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

HRID 1629783노트

반응식

HRID 1629783 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0088f7f952354de3ab807a912d16be90
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08791091B2

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