2-Bromoethanol → N-(3,5-Bis-trifluoromethyl-benzyl)-6-[4-(2-hydroxy-ethyl)-piperazin-1-yl]-N-methyl-4-o-tolyl-nicotinamide

HRID 379396

반응식

HRID 379396 반응식
[F:1][C:2]([F:38])([F:37])[C:3]1[CH:4]=[C:5]([CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=1)[CH2:6][N:7]([CH3:29])[C:8](=[O:28])[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][C:12]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[N:11][CH:10]=1.Br[CH2:40][CH2:41][OH:42].C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>C(#N)C>[F:38][C:2]([F:37])([F:1])[C:3]1[CH:4]=[C:5]([CH:30]=[C:31]([C:33]([F:35])([F:36])[F:34])[CH:32]=1)[CH2:6][N:7]([CH3:29])[C:8](=[O:28])[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][C:12]([N:22]2[CH2:23][CH2:24][N:25]([CH2:40][CH2:41][OH:42])[CH2:26][CH2:27]2)=[N:11][CH:10]=1

참가 물질

6

반응물 4

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 10280286N-(3,5-bis-trifluoromethyl-benzyl)-N-methyl-6-piperazin-1-yl-4-o-tolyl-nicotinamide

생성물 1

HCID 9938188N-(3,5-Bis-trifluoromethyl-benzyl)-6-[4-(2-hydroxy-ethyl)-piperazin-1-yl]-N-methyl-4-o-tolyl-nicotinamide수율 78.7%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
45 °C

실험 절차

A mixture of 100 mg (0.186 mmol) N-(3,5-bis-trifluoromethyl-benzyl)-N-methyl-6-piperazin-1-yl-4-o-tolyl-nicotinamide (Example 53), 0.030 ml (0.42 mmol)2-bromo-ethanol and 46 mg (0.33 mmol) potassium carbonate in 2 ml acetonitrile was stirred at 45° C. for 70 h. After cooling to room temperature 10 ml 1 N sodium hydroxide solution were added. Extraction with 3 15-ml portions of ethyl acetate, drying with sodium sulfate and concentration gave 138 mg of the crude product. Flash column chromatography afforded 85 mg (78.6%) of the title compound as a white solid.

후처리

  1. additionwere added
  2. extractionExtraction with 3 15-ml portions of ethyl acetate
  3. dry with materialdrying with sodium sulfate and concentration
  4. customgave 138 mg of the crude product

출처 및 근거

ORD 기록
ord-911c5194d69542a1ab0ef605ba97880a
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06297375B1

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