HCID 58760954, compound → HCID 21868784, compound

HRID 857486Notes

Reaction equation

HRID 857486 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)[N:9]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])[C:10]=1[CH2:11][NH:12][CH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:5])C.[OH-].[K+].C1COCC1>>[Cl:31][C:28]1[CH:27]=[CH:26][C:25]([C:8]2[N:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[F:24])[C:10]([CH2:11][NH:12][CH:13]3[CH2:14][CH2:15][CH2:16][CH2:17]3)=[C:6]([C:4]([OH:5])=[O:3])[N:7]=2)=[CH:30][CH:29]=1

Participants

3

Reactant 2

HCID 58760954HCID 58760954, compoundHCID 67897491HCID 67897491, compound

Product 1

HCID 21868784HCID 21868784, compoundYield 113.6%

Procedure

A solution of 2-(4-chloro-phenyl)-5-cyclopentylaminomethyl-1-(2-fluoro-phenyl)-1H-imidazole-4-carboxylic acid ethyl ester I-5f (1.2 g, 2.68 mmol) in 1:2 1M KOH/THF was stirred at 55° C. for 17 hours. The reaction mixture was concentrated under vacuum and acidified to pH˜1 with concentrated hydrochloric acid. The residue was slurried in EtOH and filtered to remove KCl. The filtrate was concentrated under vaccum to give I-5k as an off-white solid (1.26 g, 97%): +APCI MS (M+1) 414.0.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. filtrationfiltered
  3. customto remove KCl
  4. concentrationThe filtrate was concentrated under vaccum

Sources & evidence

ORD record
ord-16aa4355c5bb459fa2c7847401af9d31
Source dataset
uspto-grants-2006_12
Patent number
US07145012B2

Reaction notes

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