OCC2)=C1C1=CC=NC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5-pyridin-2-yl-4-quinolin-4-yl 2H-pyrazol-3-ol (50 mg, 0.17 mmol), ethylene glycol (15 mg, 0.24 mmol) and tri-n-butylphosphine (100 mg, 0.50 mmol) in tetrahydrofuran (15 mL) is added 1,1′-(azodicarbonyl)dipiperidine (120 mg, 0.48 mmol). The solution is heated at reflux for 5 h, cooled, and filtered thr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether | c1cn[nH]c1 | c1cc2n(n1)CCO2 | c1ccncc1.c1ccc2ncccc2c1.c1cc2n(n1)CCO2 | Other | O1CCCC1 | null | null | Oc1[nH]nc(-c2ccccn2)c1-c1ccnc2ccccc12>O1CCCC1>c1ccc(-c2nn3c(c2-c2ccnc4ccccc24)OCC3)nc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7f5b3d00643846858bae9967fed2be37 | O=C(Nc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1)OCCO>>O=C1OCCN1c1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | OCCOC(NC1=CC=C2C(=CC=NC2=C1)C1=C2N(N=C1C1=NC=CC=C1)CCC2)=O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)C>>N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC(=CC=C21)N2C(OCC2)=O | O[CH2:5][CH2:4][O:3][C:2](=[O:1])[NH:6][c:7]1[cH:8][cH:9][c:10]2[c:11](-[c:12]3[c:13](-[c:14]4[cH:15][cH:16][cH:17][cH:18][n:19]4)[n:20][n:21]4[c:22]3[CH2:23][CH2:24][CH2:25]4)[cH:26][cH:27][n:28][c:29]2[cH:30]1>>[O:1]=[C:2]1[O:3][CH2:4][CH2:5][N:6]1[c:7]1[cH:8][cH:9][c:10]2[c:11](-[c:12]3[c:13](-[c:14]4[cH:15][cH:16][... | O=C(Nc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1)OCCO | O=C1OCCN1c1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 33411090b6c5d9a042cd27a65bc509173ae6acdca87f4834848abb86642d42b6 | 37df4f62d621c5df4eacc80f72b83ef887737caa083adb04ff0c8b3a28bbaeec | O=C1OCCN1c1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | O-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]:[c:10]:[#7;a:11]>>[#7;a:11]:[c:10]:[c:9]:[c:7](-[N;H0;D3;+0:6]1-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4]-1=[O;D1;H0:5]):[c:8] | null | [] | null | null | 18 | HOUR | To a solution of [4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-yl]-carbamic acid 2-hydroxy-ethyl ester (40.2 mg, 0.097 mmol) and triphenylphosphine (35.0 mg, 0.14 mmol) in tetrahydrofuran (1 mL) at room temperature is added diethyl 40% azodicarboxylate in toluene (50 μL, 0.11 mmol). The mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Primary alcohol | Carbamic ester | null | C1COC[NH]1 | C1COC[NH]1.c1ccncc1.c1cc2n(n1)CCC2.c1ccc2ncccc2c1 | HO- | O1CCCC1 | null | 18 | O=C(Nc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1)OCCO>O1CCCC1>O=C1OCCN1c1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3083cd80a9114d2db6dad12c4718d638 | OCc1ccncc1.Oc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1>>c1ccc(-c2nn3c(c2-c2ccnc4cc(OCc5ccncc5)ccc24)CCC3)nc1 | CC(C)OC(=O)/N=N/C(=O)OC(C)C.N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC(=CC=C21)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.N1=CC=C(C=C1)CO>>N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC(=CC=C21)OCC2=CC=NC=C2 | O[CH2:18][c:19]1[cH:20][cH:21][n:22][cH:23][cH:24]1.[cH:1]1[cH:2][cH:3][c:4](-[c:5]2[n:6][n:7]3[c:8]([c:9]2-[c:10]2[cH:11][cH:12][n:13][c:14]4[cH:15][c:16]([OH:17])[cH:25][cH:26][c:27]24)[CH2:28][CH2:29][CH2:30]3)[n:31][cH:32]1>>[cH:1]1[cH:2][cH:3][c:4](-[c:5]2[n:6][n:7]3[c:8]([c:9]2-[c:10]2[cH:11][cH:12][n:13][c:14]4[... | OCc1ccncc1.Oc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1 | c1ccc(-c2nn3c(c2-c2ccnc4cc(OCc5ccncc5)ccc24)CCC3)nc1 | null | null | O1CCCC1.C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc(-c2nn3c(c2-c2ccnc4cc(OCc5ccncc5)ccc24)CCC3)nc1 | O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1.[#7;a:8]:[c:9]:[c:10]:[c:11](-[OH;D1;+0:12]):[c:13]>>[#7;a:8]:[c:9]:[c:10]:[c:11](-[O;H0;D2;+0:12]-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1):[c:13] | null | [] | 75 | CELSIUS | null | null | 4-(2-Pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-ol (0.100 g, 0.305 mmol), triphenylphosphine (0.080 g, 0.305 mmol), and 4-pyridylcarbinol (0.033 g, 0.305 mmol) are combined in toluene (1.0 mL) and treated with diisopropylazodicarboxylate (0.062 g, 0.305 mmol). The resulting mixture is heated at ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccncc1.c1ccc2ncccc2c1.c1ccncc1.c1cc2n(n1)CCC2 | HO- | O1CCCC1.C1(=CC=CC=C1)C | 75 | null | OCc1ccncc1.Oc1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc2c1>O1CCCC1.C1(=CC=CC=C1)C>c1ccc(-c2nn3c(c2-c2ccnc4cc(OCc5ccncc5)ccc24)CCC3)nc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b77d1639029d4675ac57aa188f0309f6 | CCCC[C]([Sn])=C(CCCC)CCCC.Clc1cccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)n1>>C=Cc1cccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)n1 | C(CCC)C(=C(CCCC)CCCC)[Sn].ClC1=CC=CC(=N1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC=CC=C21>>C(=C)C1=CC=CC(=N1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC=CC=C21 | CCCC[C]([Sn])=[C:2](CCCC)[CH2:1]CCC.Cl[c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[n:9][n:10]3[c:11]([c:12]2-[c:13]2[cH:14][cH:15][n:16][c:17]4[cH:18][cH:19][cH:20][cH:21][c:22]24)[CH2:23][CH2:24][CH2:25]3)[n:26]1>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[n:9][n:10]3[c:11]([c:12]2-[c:13]2[cH:14][cH:15][n:16][c:17]4... | CCCC[C]([Sn])=C(CCCC)CCCC.Clc1cccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)n1 | C=Cc1cccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)n1 | null | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | cca5ad0b869f6644971e5c42ef93f1875be746905f6236eef9eebc2858794972 | 27ac22ec7469bd7f39cc3c50746346e388051103704091d8380f391d425a4ebf | c1ccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)nc1 | C-C-C-C-[C;H0;D3;+0:1](-[CH2;D2;+0:2]-C-C-C)=[C](-[Sn])-C-C-C-C.Cl-[c;H0;D3;+0:3](:[#7;a:4]:[c:5]):[c:6]:[c:7]>>[CH2;D1;+0:2]=[CH;D2;+0:1]-[c;H0;D3;+0:3](:[#7;a:4]:[c:5]):[c:6]:[c:7] | 62 | [{"value": 62.0, "product": "C(=C)C1=CC=CC(=N1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC=CC=C21", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | Add tributylvinyltin (0.059 mL, 0.19 mmol) to a solution of 4-[2-(6-chloro-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinoline, EXAMPLE 101, (59 mg, 0.17 mmol) in toluene (0.7 mL) at RT. Bubble nitrogen into the reaction mixture for 5 min and add tetrakis-(triphenylphosphine) palladium (0) (10 mg, 0.0085... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Vinyl | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccc2ncccc2c1.c1cc2n(n1)CCC2 | HCl.Sn | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)C | null | 0.083333 | CCCC[C]([Sn])=C(CCCC)CCCC.Clc1cccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)n1>[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)C>C=Cc1cccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ea1e8d4f720a4896a3c22d426cba3c83 | COC(=O)C=Cc1ccc2nccc(-c3c(-c4cccc(C)n4)nn4c3CCC4)c2c1.[OH-]>>CO.Cc1cccc(-c2nn3c(c2-c2ccnc4ccc(C=CC(=O)O)cc24)CCC3)n1.N | COC(C=CC=1C=C2C(=CC=NC2=CC1)C1=C2N(N=C1C1=NC(=CC=C1)C)CCC2)=O.[OH-].[Li+]>>N.CO.CC1=CC=CC(=N1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC=C(C=C21)C=CC(=O)O | [CH3:1][O:2][C:24]([CH:23]=[CH:22][c:21]1[cH:20][cH:19][c:18]2[n:17][cH:16][cH:15][c:14](-[c:13]3[c:9](-[c:8]4[cH:7][cH:6][cH:5][c:4]([CH3:3])[n:32]4)[n:10][n:11]4[c:12]3[CH2:29][CH2:30][CH2:31]4)[c:28]2[cH:27]1)=[O:25].[OH-:26]>>[CH3:1][OH:2].[CH3:3][c:4]1[cH:5][cH:6][cH:7][c:8](-[c:9]2[n:10][n:11]3[c:12]([c:13]2-[c:1... | COC(=O)C=Cc1ccc2nccc(-c3c(-c4cccc(C)n4)nn4c3CCC4)c2c1.[OH-] | CO.Cc1cccc(-c2nn3c(c2-c2ccnc4ccc(C=CC(=O)O)cc24)CCC3)n1.N | null | null | CO.O | Acylation | OtherReaction | db9ee1d9bb846253c10c2f639d42c12d092d033c3651a71ea16dc0ecf4a55bdc | c5cee7247c9bd9461d9349ac8515839185f2e1daff3eef7b9c67c8b1310a1abe | c1ccc(-c2nn3c(c2-c2ccnc4ccccc24)CCC3)nc1 | [C;D1;H3:1]-[O;H0;D2;+0:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C:5]=[C:6]-[c:7].[OH-;D0:8]>>[C;D1;H3:1]-[OH;D1;+0:2].[O;D1;H0:4]=[C;H0;D3;+0:3](-[OH;D1;+0:8])-[C:5]=[C:6]-[c:7] | 181.6 | [{"value": 92.0, "product": "CC1=CC=CC(=N1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC=C(C=C21)C=CC(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 181.6, "product": "CC1=CC=CC(=N1)C=1C(=C2N(N1)CCC2)C2=CC=NC1=CC=C(C=C21)C=CC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Dissolve 3-{4-[2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinolin-6-yl}-acrylic acid methyl ester (0.040 g, 0.1 mmol) in methanol/water (3:1, 2 mL). Add lithium hydroxide (0.010 g, 0.25 mmol) and stir the mixture 18 h. Remove the solvent then load the residue on a SCX resin column with methan... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid.Methanol | null | null | c1ccncc1.c1ccc2ncccc2c1.c1cc2n(n1)CCC2 | null | CO.O | null | null | COC(=O)C=Cc1ccc2nccc(-c3c(-c4cccc(C)n4)nn4c3CCC4)c2c1.[OH-]>CO.O>CO.Cc1cccc(-c2nn3c(c2-c2ccnc4ccc(C=CC(=O)O)cc24)CCC3)n1.N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9c4c3610f2df4ee7bbd50d06f17076ad | CC1(CO)COC1.Cc1ccc(S(=O)(=O)Cl)cc1>>Cc1ccc(S(=O)(=O)CC2(C)COC2)cc1 | [OH-].[Na+].CC1(COC1)CO.C1(=CC=C(C=C1)S(=O)(=O)Cl)C.O>>CC1(COC1)CS(=O)(=O)C1=CC=C(C)C=C1 | O[CH2:9][C:10]1([CH3:11])[CH2:12][O:13][CH2:14]1.Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:16][cH:15]1)(=[O:7])=[O:8]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[CH2:9][C:10]2([CH3:11])[CH2:12][O:13][CH2:14]2)[cH:15][cH:16]1 | CC1(CO)COC1.Cc1ccc(S(=O)(=O)Cl)cc1 | Cc1ccc(S(=O)(=O)CC2(C)COC2)cc1 | null | null | C(Cl)Cl | Acylation | OtherReaction | d05d91207659f8fa672c205a316a670adfe2b92492fc9adad2ee3f241e574fb9 | a7748b0f3b0eba3868d0cf03ae67721db046202accaaea9cadb4edbc96ec8768 | O=S(=O)(CC1COC1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].O-[CH2;D2;+0:7]-[C:8]1(-[C;D1;H3:9])-[C:10]-[#8:11]-[C:12]-1>>[C;D1;H3:9]-[C:8]1(-[CH2;D2;+0:7]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6])-[C:10]-[#8:11]-[C:12]-1 | null | [] | 0 | CELSIUS | null | null | 3-methyl-3-oxetanemethanol (100 g, 0.98 mol) was dissolved in 250 mL methylene chloride, and a 35% solution of sodium hydroxide (143.60 g, 1.08 mol)was added, and the reaction was cooled to 0° C. A solution of p-toluenesulfonyl chloride was added (186.67 g, 0.98 mol) in 375 mL methylene chloride was added over 1 hour. ... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Primary alcohol.Sulfonyl halide | Tosylate | null | null | c1ccccc1.C1COC1 | HCl | C(Cl)Cl | 0 | null | CC1(CO)COC1.Cc1ccc(S(=O)(=O)Cl)cc1>C(Cl)Cl>Cc1ccc(S(=O)(=O)CC2(C)COC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a03c043bf9b440c881d3b009ffa8e67b | CC(C)(C)NC(=O)CC#N.O=NCl>>CC(C)(C)NC(=O)C(C#N)=NO | C(#N)CC(=O)NC(C)(C)C.N(=O)Cl.C(Cl)Cl>>C(#N)C(C(=O)NC(C)(C)C)=NO | [CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][C:6](=[O:7])[CH2:8][C:9]#[N:10].Cl[N:11]=[O:12]>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][C:6](=[O:7])[C:8]([C:9]#[N:10])=[N:11][OH:12] | CC(C)(C)NC(=O)CC#N.O=NCl | CC(C)(C)NC(=O)C(C#N)=NO | null | null | C(Cl)(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 14e61edf5e1d02c9cc5248a23871f34687459b806b72cc2881a9dcf92540361b | 66ef1e070934358873529ac787e21a7907bee71eca7d7ccd0386ced07b5054b6 | null | Cl-[N;H0;D2;+0:1]=[O;H0;D1;+0:2].[C:3]-[#7:4]-[C:5](=[O;D1;H0:6])-[CH2;D2;+0:7]-[C:8]#[N;D1;H0:9]>>[C:3]-[#7:4]-[C:5](=[O;D1;H0:6])-[C;H0;D3;+0:7](-[C:8]#[N;D1;H0:9])=[N;H0;D2;+0:1]-[OH;D1;+0:2] | null | [] | null | null | null | null | The compound of the formula 5 can be prepared also by the following novel method: 2-Cyano-N-(1,1-dimethylethyl)acetamide 11 (Bhawal, B. M.; Khanapure, S. P.; Biehl, E. R.; Syn. Commun., 1990, 20, 3235) is allowed to react with nitrosyl chloride in an inert organic solvent such as CH2Cl2 or CHCl3 at moderate temperature... | 10.6084/m9.figshare.5104873.v1 | null | Nitroso | Oxime | null | null | null | HCl | C(Cl)(Cl)Cl | null | null | CC(C)(C)NC(=O)CC#N.O=NCl>C(Cl)(Cl)Cl>CC(C)(C)NC(=O)C(C#N)=NO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-430da2d36fa44eec9014d4707e973baa | CC(C)(C)NC(=O)C(C#N)N=C(c1ccccc1)c1ccccc1>>CC(C)(C)NC(=O)C(N)C#N | C(#N)C(C(=O)NC(C)(C)C)N=C(C1=CC=CC=C1)C1=CC=CC=C1.C(C)(=O)OCC.Cl>>Cl.NC(C(=O)NC(C)(C)C)C#N | c1ccc(C(c2ccccc2)=[N:9][CH:8]([C:6]([NH:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[C:10]#[N:11])cc1>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][C:6](=[O:7])[CH:8]([NH2:9])[C:10]#[N:11] | CC(C)(C)NC(=O)C(C#N)N=C(c1ccccc1)c1ccccc1 | CC(C)(C)NC(=O)C(N)C#N | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | fe28e0513c54643a2e998df32fe9ad14c978580c0e1fa51268908e5a62d5d818 | 69d38cb38c5a54a23121b1c97287244fbbd5b6f97c6a1faf8cb1a05e149dd1cc | null | [C:1]-[#7:2]-[C:3](=[O;D1;H0:4])-[C:5](-[C:6]#[N;D1;H0:7])-[N;H0;D2;+0:8]=C(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:1]-[#7:2]-[C:3](=[O;D1;H0:4])-[C:5](-[NH2;D1;+0:8])-[C:6]#[N;D1;H0:7] | null | [] | 60 | CELSIUS | null | null | 2-Cyano-N-(1,1-dimethylethyl)-2-[(diphenylmethylene)amino]acetamide 4 (900 g. 2.818 mol), ethyl acetate (4.5 L) and aqueous HCl (1 N. 4.5 L) were placed into a 12 L three-necked flask equipped with a nitrogen inlet, a gas outlet tube, reflux condenser, thermometer, mechanical stirrer, and maintained under a positive pr... | 10.6084/m9.figshare.5104873.v1 | null | Substituted imine | Primary amine | c1ccccc1.c1ccccc1 | null | null | Other | C(Cl)Cl | 60 | null | CC(C)(C)NC(=O)C(C#N)N=C(c1ccccc1)c1ccccc1>C(Cl)Cl>CC(C)(C)NC(=O)C(N)C#N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0462536148484ddba9052e5d961cae80 | CN1Cn2cnc(C(=O)NC(C)(C)C)c2N=N1.O=S(=O)(O)O>>Cn1nnc2c(C(N)=O)ncn2c1=O | CC(C)(C)NC(=O)C=1N=CN2C1N=NN(C2)C.OS(=O)(=O)O>>CN1N=NC=2N(C1=O)C=NC2C(=O)N | CC(C)(C)[NH:8][C:7]([c:6]1[c:5]2[n:12]([cH:11][n:10]1)[CH2:13][N:2]([CH3:1])[N:3]=[N:4]2)=[O:9].O=S(=O)(O)[OH:14]>>[CH3:1][n:2]1[n:3][n:4][c:5]2[c:6]([C:7]([NH2:8])=[O:9])[n:10][cH:11][n:12]2[c:13]1=[O:14] | CN1Cn2cnc(C(=O)NC(C)(C)C)c2N=N1.O=S(=O)(O)O | Cn1nnc2c(C(N)=O)ncn2c1=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 82dd647d89c7a5c52830fe2ab2a4bd6ba4bfe9f8ee8ecde1b178802b85f646f7 | 9811ee4b5eaea09b111ffcd6e6c30ff3136dc87ff2a8a8400d245c8d7e3f7947 | O=c1[nH]nnc2cncn12 | C-C(-C)(-C)-[NH;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[#7;a:5]:[c:6]:[#7;a:7]2:[c:8]:1-[N;H0;D2;+0:9]=[N;H0;D2;+0:10]-[N;H0;D3;+0:11](-[C;D1;H3:12])-[CH2;D2;+0:13]-2.O-S(=O)(=O)-[OH;D1;+0:14]>>[C;D1;H3:12]-[n;H0;D3;+0:11]1:[n;H0;D2;+0:10]:[n;H0;D2;+0:9]:[c:8]2:[#7;a:7](:[c:6]:[#7;a:5]:[c:4]:2-[C:2](-[NH2;D1;+0:1])=[O;D1;... | null | [] | null | null | 2 | HOUR | t-Butyl-Temozolomide 8 (4.01 g, 16.023 mmol) and conc. H2SO4 (8 mL) (Fisher Scientific) were placed into a 50 mL flask equipped with a stirrer bar. The mixture was stirred for 2 hours at room temperature and then slowly poured into ice-cold EtOH (160 mL). A white precipitate formed, which was collected by vacuum filtra... