Cyclohexylamine → N-Cyclohexyl-5-(methylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-amine

HRID 1506211노트

반응식

HRID 1506211 반응식
Cl[C:2]1[C:7]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:6][N:5]=[C:4]2[N:12]([Si](C(C)C)(C(C)C)C(C)C)[CH:13]=[CH:14][C:3]=12.[CH:25]1([NH2:31])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.C(N(CC)C(C)C)(C)C>O>[CH:25]1([NH:31][C:2]2[C:3]3[CH:14]=[CH:13][NH:12][C:4]=3[N:5]=[CH:6][C:7]=2[S:8]([CH3:11])(=[O:9])=[O:10])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

참가 물질

5

반응물 3

HCID 7965CyclohexylamineHCID 81531DiisopropylethylamineHCID 712584634-Chloro-5-(methylsulfonyl)-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine

생성물 1

HCID 71258218N-Cyclohexyl-5-(methylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-amine수율 15%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

4-Chloro-5-(methylsulfonyl)-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (61 mg, 0.16 mmol) in cyclohexylamine (200 μL, 1.74 mmol) was stirred with N,N-diisopropylethylamine (40 μL, 0.23 mmol) at 120° C. for 30 minutes The reaction mixture was allowed to cool to room temperature and, after addition of water, extracted with chloroform, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1→5/1 (v/v)) to give the title compound as a colorless solid (7.0 mg, yield 15%).

후처리

  1. extractionextracted with chloroform
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1→5/1 (v/v))

출처 및 근거

ORD 기록
ord-e6cdc9bfba7f4063bc1439830d192745
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216999B2

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