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

HRID 44415

反応式

HRID 44415 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21875418Pyridine methylene chloride溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-0be25a15013c4cb8b8bae2691e2304e5
出典データセット
uspto-grants-2013_09
特許番号
US08541426B2

関連ノート

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