Cyclopropanecarbonyl chloride → Tert-butyl [3-({2-[(cyclopropylcarbonyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}oxy)-4-methylphenyl]carbamate

HRID 1800412

반응식

HRID 1800412 반응식
[C:1]([O:5][C:6](=[O:26])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([O:15][C:16]2[CH:17]=[CH:18][C:19]3[N:20]([N:22]=[C:23]([NH2:25])[N:24]=3)[CH:21]=2)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH:27]1([C:30](Cl)=[O:31])[CH2:29][CH2:28]1>CN(C)C(=O)C.O>[C:1]([O:5][C:6](=[O:26])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([O:15][C:16]2[CH:17]=[CH:18][C:19]3[N:20]([N:22]=[C:23]([NH:25][C:30]([CH:27]4[CH2:29][CH2:28]4)=[O:31])[N:24]=3)[CH:21]=2)[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 57749391Tert-butyl {3-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]-4-methylphenyl}carbamate

생성물 1

HCID 57749284Tert-butyl [3-({2-[(cyclopropylcarbonyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}oxy)-4-methylphenyl]carbamate수율 89%

시약·촉매·용매 2

HCID 962Water용매HCID 31374Dimethylacetamide용매

실험 절차

To a solution of tert-butyl{3-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]-4-methylphenyl}carbamate (1.50 g, 4.22 mmol) in N,N-dimethylacetamide (5 mL) was added with stirring cyclopropanecarbonyl chloride (1.15 mL, 12.7 mmol) under ice-cooling, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with water, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the insoluble material was filtered off. The filtrate was concentrated under reduced pressure, and the residue was collected by filtration and washed with ethyl acetate and hexane to give the title compound (1.59 g, 89%) as a white compound.

후처리

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationthe insoluble material was filtered off
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. filtrationthe residue was collected by filtration
  8. washwashed with ethyl acetate and hexane

출처 및 근거

ORD 기록
ord-52842c56ed5d4060ac1f3020a31c13db
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08344135B2

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