Phosphorus oxychloride → N-[4-(Cyano-dimethyl-methyl)-2-fluoro-benzyl]-2-(4-fluoro-phenoxy)-nicotinamide

HRID 1297588노트

반응식

HRID 1297588 반응식
[C:1]([C:4]([C:7]1[CH:30]=[CH:29][C:10]([CH2:11][NH:12][C:13](=[O:28])[C:14]2[CH:19]=[CH:18][CH:17]=[N:16][C:15]=2[O:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=[C:9]([F:31])[CH:8]=1)([CH3:6])[CH3:5])(=O)[NH2:2].P(Cl)(Cl)(Cl)=O>>[C:1]([C:4]([CH3:6])([CH3:5])[C:7]1[CH:30]=[CH:29][C:10]([CH2:11][NH:12][C:13](=[O:28])[C:14]2[CH:19]=[CH:18][CH:17]=[N:16][C:15]=2[O:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=[C:9]([F:31])[CH:8]=1)#[N:2]

참가 물질

3

반응물 2

HCID 24813Phosphorus oxychlorideHCID 10295972N-[4-(1-Carbamoyl-1-methyl-ethyl)-2-fluoro-benzyl]-2-(4-fluoro-phenoxy)-nicotinamide

생성물 1

HCID 17832827N-[4-(Cyano-dimethyl-methyl)-2-fluoro-benzyl]-2-(4-fluoro-phenoxy)-nicotinamide수율 82.1%

반응 조건

온도
90 °C

실험 절차

To N-[4-(1-Carbamoyl-1-methyl-ethyl)-2-fluoro-benzyl]-2-(4-fluoro-phenoxy)-nicotinamide (3.00 g) in a 50 mL flask was added phosphorous oxychloride (3.29 mL). The solution was heated for 1 h at 90° C. The solution was then cooled in an ice bath, poured over satd. aq. sodium carbonate (50 mL), then extracted with ethyl acetate (4×100 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo, yielding the title compound (2.36 g).

후처리

  1. temperatureThe solution was then cooled in an ice bath
  2. additionpoured over satd
  3. extractionaq. sodium carbonate (50 mL), then extracted with ethyl acetate (4×100 mL)
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-ebaace09f7c54565877232c0ad3c12a7
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07250518B2

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