Cyclopropanecarbonyl chloride → Tert-butyl [2-chloro-5-({2-[(cyclopropylcarbonyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}oxy)phenyl]carbamate

HRID 1874499

반응식

HRID 1874499 반응식
[NH2:1][C:2]1[N:26]=[C:5]2[CH:6]=[CH:7][C:8]([O:10][C:11]3[CH:12]=[CH:13][C:14]([Cl:25])=[C:15]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH:16]=3)=[CH:9][N:4]2[N:3]=1.[CH:27]1([C:30](Cl)=[O:31])[CH2:29][CH2:28]1>CN(C)C(=O)C.C(=O)([O-])O.[Na+]>[Cl:25][C:14]1[CH:13]=[CH:12][C:11]([O:10][C:8]2[CH:7]=[CH:6][C:5]3[N:4]([N:3]=[C:2]([NH:1][C:30]([CH:27]4[CH2:29][CH2:28]4)=[O:31])[N:26]=3)[CH:9]=2)=[CH:16][C:15]=1[NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:21])[CH3:22]

참가 물질

5

반응물 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 57749084Tert-butyl {5-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]-2-chlorophenyl}carbamate

생성물 1

HCID 57749186Tert-butyl [2-chloro-5-({2-[(cyclopropylcarbonyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}oxy)phenyl]carbamate수율 87%

시약·촉매·용매 2

HCID 31374Dimethylacetamide용매HCID 516892Sodium Bicarbonate용매

실험 절차

To a solution of tert-butyl {5-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]-2-chlorophenyl}carbamate (5.49 g, 14.60 mmol) in N,N-dimethylacetamide (40 mL) was added cyclopropanecarbonyl chloride (1.50 mL, 16.5 mmol) at 0° C., and the mixture was stirred at room temperature for 14 hr. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was washed with ethyl acetate-hexane to give the title compound (5.61 g, 87%) as a white solid.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltrated
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. washthe residue was washed with ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-eee8aad5a4004df3852deb4f3d254967
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304557B2

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