dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-77a3b44cb285441d922bff942b3398e8 | CC(C)(CC(Br)C=O)[N+](=O)[O-].COc1ccc(N)nc1>>COc1ccc2ncc(CC(C)(C)[N+](=O)[O-])n2c1 | NC1=NC=C(C=C1)OC.BrC(C=O)CC(C)([N+](=O)[O-])C>>CC(CC1=CN=C2N1C=C(C=C2)OC)(C)[N+](=O)[O-] | O=[CH:8][CH:9](Br)[CH2:10][C:11]([CH3:12])([CH3:13])[N+:14](=[O:15])[O-:16].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[n:17][cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][c:9]([CH2:10][C:11]([CH3:12])([CH3:13])[N+:14](=[O:15])[O-:16])[n:17]2[cH:18]1 | CC(C)(CC(Br)C=O)[N+](=O)[O-].COc1ccc(N)nc1 | COc1ccc2ncc(CC(C)(C)[N+](=O)[O-])n2c1 | null | null | ClCCl | Aromatic Heterocycle Formation | OtherReaction | 3a7835efa5ac56b87be43234b54606ae621fc957a5ff407573e590f6174c2545 | 4efe5597cd78b75eedda88a299158b349ae1f03c7cd5a6a1daf8cec0515aae7c | c1ccn2ccnc2c1 | Br-[CH;D3;+0:1](-[C:2]-[C:3])-[CH;D2;+0:4]=O.[NH2;D1;+0:5]-[c:6](:[c:7]):[n;H0;D2;+0:8]:[c:9]:[c:10]>>[C:3]-[C:2]-[c;H0;D3;+0:1]1:[cH;D2;+0:4]:[n;H0;D2;+0:5]:[c:6](:[c:7]):[n;H0;D3;+0:8]:1:[c:9]:[c:10] | 42.1 | [{"value": 42.0, "product": "CC(CC1=CN=C2N1C=C(C=C2)OC)(C)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.1, "product": "CC(CC1=CN=C2N1C=C(C=C2)OC)(C)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Amino-5-methoxypyridine (J. Med. Chem., 24:39, 1981; 2.02 g, 16.3 mmol) and 2-bromo-4-methyl-4-nitropentanal (16.3 mmol) are reacted as described in Amine 7 and the product is isolated in two crops from the concentrated mixture by heating twice with dichloromethane (30 ml and 10 ml) and filtration without further chr... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aldehyde.Primary amine | null | c1ccncc1 | c1ccn2ccnc2c1 | c1ccn2ccnc2c1 | HBr | ClCCl | null | null | CC(C)(CC(Br)C=O)[N+](=O)[O-].COc1ccc(N)nc1>ClCCl>COc1ccc2ncc(CC(C)(C)[N+](=O)[O-])n2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5b335e29ecd2454d93b69f994db21e79 | CC(C)(Cc1cnc2c(Br)cccn12)[N+](=O)[O-].OB(O)c1cccs1>>CC(C)(Cc1cnc2c(-c3cccs3)cccn12)[N+](=O)[O-] | BrC=1C=2N(C=CC1)C(=CN2)CC(C)([N+](=O)[O-])C.C([O-])([O-])=O.[Na+].[Na+].S1C(=CC=C1)B(O)O>>CC(CC1=CN=C2N1C=CC=C2C=2SC=CC2)(C)[N+](=O)[O-] | Br[c:9]1[c:8]2[n:7][cH:6][c:5]([CH2:4][C:2]([CH3:1])([CH3:3])[N+:19](=[O:20])[O-:21])[n:18]2[cH:17][cH:16][cH:15]1.OB(O)[c:10]1[cH:11][cH:12][cH:13][s:14]1>>[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][n:7][c:8]2[c:9](-[c:10]3[cH:11][cH:12][cH:13][s:14]3)[cH:15][cH:16][cH:17][n:18]12)[N+:19](=[O:20])[O-:21] | CC(C)(Cc1cnc2c(Br)cccn12)[N+](=O)[O-].OB(O)c1cccs1 | CC(C)(Cc1cnc2c(-c3cccs3)cccn12)[N+](=O)[O-] | 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 | O1CCOCC1 | C-C Coupling | Suzuki coupling with boronic acids | 98571be3caf5ce9d306088c6a4547047cdefaf6f82db2deeccf45cb13a0ba90d | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1csc(-c2cccn3ccnc23)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]2:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:1.O-B(-O)-[c;H0;D3;+0:10]1:[#16;a:11]:[c:12]:[c:13]:[c:14]:1>>[#16;a:11]1:[c:12]:[c:13]:[c:14]:[c;H0;D3;+0:10]:1-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]2:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:1 | 100.9 | [{"value": 100.0, "product": "CC(CC1=CN=C2N1C=CC=C2C=2SC=CC2)(C)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.9, "product": "CC(CC1=CN=C2N1C=CC=C2C=2SC=CC2)(C)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A mixture of 8-bromo-3-(2-methyl-2-nitropropyl)imidazo[1,2-a]pyridine (1.5 g, 5.0 mmol), Pd(PPh3)4 (0.68 g), 2M aqueous sodium carbonate solution (8 ml), and dioxane (68 ml) is stirred for 30 minutes under an atmosphere of argon. After addition of thiophene-2-boronic acid (0.96 g, 7.5 mmol), the mixture is stirred over... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccn2ccnc2c1.c1ccsc1 | c1ccsc1.c1ccn2ccnc2c1 | c1ccsc1.c1ccn2ccnc2c1 | 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.O1CCOCC1 | null | 0.5 | CC(C)(Cc1cnc2c(Br)cccn12)[N+](=O)[O-].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.O1CCOCC1>CC(C)(Cc1cnc2c(-c3cccs3)cccn12)[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c431248d1a1748a592f5e57d93bfc4c8 | CC(C)(Cc1cnc2c(Br)cccn12)[N+](=O)[O-].OB(O)c1ccc(C(F)(F)F)cc1>>CC(C)(Cc1cnc2c(-c3ccc(C(F)(F)F)cc3)cccn12)[N+](=O)[O-] | BrC=1C=2N(C=CC1)C(=CN2)CC(C)([N+](=O)[O-])C.FC(C1=CC=C(C=C1)B(O)O)(F)F>>CC(CC1=CN=C2N1C=CC=C2C2=CC=C(C=C2)C(F)(F)F)(C)[N+](=O)[O-] | Br[c:9]1[c:8]2[n:7][cH:6][c:5]([CH2:4][C:2]([CH3:1])([CH3:3])[N+:24](=[O:25])[O-:26])[n:23]2[cH:22][cH:21][cH:20]1.OB(O)[c:10]1[cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][cH:19]1>>[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][n:7][c:8]2[c:9](-[c:10]3[cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][cH... | CC(C)(Cc1cnc2c(Br)cccn12)[N+](=O)[O-].OB(O)c1ccc(C(F)(F)F)cc1 | CC(C)(Cc1cnc2c(-c3ccc(C(F)(F)F)cc3)cccn12)[N+](=O)[O-] | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 6d2f92e38cbc7faf246cda8a4b8669001b5c18f23ff87160bd75535916dab019 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccn3ccnc23)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]2:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:1.O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[c:12]:[c:11]:[c;H0;D3;+0:10](-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]2:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:1):[c:13]:[c:14] | 101.1 | [{"value": 100.0, "product": "CC(CC1=CN=C2N1C=CC=C2C2=CC=C(C=C2)C(F)(F)F)(C)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 101.1, "product": "CC(CC1=CN=C2N1C=CC=C2C2=CC=C(C=C2)C(F)(F)F)(C)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 8-Bromo-3-(2-methyl-2-nitropropyl)imidazo[1,2-a]pyridine (1.0 g, 3.35 mmol) and 4-trifluoromethyl-benzeneboronic acid (0.96 g, 5.05 mmol) are coupled as described in Amine 14 to give 1.23 g of 3-(2-methyl-2-nitropropyl)-8-(4-trifluoromethyl-phenyl)imidazo[1,2-a]pyridine (100%).
Conditions: See reaction.notes.procedure_... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccn2ccnc2c1.c1ccccc1 | c1ccccc1.c1ccn2ccnc2c1 | c1ccccc1.c1ccn2ccnc2c1 | HBr.B | null | null | null | CC(C)(Cc1cnc2c(Br)cccn12)[N+](=O)[O-].OB(O)c1ccc(C(F)(F)F)cc1>>CC(C)(Cc1cnc2c(-c3ccc(C(F)(F)F)cc3)cccn12)[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3d7616d7c81644f786373d7d2a90de23 | CC(C)(C)OC(=O)CCl.CC(C)(Cc1cnc2c(O)cccn12)[N+](=O)[O-]>>CC(C)(C)OC(=O)COc1cccn2c(CC(C)(C)[N+](=O)[O-])cnc12 | CC(CC1=CN=C2N1C=CC=C2O)(C)[N+](=O)[O-].ClCC(=O)OC(C)(C)C.C([O-])([O-])=O.[K+].[K+].[I-].[K+]>>C(C)(C)(C)OC(COC=1C=2N(C=CC1)C(=CN2)CC(C)([N+](=O)[O-])C)=O | Cl[CH2:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[OH:9][c:10]1[cH:11][cH:12][cH:13][n:14]2[c:15]([CH2:16][C:17]([CH3:18])([CH3:19])[N+:20](=[O:21])[O-:22])[cH:23][n:24][c:25]12>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][O:9][c:10]1[cH:11][cH:12][cH:13][n:14]2[c:15]([CH2:16][C:17]([CH3:18])([CH3:1... | CC(C)(C)OC(=O)CCl.CC(C)(Cc1cnc2c(O)cccn12)[N+](=O)[O-] | CC(C)(C)OC(=O)COc1cccn2c(CC(C)(C)[N+](=O)[O-])cnc12 | null | null | CC(CC)=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | c1ccn2ccnc2c1 | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]1:[#7;a:13]:[c:14]:[c:15]:[#7;a:16]:1:[c:17]>>[C;D1;H3:6]-[C:5](-[C;D1;H3:7])(-[C;D1;H3:8])-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]1:[#7;a:13]:[c:14]:[c:15]... | 81 | [{"value": 81.0, "product": "C(C)(C)(C)OC(COC=1C=2N(C=CC1)C(=CN2)CC(C)([N+](=O)[O-])C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.8, "product": "C(C)(C)(C)OC(COC=1C=2N(C=CC1)C(=CN2)CC(C)([N+](=O)[O-])C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(2-Methyl-2-nitropropyl)imidazo[1,2-a]pyridin-8-ol (1.0 g, 4.25 mmol), tert-butyl chloroacetate (964 mg, 6.4 mmol), potassium carbonate (590 mg, 4.27 mmol), and a small amount of potassium iodide in 2-butanone (30 ml) are reacted as described in Amine 9. The crude product residue is chromatographed on silica gel with... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccn2ccnc2c1 | HCl | CC(CC)=O | null | null | CC(C)(C)OC(=O)CCl.CC(C)(Cc1cnc2c(O)cccn12)[N+](=O)[O-]>CC(CC)=O>CC(C)(C)OC(=O)COc1cccn2c(CC(C)(C)[N+](=O)[O-])cnc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-80bda8328b14456289ce30674b88a158 | CCOC(=O)CBr.NC(=O)c1ncccc1O>>CCOC(=O)COc1cccnc1C(N)=O | OC=1C(=NC=CC1)C(=O)N.BrCC(=O)OCC.C([O-])([O-])=O.[K+].[K+]>>C(C)OC(=O)COC=1C(=NC=CC1)C(=O)N | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[OH:7][c:8]1[cH:9][cH:10][cH:11][n:12][c:13]1[C:14]([NH2:15])=[O:16]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][cH:11][n:12][c:13]1[C:14]([NH2:15])=[O:16] | CCOC(=O)CBr.NC(=O)c1ncccc1O | CCOC(=O)COc1cccnc1C(N)=O | null | null | CC(CC)=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | c1ccncc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[N;D1;H2:6]-[C:7](=[O;D1;H0:8])-[c:9](:[#7;a:10]:[c:11]):[c:12](-[OH;D1;+0:13]):[c:14]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:13]-[c:12](:[c:14]):[c:9](-[C:7](-[N;D1;H2:6])=[O;D1;H0:8]):[#7;a:10]:[c:11] | 53.3 | [{"value": 53.0, "product": "C(C)OC(=O)COC=1C(=NC=CC1)C(=O)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.3, "product": "C(C)OC(=O)COC=1C(=NC=CC1)C(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A mixture of 3-hydroxy picolinic amide (10 g, 72 mmol), ethyl bromoacetate (12.02 g, 72 mmol) and anhydrous potassium carbonate (10.9 g, 79.2 mmol) in 250 ml of dry 2-butanone is heated at 80° C. for 20 hours. After cooling, the inorganic salts are filtered off and the filtrate is reduced to approximately 120 ml. After... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccncc1 | HBr | CC(CC)=O | 80 | null | CCOC(=O)CBr.NC(=O)c1ncccc1O>CC(CC)=O>CCOC(=O)COc1cccnc1C(N)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2e813dd249f248748a13ef6c7ad764d3 | CCOC(=O)COc1cccnc1C(N)=O>>CCOC(=O)COc1cccnc1C#N | O.C(C)OC(=O)COC=1C(=NC=CC1)C(=O)N.C(C)N(CC)CC.FC(C(=O)OC(C(F)(F)F)=O)(F)F>>C(#N)C1=NC=CC=C1OCC(=O)OCC | O=[C:14]([c:13]1[c:8]([O:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:9][cH:10][cH:11][n:12]1)[NH2:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][cH:11][n:12][c:13]1[C:14]#[N:15] | CCOC(=O)COc1cccnc1C(N)=O | CCOC(=O)COc1cccnc1C#N | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 5094e9d814705bbdc421edbf7e9198e499e70e93916e2cec6eefbc82d1ba5440 | 32b9893bcb5223559a9d02852f8392cf6473aacfb044a52ba4e9cb9c29edb170 | c1ccncc1 | O=[C;H0;D3;+0:1](-[NH2;D1;+0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6]>>[N;H0;D1;+0:2]#[C;H0;D2;+0:1]-[c:3](:[c:4]):[#7;a:5]:[c:6] | 87 | [{"value": 87.0, "product": "C(#N)C1=NC=CC=C1OCC(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.0, "product": "C(#N)C1=NC=CC=C1OCC(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of 3-(ethoxycarbonylmethoxy)picolinamide (5.1 g, 22.8 mmol) and triethylamine (6.68 ml, 47.9 mmol) in 100 ml of dry methylene chloride is added trifluoroacetic anhydride (6.77 ml, 47.9 mmol), dropwise, at ambient temperature under argon. After stirring for 16 hours, 100 ml of water is added. The organic p... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide | Nitrile | null | null | c1ccncc1 | HO- | C(Cl)Cl | null | 16 | CCOC(=O)COc1cccnc1C(N)=O>C(Cl)Cl>CCOC(=O)COc1cccnc1C#N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a6b934e887f4440690f440b53aded42c | CCOC(=O)COc1cccnc1C#N>>CCOC(=O)COc1cccnc1CN.Cl | C(#N)C1=NC=CC=C1OCC(=O)OCC.Cl>>Cl.Cl.NCC1=NC=CC=C1OCC(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][cH:11][n:12][c:13]1[C:14]#[N:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][cH:11][n:12][c:13]1[CH2:14][NH2:15].[ClH:17] | CCOC(=O)COc1cccnc1C#N | CCOC(=O)COc1cccnc1CN.Cl | null | [Pd] | C(C)O | Functional Group Interconversion | Reduction of nitrile to amine | 3b047a13c16a607c445b1c419e256808e8c9a0097d8fb9efd4e7970deb782b70 | 2882e57127fc469aa16ca9a2fd53388b6d97c74c76c010e6eb01be5726f46aa5 | c1ccncc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[#7;a:5]:[c:6]>>[NH2;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[#7;a:5]:[c:6] | null | [] | null | null | 4 | HOUR | To a solution of 2-cyano-3-(ethoxycarbonylmethoxy)pyridine (3.2 g, 15.52 mmol) in 180 ml of ethanol is added concentrated aqueous HCl (2.92 ml, 35 mmol) and 10% palladium on charcoal (1.5 g). After stirring for 4 hours under a hydrogen pressure of 4 bar, the mixture is filtered through celite, rinsed with ethanol and e... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccncc1 | Other | [Pd].C(C)O | null | 4 | CCOC(=O)COc1cccnc1C#N>[Pd].C(C)O>CCOC(=O)COc1cccnc1CN.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3939a43cd5b74fe98e357b48d3d7224f | CC(C)(CC(=O)O)N1C(=O)c2ccccc2C1=O.CCOC(=O)COc1cccnc1CN>>CCOC(=O)COc1cccnc1CNC(=O)CC(C)(C)N1C(=O)c2ccccc2C1=O | Cl.Cl.NCC1=NC=CC=C1OCC(=O)OCC.C(C)N(CC)CC.CC(CC(=O)O)(N1C(C2=CC=CC=C2C1=O)=O)C>>C(C)OC(COC=1C(=NC=CC1)CNC(CC(C)(C)N1C(C2=CC=CC=C2C1=O)=O)=O)=O | O[C:16](=[O:17])[CH2:18][C:19]([CH3:20])([CH3:21])[N:22]1[C:23](=[O:24])[c:25]2[cH:26][cH:27][cH:28][cH:29][c:30]2[C:31]1=[O:32].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][cH:11][n:12][c:13]1[CH2:14][NH2:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][cH:11][n:12][c:13]1[CH2:14... | CC(C)(CC(=O)O)N1C(=O)c2ccccc2C1=O.CCOC(=O)COc1cccnc1CN | CCOC(=O)COc1cccnc1CNC(=O)CC(C)(C)N1C(=O)c2ccccc2C1=O | null | null | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CCN1C(=O)c2ccccc2C1=O)NCc1ccccn1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[#7;a:5]:[c:6]-[C:7]-[NH2;D1;+0:8]>>[#7;a:5]:[c:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | 62.4 | [{"value": 46.0, "product": "C(C)OC(COC=1C(=NC=CC1)CNC(CC(C)(C)N1C(C2=CC=CC=C2C1=O)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.4, "product": "C(C)OC(COC=1C(=NC=CC1)CNC(CC(C)(C)N1C(C2=CC=CC=C2C1=O)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a solution of 2-aminomethyl-3-(ethoxycarbonylmethoxy)pyridine dihydrochloride (610 mg, 2.155 mmol), triethylamine (732 μl, 5.258 mmol), N,N-dicyclohexylcarbodiimide (596 mg, 2.892 mmol) and 4-(N,N-diemethylamino)-pyridine (10 mg) in 6 ml of dry methylene chloride is added β,β-dimethyl-1,3-dioxo-2-isoindolinepropioni... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccc2c(c1)C[NH]C2 | HO- | C(Cl)Cl | null | 24 | CC(C)(CC(=O)O)N1C(=O)c2ccccc2C1=O.CCOC(=O)COc1cccnc1CN>C(Cl)Cl>CCOC(=O)COc1cccnc1CNC(=O)CC(C)(C)N1C(=O)c2ccccc2C1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6f01404cb7b24fc9949d146b5037c393 | CCOC(=O)COc1cccnc1CNC(=O)CC(C)(C)N1C(=O)c2ccccc2C1=O>>CCOC(=O)COc1cccn2c(CC(C)(C)N3C(=O)c4ccccc4C3=O)ncc12 | C(C)OC(COC=1C(=NC=CC1)CNC(CC(C)(C)N1C(C2=CC=CC=C2C1=O)=O)=O)=O>>C(C)OC(COC=1C=2N(C=CC1)C(=NC2)CC(C)(C)N2C(C1=CC=CC=C1C2=O)=O)=O | O=[C:13]([CH2:14][C:15]([CH3:16])([CH3:17])[N:18]1[C:19](=[O:20])[c:21]2[cH:22][cH:23][cH:24][cH:25][c:26]2[C:27]1=[O:28])[NH:29][CH2:30][c:31]1[c:8]([O:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:9][cH:10][cH:11][n:12]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][cH:11][n:12]2[c:13]([CH2:14][C:1... | CCOC(=O)COc1cccnc1CNC(=O)CC(C)(C)N1C(=O)c2ccccc2C1=O | CCOC(=O)COc1cccn2c(CC(C)(C)N3C(=O)c4ccccc4C3=O)ncc12 | null | null | P(=O)(Cl)(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | 1b4e55ff2e0f60e6a44cc161283eee0d751c452ef3ad342b3370f9f671cf0284 | 4c49decc0d3b49884847872e93a9c81862e00fd5fd04c96a796b9efc98b43f78 | O=C1c2ccccc2C(=O)N1CCc1ncc2ccccn12 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[NH;D2;+0:4]-[CH2;D2;+0:5]-[c:6](:[c:7]):[n;H0;D2;+0:8]:[c:9]:[c:10]>>[C:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:4]:[cH;D2;+0:5]:[c:6](:[c:7]):[n;H0;D3;+0:8]:1:[c:9]:[c:10] | 55.3 | [{"value": 55.0, "product": "C(C)OC(COC=1C=2N(C=CC1)C(=NC2)CC(C)(C)N2C(C1=CC=CC=C1C2=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.3, "product": "C(C)OC(COC=1C=2N(C=CC1)C(=NC2)CC(C)(C)N2C(C1=CC=CC=C1C2=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of (2-{[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-methyl-butyrylamino]-methyl}-pyridin-3-yloxy)-acetic acid ethyl ester (2.79 g, 6.349 mmol) in 100 ml of neat phosphoryl chloride is stirred at 75° C. for 16 hours. The reaction mixture is poured on 200 g of crushed ice and extracted with methylene chloride. T... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1ccncc1 | c1ccn2cncc2c1 | c1ccc2c(c1)C[NH]C2.c1ccn2cncc2c1 | HO- | P(=O)(Cl)(Cl)Cl | null | null | CCOC(=O)COc1cccnc1CNC(=O)CC(C)(C)N1C(=O)c2ccccc2C1=O>P(=O)(Cl)(Cl)Cl>CCOC(=O)COc1cccn2c(CC(C)(C)N3C(=O)c4ccccc4C3=O)ncc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8c16c567494f4b01a7047ef2e3c85e55 | CC(C)(Cc1cnc2c(Br)cccn12)[N+](=O)[O-].OB(O)c1ccsc1>>CC(C)(Cc1cnc2c(-c3ccsc3)cccn12)[N+](=O)[O-] | BrC=1C=2N(C=CC1)C(=CN2)CC(C)([N+](=O)[O-])C.S1C=C(C=C1)B(O)O>>CC(CC1=CN=C2N1C=CC=C2C2=CSC=C2)(C)[N+](=O)[O-] | Br[c:9]1[c:8]2[n:7][cH:6][c:5]([CH2:4][C:2]([CH3:1])([CH3:3])[N+:19](=[O:20])[O-:21])[n:18]2[cH:17][cH:16][cH:15]1.OB(O)[c:10]1[cH:11][cH:12][s:13][cH:14]1>>[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][n:7][c:8]2[c:9](-[c:10]3[cH:11][cH:12][s:13][cH:14]3)[cH:15][cH:16][cH:17][n:18]12)[N+:19](=[O:20])[O-:21] | CC(C)(Cc1cnc2c(Br)cccn12)[N+](=O)[O-].OB(O)c1ccsc1 | CC(C)(Cc1cnc2c(-c3ccsc3)cccn12)[N+](=O)[O-] | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 98571be3caf5ce9d306088c6a4547047cdefaf6f82db2deeccf45cb13a0ba90d | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1cc(-c2ccsc2)c2nccn2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]2:[c:6]:[c:7]:[#7;a:8]:[c:9]:2:1.O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[c:12]:[#16;a:13]:[c:14]:1>>[#16;a:13]1:[c:12]:[c:11]:[c;H0;D3;+0:10](-[c;H0;D3;+0:1]2:[c:2]:[c:3]:[c:4]:[#7;a:5]3:[c:6]:[c:7]:[#7;a:8]:[c:9]:3:2):[c:14]:1 | 75.3 | [{"value": 75.0, "product": "CC(CC1=CN=C2N1C=CC=C2C2=CSC=C2)(C)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.3, "product": "CC(CC1=CN=C2N1C=CC=C2C2=CSC=C2)(C)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 8-Bromo-3-(2-methyl-2-nitropropyl)imidazo[1,2-a]pyridine (1.0 g, 3.35 mmol) and thiophene-3-boronic acid (0.64 g, 5.0 mmol) are coupled as described in Amine 14 to give 760 mg of 3-(2-methyl-2-nitropropyl)-8-(3-thienyl)imidazo[1,2-a]pyridine (75%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccn2ccnc2c1.c1ccsc1 | c1ccsc1.c1ccn2ccnc2c1 | c1ccsc1.c1ccn2ccnc2c1 | HBr.B | null | null | null | CC(C)(Cc1cnc2c(Br)cccn12)[N+](=O)[O-].OB(O)c1ccsc1>>CC(C)(Cc1cnc2c(-c3ccsc3)cccn12)[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-db81d706c11d4565b429fd979c39895b | N#Cc1c(F)cccc1C(F)(F)F>>NCc1c(F)cccc1C(F)(F)F | FC1=C(C#N)C(=CC=C1)C(F)(F)F.CO>>FC1=C(CN)C(=CC=C1)C(F)(F)F | [N:1]#[C:2][c:3]1[c:4]([F:5])[cH:6][cH:7][cH:8][c:9]1[C:10]([F:11])([F:12])[F:13]>>[NH2:1][CH2:2][c:3]1[c:4]([F:5])[cH:6][cH:7][cH:8][c:9]1[C:10]([F:11])([F:12])[F:13] | N#Cc1c(F)cccc1C(F)(F)F | NCc1c(F)cccc1C(F)(F)F | null | null | C1CCOC1 | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1ccccc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[NH2;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 100 | [{"value": 100.0, "product": "FC1=C(CN)C(=CC=C1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To 2-fluoro-6-(trifluoromethyl)benzonitrile (45 g, 0.238 mmol) in 60 mL of THF was added 1 M BH3:THF slowly at 60° C. and the resulting solution was refluxed overnight. The reaction mixture was cooled to ambient temperature. Methanol (420 mL) was added slowly and stirred well. The solvents were then evaporated and the ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccccc1 | null | C1CCOC1 | null | null | N#Cc1c(F)cccc1C(F)(F)F>C1CCOC1>NCc1c(F)cccc1C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6a7613df95dd4595b711299075248dce | NC(N)=O.NCc1c(F)cccc1C(F)(F)F>>NC(=O)NCc1c(F)cccc1C(F)(F)F | FC1=C(CN)C(=CC=C1)C(F)(F)F.NC(=O)N.Cl>>FC1=C(CNC(=O)N)C(=CC=C1)C(F)(F)F | N[C:2]([NH2:1])=[O:3].[NH2:4][CH2:5][c:6]1[c:7]([F:8])[cH:9][cH:10][cH:11][c:12]1[C:13]([F:14])([F:15])[F:16]>>[NH2:1][C:2](=[O:3])[NH:4][CH2:5][c:6]1[c:7]([F:8])[cH:9][cH:10][cH:11][c:12]1[C:13]([F:14])([F:15])[F:16] | NC(N)=O.NCc1c(F)cccc1C(F)(F)F | NC(=O)NCc1c(F)cccc1C(F)(F)F | null | null | O | Acylation | OtherReaction | 9d7857c9b3bddcd4c0ac6bc01765ead2139eaedad346ca9a5a937527052e232c | f17cc9fc6250903fc236407915f5767fca8f6b6242f886ce02918cf1cdfcba61 | c1ccccc1 | N-[C;H0;D3;+0:1](-[N;D1;H2:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[C:5]-[c:6]>>[N;D1;H2:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[C:5]-[c:6] | 73.4 | [{"value": 73.4, "product": "FC1=C(CNC(=O)N)C(=CC=C1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To 2-fluoro-6-(trifluoromethyl)benzylamine 1a (51.5 g, 0.267 mmol) in a flask, urea (64 g, 1.07 mmol), HCl (conc., 30.9 mmol, 0.374 mmol) and water (111 mL) were added. The mixture was refluxed for 6 hours. The mixture was cooled to ambient temperature, further cooled with ice and filtered to give a yellow solid. Recry... | 10.6084/m9.figshare.5104873.v1 | null | Urea.Primary amine | Urea | null | null | c1ccccc1 | Other | O | null | null | NC(N)=O.NCc1c(F)cccc1C(F)(F)F>O>NC(=O)NCc1c(F)cccc1C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-74069b269ece4b8c8db83c631d4d7373 | C=C1CC(=O)O1.NC(=O)NCc1c(F)cccc1C(F)(F)F>>Cc1cc(=O)[nH]c(=O)n1Cc1c(F)cccc1C(F)(F)F | C[Si](C)(C)Cl.