Trifluoroacetic acid → 5-(5-chloro-2-fluorophenyl)-N-cyclohexyl-2-methyl-1-(pyrrolidin-2-ylmethyl)pyrrole-3-carboxamide;2,2,2-trifluoroacetic acid

HRID 229878Notes

Reaction equation

HRID 229878 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][N:14]1[C:18]([C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=2[F:26])=[CH:17][C:16]([C:27](=[O:35])[NH:28][CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)=[C:15]1[CH3:36])=O)(C)(C)C.[C:37]([OH:43])([C:39]([F:42])([F:41])[F:40])=[O:38]>C(Cl)Cl>[F:40][C:39]([F:42])([F:41])[C:37]([OH:43])=[O:38].[CH:29]1([NH:28][C:27]([C:16]2[CH:17]=[C:18]([C:19]3[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=3[F:26])[N:14]([CH2:13][CH:9]3[CH2:10][CH2:11][CH2:12][NH:8]3)[C:15]=2[CH3:36])=[O:35])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 116920862-[5-(5-Chloro-2-fluoro-phenyl)-3-cyclohexylcarbamoyl-2-methyl-pyrrol-1-ylmethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 115482765-(5-chloro-2-fluorophenyl)-N-cyclohexyl-2-methyl-1-(pyrrolidin-2-ylmethyl)pyrrole-3-carboxamide;2,2,2-trifluoroacetic acidYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[5-(5-chloro-2-fluoro-phenyl)-3-cyclohexylcarbamoyl-2-methyl-pyrrol-1-ylmethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (51 mg) in methylene chloride (1 mL) was added at 0° C. TFA (0.5 mL). After 3 hours the volatiles were evacuated in vacuo and the residue was azeotroped with ethyl acetate (3×) and dried on high vacuum overnight to afford the desired title compound (50 mg, 95%) as a pale yellow solid, MS (ISP) 418.1 (M+H)+.

Workup

  1. customAfter 3 hours the volatiles were evacuated in vacuo
  2. customthe residue was azeotroped with ethyl acetate (3×)
  3. customdried on high vacuum overnight

Sources & evidence

ORD record
ord-c25d46dc87434e51bb9f938853b64399
Source dataset
uspto-grants-2009_07
Patent number
US07563910B2

Reaction notes

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