Cyclopropanemethanol → (RS)-6-cyclopropylmethoxy-N-(2-hydroxymethyl-butyl)-5-(4-trifluoromethoxy-phenyl)-nicotinamide

HRID 1766550Notes

Reaction equation

HRID 1766550 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]([OH:11])=O)[CH:5]=[N:6][C:7]=1Cl.[OH:12][CH2:13][CH:14]1[CH2:16][CH2:15]1.[F:17][C:18]([F:30])([F:29])[O:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.[NH2:31][CH2:32][CH:33]([CH2:36][CH3:37])[CH2:34][OH:35]>>[CH:14]1([CH2:13][O:12][C:7]2[C:2]([C:23]3[CH:24]=[CH:25][C:20]([O:19][C:18]([F:30])([F:29])[F:17])=[CH:21][CH:22]=3)=[CH:3][C:4]([C:9]([NH:31][CH2:32][CH:33]([CH2:34][OH:35])[CH2:36][CH3:37])=[O:11])=[CH:5][N:6]=2)[CH2:16][CH2:15]1

Participants

5

Reactant 4

HCID 75644CyclopropanemethanolHCID 2854335-Bromo-6-chloropyridine-3-carboxylic acidHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 153565332-(Aminomethyl)butan-1-ol

Product 1

HCID 21109660(RS)-6-cyclopropylmethoxy-N-(2-hydroxymethyl-butyl)-5-(4-trifluoromethoxy-phenyl)-nicotinamide

Procedure

The title compound was synthesized in analogy to Example 75, using 5-bromo-6-chloro-3-pyridinecarboxylic acid, hydroxymethyl-cyclopropan, 4-trifluoromethoxy-phenylboronic acid and 2-(aminomethyl)-1-butanol as starting materials to yield (RS)-6-cyclopropylmethoxy-N-(2-hydroxymethyl-butyl)-5-(4-trifluoromethoxy-phenyl)-nicotinamide. M0S (ISP) 439.0 (M+H)+

Workup

  1. customThe title compound was synthesized in analogy to Example 75

Sources & evidence

ORD record
ord-38653328656847a78576ba2d71892fb2
Source dataset
uspto-grants-2007_06
Patent number
US07229999B2

Reaction notes

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