Piconol → N-((R)-2-cyclopropyl-2-hydroxy-propyl)-5-(4-fluoro-phenyl)-6-(pyridin-2-ylmethoxy)-nicotinamide

HRID 1929899Notes

Reaction equation

HRID 1929899 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]([OH:11])=O)[CH:5]=[N:6][C:7]=1Cl.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][OH:19].[F:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.[NH2:30][CH2:31][C@@:32]([CH3:37])([CH:34]1[CH2:36][CH2:35]1)[OH:33]>>[CH:34]1([C@:32]([OH:33])([CH3:37])[CH2:31][NH:30][C:9](=[O:11])[C:4]2[CH:3]=[C:2]([C:24]3[CH:25]=[CH:26][C:21]([F:20])=[CH:22][CH:23]=3)[C:7]([O:19][CH2:18][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][N:12]=3)=[N:6][CH:5]=2)[CH2:36][CH2:35]1

Participants

5

Reactant 4

HCID 11474PiconolHCID 2854335-Bromo-6-chloropyridine-3-carboxylic acidHCID 2856454-Fluorophenylboronic acidHCID 51684102(2R)-1-amino-2-cyclopropyl-propan-2-ol

Product 1

HCID 24856917N-((R)-2-cyclopropyl-2-hydroxy-propyl)-5-(4-fluoro-phenyl)-6-(pyridin-2-ylmethoxy)-nicotinamide

Procedure

The title compound was synthesized in analogy to Example 31, using 5-bromo-6-chloro-3-pyridinecarboxylic acid, 2-pyridinemethanol, (4-fluoro-phenyl)-boronic acid and (R)-α-(aminomethyl)-α-methyl-cyclopropanemethanol as starting materials to yield N—((R)-2-cyclopropyl-2-hydroxy-propyl)-5-(4-fluoro-phenyl)-6-(pyridin-2-ylmethoxy)-nicotinamide, MS (ISP) 422.0 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-a4514b4526be4fbc905829feaf990f8a
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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