HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 5-(4-Chloro-phenyl)-6-cyclopropylmethoxy-N-((1R,2R)-2-hydroxy-cyclohexyl)-nicotinamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | (1R,2R)-2-Aminocyclohexanol | HCID 735777 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Reactant | 5-(4-Chlorophenyl)-6-(cyclopropylmethoxy)nicotinic acid | HCID 66687482 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 5-(4-Chloro-phenyl)-6-cyclopropylmethoxy-N-((1R,2R)-2-hydroxy-cyclohexyl)-nicotinamide | HCID 11951124 | 76.2% |
Reaction Steps
5-(4-Chloro-phenyl)-6-cyclopropylmethoxy-nicotinic acid (21.5 g, 0.071 mol) was dissolved in DMF (655 mL). To the solution was added TBTU (25 g, 0.078 mol), N,N-diisopropylethyl amine (60.5 mL, 0.35 mol) and (1R,2R)-2-amino-cyclohexanol (11.8 g, 0.078 mol). The reaction mixture was stirred for 16 h at room temperature. The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica (n-heptane/ethyl acetate gradient) to yield 21.7 g of the title compound as a white solid, MS (ISP) 401.2 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08188093B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-51597620eccf451ca6207648276a4981 |
| Source note | uspto-grants-2012_05 |