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

HRID 1766551Notes

Reaction equation

HRID 1766551 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:29])([F:28])[C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.[NH2:30][CH2:31][CH:32]([CH2:35][CH3:36])[CH2:33][OH:34]>>[CH:14]1([CH2:13][O:12][C:7]2[C:2]([C:22]3[CH:23]=[CH:24][C:19]([C:18]([F:29])([F:28])[F:17])=[CH:20][CH:21]=3)=[CH:3][C:4]([C:9]([NH:30][CH2:31][CH:32]([CH2:33][OH:34])[CH2:35][CH3:36])=[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 27343894-(Trifluoromethyl)phenylboronic acidHCID 153565332-(Aminomethyl)butan-1-ol

Product 1

HCID 21109661(RS)-6-cyclopropylmethoxy-N-(2-hydroxymethyl-butyl)-5-(4-trifluoromethyl-phenyl)-nicotinamide

Procedure

The title compound was synthesized in analogy to Example 75, using 5-bromo-6-chloro-3-pyridinecarboxylic acid, hydroxymethyl-cyclopropan, 4-trifluoromethyl-phenylboronic acid and 2-(aminomethyl)-1-butanol as starting materials to yield (RS)-6-cyclopropylmethoxy-N-(2-hydroxymethyl-butyl)-5-(4-trifluoromethyl-phenyl)-nicotinamide. MS (ISP) 423.3 (M+H)+

Workup

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

Sources & evidence

ORD record
ord-394141f112c748f7a2bf6073bb70c6a7
Source dataset
uspto-grants-2007_06
Patent number
US07229999B2

Reaction notes

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