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Secondary amide | Primary amide | c1ncn2c1N=N[NH]C2 | c1ncn2cnnnc12 | c1ncn2cnnnc12 | HO- | null | null | 2 | CN1Cn2cnc(C(=O)NC(C)(C)C)c2N=N1.O=S(=O)(O)O>>Cn1nnc2c(C(N)=O)ncn2c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-70bb7f483dcf4ecdbd2fd522debbf3d6 | CNC(=O)n1cnc(C(N)=O)c1N>>NC(=O)c1nc[nH]c1N | NC1=C(N=CN1C(=O)NC)C(=O)N.CCN(CC)CC>>NC1=C(N=CN1)C(=O)N | CNC(=O)[n:7]1[cH:6][n:5][c:4]([C:2]([NH2:1])=[O:3])[c:8]1[NH2:9]>>[NH2:1][C:2](=[O:3])[c:4]1[n:5][cH:6][nH:7][c:8]1[NH2:9] | CNC(=O)n1cnc(C(N)=O)c1N | NC(=O)c1nc[nH]c1N | null | null | CO | Reduction | OtherReaction | 2c44d504f691c334b40a8b352d4e26b28d8f1ee1705bd02bf2f02cf4fe90a134 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1c[nH]cn1 | C-N-C(=O)-[n;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4](-[C:5](-[N;D1;H2:6])=[O;D1;H0:7]):[c:8]:1-[N;D1;H2:9]>>[N;D1;H2:6]-[C:5](=[O;D1;H0:7])-[c:4]1:[#7;a:3]:[c:2]:[nH;D2;+0:1]:[c:8]:1-[N;D1;H2:9] | null | [] | 80 | CELSIUS | 2 | HOUR | 5-Amino-N1-methyl-1H-imidazole-1,4-dicarboxamide 15 (10.72 g, 0.057 mol, 97% pure against a standard sample by HPLC analysis), Et3N (5 mL) and MeOH (100 mL) were placed into a 250 mL round-bottom flask equipped with a magnetic stir bar. The heterogeneous reaction mixture was heated at 80° C. (oil bath) for 4 hour with ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1 | HO- | CO | 80 | 2 | CNC(=O)n1cnc(C(N)=O)c1N>CO>NC(=O)c1nc[nH]c1N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-93819c7ac34e4827a4382a8241f398be | CC(C)(C)OC(=O)n1ncc2c(Cl)nc(N)nc21.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccco1>>CC(C)(C)OC(=O)n1ncc2c(-c3ccco3)nc(N)nc21 | NC1=NC(=C2C(=N1)N(N=C2)C(=O)OC(C)(C)C)Cl.C(CCC)[Sn](C=1OC=CC1)(CCCC)CCCC>>NC1=NC(=C2C(=N1)N(N=C2)C(=O)OC(C)(C)C)C=2OC=CC2 | Cl[c:12]1[c:11]2[cH:10][n:9][n:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[c:22]2[n:21][c:19]([NH2:20])[n:18]1.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:13]1[cH:14][cH:15][cH:16][o:17]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[n:8]1[n:9][cH:10][c:11]2[c:12](-[c:13]3[cH:14][cH:15][cH:16][o:17]3)[n:18][c:19]([... | CC(C)(C)OC(=O)n1ncc2c(Cl)nc(N)nc21.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccco1 | CC(C)(C)OC(=O)n1ncc2c(-c3ccco3)nc(N)nc21 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | CN(C)C=O | C-C Coupling | Stille reaction_aryl | f9398b82027a420ac418e7c872a84773666c60a8757cf355aab8e3cdbc7ff888 | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | c1coc(-c2ncnc3[nH]ncc23)c1 | C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:1]1:[#8;a:2]:[c:3]:[c:4]:[c:5]:1.Cl-[c;H0;D3;+0:6]1:[#7;a:7]:[c:8](-[N;D1;H2:9]):[#7;a:10]:[c:11]2:[#7;a:12](-[C:13](-[#8:14])=[O;D1;H0:15]):[#7;a:16]:[c:17]:[c:18]:2:1>>[#8:14]-[C:13](=[O;D1;H0:15])-[#7;a:12]1:[#7;a:16]:[c:17]:[c:18]2:[c:11]:1:[#7;a:10]:[c:8](-[... | 99 | [{"value": 99.0, "product": "NC1=NC(=C2C(=N1)N(N=C2)C(=O)OC(C)(C)C)C=2OC=CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.9, "product": "NC1=NC(=C2C(=N1)N(N=C2)C(=O)OC(C)(C)C)C=2OC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A solution of tert-butyl 6-amino-4-chloro-1H-pyrazolo[3,4-d]pyrimidine-1-carboxylate (269 mg, 1 mmol) in DMF (2 mL) was treated with PdCl2(PPh3)2 (35 mg, 0.05 mmol) and 2-(tributylstannyl)furan (315 μL, 1 mmol), stirred at room temperature for 16 h and the resulting solid filtered and washed with EtOAc to give the titl... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1ncc2c[nH]nc2n1.c1ccoc1 | c1ccoc1.c1ncc2cn[nH]c2n1 | c1ccoc1.c1ncc2cn[nH]c2n1 | HCl.Sn | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CN(C)C=O | null | 16 | CC(C)(C)OC(=O)n1ncc2c(Cl)nc(N)nc21.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccco1>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.CN(C)C=O>CC(C)(C)OC(=O)n1ncc2c(-c3ccco3)nc(N)nc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0aaf967e9712498692b57d3cf2a03587 | CC(C)(C)OC(=O)n1ncc2c(-c3ccco3)nc(N)nc21>>Nc1nc(-c2ccco2)c2cn[nH]c2n1 | NC1=NC(=C2C(=N1)N(N=C2)C(=O)OC(C)(C)C)C=2OC=CC2.CNC>>O1C(=CC=C1)C1=C2C(=NC(=N1)N)NN=C2 | CC(C)(C)OC(=O)[n:13]1[n:12][cH:11][c:10]2[c:4](-[c:5]3[cH:6][cH:7][cH:8][o:9]3)[n:3][c:2]([NH2:1])[n:15][c:14]21>>[NH2:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][o:9]2)[c:10]2[cH:11][n:12][nH:13][c:14]2[n:15]1 | CC(C)(C)OC(=O)n1ncc2c(-c3ccco3)nc(N)nc21 | Nc1nc(-c2ccco2)c2cn[nH]c2n1 | null | null | CO.O | Reduction | Boc amine deprotection | e6519cfe2577f94796ec817dc0f03a8939628aca65d631532072d83cb95adc7c | e1bf5a54b1f87284564f107662531aec2aff7de801e4606340967b38924afb28 | c1coc(-c2ncnc3[nH]ncc23)c1 | C-C(-C)(-C)-O-C(=O)-[n;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]2:[c:5]:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1>>[#7;a:2]1:[c:3]:[c:4]2:[c:5]:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:[nH;D2;+0:1]:1 | 70 | [{"value": 70.0, "product": "O1C(=CC=C1)C1=C2C(=NC(=N1)N)NN=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.4, "product": "O1C(=CC=C1)C1=C2C(=NC(=N1)N)NN=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of tert-butyl 6-amino-4-(2-furyl)-1H-pyrazolo[3,4-d]pyrimidine-1-carboxylate (204 mg, 0.68 mmol) in MeOH (2 mL) was treated with dimethylamine in water (0.5 mL, 40%), refluxed for 1 h, cooled and the resulting solid filtered and washed with water to give the title compound (95 mg, 70%) as a cream solid.
Cond... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Boc | null | c1ncc2cn[nH]c2n1 | c1ncc2c[nH]nc2n1 | c1ccoc1.c1ncc2c[nH]nc2n1 | HO- | CO.O | null | null | CC(C)(C)OC(=O)n1ncc2c(-c3ccco3)nc(N)nc21>CO.O>Nc1nc(-c2ccco2)c2cn[nH]c2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-362e4095935e451682d284f45f1e4e43 | Fc1ccccc1CBr.Nc1nc(-c2ccco2)c2cn[nH]c2n1>>Nc1nc(-c2ccco2)c2cnn(Cc3ccccc3F)c2n1 | FC1=C(CBr)C=CC=C1.O1C(=CC=C1)C1=C2C(=NC(=N1)N)NN=C2.[H-].[Na+]>>FC1=C(CN2N=CC=3C2=NC(=NC3C=3OC=CC3)N)C=CC=C1 | Br[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]1[F:21].[NH2:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][o:9]2)[c:10]2[cH:11][n:12][nH:13][c:22]2[n:23]1>>[NH2:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][o:9]2)[c:10]2[cH:11][n:12][n:13]([CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[F:21])[c:22]2[n:23]1 | Fc1ccccc1CBr.Nc1nc(-c2ccco2)c2cn[nH]c2n1 | Nc1nc(-c2ccco2)c2cnn(Cc3ccccc3F)c2n1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | aecd1c93a16dc85a9080b1c18a36716de41b59123e26fd515af4acdb6d8717f9 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cn2ncc3c(-c4ccco4)ncnc32)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7;a:5]1:[c:6]:[c:7]2:[c:8]:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:2:[nH;D2;+0:13]:1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[n;H0;D3;+0:13]1:[#7;a:5]:[c:6]:[c:7]2:[c:8]:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:2:1):[c:4] | 80.8 | [{"value": 76.0, "product": "FC1=C(CN2N=CC=3C2=NC(=NC3C=3OC=CC3)N)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.8, "product": "FC1=C(CN2N=CC=3C2=NC(=NC3C=3OC=CC3)N)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | A solution of 4-(2-furyl)-1H-pyrazolo[3,4-d]pyrimidine-6-amine (219 mg, 1 mmol) in DMF (2 mL) at 0° C. was treated with NaH (40 mg, 60%, 1 mmol), stirred for 20 min, treated with 2-fluorobenzyl bromide (120 μL, 1 mmol), stirred at room temperature for 1 h, quenched with water, extracted with EtOAc, dried (MgSO4), conce... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2c[nH]nc2n1 | c1ncc2c[nH]nc2n1 | c1ccoc1.c1ncc2c[nH]nc2n1.c1ccccc1 | HBr | CN(C)C=O | null | 0.333333 | Fc1ccccc1CBr.Nc1nc(-c2ccco2)c2cn[nH]c2n1>CN(C)C=O>Nc1nc(-c2ccco2)c2cnn(Cc3ccccc3F)c2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d3565e498df14ed8bae23550cb576b19 | Nc1nc(-c2ccco2)c2cn[nH]c2n1.O=[N+]([O-])c1cccc(CBr)c1>>Nc1nc(-c2ccco2)c2cnn(Cc3cccc([N+](=O)[O-])c3)c2n1 | O.[N+](=O)([O-])C=1C=C(CBr)C=CC1.O1C(=CC=C1)C1=C2C(=NC(=N1)N)NN=C2.[H-].[Na+]>>O1C(=CC=C1)C1=C2C(=NC(=N1)N)N(N=C2)CC2=CC(=CC=C2)[N+](=O)[O-] | [NH2:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][o:9]2)[c:10]2[cH:11][n:12][nH:13][c:24]2[n:25]1.Br[CH2:14][c:15]1[cH:16][cH:17][cH:18][c:19]([N+:20](=[O:21])[O-:22])[cH:23]1>>[NH2:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][o:9]2)[c:10]2[cH:11][n:12][n:13]([CH2:14][c:15]3[cH:16][cH:17][cH:18][c:19]([N+:20](=[O:21])[... | Nc1nc(-c2ccco2)c2cn[nH]c2n1.O=[N+]([O-])c1cccc(CBr)c1 | Nc1nc(-c2ccco2)c2cnn(Cc3cccc([N+](=O)[O-])c3)c2n1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | aecd1c93a16dc85a9080b1c18a36716de41b59123e26fd515af4acdb6d8717f9 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cn2ncc3c(-c4ccco4)ncnc32)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7;a:5]1:[c:6]:[c:7]2:[c:8]:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:2:[nH;D2;+0:13]:1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[n;H0;D3;+0:13]1:[#7;a:5]:[c:6]:[c:7]2:[c:8]:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:2:1):[c:4] | 47 | [{"value": 47.0, "product": "O1C(=CC=C1)C1=C2C(=NC(=N1)N)N(N=C2)CC2=CC(=CC=C2)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.8, "product": "O1C(=CC=C1)C1=C2C(=NC(=N1)N)N(N=C2)CC2=CC(=CC=C2)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | A solution of 4-(2-furyl)-1H-pyrazolo[3,4-d]pyrimidine-6-amine (603 mg, 3 mmol) in DMF (3 mL) at 0° C. was treated with NaH (120 mg, 60%, 3 mmol), stirred for 20 min, treated with 3-nitrobenzyl bromide (648 mg, 3 mmol), stirred at room temperature for 1 h, poured into water, extracted with EtOAc, dried (MgSO4) and conc... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ncc2c[nH]nc2n1 | c1ncc2c[nH]nc2n1 | c1ccoc1.c1ncc2c[nH]nc2n1.c1ccccc1 | HBr | CN(C)C=O | null | 0.333333 | Nc1nc(-c2ccco2)c2cn[nH]c2n1.O=[N+]([O-])c1cccc(CBr)c1>CN(C)C=O>Nc1nc(-c2ccco2)c2cnn(Cc3cccc([N+](=O)[O-])c3)c2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-19386fb71a8a42e88e53d7414f52c0a1 | Nc1nc(-c2ccco2)c2cnn(Cc3cccc([N+](=O)[O-])c3)c2n1>>Nc1cccc(Cn2ncc3c(-c4ccco4)nc(N)nc32)c1 | [OH-].[Na+].O1C(=CC=C1)C1=C2C(=NC(=N1)N)N(N=C2)CC2=CC(=CC=C2)[N+](=O)[O-].O.O.Cl[Sn]Cl>>NC=1C=C(CN2N=CC=3C2=NC(=NC3C=3OC=CC3)N)C=CC1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][n:8]2[n:9][cH:10][c:11]3[c:12](-[c:13]4[cH:14][cH:15][cH:16][o:17]4)[n:18][c:19]([NH2:20])[n:21][c:22]23)[cH:23]1>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][n:8]2[n:9][cH:10][c:11]3[c:12](-[c:13]4[cH:14][cH:15][cH:16][o:17]4)[n:18][c:19]([NH2:20])[n:21][c:22]23)[cH... | Nc1nc(-c2ccco2)c2cnn(Cc3cccc([N+](=O)[O-])c3)c2n1 | Nc1cccc(Cn2ncc3c(-c4ccco4)nc(N)nc32)c1 | null | null | CCO.Cl | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(Cn2ncc3c(-c4ccco4)ncnc32)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 115.9 | [{"value": 94.0, "product": "NC=1C=C(CN2N=CC=3C2=NC(=NC3C=3OC=CC3)N)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 115.9, "product": "NC=1C=C(CN2N=CC=3C2=NC(=NC3C=3OC=CC3)N)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 2 | HOUR | A suspension of 4-(2-furyl)-1-(3-nitrobenzyl)-1H-pyrazolo[3,4-d]pyrimidine-6-amine (396 mg, 1.18 mmol) in EtOH (5 mL) was heated to 50° C., treated with a solution of SnCl2.2H2O (798 mg, 3.54 mmol) in conc. HCl (1.8 mL), stirred at 50° C. for 2 h then heated at 70° C. for 2 h. The reaction mixture was cooled, basified ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccoc1.c1ncc2cn[nH]c2n1 | Other | CCO.Cl | 50 | 2 | Nc1nc(-c2ccco2)c2cnn(Cc3cccc([N+](=O)[O-])c3)c2n1>CCO.Cl>Nc1cccc(Cn2ncc3c(-c4ccco4)nc(N)nc32)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-df00543d4c174ad98bde971596d1cfc6 | Nc1cccc(Cn2ncc3c(-c4ccco4)nc(N)nc32)c1.O=S(=O)(Cl)c1cccs1>>Nc1nc(-c2ccco2)c2cnn(Cc3cccc(-c4ccsc4S(N)(=O)=O)c3)c2n1 | O.NC=1C=C(CN2N=CC=3C2=NC(=NC3C=3OC=CC3)N)C=CC1.S1C(=CC=C1)S(=O)(=O)Cl.N1=CC=CC=C1>>NC1=NC(=C2C(=N1)N(N=C2)CC=2C=C(C=CC2)C2=C(SC=C2)S(=O)(=O)N)C=2OC=CC2 | [NH2:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][o:9]2)[c:10]2[cH:11][n:12][n:13]([CH2:14][c:15]3[cH:16][cH:17][cH:18][c:19]([NH2:26])[cH:29]3)[c:30]2[n:31]1.Cl[S:25]([c:24]1[cH:20][cH:21][cH:22][s:23]1)(=[O:27])=[O:28]>>[NH2:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][o:9]2)[c:10]2[cH:11][n:12][n:13]([CH2:14][c:15]3... | Nc1cccc(Cn2ncc3c(-c4ccco4)nc(N)nc32)c1.O=S(=O)(Cl)c1cccs1 | Nc1nc(-c2ccco2)c2cnn(Cc3cccc(-c4ccsc4S(N)(=O)=O)c3)c2n1 | null | null | null | Acylation | OtherReaction | 645a9519bcf636b0f611cfe9c69b5a7dd7f47db935f97ddc9965e66e02c658a7 | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | c1cc(Cn2ncc3c(-c4ccco4)ncnc32)cc(-c2ccsc2)c1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4]1:[#16;a:5]:[c:6]:[c:7]:[cH;D2;+0:8]:1.[NH2;D1;+0:9]-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[NH2;D1;+0:9]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4]1:[#16;a:5]:[c:6]:[c:7]:[c;H0;D3;+0:8]:1-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14] | 22 | [{"value": 22.0, "product": "NC1=NC(=C2C(=N1)N(N=C2)CC=2C=C(C=CC2)C2=C(SC=C2)S(=O)(=O)N)C=2OC=CC2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A solution of 1-(3-aminobenzyl)-4-(2-furyl)-1H-pyrazolo[3,4-d]pyrimidine-6-amine (153 mg, 0.5 mmol) in pyridine (2 mL) was treated with 2-thiophenesulphonyl chloride (91 mg, 0.5 mmol), stirred at room temperature for 16 h, poured into water, extracted with EtOAc, dried (MgSO4), concentrated in vacuo and purified by chr... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | c1ccccc1.c1ccsc1 | c1ccccc1.c1ccsc1 | c1ccoc1.c1ncc2c[nH]nc2n1.c1ccccc1.c1ccsc1 | HCl | null | null | 16 | Nc1cccc(Cn2ncc3c(-c4ccco4)nc(N)nc32)c1.O=S(=O)(Cl)c1cccs1>>Nc1nc(-c2ccco2)c2cnn(Cc3cccc(-c4ccsc4S(N)(=O)=O)c3)c2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5e488aaa93084100a887369eb5c0f859 | CCOC(=O)Cn1ncc2c(-c3ccco3)nc(N)nc21>>Nc1nc(-c2ccco2)c2cnn(CC(=O)O)c2n1 | NC1=NC(=C2C(=N1)N(N=C2)CC(=O)OCC)C=2OC=CC2.[OH-].[Na+]>>NC1=NC(=C2C(=N1)N(N=C2)CC(=O)O)C=2OC=CC2 | CC[O:17][C:15]([CH2:14][n:13]1[n:12][cH:11][c:10]2[c:4](-[c:5]3[cH:6][cH:7][cH:8][o:9]3)[n:3][c:2]([NH2:1])[n:19][c:18]21)=[O:16]>>[NH2:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][o:9]2)[c:10]2[cH:11][n:12][n:13]([CH2:14][C:15](=[O:16])[OH:17])[c:18]2[n:19]1 | CCOC(=O)Cn1ncc2c(-c3ccco3)nc(N)nc21 | Nc1nc(-c2ccco2)c2cnn(CC(=O)O)c2n1 | null | null | CO | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1coc(-c2ncnc3[nH]ncc23)c1 | 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] | 95 | [{"value": 95.0, "product": "NC1=NC(=C2C(=N1)N(N=C2)CC(=O)O)C=2OC=CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.9, "product": "NC1=NC(=C2C(=N1)N(N=C2)CC(=O)O)C=2OC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of ethyl 6-amino-4-(2-furyl)-1H-pyrazolo[3,4-d]pyrimidin-1-ylacetate (350 mg, 1.22 mmol) in MeOH (2 mL) was treated with NaOH (1-M, 1 mL, 1 mmol), refluxed for 15 min, cooled, acidified and filtered to give the title compound (300 mg, 95%) as a white solid.