[Na+].[I-].FC1=C(CNC(=O)N)C(=CC=C1)C(F)(F)F.C=C1CC(=O)O1>>FC1=C(CN2C(NC(C=C2C)=O)=O)C(=CC=C1)C(F)(F)F | O=[C:4]1[CH2:3][C:2](=[CH2:1])[O:5]1.[NH2:6][C:7](=[O:8])[NH:9][CH2:10][c:11]1[c:12]([F:13])[cH:14][cH:15][cH:16][c:17]1[C:18]([F:19])([F:20])[F:21]>>[CH3:1][c:2]1[cH:3][c:4](=[O:5])[nH:6][c:7](=[O:8])[n:9]1[CH2:10][c:11]1[c:12]([F:13])[cH:14][cH:15][cH:16][c:17]1[C:18]([F:19])([F:20])[F:21] | C=C1CC(=O)O1.NC(=O)NCc1c(F)cccc1C(F)(F)F | Cc1cc(=O)[nH]c(=O)n1Cc1c(F)cccc1C(F)(F)F | null | null | C(C)#N.O | Aromatic Heterocycle Formation | OtherReaction | a37b4c067465a691de5daff933eba83859c885cdd9721e239da81187bbe8dd27 | 23e257277262bff07eb8ec8d45f177fa3c8e4928c2a9deb75e737ba0a574bffd | O=c1ccn(Cc2ccccc2)c(=O)[nH]1 | O=[C;H0;D3;+0:1]1-[CH2;D2;+0:2]-[C;H0;D3;+0:3](=[CH2;D1;+0:4])-[O;H0;D2;+0:5]-1.[NH2;D1;+0:6]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[NH;D2;+0:9]-[C:10]-[c:11]>>[CH3;D1;+0:4]-[c;H0;D3;+0:3]1:[cH;D2;+0:2]:[c;H0;D3;+0:1](=[O;H0;D1;+0:5]):[nH;D2;+0:6]:[c;H0;D3;+0:7](=[O;D1;H0:8]):[n;H0;D3;+0:9]:1-[C:10]-[c:11] | 81.6 | [{"value": 81.6, "product": "FC1=C(CN2C(NC(C=C2C)=O)=O)C(=CC=C1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | NaI (43.9 g, 293 mmol) was added to N-[2-fluoro-6-(trifluoromethyl)benzyl]urea 1b (46.2 g, 19.6 mmol) in 365 mL of acetonitrile. The resulting mixture was cooled in an ice-water bath. Diketene (22.5 mL, 293 mmol) was added slowly via dropping funnel followed by addition of TMSCl (37.2 mL, 293 mmol) in the same manner. ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Urea.Vinyl | null | C1COC1 | c1ccncn1 | c1ccncn1.c1ccccc1 | HO- | C(C)#N.O | null | 20 | C=C1CC(=O)O1.NC(=O)NCc1c(F)cccc1C(F)(F)F>C(C)#N.O>Cc1cc(=O)[nH]c(=O)n1Cc1c(F)cccc1C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d244025cf2d34fc8a1422afae2a51a92 | BrBr.Cc1cc(=O)[nH]c(=O)n1Cc1c(F)cccc1C(F)(F)F>>Cc1c(Br)c(=O)[nH]c(=O)n1Cc1c(F)cccc1C(F)(F)F | BrBr.FC1=C(CN2C(NC(C=C2C)=O)=O)C(=CC=C1)C(F)(F)F>>BrC=1C(NC(N(C1C)CC1=C(C=CC=C1C(F)(F)F)F)=O)=O | Br[Br:4].[CH3:1][c:2]1[cH:3][c:5](=[O:6])[nH:7][c:8](=[O:9])[n:10]1[CH2:11][c:12]1[c:13]([F:14])[cH:15][cH:16][cH:17][c:18]1[C:19]([F:20])([F:21])[F:22]>>[CH3:1][c:2]1[c:3]([Br:4])[c:5](=[O:6])[nH:7][c:8](=[O:9])[n:10]1[CH2:11][c:12]1[c:13]([F:14])[cH:15][cH:16][cH:17][c:18]1[C:19]([F:20])([F:21])[F:22] | BrBr.Cc1cc(=O)[nH]c(=O)n1Cc1c(F)cccc1C(F)(F)F | Cc1c(Br)c(=O)[nH]c(=O)n1Cc1c(F)cccc1C(F)(F)F | null | null | C(C)(=O)O | Functional Group Interconversion | Bromination | ab990d4cf4e29f4bfc1eed19f85a157586116cba28cf7e047e67e704b97886a0 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | O=c1ccn(Cc2ccccc2)c(=O)[nH]1 | Br-[Br;H0;D1;+0:1].[C:2]-[#7;a:3]1:[c:4]:[#7;a:5]:[c:6](=[O;D1;H0:7]):[cH;D2;+0:8]:[c:9]:1-[C;D1;H3:10]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:8]1:[c:9](-[C;D1;H3:10]):[#7;a:3](-[C:2]):[c:4]:[#7;a:5]:[c:6]:1=[O;D1;H0:7] | 48,750 | [{"value": 48750.0, "product": "BrC=1C(NC(N(C1C)CC1=C(C=CC=C1C(F)(F)F)F)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Bromine (16.5 mL, 0.32 mmol) was added to 1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-methylpyrimidine-2,4(1H,3H)-dione 1c (48.5 g, 0.16 mol) in 145 mL of acetic acid. The resulting mixture became clear then formed precipitate within an hour. After 2 hours stirring, the yellow solid was filtered and washed with cold EtOAc... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccncn1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HBr | C(C)(=O)O | null | 2 | BrBr.Cc1cc(=O)[nH]c(=O)n1Cc1c(F)cccc1C(F)(F)F>C(C)(=O)O>Cc1c(Br)c(=O)[nH]c(=O)n1Cc1c(F)cccc1C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3e4b73e3d39440cc833debd0e62e047a | CC(C)(C)OC(=O)N(CC(=O)O)C1CCCCC1>>CC(C)(C)OC(=O)NC(CO)C1CCCCC1 | C(C)(C)(C)OC(=O)N(CC(=O)O)C1CCCCC1.C1CCOC1.B>>C1(CCCCC1)C(CO)NC(OC(C)(C)C)=O | O=[C:10]([CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1)[OH:11]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH:9]([CH2:10][OH:11])[CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1 | CC(C)(C)OC(=O)N(CC(=O)O)C1CCCCC1 | CC(C)(C)OC(=O)NC(CO)C1CCCCC1 | null | null | null | Miscellaneous | OtherReaction | 81b1cc2474e7a3ba521fe5299a00cbd9466a43710bae077d604fc565dcf6c109 | ae762b4e65c73a5c2a348ecd04125fb44b0b1da49de4a210a4398f3eba74b8a1 | C1CCCCC1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[CH2;D2;+0:3]-[N;H0;D3;+0:4](-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11])-[CH;D3;+0:12](-[C:13]-[C:14])-[C:15]-[C:16]>>[C:14]-[C:13]-[CH;D3;+0:12](-[CH;D3;+0:3](-[CH2;D2;+0:1]-[O;D1;H1:2])-[NH;D2;+0:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H... | 66.7 | [{"value": 66.7, "product": "C1(CCCCC1)C(CO)NC(OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of N-(t-butyloxycarbonyl)cyclohexylglycine (2.0 g, 7.77 mmol) in anhydrous THF (10 mL) was cooled to 0° C. Borane solution (1 M in THF, 15.5 mL, 15.5 mmol) was added slowly and the reaction mixture was warmed to room temperature and stirred for 2 hours. The reaction was quenched with MeOH (5 mL), volatiles w... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid | Carbamic ester.Primary alcohol | C1CCCCC1 | C1CCCCC1 | C1CCCCC1 | Other | null | null | 2 | CC(C)(C)OC(=O)N(CC(=O)O)C1CCCCC1>>CC(C)(C)OC(=O)NC(CO)C1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4537ae6cd773424db4990e693acd9612 | CC(C)(C)OC(=O)NC(CO)C1CCCCC1.Cc1c(Br)c(=O)[nH]c(=O)n1Cc1c(F)cccc1F>>Cc1c(Br)c(=O)n(C[C@H](NC(=O)OC(C)(C)C)C2CCCCC2)c(=O)n1Cc1c(F)cccc1F | CC(C)(C)OC(=O)/N=N/C(=O)OC(C)(C)C.C1(CCCCC1)C(CO)NC(OC(C)(C)C)=O.BrC=1C(NC(N(C1C)CC1=C(C=CC=C1F)F)=O)=O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>BrC=1C(N(C(N(C1C)CC1=C(C=CC=C1F)F)=O)C[C@@H](C1CCCCC1)NC(=O)OC(C)(C)C)=O | O[CH2:8][CH:9]([NH:10][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1.[CH3:1][c:2]1[c:3]([Br:4])[c:5](=[O:6])[nH:7][c:24](=[O:25])[n:26]1[CH2:27][c:28]1[c:29]([F:30])[cH:31][cH:32][cH:33][c:34]1[F:35]>>[CH3:1][c:2]1[c:3]([Br:4])[c:5](=[O:6])[n:7]([CH2:8][C@H:9](... | CC(C)(C)OC(=O)NC(CO)C1CCCCC1.Cc1c(Br)c(=O)[nH]c(=O)n1Cc1c(F)cccc1F | Cc1c(Br)c(=O)n(C[C@H](NC(=O)OC(C)(C)C)C2CCCCC2)c(=O)n1Cc1c(F)cccc1F | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 2f40266554459f7093e96d8b9a4eb131b8558bf4738ef351194baeaeb2cc0f39 | 2ab4024aa17b6e89368e6fe8ee731d32c7611cb9b23de403e301e8362fea90b1 | O=c1ccn(Cc2ccccc2)c(=O)n1CCC1CCCCC1 | O-[CH2;D2;+0:1]-[CH;D3;+0:2](-[#7:3]-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C;D1;H3:10])-[C:11](-[C:12])-[C:13].[C:14]-[#7;a:15]1:[c:16]:[c:17]:[c:18](=[O;D1;H0:19]):[nH;D2;+0:20]:[c:21]:1=[O;D1;H0:22]>>[C:12]-[C:11](-[C@@H;D3;+0:2](-[#7:3]-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3... | 95.4 | [{"value": 95.4, "product": "BrC=1C(N(C(N(C1C)CC1=C(C=CC=C1F)F)=O)C[C@@H](C1CCCCC1)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.3, "product": "BrC=1C(N(C(N(C1C)CC1=C(C=CC=C1F)F)=O)C[C@@H](C1CCCCC1)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A solution of tert-butyl 1-cyclohexyl-2-hydroxyethylcarbamate 4a (638 mg, 2.62 mmol) in THF (10 mL) was treated with 5-bromo-1-(2,6-difluorobenzyl)-6-methylpyrimidine-2,4(1H,3H)-dione 1d.1 (869 mg, 2.62 mmol) and triphenylphosphine (1.03 g, 3.93 mmol) at ambient temperature, then di-tert-butylazodicarboxylate (906 mg, ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | null | c1cncnc1 | c1cncnc1 | c1cncnc1.C1CCCCC1.c1ccccc1 | HO- | C1CCOC1 | null | 16 | CC(C)(C)OC(=O)NC(CO)C1CCCCC1.Cc1c(Br)c(=O)[nH]c(=O)n1Cc1c(F)cccc1F>C1CCOC1>Cc1c(Br)c(=O)n(C[C@H](NC(=O)OC(C)(C)C)C2CCCCC2)c(=O)n1Cc1c(F)cccc1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-098da2c7c3eb4b4790da916e01a64625 | COc1cccc(B(O)O)c1F.Cc1c(Br)c(=O)n(C[C@H](NC(=O)OC(C)(C)C)C2CCCCC2)c(=O)n1Cc1c(F)cccc1F>>COc1cccc(-c2c(C)n(Cc3c(F)cccc3F)c(=O)n(C[C@H](NC(=O)OC(C)(C)C)C3CCCCC3)c2=O)c1F | BrC=1C(N(C(N(C1C)CC1=C(C=CC=C1F)F)=O)C[C@@H](C1CCCCC1)NC(=O)OC(C)(C)C)=O.FC1=C(C=CC=C1OC)B(O)O>>C(C)(C)(C)OC(=O)N[C@@H](CN1C(N(C(=C(C1=O)C1=C(C(=CC=C1)OC)F)C)CC1=C(C=CC=C1F)F)=O)C1CCCCC1 | OB(O)[c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[c:42]1[F:43].Br[c:8]1[c:9]([CH3:10])[n:11]([CH2:12][c:13]2[c:14]([F:15])[cH:16][cH:17][cH:18][c:19]2[F:20])[c:21](=[O:22])[n:23]([CH2:24][C@H:25]([NH:26][C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33])[CH:34]2[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]2)[c:40]1=[O:4... | COc1cccc(B(O)O)c1F.Cc1c(Br)c(=O)n(C[C@H](NC(=O)OC(C)(C)C)C2CCCCC2)c(=O)n1Cc1c(F)cccc1F | COc1cccc(-c2c(C)n(Cc3c(F)cccc3F)c(=O)n(C[C@H](NC(=O)OC(C)(C)C)C3CCCCC3)c2=O)c1F | null | null | CCO.COCCOC | C-C Coupling | Suzuki | 5efc69cb0f56c6c241a71b9df28c03b094ed8fc2f31567997f12f88c03083478 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=c1c(-c2ccccc2)cn(Cc2ccccc2)c(=O)n1CCC1CCCCC1 | Br-[c;H0;D3;+0:1]1:[c:2](=[O;D1;H0:3]):[#7;a:4](-[C:5]):[c:6]:[#7;a:7](-[C:8]):[c:9]:1-[C;D1;H3:10].O-B(-O)-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14](-[F;D1;H0:15]):[c:16]>>[C:8]-[#7;a:7]1:[c:6]:[#7;a:4](-[C:5]):[c:2](=[O;D1;H0:3]):[c;H0;D3;+0:1](-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14](-[F;D1;H0:15]):[c:16]):[c:9]:1-[C;D1... | 32.3 | [{"value": 32.3, "product": "C(C)(C)(C)OC(=O)N[C@@H](CN1C(N(C(=C(C1=O)C1=C(C(=CC=C1)OC)F)C)CC1=C(C=CC=C1F)F)=O)C1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.3, "product": "C(C)(C)(C)OC(=O)N[C@@H](CN1C(N(C(=C(C1=O)C1=C(C(=CC=C1)OC)F)C)CC1=C(C=CC=C1F)F)=O)C1CCCCC1", "details": "CALCULATEDPERCEN... | 80 | CELSIUS | null | null | 5-Bromo-3-[2(R)-tert-butoxycarbonylamino-2-cyclohexylethyl]-1-[2,6-difluorobenzyl]-6-methyl-pyrimidine-2,4(1H,3H)-dione 2b (1.0 g, 1.79 mmol) in bezene/EtOH/ethylene glycol dimethyl ether (20/2/22 mL) was added 2-fluoro-3-methoxyphenylboronic acid (382 mg, 2.24 mmol) and saturated Ba(OH)2/water (˜0.5 M, 15 mL). The rea... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1cncnc1 | c1ccccc1.c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1.C1CCCCC1 | HBr.B | CCO.COCCOC | 80 | null | COc1cccc(B(O)O)c1F.Cc1c(Br)c(=O)n(C[C@H](NC(=O)OC(C)(C)C)C2CCCCC2)c(=O)n1Cc1c(F)cccc1F>CCO.COCCOC>COc1cccc(-c2c(C)n(Cc3c(F)cccc3F)c(=O)n(C[C@H](NC(=O)OC(C)(C)C)C3CCCCC3)c2=O)c1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bf870742348e4e4e9eb9a1691d7df7e7 | COc1cccc(-c2c(C)n(Cc3c(F)cccc3F)c(=O)n(C[C@H](NC(=O)OC(C)(C)C)C3CCCCC3)c2=O)c1F>>COc1cccc(-c2c(C)n(Cc3c(F)cccc3F)c(=O)n(C[C@H](N)C3CCCCC3)c2=O)c1F | C(C)(C)(C)OC(=O)N[C@@H](CN1C(N(C(=C(C1=O)C1=C(C(=CC=C1)OC)F)C)CC1=C(C=CC=C1F)F)=O)C1CCCCC1.C(=O)(C(F)(F)F)O>>N[C@@H](CN1C(N(C(=C(C1=O)C1=C(C(=CC=C1)OC)F)C)CC1=C(C=CC=C1F)F)=O)C1CCCCC1 | CC(C)(C)OC(=O)[NH:26][C@@H:25]([CH2:24][n:23]1[c:21](=[O:22])[n:11]([CH2:12][c:13]2[c:14]([F:15])[cH:16][cH:17][cH:18][c:19]2[F:20])[c:9]([CH3:10])[c:8](-[c:7]2[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[c:35]2[F:36])[c:33]1=[O:34])[CH:27]1[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-... | COc1cccc(-c2c(C)n(Cc3c(F)cccc3F)c(=O)n(C[C@H](NC(=O)OC(C)(C)C)C3CCCCC3)c2=O)c1F | COc1cccc(-c2c(C)n(Cc3c(F)cccc3F)c(=O)n(C[C@H](N)C3CCCCC3)c2=O)c1F | null | null | ClCCl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=c1c(-c2ccccc2)cn(Cc2ccccc2)c(=O)n1CCC1CCCCC1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[C:4])-[NH2;D1;+0:1] | null | [] | null | null | 1 | HOUR | To compound 2c (300 mg, 0.5 mmol) in dichloromethane (DCM, 2 mL) was added TFA (2 mL) and the reaction mixture was stirred at ambient temperature for 1 hour. Volatiles were evaporated and the residue was partitioned between saturated NaHCO3/water and EtOAc. The organic layer was dried (sodium sulfate), evaporated, puri... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1cncnc1.c1ccccc1.C1CCCCC1 | HO- | ClCCl | null | 1 | COc1cccc(-c2c(C)n(Cc3c(F)cccc3F)c(=O)n(C[C@H](NC(=O)OC(C)(C)C)C3CCCCC3)c2=O)c1F>ClCCl>COc1cccc(-c2c(C)n(Cc3c(F)cccc3F)c(=O)n(C[C@H](N)C3CCCCC3)c2=O)c1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a482acab33484ab3b0f4276693cef233 | CC(C)(C)OCl.O=Cc1cccc(O)c1>>O=Cc1cccc(O)c1Cl | OC=1C=C(C=O)C=CC1.C(C)(C)(C)OCl>>ClC1=C(C=O)C=CC=C1O | CC(C)(C)O[Cl:10].[O:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][c:7]([OH:8])[cH:9]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][c:7]([OH:8])[c:9]1[Cl:10] | CC(C)(C)OCl.O=Cc1cccc(O)c1 | O=Cc1cccc(O)c1Cl | null | null | CC(=O)O | Functional Group Interconversion | Chlorination | f6effe61353895b318215d8bd9b6bb1105cafbf7be8c217d748df587260b32c3 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccccc1 | C-C(-C)(-C)-O-[Cl;H0;D1;+0:1].[O;D1;H0:2]=[C:3]-[c:4](:[c:5]):[cH;D2;+0:6]:[c:7](-[O;D1;H1:8]):[c:9]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:6](:[c:4](-[C:3]=[O;D1;H0:2]):[c:5]):[c:7](-[O;D1;H1:8]):[c:9] | 55 | [{"value": 55.0, "product": "ClC1=C(C=O)C=CC=C1O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.0, "product": "ClC1=C(C=O)C=CC=C1O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 3-hydroxybenzaldehyde (20.12 g, 160 mmol) in HOAc (40 mL) was added carefully tBuOCl (20 mL, 176 mmol) with stirring. The reaction became a clear solution and strongly exothermic. It was allowed to cool and stirred for 16 hours, resulting in a white precipitate. The solid was filtered, washed with H2... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | CC(=O)O | null | null | CC(C)(C)OCl.O=Cc1cccc(O)c1>CC(=O)O>O=Cc1cccc(O)c1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b9cc9e9f66774e30af6bf5dc8409bbea | O=Cc1cccc(O)c1Cl>>COc1cccc(C=O)c1Cl | ClC1=C(C=O)C=CC=C1O.C(=O)([O-])[O-].[K+].[K+]>>ClC1=C(C=O)C=CC=C1OC | [OH:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH:8]=[O:9])[c:10]1[Cl:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH:8]=[O:9])[c:10]1[Cl:11] | O=Cc1cccc(O)c1Cl | COc1cccc(C=O)c1Cl | null | null | CN(C)C=O | Miscellaneous | OtherReaction | 5b3aadc337038ce4d56616083181fcdb7df90626e7a012c21497c4b51b07950e | b3459c109bd254a21bc857ecee1ac83a8b4bf01bca8b217fb3b07e012c0f1c4b | c1ccccc1 | [OH;D1;+0:1]-[c:2](:[c:3]):[c:4]>>[C;D1;H3:5]-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 16 | HOUR | To a solution of 2-chloro-3-hydroxybenzaldehyde (4.55 g, 29 mmol) in DMF (30 mL) was added K2CO3 (4.8 g, 34.9 mmol) followed by Mel (2.7 mL, 43.6 mmol), and the mixture was stirred at room temperature for 16 hours. Following concentration in vacuo, the residual was taken up in ethyl acetate, washed with H2O, brine, dri... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether | null | null | c1ccccc1 | Other | CN(C)C=O | null | 16 | O=Cc1cccc(O)c1Cl>CN(C)C=O>COc1cccc(C=O)c1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-94e6d58d021842a393e3e834b1a45dc8 | COc1cccc(C=O)c1Cl.CSCS(C)=O>>COc1cccc(C=C(SC)S(C)=O)c1Cl | ClC1=C(C=O)C=CC=C1OC.CSCS(=O)C>>ClC1=C(C=CC=C1C=C(S(=O)C)SC)OC | O=[CH:8][c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[c:15]1[Cl:16].[CH2:9]([S:10][CH3:11])[S:12]([CH3:13])=[O:14]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH:8]=[C:9]([S:10][CH3:11])[S:12]([CH3:13])=[O:14])[c:15]1[Cl:16] | COc1cccc(C=O)c1Cl.CSCS(C)=O | COc1cccc(C=C(SC)S(C)=O)c1Cl | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 997b81c8ca22c39d094c9841658bc8d05053f6267c584426677ff3b86fcd9070 | d1104e4dc387c28c5ac408eab23aa043e968d3cfd16e99022454bf87ce31f401 | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[#16:6]-[CH2;D2;+0:7]-[#16:8](-[C;D1;H3:9])=[O;D1;H0:10]>>[C;D1;H3:5]-[#16:6]-[C;H0;D3;+0:7](=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[#16:8](-[C;D1;H3:9])=[O;D1;H0:10] | 48 | [{"value": 48.0, "product": "ClC1=C(C=CC=C1C=C(S(=O)C)SC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.8, "product": "ClC1=C(C=CC=C1C=C(S(=O)C)SC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2-chloro-3-methoxybenzaldehyde 3a (4.65 g, 27.3 mmol) and methyl (methylthio)methyl sulfoxide (4.3 mL, 43.9 mmol) in THF (25 mL) was added a 40% methanolic solution of Triton B (6.2 mL, 13.6 mmol) and the resulting solution was refluxed for 16 hours. After THF was removed, the residue was taken up in e... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Monosulfide | Monosulfide | null | null | c1ccccc1 | HO- | C1CCOC1 | null | null | COc1cccc(C=O)c1Cl.CSCS(C)=O>C1CCOC1>COc1cccc(C=C(SC)S(C)=O)c1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9d3e899e3cf64f6d8d94d79526d70807 | CCOC(=O)C(=CN(C)C)c1cccc(OC)c1Cl.NC(N)=O>>COc1cccc(-c2c[nH]c(=O)[nH]c2=O)c1Cl | C[Si](C)(C)Cl.ClC1=C(C=CC=C1OC)C(C(=O)OCC)=CN(C)C.NC(=O)N.[Na+].[I-].[OH-].[Na+]>>ClC1=C(C=CC=C1OC)C=1C(NC(NC1)=O)=O | CCO[C:14]([C:8]([c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[c:16]1[Cl:17])=[CH:9]N(C)C)=[O:15].[NH2:10][C:11](=[O:12])[NH2:13]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][nH:10][c:11](=[O:12])[nH:13][c:14]2=[O:15])[c:16]1[Cl:17] | CCOC(=O)C(=CN(C)C)c1cccc(OC)c1Cl.NC(N)=O | COc1cccc(-c2c[nH]c(=O)[nH]c2=O)c1Cl | null | null | C(C)#N | Aromatic Heterocycle Formation | OtherReaction | 92e0d68695f590d4a987df760ae9d0802a298c970bfa74a14cfbbf9f59bb90a0 | be0672f4c6fa3a26873eedbca7e989e373bb98a10936bd60225985378dadff3e | O=c1[nH]cc(-c2ccccc2)c(=O)[nH]1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](=[CH;D2;+0:4]-N(-C)-C)-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8](-[Cl;D1;H0:9]):[c:10].[NH2;D1;+0:11]-[C;H0;D3;+0:12](-[NH2;D1;+0:13])=[O;D1;H0:14]>>[Cl;D1;H0:9]-[c:8](:[c:10]):[c;H0;D3;+0:5](-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[nH;D2;+0:11]:[c;H0;D3;+0:12](=[O;D1;H0:14]):[nH;D2;+0:... | 82 | [{"value": 82.0, "product": "ClC1=C(C=CC=C1OC)C=1C(NC(NC1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.8, "product": "ClC1=C(C=CC=C1OC)C=1C(NC(NC1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of ethyl 2-(2-chloro-3-methoxyphenyl)-3-(dimethylamino)acrylate 3d (1.7 g, 6 mmol), urea (1.08 g, 18 mmol) and NaI (2.7 g, 18 mmol) in acetonitrile (20 mL) was added TMSCl (2.3 mL, 18 mmol). The resulting mixture was refluxed for 16 hours, cooled to room temperature, and 1.0 M NaOH (30 mL) was added. The r... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ester.Urea | null | null | c1cncnc1 | c1ccccc1.c1cncnc1 | HO- | C(C)#N | null | null | CCOC(=O)C(=CN(C)C)c1cccc(OC)c1Cl.NC(N)=O>C(C)#N>COc1cccc(-c2c[nH]c(=O)[nH]c2=O)c1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-db3ac4cd835c4a7ba8019567c9b9395c | COc1cccc(-c2cn(Cc3c(F)cccc3C(F)(F)F)c(=O)n(C[C@H](NC(=O)OC(C)(C)C)c3ccccc3)c2=O)c1Cl>>COc1cccc(-c2cn(Cc3c(F)cccc3C(F)(F)F)c(=O)n(C[C@H](N)c3ccccc3)c2=O)c1Cl | C(C)(C)(C)OC(=O)N[C@@H](CN1C(N(C=C(C1=O)C1=C(C(=CC=C1)OC)Cl)CC1=C(C=CC=C1C(F)(F)F)F)=O)C1=CC=CC=C1.C(=O)(C(F)(F)F)O>>N[C@@H](CN1C(N(C=C(C1=O)C1=C(C(=CC=C1)OC)Cl)CC1=C(C=CC=C1C(F)(F)F)F)=O)C1=CC=CC=C1 | CC(C)(C)OC(=O)[NH:28][C@@H:27]([CH2:26][n:25]1[c:23](=[O:24])[n:10]([CH2:11][c:12]2[c:13]([F:14])[cH:15][cH:16][cH:17][c:18]2[C:19]([F:20])([F:21])[F:22])[cH:9][c:8](-[c:7]2[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[c:37]2[Cl:38])[c:35]1=[O:36])[c:29]1[cH:30][cH:31][cH:32][cH:33][cH:34]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6... | COc1cccc(-c2cn(Cc3c(F)cccc3C(F)(F)F)c(=O)n(C[C@H](NC(=O)OC(C)(C)C)c3ccccc3)c2=O)c1Cl | COc1cccc(-c2cn(Cc3c(F)cccc3C(F)(F)F)c(=O)n(C[C@H](N)c3ccccc3)c2=O)c1Cl | null | null | ClCCl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=c1c(-c2ccccc2)cn(Cc2ccccc2)c(=O)n1CCc1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[c:4]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[c:4] | 96 | [{"value": 96.0, "product": "N[C@@H](CN1C(N(C=C(C1=O)C1=C(C(=CC=C1)OC)Cl)CC1=C(C=CC=C1C(F)(F)F)F)=O)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.6, "product": "N[C@@H](CN1C(N(C=C(C1=O)C1=C(C(=CC=C1)OC)Cl)CC1=C(C=CC=C1C(F)(F)F)F)=O)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_des... | null | null | 4.5 | HOUR | Compound 3g (2.7 g, 4.2 mmol) was dissolved in dichloromethane (10 mL), TFA (14 mL, 175 mmol) was added, and the mixture was stirred at room temperature for 4.5 hours. After concentration, the residue was taken up in DCM and saturated aq. NaHCO3 was added. The aq. layer was extracted with DCM. Combined organic extracts... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1cncnc1.c1ccccc1.c1ccccc1 | HO- | ClCCl | null | 4.5 | COc1cccc(-c2cn(Cc3c(F)cccc3C(F)(F)F)c(=O)n(C[C@H](NC(=O)OC(C)(C)C)c3ccccc3)c2=O)c1Cl>ClCCl>COc1cccc(-c2cn(Cc3c(F)cccc3C(F)(F)F)c(=O)n(C[C@H](N)c3ccccc3)c2=O)c1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e514aff2d8b1469695f26b9afac7cfd3 | COc1cccc(-c2cn(Cc3c(F)cccc3C(F)(F)F)c(=O)n(C[C@@H](CC(C)C)NC(=O)OC(C)(C)C)c2=O)c1Cl>>COc1cccc(-c2cn(Cc3c(F)cccc3C(F)(F)F)c(=O)n(C[C@H](N)CC(C)C)c2=O)c1Cl | C(C)(C)(C)OC(=O)N[C@@H](CN1C(N(C=C(C1=O)C1=C(C(=CC=C1)OC)Cl)CC1=C(C=CC=C1C(F)(F)F)F)=O)CC(C)C.C(=O)(C(F)(F)F)O>>N[C@@H](CN1C(N(C=C(C1=O)C1=C(C(=CC=C1)OC)Cl)CC1=C(C=CC=C1C(F)(F)F)F)=O)CC(C)C | CC(C)(C)OC(=O)[NH:28][C@@H:27]([CH2:26][n:25]1[c:23](=[O:24])[n:10]([CH2:11][c:12]2[c:13]([F:14])[cH:15][cH:16][cH:17][c:18]2[C:19]([F:20])([F:21])[F:22])[cH:9][c:8](-[c:7]2[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[c:35]2[Cl:36])[c:33]1=[O:34])[CH2:29][CH:30]([CH3:31])[CH3:32]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c... | COc1cccc(-c2cn(Cc3c(F)cccc3C(F)(F)F)c(=O)n(C[C@@H](CC(C)C)NC(=O)OC(C)(C)C)c2=O)c1Cl | COc1cccc(-c2cn(Cc3c(F)cccc3C(F)(F)F)c(=O)n(C[C@H](N)CC(C)C)c2=O)c1Cl | null | null | C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=c1[nH]c(=O)n(Cc2ccccc2)cc1-c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[C:4])-[NH2;D1;+0:1] | null | [] | null | null | 1.5 | HOUR | To a solution of compound 4a (30 mg, 0.048 mmol) in DCM (1 mL) was added TFA (0.1 mL, 1.3 mmol) and stirred at room temperature for 1.5 hours. After concentration, the residue was taken up in DCM and saturated aq. NaHCO3 was added. The aq. layer was extracted with DCM. Combined organic extracts were dried over Na2SO4 a... