Trifluoroacetic acid → N-Methyl-N-[6-(1H-pyrrol-2-yl)-4-o-tolyl-pyridin-3-yl]-3,5-bis-trifluoromethyl-benzamide

HRID 878110Notes

Reaction equation

HRID 878110 reaction equation
C(OC([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13]1[CH:18]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:25])[C:16]([N:26]([C:28](=[O:43])[C:29]2[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[C:31]([C:39]([F:42])([F:41])[F:40])[CH:30]=2)[CH3:27])=[CH:15][N:14]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:27][N:26]([C:16]1[CH:15]=[N:14][C:13]([C:9]2[NH:8][CH:12]=[CH:11][CH:10]=2)=[CH:18][C:17]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH3:25])[C:28](=[O:43])[C:29]1[CH:30]=[C:31]([C:39]([F:41])([F:42])[F:40])[CH:32]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:34]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 866707352-{5-[(3,5-Bis-trifluoromethyl-benzoyl)-methyl-amino]-4-o-tolyl-pyridin-2-yl}-pyrrole-1-carboxylic acid tert-butyl ester

Product 1

HCID 60197804N-Methyl-N-[6-(1H-pyrrol-2-yl)-4-o-tolyl-pyridin-3-yl]-3,5-bis-trifluoromethyl-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-{5-[(3,5-bis-trifluoromethyl-benzoyl)-methyl-amino]-4-o-tolyl-pyridin-2-yl}-pyrrole-1-carboxylic acid tert-butyl ester (39 mg, 64.6 μmol) in CH2Cl2 (2 mL) was added TFA (2 mL) at 0° C. The reaction mixture was stirred for at room temperature for 1 hour and then concentrated under vacuum. The residue was poured on 30 mL aqueous NaHCO3 solution and 30 mL EtOAc and the layers were separated. The aqueous layer was extracted a second time with 30 mL EtOAc. The organic layers were washed with 30 mL brine, dried over MgSO4, filtered and concentrated under vacuum. Light yellow solid (32 mg, 98%). MS (ESI): m/z=504.151 [M+H]+.

Workup

  1. concentrationconcentrated under vacuum
  2. additionThe residue was poured on 30 mL aqueous NaHCO3 solution and 30 mL EtOAc
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted a second time with 30 mL EtOAc
  5. washThe organic layers were washed with 30 mL brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-23587410245e4a63b341c50978680da9
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

Loading…