Cyclopropanecarbonyl chloride → 3-(1-cyano-1-methylethyl)-N-[5-({2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)-2-methylphenyl]benzamide

HRID 1800462노트

반응식

HRID 1800462 반응식
[NH2:1][C:2]1[S:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[C:6]([O:11][C:12]1[CH:13]=[CH:14][C:15]([CH3:32])=[C:16]([NH:18][C:19](=[O:31])[C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([C:29]#[N:30])([CH3:28])[CH3:27])[CH:21]=3)[CH:17]=1)[N:5]=2.[CH:33]1([C:36](Cl)=[O:37])[CH2:35][CH2:34]1>N1C=CC=CC=1>[C:29]([C:26]([C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][CH:23]=1)[C:19]([NH:18][C:16]1[CH:17]=[C:12]([O:11][C:6]2[N:5]=[C:4]3[S:3][C:2]([NH:1][C:36]([CH:33]4[CH2:35][CH2:34]4)=[O:37])=[N:10][C:9]3=[CH:8][CH:7]=2)[CH:13]=[CH:14][C:15]=1[CH3:32])=[O:31])([CH3:27])[CH3:28])#[N:30]

참가 물질

4

반응물 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 86646000N-{5-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-2-methylphenyl}-3-(1-cyano-1-methylethyl)benzamide

생성물 1

HCID 595069803-(1-cyano-1-methylethyl)-N-[5-({2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)-2-methylphenyl]benzamide수율 68%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a solution of N-{5-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-2-methylphenyl}-3-(1-cyano-1-methylethyl)benzamide (300 mg, 0.676 mmol) in pyridine (6.0 mL) was added cyclopropanecarbonyl chloride (80 μL, 0.879 mmol), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, and the obtained residue was diluted with ethyl acetate (200 mL), washed with 5% aqueous sodium hydrogen carbonate solution (200 mL), water (200 mL) and saturated brine (200 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=50/50→0/100), and the obtained solution was concentrated under reduced pressure. The residue was recrystallized from ethyl acetate to give the title compound (234 mg, 68%) as a colorless powder.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe obtained residue was diluted with ethyl acetate (200 mL)
  3. washwashed with 5% aqueous sodium hydrogen carbonate solution (200 mL), water (200 mL) and saturated brine (200 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe insoluble material was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=50/50→0/100)
  8. concentrationthe obtained solution was concentrated under reduced pressure
  9. customThe residue was recrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-3a7ac7d207b34a1faf681e820de327bd
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08344135B2

반응 노트

불러오는 중…