Conditions: See reaction.notes.procedure_details.
W... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccoc1.c1ncc2c[nH]nc2n1 | Other | CO | null | null | CCOC(=O)Cn1ncc2c(-c3ccco3)nc(N)nc21>CO>Nc1nc(-c2ccco2)c2cnn(CC(=O)O)c2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b725349e98b84660a46287b12d70b9d9 | Nc1ccccn1.Nc1nc(-c2ccco2)c2cnn(CC(=O)O)c2n1>>Nc1nc(-c2ccco2)c2cnn(CC(=O)Nc3ccccn3)c2n1 | NC1=NC=CC=C1.NC1=NC(=C2C(=N1)N(N=C2)CC(=O)O)C=2OC=CC2.C(=O)(C=1NC=CN1)C=1NC=CN1>>NC1=NC(=C2C(=N1)N(N=C2)CC(=O)NC2=NC=CC=C2)C=2OC=CC2 | [NH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][n:23]1.O[C:15]([CH2:14][n:13]1[n:12][cH:11][c:10]2[c:4](-[c:5]3[cH:6][cH:7][cH:8][o:9]3)[n:3][c:2]([NH2:1])[n:25][c:24]21)=[O:16]>>[NH2:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][o:9]2)[c:10]2[cH:11][n:12][n:13]([CH2:14][C:15](=[O:16])[NH:17][c:18]3[cH:19][cH:20][cH:21][cH:... | Nc1ccccn1.Nc1nc(-c2ccco2)c2cnn(CC(=O)O)c2n1 | Nc1nc(-c2ccco2)c2cnn(CC(=O)Nc3ccccn3)c2n1 | null | null | O.CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Cn1ncc2c(-c3ccco3)ncnc21)Nc1ccccn1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7;a:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[#7;a:8]:[c:9]>>[#7;a:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[#7;a:8]:[c:9] | 72.4 | [{"value": 59.0, "product": "NC1=NC(=C2C(=N1)N(N=C2)CC(=O)NC2=NC=CC=C2)C=2OC=CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.4, "product": "NC1=NC(=C2C(=N1)N(N=C2)CC(=O)NC2=NC=CC=C2)C=2OC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of 6-amino-4-(2-furyl)-1H-pyrazolo[3,4-d]pyrimidin-1-ylacetic acid (200 mg, 0.77 mmol) in DMF (3 mL) was treated with carbonyl diimidazole (125 mg, 0.77 mmol), stirred at room temperature for 2 h, treated with 2-aminopyridine (72 mg, 0.77 mmol), heated to 50° C. for 3 h, cooled and diluted with water. The re... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccoc1.c1ncc2c[nH]nc2n1.c1ccncc1 | HO- | O.CN(C)C=O | null | 2 | Nc1ccccn1.Nc1nc(-c2ccco2)c2cnn(CC(=O)O)c2n1>O.CN(C)C=O>Nc1nc(-c2ccco2)c2cnn(CC(=O)Nc3ccccn3)c2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-588ad923580f4603b6b4a120c39861a9 | Nc1nc(Cl)c2cnn(Cc3ccccc3F)c2n1.OB(O)c1cccs1>>Nc1nc(-c2cccs2)c2cnn(Cc3ccccc3F)c2n1 | ClC1=C2C(=NC(=N1)N)N(N=C2)CC2=C(C=CC=C2)F.S1C(=CC=C1)B(O)O.C(=O)(O)[O-].[Na+]>>FC1=C(CN2N=CC=3C2=NC(=NC3C=3SC=CC3)N)C=CC=C1 | Cl[c:4]1[n:3][c:2]([NH2:1])[n:23][c:22]2[c:10]1[cH:11][n:12][n:13]2[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]1[F:21].OB(O)[c:5]1[cH:6][cH:7][cH:8][s:9]1>>[NH2:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][s:9]2)[c:10]2[cH:11][n:12][n:13]([CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[F:21])[c:22]2[n:23]1 | Nc1nc(Cl)c2cnn(Cc3ccccc3F)c2n1.OB(O)c1cccs1 | Nc1nc(-c2cccs2)c2cnn(Cc3ccccc3F)c2n1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C1CCOC1.O | C-C Coupling | Suzuki coupling with boronic acids | e06111906941bce2b2dbc4ec1d779f78b0e24118e7b1dfb16b002e786659d2f2 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(Cn2ncc3c(-c4cccs4)ncnc32)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[#7;a:6](-[C:7]):[#7;a:8]:[c:9]:[c:10]:2:1.O-B(-O)-[c;H0;D3;+0:11]1:[#16;a:12]:[c:13]:[c:14]:[c:15]:1>>[C:7]-[#7;a:6]1:[#7;a:8]:[c:9]:[c:10]2:[c:5]:1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:2-[c;H0;D3;+0:11]1:[#16;a:12]:[c:13]:[c:14]:[c:15]:1 | 20 | [{"value": 20.0, "product": "FC1=C(CN2N=CC=3C2=NC(=NC3C=3SC=CC3)N)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 19.7, "product": "FC1=C(CN2N=CC=3C2=NC(=NC3C=3SC=CC3)N)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred solution of 4-chloro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-d]pyrimidine-6-amine(139 mg, 0.5 mmol) in dry THF (10 mL) was treated with 2-thiopheneboronic acid (128 mg, 1.0 mmol), Pd(PPh3)4 (50 mg, 10 mol %) and saturated aqueous NaHCO3 solution (2 mL), refluxed for 30 min, diluted with H2O, extracted with EtOAc, ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ncc2c[nH]nc2n1.c1ccsc1 | c1ccsc1.c1ncc2c[nH]nc2n1 | c1ccsc1.c1ncc2c[nH]nc2n1.c1ccccc1 | HCl.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1CCOC1.O | null | null | Nc1nc(Cl)c2cnn(Cc3ccccc3F)c2n1.OB(O)c1cccs1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1CCOC1.O>Nc1nc(-c2cccs2)c2cnn(Cc3ccccc3F)c2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cbb1bf1895cf4e479b2fbd67b4d61173 | Nc1nc(Cl)c2cnn(Cc3ccccc3F)c2n1.c1cscn1>>Nc1nc(-c2nccs2)c2cnn(Cc3ccccc3F)c2n1 | ClC1=C2C(=NC(=N1)N)N(N=C2)CC2=C(C=CC=C2)F.S1C=NC=C1.[Li]CCCC>>FC1=C(CN2N=CC=3C2=NC(=NC3C=3SC=CN3)N)C=CC=C1 | Cl[c:4]1[n:3][c:2]([NH2:1])[n:23][c:22]2[c:10]1[cH:11][n:12][n:13]2[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]1[F:21].[cH:5]1[n:6][cH:7][cH:8][s:9]1>>[NH2:1][c:2]1[n:3][c:4](-[c:5]2[n:6][cH:7][cH:8][s:9]2)[c:10]2[cH:11][n:12][n:13]([CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[F:21])[c:22]2[n:23]1 | Nc1nc(Cl)c2cnn(Cc3ccccc3F)c2n1.c1cscn1 | Nc1nc(-c2nccs2)c2cnn(Cc3ccccc3F)c2n1 | null | [Cl-].[Cl-].[Zn+2].C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C1CCOC1.[NH4+].[Cl-] | C-C Coupling | OtherReaction | 89eb3dba0d384d4d22f075a22ca4cf8a307b450e83291153a57a83b559c523da | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1ccc(Cn2ncc3c(-c4nccs4)ncnc32)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[#7;a:6](-[C:7]):[#7;a:8]:[c:9]:[c:10]:2:1.[#16;a:11]1:[c:12]:[c:13]:[#7;a:14]:[cH;D2;+0:15]:1>>[C:7]-[#7;a:6]1:[#7;a:8]:[c:9]:[c:10]2:[c:5]:1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:2-[c;H0;D3;+0:15]1:[#16;a:11]:[c:12]:[c:13]:[#7;a:14]:1 | null | [] | null | null | 15 | MINUTE | A stirred solution of thiazole (0.14 mL, 2 mmol) in dry THF (10 mL) at −78° C., under argon was treated n-BuLi (1.6-M in hexanes, 1.25 mL, 2 mmol), stirred for 15 min, treated with ZnCl2 solution (1-M in Et2O, 2 mL, 2 mmol) then allowed to warm gradually to room temperature. The mixture was treated with 4-chloro-1-(2-f... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ncc2c[nH]nc2n1.c1cscn1 | c1cscn1.c1ncc2c[nH]nc2n1 | c1cscn1.c1ncc2c[nH]nc2n1.c1ccccc1 | HCl | [Cl-].[Cl-].[Zn+2].C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1CCOC1.[NH4+].[Cl-] | null | 0.25 | Nc1nc(Cl)c2cnn(Cc3ccccc3F)c2n1.c1cscn1>[Cl-].[Cl-].[Zn+2].C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1CCOC1.[NH4+].[Cl-]>Nc1nc(-c2nccs2)c2cnn(Cc3ccccc3F)c2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e8cbd27a036f4845829de860836a32e9 | N#Cc1cnn(CCc2ccccc2)c1N.O=S(=O)(O)O>>Nc1c(C(=O)O)cnn1CCc1ccccc1 | OS(=O)(=O)O.O.NC1=C(C=NN1CCC1=CC=CC=C1)C#N.O>>NC1=C(C=NN1CCC1=CC=CC=C1)C(=O)O | N#[C:4][c:3]1[c:2]([NH2:1])[n:9]([CH2:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[n:8][cH:7]1.O=S(O)(=[O:5])[OH:6]>>[NH2:1][c:2]1[c:3]([C:4](=[O:5])[OH:6])[cH:7][n:8][n:9]1[CH2:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | N#Cc1cnn(CCc2ccccc2)c1N.O=S(=O)(O)O | Nc1c(C(=O)O)cnn1CCc1ccccc1 | null | null | null | Acylation | OtherReaction | e05c34ebe51fe654c61f91bb118ee544dcd0a035df9f073c07f2e1b77a1f299a | e722778fc7d66899e0f2f256942c8c213a77617f32bb1410d97747833c62e260 | c1ccc(CCn2cccn2)cc1 | N#[C;H0;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[#7;a:5](-[C:6]):[c:7]:1-[N;D1;H2:8].O-S(=O)(=[O;H0;D1;+0:9])-[OH;D1;+0:10]>>[C:6]-[#7;a:5]1:[#7;a:4]:[c:3]:[c:2](-[C;H0;D3;+0:1](=[O;H0;D1;+0:9])-[OH;D1;+0:10]):[c:7]:1-[N;D1;H2:8] | 47 | [{"value": 47.0, "product": "NC1=C(C=NN1CCC1=CC=CC=C1)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | A mixture of conc. H2SO4 (15 mL) and water (15 mL) was treated with 5-amino-1-(2-phenylethyl)-1H-pyrazole-4-carbonitrile (5.0 g, 23.6 mmol), heated at 60° C. for 1 h, poured into water, extracted with EtOAc, dried (MgSO4), concentrated in vacuo, and recrystallised (EtOAc/MeOH) to give the title compound (2.53 g, 47%) a... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Carboxylic acid | null | null | c1cn[nH]c1.c1ccccc1 | HO- | null | 60 | null | N#Cc1cnn(CCc2ccccc2)c1N.O=S(=O)(O)O>>Nc1c(C(=O)O)cnn1CCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ccb95d98398c434388eb28fcdff8e710 | NC(N)=O.Nc1c(C(=O)O)cnn1CCc1ccccc1>>Oc1nc(O)c2cnn(CCc3ccccc3)c2n1 | NC1=C(C=NN1CCC1=CC=CC=C1)C(=O)O.NC(=O)N>>OC1=NC(=C2C(=N1)N(N=C2)CCC2=CC=CC=C2)O | N[C:2](=[O:1])[NH2:3].O=[C:4]([OH:5])[c:6]1[cH:7][n:8][n:9]([CH2:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]1[NH2:19]>>[OH:1][c:2]1[n:3][c:4]([OH:5])[c:6]2[cH:7][n:8][n:9]([CH2:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[c:18]2[n:19]1 | NC(N)=O.Nc1c(C(=O)O)cnn1CCc1ccccc1 | Oc1nc(O)c2cnn(CCc3ccccc3)c2n1 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | 0e591787d8410c0eaba38228fe40fe90f029dc61872ef674b90b73f92e6ed2fe | abe87f6d33bcad0bc39e97e8ce81571d1d56029cc440286da14759a6ae8b96a6 | c1ccc(CCn2ncc3cncnc32)cc1 | N-[C;H0;D3;+0:1](-[NH2;D1;+0:2])=[O;H0;D1;+0:3].O=[C;H0;D3;+0:4](-[O;D1;H1:5])-[c:6]1:[c:7]:[#7;a:8]:[#7;a:9](-[C:10]):[c:11]:1-[NH2;D1;+0:12]>>[C:10]-[#7;a:9]1:[#7;a:8]:[c:7]:[c:6]2:[c:11]:1:[n;H0;D2;+0:12]:[c;H0;D3;+0:1](-[OH;D1;+0:3]):[n;H0;D2;+0:2]:[c;H0;D3;+0:4]:2-[O;D1;H1:5] | 105 | [{"value": 105.0, "product": "OC1=NC(=C2C(=N1)N(N=C2)CCC2=CC=CC=C2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 105.0, "product": "OC1=NC(=C2C(=N1)N(N=C2)CCC2=CC=CC=C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 180 | CELSIUS | null | null | A mixture of 5-amino-1-(2-phenylethyl)-1H-pyrazole-4-carboxylic acid (1.87 g, 8.1 mmol) and urea (1.46 g, 24 mmol) was heated at 180° C. for 5 h, cooled and the resulting solid suspended in boiling water, filtered and washed with water to give the impure title compound (2.18 g, 105%,) as a cream solid.
