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HCID 91325177, 화합물 → N-[5-(5-amino-2-chloro-4-fluorophenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]propanamide

HRID 1800615
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HRID 1800615 반응식
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([O:14][C:15]2[N:20]=[C:19]3[S:21][C:22]([NH:24][C:25](=[O:28])[CH2:26][CH3:27])=[N:23][C:18]3=[CH:17][CH:16]=2)[C:11]([Cl:29])=[CH:10][C:9]=1[F:30])(C)(C)C>FC(F)(F)C(O)=O>[NH2:7][C:8]1[C:9]([F:30])=[CH:10][C:11]([Cl:29])=[C:12]([CH:13]=1)[O:14][C:15]1[N:20]=[C:19]2[S:21][C:22]([NH:24][C:25](=[O:28])[CH2:26][CH3:27])=[N:23][C:18]2=[CH:17][CH:16]=1
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3

반응물 1

HCID 91325177HCID 91325177, 화합물

생성물 1

HCID 86646047N-[5-(5-amino-2-chloro-4-fluorophenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]propanamide수율 79.5%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

A mixture of tert-butyl(4-chloro-2-fluoro-5-{[2-(propanoylamino)[1,3]thiazolo[5,4-b]pyridin-5-yl]oxy}phenyl)carbamate (1.26 g, 2.70 mmol) and trifluoroacetic acid (10 mL) was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate (100 mL). The solution was washed with aqueous sodium hydrogen carbonate solution (30 mL×2) and saturated brine (10 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=67/33→0/100) to give the title compound (787 mg, 79%) as white crystals.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate (100 mL)
  3. washThe solution was washed with aqueous sodium hydrogen carbonate solution (30 mL×2) and saturated brine (10 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=67/33→0/100)

출처 및 근거

ORD 기록
ord-6f74564a737a49a698fffd62ba6d788c
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08344135B2

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