Methanesulfonyl chloride → Methanesulfonic acid 2-(4-{2-[2-(3,5-difluoro-phenyl)-acetylamino]-pentanoylamino}-imidazol-1-yl)-ethyl ester

HRID 553191Notes

Reaction equation

HRID 553191 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH:8]=[C:7]([NH:9][C:10](=[O:27])[CH:11]([NH:15][C:16](=[O:26])[CH2:17][C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[CH:19]=2)[CH2:12][CH2:13][CH3:14])[N:6]=[CH:5]1.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>N1C=CC=CC=1>[F:25][C:20]1[CH:19]=[C:18]([CH2:17][C:16]([NH:15][CH:11]([CH2:12][CH2:13][CH3:14])[C:10]([NH:9][C:7]2[N:6]=[CH:5][N:4]([CH2:3][CH2:2][O:1][S:29]([CH3:28])(=[O:31])=[O:30])[CH:8]=2)=[O:27])=[O:26])[CH:23]=[C:22]([F:24])[CH:21]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 115960342-[2-(3,5-Difluoro-phenyl)-acetylamino]-pentanoic acid [1-(2-hydroxy-ethyl)-1H-imidazol-4-yl]-amide

Product 1

HCID 86600814Methanesulfonic acid 2-(4-{2-[2-(3,5-difluoro-phenyl)-acetylamino]-pentanoylamino}-imidazol-1-yl)-ethyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-[2-(3,5-Difluoro-phenyl)-acetylamino]-pentanoic acid [1-(2-hydroxy-ethyl)-1H-imidazol-4-yl]-amide (1 equiv) was dissolved in pyridine and treated with methansulfonyl chloride (2.2 equiv) at 0° C. The reaction was warmed to rt and stirred for 4 h, quenched with sodium bicarbonate, and extracted with methylene chloride. The extracts were dried and concentrated to provide methanesulfonic acid 2-(4-{2-[2-(3,5-difluoro-phenyl)-acetylamino]-pentanoylamino}-imidazol-1-yl)-ethyl ester which was used without further purification.

Workup

  1. customquenched with sodium bicarbonate
  2. extractionextracted with methylene chloride
  3. customThe extracts were dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5c4b21593ee245dea742f07a7b4cde25
Source dataset
uspto-grants-2011_05
Patent number
US07951958B2

Reaction notes

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