Conditions: See ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Urea.Primary amine | Aromatic alcohol.Aromatic alcohol | c1cn[nH]c1 | c1ncc2c[nH]nc2n1 | c1ncc2c[nH]nc2n1.c1ccccc1 | HO- | O | 180 | null | NC(N)=O.Nc1c(C(=O)O)cnn1CCc1ccccc1>O>Oc1nc(O)c2cnn(CCc3ccccc3)c2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5bc7b2eb36124702a954a2d96b828067 | Clc1nc(-c2ccco2)c2cnn(CCc3ccccc3)c2n1.NCCO>>OCCNc1nc(-c2ccco2)c2cnn(CCc3ccccc3)c2n1 | ClC1=NC(=C2C(=N1)N(N=C2)CCC2=CC=CC=C2)C=2OC=CC2.C(O)CN>>O1C(=CC=C1)C1=C2C(=NC(=N1)NCCO)N(N=C2)CCC2=CC=CC=C2 | Cl[c:5]1[n:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][o:12]2)[c:13]2[cH:14][n:15][n:16]([CH2:17][CH2:18][c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[c:25]2[n:26]1.[OH:1][CH2:2][CH2:3][NH2:4]>>[OH:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][o:12]2)[c:13]2[cH:14][n:15][n:16]([CH2:17][CH2:18][c:19]3[cH:20]... | Clc1nc(-c2ccco2)c2cnn(CCc3ccccc3)c2n1.NCCO | OCCNc1nc(-c2ccco2)c2cnn(CCc3ccccc3)c2n1 | null | null | CN1CCCC1=O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 72dee0a9a97243f29f8c3f5b3342432457d208ad4f129ad337c1c7c32d1e8878 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CCn2ncc3c(-c4ccco4)ncnc32)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[#7;a:4](-[C:5]):[#7;a:6]:[c:7]:[c:8]:2:[c:9]:[#7;a:10]:1.[C:11]-[C:12]-[NH2;D1;+0:13]>>[C:5]-[#7;a:4]1:[#7;a:6]:[c:7]:[c:8]2:[c:9]:[#7;a:10]:[c;H0;D3;+0:1](-[NH;D2;+0:13]-[C:12]-[C:11]):[#7;a:2]:[c:3]:1:2 | 57.2 | [{"value": 57.0, "product": "O1C(=CC=C1)C1=C2C(=NC(=N1)NCCO)N(N=C2)CCC2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.2, "product": "O1C(=CC=C1)C1=C2C(=NC(=N1)NCCO)N(N=C2)CCC2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A solution of 6-chloro-4-(2-furyl)-1-(2-phenylethyl)-1H-pyrazolo[3,4-d]pyrimidine (162 mg, 0.5 mmol) in NMP (1 mL) was treated with ethanolamine (60 μL, 1 mmol), heated at 100° C. for 16 h, cooled and purified by chromatography (EtOAc:Heptane, 2:1). The resulting colourless oil was crystallised (MeOH/water) and filtere... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncc2c[nH]nc2n1 | c1ncc2c[nH]nc2n1 | c1ccoc1.c1ncc2c[nH]nc2n1.c1ccccc1 | HCl | CN1CCCC1=O | 100 | null | Clc1nc(-c2ccco2)c2cnn(CCc3ccccc3)c2n1.NCCO>CN1CCCC1=O>OCCNc1nc(-c2ccco2)c2cnn(CCc3ccccc3)c2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-98c854739d60471ba63b9e181f7bfc00 | Nc1nc(-c2ccco2)c2cn[nH]c2n1.O=C=NCc1ccccc1>>Nc1nc(-c2ccco2)c2cnn(C(=O)NCc3ccccc3)c2n1 | O.O1C(=CC=C1)C1=C2C(=NC(=N1)N)NN=C2.C(C1=CC=CC=C1)N=C=O>>NC1=NC(=C2C(=N1)N(N=C2)C(=O)NCC2=CC=CC=C2)C=2OC=CC2 | [NH2:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][o:9]2)[c:10]2[cH:11][n:12][nH:13][c:24]2[n:25]1.[C:14](=[O:15])=[N:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[NH2:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][o:9]2)[c:10]2[cH:11][n:12][n:13]([C:14](=[O:15])[NH:16][CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22... | Nc1nc(-c2ccco2)c2cn[nH]c2n1.O=C=NCc1ccccc1 | Nc1nc(-c2ccco2)c2cnn(C(=O)NCc3ccccc3)c2n1 | null | CN(C)C=1C=CN=CC1 | CN(C)C=O | Acylation | OtherReaction | 201e4abb01f7890caf6fd4f7c0a8da3da81dda96016c3cbe15aa96536a7be958 | 3347203d95f451dc113645420a6f5b484c71b9ef5d3ed902199ccd8a70632b86 | O=C(NCc1ccccc1)n1ncc2c(-c3ccco3)ncnc21 | [#7;a:1]1:[c:2]:[c:3]2:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:2:[nH;D2;+0:9]:1.[O;D1;H0:10]=[C;H0;D2;+0:11]=[N;H0;D2;+0:12]-[C:13]-[c:14]>>[O;D1;H0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[C:13]-[c:14])-[n;H0;D3;+0:9]1:[#7;a:1]:[c:2]:[c:3]2:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:2:1 | 24 | [{"value": 24.0, "product": "NC1=NC(=C2C(=N1)N(N=C2)C(=O)NCC2=CC=CC=C2)C=2OC=CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 23.9, "product": "NC1=NC(=C2C(=N1)N(N=C2)C(=O)NCC2=CC=CC=C2)C=2OC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-(2-furyl)-1H-pyrazolo[3,4-d]pyrimidine-6-amine (210 mg, 1 mmol) in DMF (2 mL) was treated with benzyl isocyanate (123 μL, 1 mmol) and a catalytic amount of DMAP, stirred at room temperature for 1 h, poured into water, extracted with EtOAc, dried (MgSO4), concentrated in vacuo and purified by preparative... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate | Secondary amide | c1ncc2c[nH]nc2n1 | c1ncc2c[nH]nc2n1 | c1ccoc1.c1ncc2c[nH]nc2n1.c1ccccc1 | null | CN(C)C=1C=CN=CC1.CN(C)C=O | null | null | Nc1nc(-c2ccco2)c2cn[nH]c2n1.O=C=NCc1ccccc1>CN(C)C=1C=CN=CC1.CN(C)C=O>Nc1nc(-c2ccco2)c2cnn(C(=O)NCc3ccccc3)c2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b56817fc57374cc58bfa3e46d9d16bc2 | BrBr.OB(O)c1cc(F)nc(F)c1>>Fc1cc(Br)cc(F)n1 | FC1=NC(=CC(=C1)B(O)O)F.FC1=NC(=CC(=C1)NN)F.BrBr>>BrC1=CC(=NC(=C1)F)F | Br[Br:5].OB(O)[c:4]1[cH:3][c:2]([F:1])[n:9][c:7]([F:8])[cH:6]1>>[F:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][c:7]([F:8])[n:9]1 | BrBr.OB(O)c1cc(F)nc(F)c1 | Fc1cc(Br)cc(F)n1 | null | null | null | Functional Group Interconversion | OtherReaction | 7439fceb4482d21c1cec52eab8e4e8182b19280af761507babcd7e9b70fe5c29 | 66cf21c57a66a56d23ce3a3aeec0a15dd81747be7492f4ac89d5319ccb4baef6 | c1ccncc1 | Br-[Br;H0;D1;+0:1].O-B(-O)-[c;H0;D3;+0:2]1:[c:3]:[c:4](-[F;D1;H0:5]):[#7;a:6]:[c:7](-[F;D1;H0:8]):[c:9]:1>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4](-[F;D1;H0:5]):[#7;a:6]:[c:7](-[F;D1;H0:8]):[c:9]:1 | null | [] | null | null | null | null | The second step in the synthetic procedure used in synthesizing the 2,6-difluoropyridin-4-ylboronic acid involves bromination of 2,6-difluoro-4-hydrazinopyridine by elemental bromine to produce 4-bromo-2,6-difluoropyridine. This reaction can be depicted as follows:
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Boronic acid | Aromatic halide | c1ccncc1 | c1ccncc1 | c1ccncc1 | HBr.B | null | null | null | BrBr.OB(O)c1cc(F)nc(F)c1>>Fc1cc(Br)cc(F)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e872601a07df42acbedf46be66dfbffd | C=CC(=O)OC.O=Cc1ccccc1>>C=C(C(=O)OC)C(O)c1ccccc1 | N12NCC(CC1)CC2.C(C1=CC=CC=C1)=O.C(C=C)(=O)OC>>OC(C(C(=O)OC)=C)C1=CC=CC=C1 | [CH2:1]=[CH:2][C:3](=[O:4])[O:5][CH3:6].[CH:7](=[O:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[CH2:1]=[C:2]([C:3](=[O:4])[O:5][CH3:6])[CH:7]([OH:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1 | C=CC(=O)OC.O=Cc1ccccc1 | C=C(C(=O)OC)C(O)c1ccccc1 | null | null | null | C-C Coupling | OtherReaction | 5c727118385c562f285df4622fd28beee54f2a6dc613daeca0713283cec89087 | 12ce375342f37362e14813852abaca485261821306a77d2d6bbedf8a6a5866f3 | c1ccccc1 | [C;D1;H2:1]=[CH;D2;+0:2]-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6].[O;H0;D1;+0:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[C;D1;H2:1]=[C;H0;D3;+0:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6])-[CH;D3;+0:8](-[OH;D1;+0:7])-[c:9](:[c:10]):[c:11] | 77 | [{"value": 77.0, "product": "OC(C(C(=O)OC)=C)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.7, "product": "OC(C(C(=O)OC)=C)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 7 | DAY | Diazabicyclo[2.2.2]octane (5.2 g, 0.046 mol, 0.15 eq) was added to a mixture of benzaldehyde (31.5 mL, 0.309 mol, 1 eq) and methyl acrylate (42 mL, 0.464 mol, 1.5 eq). The reaction mixture was then allowed to stir at room temperature for 7 days. The reaction mixture was purified by column chromatography (eluent:hexane/... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Ester.Secondary alcohol | null | null | c1ccccc1 | null | null | null | 168 | C=CC(=O)OC.O=Cc1ccccc1>>C=C(C(=O)OC)C(O)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-955486293bfd46269894a00172777c35 | O=C(O)C(Cc1ccccc1)C(=O)O>>C=C(Cc1ccccc1)C(=O)O | Cl.C(C1=CC=CC=C1)C(C(=O)O)C(=O)O.C=O.C(C)NCC>>C=C(C(=O)O)CC1=CC=CC=C1 | O=[C:1](O)[CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[C:10](=[O:11])[OH:12]>>[CH2:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[C:10](=[O:11])[OH:12] | O=C(O)C(Cc1ccccc1)C(=O)O | C=C(Cc1ccccc1)C(=O)O | null | null | O.C(C)(=O)OCC | Miscellaneous | OtherReaction | 05c08187bcfd48bcdefffc418b1b8d1f6998c5bedcb14c599f289704901fa8bf | f72397e2bf1ed63b336420ad8491805dec3139bd28093f1f8ae2a191ad5039cf | c1ccccc1 | O-[C;H0;D3;+0:1](=O)-[CH;D3;+0:2](-[C:3]-[c:4])-[C:5](=[O;D1;H0:6])-[O;D1;H1:7]>>[CH2;D1;+0:1]=[C;H0;D3;+0:2](-[C:3]-[c:4])-[C:5](=[O;D1;H0:6])-[O;D1;H1:7] | 90 | [{"value": 90.0, "product": "C=C(C(=O)O)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.8, "product": "C=C(C(=O)O)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of benzylmalonic acid (20.0 g, 0.103 mol, 1 eq) and paraformaldehyde (4.94 g, 0.164 mol, 1.6 eq) in ethyl acetate (150 mL) was cooled (0° C.) and treated with diethylamine (10.65 mL, 0.103 mol, 1 eq) drop wise, keeping the reaction temperature below 20° C. The reaction was then warmed to reflux for 90 minute... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Vinyl | null | null | c1ccccc1 | Other | O.C(C)(=O)OCC | null | null | O=C(O)C(Cc1ccccc1)C(=O)O>O.C(C)(=O)OCC>C=C(Cc1ccccc1)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9f2d7503c50f422082db2b1fd2579b77 | CN.Cc1onc(-c2ccccc2)c1C(=O)O>>CNC(=O)c1c(-c2ccccc2)noc1C | CN(C=O)C.S(=O)(Cl)Cl.CC1=C(C(=NO1)C1=CC=CC=C1)C(=O)O.CN>>CNC(=O)C=1C(=NOC1C)C1=CC=CC=C1 | [CH3:1][NH2:2].O[C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[n:13][o:14][c:15]1[CH3:16]>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[n:13][o:14][c:15]1[CH3:16] | CN.Cc1onc(-c2ccccc2)c1C(=O)O | CNC(=O)c1c(-c2ccccc2)noc1C | null | null | ClCCCl.C(C)O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(-c2ccon2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4](-[C;D1;H3:5]):[#8;a:6]:[#7;a:7]:[c:8]:1-[c:9].[C;D1;H3:10]-[NH2;D1;+0:11]>>[C;D1;H3:5]-[c:4]1:[#8;a:6]:[#7;a:7]:[c:8](-[c:9]):[c:3]:1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:11]-[C;D1;H3:10] | null | [] | null | null | 2 | HOUR | To a suspension of 50.0 g (0.25 mol) of 5-methyl-3-phenyl-isoxazole-4-carboxylic acid in 1.2 l of 1,2-dichloroethane (DCE) is added 1.9 ml dimethyl formamide (DMF) and 21.4 ml (0.3 mol, 1.2 eq.) of thionyl chloride. The mixture is stirred for 2 h at reflux until a clear, yellow solution is formed. The solution is coole... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1cnoc1.c1ccccc1 | HO- | ClCCCl.C(C)O | null | 2 | CN.Cc1onc(-c2ccccc2)c1C(=O)O>ClCCCl.C(C)O>CNC(=O)c1c(-c2ccccc2)noc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-433f21c4ffa94d9ab075303661c50861 | CN1CCN(Cc2ccc(C#N)cc2)CC1.CNC(=O)c1c(-c2ccccc2)noc1C>>CN1CCN(Cc2ccc(-c3cc4onc(-c5ccccc5)c4c(=O)n3C)cc2)CC1 | CN1CCN(CC1)CC1=CC=C(C#N)C=C1.CNC(=O)C=1C(=NOC1C)C1=CC=CC=C1.C(CCC)[Li]>>CN1C(C2=C(C=C1C1=CC=C(C=C1)CN1CCN(CC1)C)ON=C2C2=CC=CC=C2)=O | N#[C:11][c:10]1[cH:9][cH:8][c:7]([CH2:6][N:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH2:31][CH2:30]2)[cH:29][cH:28]1.[CH3:12][c:13]1[o:14][n:15][c:16](-[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[c:23]1[C:24](=[O:25])[NH:26][CH3:27]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:6][c:7]2[cH:8][cH:9][c:10](-[c:11]3[cH:12][c:13]4[o:14][... | CN1CCN(Cc2ccc(C#N)cc2)CC1.CNC(=O)c1c(-c2ccccc2)noc1C | CN1CCN(Cc2ccc(-c3cc4onc(-c5ccccc5)c4c(=O)n3C)cc2)CC1 | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | b796e09bdeef8c81ae86573b0346b333b9a1eb62a204d48bf62aa340a787acf9 | 7c0a1e558548b78f4b861db8cc53c48cb85aa87b384bf8994f1b2fcaa0d92134 | O=c1[nH]c(-c2ccc(CN3CCNCC3)cc2)cc2onc(-c3ccccc3)c12 | N#[C;H0;D2;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[C;D1;H3:7]-[NH;D2;+0:8]-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11]1:[c:12](-[CH3;D1;+0:13]):[#8;a:14]:[#7;a:15]:[c:16]:1-[c:17]>>[C;D1;H3:7]-[n;H0;D3;+0:8]1:[c;H0;D3;+0:1](-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6]):[cH;D2;+0:13]:[c:12]2:[#8;a:14]:[#7;a:15]:[c:16](-[c... | 41.2 | [{"value": 41.0, "product": "CN1C(C2=C(C=C1C1=CC=C(C=C1)CN1CCN(CC1)C)ON=C2C2=CC=CC=C2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.2, "product": "CN1C(C2=C(C=C1C1=CC=C(C=C1)CN1CCN(CC1)C)ON=C2C2=CC=CC=C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -10 | CELSIUS | 1 | HOUR | In a 500 ml flask, 10.0 g (46.3 mmol) of 5-methyl-3-phenyl-isoxazole-4-carboxylic acid methylamide is suspended in 150 ml of tetrahydrofuran (THF) under argon. At −70° C. a solution of butyl lithium (63 ml, 1.6M in hexane, 101 mmol, 2.2 eq.) is slowly added. After 1 h at this temperature, the solution is warmed to −10°... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Secondary amide | null | c1cnoc1 | c1cc2oncc2cn1 | C1C[NH]CC[NH]1.c1ccccc1.c1cc2oncc2cn1.c1ccccc1 | Other | O1CCCC1 | -10 | 1 | CN1CCN(Cc2ccc(C#N)cc2)CC1.CNC(=O)c1c(-c2ccccc2)noc1C>O1CCCC1>CN1CCN(Cc2ccc(-c3cc4onc(-c5ccccc5)c4c(=O)n3C)cc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a28927d749e14940b77d1c3cd041bd45 | CN.Cc1noc(-c2ccccc2)c1C(=O)O>>CNC(=O)c1c(C)noc1-c1ccccc1 | CN(C)C=O.S(=O)(Cl)Cl.CC1=NOC(=C1C(=O)O)C1=CC=CC=C1.CN>>CNC(=O)C=1C(=NOC1C1=CC=CC=C1)C | [CH3:1][NH2:2].O[C:3](=[O:4])[c:5]1[c:6]([CH3:7])[n:8][o:9][c:10]1-[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6]([CH3:7])[n:8][o:9][c:10]1-[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | CN.Cc1noc(-c2ccccc2)c1C(=O)O | CNC(=O)c1c(C)noc1-c1ccccc1 | null | null | ClCCCl.C(C)O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(-c2ccno2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4](-[c:5]):[#8;a:6]:[#7;a:7]:[c:8]:1-[C;D1;H3:9].[C;D1;H3:10]-[NH2;D1;+0:11]>>[C;D1;H3:10]-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4](-[c:5]):[#8;a:6]:[#7;a:7]:[c:8]:1-[C;D1;H3:9] | null | [] | null | null | 2 | HOUR | To a suspension of 6.0 g (29.6 mmol) of 3-methyl-5-phenyl-isoxazole-4-carboxylic acid in 150 ml DCE is added 0.3 ml of DMF and 2.6 ml (35.5 mmol, 1.2 eq.) of thionyl chloride. The mixture is stirred for 2 h at reflux until a brown solution is formed. The solution is cooled to room temperature and then slowly added to a... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1cnoc1.c1ccccc1 | HO- | ClCCCl.C(C)O | null | 2 | CN.Cc1noc(-c2ccccc2)c1C(=O)O>ClCCCl.C(C)O>CNC(=O)c1c(C)noc1-c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0e553ab04cd04660a202ef9b4f2450c0 | CNC(=O)c1c(C)noc1-c1ccccc1.N#Cc1ccccc1>>Cn1c(-c2ccccc2)cc2noc(-c3ccccc3)c2c1=O | CNC(=O)C=1C(=NOC1C1=CC=CC=C1)C.C(CCC)[Li].C(C1=CC=CC=C1)#N>>CN1C(C=2C(C=C1C1=CC=CC=C1)=NOC2C2=CC=CC=C2)=O | [CH3:1][NH:2][C:22]([c:21]1[c:11]([CH3:10])[n:12][o:13][c:14]1-[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)=[O:23].N#[C:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1>>[CH3:1][n:2]1[c:3](-[c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)[cH:10][c:11]2[n:12][o:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[c:21]2[c:22]1=[O:23] | CNC(=O)c1c(C)noc1-c1ccccc1.N#Cc1ccccc1 | Cn1c(-c2ccccc2)cc2noc(-c3ccccc3)c2c1=O | null | null | C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | c94f13a18d82a7c71fc423328f39eb77b2a2ad200f3d0a1f7fb2213e00fcf36e | 7c0a1e558548b78f4b861db8cc53c48cb85aa87b384bf8994f1b2fcaa0d92134 | O=c1[nH]c(-c2ccccc2)cc2noc(-c3ccccc3)c12 | N#[C;H0;D2;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[C;D1;H3:7]-[NH;D2;+0:8]-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11]1:[c:12](-[CH3;D1;+0:13]):[#7;a:14]:[#8;a:15]:[c:16]:1-[c:17]>>[C;D1;H3:7]-[n;H0;D3;+0:8]1:[c;H0;D3;+0:9](=[O;D1;H0:10]):[c:11]2:[c:12](:[#7;a:14]:[#8;a:15]:[c:16]:2-[c:17]):[cH;D2;+0:13]:[c;H0;D3;+0:1... | 48.9 | [{"value": 48.0, "product": "CN1C(C=2C(C=C1C1=CC=CC=C1)=NOC2C2=CC=CC=C2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.9, "product": "CN1C(C=2C(C=C1C1=CC=CC=C1)=NOC2C2=CC=CC=C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | 159 mg (0.73 mmol) of 3-methyl-5-phenyl-isoxazole-4-carboxylic acid methylamide is suspended in 4 ml of THF under argon. At −5° C. a solution of butyl lithium (1.0 ml, 1.6M in hexane, 1.6 mmol, 2.2 eq.) is slowly added. After 1 h at this temperature, the solution is warmed to 0° C. and 0.92 ml (0.88 mmol, 1.2 eq.) of b... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Secondary amide | null | c1cnoc1 | c1cc2nocc2cn1 | c1ccccc1.c1cc2nocc2cn1.c1ccccc1 | Other | C1CCOC1 | 0 | 1 | CNC(=O)c1c(C)noc1-c1ccccc1.N#Cc1ccccc1>C1CCOC1>Cn1c(-c2ccccc2)cc2noc(-c3ccccc3)c2c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b2a7a735024242189307b0a478130651 | CNC(=O)c1c(C)noc1-c1ccccc1.COC(=O)c1ccc(C=O)cc1>>COC(=O)c1ccc(-c2cc3noc(-c4ccccc4)c3c(=O)n2C)cc1 | CNC(=O)C=1C(=NOC1C1=CC=CC=C1)C.COC(C1=CC=C(C=C1)C=O)=O>>COC(C1=CC=C(C=C1)C1=CC=2C(C(N1C)=O)=C(ON2)C2=CC=CC=C2)=O | [CH3:10][c:11]1[n:12][o:13][c:14](-[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[c:21]1[C:22](=[O:23])[NH:24][CH3:25].O=[CH:9][c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:27][cH:26]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][c:11]3[n:12][o:13][c:14](-[c:15]4[cH:16][cH:17][cH:18][cH:19][cH... | CNC(=O)c1c(C)noc1-c1ccccc1.COC(=O)c1ccc(C=O)cc1 | COC(=O)c1ccc(-c2cc3noc(-c4ccccc4)c3c(=O)n2C)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 72ca0f3a7bc3975934ee3feddb9e7003dea8830db718c8b5ee8d5cb61be0df59 | 5205daa3b251e517090a942fbe97f39c4526f1aa18783f08c500911f18c19c00 | O=c1[nH]c(-c2ccccc2)cc2noc(-c3ccccc3)c12 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[C;D1;H3:7]-[NH;D2;+0:8]-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11]1:[c:12](-[CH3;D1;+0:13]):[#7;a:14]:[#8;a:15]:[c:16]:1-[c:17]>>[C;D1;H3:7]-[n;H0;D3;+0:8]1:[c;H0;D3;+0:9](=[O;D1;H0:10]):[c:11]2:[c:12](:[#7;a:14]:[#8;a:15]:[c:16]:2-[c:17]):[cH;D2;+0:13]:[c;H0;D3;+0:1]:... | null | [] | null | null | null | null | This compound is obtained using 3-methyl-5-phenyl-isoxazole-4-carboxylic acid methylamide and 4-formyl-benzoic acid methyl ester in 15% as a beige solid. Mass spectrum: m/z (M+H)+: 361.2
Conditions: See reaction.notes.procedure_details.
