Triethylamine → (S)-tert-butyl (1-(5-bromo-2-(1H-1,2,4-triazol-1-yl)pyrimidin-4-yl)-2-(3,5-difluorophenyl)ethyl)carbamate

HRID 2170356노트

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HRID 2170356 반응식
[Br:1][C:2]1[C:3]([C@@H:12]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:13][C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([F:21])[CH:15]=2)=[N:4][C:5](S(C)(=O)=O)=[N:6][CH:7]=1.[NH:30]1[CH:34]=[N:33][CH:32]=[N:31]1.C(N(CC)CC)C>CN(C=O)C>[Br:1][C:2]1[C:3]([C@@H:12]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:13][C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([F:21])[CH:15]=2)=[N:4][C:5]([N:30]2[CH:34]=[N:33][CH:32]=[N:31]2)=[N:6][CH:7]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 92571H-1,2,4-TriazoleHCID 90290216(S)-tert-butyl (1-(5-bromo-2-(methylsulfonyl)pyrimidin-4-yl)-2-(3,5-difluorophenyl)ethyl)carbamate

생성물 1

HCID 90290151(S)-tert-butyl (1-(5-bromo-2-(1H-1,2,4-triazol-1-yl)pyrimidin-4-yl)-2-(3,5-difluorophenyl)ethyl)carbamate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
120 °C

실험 절차

In a microwave tube were charged with compound 23B (100 mg, 0.2 mmol), 1H-1,2,4-triazole (42 mg, 0.6 mmol), triethylamine (84 μL, 0.6 mmol) and DMF (0.6 mL, The mixture was heated up to 120° C. for 15 min in a Microwave Synthesizer. After cooled down, it was partitioned between ethyl acetate and 5% of LiCl aqueous solution. The organic layer was separated and concentrated. The residue was purified on silica gel chromatography eluting with ethyl acetate and hexanes to afford the title compound. MS (m/z) 481.21 [M+H]+.

후처리

  1. temperatureAfter cooled down
  2. customit was partitioned between ethyl acetate and 5% of LiCl aqueous solution
  3. customThe organic layer was separated
  4. concentrationconcentrated
  5. customThe residue was purified on silica gel chromatography
  6. washeluting with ethyl acetate and hexanes

출처 및 근거

ORD 기록
ord-ec00d70c8fe542ddbb353012489ffe9b
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09050344B2

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