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

HRID 1629783ノート

反応式

HRID 1629783 の反応式
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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0088f7f952354de3ab807a912d16be90
出典データセット
uspto-grants-2014_07
特許番号
US08791091B2

反応ノート

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