Cyclopropanemethanol → N-((S)-2-Cyclopropyl-2-hydroxy-propyl)-6-cyclopropylmethoxy-5-(4-trifluoromethyl-phenyl)-nicotinamide

HRID 1929868Notes

Reaction equation

HRID 1929868 reaction equation
CO[C:3](=[O:12])[C:4]1[CH:9]=[C:8](Br)[C:7](Cl)=[N:6][CH:5]=1.[OH:13][CH2:14][CH:15]1[CH2:17][CH2:16]1.[F:18][C:19]([F:30])([F:29])[C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.[NH2:31][CH2:32][C@:33]([CH3:38])([CH:35]1[CH2:37][CH2:36]1)[OH:34]>>[CH:35]1([C@@:33]([OH:34])([CH3:38])[CH2:32][NH:31][C:3](=[O:12])[C:4]2[CH:9]=[C:8]([C:23]3[CH:24]=[CH:25][C:20]([C:19]([F:30])([F:29])[F:18])=[CH:21][CH:22]=3)[C:7]([O:13][CH2:14][CH:15]3[CH2:17][CH2:16]3)=[N:6][CH:5]=2)[CH2:37][CH2:36]1

Participants

5

Reactant 4

HCID 75644CyclopropanemethanolHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 2764313Methyl 5-bromo-6-chloronicotinateHCID 51684100(S)-1-Amino-2-cyclopropylpropan-2-ol

Product 1

HCID 11950064N-((S)-2-Cyclopropyl-2-hydroxy-propyl)-6-cyclopropylmethoxy-5-(4-trifluoromethyl-phenyl)-nicotinamide

Procedure

The title compound was synthesized in analogy to the procedure described for the preparation of Example 43, using 5-bromo-6-chloro-nicotinic acid methyl ester, hydroxymethylcyclopropane (commercially available), 4-trifluoromethylphenyl-boronic acid (commercially available) and (S)-α-(aminomethyl)-α-methyl-cyclopropanemethanol (WO 2006/106054) as starting materials. MS (ISP): 435.3 (M+H+).

Workup

  1. customdescribed for the preparation of Example 43

Sources & evidence

ORD record
ord-7b271aca7db04be49cda034650ac4659
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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