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1cncnc1.c1ccccc1 | HO- | C(Cl)Cl | null | 1.5 | COc1cccc(-c2cn(Cc3c(F)cccc3C(F)(F)F)c(=O)n(C[C@@H](CC(C)C)NC(=O)OC(C)(C)C)c2=O)c1Cl>C(Cl)Cl>COc1cccc(-c2cn(Cc3c(F)cccc3C(F)(F)F)c(=O)n(C[C@H](N)CC(C)C)c2=O)c1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-15ae9e18618349a29400f088b19cbcc8 | COc1cccc(-c2c(C)n(Cc3c(F)cccc3F)c(=O)n(C[C@H](NC(=O)OC(C)(C)C)c3ccccc3)c2=O)c1F.C[S-]>>COc1cccc(-c2c(C)n(Cc3c(F)cccc3SC)c(=O)n(C[C@H](NC(=O)OC(C)(C)C)c3ccccc3)c2=O)c1F | C[S-].[Na+].C(C)(C)(C)OC(=O)N[C@@H](CN1C(N(C(=C(C1=O)C1=C(C(=CC=C1)OC)F)C)CC1=C(C=CC=C1F)F)=O)C1=CC=CC=C1.C[S-].[Na+]>>C(C)(C)(C)OC(=O)N[C@@H](CN1C(N(C(=C(C1=O)C1=C(C(=CC=C1)OC)F)C)CC1=C(C=CC=C1SC)F)=O)C1=CC=CC=C1 | F[c:19]1[c:13]([CH2:12][n:11]2[c:9]([CH3:10])[c:8](-[c:7]3[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[c:43]3[F:44])[c:41](=[O:42])[n:24]([CH2:25][C@H:26]([NH:27][C:28](=[O:29])[O:30][C:31]([CH3:32])([CH3:33])[CH3:34])[c:35]3[cH:36][cH:37][cH:38][cH:39][cH:40]3)[c:22]2=[O:23])[c:14]([F:15])[cH:16][cH:17][cH:18]1.[S-:20][CH3:2... | COc1cccc(-c2c(C)n(Cc3c(F)cccc3F)c(=O)n(C[C@H](NC(=O)OC(C)(C)C)c3ccccc3)c2=O)c1F.C[S-] | COc1cccc(-c2c(C)n(Cc3c(F)cccc3SC)c(=O)n(C[C@H](NC(=O)OC(C)(C)C)c3ccccc3)c2=O)c1F | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | d9ec5bcee0b7dfd36b22f6866beb5073577dcf43715eabace655348751c28bfb | 1813ae14fbd9cacead4dcfaf9efbd2467a19b3e216836766b78aa6647dcfb48a | O=c1c(-c2ccccc2)cn(Cc2ccccc2)c(=O)n1CCc1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]):[c:6].[C;D1;H3:7]-[S-;H0;D1:8]>>[C:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[S;H0;D2;+0:8]-[C;D1;H3:7]):[c:2]:[c:3] | 78.6 | [{"value": 78.0, "product": "C(C)(C)(C)OC(=O)N[C@@H](CN1C(N(C(=C(C1=O)C1=C(C(=CC=C1)OC)F)C)CC1=C(C=CC=C1SC)F)=O)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.6, "product": "C(C)(C)(C)OC(=O)N[C@@H](CN1C(N(C(=C(C1=O)C1=C(C(=CC=C1)OC)F)C)CC1=C(C=CC=C1SC)F)=O)C1=CC=CC=C1", "details": "CALCULAT... | 100 | CELSIUS | null | null | To a solution of compound 5a (33 g, 56 mmol) in dry DMSO (100 mL) was added sodium thiomethoxide (4.0 g, 56 mmol) under nitrogen. The reaction mixture was heated to 100° C. under nitrogen for 1 hour. Another 0.28 eq. of sodium thiomethoxide (1.1 g, 16 mmol) was added, and the reaction mixture was heated to 100° C. unde... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Monosulfide | c1ccccc1 | c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1.c1ccccc1 | Other | CS(=O)C | 100 | null | COc1cccc(-c2c(C)n(Cc3c(F)cccc3F)c(=O)n(C[C@H](NC(=O)OC(C)(C)C)c3ccccc3)c2=O)c1F.C[S-]>CS(=O)C>COc1cccc(-c2c(C)n(Cc3c(F)cccc3SC)c(=O)n(C[C@H](NC(=O)OC(C)(C)C)c3ccccc3)c2=O)c1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3603a9eb0c3044cab88c5864caa24b95 | Cc1c(N)cccc1[N+](=O)[O-]>>O=[N+]([O-])c1cccc2[nH]ncc12 | N(=O)[O-].[Na+].CC1=C(N)C=CC=C1[N+](=O)[O-].N>>[N+](=O)([O-])C1=C2C=NNC2=CC=C1 | [O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([NH2:9])[c:12]1[CH3:11]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8]2[nH:9][n:10][cH:11][c:12]12 | Cc1c(N)cccc1[N+](=O)[O-] | O=[N+]([O-])c1cccc2[nH]ncc12 | null | null | O.C(C)(=O)O.C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | eb7e78ee8505cf2947876c574a0615e4cd65b8009787a831c291647a8c62f230 | 0c2e6cfe0bdb8f8cd78303a7637b3ef339f807f5bc27c4a22ad516ce20b37476 | c1ccc2[nH]ncc2c1 | [CH3;D1;+0:1]-[c:2](:[c:3]):[c:4](-[NH2;D1;+0:5]):[c:6]>>[c:3]:[c:2]1:[cH;D2;+0:1]:[#7;a:7]:[nH;D2;+0:5]:[c:4]:1:[c:6] | null | [] | null | null | 3 | DAY | A mixture of 2-methyl-3-nitro-aniline (5.00 g, 32.9 mmol) and a solution of sodium nitrite (2.27 g, 32.9 mmol) in water (7.5 mL) in glacial acetic acid (750 mL) was was stirred for 15 minutes and allowed to stand at room temperature for 3 days. The mixture was concentrated under reduced pressure leaving a pale yellow s... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccccc1 | c1ccc2[nH]ncc2c1 | c1ccc2[nH]ncc2c1 | Other | O.C(C)(=O)O.C(C)(=O)OCC | null | 72 | Cc1c(N)cccc1[N+](=O)[O-]>O.C(C)(=O)O.C(C)(=O)OCC>O=[N+]([O-])c1cccc2[nH]ncc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2022f7ff30e3468aa8447d7af54d0c16 | ClCCN1CCCC1.O=[N+]([O-])c1cccc2[nH]ncc12>>O=[N+]([O-])c1cccc2c1cnn2CCN1CCCC1 | [N+](=O)([O-])C1=C2C=NNC2=CC=C1.C([O-])([O-])=O.[K+].[K+].Cl.ClCCN1CCCC1>>[N+](=O)([O-])C1=C2C=NN(C2=CC=C1)CCN1CCCC1 | Cl[CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][CH2:18][CH2:19]1.[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8]2[c:9]1[cH:10][n:11][nH:12]2>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8]2[c:9]1[cH:10][n:11][n:12]2[CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][CH2:18][CH2:19]1 | ClCCN1CCCC1.O=[N+]([O-])c1cccc2[nH]ncc12 | O=[N+]([O-])c1cccc2c1cnn2CCN1CCCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 37f45c65843eb1934d1248942acee56370679d83d9e5e49713f458cd256ddf5b | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc2c(c1)cnn2CCN1CCCC1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[c:4]:[c:5]1:[c:6]:[c:7]:[#7;a:8]:[nH;D2;+0:9]:1>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:9]1:[#7;a:8]:[c:7]:[c:6]:[c:5]:1:[c:4] | null | [] | 60 | CELSIUS | null | null | 4-Nitroindazole (3.00 g, 18.4 mmol) and potassium carbonate (7.50 g, 54.4 mmol) in 60 mL of DMF was stirred for 30 minutes after which 1-(2-chloro-ethyl)-pyrrolidine hydrochloride (4.80 g 28.4 mmol) was added. The mixture was heated to 60° C. for 6 hours, cooled to room temperature and filtered through a plug of silica... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2n[nH]cc2c1 | c1cccc2n[nH]cc12 | c1cccc2n[nH]cc12.C1CC[NH]C1 | HCl | CN(C)C=O | 60 | null | ClCCN1CCCC1.O=[N+]([O-])c1cccc2[nH]ncc12>CN(C)C=O>O=[N+]([O-])c1cccc2c1cnn2CCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-232bffef5bf8497b9ca109bcf832a45f | O=[N+]([O-])c1cccc2c1cnn2CCN1CCCC1>>Nc1cccc2c1cnn2CCN1CCCC1 | [N+](=O)([O-])C1=C2C=NN(C2=CC=C1)CCN1CCCC1.[Cl-].[NH4+]>>N1(CCCC1)CCN1N=CC2=C(C=CC=C12)N | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[cH:8][n:9][n:10]2[CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][CH2:16][CH2:17]1>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[cH:8][n:9][n:10]2[CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][CH2:16][CH2:17]1 | O=[N+]([O-])c1cccc2c1cnn2CCN1CCCC1 | Nc1cccc2c1cnn2CCN1CCCC1 | null | [Fe] | C(C)O.O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2c(c1)cnn2CCN1CCCC1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]1:[c:5]:[#7;a:6]:[#7;a:7]:[c:8]:1>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]1:[c:5]:[#7;a:6]:[#7;a:7]:[c:8]:1 | null | [] | null | null | 15 | MINUTE | 4-Nitro-1-(2-pyrrolidin-1-yl-ethyl)-1H-indazole (1.90 g, 7.30 mmol), iron powder (4.10 g, 73.4 mmol), and ammonium chloride (0.200 g, 3.65 mmol) were suspended in a 4:1 solution of ethanol/H2O. The mixture was heated to reflux for 3 hours, cooled to room temperature and concentrated under reduced pressure. The residue ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1cccc2n[nH]cc12.C1CC[NH]C1 | Other | [Fe].C(C)O.O | null | 0.25 | O=[N+]([O-])c1cccc2c1cnn2CCN1CCCC1>[Fe].C(C)O.O>Nc1cccc2c1cnn2CCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0705d34c04cb4ed8b8b6199abebc8b59 | CC(C)(C)OC(=O)NCC(=O)O.Nc1cccc2c1cnn2CCN1CCCC1>>CC(C)(C)OC(=O)NCC(=O)Nc1cccc2c1cnn2CCN1CCCC1 | N1(CCCC1)CCN1N=CC2=C(C=CC=C12)N.C(C)(C)(C)OC(=O)NCC(=O)O.Cl.C(C)N=C=NC(CC)(C)C.ON1N=NC2=C1C=CC=C2.CN1CCOCC1>>C(C)(C)(C)OC(NCC(NC1=C2C=NN(C2=CC=C1)CCN1CCCC1)=O)=O | O[C:10]([CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])=[O:11].[NH2:12][c:13]1[cH:14][cH:15][cH:16][c:17]2[c:18]1[cH:19][n:20][n:21]2[CH2:22][CH2:23][N:24]1[CH2:25][CH2:26][CH2:27][CH2:28]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][C:10](=[O:11])[NH:12][c:13]1[cH:14][cH:15][cH:16][c:... | CC(C)(C)OC(=O)NCC(=O)O.Nc1cccc2c1cnn2CCN1CCCC1 | CC(C)(C)OC(=O)NCC(=O)Nc1cccc2c1cnn2CCN1CCCC1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc2c(c1)cnn2CCN1CCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11].[NH2;D1;+0:12]-[c:13](:[c:14]):[c:15]1:[c:16]:[#7;a:17]:[#7;a:18]:[c:19]:1>>[C;D1;H3:9]-[C:8](-[C;D1;H3:10])(-[C;D1;H3:11])-[#8:7]-[C:5](=[O;D1;H0:6])-[#7:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+... | null | [] | null | null | 6 | HOUR | 1-(2-Pyrrolidin-1-yl-ethyl)-1H-indazol-4-ylamine (1.00 g, 4.34 mmol), tert-butoxycarbonylamino-acetic acid (0.836 g, 4.77 mmol), ethyldimethylpropylcarbodiimide hydrochloride (1.00 g, 5.24 mmol), N-hydroxybenzotriazole (0.707 g, 5.24 mmol) and N-methyl morpholine (1.10 g, 10.9 mmol) were dissolved in 30 mL of DMF, and ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1cccc2n[nH]cc12.C1CC[NH]C1 | HO- | CN(C)C=O | null | 6 | CC(C)(C)OC(=O)NCC(=O)O.Nc1cccc2c1cnn2CCN1CCCC1>CN(C)C=O>CC(C)(C)OC(=O)NCC(=O)Nc1cccc2c1cnn2CCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-69fbdde797e440e99803ed6e568027ab | CC(C)(C)OC(=O)NCC(=O)Nc1cccc2c1cnn2CCN1CCCC1>>NCC(=O)Nc1cccc2c1cnn2CCN1CCCC1 | C(C)(C)(C)OC(NCC(NC1=C2C=NN(C2=CC=C1)CCN1CCCC1)=O)=O.Cl>>NCC(=O)NC1=C2C=NN(C2=CC=C1)CCN1CCCC1.Cl | CC(C)(C)OC(=O)[NH:2][CH2:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[cH:13][n:14][n:15]2[CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][CH2:21][CH2:22]1>>[NH2:2][CH2:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[cH:13][n:14][n:15]2[CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][CH2:21][CH2:22]1 | CC(C)(C)OC(=O)NCC(=O)Nc1cccc2c1cnn2CCN1CCCC1 | NCC(=O)Nc1cccc2c1cnn2CCN1CCCC1 | null | null | ClCCl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc2c(c1)cnn2CCN1CCCC1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[#7:5]-[c:6]>>[NH2;D1;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[#7:5]-[c:6] | null | [] | null | null | 3 | HOUR | {[1-(2-Pyrrolidin-1-yl-ethyl)-1H-indazol-4-ylcarbamoyl]-methyl}-carbamic acid tert-butyl ester (1.00 g, 2.58 mmol) and a solution of HCl (5 mL, 4M in dioxane) was in dichloromethane (30 mL) was stirred for 3 hours. The mixture was filtered and rinsed with dichloromethane to provide the title compound as the bis-HCl sal... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1cccc2n[nH]cc12.C1CC[NH]C1 | HO- | ClCCl | null | 3 | CC(C)(C)OC(=O)NCC(=O)Nc1cccc2c1cnn2CCN1CCCC1>ClCCl>NCC(=O)Nc1cccc2c1cnn2CCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a37a0b99e6e54e88b3ec6ab23609e14e | NCC(=O)Nc1cccc2c1cnn2CCN1CCCC1.O=C(O)Cc1ccc(OCc2ccccc2)cc1>>O=C(CNC(=O)c1ccc(Oc2ccccc2)cc1)Nc1cccc2c1cnn2CCN1CCCC1 | NCC(=O)NC1=C2C=NN(C2=CC=C1)CCN1CCCC1.C(C1=CC=CC=C1)OC1=CC=C(C=C1)CC(=O)O.Cl.C(C)N=C=NC(CC)(C)C.ON1N=NC2=C1C=CC=C2.CN1CCOCC1>>O=C(CNC(C1=CC=C(C=C1)OC1=CC=CC=C1)=O)NC1=C2C=NN(C2=CC=C1)CCN1CCCC1 | [O:1]=[C:2]([CH2:3][NH2:4])[NH:20][c:21]1[cH:22][cH:23][cH:24][c:25]2[c:26]1[cH:27][n:28][n:29]2[CH2:30][CH2:31][N:32]1[CH2:33][CH2:34][CH2:35][CH2:36]1.OC([CH2:5][c:7]1[cH:8][cH:9][c:10]([O:11][CH2:12][c:13]2c[cH:14][cH:15][cH:16][cH:17]2)[cH:18][cH:19]1)=[O:6]>>[O:1]=[C:2]([CH2:3][NH:4][C:5](=[O:6])[c:7]1[cH:8][cH:9]... | NCC(=O)Nc1cccc2c1cnn2CCN1CCCC1.O=C(O)Cc1ccc(OCc2ccccc2)cc1 | O=C(CNC(=O)c1ccc(Oc2ccccc2)cc1)Nc1cccc2c1cnn2CCN1CCCC1 | null | null | CN(C)C=O | Acylation | OtherReaction | ceb4a690423fd80435278c6245612b9377a0d1730cef9f8deb40d19b058498cb | 25b89026811e1b3313674b1746d98ae7463bb6ef1893abcfeee44f8692f48a05 | O=C(CNC(=O)c1ccc(Oc2ccccc2)cc1)Nc1cccc2c1cnn2CCN1CCCC1 | O-C(=[O;H0;D1;+0:1])-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5].[c:6]-[#8:7]-[CH2;D2;+0:8]-[c;H0;D3;+0:9]1:[cH;D2;+0:10]:[c:11]:[c:12]:[cH;D2;+0:13]:c:1.[NH2;D1;+0:14]-[C:15]-[C:16](=[O;D1;H0:17])-[#7:18]-[c:19]>>[O;D1;H0:17]=[C:16](-[#7:18]-[c:19])-[C:15]-[NH;D2;+0:14]-[C;H0;D3;+0:2](=[O;H0;D1;+0:1])-[c:3](:[c:4]):[c:5].[c:6]-... | null | [] | null | null | 6 | HOUR | A mixture of 2-amino-N-[1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-4-yl]-acetamide (HCl salt, 0.0600 g, 0.186 mmol), (4-benzyloxy-phenyl)-acetic acid (0.0470 g, 0.190 mmol), ethyldimethylpropylcarbodiimide hydrochloride (0.0430 g, 0.225 mmol), N-hydroxybenzotriazole (0.0300 g, 0.222 mmol), N-methyl morpholine (0.0460 g, 0.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Primary amine | Ether.Secondary amide | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1cccc2n[nH]cc12.C1CC[NH]C1 | HO- | CN(C)C=O | null | 6 | NCC(=O)Nc1cccc2c1cnn2CCN1CCCC1.O=C(O)Cc1ccc(OCc2ccccc2)cc1>CN(C)C=O>O=C(CNC(=O)c1ccc(Oc2ccccc2)cc1)Nc1cccc2c1cnn2CCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7f56ba04eb234739b0d2989cc4666284 | CCN=C=NC(C)(C)CC.CN1CCOCC1.O=C(O)Cc1ccc(OCc2ccccc2)cc1.On1nnc2ccccc21>>O=C(Cc1ccc(OCc2ccccc2)cc1)Nc1cccc2c1cnn2CCN1CCCC1 | C(C1=CC=CC=C1)OC1=CC=C(C=C1)CC(=O)O.Cl.C(C)N=C=NC(CC)(C)C.ON1N=NC2=C1C=CC=C2.CN1CCOCC1.CN(C)C=O>>C(C1=CC=CC=C1)OC1=CC=C(C=C1)CC(=O)NC1=C2C=NN(C2=CC=C1)CCN1CCCC1 | CCC(C)(C)[N:18]=[C:25]=NC[CH3:32].O1[CH2:28][CH2:29][N:30]([CH3:31])[CH2:34][CH2:33]1.O[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][cH:17]1.O[n:27]1[c:23]2[cH:22][cH:21][cH:20][cH:19][c:24]2n[n:26]1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][c... | CCN=C=NC(C)(C)CC.CN1CCOCC1.O=C(O)Cc1ccc(OCc2ccccc2)cc1.On1nnc2ccccc21 | O=C(Cc1ccc(OCc2ccccc2)cc1)Nc1cccc2c1cnn2CCN1CCCC1 | null | null | null | Acylation | OtherReaction | e4b5922ddfc3dc5712437cc941a8381931131bac2712ab2dbb3b185d441dca86 | 8908fba8100d7a07902b51da5712b4a759cc0f196ddf7ae94db8d0caa41b534d | O=C(Cc1ccc(OCc2ccccc2)cc1)Nc1cccc2c1cnn2CCN1CCCC1 | C-C-C(-C)(-C)-[N;H0;D2;+0:1]=[C;H0;D2;+0:2]=N-C-[CH3;D1;+0:3].O-[C;H0;D3;+0:4](=[O;D1;H0:5])-[C:6]-[c:7].O-[n;H0;D3;+0:8]1:[n;H0;D2;+0:9]:n:[c;H0;D3;+0:10]2:[cH;D2;+0:11]:[c:12]:[c:13]:[c:14]:[c:15]:2:1.[CH3;D1;+0:16]-[#7:17]1-[C:18]-[CH2;D2;+0:19]-O-[CH2;D2;+0:20]-[C:21]-1>>[O;D1;H0:5]=[C;H0;D3;+0:4](-[C:6]-[c:7])-[NH... | null | [] | null | null | null | null | A mixture of Example 1C (42.0 mg, 0.183 mmol), (4-benzyloxy-phenyl)-acetic acid (47.0 mg, 0.194 mmol), ethyldimethylpropylcarbodiimide hydrochloride (43.0 mg, 0.225 mmol), N-hydroxybenzotriazole (30.0 mg, 0.222 mmol), N-methyl morpholine (46.0 mg, 0.455 mmol) in 2 mL of DMF was shaken for 6 hour. The mixture was concen... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether | Secondary amide | C1COCC[NH]1.c1ccc2[nH]nnc2c1 | c1cccc2n[nH]cc12.C1CC[NH]C1 | c1ccccc1.c1ccccc1.c1cccc2n[nH]cc12.C1CC[NH]C1 | HO- | null | null | null | CCN=C=NC(C)(C)CC.CN1CCOCC1.O=C(O)Cc1ccc(OCc2ccccc2)cc1.On1nnc2ccccc21>>O=C(Cc1ccc(OCc2ccccc2)cc1)Nc1cccc2c1cnn2CCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-02c1d54de68d42cdbb45b3d4984a74e2 | Nc1cccc2c1cnn2CCN1CCCC1.O=C(O)Cc1cccc(Oc2ccccc2)c1>>O=C(Cc1cccc(Oc2ccccc2)c1)Nc1cccc2c1cnn2CCN1CCCC1 | N1(CCCC1)CCN1N=CC2=C(C=CC=C12)N.O(C1=CC=CC=C1)C=1C=C(C=CC1)CC(=O)O>>O(C1=CC=CC=C1)C=1C=C(C=CC1)CC(=O)NC1=C2C=NN(C2=CC=C1)CCN1CCCC1 | [NH2:17][c:18]1[cH:19][cH:20][cH:21][c:22]2[c:23]1[cH:24][n:25][n:26]2[CH2:27][CH2:28][N:29]1[CH2:30][CH2:31][CH2:32][CH2:33]1.O[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([O:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16]1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([O:9][c:10]2[cH:11][cH:12][cH:13][... | Nc1cccc2c1cnn2CCN1CCCC1.O=C(O)Cc1cccc(Oc2ccccc2)c1 | O=C(Cc1cccc(Oc2ccccc2)c1)Nc1cccc2c1cnn2CCN1CCCC1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Cc1cccc(Oc2ccccc2)c1)Nc1cccc2c1cnn2CCN1CCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]1:[c:9]:[#7;a:10]:[#7;a:11]:[c:12]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]-[c:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8]1:[c:9]:[#7;a:10]:[#7;a:11]:[c:12]:1 | null | [] | null | null | null | null | 1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-4-ylamine and (3-phenoxy-phenyl)-acetic acid were processed as described in Example 3 to provide the title compound. MS (DCI/NH3) MS m/z 441 (M+H)+; 1H NMR (500 MHz, DMSO-d6) δ ppm 1.83 (m, 2 H), 2.01 (m, 2 H), 3.04 (m, 2 H), 3.52 (m, 2 H), 3.71 (q, J=5.72 Hz, 2 H), 3.79 (s, 2 H),... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1cccc2n[nH]cc12.C1CC[NH]C1 | HO- | null | null | null | Nc1cccc2c1cnn2CCN1CCCC1.O=C(O)Cc1cccc(Oc2ccccc2)c1>>O=C(Cc1cccc(Oc2ccccc2)c1)Nc1cccc2c1cnn2CCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dc42f6c7972040f5bf4d5cc17ffc3227 | Nc1cccc2c1cnn2CCN1CCCC1.O=C(O)Cc1ccc(Oc2ccccc2)cc1>>O=C(Cc1ccc(Oc2ccccc2)cc1)Nc1cccc2c1cnn2CCN1CCCC1 | N1(CCCC1)CCN1N=CC2=C(C=CC=C12)N.O(C1=CC=CC=C1)C1=CC=C(C=C1)CC(=O)O>>O(C1=CC=CC=C1)C1=CC=C(C=C1)CC(=O)NC1=C2C=NN(C2=CC=C1)CCN1CCCC1 | [NH2:17][c:18]1[cH:19][cH:20][cH:21][c:22]2[c:23]1[cH:24][n:25][n:26]2[CH2:27][CH2:28][N:29]1[CH2:30][CH2:31][CH2:32][CH2:33]1.O[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15][cH:16]1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][cH:12][cH:13][... | Nc1cccc2c1cnn2CCN1CCCC1.O=C(O)Cc1ccc(Oc2ccccc2)cc1 | O=C(Cc1ccc(Oc2ccccc2)cc1)Nc1cccc2c1cnn2CCN1CCCC1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Cc1ccc(Oc2ccccc2)cc1)Nc1cccc2c1cnn2CCN1CCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]1:[c:9]:[#7;a:10]:[#7;a:11]:[c:12]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]-[c:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8]1:[c:9]:[#7;a:10]:[#7;a:11]:[c:12]:1 | null | [] | null | null | null | null | 1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-4-ylamine and (4-phenoxy-phenyl)-acetic acid were processed as describe in Example 3 to provide the title compound. 1H NMR (300 MHz, DMSO-D6) δ ppm 1.61 (m, 4 H), 2.43 (m, J=5.43 Hz, 4 H), 2.86 (t, J=6.78 Hz, 2 H), 3.78 (s, 2 H), 4.47 (t, J=6.61 Hz, 2 H), 6.99 (m, 4 H), 7.12 (m, 1... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1cccc2n[nH]cc12.C1CC[NH]C1 | HO- | null | null | null | Nc1cccc2c1cnn2CCN1CCCC1.O=C(O)Cc1ccc(Oc2ccccc2)cc1>>O=C(Cc1ccc(Oc2ccccc2)cc1)Nc1cccc2c1cnn2CCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ffde62cd866f484f85d9d09b95451b0c | Nc1cccc2c1cnn2CCN1CCCC1.O=C(O)CCc1ccc(Oc2ccccc2)cc1>>O=C(CCc1ccc(Oc2ccccc2)cc1)Nc1cccc2c1cnn2CCN1CCCC1 | N1(CCCC1)CCN1N=CC2=C(C=CC=C12)N.O(C1=CC=CC=C1)C1=CC=C(C=C1)CCC(=O)O>>O(C1=CC=CC=C1)C1=CC=C(C=C1)CCC(=O)NC1=C2C=NN(C2=CC=C1)CCN1CCCC1 | [NH2:18][c:19]1[cH:20][cH:21][cH:22][c:23]2[c:24]1[cH:25][n:26][n:27]2[CH2:28][CH2:29][N:30]1[CH2:31][CH2:32][CH2:33][CH2:34]1.O[C:2](=[O:1])[CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([O:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][cH:17]1>>[O:1]=[C:2]([CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([O:9][c:10]2[cH:11][cH:12... | Nc1cccc2c1cnn2CCN1CCCC1.O=C(O)CCc1ccc(Oc2ccccc2)cc1 | O=C(CCc1ccc(Oc2ccccc2)cc1)Nc1cccc2c1cnn2CCN1CCCC1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CCc1ccc(Oc2ccccc2)cc1)Nc1cccc2c1cnn2CCN1CCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]1:[c:9]:[#7;a:10]:[#7;a:11]:[c:12]:1>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8]1:[c:9]:[#7;a:10]:[#7;a:11]:[c:12]:1 | null | [] | null | null | null | null | 1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-4-ylamine and 3-(4-phenoxy-phenyl)-propionic acid were processed according as described in Example 3 to provide the title compound. 1H NMR (500 MHz, DMSO-D6) δ ppm 1.84 (m, 2 H), 2.00 (m, 2 H), 2.64 (t, J=7.64 Hz, 2 H), 2.93 (t, J=7.64 Hz, 2 H), 3.06 (m, 2 H), 3.52 (m, 2 H), 3.71 ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1cccc2n[nH]cc12.C1CC[NH]C1 | HO- | null | null | null | Nc1cccc2c1cnn2CCN1CCCC1.O=C(O)CCc1ccc(Oc2ccccc2)cc1>>O=C(CCc1ccc(Oc2ccccc2)cc1)Nc1cccc2c1cnn2CCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-25a06987aa1b4da39ce701e2c7785851 | O=C(Cc1ccc(OCc2ccccc2)cc1)Nc1cccc2c1cnn2CCN1CCCC1>>O=C(Cc1ccc(O)cc1)Nc1cccc2c1cnn2CCN1CCCC1 | C(C1=CC=CC=C1)OC1=CC=C(C=C1)CC(=O)NC1=C2C=NN(C2=CC=C1)CCN1CCCC1>>OC1=CC=C(C=C1)CC(=O)NC1=C2C=NN(C2=CC=C1)CCN1CCCC1 | c1ccc(C[O:8][c:7]2[cH:6][cH:5][c:4]([CH2:3][C:2](=[O:1])[NH:11][c:12]3[cH:13][cH:14][cH:15][c:16]4[c:17]3[cH:18][n:19][n:20]4[CH2:21][CH2:22][N:23]3[CH2:24][CH2:25][CH2:26][CH2:27]3)[cH:10][cH:9]2)cc1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:9][cH:10]1)[NH:11][c:12]1[cH:13][cH:14][cH:15][c:16]2[c:17]1[cH:... | O=C(Cc1ccc(OCc2ccccc2)cc1)Nc1cccc2c1cnn2CCN1CCCC1 | O=C(Cc1ccc(O)cc1)Nc1cccc2c1cnn2CCN1CCCC1 | null | [Pd] | C(C)O | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(Cc1ccccc1)Nc1cccc2c1cnn2CCN1CCCC1 | [c:1]:[c:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4] | null | [] | null | null | 6 | HOUR | 2-(4-Benzyloxy-phenyl)-N-[1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-4-yl]-acetamide (Example 3, 500 mg, 1.10 mmol) and Pd (50 mg, 10% on carbon) were suspended in ethanol (40 mL) and stirred under a hydrogen atmosphere at room temperature for 6 hours. The mixture was filtered and the filtrate was concentrated under reduce... