Trifluoroacetic acid → HCID 10302116, compound

HRID 1835343Notes

Reaction equation

HRID 1835343 reaction equation
C(OC([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[CH3:26])[C:17]([C:27](=[O:45])[N:28]([CH2:30][C:31]3[CH:36]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:34]=[C:33]([C:41]([F:44])([F:43])[F:42])[CH:32]=3)[CH3:29])=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[F:40][C:37]([F:38])([F:39])[C:35]1[CH:36]=[C:31]([CH:32]=[C:33]([C:41]([F:42])([F:43])[F:44])[CH:34]=1)[CH2:30][N:28]([CH3:29])[C:27]([C:17]1[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:26])=[CH:19][C:14]([C:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=2)=[N:15][CH:16]=1)=[O:45]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86584823HCID 86584823, compound

Product 1

HCID 10302116HCID 10302116, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 258 mg (0.407 mmol) 5-[(3,5-bis-trifluoromethyl-benzyl)-methyl-carbamoyl]-4-o-tolyl-3′,6′-dihydro-2′H-[2,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester (Example 41) and 0.26 ml (3.2 mmol) trifluoroacetic acid in 2 ml dichloromethane was heated at reflux for 4 h. After cooling to room temperature the mixture was diluted with dichloromethane and washed with 1N aqueous sodium hydroxide solution. The aqueous layer was extracted with three portions of dichloromethane. The combined organic extracts were dried over sodium sulfate and concentrated. Column chromatography afforded 135 mg (62%) of the title compound as a light brown solid.

Workup

  1. temperatureat reflux for 4 h
  2. washwashed with 1N aqueous sodium hydroxide solution
  3. extractionThe aqueous layer was extracted with three portions of dichloromethane
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3cc8b15fbf8e4326a681238d97cd038f
Source dataset
uspto-grants-2004_08
Patent number
US06770637B2

Reaction notes

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