Methanol → N-[5-(3-amino-4-chlorophenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]acetamide

HRID 1800629노트

반응식

HRID 1800629 반응식
[BH4-].[Na+].CO.[C:5]([NH:8][C:9]1[S:10][C:11]2[C:16]([N:17]=1)=[CH:15][CH:14]=[C:13]([O:18][C:19]1[CH:20]=[CH:21][C:22]([Cl:32])=[C:23]([NH:25]C(=O)C(F)(F)F)[CH:24]=1)[N:12]=2)(=[O:7])[CH3:6]>C(O)C.C(OCC)(=O)C>[NH2:25][C:23]1[CH:24]=[C:19]([CH:20]=[CH:21][C:22]=1[Cl:32])[O:18][C:13]1[N:12]=[C:11]2[S:10][C:9]([NH:8][C:5](=[O:7])[CH3:6])=[N:17][C:16]2=[CH:15][CH:14]=1

참가 물질

6

반응물 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 86646052N-(5-{[2-(acetylamino)[1,3]thiazolo[5,4-b]pyridin-5-yl]oxy}-2-chlorophenyl)-2,2,2-trifluoroacetamide

생성물 1

HCID 86646053N-[5-(3-amino-4-chlorophenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]acetamide수율 50%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

실험 절차

Sodium borohydride (2.45 g, 64.8 mmol) was suspended in ethanol (43 mL), and methanol (29 mL) was slowly added. To the obtained reaction mixture was added N-(5-{[2-(acetylamino)[1,3]thiazolo[5,4-b]pyridin-5-yl]oxy}-2-chlorophenyl)-2,2,2-trifluoroacetamide (1.5 g, 3.48 mmol) powder in small portions under cooling in a water bath, and then, the mixture was stirred at room temperature for 1 hr. The reaction mixture was diluted with ethyl acetate (100 mL), and partitioned with water (50 mL), and the organic layer was concentrated under reduced pressure. The residue was diluted with ethyl acetate (80 mL), and washed with saturated brine (80 mL). The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=40/60→100/0), and triturated with diisopropyl ether to give the title compound (0.58 g, 50%) as a white solid.

후처리

  1. customTo the obtained reaction mixture
  2. temperatureunder cooling in a water bath
  3. custompartitioned with water (50 mL)
  4. concentrationthe organic layer was concentrated under reduced pressure
  5. additionThe residue was diluted with ethyl acetate (80 mL)
  6. washwashed with saturated brine (80 mL)
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=40/60→100/0)
  10. customtriturated with diisopropyl ether

출처 및 근거

ORD 기록
ord-204ed57e169842cd9ebc71dd3dc4e892
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08344135B2

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