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccccc1.c1cccc2n[nH]cc12.C1CC[NH]C1 | Other | [Pd].C(C)O | null | 6 | O=C(Cc1ccc(OCc2ccccc2)cc1)Nc1cccc2c1cnn2CCN1CCCC1>[Pd].C(C)O>O=C(Cc1ccc(O)cc1)Nc1cccc2c1cnn2CCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f9d91439e9bb4de78088195624bbb089 | Fc1cccc(CBr)c1F.O=C(Cc1ccc(O)cc1)Nc1cccc2c1cnn2CCN1CCCC1>>O=C(Cc1ccc(OCc2cccc(F)c2F)cc1)Nc1cccc2c1cnn2CCN1CCCC1 | OC1=CC=C(C=C1)CC(=O)NC1=C2C=NN(C2=CC=C1)CCN1CCCC1.BrCC1=C(C(=CC=C1)F)F.C(=O)([O-])[O-].[Cs+].[Cs+]>>FC1=C(COC2=CC=C(C=C2)CC(=O)NC2=C3C=NN(C3=CC=C2)CCN2CCCC2)C=CC=C1F | Br[CH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]([F:15])[c:16]1[F:17].[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:18][cH:19]1)[NH:20][c:21]1[cH:22][cH:23][cH:24][c:25]2[c:26]1[cH:27][n:28][n:29]2[CH2:30][CH2:31][N:32]1[CH2:33][CH2:34][CH2:35][CH2:36]1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][c:10]2... | Fc1cccc(CBr)c1F.O=C(Cc1ccc(O)cc1)Nc1cccc2c1cnn2CCN1CCCC1 | O=C(Cc1ccc(OCc2cccc(F)c2F)cc1)Nc1cccc2c1cnn2CCN1CCCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(Cc1ccc(OCc2ccccc2)cc1)Nc1cccc2c1cnn2CCN1CCCC1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | null | [] | null | null | 6 | HOUR | A mixture of 2-(4-hydroxy-phenyl)-N-[1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-4-yl]-acetamide (45.0 mg, 0.124 mmol), 1-bromomethyl-2,3-difluoro-benzene (38.0 mg, 0.185 mmol), Cs2CO3 (60.0 mg, 0.184 mmol) in 2 mL of DMF was shaken for 6 hours after which the mixture was concentrated under reduced pressure. The residue was... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1cccc2n[nH]cc12.C1CC[NH]C1 | HBr | CN(C)C=O | null | 6 | Fc1cccc(CBr)c1F.O=C(Cc1ccc(O)cc1)Nc1cccc2c1cnn2CCN1CCCC1>CN(C)C=O>O=C(Cc1ccc(OCc2cccc(F)c2F)cc1)Nc1cccc2c1cnn2CCN1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ac0520d769764bfc91c80e44d5ffe0eb | ClCCN1CCOCC1.O=[N+]([O-])c1cccc2[nH]ncc12>>O=[N+]([O-])c1cccc2c1cnn2CCN1CCOCC1 | [N+](=O)([O-])C1=C2C=NNC2=CC=C1.C([O-])([O-])=O.[K+].[K+].Cl.ClCCN1CCOCC1>>N1(CCOCC1)CCN1N=CC2=C(C=CC=C12)[N+](=O)[O-] | Cl[CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1.[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8]2[c:9]1[cH:10][n:11][nH:12]2>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8]2[c:9]1[cH:10][n:11][n:12]2[CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1 | ClCCN1CCOCC1.O=[N+]([O-])c1cccc2[nH]ncc12 | O=[N+]([O-])c1cccc2c1cnn2CCN1CCOCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 37f45c65843eb1934d1248942acee56370679d83d9e5e49713f458cd256ddf5b | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc2c(c1)cnn2CCN1CCOCC1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[c:4]:[c:5]1:[c:6]:[c:7]:[#7;a:8]:[nH;D2;+0:9]:1>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:9]1:[#7;a:8]:[c:7]:[c:6]:[c:5]:1:[c:4] | null | [] | 60 | CELSIUS | null | null | 4-Nitroindazole (1.00 g, 6.13 mmol) and potassium carbonate (2.55 g, 18.4 mmol) in 15 mL of DMF was stirred for 30 min, after which 4-(2-chloro-ethyl)-morpholine hydrochloride (1.71 g, 9.19 mmol) was added. The reaction mixture was heated to 60° C. for 6 hours, cooled to room temperature and filtered through a plug of ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2n[nH]cc2c1 | c1cccc2n[nH]cc12 | c1cccc2n[nH]cc12.C1COCC[NH]1 | HCl | CN(C)C=O | 60 | null | ClCCN1CCOCC1.O=[N+]([O-])c1cccc2[nH]ncc12>CN(C)C=O>O=[N+]([O-])c1cccc2c1cnn2CCN1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8fffc72fd57b49f284ad0ff03fffb3d0 | CC(C)(C)OC(=O)NCC(=O)O.CCN=C=NC(C)(C)CC.CN1CCOCC1.On1nnc2ccccc21>>CC(C)(C)OC(=O)NCC(=O)Nc1cccc2c1cnn2CCN1CCOCC1 | C(C)(C)(C)OC(=O)NCC(=O)O.Cl.C(C)N=C=NC(CC)(C)C.ON1N=NC2=C1C=CC=C2.CN1CCOCC1.CN(C)C=O>>C(C)(C)(C)OC(NCC(NC1=C2C=NN(C2=CC=C1)CCN1CCOCC1)=O)=O | O[C:10]([CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])=[O:11].CCC(C)(C)[N:12]=[C:19]=NC[CH3:22].[CH3:23][N:24]1[CH2:25][CH2:26][O:27][CH2:28][CH2:29]1.O[n:21]1[c:17]2[cH:16][cH:15][cH:14][cH:13][c:18]2n[n:20]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][C:10](=[O:11])[NH:12][c:13]1[cH... | CC(C)(C)OC(=O)NCC(=O)O.CCN=C=NC(C)(C)CC.CN1CCOCC1.On1nnc2ccccc21 | CC(C)(C)OC(=O)NCC(=O)Nc1cccc2c1cnn2CCN1CCOCC1 | null | null | null | Acylation | OtherReaction | d1094538aa92f0a8ba4746b4521ce734c2d0031991260ae2a2226f0e63c6f0a2 | 1aed08436638136927b8225fa24aefe8cee58785c276949e21bad391c05ec286 | c1ccc2c(c1)cnn2CCN1CCOCC1 | C-C-C(-C)(-C)-[N;H0;D2;+0:1]=[C;H0;D2;+0:2]=N-C-[CH3;D1;+0:3].O-[C;H0;D3;+0:4](=[O;D1;H0:5])-[C:6]-[#7:7]-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[C;D1;H3:14].O-[n;H0;D3;+0:15]1:[n;H0;D2;+0:16]:n:[c;H0;D3;+0:17]2:[cH;D2;+0:18]:[c:19]:[c:20]:[c:21]:[c:22]:2:1.[C:23]-[#7:24](-[CH3;D1;+0:25])-[C:2... | null | [] | null | null | 6 | HOUR | A mixture of 1-(2-morpholin-1-yl-ethyl)-1H-indazol-4-ylamine (0.150 g, 0.609 mmol), tert-butoxycarbonylamino-acetic acid (0.109 g, 0.548 mmol), ethyldimethylpropylcarbodiimide hydrochloride (0.126 g, 0.660 mmol), N-hydroxybenzotriazole (0.0884 g, 0.657 mmol) and N-methyl morpholine (0.150 mL, 1.33 mmol) in 3.6 mL of DM... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Secondary amide | c1ccc2[nH]nnc2c1 | c1cccc2n[nH]cc12 | c1cccc2n[nH]cc12.C1COCC[NH]1 | HO- | null | null | 6 | CC(C)(C)OC(=O)NCC(=O)O.CCN=C=NC(C)(C)CC.CN1CCOCC1.On1nnc2ccccc21>>CC(C)(C)OC(=O)NCC(=O)Nc1cccc2c1cnn2CCN1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-68a75aedd2c544b48f0ee06471fa621f | ClCCC1CCNCC1.O=[N+]([O-])c1cccc2[nH]ncc12>>O=[N+]([O-])c1cccc2c1cnn2CCN1CCCCC1 | [N+](=O)([O-])C1=C2C=NNC2=CC=C1.C([O-])([O-])=O.[K+].[K+].CN(C)C=O.Cl.ClCCC1CCNCC1>>[N+](=O)([O-])C1=C2C=NN(C2=CC=C1)CCN1CCCCC1 | Cl[CH2:13][CH2:14][CH:18]1[CH2:17][CH2:16][NH:15][CH2:20][CH2:19]1.[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8]2[c:9]1[cH:10][n:11][nH:12]2>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8]2[c:9]1[cH:10][n:11][n:12]2[CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1 | ClCCC1CCNCC1.O=[N+]([O-])c1cccc2[nH]ncc12 | O=[N+]([O-])c1cccc2c1cnn2CCN1CCCCC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4bd3bffa78396b61ef5f002882073119ed4e68f890208e08824aa777944e12c0 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc2c(c1)cnn2CCN1CCCCC1 | Cl-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[CH;D3;+0:3]1-[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]-1.[c:9]:[c:10]1:[c:11]:[c:12]:[#7;a:13]:[nH;D2;+0:14]:1>>[c:9]:[c:10]1:[c:11]:[c:12]:[#7;a:13]:[n;H0;D3;+0:14]:1-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[N;H0;D3;+0:6]1-[C:5]-[C:4]-[CH2;D2;+0:3]-[C:8]-[C:7]-1 | null | [] | 60 | CELSIUS | 30 | MINUTE | 4-Nitroindazole (mmol) and potassium carbonate (mmol) in 60 mL of DMF was added was stirred for 30 minutes, after which 4-(2-chloro-ethyl)-piperidine hydrochloride (mmol) was added. The mixture was heated to 60° C. for 6 hours, cooled to room temperature and the mixture filtered through a plug of silica gel which was r... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1.c1ccc2n[nH]cc2c1 | c1cccc2n[nH]cc12.C1CC[NH]CC1 | c1cccc2n[nH]cc12.C1CC[NH]CC1 | HCl | null | 60 | 0.5 | ClCCC1CCNCC1.O=[N+]([O-])c1cccc2[nH]ncc12>>O=[N+]([O-])c1cccc2c1cnn2CCN1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ac9554965d8a402485769ded1cdb274d | O=[N+]([O-])c1cccc2c1cnn2CCN1CCCCC1>>Nc1cccc2c1cnn2CCN1CCCCC1 | [N+](=O)([O-])C1=C2C=NN(C2=CC=C1)CCN1CCCCC1.[Cl-].[NH4+]>>N1(CCCCC1)CCN1N=CC2=C(C=CC=C12)N | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[cH:8][n:9][n:10]2[CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[cH:8][n:9][n:10]2[CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1 | O=[N+]([O-])c1cccc2c1cnn2CCN1CCCCC1 | Nc1cccc2c1cnn2CCN1CCCCC1 | null | [Fe] | C(C)O.O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2c(c1)cnn2CCN1CCCCC1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]1:[c:5]:[#7;a:6]:[#7;a:7]:[c:8]:1>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]1:[c:5]:[#7;a:6]:[#7;a:7]:[c:8]:1 | null | [] | null | null | 15 | MINUTE | A mixture of 4-Nitro-1-(2-piperidin-1-yl-ethyl)-1H-indazole (mmol), iron powder (mmol), and ammonium chloride (mmol) in a 4:1 solution of ethanol/H2O was heated to reflux for 2 hours, cooled to room temperature and concentrated under reduced pressure. The residue was stirred in triethylamine/ethyl acetate (1/4, 30 mL) ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1cccc2n[nH]cc12.C1CC[NH]CC1 | Other | [Fe].C(C)O.O | null | 0.25 | O=[N+]([O-])c1cccc2c1cnn2CCN1CCCCC1>[Fe].C(C)O.O>Nc1cccc2c1cnn2CCN1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-aa40f988fca74a3db57a91cdfda43748 | CC(C)(C)OC(=O)NCC(=O)O.Nc1cccc2c1cnn2CCN1CCCCC1>>CC(C)(C)OC(=O)NCC(=O)Nc1cccc2c1cnn2CCN1CCCCC1 | N1(CCCCC1)CCN1N=CC2=C(C=CC=C12)N.C(C)(C)(C)OC(=O)NCC(=O)O.Cl.C(C)N=C=NC(CC)(C)C.ON1N=NC2=C1C=CC=C2.CN1CCOCC1>>O=C(CNC(OC(C)(C)C)=O)NC1=C2C=NN(C2=CC=C1)CCN1CCCCC1 | O[C:10]([CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])=[O:11].[NH2:12][c:13]1[cH:14][cH:15][cH:16][c:17]2[c:18]1[cH:19][n:20][n:21]2[CH2:22][CH2:23][N:24]1[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][C:10](=[O:11])[NH:12][c:13]1[cH:14][cH:15][c... | CC(C)(C)OC(=O)NCC(=O)O.Nc1cccc2c1cnn2CCN1CCCCC1 | CC(C)(C)OC(=O)NCC(=O)Nc1cccc2c1cnn2CCN1CCCCC1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc2c(c1)cnn2CCN1CCCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11].[NH2;D1;+0:12]-[c:13](:[c:14]):[c:15]1:[c:16]:[#7;a:17]:[#7;a:18]:[c:19]:1>>[C;D1;H3:9]-[C:8](-[C;D1;H3:10])(-[C;D1;H3:11])-[#8:7]-[C:5](=[O;D1;H0:6])-[#7:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+... | null | [] | null | null | 6 | HOUR | A mixture of 1-(2-piperidin-1-yl-ethyl)-1H-indazol-4-ylamine (mmol), tert-butoxycarbonylamino-acetic acid (mmol), ethyldimethylpropylcarbodiimide hydrochloride (mmol), N-hydroxybenzotriazole (mmol) and N-methyl morpholine (mmol) were dissolved in 15 mL of DMF and stirred at room temperature for 6 hours. The mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1cccc2n[nH]cc12.C1CC[NH]CC1 | HO- | CN(C)C=O | null | 6 | CC(C)(C)OC(=O)NCC(=O)O.Nc1cccc2c1cnn2CCN1CCCCC1>CN(C)C=O>CC(C)(C)OC(=O)NCC(=O)Nc1cccc2c1cnn2CCN1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4f4be7aff6c1435cb2399bf62f629f25 | CN(C)CCCl.O=[N+]([O-])c1cccc2[nH]ncc12>>CN(C)CCn1ncc2c([N+](=O)[O-])cccc21 | [N+](=O)([O-])C1=C2C=NNC2=CC=C1.C([O-])([O-])=O.[K+].[K+].Cl.CN(CCCl)C>>CN(CCN1N=CC2=C(C=CC=C12)[N+](=O)[O-])C | Cl[CH2:5][CH2:4][N:2]([CH3:1])[CH3:3].[nH:6]1[n:7][cH:8][c:9]2[c:10]([N+:11](=[O:12])[O-:13])[cH:14][cH:15][cH:16][c:17]12>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][n:6]1[n:7][cH:8][c:9]2[c:10]([N+:11](=[O:12])[O-:13])[cH:14][cH:15][cH:16][c:17]12 | CN(C)CCCl.O=[N+]([O-])c1cccc2[nH]ncc12 | CN(C)CCn1ncc2c([N+](=O)[O-])cccc21 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 8f1c4be45674b1b8700a03467b438fc9ea0bf1e3e4c0238414c6f317b2d80fde | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc2[nH]ncc2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[c:4]:[c:5]1:[c:6]:[c:7]:[#7;a:8]:[nH;D2;+0:9]:1>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:9]1:[#7;a:8]:[c:7]:[c:6]:[c:5]:1:[c:4] | 56.9 | [{"value": 50.0, "product": "CN(CCN1N=CC2=C(C=CC=C12)[N+](=O)[O-])C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.9, "product": "CN(CCN1N=CC2=C(C=CC=C12)[N+](=O)[O-])C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 30 | MINUTE | A mixture of 4-nitroindazole (2.0 g, 12 mmol) and potassium carbonate (5.1 g 37 mmol) in DMF (40 mL) was stirred for 30 minutes, after which 2-(dimethylamino)ethylchloride hydrochloride (2.7 g 18 mmol) was added. The mixture was heated to 60° C. for 6 hours, cooled to room temperature and filtered through a plug of sil... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ncc2c1 | c1cccc2[nH]ncc12 | c1cccc2[nH]ncc12 | HCl | CN(C)C=O | 60 | 0.5 | CN(C)CCCl.O=[N+]([O-])c1cccc2[nH]ncc12>CN(C)C=O>CN(C)CCn1ncc2c([N+](=O)[O-])cccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4ca1a1240dbe4be590c8ae11a92ef18e | CN(C)CCn1ncc2c([N+](=O)[O-])cccc21.O=C(O)Cc1ccc(Oc2ccccc2)cc1>>CN(C)CCn1ncc2c(NC(=O)Cc3ccc(Oc4ccccc4)cc3)cccc21 | CN(CCN1N=CC2=C(C=CC=C12)[N+](=O)[O-])C.[Cl-].[NH4+].O(C1=CC=CC=C1)C1=CC=C(C=C1)CC(=O)O>>CN(CCN1N=CC2=C(C=CC=C12)NC(CC1=CC=C(C=C1)OC1=CC=CC=C1)=O)C | O=[N+:11]([O-])[c:10]1[c:9]2[cH:8][n:7][n:6]([CH2:5][CH2:4][N:2]([CH3:1])[CH3:3])[c:31]2[cH:30][cH:29][cH:28]1.O[C:12](=[O:13])[CH2:14][c:15]1[cH:16][cH:17][c:18]([O:19][c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[cH:26][cH:27]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][n:6]1[n:7][cH:8][c:9]2[c:10]([NH:11][C:12](=[O:13])[CH... | CN(C)CCn1ncc2c([N+](=O)[O-])cccc21.O=C(O)Cc1ccc(Oc2ccccc2)cc1 | CN(C)CCn1ncc2c(NC(=O)Cc3ccc(Oc4ccccc4)cc3)cccc21 | null | [Fe] | C(C)O.O | Acylation | OtherReaction | 07d1695adb57fcbe166e427114577c880df19df2ee26bdadcbdf979c1785ff55 | 141f63f004bbbe912fc54e457ad7143d740953538a28293f72b74ca32c03fab9 | O=C(Cc1ccc(Oc2ccccc2)cc1)Nc1cccc2[nH]ncc12 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].O=[N+;H0;D3:5](-[O-])-[c:6](:[c:7]):[c:8]1:[c:9]:[#7;a:10]:[#7;a:11]:[c:12]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]-[c:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8]1:[c:9]:[#7;a:10]:[#7;a:11]:[c:12]:1 | null | [] | null | null | 15 | MINUTE | A mixture of dimethyl-[2-(4-nitro-indazol-1-yl)-ethyl]-amine (1.6 g, 6.8 mmol), iron powder (3.8 g, 68 mmol), and ammonium chloride (0.18 g, 3.4 mmol) in a 4:1 ethanol/H2O solution (20 mL) was heated to reflux for 3 hours, cooled to room temperature and concentrated under reduced pressure. The residue was taken up and ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitro group | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1cccc2[nH]ncc12 | Other | [Fe].C(C)O.O | null | 0.25 | CN(C)CCn1ncc2c([N+](=O)[O-])cccc21.O=C(O)Cc1ccc(Oc2ccccc2)cc1>[Fe].C(C)O.O>CN(C)CCn1ncc2c(NC(=O)Cc3ccc(Oc4ccccc4)cc3)cccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fe535716bd464677bd0d45fbe39c8032 | C(=NC1CCCCC1)=NC1CCCCC1.CCN(C(C)C)C(C)C.O=C(O)Cc1ccc(OCc2ccccc2)cc1.On1nnc2ccccc21>>C[C@@H]1CCCN1CCn1ncc2c(NC(=O)Cc3ccc(OCc4ccccc4)cc3)cccc21 | C1CCC(CC1)N=C=NC2CCCCC2.ON1N=NC2=C1C=CC=C2.C(C)(C)N(CC)C(C)C.C(C1=CC=CC=C1)OC1=CC=C(C=C1)CC(=O)O.CN(C)C=O>>C(C1=CC=CC=C1)OC1=CC=C(C=C1)CC(=O)NC1=C2C=NN(C2=CC=C1)CCN1[C@@H](CCC1)C | C(=NC1CCCCC1)=[N:14]C1CCCC[CH2:3]1.C[CH:2]([CH3:1])[N:6]([CH:5](C)[CH3:4])[CH2:8][CH3:7].O[C:15](=[O:16])[CH2:17][c:18]1[cH:19][cH:20][c:21]([O:22][CH2:23][c:24]2[cH:25][cH:26][cH:27][cH:28][cH:29]2)[cH:30][cH:31]1.O[n:9]1[n:10]n[c:12]2[cH:13][cH:32][cH:33][cH:34][c:35]12>>[CH3:1][C@@H:2]1[CH2:3][CH2:4][CH2:5][N:6]1[CH... | C(=NC1CCCCC1)=NC1CCCCC1.CCN(C(C)C)C(C)C.O=C(O)Cc1ccc(OCc2ccccc2)cc1.On1nnc2ccccc21 | C[C@@H]1CCCN1CCn1ncc2c(NC(=O)Cc3ccc(OCc4ccccc4)cc3)cccc21 | null | null | null | Acylation | OtherReaction | c07576caf771d64f71d0f4c47b963f1f11b4514507357959db6dd773aa7f4b33 | 88eb889ed7ec64e0dc62f6ea1d442b5f03bdd31a3c1b695965ec97b988ba61df | O=C(Cc1ccc(OCc2ccccc2)cc1)Nc1cccc2c1cnn2CCN1CCCC1 | C-[CH;D3;+0:1](-[C;D1;H3:2])-[N;H0;D3;+0:3](-[CH2;D2;+0:4]-[CH3;D1;+0:5])-[CH;D3;+0:6](-C)-[CH3;D1;+0:7].C1-C-C-C(-N=C=[N;H0;D2;+0:8]-C2-C-C-C-C-[CH2;D2;+0:9]-2)-C-C-1.O-[C;H0;D3;+0:10](=[O;D1;H0:11])-[C:12]-[c:13].O-[n;H0;D3;+0:14]1:[n;H0;D2;+0:15]:n:[c;H0;D3;+0:16]2:[cH;D2;+0:17]:[c:18]:[c:19]:[c:20]:[c:21]:2:1>>[C;D... | null | [] | 55 | CELSIUS | null | null | The residue, 46.0 mg N-hydroxybenzotriazole (0.341 mmol), 0.170 mL of diisopropylethylamine (0.976 mmol), and 65.0 mg (0.269 mmol) of (4-benzyloxy-phenyl)-acetic acid was dissolved in 4 mL of DMF followed by the addition of 0.520 mg of PS-DCC resin (1.3 mmol/g, 0.676 mmol, 2.83 equiv) after which it was shaken and heat... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary amine | Secondary amide.Tertiary amine | C1CCCCC1.C1CCCCC1.c1ccc2[nH]nnc2c1 | C1CC[NH]C1.c1cccc2[nH]ncc12 | C1CC[NH]C1.c1ccccc1.c1ccccc1.c1cccc2[nH]ncc12 | HO- | null | 55 | null | C(=NC1CCCCC1)=NC1CCCCC1.CCN(C(C)C)C(C)C.O=C(O)Cc1ccc(OCc2ccccc2)cc1.On1nnc2ccccc21>>C[C@@H]1CCCN1CCn1ncc2c(NC(=O)Cc3ccc(OCc4ccccc4)cc3)cccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8968eaee96e44cef878044b143044ce3 | ClCCN1CCCC1.O=[N+]([O-])c1ccc2[nH]ncc2c1>>O=[N+]([O-])c1ccc2c(cnn2CCN2CCCC2)c1 | [N+](=O)([O-])C=1C=C2C=NNC2=CC1.C([O-])([O-])=O.[K+].[K+].Cl.ClCCN1CCCC1>>[N+](=O)([O-])C=1C=C2C=NN(C2=CC1)CCN1CCCC1 | Cl[CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][CH2:17][CH2:18]1.[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9][n:10][nH:11]2)[cH:19]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9][n:10][n:11]2[CH2:12][CH2:13][N:14]2[CH2:15][CH2:16][CH2:17][CH2:18]2)[cH:19]1 | ClCCN1CCCC1.O=[N+]([O-])c1ccc2[nH]ncc2c1 | O=[N+]([O-])c1ccc2c(cnn2CCN2CCCC2)c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 1c9bfadcc8b17ce33571db0aba6fe4d2adf28d49d529bcf12a641e342e01b0dc | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc2c(c1)cnn2CCN1CCCC1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[c:4]:[c:5]1:[c:6]:[c:7]:[#7;a:8]:[nH;D2;+0:9]:1>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:9]1:[#7;a:8]:[c:7]:[c:6]:[c:5]:1:[c:4] | null | [] | 60 | CELSIUS | null | null | A mixture of 5-nitroindazole (3.00 g, 18.4 mmol) and potassium carbonate (7.50 g, 54.4 mmol) in DMF (60 mL) was stirred for 30 minutes after which 1-(2-chloro-ethyl)-pyrrolidine hydrochloride (4.80 g, 28.4 mmol) was added. The mixture was heated to 60° C. for 6 hours, cooled to room temperature and filtered through a p... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2n[nH]cc2c1 | c1ccc2n[nH]cc2c1 | c1ccc2n[nH]cc2c1.C1CC[NH]C1 | HCl | CN(C)C=O | 60 | null | ClCCN1CCCC1.O=[N+]([O-])c1ccc2[nH]ncc2c1>CN(C)C=O>O=[N+]([O-])c1ccc2c(cnn2CCN2CCCC2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5db7914aba2741b29ed80ae6060453c2 | O=[N+]([O-])c1ccc2c(cnn2CCN2CCCC2)c1>>Nc1ccc2c(cnn2CCN2CCCC2)c1 | [N+](=O)([O-])C=1C=C2C=NN(C2=CC1)CCN1CCCC1.[Cl-].[NH4+]>>N1(CCCC1)CCN1N=CC2=CC(=CC=C12)N | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7][n:8][n:9]2[CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH2:15][CH2:16]2)[cH:17]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7][n:8][n:9]2[CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH2:15][CH2:16]2)[cH:17]1 | O=[N+]([O-])c1ccc2c(cnn2CCN2CCCC2)c1 | Nc1ccc2c(cnn2CCN2CCCC2)c1 | null | [Fe] | C(C)O.O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2c(c1)cnn2CCN1CCCC1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 15 | MINUTE | A mixture of 5-Nitro-1-(2-pyrrolidin-1-yl-ethyl)-1H-indazole (3.00 g, 11.5 mmol), iron powder (6.50 g, 116 mmol), and ammonium chloride (310 mg, 5.85 mmol) in a 4:1 mixture of ethanol/H2O was heated to reflux for 3 hours, cooled to room temperature and concentrated under reduced pressure. The residue was taken up and s... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2n[nH]cc2c1.C1CC[NH]C1 | Other | [Fe].C(C)O.O | null | 0.25 | O=[N+]([O-])c1ccc2c(cnn2CCN2CCCC2)c1>[Fe].C(C)O.O>Nc1ccc2c(cnn2CCN2CCCC2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3eaf4fd4d6384d8d8bdad263b5961478 | Nc1ccc2c(cnn2CCN2CCCC2)c1.O=C(O)Cc1ccc(OCc2ccccc2)cc1>>O=C(Cc1ccc(OCc2ccccc2)cc1)Nc1ccc2c(cnn2CCN2CCCC2)c1 | N1(CCCC1)CCN1N=CC2=CC(=CC=C12)N.C(C1=CC=CC=C1)OC1=CC=C(C=C1)CC(=O)O.Cl.C(C)N=C=NC(CC)(C)C.ON1N=NC2=C1C=CC=C2.CN1CCOCC1>>C(C1=CC=CC=C1)OC1=CC=C(C=C1)CC(=O)NC=1C=C2C=NN(C2=CC1)CCN1CCCC1 | [NH2:18][c:19]1[cH:20][cH:21][c:22]2[c:23]([cH:24][n:25][n:26]2[CH2:27][CH2:28][N:29]2[CH2:30][CH2:31][CH2:32][CH2:33]2)[cH:34]1.O[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][cH:17]1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:... | Nc1ccc2c(cnn2CCN2CCCC2)c1.O=C(O)Cc1ccc(OCc2ccccc2)cc1 | O=C(Cc1ccc(OCc2ccccc2)cc1)Nc1ccc2c(cnn2CCN2CCCC2)c1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Cc1ccc(OCc2ccccc2)cc1)Nc1ccc2c(cnn2CCN2CCCC2)c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]-[c:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | 6 | HOUR | A mixture of 1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-5-ylamine (60 mg, 0.26 mmol), (4-benzyloxy-phenyl)-acetic acid (63 mg, 0.26 mmol), ethyldimethylpropylcarbodiimide hydrochloride (60 mg g, 0.31 mmol), N-hydroxybenzotriazole (42 mg, 0.31 mmol), and N-methyl morpholine (66 mg, 0.62 mmol) in 2 mL of DMF was shaken for 6... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2n[nH]cc2c1.C1CC[NH]C1 | HO- | CN(C)C=O | null | 6 | Nc1ccc2c(cnn2CCN2CCCC2)c1.O=C(O)Cc1ccc(OCc2ccccc2)cc1>CN(C)C=O>O=C(Cc1ccc(OCc2ccccc2)cc1)Nc1ccc2c(cnn2CCN2CCCC2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3ece81743de44beb9844a6311414d126 | Nc1ccc2c(cnn2CCN2CCCC2)c1.O=C(O)CCc1ccc(Oc2ccccc2)cc1>>O=C(CCc1ccc(Oc2ccccc2)cc1)Nc1ccc2c(cnn2CCN2CCCC2)c1 | N1(CCCC1)CCN1N=CC2=CC(=CC=C12)N.O(C1=CC=CC=C1)C1=CC=C(C=C1)CCC(=O)O>>O(C1=CC=CC=C1)C1=CC=C(C=C1)CCC(=O)NC=1C=C2C=NN(C2=CC1)CCN1CCCC1 | [NH2:18][c:19]1[cH:20][cH:21][c:22]2[c:23]([cH:24][n:25][n:26]2[CH2:27][CH2:28][N:29]2[CH2:30][CH2:31][CH2:32][CH2:33]2)[cH:34]1.O[C:2](=[O:1])[CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([O:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][cH:17]1>>[O:1]=[C:2]([CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([O:9][c:10]2[cH:11][cH:... | Nc1ccc2c(cnn2CCN2CCCC2)c1.O=C(O)CCc1ccc(Oc2ccccc2)cc1 | O=C(CCc1ccc(Oc2ccccc2)cc1)Nc1ccc2c(cnn2CCN2CCCC2)c1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CCc1ccc(Oc2ccccc2)cc1)Nc1ccc2c(cnn2CCN2CCCC2)c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | 1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-5-ylamine and 3-(4-phenoxy-phenyl)-propionic acid were processed as described in Example 17 to provide the title compound. 