Hydrogen chloride-ethyl acetate → HCID 89544649, compound

HRID 2283442Notes

Reaction equation

HRID 2283442 reaction equation
C(OC([N:8]1[CH2:12][CH:11]=[C:10]([C:13](=[O:34])[NH:14][C@H:15]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([C:25]([C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)=[O:26])[C:19]=2[F:33])[CH2:16][CH3:17])[CH2:9]1)=O)(C)(C)C.Cl.CCOC(C)=O>>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([C@@H:15]([NH:14][C:13]([C:10]2[CH2:9][NH:8][CH2:12][CH:11]=2)=[O:34])[CH2:16][CH3:17])=[C:19]([F:33])[C:20]=1[C:25]([C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)=[O:26]

Participants

3

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 89544959HCID 89544959, compound

Product 1

HCID 89544649HCID 89544649, compoundYield 61.5%

Procedure

3-{(S)-1-[4-Chloro-2-fluoro-3-(pyridine-3-carbonyl)-phenyl]-propylcarbamoyl}-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester (0.125 g, 0.26 mmol) treated with saturated HCl/EtOAc stirred at ambient for 1 hour, solid filtered off then purified by Prep HPLC to give N-[(1S)-1-{4-chloro-2-fluoro-3-[(pyridin-3-yl)carbonyl]phenyl}propyl]-2,5-dihydro-1H-pyrrole-3-carboxamide (0.062 g), MS: [M+H] 388

Workup

  1. filtrationsolid filtered off
  2. customthen purified by Prep HPLC

Sources & evidence

ORD record
ord-88c75bfad6fe41288416c92dee2aebf5
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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