Workup: This compound is obtained | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amide | null | c1cnoc1 | c1cc2nocc2cn1 | c1ccccc1.c1cc2nocc2cn1.c1ccccc1 | HO- | null | null | null | CNC(=O)c1c(C)noc1-c1ccccc1.COC(=O)c1ccc(C=O)cc1>>COC(=O)c1ccc(-c2cc3noc(-c4ccccc4)c3c(=O)n2C)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-99c9a33baecf43dd9a0f32dfc95cd8a1 | CNC(=O)c1c(-c2ccccc2Cl)noc1C.O=Cc1ccc2c(c1)OCO2>>Cn1c(-c2ccc3c(c2)OCO3)cc2onc(-c3ccccc3Cl)c2c1=O | CNC(=O)C=1C(=NOC1C)C1=C(C=CC=C1)Cl.O1COC2=C1C=CC(=C2)C=O>>O1COC2=C1C=CC(=C2)C2=CC1=C(C(N2C)=O)C(=NO1)C1=C(C=CC=C1)Cl | [CH3:1][NH:2][C:26]([c:25]1[c:14]([CH3:13])[o:15][n:16][c:17]1-[c:18]1[cH:19][cH:20][cH:21][cH:22][c:23]1[Cl:24])=[O:27].O=[CH:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[O:10][CH2:11][O:12]2>>[CH3:1][n:2]1[c:3](-[c:4]2[cH:5][cH:6][c:7]3[c:8]([cH:9]2)[O:10][CH2:11][O:12]3)[cH:13][c:14]2[o:15][n:16][c:17](-[c:18]3[cH:19][c... | CNC(=O)c1c(-c2ccccc2Cl)noc1C.O=Cc1ccc2c(c1)OCO2 | Cn1c(-c2ccc3c(c2)OCO3)cc2onc(-c3ccccc3Cl)c2c1=O | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 13494047fa2cb4401ee616f02b33549cb62c75a1c4aef22be9a5d3a871da91d6 | 5205daa3b251e517090a942fbe97f39c4526f1aa18783f08c500911f18c19c00 | O=c1[nH]c(-c2ccc3c(c2)OCO3)cc2onc(-c3ccccc3)c12 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6]-[#8:7].[C;D1;H3:8]-[NH;D2;+0:9]-[C;H0;D3;+0:10](=[O;D1;H0:11])-[c:12]1:[c:13](-[CH3;D1;+0:14]):[#8;a:15]:[#7;a:16]:[c:17]:1-[c:18]>>[#8:7]-[c:6]:[c:5]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]1:[cH;D2;+0:14]:[c:13]2:[#8;a:15]:[#7;a:16]:[c:17](-[c:18]):[c:12]:2:[c;H0;D3;+0:10... | null | [] | null | null | null | null | This compound is obtained using 3-(2-chloro-phenyl)-5-methyl-isoxazole-4-carboxylic acid methylamide and benzo[1,3]dioxole-5-carbaldehyde in 35% as a beige solid. Mass spectrum: m/z (M+H)+: 380.9, 382.9
Conditions: See reaction.notes.procedure_details.
Workup: This compound is obtained | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amide | null | c1cnoc1 | c1cc2oncc2cn1 | c1ccc2c(c1)OCO2.c1cc2oncc2cn1.c1ccccc1 | HO- | null | null | null | CNC(=O)c1c(-c2ccccc2Cl)noc1C.O=Cc1ccc2c(c1)OCO2>>Cn1c(-c2ccc3c(c2)OCO3)cc2onc(-c3ccccc3Cl)c2c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f214d5cbf2a241b5a58c6a1faf760ae1 | Cn1c(-c2ccc(CBr)cc2)cc2onc(-c3ccccc3)c2c1=O.c1cc[nH]c1>>Cn1c(-c2ccc(Cn3cccc3)cc2)cc2onc(-c3ccccc3)c2c1=O | BrCC1=CC=C(C=C1)C1=CC2=C(C(N1C)=O)C(=NO2)C2=CC=CC=C2.C([O-])([O-])=O.[Cs+].[Cs+].N1C=CC=C1>>CN1C(C2=C(C=C1C1=CC=C(C=C1)CN1C=CC=C1)ON=C2C2=CC=CC=C2)=O | Br[CH2:8][c:7]1[cH:6][cH:5][c:4](-[c:3]2[n:2]([CH3:1])[c:28](=[O:29])[c:27]3[c:17]([cH:16]2)[o:18][n:19][c:20]3-[c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[cH:15][cH:14]1.[nH:9]1[cH:10][cH:11][cH:12][cH:13]1>>[CH3:1][n:2]1[c:3](-[c:4]2[cH:5][cH:6][c:7]([CH2:8][n:9]3[cH:10][cH:11][cH:12][cH:13]3)[cH:14][cH:15]2)[cH:16]... | Cn1c(-c2ccc(CBr)cc2)cc2onc(-c3ccccc3)c2c1=O.c1cc[nH]c1 | Cn1c(-c2ccc(Cn3cccc3)cc2)cc2onc(-c3ccccc3)c2c1=O | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ed81cee7c9cb1b5c2931f1dacbfdcf63d83b311ec7685759e6b229eee13149ed | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c(-c2ccc(Cn3cccc3)cc2)cc2onc(-c3ccccc3)c12 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[c:5]1:[c:6]:[c:7]:[c:8]:[nH;D2;+0:9]:1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[n;H0;D3;+0:9]1:[c:5]:[c:6]:[c:7]:[c:8]:1):[c:4] | 18 | [{"value": 18.0, "product": "CN1C(C2=C(C=C1C1=CC=C(C=C1)CN1C=CC=C1)ON=C2C2=CC=CC=C2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 17.8, "product": "CN1C(C2=C(C=C1C1=CC=C(C=C1)CN1C=CC=C1)ON=C2C2=CC=CC=C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of 198 mg (0.5 mmol) of 6-(4-bromomethyl-phenyl)-5-methyl-3-phenyl-5H-isoxazolo[4,5-c]pyridin-4-one in 2.5 ml of DMF is added 326 mg (1.0 mmol, 2.0 eq.) of caesium carbonate and 0.05 ml (0.6 mmol, 1.2 eq.) of pyrrole. After stirring 16 h at room temperature the solvent is removed in vacuo and the residue ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cc[nH]c1 | c1cc[nH]c1 | c1ccccc1.c1cc[nH]c1.c1cc2oncc2cn1.c1ccccc1 | HBr | CN(C)C=O | null | 16 | Cn1c(-c2ccc(CBr)cc2)cc2onc(-c3ccccc3)c2c1=O.c1cc[nH]c1>CN(C)C=O>Cn1c(-c2ccc(Cn3cccc3)cc2)cc2onc(-c3ccccc3)c2c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9383343bf1f34e75aa73808efae7bd08 | Brc1cccc2[nH]ccc12.CC(C)[Si](Cl)(C(C)C)C(C)C>>CC(C)[Si](C(C)C)(C(C)C)n1ccc2c(Br)cccc21 | [H-].[Na+].BrC1=C2C=CNC2=CC=C1.C(C)(C)[Si](C(C)C)(C(C)C)Cl>>BrC1=C2C=CN(C2=CC=C1)[Si](C(C)C)(C(C)C)C(C)C | [nH:11]1[cH:12][cH:13][c:14]2[c:15]([Br:16])[cH:17][cH:18][cH:19][c:20]12.Cl[Si:4]([CH:2]([CH3:1])[CH3:3])([CH:5]([CH3:6])[CH3:7])[CH:8]([CH3:9])[CH3:10]>>[CH3:1][CH:2]([CH3:3])[Si:4]([CH:5]([CH3:6])[CH3:7])([CH:8]([CH3:9])[CH3:10])[n:11]1[cH:12][cH:13][c:14]2[c:15]([Br:16])[cH:17][cH:18][cH:19][c:20]12 | Brc1cccc2[nH]ccc12.CC(C)[Si](Cl)(C(C)C)C(C)C | CC(C)[Si](C(C)C)(C(C)C)n1ccc2c(Br)cccc21 | null | null | CN(C)C=O.C(Cl)Cl | Protection | OtherReaction | 77e6bebf697ec07a2748708b667c97448f4a383166abddfb073b0c244529d95f | f0dce65f75d702dc7e016c0abdb24b26134ae5c509e2d0da4a21967fb59ed09d | c1ccc2[nH]ccc2c1 | Cl-[Si;H0;D4;+0:1](-[C:2](-[C;D1;H3:3])-[C;D1;H3:4])(-[C:5](-[C;D1;H3:6])-[C;D1;H3:7])-[C:8](-[C;D1;H3:9])-[C;D1;H3:10].[c:11]:[c:12]1:[c:13]:[c:14]:[c:15]:[nH;D2;+0:16]:1>>[C;D1;H3:9]-[C:8](-[C;D1;H3:10])-[Si;H0;D4;+0:1](-[C:2](-[C;D1;H3:3])-[C;D1;H3:4])(-[C:5](-[C;D1;H3:6])-[C;D1;H3:7])-[n;H0;D3;+0:16]1:[c:15]:[c:14]... | 63 | [{"value": 63.0, "product": "BrC1=C2C=CN(C2=CC=C1)[Si](C(C)C)(C(C)C)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.6, "product": "BrC1=C2C=CN(C2=CC=C1)[Si](C(C)C)(C(C)C)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | The NaH 60% dispersion in oil (0.94 g, 23.4 mmol) was added to a solution of 4-bromoindole (3.07 g, 15.6 mmol) and triisopropylsilyl chloride (3.62 g, 18.8 mmol) in CH2Cl2 (50 mL) and DMF (2 mL). The reaction was stirred at room temperature for 1 h and quenched with water. The insoluble material was filtered off and th... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | Silyl protective group | c1ccc2[nH]ccc2c1 | c1cccc2[nH]ccc12 | c1cccc2[nH]ccc12 | HCl | CN(C)C=O.C(Cl)Cl | null | 1 | Brc1cccc2[nH]ccc12.CC(C)[Si](Cl)(C(C)C)C(C)C>CN(C)C=O.C(Cl)Cl>CC(C)[Si](C(C)C)(C(C)C)n1ccc2c(Br)cccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dd1e98bf82a04769a645501fc6827542 | CC(C)(C)[O-].CC(C)(C)[Si](C)(C)Cl.Clc1cccc2[nH]ccc12>>CC(C)(C)n1c([Si](C)(C)C)cc2c(Cl)cccc21 | ClC1=C2C=CNC2=CC=C1.CC(C)(C)[O-].[K+].C(C)(C)(C)[Si](Cl)(C)C>>C(C)(C)(C)N1C(=CC2=C(C=CC=C12)Cl)[Si](C)(C)C | [O-][C:2]([CH3:1])([CH3:3])[CH3:4].CC(C)([Si:7](Cl)([CH3:8])[CH3:10])[CH3:9].[nH:5]1[cH:6][cH:11][c:12]2[c:13]([Cl:14])[cH:15][cH:16][cH:17][c:18]12>>[CH3:1][C:2]([CH3:3])([CH3:4])[n:5]1[c:6]([Si:7]([CH3:8])([CH3:9])[CH3:10])[cH:11][c:12]2[c:13]([Cl:14])[cH:15][cH:16][cH:17][c:18]12 | CC(C)(C)[O-].CC(C)(C)[Si](C)(C)Cl.Clc1cccc2[nH]ccc12 | CC(C)(C)n1c([Si](C)(C)C)cc2c(Cl)cccc21 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 4321cf71b7c0e68d6f935f6c1112ddc958e1d92a18456a32059325244045d630 | 7e544f129a5f3bede759508be0aaeb49ea2d4df900c04da8453fd1dbb958da88 | c1ccc2[nH]ccc2c1 | C-C(-C)(-[CH3;D1;+0:1])-[Si;H0;D4;+0:2](-Cl)(-[C;D1;H3:3])-[C;D1;H3:4].[C;D1;H3:5]-[C;H0;D4;+0:6](-[C;D1;H3:7])(-[C;D1;H3:8])-[O-].[c:9]:[c:10]1:[c:11]:[c:12]:[cH;D2;+0:13]:[nH;D2;+0:14]:1>>[C;D1;H3:3]-[Si;H0;D4;+0:2](-[C;D1;H3:4])(-[CH3;D1;+0:1])-[c;H0;D3;+0:13]1:[c:12]:[c:11]:[c:10](:[c:9]):[n;H0;D3;+0:14]:1-[C;H0;D4... | 78 | [{"value": 78.0, "product": "C(C)(C)(C)N1C(=CC2=C(C=CC=C12)Cl)[Si](C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.2, "product": "C(C)(C)(C)N1C(=CC2=C(C=CC=C12)Cl)[Si](C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 5 | MINUTE | 4-Chloroindole (131.1 g, 0.871 mol) was dissolved in dry THF (0.5 L). The solution was chilled to 0° C. (ice bath, stirring). t-BuOK (97.6 g, 0.871 mol) was added in one portion and the stirring was continued for additional 5 minutes. Tert-butyldimethylchlorosilane (131 .3 g, 0.871 mol) was added portionwise over 10 mi... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | Silyl protective group | c1ccc2[nH]ccc2c1 | c1cc2ccccc2[nH]1 | c1cc2ccccc2[nH]1 | HCl | C1CCOC1 | 0 | 0.083333 | CC(C)(C)[O-].CC(C)(C)[Si](C)(C)Cl.Clc1cccc2[nH]ccc12>C1CCOC1>CC(C)(C)n1c([Si](C)(C)C)cc2c(Cl)cccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d39b22a8d24447479efd986dc0b1afc9 | CC(C)(C)OC(=O)N1CCNCC1.CC(C)(C)[Si](C)(C)n1ccc2c(Cl)cccc21>>CC(C)(C)OC(=O)N1CCN(c2cccc3c2ccn3[Si](C)(C)C(C)(C)C)CC1 | [Si](C)(C)(C(C)(C)C)N1C=CC2=C(C=CC=C12)Cl.OP(=O)(O)[O-].[K+].C1(CCCCC1)P(C1=C(C=CC=C1)C1=CC=CC=C1)C1CCCCC1.C(C)(C)(C)O[Na].N1(CCNCC1)C(=O)OC(C)(C)C>>[Si](C)(C)(C(C)(C)C)N1C=CC2=C(C=CC=C12)N1CCN(CC1)C(=O)OC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:28][CH2:29]1.Cl[c:12]1[cH:13][cH:14][cH:15][c:16]2[c:17]1[cH:18][cH:19][n:20]2[Si:21]([CH3:22])([CH3:23])[C:24]([CH3:25])([CH3:26])[CH3:27]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][... | CC(C)(C)OC(=O)N1CCNCC1.CC(C)(C)[Si](C)(C)n1ccc2c(Cl)cccc21 | CC(C)(C)OC(=O)N1CCN(c2cccc3c2ccn3[Si](C)(C)C(C)(C)C)CC1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 2bd3f0e7b0c672752798f8ae9143cd0c09f108cad412ec7b05ce2725693ded28 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cc(N2CCNCC2)c2cc[nH]c2c1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6](-[#14:7](-[C:8])(-[C;D1;H3:9])-[C;D1;H3:10]):[c:11]:[c:12]:[c:13]:2:1.[#7:14]1-[C:15]-[C:16]-[NH;D2;+0:17]-[C:18]-[C:19]-1>>[C:8]-[#14:7](-[C;D1;H3:9])(-[C;D1;H3:10])-[#7;a:6]1:[c:11]:[c:12]:[c:13]2:[c:5]:1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:2-[N;H0;D3;+0:17]1-[C:18]-[... | null | [] | null | null | null | null | The compound was prepared according to Method 2 from N-tert-butyldimethylsilyl -4-chloroindole (100 g, 376 mmol, 1 equiv.), tert-butyl 1-piperazinecarboxylate (84 g, 451 mmol), Palladium(II) acetate (1.26 g., 5.62 mmol, 2%), 2-(dicyclohexylphosphino)-biphenyl (3.95 g., 11.28 mmol, 4 mol %), tert-BuONa (50 g, 520 mmol, ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1cccc2[nH]ccc12 | C1C[NH]CC[NH]1.c1cccc2[nH]ccc12 | C1C[NH]CC[NH]1.c1cccc2[nH]ccc12 | HCl | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)C | null | null | CC(C)(C)OC(=O)N1CCNCC1.CC(C)(C)[Si](C)(C)n1ccc2c(Cl)cccc21>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)C>CC(C)(C)OC(=O)N1CCN(c2cccc3c2ccn3[Si](C)(C)C(C)(C)C)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d34fb486e4584bdcb5636a56b735f851 | CC(C)(C)OC(=O)N1CCN(c2cccc3[nH]ccc23)CC1.Cc1cc(C)c(S(=O)(=O)Cl)c(C)c1>>Cc1cc(C)c(S(=O)(=O)n2ccc3c(N4CCNCC4)cccc32)c(C)c1.Cl | C(=O)(OC(C)(C)C)N1CCN(CC1)C1=C2C=CNC2=CC=C1.C1(=C(C(=CC(=C1)C)C)S(=O)(=O)Cl)C>>Cl.C1(=C(C(=CC(=C1)C)C)S(=O)(=O)N1C=CC2=C(C=CC=C12)N1CCNCC1)C | CC(C)(C)OC(=O)[N:18]1[CH2:17][CH2:16][N:15]([c:14]2[c:13]3[cH:12][cH:11][nH:10][c:24]3[cH:23][cH:22][cH:21]2)[CH2:20][CH2:19]1.