Acetonitrile → N-[(1S)-2-({5-[6-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]-4-fluoro-1-methyl-1H-pyrazol-3-yl}oxy)-1-methylethyl]acetamide

HRID 1026226노트

반응식

HRID 1026226 반응식
[CH:1]1([CH2:4][O:5][C:6]2[CH:28]=[CH:27][C:9]3[N:10]=[C:11]([C:13]4[N:17]([CH3:18])[N:16]=[C:15]([O:19][CH2:20][C@@H:21]([NH:23][C:24](=[O:26])[CH3:25])[CH3:22])[CH:14]=4)[O:12][C:8]=3[CH:7]=2)[CH2:3][CH2:2]1.[B-](F)(F)(F)[F:30].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1.C(#N)C>O>[CH:1]1([CH2:4][O:5][C:6]2[CH:28]=[CH:27][C:9]3[N:10]=[C:11]([C:13]4[N:17]([CH3:18])[N:16]=[C:15]([O:19][CH2:20][C@@H:21]([NH:23][C:24](=[O:26])[CH3:25])[CH3:22])[C:14]=4[F:30])[O:12][C:8]=3[CH:7]=2)[CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 6342AcetonitrileHCID 2724933SelectfluorHCID 67778386N-[(1S)-2-({5-[6-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]-1-methyl-1H-pyrazol-3-yl}oxy)-1-methylethyl]acetamide

생성물 1

HCID 67778849N-[(1S)-2-({5-[6-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]-4-fluoro-1-methyl-1H-pyrazol-3-yl}oxy)-1-methylethyl]acetamide수율 5.5%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
60 °C

실험 절차

A mixture of N-[(1S)-2-({5-[6-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]-1-methyl-1H-pyrazol-3-yl}oxy)-1-methylethyl]acetamide (193 mg), 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane ditetrafluoroborate (427 mg) and acetonitrile (10 mL) was stirred at 60° C. for 7 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The combined organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (11.2 mg).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-116e4b2c2b0a45afadb1b95ed29c0fae
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08729102B2

반응 노트

불러오는 중…