4-Hydroxymethylpyridine → 5-(4-Chloro-phenyl)-N-((S)-2-cyclopropyl-2-hydroxy-propyl)-6-(pyridin-4-ylmethoxy)-nicotinamide

HRID 1929882Notes

Reaction equation

HRID 1929882 reaction equation
CO[C:3]([C:5]1[CH:6]=[N:7][C:8](Cl)=[C:9](Br)[CH:10]=1)=[O:4].[Cl:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.[OH:23][CH2:24][C:25]1[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=1.[NH2:31][CH2:32][C@:33]([CH3:38])([CH:35]1[CH2:37][CH2:36]1)[OH:34]>>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:9]2[C:8]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=3)=[N:7][CH:6]=[C:5]([CH:10]=2)[C:3]([NH:31][CH2:32][C@:33]([CH:35]2[CH2:37][CH2:36]2)([OH:34])[CH3:38])=[O:4])=[CH:16][CH:15]=1

Participants

5

Reactant 4

HCID 114724-HydroxymethylpyridineHCID 742994-Chlorophenylboronic acidHCID 2764313Methyl 5-bromo-6-chloronicotinateHCID 51684100(S)-1-Amino-2-cyclopropylpropan-2-ol

Product 1

HCID 248568365-(4-Chloro-phenyl)-N-((S)-2-cyclopropyl-2-hydroxy-propyl)-6-(pyridin-4-ylmethoxy)-nicotinamide

Procedure

The title compound was synthesized in analogy to the procedure described for the preparation of Example 5, using 5-bromo-6-chloro-3-pyridinecarboxylic acid methyl ester, 4-chlorophenyl-boronic acid (commercially available), 4-(hydroxymethyl)-pyridine, and (5)-α-(aminomethyl)-α-methyl-cyclopropanemethanol (WO 2006/106054) as starting materials. MS (ISP): 438.1 (M+H+).

Workup

  1. customdescribed for the preparation of Example 5

Sources & evidence

ORD record
ord-db445cba53a04e988a934ac33b51f512
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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