HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cyclopropanemethanol → racemic 6-cyclopropylmethoxy-5-(4-fluoro-phenyl)-N-(2-hydroxymethyl-butyl)-nicotinamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cyclopropanemethanol | HCID 75644 | — |
| Reactant | 5-Bromo-6-chloropyridine-3-carboxylic acid | HCID 285433 | — |
| Reactant | 4-Fluorophenylboronic acid | HCID 285645 | — |
| Reactant | 2-(Aminomethyl)butan-1-ol | HCID 15356533 | — |
| Product | racemic 6-cyclopropylmethoxy-5-(4-fluoro-phenyl)-N-(2-hydroxymethyl-butyl)-nicotinamide | HCID 21109657 | — |
Reaction Steps
The title compound was synthesized in analogy to Example 75, using 5-bromo-6-chloro-3-pyridinecarboxylic acid, cyclopropanemethanol, (4-fluoro-phenyl)-boronic acid and 2-aminomethyl-1-butanol as starting materials to yield racemic 6-cyclopropylmethoxy-5-(4-fluoro-phenyl)-N-(2-hydroxymethyl-butyl)-nicotinamide. Separation with heptane/ethanol on ChiralpakAD® yielded the (−)-enantiomer, MS (ISP) 373.2 (M+H)+, αD20: −4.9° in MeOH.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07229999B2 |
| Source dataset | uspto-grants-2007_06 |
| ORD ID | ord-2edddf99dddf4495b8e0148cc0755fb3 |
| Source note | uspto-grants-2007_06 |