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

HRID 1594376ノート

反応式

HRID 1594376 の反応式
[CH3:1][N:2]([C@@H:12]1[C@H: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][C@@H:17]1[CH2:16][CH2:15][N:14]([C:19](=[O:21])[CH3:20])[CH2:13][C@@H: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 23401507N-Methyl-N-[(3R,4R)-4-methyl-3-piperidinyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine

生成物 1

HCID 692220831-((3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)ethanone収率 15.3%

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 B (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 g (15%) of the title compound as a colorless oil.

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-ceb5f37bcf5e4ff18ea7b8a972a45824
出典データセット
uspto-grants-2007_11
特許番号
US07301023B2

反応ノート

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