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

HRID 2244385ノート

反応式

HRID 2244385 の反応式
[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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-25c157ce7a6943a09cf07b3505911f27
出典データセット
uspto-grants-2010_03
特許番号
US07678818B2

反応ノート

読み込み中…