HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dichloroethane → N-(3-(1H-benzo[d]imidazol-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)-4,4-difluorocyclo hexane carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dichloroethane | HCID 11 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 4,4-Difluorocyclohexanecarboxylic acid | HCID 2779136 | — |
| Reactant | 3-(1H-benzo[d]imidazol-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-amine | HCID 136352245 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | N-(3-(1H-benzo[d]imidazol-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)-4,4-difluorocyclo hexane carboxamide | HCID 136352254 | 46.3% |
Reaction Steps
4,4-Difluorocyclohexanecarboxylic acid (8 mg, 0.048 mmol), HOBt (9 mg, 0.066 mmol), EDC (13 mg, 0.068 mmol) and sodium bicarbonate (4 mg, 0.047 mmol) was added to a solution of 3-(1H-benzo[d]imidazol-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-amine (15 mg, 0.045 mmol) in DMF (5 mL). The reaction mixture was stirred at room temperature for 24 h, and then the solvent was removed in vacuo. Purification by flash chromatography (6% CH3OH/CH2Cl2) afforded the title compound (10 mg). 1H NMR (400 MHz, CD3OD): δ 8.51 (s, 1H), 7.74 (m, 2H), 7.66 (m, 2H), 7.28 (m, 2H), 5.92 (d, 1H, J=8.8 Hz), 4.01 (m, 1H), 3.84 (m, 1H), 2.66 (m, 1H), 2.54-2.44 (m, 2H), 2.17 (m, 3H), 2.01-1.70 (m, 9H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08569511B2 |
| Source dataset | uspto-grants-2013_10 |
| ORD ID | ord-f70b3f0ce95443bbafbd6e2622c1c933 |
| Source note | uspto-grants-2013_10 |