Cyclopropanemethanol → (RS)-5-(4-cyano-phenyl)-6-cyclopropylmethoxy-N-(2-hydroxymethyl-butyl)-nicotinamide

HRID 1766547Notes

Reaction equation

HRID 1766547 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.[C:17]([C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1)#[N:18].[NH2:28][CH2:29][CH:30]([CH2:33][CH3:34])[CH2:31][OH:32]>>[C:17]([C:19]1[CH:24]=[CH:23][C:22]([C:2]2[C:7]([O:12][CH2:13][CH:14]3[CH2:16][CH2:15]3)=[N:6][CH:5]=[C:4]([CH:3]=2)[C:9]([NH:28][CH2:29][CH:30]([CH2:31][OH:32])[CH2:33][CH3:34])=[O:11])=[CH:21][CH:20]=1)#[N:18]

Participants

5

Reactant 4

HCID 75644CyclopropanemethanolHCID 2854335-Bromo-6-chloropyridine-3-carboxylic acidHCID 27343264-Cyanophenylboronic acidHCID 153565332-(Aminomethyl)butan-1-ol

Product 1

HCID 21109685(RS)-5-(4-cyano-phenyl)-6-cyclopropylmethoxy-N-(2-hydroxymethyl-butyl)-nicotinamide

Procedure

The title compound was synthesized in analogy to Example 75, using 5-bromo-6-chloro-3-pyridinecarboxylic acid, hydroxymethyl-cyclopropan, 4-cyanophenylboronic acid and 2-(aminomethyl)-1-butanol as starting materials to yield (RS)-5-(4-cyano-phenyl)-6-cyclopropylmethoxy-N-(2-hydroxymethyl-butyl)-nicotinamide. MS (ISP) 380.2 (M+H)+.

Workup

  1. customThe title compound was synthesized in analogy to Example 75

Sources & evidence

ORD record
ord-05dbf231cf2d495c861b729dc31dc33a
Source dataset
uspto-grants-2007_06
Patent number
US07229999B2

Reaction notes

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