Ethanolamine → N-(3,5-Bis-trifluoromethyl-benzyl)-6-(2-hydroxy-ethylamino)-N-methyl-4-o-tolyl-nicotinamide

HRID 1168318노트

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HRID 1168318 반응식
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[CH2:6][N:7]([CH3:24])[C:8](=[O:23])[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](Cl)=[N:11][CH:10]=1.[CH2:34]([CH2:36][NH2:37])[OH:35]>>[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[CH2:6][N:7]([CH3:24])[C:8](=[O:23])[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]([NH:37][CH2:36][CH2:34][OH:35])=[N:11][CH:10]=1

참가 물질

3

반응물 2

HCID 700Ethanolamine2회HCID 10277890N-(3,5-bis-trifluoromethyl-benzyl)-6-chloro-N-methyl-4-o-tolyl-nicotinamide

생성물 1

HCID 10142310N-(3,5-Bis-trifluoromethyl-benzyl)-6-(2-hydroxy-ethylamino)-N-methyl-4-o-tolyl-nicotinamide수율 73.9%

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온도
100 °C

실험 절차

A mixture of 0.837 g (1.72 mmol) N-(3,5-bis-trifluoromethyl-benzyl)-6-chloro-N-methyl-4-o-tolyl-nicotinamide and 5.0 ml (83 mmol) ethanolamine was stirred at 100° C. for 48 h. After cooling to room temperature excess ethanolamine was removed under reduced pressure. The residue was dissolved in a mixture of ethyl acetate and saturated aqueous sodium bicarbonate solution. The layers were separated and the aqueous layer was extracted with two portions of ethyl acetate. The combined organic extracts were washed with saturated aqueous sodium bicarbonate solution and water, dried with sodium sulfate and concentrated to give 0.8 g of crude product. Flash chromatography afforded 0.650 g (73.9%) of the title compound as a white solid. MS m/e (%): 512 (M+H+, 100).

후처리

  1. customwas removed under reduced pressure
  2. dissolutionThe residue was dissolved in a mixture of ethyl acetate and saturated aqueous sodium bicarbonate solution
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with two portions of ethyl acetate
  5. washThe combined organic extracts were washed with saturated aqueous sodium bicarbonate solution and water
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated
  8. customto give 0.8 g of crude product

출처 및 근거

ORD 기록
ord-6b553dab5ce54ec3bd79ab42ef655eba
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06624176B2

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