Cyclopentanecarbonyl chloride → N-(5-chloro-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)cyclopentanecarboxamide

HRID 875913노트

반응식

HRID 875913 반응식
C(N(C(C)C)C(C)C)C.[CH:10]1([C:15](Cl)=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11]1.[Cl:18][C:19]1[C:20]([F:29])=[C:21]2[C:27]([NH2:28])=[CH:26][NH:25][C:22]2=[N:23][CH:24]=1>C1COCC1>[Cl:18][C:19]1[C:20]([F:29])=[C:21]2[C:27]([NH:28][C:15]([CH:10]3[CH2:14][CH2:13][CH2:12][CH2:11]3)=[O:16])=[CH:26][NH:25][C:22]2=[N:23][CH:24]=1

참가 물질

5

반응물 3

HCID 78284Cyclopentanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 581955655-chloro-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine

생성물 1

HCID 60205684N-(5-chloro-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)cyclopentanecarboxamide수율 61.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

N-Ethyl-N-isopropylpropan-2-amine (279 mg, 2.16 mmol) followed by cyclopentanecarbonyl chloride (143 mg, 1.08 mmol) were added dropwise to 5-chloro-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine (200 mg, 1.08 mmol) in THF (10 mL) at 0° C. The reaction mixture was stirred at 0° C. for 1 hour and then concentrated to dryness. The residue was triturated in water and then filtered. The solid was washed with ACN and dried under vacuum to provide N-(5-chloro-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)cyclopentanecarboxamide (186 mg, 61% yield) as a solid.

후처리

  1. concentrationconcentrated to dryness
  2. customThe residue was triturated in water
  3. filtrationfiltered
  4. washThe solid was washed with ACN
  5. customdried under vacuum

출처 및 근거

ORD 기록
ord-07846139100748baa04ca5be3dd98331
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08981085B2

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