1H NMR (500 MHz, DMSO-D6) δ ppm 1.83 (m, 2 H), 1.99 (m, 2 H), 2.60 (t, J=7.64 Hz, 2 H), 2.87 (t, J=7.49 Hz, 2 H), 3.04 (m, 2 H), 3.52 (m, 2 H), 3.70 (m, 2 H),... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2n[nH]cc2c1.C1CC[NH]C1 | HO- | null | null | null | Nc1ccc2c(cnn2CCN2CCCC2)c1.O=C(O)CCc1ccc(Oc2ccccc2)cc1>>O=C(CCc1ccc(Oc2ccccc2)cc1)Nc1ccc2c(cnn2CCN2CCCC2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1bf38b74a639488cb0ac9055a78d6a29 | Nc1ccc2c(cnn2CCN2CCCC2)c1.O=C(O)Cc1cccc(Oc2ccccc2)c1>>O=C(Cc1cccc(Oc2ccccc2)c1)Nc1ccc2c(cnn2CCN2CCCC2)c1 | N1(CCCC1)CCN1N=CC2=CC(=CC=C12)N.O(C1=CC=CC=C1)C=1C=C(C=CC1)CC(=O)O>>O(C1=CC=CC=C1)C=1C=C(C=CC1)CC(=O)NC=1C=C2C=NN(C2=CC1)CCN1CCCC1 | [NH2:17][c:18]1[cH:19][cH:20][c:21]2[c:22]([cH:23][n:24][n:25]2[CH2:26][CH2:27][N:28]2[CH2:29][CH2:30][CH2:31][CH2:32]2)[cH:33]1.O[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([O:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16]1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([O:9][c:10]2[cH:11][cH:12][cH:13... | Nc1ccc2c(cnn2CCN2CCCC2)c1.O=C(O)Cc1cccc(Oc2ccccc2)c1 | O=C(Cc1cccc(Oc2ccccc2)c1)Nc1ccc2c(cnn2CCN2CCCC2)c1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Cc1cccc(Oc2ccccc2)c1)Nc1ccc2c(cnn2CCN2CCCC2)c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]-[c:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | 1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-5-ylamine and (3-phenoxy-phenyl)-acetic acid were processed as described in Example 17 to provide the title compound. MS (DCI/NH3) MS m/z 441 (M+H)+; 1H NMR (500 MHz, DMSO-d6) δ ppm 1.83 (m, 2 H), 1.99 (m, 2 H), 3.04 (m, 2 H), 3.52 (m, 2 H), 3.65 (s, 2 H), 3.71 (q, J=5.61 Hz, 2 H)... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2n[nH]cc2c1.C1CC[NH]C1 | HO- | null | null | null | Nc1ccc2c(cnn2CCN2CCCC2)c1.O=C(O)Cc1cccc(Oc2ccccc2)c1>>O=C(Cc1cccc(Oc2ccccc2)c1)Nc1ccc2c(cnn2CCN2CCCC2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3ef3fc7fddda436aac11ca8b93a4cf3d | Nc1ccc2c(cnn2CCN2CCCC2)c1.O=C(O)C1CCC(c2ccc(Cl)cc2)CC1>>O=C(Nc1ccc2c(cnn2CCN2CCCC2)c1)C1CCC(c2ccc(Cl)cc2)CC1 | N1(CCCC1)CCN1N=CC2=CC(=CC=C12)N.ClC1=CC=C(C=C1)C1CCC(CC1)C(=O)O>>ClC1=CC=C(C=C1)C1CCC(CC1)C(=O)NC=1C=C2C=NN(C2=CC1)CCN1CCCC1 | [NH2:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9][n:10][n:11]2[CH2:12][CH2:13][N:14]2[CH2:15][CH2:16][CH2:17][CH2:18]2)[cH:19]1.O[C:2](=[O:1])[CH:20]1[CH2:21][CH2:22][CH:23]([c:24]2[cH:25][cH:26][c:27]([Cl:28])[cH:29][cH:30]2)[CH2:31][CH2:32]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9][n:10][n:11]2[CH2:12][CH2:1... | Nc1ccc2c(cnn2CCN2CCCC2)c1.O=C(O)C1CCC(c2ccc(Cl)cc2)CC1 | O=C(Nc1ccc2c(cnn2CCN2CCCC2)c1)C1CCC(c2ccc(Cl)cc2)CC1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccc2c(cnn2CCN2CCCC2)c1)C1CCC(c2ccccc2)CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[C:5] | null | [] | null | null | null | null | 1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-5-ylamine and 4-(4-chloro-phenyl)-cyclohexanecarboxylic acid were processed as described in Example 17 to provide the title compound. MS (DCI/NH3) MS m/z 451 (M+H)+; 1H NMR (500 MHz, DMSO-d6) δ ppm 1.48 (m, 2 H), 1.64 (m, 2 H), 1.75–2.06 (m, 8 H), 2.42 (m, 1 H), 2.57 (m, 1 H), 3.0... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2n[nH]cc2c1.C1CC[NH]C1.C1CCCCC1.c1ccccc1 | HO- | null | null | null | Nc1ccc2c(cnn2CCN2CCCC2)c1.O=C(O)C1CCC(c2ccc(Cl)cc2)CC1>>O=C(Nc1ccc2c(cnn2CCN2CCCC2)c1)C1CCC(c2ccc(Cl)cc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2eb587e5149e480989fdf50dc4ae3424 | Nc1ccc2c(cnn2CCN2CCCC2)c1.O=C(O)CCc1ccc(Oc2ccccc2)cc1>>O=C(CCc1ccc(Oc2ccccc2)cc1)Nc1ccc2c(cnn2CCN2CCCC2)c1 | N1(CCCC1)CCN1N=CC2=CC(=CC=C12)N.O(C1=CC=CC=C1)C1=CC=C(C=C1)CCC(=O)O>>O(C1=CC=CC=C1)C1=CC=C(C=C1)CCC(=O)NC=1C=C2C=NN(C2=CC1)CCN1CCCC1 | [NH2:18][c:19]1[cH:20][cH:21][c:22]2[c:23]([cH:24][n:25][n:26]2[CH2:27][CH2:28][N:29]2[CH2:30][CH2:31][CH2:32][CH2:33]2)[cH:34]1.O[C:2](=[O:1])[CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([O:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][cH:17]1>>[O:1]=[C:2]([CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([O:9][c:10]2[cH:11][cH:... | Nc1ccc2c(cnn2CCN2CCCC2)c1.O=C(O)CCc1ccc(Oc2ccccc2)cc1 | O=C(CCc1ccc(Oc2ccccc2)cc1)Nc1ccc2c(cnn2CCN2CCCC2)c1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CCc1ccc(Oc2ccccc2)cc1)Nc1ccc2c(cnn2CCN2CCCC2)c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | 1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-5-ylamine and 3-(4-phenoxy-phenyl)-propionic acid were processed as described in Example 17 to provide the title compound. MS (DCI/NH3) MS m/z 455 (M+H)+; 1H NMR (500 MHz, DMSO-d6) δ ppm 1.83 (m, 2 H), 1.99 (m, 2 H), 2.79 (t, J=7.64 Hz, 2 H), 2.96 (t, J=7.49 Hz, 2 H), 3.06 (m, 2 H... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2n[nH]cc2c1.C1CC[NH]C1 | HO- | null | null | null | Nc1ccc2c(cnn2CCN2CCCC2)c1.O=C(O)CCc1ccc(Oc2ccccc2)cc1>>O=C(CCc1ccc(Oc2ccccc2)cc1)Nc1ccc2c(cnn2CCN2CCCC2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3763547a8e024b02a24fe89fa320978c | Nc1ccc2c(cnn2CCN2CCCC2)c1.O=C(O)Cc1ccc(Oc2ccccc2)cc1>>O=C(Cc1ccc(Oc2ccccc2)cc1)Nc1ccc2c(cnn2CCN2CCCC2)c1 | N1(CCCC1)CCN1N=CC2=CC(=CC=C12)N.O(C1=CC=CC=C1)C1=CC=C(C=C1)CC(=O)O>>O(C1=CC=CC=C1)C1=CC=C(C=C1)CC(=O)NC=1C=C2C=NN(C2=CC1)CCN1CCCC1 | [NH2:17][c:18]1[cH:19][cH:20][c:21]2[c:22]([cH:23][n:24][n:25]2[CH2:26][CH2:27][N:28]2[CH2:29][CH2:30][CH2:31][CH2:32]2)[cH:33]1.O[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15][cH:16]1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][cH:12][cH:13... | Nc1ccc2c(cnn2CCN2CCCC2)c1.O=C(O)Cc1ccc(Oc2ccccc2)cc1 | O=C(Cc1ccc(Oc2ccccc2)cc1)Nc1ccc2c(cnn2CCN2CCCC2)c1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Cc1ccc(Oc2ccccc2)cc1)Nc1ccc2c(cnn2CCN2CCCC2)c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]-[c:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | 1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-5-ylamine and (4-phenoxy-phenyl)-acetic acid were processed as described in Example 17 to provide the title compound. MS (DCI/NH3) MS m/z 441 (M+H)+; 1H NMR (500 MHz, DMSO-d6) δ ppm 1.83 (m, 2 H), 1.99 (m, 2 H), 3.05 (m, 2 H), 3.52 (m, 2 H), 3.65 (s, 2 H), 3.71 (q, J=5.93 Hz, 2 H)... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2n[nH]cc2c1.C1CC[NH]C1 | HO- | null | null | null | Nc1ccc2c(cnn2CCN2CCCC2)c1.O=C(O)Cc1ccc(Oc2ccccc2)cc1>>O=C(Cc1ccc(Oc2ccccc2)cc1)Nc1ccc2c(cnn2CCN2CCCC2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9d6c0d884bcc4bc0ba574d7ce4f212d5 | Nc1ccc2c(cnn2CCN2CCCC2)c1.O=C(O)C=Cc1ccc(-c2ccccc2)cc1>>O=C(/C=C/c1ccc(-c2ccccc2)cc1)Nc1ccc2c(cnn2CCN2CCCC2)c1 | N1(CCCC1)CCN1N=CC2=CC(=CC=C12)N.C1(=CC=C(C=C1)C=CC(=O)O)C1=CC=CC=C1>>C1(=CC=C(C=C1)/C=C/C(=O)NC=1C=C2C=NN(C2=CC1)CCN1CCCC1)C1=CC=CC=C1 | [NH2:17][c:18]1[cH:19][cH:20][c:21]2[c:22]([cH:23][n:24][n:25]2[CH2:26][CH2:27][N:28]2[CH2:29][CH2:30][CH2:31][CH2:32]2)[cH:33]1.O[C:2](=[O:1])[CH:3]=[CH: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>>[O:1]=[C:2](/[CH:3]=[CH:4]/[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12]... | Nc1ccc2c(cnn2CCN2CCCC2)c1.O=C(O)C=Cc1ccc(-c2ccccc2)cc1 | O=C(/C=C/c1ccc(-c2ccccc2)cc1)Nc1ccc2c(cnn2CCN2CCCC2)c1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(/C=C/c1ccc(-c2ccccc2)cc1)Nc1ccc2c(cnn2CCN2CCCC2)c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C:4]-[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](/[C:3]=[C:4]/[c:5])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | null | [] | null | null | null | null | 1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-5-ylamine and 3-biphenyl-4-yl-acrylic acid were processed as described in Example 17 to provide the title compound. MS (DCI/NH3) MS m/z 437 (M+H)+; 1H NMR (500 MHz, DMSO-d6) δ ppm 1.84 (m, 2 H), 1.99 (m, 2 H), 3.06 (m, 2 H), 3.53 (m, 2 H), 3.72 (m, 2 H), 4.76 (t, J=5.93 Hz, 2 H), ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2n[nH]cc2c1.C1CC[NH]C1 | HO- | null | null | null | Nc1ccc2c(cnn2CCN2CCCC2)c1.O=C(O)C=Cc1ccc(-c2ccccc2)cc1>>O=C(/C=C/c1ccc(-c2ccccc2)cc1)Nc1ccc2c(cnn2CCN2CCCC2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5ee0f7c74eb045949bb2ca2b5cb79163 | Nc1ccc2c(c1)CN(CCN1CCCC1)N2.O=C=Nc1ccc(Oc2ccccc2)cc1>>O=C(Nc1ccc(Oc2ccccc2)cc1)Nc1ccc2c(cnn2CCN2CCCC2)c1 | N1(CCCC1)CCN1NC2=CC=C(C=C2C1)N.O(C1=CC=CC=C1)C1=CC=C(C=C1)N=C=O>>O(C1=CC=CC=C1)C1=CC=C(C=C1)NC(=O)NC=1C=C2C=NN(C2=CC1)CCN1CCCC1 | [NH2:17][c:18]1[cH:19][cH:20][c:21]2[c:22]([cH:33]1)[CH2:23][N:24]([CH2:26][CH2:27][N:28]1[CH2:29][CH2:30][CH2:31][CH2:32]1)[NH:25]2.[O:1]=[C:2]=[N:3][c:4]1[cH:5][cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15][cH:16]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][cH:12][cH:13]... | Nc1ccc2c(c1)CN(CCN1CCCC1)N2.O=C=Nc1ccc(Oc2ccccc2)cc1 | O=C(Nc1ccc(Oc2ccccc2)cc1)Nc1ccc2c(cnn2CCN2CCCC2)c1 | null | null | C1CCOC1 | Acylation | OtherReaction | 1be10657bfe899d07da4874e35dc1d5237ed9413c60547ab0c62b6289b2000b4 | ec59a3886483e9a92168c3249374ddc9c96621e5e1ddf6f6e1e6ff1217cfee5f | O=C(Nc1ccc(Oc2ccccc2)cc1)Nc1ccc2c(cnn2CCN2CCCC2)c1 | [#7:1]-[C:2]-[CH2;D2;+0:3]-[N;H0;D3;+0:4]1-[CH2;D2;+0:5]-[c:6]2:[c:7]:[c:8](-[NH2;D1;+0:9]):[c:10]:[c:11]:[c:12]:2-[NH;D2;+0:13]-1.[O;D1;H0:14]=[C;H0;D2;+0:15]=[N;H0;D2;+0:16]-[c:17](:[c:18]):[c:19]>>[#7:1]-[C:2]-[CH2;D2;+0:3]-[n;H0;D3;+0:13]1:[n;H0;D2;+0:4]:[cH;D2;+0:5]:[c:6]2:[c:7]:[c:8](-[NH;D2;+0:9]-[C;H0;D3;+0:15]... | null | [] | 50 | CELSIUS | 1 | HOUR | A mixture of 2-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-5-ylamine (0.100 g, 0.434 mmol) and 4-phenoxyphenyl isocyanate (0.0917 g, 0.434 mmol) in 6 mL of THF was stirred at 50° C. for 1 hour, cooled to room temperature and concentrated under reduced pressure. The residue was triturated in diethyl ether and collected by filt... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Isocyanate.Primary amine | Urea | c1ccc2c(c1)C[NH]N2 | c1ccc2n[nH]cc2c1 | c1ccccc1.c1ccccc1.c1ccc2n[nH]cc2c1.C1CC[NH]C1 | null | C1CCOC1 | 50 | 1 | Nc1ccc2c(c1)CN(CCN1CCCC1)N2.O=C=Nc1ccc(Oc2ccccc2)cc1>C1CCOC1>O=C(Nc1ccc(Oc2ccccc2)cc1)Nc1ccc2c(cnn2CCN2CCCC2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b726e01817984974ba9b23a2f9838f16 | Nc1ccc2c(cnn2CCN2CCCC2)c1.O=C=Nc1ccc([N+](=O)[O-])cc1>>O=C(Nc1ccc([N+](=O)[O-])cc1)Nc1ccc2c(cnn2CCN2CCCC2)c1 | N1(CCCC1)CCN1N=CC2=CC(=CC=C12)N.[N+](=O)([O-])C1=CC=C(C=C1)N=C=O>>[N+](=O)([O-])C1=CC=C(C=C1)NC(=O)NC=1C=C2C=NN(C2=CC1)CCN1CCCC1 | [NH2:13][c:14]1[cH:15][cH:16][c:17]2[c:18]([cH:19][n:20][n:21]2[CH2:22][CH2:23][N:24]2[CH2:25][CH2:26][CH2:27][CH2:28]2)[cH:29]1.[O:1]=[C:2]=[N:3][c:4]1[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12]1)[NH:13][c:14]1[cH:15][cH:16][c:... | Nc1ccc2c(cnn2CCN2CCCC2)c1.O=C=Nc1ccc([N+](=O)[O-])cc1 | O=C(Nc1ccc([N+](=O)[O-])cc1)Nc1ccc2c(cnn2CCN2CCCC2)c1 | null | null | C1CCOC1 | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(Nc1ccccc1)Nc1ccc2c(cnn2CCN2CCCC2)c1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C;H0;D2;+0:6]=[N;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:5]=[C;H0;D3;+0:6](-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | 91 | [{"value": 91.0, "product": "[N+](=O)([O-])C1=CC=C(C=C1)NC(=O)NC=1C=C2C=NN(C2=CC1)CCN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.3, "product": "[N+](=O)([O-])C1=CC=C(C=C1)NC(=O)NC=1C=C2C=NN(C2=CC1)CCN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-5-ylamine (2.0 g, 8.7 mmol) and 4-nitrophenyl isocyanate (1.5 g, 8.8 mmol) in 150 mL of THF was heated to reflux for 2 hours. The solution was cooled to room temperature and concentrated under reduced pressure. The residue was taken up in 100 mL of ethyl acetate and t... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1ccc2n[nH]cc2c1.C1CC[NH]C1 | null | C1CCOC1 | null | null | Nc1ccc2c(cnn2CCN2CCCC2)c1.O=C=Nc1ccc([N+](=O)[O-])cc1>C1CCOC1>O=C(Nc1ccc([N+](=O)[O-])cc1)Nc1ccc2c(cnn2CCN2CCCC2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-920c090f688e43ef88254625b1663b53 | O=C(Nc1ccc([N+](=O)[O-])cc1)Nc1ccc2c(cnn2CCN2CCCC2)c1>>Nc1ccc(NC(=O)Nc2ccc3c(cnn3CCN3CCCC3)c2)cc1 | [N+](=O)([O-])C1=CC=C(C=C1)NC(=O)NC=1C=C2C=NN(C2=CC1)CCN1CCCC1.[Cl-].[NH4+]>>NC1=CC=C(C=C1)NC(=O)NC=1C=C2C=NN(C2=CC1)CCN1CCCC1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([NH:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][c:13]3[c:14]([cH:15][n:16][n:17]3[CH2:18][CH2:19][N:20]3[CH2:21][CH2:22][CH2:23][CH2:24]3)[cH:25]2)[cH:26][cH:27]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([NH:6][C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][c:13]3[c:14]([cH:15][n:16][n:17]3[CH2:18]... | O=C(Nc1ccc([N+](=O)[O-])cc1)Nc1ccc2c(cnn2CCN2CCCC2)c1 | Nc1ccc(NC(=O)Nc2ccc3c(cnn3CCN3CCCC3)c2)cc1 | null | [Fe] | C(C)O.O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(Nc1ccccc1)Nc1ccc2c(cnn2CCN2CCCC2)c1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 92 | [{"value": 92.0, "product": "NC1=CC=C(C=C1)NC(=O)NC=1C=C2C=NN(C2=CC1)CCN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.5, "product": "NC1=CC=C(C=C1)NC(=O)NC=1C=C2C=NN(C2=CC1)CCN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A mixture of 1-(4-nitro-phenyl)-3-[1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-5-yl]-urea (3.1 g, 7.8 mmol), iron powder (3.5 g, 63 mmol), and ammonium chloride (0.21 g, 3.9 mmol) in a 4:1 ethanol/H2O solution (50 mL) was heated to reflux for 3 hours, cooled to room temperature and concentrated under reduced pressure. The r... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccc2n[nH]cc2c1.C1CC[NH]C1 | Other | [Fe].C(C)O.O | null | 0.25 | O=C(Nc1ccc([N+](=O)[O-])cc1)Nc1ccc2c(cnn2CCN2CCCC2)c1>[Fe].C(C)O.O>Nc1ccc(NC(=O)Nc2ccc3c(cnn3CCN3CCCC3)c2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0590c53c710a46c583c6eb7ed098bd48 | Nc1ccc(NC(=O)Nc2ccc3c(cnn3CCN3CCCC3)c2)cc1.OB(O)c1ccccc1>>O=C(Nc1ccc(Nc2ccccc2)cc1)Nc1ccc2c(cnn2CCN2CCCC2)c1 | NC1=CC=C(C=C1)NC(=O)NC=1C=C2C=NN(C2=CC1)CCN1CCCC1.C1(=CC=CC=C1)B(O)O.C(C)N(CC)CC>>C1(=CC=CC=C1)NC1=CC=C(C=C1)NC(=O)NC=1C=C2C=NN(C2=CC1)CCN1CCCC1 | [O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([NH2:8])[cH:15][cH:16]1)[NH:17][c:18]1[cH:19][cH:20][c:21]2[c:22]([cH:23][n:24][n:25]2[CH2:26][CH2:27][N:28]2[CH2:29][CH2:30][CH2:31][CH2:32]2)[cH:33]1.OB(O)[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[cH:10][cH:11][cH:12][c... | Nc1ccc(NC(=O)Nc2ccc3c(cnn3CCN3CCCC3)c2)cc1.OB(O)c1ccccc1 | O=C(Nc1ccc(Nc2ccccc2)cc1)Nc1ccc2c(cnn2CCN2CCCC2)c1 | null | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-] | ClCCl | Heteroatom Alkylation and Arylation | Petasis reaction with amines and boronic acids | f5ae67a51de553a156f239a36ff1b30b0ec21b32d6467ebb95abe227e16748df | e74ce03b343a41c63fb42720bde3cd7e68ada25a9dc3f3bcf817625520d2a637 | O=C(Nc1ccc(Nc2ccccc2)cc1)Nc1ccc2c(cnn2CCN2CCCC2)c1 | O-B(-O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[c:4]:[c:5] | 45.4 | [{"value": 45.0, "product": "C1(=CC=CC=C1)NC1=CC=C(C=C1)NC(=O)NC=1C=C2C=NN(C2=CC1)CCN1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.4, "product": "C1(=CC=CC=C1)NC1=CC=C(C=C1)NC(=O)NC=1C=C2C=NN(C2=CC1)CCN1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1-(4-amino-phenyl)-3-[1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-5-yl]-urea (364 mg, 1 mmol), phenylboronic acid (244 mg, 2 mmol), copper(II) acetate (364 mg, 2 mmol), triethylamine (0.2 mL, 2 mmol), in 20 mL of dichloromethane was refluxed overnight. The mixture was concentrated under reduced pressure and the... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Boronic acid | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2n[nH]cc2c1.C1CC[NH]C1 | HO-.B | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].ClCCl | null | null | Nc1ccc(NC(=O)Nc2ccc3c(cnn3CCN3CCCC3)c2)cc1.OB(O)c1ccccc1>C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].ClCCl>O=C(Nc1ccc(Nc2ccccc2)cc1)Nc1ccc2c(cnn2CCN2CCCC2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b75410c34124417cb5d6dff5f531fe63 | CN(C)CCCl.O=[N+]([O-])c1ccc2[nH]ncc2c1>>CN(C)CCn1ncc2cc([N+](=O)[O-])ccc21 | [N+](=O)([O-])C=1C=C2C=NNC2=CC1.C([O-])([O-])=O.[K+].[K+].Cl.CN(CCCl)C>>CN(CCN1N=CC2=CC(=CC=C12)[N+](=O)[O-])C | Cl[CH2:5][CH2:4][N:2]([CH3:1])[CH3:3].[nH:6]1[n:7][cH:8][c:9]2[cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16][c:17]12>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][n:6]1[n:7][cH:8][c:9]2[cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16][c:17]12 | CN(C)CCCl.O=[N+]([O-])c1ccc2[nH]ncc2c1 | CN(C)CCn1ncc2cc([N+](=O)[O-])ccc21 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 02281da08c2e04758fd450b7651d9c90a4717fd45f9df9992c90324816997d62 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc2[nH]ncc2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[c:4]:[c:5]1:[c:6]:[c:7]:[#7;a:8]:[nH;D2;+0:9]:1>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:9]1:[#7;a:8]:[c:7]:[c:6]:[c:5]:1:[c:4] | 64 | [{"value": 64.0, "product": "CN(CCN1N=CC2=CC(=CC=C12)[N+](=O)[O-])C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.0, "product": "CN(CCN1N=CC2=CC(=CC=C12)[N+](=O)[O-])C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | A mixture of 5-nitroindazole (2 g, 12 mmol) and potassium carbonate (5.1 g 37 mmol) in DMF (40 mL) was stirred for 30 minutes after which 2-(dimethylamino)ethylchloride hydrochloride (2.65 g 18.4 mmol) was added. The mixture was heated to 60° C. for 6 hours, cooled to room temperature and was filtered through a plug of... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ncc2c1 | c1ccc2[nH]ncc2c1 | c1ccc2[nH]ncc2c1 | HCl | CN(C)C=O | 60 | null | CN(C)CCCl.O=[N+]([O-])c1ccc2[nH]ncc2c1>CN(C)C=O>CN(C)CCn1ncc2cc([N+](=O)[O-])ccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ab0730f109964f06a3623f53a593e2b4 | CN(C)CCn1ncc2cc([N+](=O)[O-])ccc21>>CN(C)CCn1ncc2cc(N)ccc21 | CN(CCN1N=CC2=CC(=CC=C12)[N+](=O)[O-])C.[Cl-].[NH4+]>>CN(CCN1N=CC2=CC(=CC=C12)N)C | O=[N+:12]([O-])[c:11]1[cH:10][c:9]2[cH:8][n:7][n:6]([CH2:5][CH2:4][N:2]([CH3:1])[CH3:3])[c:15]2[cH:14][cH:13]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][n:6]1[n:7][cH:8][c:9]2[cH:10][c:11]([NH2:12])[cH:13][cH:14][c:15]12 | CN(C)CCn1ncc2cc([N+](=O)[O-])ccc21 | CN(C)CCn1ncc2cc(N)ccc21 | null | [Fe] | C(C)O.O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2[nH]ncc2c1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 92 | [{"value": 92.0, "product": "CN(CCN1N=CC2=CC(=CC=C12)N)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.1, "product": "CN(CCN1N=CC2=CC(=CC=C12)N)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A mixture of dimethyl-[2-(5-nitro-indazol-1-yl)-ethyl]-amine (1 g, 4.3 mmol), iron powder (1.9 g, 34 mmol), and ammonium chloride (120 mg, 2.2 mmol) in a 4:1 ethanol/H2O solution (20 mL) was heated to reflux for 3 hours, cooled to room temperature and concentrated under reduced pressure. The residue was stirred in trie... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2[nH]ncc2c1 | Other | [Fe].C(C)O.O | null | 0.25 | CN(C)CCn1ncc2cc([N+](=O)[O-])ccc21>[Fe].C(C)O.O>CN(C)CCn1ncc2cc(N)ccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7eb8b8c43000454c814853505123ccb8 | CN(C)CCn1ncc2cc(N)ccc21.O=C(O)Cc1ccc(Oc2ccccc2)cc1>>CN(C)CCn1ncc2cc(NC(=O)Cc3ccc(Oc4ccccc4)cc3)ccc21 | CN(CCN1N=CC2=CC(=CC=C12)N)C.O(C1=CC=CC=C1)C1=CC=C(C=C1)CC(=O)O.Cl.C(C)N=C=NC(CC)(C)C.ON1N=NC2=C1C=CC=C2.CN1CCOCC1>>CN(CCN1N=CC2=CC(=CC=C12)NC(CC1=CC=C(C=C1)OC1=CC=CC=C1)=O)C | [CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][n:6]1[n:7][cH:8][c:9]2[cH:10][c:11]([NH2:12])[cH:29][cH:30][c:31]12.O[C:13](=[O:14])[CH2:15][c:16]1[cH:17][cH:18][c:19]([O:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[cH:27][cH:28]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][n:6]1[n:7][cH:8][c:9]2[cH:10][c:11]([NH:12][C:13](=[O:14])[CH... | CN(C)CCn1ncc2cc(N)ccc21.O=C(O)Cc1ccc(Oc2ccccc2)cc1 | CN(C)CCn1ncc2cc(NC(=O)Cc3ccc(Oc4ccccc4)cc3)ccc21 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Cc1ccc(Oc2ccccc2)cc1)Nc1ccc2[nH]ncc2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]-[c:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | 6 | HOUR | A mixture of 1-(2-dimethylamino-ethyl)-1H-indazol-5-ylamine (42 mg, 0.20 mmol), 4-phenoxy-phenylacetic acid (47 mg, 0.21 mmol), ethyldimethylpropylcarbodiimide hydrochloride (43 mg g, 0.22 mmol), N-hydroxybenzotriazole (30 mg, 0.22 mmol), N-methyl morpholine (46 mg, 0.44 mmol) in 2 mL of DMF was shaken for 6 hours. The... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2[nH]ncc2c1.c1ccccc1.c1ccccc1 | HO- | CN(C)C=O | null | 6 | CN(C)CCn1ncc2cc(N)ccc21.O=C(O)Cc1ccc(Oc2ccccc2)cc1>CN(C)C=O>CN(C)CCn1ncc2cc(NC(=O)Cc3ccc(Oc4ccccc4)cc3)ccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-86181e1da498497389831caf81c5c3cb | CN(C)CCn1ncc2cc(N)ccc21.O=C=Nc1ccc(Oc2ccccc2)cc1>>CN(C)CCn1ncc2cc(NC(=O)Nc3ccc(Oc4ccccc4)cc3)ccc21 | CN(CCN1N=CC2=CC(=CC=C12)N)C.O(C1=CC=CC=C1)C1=CC=C(C=C1)N=C=O>>CN(CCN1N=CC2=CC(=CC=C12)NC(=O)NC1=CC=C(C=C1)OC1=CC=CC=C1)C | [CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][n:6]1[n:7][cH:8][c:9]2[cH:10][c:11]([NH2:12])[cH:29][cH:30][c:31]12.