Potassium Carbonate → 5-chloro-2-methylamino-N-[4-(3,3,3-trifluoro-2-hydroxy-propoxy)-benzyl]-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-benzamide

HRID 2244385노트

반응식

HRID 2244385 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:31][CH3:32])=[C:6]([CH:30]=1)[C:7]([N:9]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1)[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=1)=[O:8].Br[CH2:34][CH:35]([OH:40])[C:36]([F:39])([F:38])[F:37].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O.[Cl-].[Na+].O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:31][CH3:32])=[C:6]([CH:30]=1)[C:7]([N:9]([CH2:22][C:23]1[CH:24]=[CH:25][C:26]([O:29][CH2:34][CH:35]([OH:40])[C:36]([F:39])([F:38])[F:37])=[CH:27][CH:28]=1)[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:19])[F:20])[CH:13]=1)=[O:8]

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 2206323-Bromo-1,1,1-Trifluoro-2-PropanolHCID 687030505-chloro-N-(4-hydroxy-benzyl)-2-methylamino-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-benzamide

생성물 1

HCID 866152415-chloro-2-methylamino-N-[4-(3,3,3-trifluoro-2-hydroxy-propoxy)-benzyl]-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-benzamide수율 59.3%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

실험 절차

A suspension of 80 mg (0.17 mmol) of 5-chloro-N-(4-hydroxy-benzyl)-2-methylamino-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-benzamide, 40 mg (0.21 mmol) 3-bromo-1,1,1-trifluoro-2-propanol and 57 mg (0.41 mmol) of potassium carbonate in 3 ml DMF was stirred at RT for 65 hours. The reaction mixture was then diluted with 15 ml water and 15 ml brine, and extracted twice with ethylacetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (silica gel; DCM/EtOAc 97:3) to give 58 mg of 5-chloro-2-methylamino-N-[4-(3,3,3-trifluoro-2-hydroxy-propoxy)-benzyl]-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-benzamide (55%) as a light yellow viscous oil. MS (ISP) 575.3 (M+H)+.

후처리

  1. extractionextracted twice with ethylacetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (silica gel; DCM/EtOAc 97:3)

출처 및 근거

ORD 기록
ord-25c157ce7a6943a09cf07b3505911f27
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07678818B2

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