Acetyl chloride → N-(5-{[2-(acetylamino)[1,3]thiazolo[5,4-b]pyridin-5-yl]oxy}-2-chlorophenyl)-2,2,2-trifluoroacetamide

HRID 1800628노트

반응식

HRID 1800628 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.[C:26](Cl)(=[O:28])[CH3:27]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1.C(OCC)(=O)C.O>[C:26]([NH: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:22])([F:21])[F:23])[CH:17]=1)[N:5]=2)(=[O:28])[CH3:27]

참가 물질

7

반응물 2

HCID 6367Acetyl chlorideHCID 57384282N-{5-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-2-chlorophenyl}-2,2,2-trifluoroacetamide

생성물 1

HCID 86646052N-(5-{[2-(acetylamino)[1,3]thiazolo[5,4-b]pyridin-5-yl]oxy}-2-chlorophenyl)-2,2,2-trifluoroacetamide수율 85%

시약·촉매·용매 4

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 1049Pyridine용매HCID 8857Ethyl Acetate용매

실험 절차

N-{5-[(2-Amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-2-chlorophenyl}-2,2,2-trifluoroacetamide (1.8 g, 4.63 mmol) and N,N-dimethylpyridine-4-amine (566 mg, 4.63 mmol) were dissolved in pyridine (9.25 mL), acetyl chloride (0.658 mL, 9.25 mmol) was added dropwise under ice-cooling, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was diluted with ethyl acetate (80 mL)/water (50 mL), and the organic layer was collected, and washed with saturated brine (50 mL). The mixture was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residual solid was crystallized from toluene/diisopropyl ether (1:3), collected by filtration, and dried to give the title compound (1.69 g, 85%) as a pale-yellow solid.

후처리

  1. temperaturecooling
  2. customthe organic layer was collected
  3. washwashed with saturated brine (50 mL)
  4. dry with materialThe mixture was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residual solid was crystallized from toluene/diisopropyl ether (1:3)
  7. filtrationcollected by filtration
  8. customdried

출처 및 근거

ORD 기록
ord-7a8a1ca44c5c46538feebed33705392a
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08344135B2

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