Acetyl chloride → 1-{4-Methyl-3-[methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amino]-piperidin-1-yl}-ethanone

HRID 8704

반응식

HRID 8704 반응식
[CH3:1][N:2]([CH:12]1[CH:17]([CH3:18])[CH2:16][CH2:15][NH:14][CH2:13]1)[C:3]1[C:4]2[CH:11]=[CH:10][NH:9][C:5]=2[N:6]=[CH:7][N:8]=1.[C:19](Cl)(=[O:21])[CH3:20]>ClCCl.N1C=CC=CC=1>[CH3:18][CH:17]1[CH2:16][CH2:15][N:14]([C:19](=[O:21])[CH3:20])[CH2:13][CH:12]1[N:2]([CH3:1])[C:3]1[C:4]2[CH:11]=[CH:10][NH:9][C:5]=2[N:6]=[CH:7][N:8]=1

참가 물질

4

반응물 2

HCID 6367Acetyl chlorideHCID 12084830N-Methyl-N-[(3S,4S)-4-methyl-3-piperidyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine

생성물 1

HCID 120848311-{4-Methyl-3-[methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amino]-piperidin-1-yl}-ethanone수율 15%

시약·촉매·용매 1

HCID 21875418Pyridine methylene chloride용매

실험 절차

To a stirred solution of the product from Method C (0.03 grams, 0.114 mmol) dissolved in 5 mL of 10:1 dichloromethane/pyridine was added (0.018 grams, 0.228 mmol) of acetylchloride and the resulting mixture stirred at room temperature for 18 hours. The reaction mixture was then partitioned between dichloromethane and saturated sodium bicarbonate (NaHCO3). The organic layer was washed again with saturated NaHCO3, dried-over sodium sulfate and concentrated to dryness in vacuo. The residue was purified by preparative thin layer chromatography (PTLC) (silica; 4% methanol in dichloromethane) affording 0.005 mg (15%) of the title compound as a colorless oil. LRMS: 288.1 (M+1).

후처리

  1. customThe reaction mixture was then partitioned between dichloromethane and saturated sodium bicarbonate (NaHCO3)
  2. washThe organic layer was washed again with saturated NaHCO3, dried-over sodium sulfate
  3. concentrationconcentrated to dryness in vacuo
  4. customThe residue was purified by preparative thin layer chromatography (PTLC) (silica; 4% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-dedaa27fb1e14f76bacb2c6dcc3a01b4
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091208B2

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