Cyclopropanemethanol → (RS)-6-cyclopropylmethoxy-N-(3,3,3-trifluoro-2-hydroxy-2-methyl-propyl)-5-(4-trifluoromethyl-phenyl)-nicotinamide

HRID 1929904Notes

Reaction equation

HRID 1929904 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][C:32]([CH3:38])([OH:37])[C:33]([F:36])([F:35])[F: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][C:32]([OH:37])([CH3:38])[C:33]([F:36])([F:35])[F:34])=[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 136207593-Amino-1,1,1-trifluoro-2-methylpropan-2-ol

Product 1

HCID 21109688(RS)-6-cyclopropylmethoxy-N-(3,3,3-trifluoro-2-hydroxy-2-methyl-propyl)-5-(4-trifluoromethyl-phenyl)-nicotinamide

Procedure

The title compound was synthesized in analogy to Example 31, using 5-bromo-6-chloro-3-pyridinecarboxylic acid, hydroxymethylcyclopropan, 4-trifluoromethyl-phenylboronic acid and 3-amino-1,1,1-trifluoro-2-methyl-propan-2-ol (CAN [354-68-7]) as starting materials to yield (RS)-6-cyclopropylmethoxy-N-(3,3,3-trifluoro-2-hydroxy-2-methyl-propyl)-5-(4-trifluoromethyl-phenyl)-nicotinamide as off-white solid, MS (ISP) 463.0 (M+H)+.

Workup

  1. customThe title compound was synthesized in analogy to Example 31

Sources & evidence

ORD record
ord-e28565ffcb914e5d90cd4f1665416a93
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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