[C:13](=[O:14])=[N:15][c:16]1[cH:17][cH:18][c:19]([O:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[cH:27][cH:28]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][n:6]1[n:7][cH:8][c:9]2[cH:10][c:11]([NH:12][C:13](=[O:14])[NH:1... | CN(C)CCn1ncc2cc(N)ccc21.O=C=Nc1ccc(Oc2ccccc2)cc1 | CN(C)CCn1ncc2cc(NC(=O)Nc3ccc(Oc4ccccc4)cc3)ccc21 | null | null | C1CCOC1 | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(Nc1ccc(Oc2ccccc2)cc1)Nc1ccc2[nH]ncc2c1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C;H0;D2;+0:6]=[N;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:5]=[C;H0;D3;+0:6](-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | null | [] | 50 | CELSIUS | null | null | A mixture of 1-(2-dimethylamino-ethyl)-1H-indazol-5-ylamine (42 mg, 0.17 mmol), 4-phenoxyphenyl isocyanate (36 mg, 0.17 mmol) in 2 mL of THF was heated to 50° C. for 6 hours, cool to room temperature and concentrated under reduced pressure. The residue was dissolved in 1.5 mL of a 1:1 mixture of dimethyl sulfoxide/meth... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccc2[nH]ncc2c1.c1ccccc1.c1ccccc1 | null | C1CCOC1 | 50 | null | CN(C)CCn1ncc2cc(N)ccc21.O=C=Nc1ccc(Oc2ccccc2)cc1>C1CCOC1>CN(C)CCn1ncc2cc(NC(=O)Nc3ccc(Oc4ccccc4)cc3)ccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cfc872f545334002b7cc706c5cd6d8bf | ClCCN1CCCCC1.O=[N+]([O-])c1ccc2[nH]ncc2c1>>O=[N+]([O-])c1ccc2c(cnn2CCN2CCCCC2)c1 | [N+](=O)([O-])C=1C=C2C=NNC2=CC1.C([O-])([O-])=O.[K+].[K+].Cl.ClCCN1CCCCC1>>[N+](=O)([O-])C=1C=C2C=NN(C2=CC1)CCN1CCCCC1 | Cl[CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1.[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9][n:10][nH:11]2)[cH:20]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9][n:10][n:11]2[CH2:12][CH2:13][N:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[cH:20]1 | ClCCN1CCCCC1.O=[N+]([O-])c1ccc2[nH]ncc2c1 | O=[N+]([O-])c1ccc2c(cnn2CCN2CCCCC2)c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 1c9bfadcc8b17ce33571db0aba6fe4d2adf28d49d529bcf12a641e342e01b0dc | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc2c(c1)cnn2CCN1CCCCC1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[c:4]:[c:5]1:[c:6]:[c:7]:[#7;a:8]:[nH;D2;+0:9]:1>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:9]1:[#7;a:8]:[c:7]:[c:6]:[c:5]:1:[c:4] | 65.3 | [{"value": 64.0, "product": "[N+](=O)([O-])C=1C=C2C=NN(C2=CC1)CCN1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.3, "product": "[N+](=O)([O-])C=1C=C2C=NN(C2=CC1)CCN1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | A mixture of 5-nitroindazole (4.0 g, 24 mmol) and potassium carbonate (10 g 74 mmol) in DMF (60 mL) was stirred for 30 minutes after which 1-(2-chloro-ethyl)-piperidine hydrochloride (6.8 g 37 mmol) was added. The mixture was heated to 60° C. for 6 hours, cooled to room temperature and filtered through a plug of silica... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2n[nH]cc2c1 | c1ccc2n[nH]cc2c1 | c1ccc2n[nH]cc2c1.C1CC[NH]CC1 | HCl | CN(C)C=O | 60 | null | ClCCN1CCCCC1.O=[N+]([O-])c1ccc2[nH]ncc2c1>CN(C)C=O>O=[N+]([O-])c1ccc2c(cnn2CCN2CCCCC2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a1e8f338515341c5b9013f5d60ce2d31 | O=[N+]([O-])c1ccc2c(cnn2CCN2CCCCC2)c1>>Nc1ccc2c(cnn2CCN2CCCCC2)c1 | [N+](=O)([O-])C=1C=C2C=NN(C2=CC1)CCN1CCCCC1.[Cl-].[NH4+]>>N1(CCCCC1)CCN1N=CC2=CC(=CC=C12)N | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7][n:8][n:9]2[CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[cH:18]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7][n:8][n:9]2[CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[cH:18]1 | O=[N+]([O-])c1ccc2c(cnn2CCN2CCCCC2)c1 | Nc1ccc2c(cnn2CCN2CCCCC2)c1 | null | [Fe] | C(C)O.O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2c(c1)cnn2CCN1CCCCC1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 93 | [{"value": 93.0, "product": "N1(CCCCC1)CCN1N=CC2=CC(=CC=C12)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.0, "product": "N1(CCCCC1)CCN1N=CC2=CC(=CC=C12)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A mixture of 5-nitro-1-(2-piperidin-1-yl-ethyl)-1H-indazole (4.3 g, 16 mmol), iron powder (8.8 g, 157 mmol), and ammonium chloride (430 mg, 8 mmol) in a 4:1 ethanol/H2O solution (75 mL) was heated to reflux for 3 hours, cooled to room temperature and concentrated under reduced pressure. The residue was stirred in triet... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2n[nH]cc2c1.C1CC[NH]CC1 | Other | [Fe].C(C)O.O | null | 0.25 | O=[N+]([O-])c1ccc2c(cnn2CCN2CCCCC2)c1>[Fe].C(C)O.O>Nc1ccc2c(cnn2CCN2CCCCC2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-031ab4cec54c4ac7b7426df82ead85cd | O=[N+]([O-])c1ccc2c(cnn2CCN2CCOCC2)c1>>Nc1ccc2c(cnn2CCN2CCOCC2)c1 | N1(CCOCC1)CCN1N=CC2=CC(=CC=C12)[N+](=O)[O-].[Cl-].[NH4+]>>N1(CCOCC1)CCN1N=CC2=CC(=CC=C12)N | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7][n:8][n:9]2[CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)[cH:18]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7][n:8][n:9]2[CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)[cH:18]1 | O=[N+]([O-])c1ccc2c(cnn2CCN2CCOCC2)c1 | Nc1ccc2c(cnn2CCN2CCOCC2)c1 | null | [Fe] | C(C)O.O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2c(c1)cnn2CCN1CCOCC1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 93 | [{"value": 93.0, "product": "N1(CCOCC1)CCN1N=CC2=CC(=CC=C12)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.3, "product": "N1(CCOCC1)CCN1N=CC2=CC(=CC=C12)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A mixture of 1-(2-morpholin-4-yl-ethyl)-5-nitro-1H-indazole (4.3 g, 16 mmol), iron powder (8.8 g, 157 mmol), and ammonium chloride (430 mg, 8 mmol) in a 4:1 ethanol/H2O solution (75 mL) was heated to reflux for 3 hours, cooled to room temperature and concentrated under reduced pressure. The residue was taken up and sti... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2n[nH]cc2c1.C1COCC[NH]1 | Other | [Fe].C(C)O.O | null | 0.25 | O=[N+]([O-])c1ccc2c(cnn2CCN2CCOCC2)c1>[Fe].C(C)O.O>Nc1ccc2c(cnn2CCN2CCOCC2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f46c721654e54331946496b18bc9053b | COC(CBr)OC.O=[N+]([O-])c1ccc2[nH]ncc2c1>>COC(Cn1ncc2cc([N+](=O)[O-])ccc21)OC | [N+](=O)([O-])C=1C=C2C=NNC2=CC1.C(=O)([O-])[O-].[K+].[K+].BrCC(OC)OC>>COC(CN1N=CC2=CC(=CC=C12)[N+](=O)[O-])OC | Br[CH2:4][CH:3]([O:2][CH3:1])[O:17][CH3:18].[nH:5]1[n:6][cH:7][c:8]2[cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14][cH:15][c:16]12>>[CH3:1][O:2][CH:3]([CH2:4][n:5]1[n:6][cH:7][c:8]2[cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14][cH:15][c:16]12)[O:17][CH3:18] | COC(CBr)OC.O=[N+]([O-])c1ccc2[nH]ncc2c1 | COC(Cn1ncc2cc([N+](=O)[O-])ccc21)OC | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 02281da08c2e04758fd450b7651d9c90a4717fd45f9df9992c90324816997d62 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc2[nH]ncc2c1 | Br-[CH2;D2;+0:1]-[C:2](-[#8:3])-[#8:4].[c:5]:[c:6]1:[c:7]:[c:8]:[#7;a:9]:[nH;D2;+0:10]:1>>[#8:3]-[C:2](-[#8:4])-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[#7;a:9]:[c:8]:[c:7]:[c:6]:1:[c:5] | 23.4 | [{"value": 23.4, "product": "COC(CN1N=CC2=CC(=CC=C12)[N+](=O)[O-])OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 55 | CELSIUS | null | null | To a stirred mixture of 3.00 g (18.4 mmol) of 5-nitroindazole and 5.08 g (36.9 mmol) of K2CO3 in 61 mL of DMF was slowly added 3.42 g (20.2 mmol) of 2-bromo-1,1-dimethoxy-ethane and the mixture heated to 55° C. for 12 hours. The mixture was cooled to room temperature, filtered through a bed of celite. The filtrate was ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ncc2c1 | c1ccc2[nH]ncc2c1 | c1ccc2[nH]ncc2c1 | HBr | CN(C)C=O | 55 | null | COC(CBr)OC.O=[N+]([O-])c1ccc2[nH]ncc2c1>CN(C)C=O>COC(Cn1ncc2cc([N+](=O)[O-])ccc21)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-edc9cfd6a4df4fe9967ad41e06d4cd7c | ClCCN1CCCC1.O=[N+]([O-])c1ccc2cn[nH]c2c1>>O=[N+]([O-])c1ccc2cnn(CCN3CCCC3)c2c1 | [N+](=O)([O-])C1=CC=C2C=NNC2=C1.C([O-])([O-])=O.[K+].[K+].Cl.ClCCN1CCCC1>>[N+](=O)([O-])C1=CC=C2C=NN(C2=C1)CCN1CCCC1 | Cl[CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][CH2:16][CH2:17]1.[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[cH:8][n:9][nH:10][c:18]2[cH:19]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[cH:8][n:9][n:10]([CH2:11][CH2:12][N:13]3[CH2:14][CH2:15][CH2:16][CH2:17]3)[c:18]2[cH:19]1 | ClCCN1CCCC1.O=[N+]([O-])c1ccc2cn[nH]c2c1 | O=[N+]([O-])c1ccc2cnn(CCN3CCCC3)c2c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 61b0a224b62ca0b743a21f455645a524e1404d8b5e8bd813e0a3f8c6a5539082 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc2c(c1)cnn2CCN1CCCC1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[c:4]:[c:5]1:[c:6]:[c:7]:[#7;a:8]:[nH;D2;+0:9]:1>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:9]1:[#7;a:8]:[c:7]:[c:6]:[c:5]:1:[c:4] | null | [] | 60 | CELSIUS | 30 | MINUTE | A mixture of 6-nitroindazole (2.00 g, 12.3 mmol) and potassium carbonate (5.10 g 37.0 mmol) in DMF (40 mL) was stirred for 30 minutes, after which 1-(2-chloro-ethyl)-pyrrolidine hydrochloride (3.20 g 18.9 mmol) was added. The mixture was heated to 60° C. for 6 hours, cooled to room temperature, filtered through a plug ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2n[nH]cc2c1 | c1ccc2c[nH]nc2c1 | c1ccc2c[nH]nc2c1.C1CC[NH]C1 | HCl | CN(C)C=O | 60 | 0.5 | ClCCN1CCCC1.O=[N+]([O-])c1ccc2cn[nH]c2c1>CN(C)C=O>O=[N+]([O-])c1ccc2cnn(CCN3CCCC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2d6d0e1abd944ea5bfa1cc44b1187f2d | O=[N+]([O-])c1ccc2cnn(CCN3CCCC3)c2c1>>Nc1ccc2cnn(CCN3CCCC3)c2c1 | [N+](=O)([O-])C1=CC=C2C=NN(C2=C1)CCN1CCCC1.[Cl-].[NH4+]>>N1(CCCC1)CCN1N=CC2=CC=C(C=C12)N | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]2[cH:6][n:7][n:8]([CH2:9][CH2:10][N:11]3[CH2:12][CH2:13][CH2:14][CH2:15]3)[c:16]2[cH:17]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][n:7][n:8]([CH2:9][CH2:10][N:11]3[CH2:12][CH2:13][CH2:14][CH2:15]3)[c:16]2[cH:17]1 | O=[N+]([O-])c1ccc2cnn(CCN3CCCC3)c2c1 | Nc1ccc2cnn(CCN3CCCC3)c2c1 | null | [Fe] | C(C)O.O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2c(c1)cnn2CCN1CCCC1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | null | [] | null | null | 15 | MINUTE | A mixture of 6-nitro-1-(2-pyrrolidin-1-yl-ethyl)-1H-indazole (1.60 g, 6.15 mmol), iron powder (3.40 g, 60.8 mmol), and ammonium chloride (166 mg, 3.13 mmol) in a 4:1 solution of ethanol/H2O was heated to reflux for 3 hours, cooled to room temperature, concentrated under reduced pressure. The residue was stirred in trie... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2c[nH]nc2c1.C1CC[NH]C1 | Other | [Fe].C(C)O.O | null | 0.25 | O=[N+]([O-])c1ccc2cnn(CCN3CCCC3)c2c1>[Fe].C(C)O.O>Nc1ccc2cnn(CCN3CCCC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7df9f99af20b46018cd803d40e6ad47b | Nc1ccc2cnn(CCN3CCCC3)c2c1.O=C(O)Cc1ccc(OCc2ccccc2)cc1>>O=C(Cc1ccc(OCc2ccccc2)cc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 | N1(CCCC1)CCN1N=CC2=CC=C(C=C12)N.C(C1=CC=CC=C1)OC1=CC=C(C=C1)CC(=O)O.Cl.C(C)N=C=NC(CC)(C)C.ON1N=NC2=C1C=CC=C2.CN1CCOCC1>>C(C1=CC=CC=C1)OC1=CC=C(C=C1)CC(=O)NC1=CC=C2C=NN(C2=C1)CCN1CCCC1 | [NH2:18][c:19]1[cH:20][cH:21][c:22]2[cH:23][n:24][n:25]([CH2:26][CH2:27][N:28]3[CH2:29][CH2:30][CH2:31][CH2:32]3)[c:33]2[cH:34]1.O[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][cH:17]1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:... | Nc1ccc2cnn(CCN3CCCC3)c2c1.O=C(O)Cc1ccc(OCc2ccccc2)cc1 | O=C(Cc1ccc(OCc2ccccc2)cc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Cc1ccc(OCc2ccccc2)cc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[#7;a:5]:[c:6]:[c:7]:[c:8](-[NH2;D1;+0:9]):[c:10]>>[#7;a:5]:[c:6]:[c:7]:[c:8](-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]):[c:10] | null | [] | null | null | 6 | HOUR | A mixture of 1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-6-ylamine (48 mg, 0.21 mmol), (4-benzyloxy-phenyl)-acetic acid (50 mg, 0.21 mmol), ethyldimethylpropylcarbodiimide hydrochloride (47 mg g, 0.25 mmol), N-hydroxybenzotriazole (33 mg, 0.25 mmol), N-methyl morpholine (50 mg, 0.50 mmol) in 2 mL of DMF was shaken for 6 hou... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c[nH]nc2c1.C1CC[NH]C1 | HO- | CN(C)C=O | null | 6 | Nc1ccc2cnn(CCN3CCCC3)c2c1.O=C(O)Cc1ccc(OCc2ccccc2)cc1>CN(C)C=O>O=C(Cc1ccc(OCc2ccccc2)cc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c1b40672e9364bf7ade1762da79c3923 | Nc1ccc2cnn(CCN3CCCC3)c2c1.O=C(O)Cc1cccc(Oc2ccccc2)c1>>O=C(Cc1cccc(Oc2ccccc2)c1)Nc1ccc2cnn(CCN3CCCC3)c2c1 | N1(CCCC1)CCN1N=CC2=CC=C(C=C12)N.O(C1=CC=CC=C1)C=1C=C(C=CC1)CC(=O)O>>O(C1=CC=CC=C1)C=1C=C(C=CC1)CC(=O)NC1=CC=C2C=NN(C2=C1)CCN1CCCC1 | [NH2:17][c:18]1[cH:19][cH:20][c:21]2[cH:22][n:23][n:24]([CH2:25][CH2:26][N:27]3[CH2:28][CH2:29][CH2:30][CH2:31]3)[c:32]2[cH:33]1.O[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([O:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16]1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([O:9][c:10]2[cH:11][cH:12][cH:13... | Nc1ccc2cnn(CCN3CCCC3)c2c1.O=C(O)Cc1cccc(Oc2ccccc2)c1 | O=C(Cc1cccc(Oc2ccccc2)c1)Nc1ccc2cnn(CCN3CCCC3)c2c1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Cc1cccc(Oc2ccccc2)c1)Nc1ccc2cnn(CCN3CCCC3)c2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[#7;a:5]:[c:6]:[c:7]:[c:8](-[NH2;D1;+0:9]):[c:10]>>[#7;a:5]:[c:6]:[c:7]:[c:8](-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]):[c:10] | null | [] | null | null | null | null | According to the procedure for Example 49, 1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-6-ylamine and (3-phenoxy-phenyl)-acetic acid were processed to provide the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.82 (m, 2 H), 1.99 (m, 2 H), 3.03 (m, 2 H), 3.51 (m, 2 H), 3.68 (m, 4 H), 4.66 (t, J=6.24 Hz, 2 H), 6.89 (m, 1 H),... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c[nH]nc2c1.C1CC[NH]C1 | HO- | null | null | null | Nc1ccc2cnn(CCN3CCCC3)c2c1.O=C(O)Cc1cccc(Oc2ccccc2)c1>>O=C(Cc1cccc(Oc2ccccc2)c1)Nc1ccc2cnn(CCN3CCCC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b24fa47016af4ab1b82440c8af12450c | Nc1ccc2cnn(CCN3CCCC3)c2c1.O=C(O)CCC(=O)c1ccc(-c2ccccc2)cc1>>O=C(CCC(=O)c1ccc(-c2ccccc2)cc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 | N1(CCCC1)CCN1N=CC2=CC=C(C=C12)N.C1(=CC=C(C=C1)C(CCC(=O)O)=O)C1=CC=CC=C1>>C1(=CC=C(C=C1)C(CCC(=O)NC1=CC=C2C=NN(C2=C1)CCN1CCCC1)=O)C1=CC=CC=C1 | [NH2:19][c:20]1[cH:21][cH:22][c:23]2[cH:24][n:25][n:26]([CH2:27][CH2:28][N:29]3[CH2:30][CH2:31][CH2:32][CH2:33]3)[c:34]2[cH:35]1.O[C:2](=[O:1])[CH2:3][CH2:4][C:5](=[O:6])[c:7]1[cH:8][cH:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:18]1>>[O:1]=[C:2]([CH2:3][CH2:4][C:5](=[O:6])[c:7]1[cH:8][cH:9][c:10]... | Nc1ccc2cnn(CCN3CCCC3)c2c1.O=C(O)CCC(=O)c1ccc(-c2ccccc2)cc1 | O=C(CCC(=O)c1ccc(-c2ccccc2)cc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CCC(=O)c1ccc(-c2ccccc2)cc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[C:5]=[O;D1;H0:6].[#7;a:7]:[c:8]:[c:9]:[c:10](-[NH2;D1;+0:11]):[c:12]>>[#7;a:7]:[c:8]:[c:9]:[c:10](-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[C:5]=[O;D1;H0:6]):[c:12] | null | [] | null | null | null | null | According to the procedure for Example 49, 1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-6-ylamine and 4-biphenyl-4-yl-4-oxo-butyric acid were processed to provide the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.80 (m, 2 H), 1.97 (m, 2 H), 2.83 (t, J=6.10 Hz, 2 H), 3.02 (m, 2 H), 3.41 (t, J=6.26 Hz, 2 H), 3.50 (m, 2 H),... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c[nH]nc2c1.C1CC[NH]C1 | HO- | null | null | null | Nc1ccc2cnn(CCN3CCCC3)c2c1.O=C(O)CCC(=O)c1ccc(-c2ccccc2)cc1>>O=C(CCC(=O)c1ccc(-c2ccccc2)cc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-23b09b32b2a14703a9e52e43225fe9da | Nc1ccc2cnn(CCN3CCCC3)c2c1.O=C(O)CCSc1ccc2ccccc2c1>>O=C(CCSc1ccc2ccccc2c1)Nc1ccc2cnn(CCN3CCCC3)c2c1 | N1(CCCC1)CCN1N=CC2=CC=C(C=C12)N.C1=C(C=CC2=CC=CC=C12)SCCC(=O)O>>C1=C(C=CC2=CC=CC=C12)SCCC(=O)NC1=CC=C2C=NN(C2=C1)CCN1CCCC1 | [NH2:16][c:17]1[cH:18][cH:19][c:20]2[cH:21][n:22][n:23]([CH2:24][CH2:25][N:26]3[CH2:27][CH2:28][CH2:29][CH2:30]3)[c:31]2[cH:32]1.O[C:2](=[O:1])[CH2:3][CH2:4][S:5][c:6]1[cH:7][cH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[cH:15]1>>[O:1]=[C:2]([CH2:3][CH2:4][S:5][c:6]1[cH:7][cH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]... | Nc1ccc2cnn(CCN3CCCC3)c2c1.O=C(O)CCSc1ccc2ccccc2c1 | O=C(CCSc1ccc2ccccc2c1)Nc1ccc2cnn(CCN3CCCC3)c2c1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CCSc1ccc2ccccc2c1)Nc1ccc2cnn(CCN3CCCC3)c2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[#7;a:5]:[c:6]:[c:7]:[c:8](-[NH2;D1;+0:9]):[c:10]>>[#7;a:5]:[c:6]:[c:7]:[c:8](-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]):[c:10] | null | [] | null | null | null | null | According to the procedure for Example 49, 1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-6-ylamine and 3-(naphthalen-2-ylsulfanyl)-propionic acid were processed to provide the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.84 (m, 2 H), 1.99 (m, 2 H), 2.79 (t, J=7.02 Hz, 2 H), 3.04 (m, 2 H), 3.40 (t, J=7.02 Hz, 2 H), 3.53 (... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2ccccc2c1.c1ccc2c[nH]nc2c1.C1CC[NH]C1 | HO- | null | null | null | Nc1ccc2cnn(CCN3CCCC3)c2c1.O=C(O)CCSc1ccc2ccccc2c1>>O=C(CCSc1ccc2ccccc2c1)Nc1ccc2cnn(CCN3CCCC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-20566292bfec44c1a9e568ed8b9cf5f3 | Cc1ccc(SCC(=O)c2ccc(CC(=O)O)s2)cc1.Nc1ccc2cnn(CCN3CCCC3)c2c1>>Cc1ccc(SCC(=O)c2ccc(CC(=O)Nc3ccc4cnn(CCN5CCCC5)c4c3)s2)cc1 | N1(CCCC1)CCN1N=CC2=CC=C(C=C12)N.C1(=CC=C(C=C1)SCC(=O)C1=CC=C(S1)CC(=O)O)C>>CC1=CC=C(C=C1)SCC(=O)C1=CC=C(S1)CC(=O)NC1=CC=C2C=NN(C2=C1)CCN1CCCC1 | O[C:15]([CH2:14][c:13]1[cH:12][cH:11][c:10]([C:8]([CH2:7][S:6][c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:36][cH:35]2)=[O:9])[s:34]1)=[O:16].[NH2:17][c:18]1[cH:19][cH:20][c:21]2[cH:22][n:23][n:24]([CH2:25][CH2:26][N:27]3[CH2:28][CH2:29][CH2:30][CH2:31]3)[c:32]2[cH:33]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6][CH2:7][C:8](=[O:9])[... | Cc1ccc(SCC(=O)c2ccc(CC(=O)O)s2)cc1.Nc1ccc2cnn(CCN3CCCC3)c2c1 | Cc1ccc(SCC(=O)c2ccc(CC(=O)Nc3ccc4cnn(CCN5CCCC5)c4c3)s2)cc1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Cc1ccc(C(=O)CSc2ccccc2)s1)Nc1ccc2cnn(CCN3CCCC3)c2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]:[#16;a:5].[#7;a:6]:[c:7]:[c:8]:[c:9](-[NH2;D1;+0:10]):[c:11]>>[#16;a:5]:[c:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[c:9](:[c:11]):[c:8]:[c:7]:[#7;a:6] | null | [] | null | null | null | null | According to the procedure for Example 49, 1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-6-ylamine and [5-(2-p-tolylsulfanyl-acetyl)-thiophen-2-yl]-acetic acid were processed to provide the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.82 (m, 2 H), 1.98 (m, 2 H), 2.25 (s, 3 H), 3.02 (m, 2 H), 3.52 (m, 2 H), 3.70 (q, J=5.8... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccsc1.c1ccc2c[nH]nc2c1.C1CC[NH]C1 | HO- | null | null | null | Cc1ccc(SCC(=O)c2ccc(CC(=O)O)s2)cc1.Nc1ccc2cnn(CCN3CCCC3)c2c1>>Cc1ccc(SCC(=O)c2ccc(CC(=O)Nc3ccc4cnn(CCN5CCCC5)c4c3)s2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-71179f252d6141649a50a5f26a9fa6f2 | Nc1ccc2cnn(CCN3CCCC3)c2c1.O=C(O)CCc1ccc(Oc2ccccc2)cc1>>O=C(CCc1ccc(Oc2ccccc2)cc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 | N1(CCCC1)CCN1N=CC2=CC=C(C=C12)N.O(C1=CC=CC=C1)C1=CC=C(C=C1)CCC(=O)O>>O(C1=CC=CC=C1)C1=CC=C(C=C1)CCC(=O)NC1=CC=C2C=NN(C2=C1)CCN1CCCC1 | [NH2:18][c:19]1[cH:20][cH:21][c:22]2[cH:23][n:24][n:25]([CH2:26][CH2:27][N:28]3[CH2:29][CH2:30][CH2:31][CH2:32]3)[c:33]2[cH:34]1.O[C:2](=[O:1])[CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([O:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][cH:17]1>>[O:1]=[C:2]([CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([O:9][c:10]2[cH:11][cH:... | Nc1ccc2cnn(CCN3CCCC3)c2c1.O=C(O)CCc1ccc(Oc2ccccc2)cc1 | O=C(CCc1ccc(Oc2ccccc2)cc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CCc1ccc(Oc2ccccc2)cc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[#7;a:5]:[c:6]:[c:7]:[c:8](-[NH2;D1;+0:9]):[c:10]>>[#7;a:5]:[c:6]:[c:7]:[c:8](-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]):[c:10] | null | [] | null | null | null | null | According to the procedure for Example 49, 1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-6-ylamine and 3-(4-phenoxy-phenyl)-propionic acid were processed to provide the title compound. MS (DCI/NH3) MS m/z 455 (M+H)+; 1H NMR (500 MHz, DMSO-d6) δ ppm 1.84 (m, 2 H), 2.00 (m, 2 H), 2.70 (t, J=7.64 Hz, 2 H), 2.94 (t, J=7.64 Hz, 2 ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c[nH]nc2c1.C1CC[NH]C1 | HO- | null | null | null | Nc1ccc2cnn(CCN3CCCC3)c2c1.O=C(O)CCc1ccc(Oc2ccccc2)cc1>>O=C(CCc1ccc(Oc2ccccc2)cc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f3aeb2ecc15a4adfa6480de630b2755d | Cc1ccc(-c2cnc(CCC(=O)O)o2)cc1.Nc1ccc2cnn(CCN3CCCC3)c2c1>>Cc1ccc(-c2cnc(CCC(=O)Nc3ccc4cnn(CCN5CCCC5)c4c3)o2)cc1 | N1(CCCC1)CCN1N=CC2=CC=C(C=C12)N.C1(=CC=C(C=C1)C1=CN=C(O1)CCC(=O)O)C>>CC1=CC=C(C=C1)C1=CN=C(O1)CCC(=O)NC1=CC=C2C=NN(C2=C1)CCN1CCCC1 | O[C:12]([CH2:11][CH2:10][c:9]1[n:8][cH:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:33][cH:32]2)[o:31]1)=[O:13].