HCID 58482986, compound → HCID 58483020, compound

HRID 238964Notes

Reaction equation

HRID 238964 reaction equation
C([O:8][CH2:9][CH2:10][C:11]1[N:15]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2[C:23]([F:26])([F:25])[F:24])[C:14]([CH3:27])=[C:13]([C:28]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([S:37]([CH3:40])(=[O:39])=[O:38])=[CH:33][CH:32]=2)=[O:29])[CH:12]=1)C1C=CC=CC=1>CO>[F:22][C:19]1[CH:20]=[CH:21][C:16]([N:15]2[C:11]([CH2:10][CH2:9][OH:8])=[CH:12][C:13]([C:28]([NH:30][C:31]3[CH:36]=[CH:35][C:34]([S:37]([CH3:40])(=[O:39])=[O:38])=[CH:33][CH:32]=3)=[O:29])=[C:14]2[CH3:27])=[C:17]([C:23]([F:24])([F:26])[F:25])[CH:18]=1

Participants

3

Reactant 1

HCID 58482986HCID 58482986, compound

Product 1

HCID 58483020HCID 58483020, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-[2-(benzyloxy)ethyl]-1-[4-fluoro-2-(trifluoromethyl)phenyl]-2-methyl-N-[4-(methylsulfonyl)phenyl]-1H-pyrrole-3-carboxamide (220 mg, 0.38 mmol) in MeOH (3 mL), Pd(OH)2—C (20 mg) was added and stirred overnight under H2 atmosphere at room temperature. After the reaction, Pd(OH)2—C was filtered off and the solvent was evaporated. The residue was purified over silica gel (AcOEt/n-hexane, 9:1 v/v) to give the atropisomeric mixture of the title compound (170 mg, 92%) as a foam.

Workup

  1. filtrationwas filtered off
  2. customthe solvent was evaporated
  3. customThe residue was purified over silica gel (AcOEt/n-hexane, 9:1 v/v)
  4. customto give

Sources & evidence

ORD record
ord-701438405de54fc7acf6f05b7edb3180
Source dataset
uspto-grants-2014_02
Patent number
US08642640B2

Reaction notes

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