Formic Acid → (1-(1-Amino-2,2,2-trifluoro-1-(4-(4,4,4-trifluorobutoxy)phenyl)ethyl)cyclopropyl)(4-methoxy-phenyl)methanone

HRID 1629783Notes

Reaction equation

HRID 1629783 reaction equation
C([NH:8][C:9]([C:28]1([C:31]([C:33]2[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=2)=[O:32])[CH2:30][CH2:29]1)([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][C:24]([F:27])([F:26])[F:25])=[CH:16][CH:15]=1)[C:10]([F:13])([F:12])[F:11])C1C=CC=CC=1.C(O)=O>CO.[Pd]>[NH2:8][C:9]([C:28]1([C:31]([C:33]2[CH:34]=[CH:35][C:36]([O:39][CH3:40])=[CH:37][CH:38]=2)=[O:32])[CH2:30][CH2:29]1)([C:14]1[CH:15]=[CH:16][C:17]([O:20][CH2:21][CH2:22][CH2:23][C:24]([F:27])([F:25])[F:26])=[CH:18][CH:19]=1)[C:10]([F:13])([F:12])[F:11]

Participants

5

Reactant 2

HCID 284Formic AcidHCID 86685873(1-(1-(Benzylamino)-2,2,2-trifluoro-1-(4-(4,4,4-trifluorobutoxy)phenyl)ethyl)-cyclopropyl)-(4-methoxyphenyl)methanone

Product 1

HCID 86685874(1-(1-Amino-2,2,2-trifluoro-1-(4-(4,4,4-trifluorobutoxy)phenyl)ethyl)cyclopropyl)(4-methoxy-phenyl)methanoneYield 79.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of Intermediate 14G (6 mg, 10.6 μmol) in MeOH (1 mL) containing 4.4% formic acid was added 10% palladium on carbon (2 mg, 2 μmol). The reaction was stirred at rt overnight. The reaction was filtered through Celite®. The filtrate was made basic with sat'd aq NaHCO3, and then evaporated to remove MeOH. The aqueous residue was diluted with sat'd aq NaCl and extracted with EtOAc. The combined organic extracts were washed with sat'd aq NaCl, dried over Na2SO4, filtered and concentrated to provide Intermediate 14H (4 mg, 71%) as a tan glass. LCMS Anal. Calc'd for C23H23F6NO3 475.42, found [M+H] 476.2.

Workup

  1. filtrationThe reaction was filtered through Celite®
  2. customevaporated
  3. customto remove MeOH
  4. additionThe aqueous residue was diluted with sat'd aq NaCl
  5. extractionextracted with EtOAc
  6. washThe combined organic extracts were washed with sat'd aq NaCl
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-0088f7f952354de3ab807a912d16be90
Source dataset
uspto-grants-2014_07
Patent number
US08791091B2

Reaction notes

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