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Cyclopropanecarbonyl chloride → N-(5-{4-chloro-3-[(trifluoroacetyl)amino]phenoxy}[1,3]thiazolo[5,4-b]pyridin-2-yl)cyclopropanecarboxamide

HRID 2366780
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HRID 2366780 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]([Cl:25])=[C:16]([NH:18][C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])[CH:17]=1)[N:5]=2.[CH:26]1([C:29](Cl)=[O:30])[CH2:28][CH2:27]1.C(=O)([O-])O.[Na+]>N1C=CC=CC=1.C(OCC)(=O)C>[Cl:25][C:15]1[CH:14]=[CH:13][C:12]([O:11][C:6]2[N:5]=[C:4]3[S:3][C:2]([NH:1][C:29]([CH:26]4[CH2:28][CH2:27]4)=[O:30])=[N:10][C:9]3=[CH:8][CH:7]=2)=[CH:17][C:16]=1[NH:18][C:19](=[O:24])[C:20]([F:22])([F:21])[F:23]
참가 물질실험 절차후처리출처 및 근거반응 노트

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HCID 77637Cyclopropanecarbonyl chlorideHCID 516892Sodium BicarbonateHCID 57384282N-{5-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-2-chlorophenyl}-2,2,2-trifluoroacetamide

생성물 1

HCID 57387328N-(5-{4-chloro-3-[(trifluoroacetyl)amino]phenoxy}[1,3]thiazolo[5,4-b]pyridin-2-yl)cyclopropanecarboxamide수율 59%

시약·촉매·용매 2

HCID 1049
Pyridine
용매
HCID 8857Ethyl Acetate용매

실험 절차

N-{5-[(2-Amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-2-chlorophenyl}-2,2,2-trifluoroacetamide (5.0 g, 12.9 mmol) was dissolved in pyridine (25 mL), cyclopropanecarbonyl chloride (1.28 ml, 14.2 mmol) was added dropwise under ice-cooling, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was treated with aqueous sodium hydrogen carbonate solution (100 mL), and diluted with ethyl acetate (100 mL). The organic layer was separated, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residual solid was crystallized from ethyl acetate (30 mL), collected by filtration, and dried to give the title compound (3.46 g, 59%) as a colorless powder.

후처리

  1. temperaturecooling
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residual solid was crystallized from ethyl acetate (30 mL)
  6. filtrationcollected by filtration
  7. customdried

출처 및 근거

ORD 기록
ord-eb7a0d0df78c4092b729e1281cdfcc42
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08697874B2

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