Methanol → HCID 90407848, compound

HRID 2277547Notes

Reaction equation

HRID 2277547 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][N:10]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[C:13]([C:22]2[CH:27]=[C:26]([C:28]#N)[CH:25]=[CH:24][N:23]=2)[N:12]=[CH:11]1.[OH-:30].[Na+].C[OH:33]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][N:10]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[C:13]([C:22]2[CH:27]=[C:26]([C:28]([OH:33])=[O:30])[CH:25]=[CH:24][N:23]=2)[N:12]=[CH:11]1

Participants

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 90407681HCID 90407681, compound

Product 1

HCID 90407848HCID 90407848, compoundYield 43%

Procedure

A mixture of 2-[1-[2-(2-chlorophenyl)ethyl]-5-(4-fluorophenyl)imidazol-4-yl]pyridine-4-carbonitrile (1 eq) and NaOH (5 eq, 2 M) in MeOH was refluxed overnight, concentrated and acidified to pH=3-4, purified by HPLC to give the title compound (43%). 1H NMR (300 MHz, CD3OD): δ 3.07 (2H, t, J=6.6 Hz), 4.27 (2H, t, J=6.6 Hz), 7.00-7.33 (8H, m), 7.68 (1H, d, J=5.1 Hz), 7.93-7.95 (2H, m), 8.52 (1H, d, J=4.8 Hz). [M+H] Calc'd for C23H17ClFN3O2, 422. Found, 422.

Workup

  1. temperaturewas refluxed overnight
  2. concentrationconcentrated
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-cc76426066674c09b6071d13b986057d
Source dataset
uspto-grants-2015_09
Patent number
US09133166B2

Reaction notes

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