[NH2:14][c:15]1[cH:16][cH:17][c:18]2[cH:19][n:20][n:21]([CH2:22][CH2:23][N:24]3[CH2:25][CH2:26][CH2:27][CH2:28]3)[c:29]2[cH:30]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][n:8][c:9]([CH2:10][CH2:11][C:12](... | Cc1ccc(-c2cnc(CCC(=O)O)o2)cc1.Nc1ccc2cnn(CCN3CCCC3)c2c1 | Cc1ccc(-c2cnc(CCC(=O)Nc3ccc4cnn(CCN5CCCC5)c4c3)o2)cc1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CCc1ncc(-c2ccccc2)o1)Nc1ccc2cnn(CCN3CCCC3)c2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[#7;a:5]:[c:6]:[c:7]:[c:8](-[NH2;D1;+0:9]):[c:10]>>[#7;a:5]:[c:6]:[c:7]:[c:8](-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]):[c:10] | null | [] | null | null | null | null | According to the procedure for Example 49, 1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-6-ylamine and 3-(5-p-tolyl-oxazol-2-yl)-propionic acid were processed to provide the title compound. MS (DCI/NH3) MS m/z 444 (M+H)+. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.82 (m, 2 H), 1.98 (m, 2 H), 2.32 (s, 3 H), 2.93 (t, J=7.02 Hz, 2 H), 3.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1cocn1.c1ccc2c[nH]nc2c1.C1CC[NH]C1 | HO- | null | null | null | Cc1ccc(-c2cnc(CCC(=O)O)o2)cc1.Nc1ccc2cnn(CCN3CCCC3)c2c1>>Cc1ccc(-c2cnc(CCC(=O)Nc3ccc4cnn(CCN5CCCC5)c4c3)o2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7d9d8f5ed61a4222a1041d7fc0e4d8d5 | COc1cc(CC(=O)O)ccc1OCc1ccccc1.Nc1ccc2cnn(CCN3CCCC3)c2c1>>COc1cc(CC(=O)Nc2ccc3cnn(CCN4CCCC4)c3c2)ccc1OCc1ccccc1 | N1(CCCC1)CCN1N=CC2=CC=C(C=C12)N.C(C1=CC=CC=C1)OC1=C(C=C(C=C1)CC(=O)O)OC>>C(C1=CC=CC=C1)OC1=C(C=C(C=C1)CC(=O)NC1=CC=C2C=NN(C2=C1)CCN1CCCC1)OC | O[C:7]([CH2:6][c:5]1[cH:4][c:3]([O:2][CH3:1])[c:28]([O:29][CH2:30][c:31]2[cH:32][cH:33][cH:34][cH:35][cH:36]2)[cH:27][cH:26]1)=[O:8].[NH2:9][c:10]1[cH:11][cH:12][c:13]2[cH:14][n:15][n:16]([CH2:17][CH2:18][N:19]3[CH2:20][CH2:21][CH2:22][CH2:23]3)[c:24]2[cH:25]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][C:7](=[O:8])[NH:9][c... | COc1cc(CC(=O)O)ccc1OCc1ccccc1.Nc1ccc2cnn(CCN3CCCC3)c2c1 | COc1cc(CC(=O)Nc2ccc3cnn(CCN4CCCC4)c3c2)ccc1OCc1ccccc1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Cc1ccc(OCc2ccccc2)cc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[#7;a:5]:[c:6]:[c:7]:[c:8](-[NH2;D1;+0:9]):[c:10]>>[#7;a:5]:[c:6]:[c:7]:[c:8](-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]):[c:10] | null | [] | null | null | null | null | According to the procedure for Example 49, 1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-6-ylamine and (4-benzyloxy-3-methoxy-phenyl)-acetic acid were processed to provide the title compound. MS (DCI/NH3) MS m/z 485 (M+H)+. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.81 (m, 2 H), 1.97 (m, 2 H), 3.02 (m, 2 H), 3.51 (m, 2 H), 3.62 (s, 2 ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c[nH]nc2c1.C1CC[NH]C1.c1ccccc1 | HO- | null | null | null | COc1cc(CC(=O)O)ccc1OCc1ccccc1.Nc1ccc2cnn(CCN3CCCC3)c2c1>>COc1cc(CC(=O)Nc2ccc3cnn(CCN4CCCC4)c3c2)ccc1OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d0e86bcd787142f5ac7a47da242a4bc3 | COc1cc(C=CC(=O)O)ccc1OCc1ccccc1.Nc1ccc2cnn(CCN3CCCC3)c2c1>>COc1cc(/C=C/C(=O)Nc2ccc3cnn(CCN4CCCC4)c3c2)ccc1OCc1ccccc1 | N1(CCCC1)CCN1N=CC2=CC=C(C=C12)N.C(C1=CC=CC=C1)OC1=C(C=C(C=C1)C=CC(=O)O)OC>>C(C1=CC=CC=C1)OC1=C(C=C(C=C1)/C=C/C(=O)NC1=CC=C2C=NN(C2=C1)CCN1CCCC1)OC | O[C:8]([CH:7]=[CH:6][c:5]1[cH:4][c:3]([O:2][CH3:1])[c:29]([O:30][CH2:31][c:32]2[cH:33][cH:34][cH:35][cH:36][cH:37]2)[cH:28][cH:27]1)=[O:9].[NH2:10][c:11]1[cH:12][cH:13][c:14]2[cH:15][n:16][n:17]([CH2:18][CH2:19][N:20]3[CH2:21][CH2:22][CH2:23][CH2:24]3)[c:25]2[cH:26]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](/[CH:6]=[CH:7]/[C:8](... | COc1cc(C=CC(=O)O)ccc1OCc1ccccc1.Nc1ccc2cnn(CCN3CCCC3)c2c1 | COc1cc(/C=C/C(=O)Nc2ccc3cnn(CCN4CCCC4)c3c2)ccc1OCc1ccccc1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(/C=C/c1ccc(OCc2ccccc2)cc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C:4]-[c:5].[#7;a:6]:[c:7]:[c:8]:[c:9](-[NH2;D1;+0:10]):[c:11]>>[#7;a:6]:[c:7]:[c:8]:[c:9](-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])/[C:3]=[C:4]/[c:5]):[c:11] | null | [] | null | null | null | null | According to the procedure for Example 49, 1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-6-ylamine and 3-(4-benzyloxy-3-methoxy-phenyl)-acrylic acid were processed to provide the title compound. MS (DCI/NH3) MS m/z 497 (M+H)+; 1H NMR (500 MHz, DMSO-d6) δ ppm 1.85 (m, 2 H), 2.01 (m, 2 H), 3.06 (m, 2 H), 3.55 (m, 2 H), 3.71 (m,... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c[nH]nc2c1.C1CC[NH]C1.c1ccccc1 | HO- | null | null | null | COc1cc(C=CC(=O)O)ccc1OCc1ccccc1.Nc1ccc2cnn(CCN3CCCC3)c2c1>>COc1cc(/C=C/C(=O)Nc2ccc3cnn(CCN4CCCC4)c3c2)ccc1OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-13949108bc9f4bf684cbfd134a6ec002 | Nc1ccc2cnn(CCN3CCCC3)c2c1.O=C(O)Cc1ccc(Oc2ccccc2)cc1>>O=C(Cc1ccc(Oc2ccccc2)cc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 | N1(CCCC1)CCN1N=CC2=CC=C(C=C12)N.O(C1=CC=CC=C1)C1=CC=C(C=C1)CC(=O)O>>O(C1=CC=CC=C1)C1=CC=C(C=C1)CC(=O)NC1=CC=C2C=NN(C2=C1)CCN1CCCC1 | [NH2:17][c:18]1[cH:19][cH:20][c:21]2[cH:22][n:23][n:24]([CH2:25][CH2:26][N:27]3[CH2:28][CH2:29][CH2:30][CH2:31]3)[c:32]2[cH:33]1.O[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15][cH:16]1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][cH:12][cH:13... | Nc1ccc2cnn(CCN3CCCC3)c2c1.O=C(O)Cc1ccc(Oc2ccccc2)cc1 | O=C(Cc1ccc(Oc2ccccc2)cc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Cc1ccc(Oc2ccccc2)cc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[#7;a:5]:[c:6]:[c:7]:[c:8](-[NH2;D1;+0:9]):[c:10]>>[#7;a:5]:[c:6]:[c:7]:[c:8](-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]):[c:10] | null | [] | null | null | null | null | According to the procedure for Example 49, 1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-6-ylamine and (4-phenoxy-phenyl)-acetic acid were processed to provide the title compound. 1H NMR (500 MHz, DMSO-D6) δ ppm 1.82 (m, 2 H), 1.98 (m, 2 H), 3.03 (m, 2 H), 3.52 (m, 2 H), 3.69 (m, 4 H), 4.67 (t, J=6.24 Hz, 2 H), 6.99 (m, 4 H),... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c[nH]nc2c1.C1CC[NH]C1 | HO- | null | null | null | Nc1ccc2cnn(CCN3CCCC3)c2c1.O=C(O)Cc1ccc(Oc2ccccc2)cc1>>O=C(Cc1ccc(Oc2ccccc2)cc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b08ef2077e0041f3848ae625041b6fbe | Nc1ccc2cnn(CCN3CCCC3)c2c1.O=C(O)CCc1ccc(OCc2ccccc2)cc1>>O=C(CCc1ccc(OCc2ccccc2)cc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 | N1(CCCC1)CCN1N=CC2=CC=C(C=C12)N.C(C1=CC=CC=C1)OC1=CC=C(C=C1)CCC(=O)O>>C(C1=CC=CC=C1)OC1=CC=C(C=C1)CCC(=O)NC1=CC=C2C=NN(C2=C1)CCN1CCCC1 | [NH2:19][c:20]1[cH:21][cH:22][c:23]2[cH:24][n:25][n:26]([CH2:27][CH2:28][N:29]3[CH2:30][CH2:31][CH2:32][CH2:33]3)[c:34]2[cH:35]1.O[C:2](=[O:1])[CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:18]1>>[O:1]=[C:2]([CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][c... | Nc1ccc2cnn(CCN3CCCC3)c2c1.O=C(O)CCc1ccc(OCc2ccccc2)cc1 | O=C(CCc1ccc(OCc2ccccc2)cc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CCc1ccc(OCc2ccccc2)cc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[#7;a:5]:[c:6]:[c:7]:[c:8](-[NH2;D1;+0:9]):[c:10]>>[#7;a:5]:[c:6]:[c:7]:[c:8](-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]):[c:10] | null | [] | null | null | null | null | According to the procedure for Example 49, 1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-6-ylamine and 3-(4-benzyloxy-phenyl)-propionic acid were processed to provide the title compound. 1H NMR (500 MHz, DMSO-D6) δ ppm 1.83 (m, 2 H), 2.00 (m, 2 H), 2.66 (t, J=7.64 Hz, 2 H), 2.88 (t, J=7.49 Hz, 2 H), 3.05 (dd, J=10.45, 7.33 Hz... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c[nH]nc2c1.C1CC[NH]C1 | HO- | null | null | null | Nc1ccc2cnn(CCN3CCCC3)c2c1.O=C(O)CCc1ccc(OCc2ccccc2)cc1>>O=C(CCc1ccc(OCc2ccccc2)cc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cc5c29f210144d808a5adb1b9f887bc5 | Nc1ccc2cnn(CCN3CCCC3)c2c1.O=C(O)C=Cc1cnccc1Oc1ccccc1>>O=C(/C=C/c1cnccc1Oc1ccccc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 | N1(CCCC1)CCN1N=CC2=CC=C(C=C12)N.O(C1=CC=CC=C1)C1=C(C=NC=C1)C=CC(=O)O>>O(C1=CC=CC=C1)C1=C(C=NC=C1)/C=C/C(=O)NC1=CC=C2C=NN(C2=C1)CCN1CCCC1 | [NH2:18][c:19]1[cH:20][cH:21][c:22]2[cH:23][n:24][n:25]([CH2:26][CH2:27][N:28]3[CH2:29][CH2:30][CH2:31][CH2:32]3)[c:33]2[cH:34]1.O[C:2](=[O:1])[CH:3]=[CH:4][c:5]1[cH:6][n:7][cH:8][cH:9][c:10]1[O:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[O:1]=[C:2](/[CH:3]=[CH:4]/[c:5]1[cH:6][n:7][cH:8][cH:9][c:10]1[O:11][c:12]1[... | Nc1ccc2cnn(CCN3CCCC3)c2c1.O=C(O)C=Cc1cnccc1Oc1ccccc1 | O=C(/C=C/c1cnccc1Oc1ccccc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(/C=C/c1cnccc1Oc1ccccc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C:4]-[c:5]:[c:6]:[#7;a:7].[#7;a:8]:[c:9]:[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#7;a:8]:[c:9]:[c:10]:[c:11](-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])/[C:3]=[C:4]/[c:5]:[c:6]:[#7;a:7]):[c:13] | null | [] | null | null | null | null | According to the procedure for Example 49, 1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-6-ylamine and 3-(4-phenoxy-pyridin-3-yl)-acrylic acid were processed to provide the title compound. MS (DCI/NH3) MS m/z 454 (M+H)+; 1H NMR (500 MHz, DMSO-d6) δ ppm 1.84 (m, 2 H), 2.01 (m, 2 H), 3.07 (m, 2 H), 3.54 (m, 2 H), 3.73 (m, 2 H),... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccccc1.c1ccc2c[nH]nc2c1.C1CC[NH]C1 | HO- | null | null | null | Nc1ccc2cnn(CCN3CCCC3)c2c1.O=C(O)C=Cc1cnccc1Oc1ccccc1>>O=C(/C=C/c1cnccc1Oc1ccccc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9727ca075c614adc83b0e823bec8581b | Nc1ccc2cnn(CCN3CCCC3)c2c1.O=C(O)Cc1ccc(O)cc1>>O=C(Cc1ccc(O)cc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 | N1(CCCC1)CCN1N=CC2=CC=C(C=C12)N.OC1=CC=C(C=C1)CC(=O)O.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=N2)N=N1.F[P-](F)(F)(F)(F)F.C(C)(C)N(CC)C(C)C>>OC1=CC=C(C=C1)CC(=O)NC1=CC=C2C=NN(C2=C1)CCN1CCCC1 | [NH2:11][c:12]1[cH:13][cH:14][c:15]2[cH:16][n:17][n:18]([CH2:19][CH2:20][N:21]3[CH2:22][CH2:23][CH2:24][CH2:25]3)[c:26]2[cH:27]1.O[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:9][cH:10]1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:9][cH:10]1)[NH:11][c:12]1[cH:13][cH:14][c:15]2[cH:16][n:17][n:18]([CH... | Nc1ccc2cnn(CCN3CCCC3)c2c1.O=C(O)Cc1ccc(O)cc1 | O=C(Cc1ccc(O)cc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Cc1ccccc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[#7;a:5]:[c:6]:[c:7]:[c:8](-[NH2;D1;+0:9]):[c:10]>>[#7;a:5]:[c:6]:[c:7]:[c:8](-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]):[c:10] | null | [] | null | null | 6 | HOUR | A mixture of 1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-6-ylamine (0.620 g, 2.69 mmol), (4-hydroxy-phenyl)-acetic acid (0.242 g, 5.15 mmol), HATU (1.23 g, 3.23 mmol) and diisopropylethylamine (0.939 mL, 5.39 mmol) in 9 mL of DMF was stirred at room temperature for 6 hours, concentrated under reduced pressure and the residu... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c[nH]nc2c1.C1CC[NH]C1 | HO- | CN(C)C=O | null | 6 | Nc1ccc2cnn(CCN3CCCC3)c2c1.O=C(O)Cc1ccc(O)cc1>CN(C)C=O>O=C(Cc1ccc(O)cc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-aa96a474265f4fd28b14e1f0c36687d8 | Fc1ccc(CBr)cc1.O=C(Cc1ccc(O)cc1)Nc1ccc2cnn(CCN3CCCC3)c2c1>>O=C(Cc1ccc(OCc2ccc(F)cc2)cc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 | OC1=CC=C(C=C1)CC(=O)NC1=CC=C2C=NN(C2=C1)CCN1CCCC1.BrCC1=CC=C(C=C1)F.C(=O)([O-])[O-].[Cs+].[Cs+]>>FC1=CC=C(COC2=CC=C(C=C2)CC(=O)NC2=CC=C3C=NN(C3=C2)CCN2CCCC2)C=C1 | Br[CH2:9][c:10]1[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]1.[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:17][cH:18]1)[NH:19][c:20]1[cH:21][cH:22][c:23]2[cH:24][n:25][n:26]([CH2:27][CH2:28][N:29]3[CH2:30][CH2:31][CH2:32][CH2:33]3)[c:34]2[cH:35]1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][c:10]2[cH... | Fc1ccc(CBr)cc1.O=C(Cc1ccc(O)cc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 | O=C(Cc1ccc(OCc2ccc(F)cc2)cc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(Cc1ccc(OCc2ccccc2)cc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | null | [] | null | null | 6 | HOUR | A mixture of 2-(4-hydroxy-phenyl)-N-[1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-6-yl]-acetamide (45.0 mg, 0.124 mmol), 1-bromomethyl-4-fluoro-benzene (35.0 mg, 0.185 mmol), Cs2CO3 (60.0 mg, 0.184 mmol) in 2 mL of DMF was shaken for 6 hours and concentrated under reduced pressure. The residue was dissolved in a 1:1 mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccc2c[nH]nc2c1.C1CC[NH]C1 | HBr | CN(C)C=O | null | 6 | Fc1ccc(CBr)cc1.O=C(Cc1ccc(O)cc1)Nc1ccc2cnn(CCN3CCCC3)c2c1>CN(C)C=O>O=C(Cc1ccc(OCc2ccc(F)cc2)cc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-be0dfe59a2b64a20927446459a008702 | Nc1ccc2cnn(CCN3CCCC3)c2c1.O=C(Cl)Oc1ccccc1>>O=C(Nc1ccc2cnn(CCN3CCCC3)c2c1)Oc1ccccc1 | N1(CCCC1)CCN1N=CC2=CC=C(C=C12)N.C(C)N(CC)CC.ClC(=O)OC1=CC=CC=C1>>N1(CCCC1)CCN1N=CC2=CC=C(C=C12)NC(OC1=CC=CC=C1)=O | [NH2:3][c:4]1[cH:5][cH:6][c:7]2[cH:8][n:9][n:10]([CH2:11][CH2:12][N:13]3[CH2:14][CH2:15][CH2:16][CH2:17]3)[c:18]2[cH:19]1.Cl[C:2](=[O:1])[O:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]2[cH:8][n:9][n:10]([CH2:11][CH2:12][N:13]3[CH2:14][CH2:15][CH2:16][CH2:17]3)[c:18]2[cH:19]1... | Nc1ccc2cnn(CCN3CCCC3)c2c1.O=C(Cl)Oc1ccccc1 | O=C(Nc1ccc2cnn(CCN3CCCC3)c2c1)Oc1ccccc1 | null | null | C1CCOC1 | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | O=C(Nc1ccc2cnn(CCN3CCCC3)c2c1)Oc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[c:4].[#7;a:5]:[c:6]:[c:7]:[c:8](-[NH2;D1;+0:9]):[c:10]>>[#7;a:5]:[c:6]:[c:7]:[c:8](-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[c:4]):[c:10] | null | [] | null | null | 1 | HOUR | To a mixture of 1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-6-ylamine (0.220 g, 0.955 mmol) and triethylamine (0.240 mL, 1.72 mmol) in 1 mL of THF at 0 C was slowly added phenyl chloroformate (0.246 ml, 1.72 mmol). The mixture was stirred cold for 1 hours and the formed precipitate collected by filtration with rinsing with ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccc2c[nH]nc2c1.C1CC[NH]C1.c1ccccc1 | HCl | C1CCOC1 | null | 1 | Nc1ccc2cnn(CCN3CCCC3)c2c1.O=C(Cl)Oc1ccccc1>C1CCOC1>O=C(Nc1ccc2cnn(CCN3CCCC3)c2c1)Oc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-06dbbfb91b364cc0afe00fc3defc95f4 | Nc1ccc2cnn(CCN3CCCC3)c2c1.O=C(O)Cc1ccc(Br)cc1>>O=C(Cc1ccc(Br)cc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 | N1(CCCC1)CCN1N=CC2=CC=C(C=C12)N.BrC1=CC=C(C=C1)CC(=O)O.Cl.C(C)N=C=NC(CC)(C)C.ON1N=NC2=C1C=CC=C2.CN1CCOCC1>>BrC1=CC=C(C=C1)CC(=O)NC1=CC=C2C=NN(C2=C1)CCN1CCCC1 | [NH2:11][c:12]1[cH:13][cH:14][c:15]2[cH:16][n:17][n:18]([CH2:19][CH2:20][N:21]3[CH2:22][CH2:23][CH2:24][CH2:25]3)[c:26]2[cH:27]1.O[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][cH:10]1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][cH:10]1)[NH:11][c:12]1[cH:13][cH:14][c:15]2[cH:16][n:17][n:18]([CH... | Nc1ccc2cnn(CCN3CCCC3)c2c1.O=C(O)Cc1ccc(Br)cc1 | O=C(Cc1ccc(Br)cc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Cc1ccccc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[#7;a:5]:[c:6]:[c:7]:[c:8](-[NH2;D1;+0:9]):[c:10]>>[#7;a:5]:[c:6]:[c:7]:[c:8](-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]):[c:10] | null | [] | null | null | 6 | HOUR | A mixture of 1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-6-ylamine (480 mg, 2.09 mmol), (4-bromo-phenyl)-acetic acid (449 mg, 2.09 mmol), ethyldimethylpropylcarbodiimide hydrochloride (470 mg, 2.23 mmol), N-hydroxybenzotriazole (330 mg, 2.44 mmol), N-methyl morpholine (500 mg, 5.00 mmol) in 20 mL of DMF was shaken for 6 hou... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2c[nH]nc2c1.C1CC[NH]C1 | HO- | CN(C)C=O | null | 6 | Nc1ccc2cnn(CCN3CCCC3)c2c1.O=C(O)Cc1ccc(Br)cc1>CN(C)C=O>O=C(Cc1ccc(Br)cc1)Nc1ccc2cnn(CCN3CCCC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9c434eed02d64b4e99342a018ccff5d5 | CN(C)CCCl.O=[N+]([O-])c1ccc2cn[nH]c2c1>>CN(C)CCn1ncc2ccc([N+](=O)[O-])cc21 | [N+](=O)([O-])C1=CC=C2C=NNC2=C1.C([O-])([O-])=O.[K+].[K+].Cl.CN(CCCl)C>>CN(CCN1N=CC2=CC=C(C=C12)[N+](=O)[O-])C | Cl[CH2:5][CH2:4][N:2]([CH3:1])[CH3:3].[nH:6]1[n:7][cH:8][c:9]2[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][c:17]12>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][n:6]1[n:7][cH:8][c:9]2[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][c:17]12 | CN(C)CCCl.O=[N+]([O-])c1ccc2cn[nH]c2c1 | CN(C)CCn1ncc2ccc([N+](=O)[O-])cc21 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0691c2afa71aa114f9fdcf61af01716a80f3f3e3c77a100978fd513beb44a770 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc2[nH]ncc2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[c:4]:[c:5]1:[c:6]:[c:7]:[#7;a:8]:[nH;D2;+0:9]:1>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:9]1:[#7;a:8]:[c:7]:[c:6]:[c:5]:1:[c:4] | 64 | [{"value": 64.0, "product": "CN(CCN1N=CC2=CC=C(C=C12)[N+](=O)[O-])C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.0, "product": "CN(CCN1N=CC2=CC=C(C=C12)[N+](=O)[O-])C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | A mixture of 6-nitroindazole (2 g, 12 mmol) and potassium carbonate (5.1 g 37 mmol) in DMF (40 mL) for 30 minutes, followed by the addition of 2-(dimethylamino)ethylchloride hydrochloride (2.65 g 18.4 mmol) was added. The mixture was heated to 60° C. for 6 hours, cooled to room temperature, filtered through a plug of s... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ncc2c1 | c1ccc2cn[nH]c2c1 | c1ccc2cn[nH]c2c1 | HCl | CN(C)C=O | 60 | null | CN(C)CCCl.O=[N+]([O-])c1ccc2cn[nH]c2c1>CN(C)C=O>CN(C)CCn1ncc2ccc([N+](=O)[O-])cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b656292c47b34836923d5467612fa5bd | CN(C)CCn1ncc2ccc([N+](=O)[O-])cc21>>CN(C)CCn1ncc2ccc(N)cc21 | CN(CCN1N=CC2=CC=C(C=C12)[N+](=O)[O-])C.[Cl-].[NH4+]>>CN(CCN1N=CC2=CC=C(C=C12)N)C | O=[N+:13]([O-])[c:12]1[cH:11][cH:10][c:9]2[cH:8][n:7][n:6]([CH2:5][CH2:4][N:2]([CH3:1])[CH3:3])[c:15]2[cH:14]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][n:6]1[n:7][cH:8][c:9]2[cH:10][cH:11][c:12]([NH2:13])[cH:14][c:15]12 | CN(C)CCn1ncc2ccc([N+](=O)[O-])cc21 | CN(C)CCn1ncc2ccc(N)cc21 | null | [Fe] | C(C)O.O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2[nH]ncc2c1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | 92 | [{"value": 92.0, "product": "CN(CCN1N=CC2=CC=C(C=C12)N)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.1, "product": "CN(CCN1N=CC2=CC=C(C=C12)N)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A mixture of dimethyl-[2-(6-nitro-indazol-1-yl)-ethyl]-amine (1 g, 4.3 mmol), iron powder (1.9 g, 34 mmol), and ammonium chloride (120 mg, 2.2 mmol) in a 4:1 Ethanol/H2O solution (20 mL) was heated to reflux for 3 hours, cooled to room temperature and concentrated under reduced pressure. The residue was stirred in trie... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2cn[nH]c2c1 | Other | [Fe].C(C)O.O | null | 0.25 | CN(C)CCn1ncc2ccc([N+](=O)[O-])cc21>[Fe].C(C)O.O>CN(C)CCn1ncc2ccc(N)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fff2b7e8a5fd4546beaa9b700e84e723 | CN(C)CCn1ncc2ccc(N)cc21.O=C(O)Cc1ccc(OCc2ccccc2)cc1>>CN(C)CCn1ncc2ccc(NC(=O)Cc3ccc(OCc4ccccc4)cc3)cc21 | CN(CCN1N=CC2=CC=C(C=C12)N)C.C(C1=CC=CC=C1)OC1=CC=C(C=C1)CC(=O)O.Cl.C(C)N=C=NC(CC)(C)C.ON1N=NC2=C1C=CC=C2.CN1CCOCC1>>C(C1=CC=CC=C1)OC1=CC=C(C=C1)CC(=O)NC1=CC=C2C=NN(C2=C1)CCN(C)C | [CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][n:6]1[n:7][cH:8][c:9]2[cH:10][cH:11][c:12]([NH2:13])[cH:31][c:32]12.O[C:14](=[O:15])[CH2:16][c:17]1[cH:18][cH:19][c:20]([O:21][CH2:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[cH:29][cH:30]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][n:6]1[n:7][cH:8][c:9]2[cH:10][cH:11][c:12]([NH:13][C:... | CN(C)CCn1ncc2ccc(N)cc21.O=C(O)Cc1ccc(OCc2ccccc2)cc1 | CN(C)CCn1ncc2ccc(NC(=O)Cc3ccc(OCc4ccccc4)cc3)cc21 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Cc1ccc(OCc2ccccc2)cc1)Nc1ccc2cn[nH]c2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[#7;a:5]:[c:6]:[c:7]:[c:8](-[NH2;D1;+0:9]):[c:10]>>[#7;a:5]:[c:6]:[c:7]:[c:8](-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]):[c:10] | 95 | [{"value": 95.0, "product": "C(C1=CC=CC=C1)OC1=CC=C(C=C1)CC(=O)NC1=CC=C2C=NN(C2=C1)CCN(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | A mixture of 1-(2-dimethylamino-ethyl)-1H-indazol-6-ylamine (484 mg, 2 mmol), 4-benzyloxy-phenylacetic acid (200 mg, 2 mmol), ethyldimethylpropylcarbodiimide hydrochloride (460 mg, 2.4 mmol), N-hydroxybenzotriazole (324 mg, 2.4 mmol), and N-methyl morpholine (513 mg, 4.8 mmol) in DMF (15 mL) was stirred at room tempera... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2cn[nH]c2c1.c1ccccc1.c1ccccc1 | HO- | CN(C)C=O | null | 6 | CN(C)CCn1ncc2ccc(N)cc21.O=C(O)Cc1ccc(OCc2ccccc2)cc1>CN(C)C=O>CN(C)CCn1ncc2ccc(NC(=O)Cc3ccc(OCc4ccccc4)cc3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-156f18bd1e9c4a489266174512da3607 | COC(CBr)OC.O=[N+]([O-])c1ccc2cn[nH]c2c1>>COC(Cn1ncc2ccc([N+](=O)[O-])cc21)OC | [N+](=O)([O-])C1=CC=C2C=NNC2=C1.C(=O)([O-])[O-].[K+].[K+].COC(CBr)OC>>COC(CN1N=CC2=CC=C(C=C12)[N+](=O)[O-])OC | Br[CH2:4][CH:3]([O:2][CH3:1])[O:17][CH3:18].