4-Hydroxymethylpyridine → 5-(4-Cyano-phenyl)-6-cyclopropylmethoxy-N-((trans)-2-hydroxy-cyclohexyl)-nicotinamide

HRID 1929910Notes

Reaction equation

HRID 1929910 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]([OH:11])=O)[CH:5]=[N:6][C:7]=1Cl.N1[CH:17]=[CH:16][C:15]([CH2:18][OH:19])=CC=1.[C:20]([C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1)#[N:21].[NH2:31][C@@H:32]1[CH2:37][CH2:36][CH2:35][CH2:34][C@H:33]1[OH:38]>>[C:20]([C:22]1[CH:27]=[CH:26][C:25]([C:2]2[C:7]([O:19][CH2:18][CH:15]3[CH2:16][CH2:17]3)=[N:6][CH:5]=[C:4]([CH:3]=2)[C:9]([NH:31][C@@H:32]2[CH2:37][CH2:36][CH2:35][CH2:34][C@H:33]2[OH:38])=[O:11])=[CH:24][CH:23]=1)#[N:21]

Participants

5

Reactant 4

HCID 114724-HydroxymethylpyridineHCID 2854335-Bromo-6-chloropyridine-3-carboxylic acidHCID 735777(1R,2R)-2-AminocyclohexanolHCID 27343264-Cyanophenylboronic acid

Product 1

HCID 248566375-(4-Cyano-phenyl)-6-cyclopropylmethoxy-N-((trans)-2-hydroxy-cyclohexyl)-nicotinamide

Procedure

The title compound was synthesized in analogy to Example 31, using 5-bromo-6-chloro-3-pyridinecarboxylic acid, 4-pyridinemethanol, (4-cyano-phenyl)-boronic acid and (1R,2R)-2-amino-1-cyclohexanol as starting materials to yield 5-(4-cyano-phenyl)-6-cyclopropylmethoxy-N-((1R,2R)-2-hydroxy-cyclohexyl)-nicotinamide, MS (ISP) 392.2 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-a3e514507362489daa59c61e3bd5d15b
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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