[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([S:7](=[O:8])(=[O:9])[Cl:28])[c:25]([CH3:26])[cH:27]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([S:7](=[O:8])(=[O:9])[n:10]2[cH:11][cH:12][c:13]3[c:14]([N:1... | CC(C)(C)OC(=O)N1CCN(c2cccc3[nH]ccc23)CC1.Cc1cc(C)c(S(=O)(=O)Cl)c(C)c1 | Cc1cc(C)c(S(=O)(=O)n2ccc3c(N4CCNCC4)cccc32)c(C)c1.Cl | null | null | null | Acylation | OtherReaction | db6ec236bb0a8969d8160e760ffaead5f936320ba811556d2d7c87eb633e6115 | 4d4f95a7785be3264211966e8ac4b186fff0a8bb2f1a1e9cbc5fb45f2292e89d | O=S(=O)(c1ccccc1)n1ccc2c(N3CCNCC3)cccc21 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[c:7]:[c:8]1:[c:9]:[c:10]:[c:11]:[nH;D2;+0:12]:1.[Cl;H0;D1;+0:13]-[S;H0;D4;+0:14](=[O;D1;H0:15])(=[O;D1;H0:16])-[c:17](:[c:18]):[c:19]>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1.[O;D1;H0:15]=[S;H0;D4;+0:14](=[O;D1;H0:16])(-[c:17](:[c:18]):[c:19])... | null | [] | null | null | null | null | The title compound was prepared from 4-(4-boc-piperazinyl)-indole and mesitylsulfonylchloride according to Method 3: 1H NMR (270 MHz, DMSO-d6) δ 9.10 (br, 1 H), 7.71 (d, J=5 Hz, 1 H), 7.40–7.20 (m, 3 H), 7.00–6.80 (m, 2 H), 6.51 (d, J=8 Hz, 1 H), 3.30–3.20 (m, 8 H), 2.41 (s, 6 H), 2.27 (s, 3 H); MS (ESI+) for m/z 384 (... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Sulfonyl halide.Boc | Secondary amine | C1C[NH]CC[NH]1.c1ccc2[nH]ccc2c1 | C1C[NH]CCN1.c1cccc2[nH]ccc12 | c1ccccc1.C1C[NH]CCN1.c1cccc2[nH]ccc12 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCN(c2cccc3[nH]ccc23)CC1.Cc1cc(C)c(S(=O)(=O)Cl)c(C)c1>>Cc1cc(C)c(S(=O)(=O)n2ccc3c(N4CCNCC4)cccc32)c(C)c1.Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0dd7577b1cbb45b08b04256982872821 | CC(C)(C)OC(=O)N1CCN(c2cccc3[nH]ccc23)CC1.O=S(=O)(Cl)c1cccc2ccccc12>>Cl.O=S(=O)(c1cccc2ccccc12)n1ccc2c(N3CCNCC3)cccc21 | C(=O)(OC(C)(C)C)N1CCN(CC1)C1=C2C=CNC2=CC=C1.C1(=CC=CC2=CC=CC=C12)S(=O)(=O)Cl>>Cl.C1(=CC=CC2=CC=CC=C12)S(=O)(=O)N1C=CC2=C(C=CC=C12)N1CCNCC1 | CC(C)(C)OC(=O)[N:23]1[CH2:22][CH2:21][N:20]([c:19]2[c:18]3[cH:17][cH:16][nH:15][c:29]3[cH:28][cH:27][cH:26]2)[CH2:25][CH2:24]1.[Cl:1][S:3](=[O:2])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12>>[ClH:1].[O:2]=[S:3](=[O:4])([c:5]1[cH:6][cH:7][cH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12)[n:... | CC(C)(C)OC(=O)N1CCN(c2cccc3[nH]ccc23)CC1.O=S(=O)(Cl)c1cccc2ccccc12 | Cl.O=S(=O)(c1cccc2ccccc12)n1ccc2c(N3CCNCC3)cccc21 | null | null | null | Acylation | OtherReaction | db6ec236bb0a8969d8160e760ffaead5f936320ba811556d2d7c87eb633e6115 | 4d4f95a7785be3264211966e8ac4b186fff0a8bb2f1a1e9cbc5fb45f2292e89d | O=S(=O)(c1cccc2ccccc12)n1ccc2c(N3CCNCC3)cccc21 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[c:7]:[c:8]1:[c:9]:[c:10]:[c:11]:[nH;D2;+0:12]:1.[Cl;H0;D1;+0:13]-[S;H0;D4;+0:14](=[O;D1;H0:15])(=[O;D1;H0:16])-[c:17](:[c:18]):[c:19]>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1.[O;D1;H0:15]=[S;H0;D4;+0:14](=[O;D1;H0:16])(-[c:17](:[c:18]):[c:19])... | null | [] | null | null | null | null | The title compound was prepared according 4-(4-boc-piperazinyl)-indole and naphthylsulfonylchloride according to Method 3: 1H NMR (270 MHz, DMSO-d6) δ 9.03 (br, 1 H), 8.63 (d, J=8 Hz, 1 H), 8.43 (d, J=8 Hz, 1 H), 8.34 (d, J=8 Hz, 1 H), 8.15–8.05 (m, 2 H), 7.80–7.65 (m, 3 H), 7.41 (d, J=8 Hz, 1 H), 7.18 (t, J=8 Hz, 1 H)... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Sulfonyl halide.Boc | Secondary amine | C1C[NH]CC[NH]1.c1ccc2[nH]ccc2c1 | C1C[NH]CCN1.c1cccc2[nH]ccc12 | c1ccc2ccccc2c1.C1C[NH]CCN1.c1cccc2[nH]ccc12 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCN(c2cccc3[nH]ccc23)CC1.O=S(=O)(Cl)c1cccc2ccccc12>>Cl.O=S(=O)(c1cccc2ccccc12)n1ccc2c(N3CCNCC3)cccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ad9be4801a754d8082881cce7298696a | CC(C)(C)OC(=O)N1CCN(c2cccc3[nH]ccc23)CC1.O=S(=O)(Cl)c1cc(Cl)sc1Cl>>Cl.O=S(=O)(c1cc(Cl)sc1Cl)n1ccc2c(N3CCNCC3)cccc21 | C(=O)(OC(C)(C)C)N1CCN(CC1)C1=C2C=CNC2=CC=C1.ClC=1SC(=CC1S(=O)(=O)Cl)Cl>>Cl.ClC=1SC(=CC1S(=O)(=O)N1C=CC2=C(C=CC=C12)N1CCNCC1)Cl | CC(C)(C)OC(=O)[N:20]1[CH2:19][CH2:18][N:17]([c:16]2[c:15]3[cH:14][cH:13][nH:12][c:26]3[cH:25][cH:24][cH:23]2)[CH2:22][CH2:21]1.[Cl:1][S:3](=[O:2])(=[O:4])[c:5]1[cH:6][c:7]([Cl:8])[s:9][c:10]1[Cl:11]>>[ClH:1].[O:2]=[S:3](=[O:4])([c:5]1[cH:6][c:7]([Cl:8])[s:9][c:10]1[Cl:11])[n:12]1[cH:13][cH:14][c:15]2[c:16]([N:17]3[CH2:... | CC(C)(C)OC(=O)N1CCN(c2cccc3[nH]ccc23)CC1.O=S(=O)(Cl)c1cc(Cl)sc1Cl | Cl.O=S(=O)(c1cc(Cl)sc1Cl)n1ccc2c(N3CCNCC3)cccc21 | null | null | null | Acylation | OtherReaction | db6ec236bb0a8969d8160e760ffaead5f936320ba811556d2d7c87eb633e6115 | 4d4f95a7785be3264211966e8ac4b186fff0a8bb2f1a1e9cbc5fb45f2292e89d | O=S(=O)(c1ccsc1)n1ccc2c(N3CCNCC3)cccc21 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[c:7]:[c:8]1:[c:9]:[c:10]:[c:11]:[nH;D2;+0:12]:1.[Cl;D1;H0:13]-[c:14]1:[#16;a:15]:[c:16]:[c:17]:[c:18]:1-[S;H0;D4;+0:19](-[Cl;H0;D1;+0:20])(=[O;D1;H0:21])=[O;D1;H0:22]>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1.[Cl;D1;H0:13]-[c:14]1:[#16;a:15]:[c... | null | [] | null | null | null | null | The title compound was prepared from 4-(4-boc-piperazinyl)-indole and 2,5-dichloro-3-thienylsulfonyl chloride according to Method 3: 1H NMR (270 MHz, DMSO-d6) δ 9.24 (br, 1 H), 7.78 (d, J=5 Hz, 1 H), 7.72 (s, 1 H), 7.57 (d, J=8 Hz, 1 H), 7.29 (t, J=8 Hz, 1 H), 7.01 (d, J=5 Hz, 1 H), 6.86 (d, J=8 Hz, 1 H), 3.31 (m, 8 H)... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Sulfonyl halide.Boc | Secondary amine | C1C[NH]CC[NH]1.c1ccc2[nH]ccc2c1 | C1C[NH]CCN1.c1cccc2[nH]ccc12 | c1ccsc1.C1C[NH]CCN1.c1cccc2[nH]ccc12 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCN(c2cccc3[nH]ccc23)CC1.O=S(=O)(Cl)c1cc(Cl)sc1Cl>>Cl.O=S(=O)(c1cc(Cl)sc1Cl)n1ccc2c(N3CCNCC3)cccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cf519e59ac3e498dbf8b96e2bf5828fe | CC(C)(C)OC(=O)N1CCN(c2cccc3[nH]ccc23)CC1.COc1ccc(S(=O)(=O)Cl)cc1>>COc1ccc(S(=O)(=O)n2ccc3c(N4CCNCC4)cccc32)cc1.Cl | C(=O)(OC(C)(C)C)N1CCN(CC1)C1=C2C=CNC2=CC=C1.COC1=CC=C(C=C1)S(=O)(=O)Cl>>Cl.COC1=CC=C(C=C1)S(=O)(=O)N1C=CC2=C(C=CC=C12)N1CCNCC1 | CC(C)(C)OC(=O)[N:18]1[CH2:17][CH2:16][N:15]([c:14]2[c:13]3[cH:12][cH:11][nH:10][c:24]3[cH:23][cH:22][cH:21]2)[CH2:20][CH2:19]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[Cl:27])[cH:25][cH:26]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[n:10]2[cH:11][cH:12][c:13]3[c:14]([N:15]4[CH2:16][CH2... | CC(C)(C)OC(=O)N1CCN(c2cccc3[nH]ccc23)CC1.COc1ccc(S(=O)(=O)Cl)cc1 | COc1ccc(S(=O)(=O)n2ccc3c(N4CCNCC4)cccc32)cc1.Cl | null | null | null | Acylation | OtherReaction | db6ec236bb0a8969d8160e760ffaead5f936320ba811556d2d7c87eb633e6115 | 4d4f95a7785be3264211966e8ac4b186fff0a8bb2f1a1e9cbc5fb45f2292e89d | O=S(=O)(c1ccccc1)n1ccc2c(N3CCNCC3)cccc21 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[c:7]:[c:8]1:[c:9]:[c:10]:[c:11]:[nH;D2;+0:12]:1.[Cl;H0;D1;+0:13]-[S;H0;D4;+0:14](=[O;D1;H0:15])(=[O;D1;H0:16])-[c:17](:[c:18]):[c:19]>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1.[O;D1;H0:15]=[S;H0;D4;+0:14](=[O;D1;H0:16])(-[c:17](:[c:18]):[c:19])... | null | [] | null | null | null | null | The title compound was prepared from 4-(4-boc-piperazinyl)-indole and 4-methoxyphenylsulfonyl chloride according to Method 3: 1H NMR (270 MHz, DMSO-d6) δ 9.07 (br, 1 H), 7.90 (d, J=8 Hz, 2 H), 7.78 (d, J=5 Hz, 1 H), 7.61 (d, J=8 Hz, 1 H), 7.25 (t, J=8 Hz, 1 H), 7.09 (d, J=8 Hz, 2 H), 6.92 (d, J=5 Hz, 1 H), 6.68 (d, J=8... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Sulfonyl halide.Boc | Secondary amine | C1C[NH]CC[NH]1.c1ccc2[nH]ccc2c1 | C1C[NH]CCN1.c1cccc2[nH]ccc12 | c1ccccc1.C1C[NH]CCN1.c1cccc2[nH]ccc12 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCN(c2cccc3[nH]ccc23)CC1.COc1ccc(S(=O)(=O)Cl)cc1>>COc1ccc(S(=O)(=O)n2ccc3c(N4CCNCC4)cccc32)cc1.Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d86cc93f907f48b381a9d7bc63bf7406 | CC(C)(C)OC(=O)N1CCN(c2cccc3[nH]ccc23)CC1.O=S(=O)(Cl)c1ccc(F)cc1F>>Cl.O=S(=O)(c1ccc(F)cc1F)n1ccc2c(N3CCNCC3)cccc21 | C(=O)(OC(C)(C)C)N1CCN(CC1)C1=C2C=CNC2=CC=C1.FC1=C(C=CC(=C1)F)S(=O)(=O)Cl>>Cl.FC1=C(C=CC(=C1)F)S(=O)(=O)N1C=CC2=C(C=CC=C12)N1CCNCC1 | CC(C)(C)OC(=O)[N:21]1[CH2:20][CH2:19][N:18]([c:17]2[c:16]3[cH:15][cH:14][nH:13][c:27]3[cH:26][cH:25][cH:24]2)[CH2:23][CH2:22]1.[Cl:1][S:3](=[O:2])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][c:11]1[F:12]>>[ClH:1].[O:2]=[S:3](=[O:4])([c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][c:11]1[F:12])[n:13]1[cH:14][cH:15][c:16]2[c:17](... | CC(C)(C)OC(=O)N1CCN(c2cccc3[nH]ccc23)CC1.O=S(=O)(Cl)c1ccc(F)cc1F | Cl.O=S(=O)(c1ccc(F)cc1F)n1ccc2c(N3CCNCC3)cccc21 | null | null | null | Acylation | OtherReaction | db6ec236bb0a8969d8160e760ffaead5f936320ba811556d2d7c87eb633e6115 | 4d4f95a7785be3264211966e8ac4b186fff0a8bb2f1a1e9cbc5fb45f2292e89d | O=S(=O)(c1ccccc1)n1ccc2c(N3CCNCC3)cccc21 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[c:7]:[c:8]1:[c:9]:[c:10]:[c:11]:[nH;D2;+0:12]:1.[Cl;H0;D1;+0:13]-[S;H0;D4;+0:14](=[O;D1;H0:15])(=[O;D1;H0:16])-[c:17](:[c:18]):[c:19]>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1.[O;D1;H0:15]=[S;H0;D4;+0:14](=[O;D1;H0:16])(-[c:17](:[c:18]):[c:19])... | null | [] | null | null | null | null | The title compound was prepared from 4-(4-boc-piperazinyl)-indole and 2,4-di-fluorophenylsulfonylchloride according to Method 3: 1H NMR (270 MHz, DMSO-d6) δ 9.41 (br, 1 H), 8.24 (m, 1 H), 7.75 (m, 1 H), 7.58 (m, 1 H), 7.47–7.33 (m, 2 H), 7.23 (t, J=8 Hz, 1 H), 6.99 (d, J=5 Hz, 1 H), 6.70 (d, J -8 Hz, 1 H), 3.25 (m, 8 H... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Sulfonyl halide.Boc | Secondary amine | C1C[NH]CC[NH]1.c1ccc2[nH]ccc2c1 | C1C[NH]CCN1.c1cccc2[nH]ccc12 | c1ccccc1.C1C[NH]CCN1.c1cccc2[nH]ccc12 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCN(c2cccc3[nH]ccc23)CC1.O=S(=O)(Cl)c1ccc(F)cc1F>>Cl.O=S(=O)(c1ccc(F)cc1F)n1ccc2c(N3CCNCC3)cccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1abf8353d6f14c0799bcdf82ec791499 | CC(C)(C)OC(=O)N1CCN(c2cccc3[nH]ccc23)CC1.O=S(=O)(Cl)c1ccc(-c2ccccc2)cc1>>Cl.O=S(=O)(c1ccc(-c2ccccc2)cc1)n1ccc2c(N3CCNCC3)cccc21 | C(=O)(OC(C)(C)C)N1CCN(CC1)C1=C2C=CNC2=CC=C1.C1(=CC=C(C=C1)S(=O)(=O)Cl)C1=CC=CC=C1>>Cl.C1(=CC=C(C=C1)S(=O)(=O)N1C=CC2=C(C=CC=C12)N1CCNCC1)C1=CC=CC=C1 | CC(C)(C)OC(=O)[N:25]1[CH2:24][CH2:23][N:22]([c:21]2[c:20]3[cH:19][cH:18][nH:17][c:31]3[cH:30][cH:29][cH:28]2)[CH2:27][CH2:26]1.