2-Methoxyethanol → HCID 11949888, compound

HRID 1766512Notes

Reaction equation

HRID 1766512 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]([OH:11])=O)[CH:5]=[N:6][C:7]=1Cl.[F:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.[NH2:22][CH2:23][C@H:24]1[CH2:29][CH2:28][CH2:27][CH2:26][C@H:25]1[OH:30].[CH3:31][O:32][CH2:33][CH2:34][OH:35]>>[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:2]2[C:7]([O:35][CH2:34][CH2:33][O:32][CH3:31])=[N:6][CH:5]=[C:4]([CH:3]=2)[C:9]([NH:22][CH2:23][C@@H:24]2[CH2:29][CH2:28][CH2:27][CH2:26][C@@H:25]2[OH:30])=[O:11])=[CH:15][CH:14]=1

Participants

5

Reactant 4

HCID 80192-MethoxyethanolHCID 2854335-Bromo-6-chloropyridine-3-carboxylic acidHCID 2856454-Fluorophenylboronic acidHCID 12483365cis-2-Aminomethyl-1-cyclohexanol

Product 1

HCID 11949888HCID 11949888, compound

Procedure

The title compound was synthesized in analogy to Example 75, using 5-bromo-6-chloro-3-pyridinecarboxylic acid, 2-methoxyethanol, (4-fluoro-phenyl)-boronic acid and cis-2-aminomethyl-1-cyclohexanol as starting materials to yield racemic cis-5-(4-fluoro-phenyl)-N-(2-hydroxy-cyclohexylmethyl)-6-(2-methoxy-ethoxy)-nicotinamide. Separation with heptane/ethanol on ChiralpakAD® yielded the (−)-enantiomer, MS (ISP) 403.4 (M+H)+, αD20: −17.1° in MeOH.

Workup

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

Sources & evidence

ORD record
ord-e8d94177ab68453c956eace3c9566650
Source dataset
uspto-grants-2007_06
Patent number
US07229999B2

Reaction notes

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