Cyclopropanemethanol → racemic 6-cyclopropylmethoxy-5-(4-fluoro-phenyl)-N-(2-hydroxymethyl-butyl)-nicotinamide

HRID 1766511Notes

Reaction equation

HRID 1766511 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]([OH:11])=O)[CH:5]=[N:6][C:7]=1Cl.[CH:12]1([CH2:15][OH:16])[CH2:14][CH2:13]1.[F:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.[NH2:27][CH2:28][CH:29]([CH2:32][CH3:33])[CH2:30][OH:31]>>[CH:12]1([CH2:15][O:16][C:7]2[C:2]([C:21]3[CH:22]=[CH:23][C:18]([F:17])=[CH:19][CH:20]=3)=[CH:3][C:4]([C:9]([NH:27][CH2:28][CH:29]([CH2:30][OH:31])[CH2:32][CH3:33])=[O:11])=[CH:5][N:6]=2)[CH2:14][CH2:13]1

Participants

5

Reactant 4

HCID 75644CyclopropanemethanolHCID 2854335-Bromo-6-chloropyridine-3-carboxylic acidHCID 2856454-Fluorophenylboronic acidHCID 153565332-(Aminomethyl)butan-1-ol

Product 1

HCID 21109657racemic 6-cyclopropylmethoxy-5-(4-fluoro-phenyl)-N-(2-hydroxymethyl-butyl)-nicotinamide

Procedure

The title compound was synthesized in analogy to Example 75, using 5-bromo-6-chloro-3-pyridinecarboxylic acid, cyclopropanemethanol, (4-fluoro-phenyl)-boronic acid and 2-aminomethyl-1-butanol as starting materials to yield racemic 6-cyclopropylmethoxy-5-(4-fluoro-phenyl)-N-(2-hydroxymethyl-butyl)-nicotinamide. Separation with heptane/ethanol on ChiralpakAD® yielded the (−)-enantiomer, MS (ISP) 373.2 (M+H)+, αD20: −4.9° in MeOH.

Workup

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

Sources & evidence

ORD record
ord-2edddf99dddf4495b8e0148cc0755fb3
Source dataset
uspto-grants-2007_06
Patent number
US07229999B2

Reaction notes

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