[Cl:1][S:3](=[O:2])(=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15][cH:16]1>>[ClH:1].[O:2]=[S:3](=[O:4])([c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][... | CC(C)(C)OC(=O)N1CCN(c2cccc3[nH]ccc23)CC1.O=S(=O)(Cl)c1ccc(-c2ccccc2)cc1 | Cl.O=S(=O)(c1ccc(-c2ccccc2)cc1)n1ccc2c(N3CCNCC3)cccc21 | null | null | null | Acylation | OtherReaction | db6ec236bb0a8969d8160e760ffaead5f936320ba811556d2d7c87eb633e6115 | 4d4f95a7785be3264211966e8ac4b186fff0a8bb2f1a1e9cbc5fb45f2292e89d | O=S(=O)(c1ccc(-c2ccccc2)cc1)n1ccc2c(N3CCNCC3)cccc21 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[c:7]:[c:8]1:[c:9]:[c:10]:[c:11]:[nH;D2;+0:12]:1.[Cl;H0;D1;+0:13]-[S;H0;D4;+0:14](=[O;D1;H0:15])(=[O;D1;H0:16])-[c:17](:[c:18]):[c:19]>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1.[O;D1;H0:15]=[S;H0;D4;+0:14](=[O;D1;H0:16])(-[c:17](:[c:18]):[c:19])... | null | [] | null | null | null | null | The title compound was prepared from 4-(4-boc-piperazinyl)-indole and 1,1 ′-biphenyl-4-ylsulfonyl chloride according to Method 3: 1H NMR (270 MHz, DMSO-d6) δ 9.26 (br, 1H), 8.04 (m, 2 H), 7.88 (m, 3 H), 7.67 (m, 3 H), 7.46 (m, 3 H), 7.27 (t, J=8 Hz, 1 H), 6.96 (d, J=5 Hz, 1 H), 6.80 (d, J=8 Hz, 1 H), 3.25 (m, 8 H); MS ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Sulfonyl halide.Boc | Secondary amine | C1C[NH]CC[NH]1.c1ccc2[nH]ccc2c1 | C1C[NH]CCN1.c1cccc2[nH]ccc12 | c1ccccc1.c1ccccc1.C1C[NH]CCN1.c1cccc2[nH]ccc12 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCN(c2cccc3[nH]ccc23)CC1.O=S(=O)(Cl)c1ccc(-c2ccccc2)cc1>>Cl.O=S(=O)(c1ccc(-c2ccccc2)cc1)n1ccc2c(N3CCNCC3)cccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ac0698e88e6c456cbcd88503e97c7bdc | CC(C)(C)OC(=O)N1CCN(c2cccc3[nH]ccc23)CC1.COc1ccc(S(=O)(=O)Cl)cc1OC>>COc1ccc(S(=O)(=O)n2ccc3c(N4CCNCC4)cccc32)cc1OC.Cl | C(=O)(OC(C)(C)C)N1CCN(CC1)C1=C2C=CNC2=CC=C1.COC=1C=C(C=CC1OC)S(=O)(=O)Cl>>Cl.COC=1C=C(C=CC1OC)S(=O)(=O)N1C=CC2=C(C=CC=C12)N1CCNCC1 | CC(C)(C)OC(=O)[N:18]1[CH2:17][CH2:16][N:15]([c:14]2[c:13]3[cH:12][cH:11][nH:10][c:24]3[cH:23][cH:22][cH:21]2)[CH2:20][CH2:19]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[Cl:29])[cH:25][c:26]1[O:27][CH3:28]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[n:10]2[cH:11][cH:12][c:13]3[c:14]([N:15]... | CC(C)(C)OC(=O)N1CCN(c2cccc3[nH]ccc23)CC1.COc1ccc(S(=O)(=O)Cl)cc1OC | COc1ccc(S(=O)(=O)n2ccc3c(N4CCNCC4)cccc32)cc1OC.Cl | null | null | null | Acylation | OtherReaction | db6ec236bb0a8969d8160e760ffaead5f936320ba811556d2d7c87eb633e6115 | 4d4f95a7785be3264211966e8ac4b186fff0a8bb2f1a1e9cbc5fb45f2292e89d | O=S(=O)(c1ccccc1)n1ccc2c(N3CCNCC3)cccc21 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[c:7]:[c:8]1:[c:9]:[c:10]:[c:11]:[nH;D2;+0:12]:1.[Cl;H0;D1;+0:13]-[S;H0;D4;+0:14](=[O;D1;H0:15])(=[O;D1;H0:16])-[c:17](:[c:18]):[c:19]>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1.[O;D1;H0:15]=[S;H0;D4;+0:14](=[O;D1;H0:16])(-[c:17](:[c:18]):[c:19])... | null | [] | null | null | null | null | The title compound was prepared from 4-(4-boc-piperazinyl)-indole and 3,4-dimethoxyphenylsulfonyl chloride according to Method 3: 1H NMR (270 MHz, DMSO-d6) δ 9.00 (br, 1 H), 7.82 (d, J=5 Hz, 1 H), 7.66 (d, J=8 Hz, 1 H), 7.57 (m, 1 H), 7.40 (d, J=3 Hz, 1 H), 7.24 (t, J=8 Hz, 1 H), 7.10 (d, J=8 Hz, 1 H), 6.90 (d, J=5 Hz,... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Sulfonyl halide.Boc | Secondary amine | C1C[NH]CC[NH]1.c1ccc2[nH]ccc2c1 | C1C[NH]CCN1.c1cccc2[nH]ccc12 | c1ccccc1.C1C[NH]CCN1.c1cccc2[nH]ccc12 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCN(c2cccc3[nH]ccc23)CC1.COc1ccc(S(=O)(=O)Cl)cc1OC>>COc1ccc(S(=O)(=O)n2ccc3c(N4CCNCC4)cccc32)cc1OC.Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7fe7cc4c497e4dd289fbe25c44ed2869 | CC(C)(C)OC(=O)N1CCN(c2cccc3[nH]ccc23)CC1.O=S(=O)(Cl)c1cc(Cl)ccc1Cl>>Cl.O=S(=O)(c1cc(Cl)ccc1Cl)n1ccc2c(N3CCNCC3)cccc21 | C(=O)(OC(C)(C)C)N1CCN(CC1)C1=C2C=CNC2=CC=C1.ClC1=C(C=C(C=C1)Cl)S(=O)(=O)Cl>>Cl.ClC1=C(C=C(C=C1)Cl)S(=O)(=O)N1C=CC2=C(C=CC=C12)N1CCNCC1 | CC(C)(C)OC(=O)[N:21]1[CH2:20][CH2:19][N:18]([c:17]2[c:16]3[cH:15][cH:14][nH:13][c:27]3[cH:26][cH:25][cH:24]2)[CH2:23][CH2:22]1.[Cl:1][S:3](=[O:2])(=[O:4])[c:5]1[cH:6][c:7]([Cl:8])[cH:9][cH:10][c:11]1[Cl:12]>>[ClH:1].[O:2]=[S:3](=[O:4])([c:5]1[cH:6][c:7]([Cl:8])[cH:9][cH:10][c:11]1[Cl:12])[n:13]1[cH:14][cH:15][c:16]2[c:... | CC(C)(C)OC(=O)N1CCN(c2cccc3[nH]ccc23)CC1.O=S(=O)(Cl)c1cc(Cl)ccc1Cl | Cl.O=S(=O)(c1cc(Cl)ccc1Cl)n1ccc2c(N3CCNCC3)cccc21 | null | null | null | Acylation | OtherReaction | db6ec236bb0a8969d8160e760ffaead5f936320ba811556d2d7c87eb633e6115 | 4d4f95a7785be3264211966e8ac4b186fff0a8bb2f1a1e9cbc5fb45f2292e89d | O=S(=O)(c1ccccc1)n1ccc2c(N3CCNCC3)cccc21 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[c:7]:[c:8]1:[c:9]:[c:10]:[c:11]:[nH;D2;+0:12]:1.[Cl;H0;D1;+0:13]-[S;H0;D4;+0:14](=[O;D1;H0:15])(=[O;D1;H0:16])-[c:17](:[c:18]):[c:19]>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1.[O;D1;H0:15]=[S;H0;D4;+0:14](=[O;D1;H0:16])(-[c:17](:[c:18]):[c:19])... | null | [] | null | null | null | null | The title compound was prepared according from 4-(4-boc-piperazinyl)-indole and 2,5-dichlorophenylsulfonyl chloride according to Method 3: 1H NMR (270 MHz, DMSO-d6) δ 9.09 (br, 1 H), 8.25 (d, J=3 Hz, 1 H), 7.91–7.81 (m, 2 H), 7.72 (d, J=8 Hz, 1 H), 7.36 (d, J 8 Hz, 1 H), 7.23 (t, J=8 Hz, 1 H), 6.98 (d, J 3 Hz, 1 H), 6.... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Sulfonyl halide.Boc | Secondary amine | C1C[NH]CC[NH]1.c1ccc2[nH]ccc2c1 | C1C[NH]CCN1.c1cccc2[nH]ccc12 | c1ccccc1.C1C[NH]CCN1.c1cccc2[nH]ccc12 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCN(c2cccc3[nH]ccc23)CC1.O=S(=O)(Cl)c1cc(Cl)ccc1Cl>>Cl.O=S(=O)(c1cc(Cl)ccc1Cl)n1ccc2c(N3CCNCC3)cccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-69069e0c353b479ba9ed94775a85cd30 | CC(C)(C)OC(=O)N1CCN(c2cccc3[nH]ccc23)CC1.Cc1nn(C)c(Cl)c1S(=O)(=O)Cl>>Cc1nn(C)c(Cl)c1S(=O)(=O)n1ccc2c(N3CCNCC3)cccc21.Cl | C(=O)(OC(C)(C)C)N1CCN(CC1)C1=C2C=CNC2=CC=C1.ClC1=C(C(=NN1C)C)S(=O)(=O)Cl>>Cl.ClC1=C(C(=NN1C)C)S(=O)(=O)N1C=CC2=C(C=CC=C12)N1CCNCC1 | CC(C)(C)OC(=O)[N:20]1[CH2:19][CH2:18][N:17]([c:16]2[c:15]3[cH:14][cH:13][nH:12][c:26]3[cH:25][cH:24][cH:23]2)[CH2:22][CH2:21]1.[CH3:1][c:2]1[n:3][n:4]([CH3:5])[c:6]([Cl:7])[c:8]1[S:9](=[O:10])(=[O:11])[Cl:27]>>[CH3:1][c:2]1[n:3][n:4]([CH3:5])[c:6]([Cl:7])[c:8]1[S:9](=[O:10])(=[O:11])[n:12]1[cH:13][cH:14][c:15]2[c:16]([... | CC(C)(C)OC(=O)N1CCN(c2cccc3[nH]ccc23)CC1.Cc1nn(C)c(Cl)c1S(=O)(=O)Cl | Cc1nn(C)c(Cl)c1S(=O)(=O)n1ccc2c(N3CCNCC3)cccc21.Cl | null | null | null | Acylation | OtherReaction | db6ec236bb0a8969d8160e760ffaead5f936320ba811556d2d7c87eb633e6115 | 4d4f95a7785be3264211966e8ac4b186fff0a8bb2f1a1e9cbc5fb45f2292e89d | O=S(=O)(c1cn[nH]c1)n1ccc2c(N3CCNCC3)cccc21 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[c:7]:[c:8]1:[c:9]:[c:10]:[c:11]:[nH;D2;+0:12]:1.[C;D1;H3:13]-[c:14]1:[#7;a:15]:[#7;a:16](-[C;D1;H3:17]):[c:18](-[Cl;D1;H0:19]):[c:20]:1-[S;H0;D4;+0:21](-[Cl;H0;D1;+0:22])(=[O;D1;H0:23])=[O;D1;H0:24]>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1.[C;... | null | [] | null | null | null | null | The title compound was prepared from 4-(4-boc-piperazinyl)-indole and 5-chloro-1,3-dimethyl-1H-pyrazol-4yl-sulfonyl chloride according to Method 3: 1H NMR (270 MHz, DMSO-d6) δ 9.17 (br, 1 H), 7.78 (d, J=3 Hz, 1 H), 7.49 (d, J=8 Hz, 1 H), 7.28 (t, J=8 Hz, 1 H), 6.93 (d, J=3 Hz, 1 H), 6.87 (d, J=8 Hz, 1 H), 3.72 (s, 3 H)... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Sulfonyl halide.Boc | Secondary amine | C1C[NH]CC[NH]1.c1ccc2[nH]ccc2c1 | C1C[NH]CCN1.c1cccc2[nH]ccc12 | c1cn[nH]c1.C1C[NH]CCN1.c1cccc2[nH]ccc12 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCN(c2cccc3[nH]ccc23)CC1.Cc1nn(C)c(Cl)c1S(=O)(=O)Cl>>Cc1nn(C)c(Cl)c1S(=O)(=O)n1ccc2c(N3CCNCC3)cccc21.Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-81dc0901bd474a4e965d348614b33633 | CC(C)(C)OC(=O)N1CCN(c2cccc3[nH]ccc23)CC1.O=S(=O)(Cl)c1cccnc1>>Cl.O=S(=O)(c1cccnc1)n1ccc2c(N3CCNCC3)cccc21 | C(=O)(OC(C)(C)C)N1CCN(CC1)C1=C2C=CNC2=CC=C1.N1=CC(=CC=C1)S(=O)(=O)Cl>>Cl.N1(CCNCC1)C1=C2C=CN(C2=CC=C1)S(=O)(=O)C=1C=NC=CC1 | CC(C)(C)OC(=O)[N:19]1[CH2:18][CH2:17][N:16]([c:15]2[c:14]3[cH:13][cH:12][nH:11][c:25]3[cH:24][cH:23][cH:22]2)[CH2:21][CH2:20]1.[Cl:1][S:3](=[O:2])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][n:9][cH:10]1>>[ClH:1].[O:2]=[S:3](=[O:4])([c:5]1[cH:6][cH:7][cH:8][n:9][cH:10]1)[n:11]1[cH:12][cH:13][c:14]2[c:15]([N:16]3[CH2:17][CH2:18][NH... | CC(C)(C)OC(=O)N1CCN(c2cccc3[nH]ccc23)CC1.O=S(=O)(Cl)c1cccnc1 | Cl.O=S(=O)(c1cccnc1)n1ccc2c(N3CCNCC3)cccc21 | null | null | null | Acylation | OtherReaction | db6ec236bb0a8969d8160e760ffaead5f936320ba811556d2d7c87eb633e6115 | 4d4f95a7785be3264211966e8ac4b186fff0a8bb2f1a1e9cbc5fb45f2292e89d | O=S(=O)(c1cccnc1)n1ccc2c(N3CCNCC3)cccc21 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[c:7]:[c:8]1:[c:9]:[c:10]:[c:11]:[nH;D2;+0:12]:1.[Cl;H0;D1;+0:13]-[S;H0;D4;+0:14](=[O;D1;H0:15])(=[O;D1;H0:16])-[c:17](:[c:18]):[c:19]:[#7;a:20]:[c:21]>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1.[O;D1;H0:15]=[S;H0;D4;+0:14](=[O;D1;H0:16])(-[c:17]... | null | [] | null | null | null | null | The title compound was prepared from 4-(4-boc-piperazinyl)-indole and 3-pyridinylsulfonyl chloride according to Method 3: 1H NMR (270 MHz, DMSO-d6) δ 9.37 (br, 1 H), 9.18 (d, J=3 Hz, 1 H), 8.86 (d, J=5 Hz, 1 H), 8.39 (d, J=8 Hz, 1 H), 7.85 (d, J=3 Hz, 1 H), 7.70–7.60 (m, 2 H), 7.27 (t, J=8 Hz, 1 H), 7.00 (d, J=3 Hz, 1 ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Sulfonyl halide.Boc | Secondary amine | C1C[NH]CC[NH]1.c1ccc2[nH]ccc2c1 | C1C[NH]CCN1.c1cccc2[nH]ccc12 | c1ccncc1.C1C[NH]CCN1.c1cccc2[nH]ccc12 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCN(c2cccc3[nH]ccc23)CC1.O=S(=O)(Cl)c1cccnc1>>Cl.O=S(=O)(c1cccnc1)n1ccc2c(N3CCNCC3)cccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-59b619bc204548cba155922be20a2f11 | CC(C)(C)OC(=O)N1CCN(c2cccc3[nH]ccc23)CC1.CS(=O)(=O)c1ccccc1S(=O)(=O)Cl>>CS(=O)(=O)c1ccccc1S(=O)(=O)n1ccc2c(N3CCNCC3)cccc21.Cl | C(=O)(OC(C)(C)C)N1CCN(CC1)C1=C2C=CNC2=CC=C1.CS(=O)(=O)C1=C(C=CC=C1)S(=O)(=O)Cl>>Cl.N1(CCNCC1)C1=C2C=CN(C2=CC=C1)S(=O)(=O)C1=C(C=CC=C1)S(=O)(=O)C | CC(C)(C)OC(=O)[N:22]1[CH2:21][CH2:20][N:19]([c:18]2[c:17]3[cH:16][cH:15][nH:14][c:28]3[cH:27][cH:26][cH:25]2)[CH2:24][CH2:23]1.