[nH:5]1[n:6][cH:7][c:8]2[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][c:16]12>>[CH3:1][O:2][CH:3]([CH2:4][n:5]1[n:6][cH:7][c:8]2[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][c:16]12)[O:17][CH3:18] | COC(CBr)OC.O=[N+]([O-])c1ccc2cn[nH]c2c1 | COC(Cn1ncc2ccc([N+](=O)[O-])cc21)OC | null | null | O.CN(C)C=O.C(C)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0691c2afa71aa114f9fdcf61af01716a80f3f3e3c77a100978fd513beb44a770 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc2[nH]ncc2c1 | Br-[CH2;D2;+0:1]-[C:2](-[#8:3])-[#8:4].[c:5]:[c:6]1:[c:7]:[c:8]:[#7;a:9]:[nH;D2;+0:10]:1>>[#8:3]-[C:2](-[#8:4])-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[#7;a:9]:[c:8]:[c:7]:[c:6]:1:[c:5] | null | [] | null | null | null | null | To a mixture of 6-nitroindazole (10.0 g, 61 mmol) and K2CO3 (9.31 g, 67.5 mmol) in DMF (60 mL) at room temperature was added 2-bromoacetaldehyde dimethylacetal (7.98 mL, 67.5 mmol), after which the mixture was heated to 50 C for 18 hours. The mixture was cooled to room temperature, diluted with diethyl ether (60 mL) an... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ncc2c1 | c1ccc2cn[nH]c2c1 | c1ccc2cn[nH]c2c1 | HBr | O.CN(C)C=O.C(C)OCC | null | null | COC(CBr)OC.O=[N+]([O-])c1ccc2cn[nH]c2c1>O.CN(C)C=O.C(C)OCC>COC(Cn1ncc2ccc([N+](=O)[O-])cc21)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-818e4ca598ff4a3cb2d249174af30651 | COC(CN1NCc2ccc([N+](=O)[O-])cc21)OC>>COC(CN1NCc2ccc(N)cc21)OC | COC(CN1NCC2=CC=C(C=C12)[N+](=O)[O-])OC.[NH4+].[Cl-]>>COC(CN1NCC2=CC=C(C=C12)N)OC | O=[N+:12]([O-])[c:11]1[cH:10][cH:9][c:8]2[c:14]([cH:13]1)[N:5]([CH2:4][CH:3]([O:2][CH3:1])[O:15][CH3:16])[NH:6][CH2:7]2>>[CH3:1][O:2][CH:3]([CH2:4][N:5]1[NH:6][CH2:7][c:8]2[cH:9][cH:10][c:11]([NH2:12])[cH:13][c:14]21)[O:15][CH3:16] | COC(CN1NCc2ccc([N+](=O)[O-])cc21)OC | COC(CN1NCc2ccc(N)cc21)OC | null | [Fe] | C(C)O.O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2c(c1)CNN2 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | To a mixture of 1-(2,2-dimethoxyethyl)-6-nitro-2H-indazole (1.89 g, 7.52 mmol) and NH4Cl (337 mg, 6.01 mmol) in ethanol/H2O (2:1, 75 mL) at room temperature was added Fe (1.28 g, 23.7 mmol) and the mixture was heated for 2 hours at 70 C. The mixture was cooled to room temperature, filtered through celite, which was was... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2c(c1)CN[NH]2 | Other | [Fe].C(C)O.O | null | null | COC(CN1NCc2ccc([N+](=O)[O-])cc21)OC>[Fe].C(C)O.O>COC(CN1NCc2ccc(N)cc21)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-617281cfdb2a4aca86b9036de7f9c7ef | COC(CN1NCc2ccc(N)cc21)OC.O=C(O)Cc1ccc(Oc2ccccc2)cc1>>COC(Cn1ncc2ccc(NC(=O)Cc3ccc(Oc4ccccc4)cc3)cc21)OC | COC(CN1NCC2=CC=C(C=C12)N)OC.O(C1=CC=CC=C1)C1=CC=C(C=C1)CC(=O)O.CN1CCOCC1.C=1C=CC2=C(C1)N=NN2O.Cl.C(C)N=C=NC(CC)(C)C>>COC(CN1N=CC2=CC=C(C=C12)NC(CC1=CC=C(C=C1)OC1=CC=CC=C1)=O)OC | [CH3:1][O:2][CH:3]([CH2:4][N:5]1[NH:6][CH2:7][c:8]2[cH:9][cH:10][c:11]([NH2:12])[cH:29][c:30]21)[O:31][CH3:32].O[C:13](=[O:14])[CH2:15][c:16]1[cH:17][cH:18][c:19]([O:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[cH:27][cH:28]1>>[CH3:1][O:2][CH:3]([CH2:4][n:5]1[n:6][cH:7][c:8]2[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14]... | COC(CN1NCc2ccc(N)cc21)OC.O=C(O)Cc1ccc(Oc2ccccc2)cc1 | COC(Cn1ncc2ccc(NC(=O)Cc3ccc(Oc4ccccc4)cc3)cc21)OC | null | null | O.CN(C)C=O.C(C)OCC | Acylation | OtherReaction | 8674dd94480641940316e175adf7a1a665516a0cba4be80383ea8cdadb1975ab | 05d157b14bc277b9e860908a32ecbb47419722550cd0886abbbb9c2e597f5277 | O=C(Cc1ccc(Oc2ccccc2)cc1)Nc1ccc2cn[nH]c2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[C:5]-[C:6]-[N;H0;D3;+0:7]1-[NH;D2;+0:8]-[CH2;D2;+0:9]-[c:10]2:[c:11]:[c:12]:[c:13](-[NH2;D1;+0:14]):[c:15]:[c:16]:2-1>>[C:5]-[C:6]-[n;H0;D3;+0:7]1:[n;H0;D2;+0:8]:[cH;D2;+0:9]:[c:10]2:[c:11]:[c:12]:[c:13](-[NH;D2;+0:14]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]):[c:15]:[c:16]:2... | null | [] | null | null | 3 | HOUR | A mixture of 1-(2,2-dimethoxyethyl)-2H-indazol-6-ylamine (1.89 g, 8.60 mmol), 4-phenoxyphenylacetic acid (2.06 g, 9.03 mmol), N-methyl morpholine (2.26 mL, 20.6 mmol), HOBt (1.45 g, 10.75 mmol), and ethyldimethylpropylcarbodiimide hydrochloride (2.06 g, 10.75 mmol) in DMF (40 mL) was stirred at room temperature for 3 h... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Carboxylic acid.Primary amine | Secondary amide | c1ccc2c(c1)CN[NH]2 | c1ccc2cn[nH]c2c1 | c1ccc2cn[nH]c2c1.c1ccccc1.c1ccccc1 | HO- | O.CN(C)C=O.C(C)OCC | null | 3 | COC(CN1NCc2ccc(N)cc21)OC.O=C(O)Cc1ccc(Oc2ccccc2)cc1>O.CN(C)C=O.C(C)OCC>COC(Cn1ncc2ccc(NC(=O)Cc3ccc(Oc4ccccc4)cc3)cc21)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a835ac973187491bb8f4f17c90a620d1 | COC(Cn1ncc2ccc(NC(=O)Cc3ccc(Oc4ccccc4)cc3)cc21)OC>>O=CCn1ncc2ccc(NC(=O)Cc3ccc(Oc4ccccc4)cc3)cc21 | COC(CN1N=CC2=CC=C(C=C12)NC(CC1=CC=C(C=C1)OC1=CC=CC=C1)=O)OC.Cl>>O=CCN1N=CC2=CC=C(C=C12)NC(CC1=CC=C(C=C1)OC1=CC=CC=C1)=O | CO[CH:2]([O:1]C)[CH2:3][n:4]1[n:5][cH:6][c:7]2[cH:8][cH:9][c:10]([NH:11][C:12](=[O:13])[CH2:14][c:15]3[cH:16][cH:17][c:18]([O:19][c:20]4[cH:21][cH:22][cH:23][cH:24][cH:25]4)[cH:26][cH:27]3)[cH:28][c:29]12>>[O:1]=[CH:2][CH2:3][n:4]1[n:5][cH:6][c:7]2[cH:8][cH:9][c:10]([NH:11][C:12](=[O:13])[CH2:14][c:15]3[cH:16][cH:17][c... | COC(Cn1ncc2ccc(NC(=O)Cc3ccc(Oc4ccccc4)cc3)cc21)OC | O=CCn1ncc2ccc(NC(=O)Cc3ccc(Oc4ccccc4)cc3)cc21 | null | null | CC(=O)C.C(C)(=O)OCC | Miscellaneous | Acetal hydrolysis to aldehyde | 2c5baf4818f438d514702dbb9f9a64f069b67040aebce8bef29fab8232955599 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | O=C(Cc1ccc(Oc2ccccc2)cc1)Nc1ccc2cn[nH]c2c1 | C-O-[CH;D3;+0:1](-[C:2]-[#7;a:3])-[O;H0;D2;+0:4]-C>>[#7;a:3]-[C:2]-[CH;D2;+0:1]=[O;H0;D1;+0:4] | null | [] | null | null | null | null | A mixture of N-[1-(2,2-dimethoxyethyl)-1H-indazol-6-yl]-2-(4-phenoxyphenyl)acetamide (2.0 g, 4.64 mmol) and 2N aqueous HCl (6.0 mL)in acetone (40 mL) was heated to reflux for 3 hours, cooled and diluted with ethyl acetate (300 mL). The layers were separated, and the organic was dried (Na2SO4), filtered, and concentrate... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | null | null | c1ccc2cn[nH]c2c1.c1ccccc1.c1ccccc1 | HO- | CC(=O)C.C(C)(=O)OCC | null | null | COC(Cn1ncc2ccc(NC(=O)Cc3ccc(Oc4ccccc4)cc3)cc21)OC>CC(=O)C.C(C)(=O)OCC>O=CCn1ncc2ccc(NC(=O)Cc3ccc(Oc4ccccc4)cc3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5a48f10fdd91405e9f7c6f0d95002581 | NC1CCCC1.O=CCn1ncc2ccc(NC(=O)Cc3ccc(Oc4ccccc4)cc3)cc21>>O=C(Cc1ccc(Oc2ccccc2)cc1)Nc1ccc2cnn(CCNC3CCCC3)c2c1 | O=CCN1N=CC2=CC=C(C=C12)NC(CC1=CC=C(C=C1)OC1=CC=CC=C1)=O.C1(CCCC1)N.[BH3-]C#N.[Na+]>>C1(CCCC1)NCCN1N=CC2=CC=C(C=C12)NC(CC1=CC=C(C=C1)OC1=CC=CC=C1)=O | [NH2:27][CH:28]1[CH2:29][CH2:30][CH2:31][CH2:32]1.O=[CH:26][CH2:25][n:24]1[n:23][cH:22][c:21]2[cH:20][cH:19][c:18]([NH:17][C:2](=[O:1])[CH2:3][c:4]3[cH:5][cH:6][c:7]([O:8][c:9]4[cH:10][cH:11][cH:12][cH:13][cH:14]4)[cH:15][cH:16]3)[cH:34][c:33]21>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][cH:1... | NC1CCCC1.O=CCn1ncc2ccc(NC(=O)Cc3ccc(Oc4ccccc4)cc3)cc21 | O=C(Cc1ccc(Oc2ccccc2)cc1)Nc1ccc2cnn(CCNC3CCCC3)c2c1 | null | null | C(C)(=O)OCC.C1CCOC1 | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | O=C(Cc1ccc(Oc2ccccc2)cc1)Nc1ccc2cnn(CCNC3CCCC3)c2c1 | O=[CH;D2;+0:1]-[C:2]-[#7;a:3].[C:4]-[C:5](-[NH2;D1;+0:6])-[C:7]>>[#7;a:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:6]-[C:5](-[C:4])-[C:7] | null | [] | null | null | 18 | HOUR | A mixture of N-[1-(2-oxoethyl)-1H-indazol-6-yl]-2-(4-phenoxyphenyl)acetamide (20 mg, 0.05 mmol) and cyclopentylamine (10 μL, 0.10 mmol) in THF (1 mL) was stirred at room temperature for 0.5 hours after which NaCNBH3 (0.104 mL, 0.010 mmol, 1 M in THF) was added and the mixture was stirred for an additional 18 hours. The... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1ccc2c[nH]nc2c1.C1CCCC1 | Other | C(C)(=O)OCC.C1CCOC1 | null | 18 | NC1CCCC1.O=CCn1ncc2ccc(NC(=O)Cc3ccc(Oc4ccccc4)cc3)cc21>C(C)(=O)OCC.C1CCOC1>O=C(Cc1ccc(Oc2ccccc2)cc1)Nc1ccc2cnn(CCNC3CCCC3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f933d4246fc24498b2d7e5d7f99e055d | COC(CCn1ncc2ccc(N)cc21)OC.O=C(O)Cc1ccc(Oc2ccccc2)cc1>>COC(CCn1ncc2ccc(NC(=O)Cc3ccc(Oc4ccccc4)cc3)cc21)OC | COC(CCN1N=CC2=CC=C(C=C12)N)OC.O(C1=CC=CC=C1)C1=CC=C(C=C1)CC(=O)O.CN1CCOCC1.C=1C=CC2=C(C1)N=NN2O.Cl.C(C)N=C=NC(CC)(C)C>>COC(CCN1N=CC2=CC=C(C=C12)NC(CC1=CC=C(C=C1)OC1=CC=CC=C1)=O)OC | [CH3:1][O:2][CH:3]([CH2:4][CH2:5][n:6]1[n:7][cH:8][c:9]2[cH:10][cH:11][c:12]([NH2:13])[cH:30][c:31]12)[O:32][CH3:33].O[C:14](=[O:15])[CH2:16][c:17]1[cH:18][cH:19][c:20]([O:21][c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[cH:28][cH:29]1>>[CH3:1][O:2][CH:3]([CH2:4][CH2:5][n:6]1[n:7][cH:8][c:9]2[cH:10][cH:11][c:12]([NH:13]... | COC(CCn1ncc2ccc(N)cc21)OC.O=C(O)Cc1ccc(Oc2ccccc2)cc1 | COC(CCn1ncc2ccc(NC(=O)Cc3ccc(Oc4ccccc4)cc3)cc21)OC | null | null | O.CN(C)C=O.C(C)OCC | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Cc1ccc(Oc2ccccc2)cc1)Nc1ccc2cn[nH]c2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[#7;a:5]:[c:6]:[c:7]:[c:8](-[NH2;D1;+0:9]):[c:10]>>[#7;a:5]:[c:6]:[c:7]:[c:8](-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]):[c:10] | null | [] | null | null | 3 | HOUR | A mixture of 1-(3,3-dimethoxypropyl)-1H-indazole-6-ylamine (1.32 g, 5.60 mmol), 4-phenoxyphenylacetic acid (1.34 g, 5.88 mmol), N-methyl morpholine (1.47 mL, 13.4 mmol), HOBt (945 mg, 7.0 mmol), and ethyldimethylpropylcarbodiimide hydrochloride (1.34 g, 7.0 mmol) in DMF (28 mL) was stirred at room temperature for 3 hou... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2cn[nH]c2c1.c1ccccc1.c1ccccc1 | HO- | O.CN(C)C=O.C(C)OCC | null | 3 | COC(CCn1ncc2ccc(N)cc21)OC.O=C(O)Cc1ccc(Oc2ccccc2)cc1>O.CN(C)C=O.C(C)OCC>COC(CCn1ncc2ccc(NC(=O)Cc3ccc(Oc4ccccc4)cc3)cc21)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3e5ebf92fa5340759bf9af3ca85b7367 | COC(CCn1ncc2ccc(NC(=O)Cc3ccc(Oc4ccccc4)cc3)cc21)OC>>O=CCCn1ncc2ccc(NC(=O)Cc3ccc(Oc4ccccc4)cc3)cc21 | COC(CCN1N=CC2=CC=C(C=C12)NC(CC1=CC=C(C=C1)OC1=CC=CC=C1)=O)OC.Cl>>O=CCCN1N=CC2=CC=C(C=C12)NC(CC1=CC=C(C=C1)OC1=CC=CC=C1)=O | CO[CH:2]([O:1]C)[CH2:3][CH2:4][n:5]1[n:6][cH:7][c:8]2[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])[CH2:15][c:16]3[cH:17][cH:18][c:19]([O:20][c:21]4[cH:22][cH:23][cH:24][cH:25][cH:26]4)[cH:27][cH:28]3)[cH:29][c:30]12>>[O:1]=[CH:2][CH2:3][CH2:4][n:5]1[n:6][cH:7][c:8]2[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])[CH2:15][c:16]3... | COC(CCn1ncc2ccc(NC(=O)Cc3ccc(Oc4ccccc4)cc3)cc21)OC | O=CCCn1ncc2ccc(NC(=O)Cc3ccc(Oc4ccccc4)cc3)cc21 | null | null | CC(=O)C | Miscellaneous | Acetal hydrolysis to aldehyde | 2c5baf4818f438d514702dbb9f9a64f069b67040aebce8bef29fab8232955599 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | O=C(Cc1ccc(Oc2ccccc2)cc1)Nc1ccc2cn[nH]c2c1 | C-O-[CH;D3;+0:1](-[C:2]-[C:3])-[O;H0;D2;+0:4]-C>>[C:3]-[C:2]-[CH;D2;+0:1]=[O;H0;D1;+0:4] | null | [] | null | null | null | null | A mixture of N-[1-(3,3-dimethoxypropyl)-1H-indazol-6-yl]-2-(4-phenoxyphenyl)acetamide (500 mg, 1.12 mmol) and 2N aqueous HCl (2.5 mL) in acetone (5 mL) was heated to 50 C for 3 hours, cooled to room temperature and concentrated under reduced pressure to a volume of ˜2 mL. Diethyl ether (15 mL) was added with stirring a... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | null | null | c1ccc2cn[nH]c2c1.c1ccccc1.c1ccccc1 | HO- | CC(=O)C | null | null | COC(CCn1ncc2ccc(NC(=O)Cc3ccc(Oc4ccccc4)cc3)cc21)OC>CC(=O)C>O=CCCn1ncc2ccc(NC(=O)Cc3ccc(Oc4ccccc4)cc3)cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2e4a8dd9a6bf48d4bfe72c30037c6410 | CC1CCCNC1.O=CCCn1ncc2ccc(NC(=O)Cc3ccc(Oc4ccccc4)cc3)cc21>>CC1CCCN(CCCn2ncc3ccc(NC(=O)Cc4ccc(Oc5ccccc5)cc4)cc32)C1 | O=CCCN1N=CC2=CC=C(C=C12)NC(CC1=CC=C(C=C1)OC1=CC=CC=C1)=O.CC1CNCCC1.C(C)(=O)O>>CC1CN(CCC1)CCCN1N=CC2=CC=C(C=C12)NC(CC1=CC=C(C=C1)OC1=CC=CC=C1)=O | [CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][NH:6][CH2:36]1.O=[CH:7][CH2:8][CH2:9][n:10]1[n:11][cH:12][c:13]2[cH:14][cH:15][c:16]([NH:17][C:18](=[O:19])[CH2:20][c:21]3[cH:22][cH:23][c:24]([O:25][c:26]4[cH:27][cH:28][cH:29][cH:30][cH:31]4)[cH:32][cH:33]3)[cH:34][c:35]12>>[CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][N:6]([CH2:7][CH2:8][CH... | CC1CCCNC1.O=CCCn1ncc2ccc(NC(=O)Cc3ccc(Oc4ccccc4)cc3)cc21 | CC1CCCN(CCCn2ncc3ccc(NC(=O)Cc4ccc(Oc5ccccc5)cc4)cc32)C1 | null | null | CO | Heteroatom Alkylation and Arylation | reductive amination | d0e659bc8d1e29e09a61320b4c537e66ad57335a51368c8bd48de9bdffa59372 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | O=C(Cc1ccc(Oc2ccccc2)cc1)Nc1ccc2cnn(CCCN3CCCCC3)c2c1 | O=[CH;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]-[C:3])-[C:7]-[C:8] | null | [] | null | null | 18 | HOUR | To a mixture of N-[1-(3-oxopropyl)-1H-indazol-6-yl]-2-(4-phenoxyphenyl)acetamide (20 mg, 0.05 mmol) and 3-methylpiperidine (10 mg, 0.10 mmol) in methanol containing 2% v/v acetic acid (1 mL) was added and MP-CNBH3 (52 mg, 0.065 mmol). The mixture was shaken at 40 C for 18 hours, cooled to room temperature and filtered,... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2cn[nH]c2c1.c1ccccc1.c1ccccc1 | Other | CO | null | 18 | CC1CCCNC1.O=CCCn1ncc2ccc(NC(=O)Cc3ccc(Oc4ccccc4)cc3)cc21>CO>CC1CCCN(CCCn2ncc3ccc(NC(=O)Cc4ccc(Oc5ccccc5)cc4)cc32)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ef15d739bea941aabac76ed0632749c2 | CS(=O)(=O)Cl.O=C1OCCN1CCO>>CS(=O)(=O)OCCN1CCOC1=O | OCCN1C(OCC1)=O.CCN(C(C)C)C(C)C.S(=O)(=O)(C)Cl>>O=C1OCCN1CCOS(=O)(=O)C | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][CH2:7][N:8]1[CH2:9][CH2:10][O:11][C:12]1=[O:13]>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][CH2:7][N:8]1[CH2:9][CH2:10][O:11][C:12]1=[O:13] | CS(=O)(=O)Cl.O=C1OCCN1CCO | CS(=O)(=O)OCCN1CCOC1=O | null | null | ClCCl.O | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | O=C1NCCO1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 40.7 | [{"value": 40.7, "product": "O=C1OCCN1CCOS(=O)(=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a mixture of 3-(2-hydroxy-ethyl)-oxazolidin-2-one (1.00 g, 7.63 mmol) and Hunigs base (2.92 mL, 16.8 mmol) in dichloromethane (19 mL) at 0° C. was added mesyl chloride (0.650 mL, 8.40 mmol) slowly via syringe. The mixture was stir cold for three hours, diluted with 10 mL of water and 25 mL of dichloromethane. The la... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | C1COC[NH]1 | HCl | ClCCl.O | null | 3 | CS(=O)(=O)Cl.O=C1OCCN1CCO>ClCCl.O>CS(=O)(=O)OCCN1CCOC1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b43d88ecf0c54ba2b4e9d777cbce85ac | CS(=O)(=O)OCCN1CCOC1=O.O=[N+]([O-])c1ccc2cn[nH]c2c1>>O=C1OCCN1CCn1ncc2ccc([N+](=O)[O-])cc21 | [N+](=O)([O-])C1=CC=C2C=NNC2=C1.C([O-])([O-])=O.[K+].[K+].O=C1OCCN1CCOS(=O)(=O)C>>[N+](=O)([O-])C1=CC=C2C=NN(C2=C1)CCN1C(OCC1)=O | CS(=O)(=O)O[CH2:8][CH2:7][N:6]1[C:2](=[O:1])[O:3][CH2:4][CH2:5]1.[nH:9]1[n:10][cH:11][c:12]2[cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19][c:20]12>>[O:1]=[C:2]1[O:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][n:9]1[n:10][cH:11][c:12]2[cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19][c:20]12 | CS(=O)(=O)OCCN1CCOC1=O.O=[N+]([O-])c1ccc2cn[nH]c2c1 | O=C1OCCN1CCn1ncc2ccc([N+](=O)[O-])cc21 | null | null | CN(C)C=O | Functional Group Addition | OtherReaction | 59fbeed92b390f1dd725d754f1e4fe56cfad5f328705886a1c1a1e9cfd091b3e | 080650f477946c2e5856c863f910d70b8691303314dea1c921ead79db86123ee | O=C1OCCN1CCn1ncc2ccccc21 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[#7:3]-[C:4]=[O;D1;H0:5].[c:6]:[c:7]1:[c:8]:[c:9]:[#7;a:10]:[nH;D2;+0:11]:1>>[O;D1;H0:5]=[C:4]-[#7:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:11]1:[#7;a:10]:[c:9]:[c:8]:[c:7]:1:[c:6] | 39 | [{"value": 39.0, "product": "[N+](=O)([O-])C1=CC=C2C=NN(C2=C1)CCN1C(OCC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.0, "product": "[N+](=O)([O-])C1=CC=C2C=NN(C2=C1)CCN1C(OCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | To a mixture of 3-(2-hydroxy-ethyl)-oxazolidin-2-one (1.00 g, 7.63 mmol) and Hunigs base (2.92 mL, 16.8 mmol) in dichloromethane (19 mL) at 0° C. was added mesyl chloride (0.650 mL, 8.40 mmol) slowly via syringe. The mixture was stir cold for three hours, diluted with 10 mL of water and 25 mL of dichloromethane. The la... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate | null | c1ccc2[nH]ncc2c1 | c1ccc2cn[nH]c2c1 | C1COC[NH]1.c1ccc2cn[nH]c2c1 | MsOH.HO- | CN(C)C=O | 60 | null | CS(=O)(=O)OCCN1CCOC1=O.O=[N+]([O-])c1ccc2cn[nH]c2c1>CN(C)C=O>O=C1OCCN1CCn1ncc2ccc([N+](=O)[O-])cc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fb45ff45038845cc97d115942c5e8842 | O=C1OCCN1CCn1ncc2ccc([N+](=O)[O-])cc21>>Nc1ccc2cnn(CCN3CCOC3=O)c2c1 | [N+](=O)([O-])C1=CC=C2C=NN(C2=C1)CCN1C(OCC1)=O.[Cl-].[NH4+]>>NC1=CC=C2C=NN(C2=C1)CCN1C(OCC1)=O | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]2[cH:6][n:7][n:8]([CH2:9][CH2:10][N:11]3[CH2:12][CH2:13][O:14][C:15]3=[O:16])[c:17]2[cH:18]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][n:7][n:8]([CH2:9][CH2:10][N:11]3[CH2:12][CH2:13][O:14][C:15]3=[O:16])[c:17]2[cH:18]1 | O=C1OCCN1CCn1ncc2ccc([N+](=O)[O-])cc21 | Nc1ccc2cnn(CCN3CCOC3=O)c2c1 | null | [Fe] | C(C)O.O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C1OCCN1CCn1ncc2ccccc21 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | 67.7 | [{"value": 67.0, "product": "NC1=CC=C2C=NN(C2=C1)CCN1C(OCC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.7, "product": "NC1=CC=C2C=NN(C2=C1)CCN1C(OCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A mixture of 3-[2-(6-Nitro-indazol-1-yl)-ethyl]-oxazolidin-2-one (200 mg, 0.72 mmol), iron powder (400 mg, 7.1 mmol), and ammonium chloride (20 mg, 0.37 mmol) in a 4:1 ethanol/H2O solution (5 mL) was heated to reflux for 3 hours, cooled to room temperature, concentrated under reduced pressure. The resudue was stirred i... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2c[nH]nc2c1.C1COC[NH]1 | Other | [Fe].C(C)O.O | null | 0.25 | O=C1OCCN1CCn1ncc2ccc([N+](=O)[O-])cc21>[Fe].C(C)O.O>Nc1ccc2cnn(CCN3CCOC3=O)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6a1b0502c1d14ea5b84ec72be69c1c58 | Nc1ccc2cnn(CCN3CCOC3=O)c2c1.O=C(O)Cc1ccc(OCc2ccccc2)cc1>>O=C(Cc1ccc(OCc2ccccc2)cc1)Nc1ccc2cnn(CCN3CCOC3=O)c2c1 | NC1=CC=C2C=NN(C2=C1)CCN1C(OCC1)=O.C(C1=CC=CC=C1)OC1=CC=C(C=C1)CC(=O)O.Cl.C(C)N=C=NC(CC)(C)C.ON1N=NC2=C1C=CC=C2.CN1CCOCC1>>C(C1=CC=CC=C1)OC1=CC=C(C=C1)CC(=O)NC1=CC=C2C=NN(C2=C1)CCN1C(OCC1)=O | [NH2:18][c:19]1[cH:20][cH:21][c:22]2[cH:23][n:24][n:25]([CH2:26][CH2:27][N:28]3[CH2:29][CH2:30][O:31][C:32]3=[O:33])[c:34]2[cH:35]1.O[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][cH:17]1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][... | Nc1ccc2cnn(CCN3CCOC3=O)c2c1.O=C(O)Cc1ccc(OCc2ccccc2)cc1 | O=C(Cc1ccc(OCc2ccccc2)cc1)Nc1ccc2cnn(CCN3CCOC3=O)c2c1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Cc1ccc(OCc2ccccc2)cc1)Nc1ccc2cnn(CCN3CCOC3=O)c2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[#7;a:5]:[c:6]:[c:7]:[c:8](-[NH2;D1;+0:9]):[c:10]>>[#7;a:5]:[c:6]:[c:7]:[c:8](-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]):[c:10] | 52 | [{"value": 52.0, "product": "C(C1=CC=CC=C1)OC1=CC=C(C=C1)CC(=O)NC1=CC=C2C=NN(C2=C1)CCN1C(OCC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.4, "product": "C(C1=CC=CC=C1)OC1=CC=C(C=C1)CC(=O)NC1=CC=C2C=NN(C2=C1)CCN1C(OCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | A mixture of 3-[2-(6-Amino-indazol-1-yl)-ethyl]-oxazolidin-2-one (58 mg, 0.24 mmol), 4-benzyloxyphenylacetic acid (68 mg, 0.28 mmol), ethyldimethylpropylcarbodiimide hydrochloride (53 mg, 0.28 mmol), N-hydroxybenzotriazole (37 mg, 0.28 mmol) and N-methyl morpholine (60 mg, 0.56 mmol) in 3 mL of DMF was stirred at room ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c[nH]nc2c1.C1COC[NH]1 | HO- | CN(C)C=O | null | 6 | Nc1ccc2cnn(CCN3CCOC3=O)c2c1.O=C(O)Cc1ccc(OCc2ccccc2)cc1>CN(C)C=O>O=C(Cc1ccc(OCc2ccccc2)cc1)Nc1ccc2cnn(CCN3CCOC3=O)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-423b9194011247918f05f636f46ac013 | CN(C)CCCCl.O=[N+]([O-])c1ccc2cn[nH]c2c1>>CN(C)CCCn1ncc2ccc([N+](=O)[O-])cc21 | [N+](=O)([O-])C1=CC=C2C=NNC2=C1.C([O-])([O-])=O.[K+].[K+].Cl.ClCCCN(C)C>>CN(CCCN1N=CC2=CC=C(C=C12)[N+](=O)[O-])C | Cl[CH2:6][CH2:5][CH2:4][N:2]([CH3:1])[CH3:3].[nH:7]1[n:8][cH:9][c:10]2[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][c:18]12>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH2:6][n:7]1[n:8][cH:9][c:10]2[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][c:18]12 | CN(C)CCCCl.O=[N+]([O-])c1ccc2cn[nH]c2c1 | CN(C)CCCn1ncc2ccc([N+](=O)[O-])cc21 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0691c2afa71aa114f9fdcf61af01716a80f3f3e3c77a100978fd513beb44a770 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc2[nH]ncc2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[c:4]:[c:5]1:[c:6]:[c:7]:[#7;a:8]:[nH;D2;+0:9]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:9]1:[#7;a:8]:[c:7]:[c:6]:[c:5]:1:[c:4] | null | [] | 60 | CELSIUS | null | null | A mixture of 6-nitro-1H-indazole (0.500 g, 3.07 mmol) and potassium carbonate (0.889 g, 6.44 mmol) in 15.3 mL of DMF was stirred for 30 minutes after which (3-chloro-propyl)-dimethyl-amine hydrochloride (0.553 g 3.50 mmol) was added. The reaction mixture was then heated to 60° C. for 6 hours, cooled to room temperature... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2[nH]ncc2c1 | c1ccc2cn[nH]c2c1 | c1ccc2cn[nH]c2c1 | HCl | CN(C)C=O | 60 | null | CN(C)CCCCl.O=[N+]([O-])c1ccc2cn[nH]c2c1>CN(C)C=O>CN(C)CCCn1ncc2ccc([N+](=O)[O-])cc21 |
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