[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[Cl:29]>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[S:11](=[O:12])(=[O:13])[n:14]... | CC(C)(C)OC(=O)N1CCN(c2cccc3[nH]ccc23)CC1.CS(=O)(=O)c1ccccc1S(=O)(=O)Cl | CS(=O)(=O)c1ccccc1S(=O)(=O)n1ccc2c(N3CCNCC3)cccc21.Cl | null | null | null | Acylation | OtherReaction | db6ec236bb0a8969d8160e760ffaead5f936320ba811556d2d7c87eb633e6115 | 4d4f95a7785be3264211966e8ac4b186fff0a8bb2f1a1e9cbc5fb45f2292e89d | O=S(=O)(c1ccccc1)n1ccc2c(N3CCNCC3)cccc21 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[c:7]:[c:8]1:[c:9]:[c:10]:[c:11]:[nH;D2;+0:12]:1.[Cl;H0;D1;+0:13]-[S;H0;D4;+0:14](=[O;D1;H0:15])(=[O;D1;H0:16])-[c:17](:[c:18]):[c:19]>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1.[O;D1;H0:15]=[S;H0;D4;+0:14](=[O;D1;H0:16])(-[c:17](:[c:18]):[c:19])... | null | [] | null | null | null | null | The title compound was prepared from 4-(4-boc-piperazinyl)-indole and 2-methylsulfonyl-phenylsulfonyl chloride according to Method 3: 1H NMR (270 MHz, DMSO-d6) δ 9.22 (br, 1 H), 8.29 (d, J=-8 Hz, 1 H), 7.99 (t, J=8 Hz, 1 H), 7.90–7.80 (m, 2 H), 7.43 (d, J=8 Hz, 1 H), 7.3 0–7.15 (m, 2 H), 7.04 (d, J=3 Hz, 1 H), 6.85 (d,... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Sulfonyl halide.Boc | Secondary amine | C1C[NH]CC[NH]1.c1ccc2[nH]ccc2c1 | C1C[NH]CCN1.c1cccc2[nH]ccc12 | c1ccccc1.C1C[NH]CCN1.c1cccc2[nH]ccc12 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCN(c2cccc3[nH]ccc23)CC1.CS(=O)(=O)c1ccccc1S(=O)(=O)Cl>>CS(=O)(=O)c1ccccc1S(=O)(=O)n1ccc2c(N3CCNCC3)cccc21.Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b9b26d41593d4cbf888182452c0f1ba4 | CC(C)(C)OC(=O)N1CCN(c2cccc3[nH]ccc23)CC1.Cc1c(S(=O)(=O)Cl)sc2ccc(Cl)cc12>>Cc1c(S(=O)(=O)n2ccc3c(N4CCNCC4)cccc32)sc2ccc(Cl)cc12.Cl | C(=O)(OC(C)(C)C)N1CCN(CC1)C1=C2C=CNC2=CC=C1.ClC=1C=CC2=C(C(=C(S2)S(=O)(=O)Cl)C)C1>>Cl.ClC=1C=CC2=C(C(=C(S2)S(=O)(=O)N2C=CC3=C(C=CC=C23)N2CCNCC2)C)C1 | CC(C)(C)OC(=O)[N:15]1[CH2:14][CH2:13][N:12]([c:11]2[c:10]3[cH:9][cH:8][nH:7][c:21]3[cH:20][cH:19][cH:18]2)[CH2:17][CH2:16]1.[CH3:1][c:2]1[c:3]([S:4](=[O:5])(=[O:6])[Cl:30])[s:22][c:23]2[cH:24][cH:25][c:26]([Cl:27])[cH:28][c:29]12>>[CH3:1][c:2]1[c:3]([S:4](=[O:5])(=[O:6])[n:7]2[cH:8][cH:9][c:10]3[c:11]([N:12]4[CH2:13][C... | CC(C)(C)OC(=O)N1CCN(c2cccc3[nH]ccc23)CC1.Cc1c(S(=O)(=O)Cl)sc2ccc(Cl)cc12 | Cc1c(S(=O)(=O)n2ccc3c(N4CCNCC4)cccc32)sc2ccc(Cl)cc12.Cl | null | null | null | Acylation | OtherReaction | db6ec236bb0a8969d8160e760ffaead5f936320ba811556d2d7c87eb633e6115 | 4d4f95a7785be3264211966e8ac4b186fff0a8bb2f1a1e9cbc5fb45f2292e89d | O=S(=O)(c1cc2ccccc2s1)n1ccc2c(N3CCNCC3)cccc21 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[c:7]:[c:8]1:[c:9]:[c:10]:[c:11]:[nH;D2;+0:12]:1.[Cl;H0;D1;+0:13]-[S;H0;D4;+0:14](=[O;D1;H0:15])(=[O;D1;H0:16])-[c:17](:[c:18]):[#16;a:19]:[c:20]>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1.[O;D1;H0:15]=[S;H0;D4;+0:14](=[O;D1;H0:16])(-[c:17](:[c:1... | 45 | [{"value": 45.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared 4-(4-boc-piperazinyl)-indole and 1-[(5-chloro-3-methyl-1-benzothien-2-yl)sulfonyl chloride according to Method 4 to afford the hydrochloride salt (yield 45%), HPLC purity >95%; 1H NMR (DMSO-d6) δ 2.65 (s, 3H), 3.26 (bs, 8H), 6.82 (app d, 1H), 7.00 (appd, 1H), 7.28 (app t, 1H), 7.60 (app ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Sulfonyl halide.Boc | Secondary amine | C1C[NH]CC[NH]1.c1ccc2[nH]ccc2c1 | C1C[NH]CCN1.c1cccc2[nH]ccc12 | C1C[NH]CCN1.c1cccc2[nH]ccc12.c1ccc2sccc2c1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCN(c2cccc3[nH]ccc23)CC1.Cc1c(S(=O)(=O)Cl)sc2ccc(Cl)cc12>>Cc1c(S(=O)(=O)n2ccc3c(N4CCNCC4)cccc32)sc2ccc(Cl)cc12.Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-681a7360d8f647d892e600b37f148d04 | CN1CCN(c2cccc3[nH]ccc23)CC1.Cc1ccc(S(=O)(=O)Cl)cc1>>Cc1ccc(S(=O)(=O)n2ccc3c(N4CCN(C)CC4)cccc32)cc1.Cl | CN1CCN(CC1)C1=C2C=CNC2=CC=C1.CC1=CC=C(C=C1)S(=O)(=O)Cl>>Cl.CN1CCN(CC1)C1=C2C=CN(C2=CC=C1)S(=O)(=O)C1=CC=C(C=C1)C | [nH:9]1[cH:10][cH:11][c:12]2[c:13]([N:14]3[CH2:15][CH2:16][N:17]([CH3:18])[CH2:19][CH2:20]3)[cH:21][cH:22][cH:23][c:24]12.[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[Cl:27])[cH:25][cH:26]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[n:9]2[cH:10][cH:11][c:12]3[c:13]([N:14]4[CH2:15][CH2:16][N:17]([CH3:... | CN1CCN(c2cccc3[nH]ccc23)CC1.Cc1ccc(S(=O)(=O)Cl)cc1 | Cc1ccc(S(=O)(=O)n2ccc3c(N4CCN(C)CC4)cccc32)cc1.Cl | null | null | null | Miscellaneous | OtherReaction | 49b0f001e680c7f73cfebff18420e826fe8710fff836cdfec6a392d7d3ed490b | 5dfa42f530316585f6465479a772e2041686a0fdee7ff836ade358eb1d56f51a | O=S(=O)(c1ccccc1)n1ccc2c(N3CCNCC3)cccc21 | [Cl;H0;D1;+0:1]-[S;H0;D4;+0:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5](:[c:6]):[c:7].[c:8]:[c:9]1:[c:10]:[c:11]:[c:12]:[nH;D2;+0:13]:1>>[ClH;D0;+0:1].[O;D1;H0:3]=[S;H0;D4;+0:2](=[O;D1;H0:4])(-[c:5](:[c:6]):[c:7])-[n;H0;D3;+0:13]1:[c:12]:[c:11]:[c:10]:[c:9]:1:[c:8] | null | [] | null | null | null | null | The title compound was prepared 4-(4-methyl-1-piperazinyl)-1H-indole and p-methylbenzenesulfonyl chloride according to Method 4 (45%): 1H NMR (CD3OD) δ 7.81–6.77 (m, 9H), 3.62–3.02 (m, 8H), 2.98 (s, 3H), 2.34 (s, 3H); MS (ESI) 370.5 (M+H)+; Purity (HPLC) >95%.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Sulfonyl halide | Tosylate | c1ccc2[nH]ccc2c1 | c1cccc2[nH]ccc12 | c1ccccc1.C1C[NH]CC[NH]1.c1cccc2[nH]ccc12 | null | null | null | null | CN1CCN(c2cccc3[nH]ccc23)CC1.Cc1ccc(S(=O)(=O)Cl)cc1>>Cc1ccc(S(=O)(=O)n2ccc3c(N4CCN(C)CC4)cccc32)cc1.Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dc1c665ddaab44ba8bee25485097fb45 | Brc1cccc2[nH]ccc12.O=S(=O)(Cl)c1ccccc1>>O=S(=O)(c1ccccc1)n1ccc2c(Br)cccc21 | BrC1=C2C=CNC2=CC=C1.C1(=CC=CC=C1)S(=O)(=O)Cl>>BrC1=C2C=CN(C2=CC=C1)S(=O)(=O)C1=CC=CC=C1 | [nH:10]1[cH:11][cH:12][c:13]2[c:14]([Br:15])[cH:16][cH:17][cH:18][c:19]12.Cl[S:2](=[O:1])(=[O:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1>>[O:1]=[S:2](=[O:3])([c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[n:10]1[cH:11][cH:12][c:13]2[c:14]([Br:15])[cH:16][cH:17][cH:18][c:19]12 | Brc1cccc2[nH]ccc12.O=S(=O)(Cl)c1ccccc1 | O=S(=O)(c1ccccc1)n1ccc2c(Br)cccc21 | null | null | null | Miscellaneous | OtherReaction | e93893efa892c31f636f9e26a164705bdf058b446e712f27dbec53ec2201b24d | 5f0d826ff827e7d94d07bc9ee74d0a88c79bcf75bb024f05043486e1cbe294bd | O=S(=O)(c1ccccc1)n1ccc2ccccc21 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[c:7]:[c:8]1:[c:9]:[c:10]:[c:11]:[nH;D2;+0:12]:1>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[c:4](:[c:5]):[c:6])-[n;H0;D3;+0:12]1:[c:11]:[c:10]:[c:9]:[c:8]:1:[c:7] | 91 | [{"value": 91.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Bromo-1-(benzenesulfonyl)-1H-indole was prepared from 4-bromoindole and phenylsulfonyl chloride according to Method 4 to afford 3.1 g (91%) of a light purple solid: 1HNMR (CDCl3) δ 7.94 (d, J=8 Hz, 1H), 7.89–7.84 (m, 2H), 7.62 (d, 4 Hz, 1H), 7.57–7.51 (m, 1H), 7.46–7.37 (m, 3H), 7.19–7.13 (m, 1H), 6.72 (dd, J=1, 4 Hz... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1ccc2[nH]ccc2c1 | c1cccc2[nH]ccc12 | c1ccccc1.c1cccc2[nH]ccc12 | HCl | null | null | null | Brc1cccc2[nH]ccc12.O=S(=O)(Cl)c1ccccc1>>O=S(=O)(c1ccccc1)n1ccc2c(Br)cccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-784afa7c18bd48648e12e646d01fb8e2 | Brc1cccc2[nH]ccc12.Cc1ccccc1S(=O)(=O)Cl>>Cc1ccccc1S(=O)(=O)n1ccc2c(Br)cccc21 | BrC1=C2C=CNC2=CC=C1.CC1=C(C=CC=C1)S(=O)(=O)Cl>>BrC1=C2C=CN(C2=CC=C1)S(=O)(=O)C1=C(C=CC=C1)C | [nH:11]1[cH:12][cH:13][c:14]2[c:15]([Br:16])[cH:17][cH:18][cH:19][c:20]12.Cl[S:8]([c:7]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]1)(=[O:9])=[O:10]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[S:8](=[O:9])(=[O:10])[n:11]1[cH:12][cH:13][c:14]2[c:15]([Br:16])[cH:17][cH:18][cH:19][c:20]12 | Brc1cccc2[nH]ccc12.Cc1ccccc1S(=O)(=O)Cl | Cc1ccccc1S(=O)(=O)n1ccc2c(Br)cccc21 | null | null | null | Miscellaneous | OtherReaction | e93893efa892c31f636f9e26a164705bdf058b446e712f27dbec53ec2201b24d | 5f0d826ff827e7d94d07bc9ee74d0a88c79bcf75bb024f05043486e1cbe294bd | O=S(=O)(c1ccccc1)n1ccc2ccccc21 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[c:7]:[c:8]1:[c:9]:[c:10]:[c:11]:[nH;D2;+0:12]:1>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[c:4](:[c:5]):[c:6])-[n;H0;D3;+0:12]1:[c:11]:[c:10]:[c:9]:[c:8]:1:[c:7] | 87 | [{"value": 87.0, "product": "BrC1=C2C=CN(C2=CC=C1)S(=O)(=O)C1=C(C=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The compound was prepared from 4-bromoindole (1.02 g, 5.25 mmol) and o-methylbenzenesulfonyl chloride (a 9:1 mixture of ortho and para methyl isomers) (1.29 g, 6.78 mmol) according to method 4. Purification by column chromatography (SiO2, CH2Cl2:heptane) gave 1.6 g (87%) of the title compound which contains ca 10% of t... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1ccc2[nH]ccc2c1 | c1cccc2[nH]ccc12 | c1ccccc1.c1cccc2[nH]ccc12 | HCl | null | null | null | Brc1cccc2[nH]ccc12.Cc1ccccc1S(=O)(=O)Cl>>Cc1ccccc1S(=O)(=O)n1ccc2c(Br)cccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1709dad3b5804316bd81b6fe75a13e7a | C1CNCCN1.Cc1ccccc1S(=O)(=O)n1ccc2c(Br)cccc21>>Cc1ccccc1S(=O)(=O)n1ccc2c(N3CCNCC3)cccc21 | BrC1=C2C=CN(C2=CC=C1)S(=O)(=O)C1=C(C=CC=C1)C.N1CCNCC1>>N1(CCNCC1)C1=C2C=CN(C2=CC=C1)S(=O)(=O)C1=C(C=CC=C1)C | [NH:16]1[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]1.Br[c:15]1[c:14]2[cH:13][cH:12][n:11]([S:8]([c:7]3[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]3)(=[O:9])=[O:10])[c:25]2[cH:24][cH:23][cH:22]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[S:8](=[O:9])(=[O:10])[n:11]1[cH:12][cH:13][c:14]2[c:15]([N:16]3[CH2:17][CH2:18][NH:19][CH2:... | C1CNCCN1.Cc1ccccc1S(=O)(=O)n1ccc2c(Br)cccc21 | Cc1ccccc1S(=O)(=O)n1ccc2c(N3CCNCC3)cccc21 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 00599bbbffced01cd2985ebc9fbf67df1bcefb20b1163f91a23a7b690b4821bf | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=S(=O)(c1ccccc1)n1ccc2c(N3CCNCC3)cccc21 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6](-[#16:7]):[c:8]:[c:9]:[c:10]:2:1.[#7:11]1-[C:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[C:16]-1>>[#16:7]-[#7;a:6]1:[c:8]:[c:9]:[c:10]2:[c:5]:1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:2-[N;H0;D3;+0:14]1-[C:13]-[C:12]-[#7:11]-[C:16]-[C:15]-1 | 12 | [{"value": 12.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared from 4-bromo-1-(2-methyl-benzenesulfonyl)-1H-indole and piperazine according to Method 1 to give 25 mg (12%) of a white solid: 1HNMR (CD3OD) δ 7.91–6.79 (m, 9H), 3.49–3.30 (m, 8H), 2.48 (s, 3H); MS (ESI) 356.1 (M+H)+; Purity (HPLC) >95%.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1cccc2[nH]ccc12 | C1C[NH]CCN1.c1cccc2[nH]ccc12 | c1ccccc1.C1C[NH]CCN1.c1cccc2[nH]ccc12 | HBr | null | null | null | C1CNCCN1.Cc1ccccc1S(=O)(=O)n1ccc2c(Br)cccc21>>Cc1ccccc1S(=O)(=O)n1ccc2c(N3CCNCC3)cccc21 |
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