Acetic Acid → 5-Methyl-2-{4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl}cyclopent-2-en-1-one

HRID 1895990ノート

反応式

HRID 1895990 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[C:9][CH:10]=[C:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[N:3]=1.[CH3:17][CH:18]1[CH2:22][CH2:21][C:20](=O)[C:19]1=[O:24].C(O)(=O)C>C(O)C>[CH3:17][CH:18]1[C:19](=[O:24])[C:20]([N:14]2[CH2:13][CH2:12][C:11](=[CH:10][C:9]#[C:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[N:3]=3)[CH2:16][CH2:15]2)=[CH:21][CH2:22]1

参加物

5

反応物 3

HCID 176Acetic AcidHCID 612093-Methyl-1,2-cyclopentanedioneHCID 875504022-Methyl-6-(3-piperidin-4-ylideneprop-1-ynyl)pyridine

生成物 1

HCID 251819235-Methyl-2-{4-[3-(6-methylpyridin-2-yl)prop-2-ynylidene]piperidin-1-yl}cyclopent-2-en-1-one

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of the Compound of Example 3 (500 mg, 2.36 mmol), 3-methyl-1,2-cyclopentanedione (350 mg, 3.11 mmol), acetic acid (0.18 mL, 3.11 mmol) in ethanol (10 mL) was refluxed for 8 h. The reaction mixture was evaporated, poured into water and extracted with EtOAc. The combined organic layers were washed with brine, dried on Na2SO4 and evaporated to dryness in vacuo to afford a residue, which was purified by automated flash liquid chromatography (Horizon™-Biotage) eluting with Petroleum Ether-EtOAc 85:15, affording the title product as a brown solid.

後処理

  1. temperaturewas refluxed for 8 h
  2. customThe reaction mixture was evaporated
  3. additionpoured into water
  4. extractionextracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. customdried on Na2SO4
  7. customevaporated to dryness in vacuo
  8. customto afford a residue, which
  9. customwas purified by automated flash liquid chromatography (Horizon™-Biotage)
  10. washeluting with Petroleum Ether-EtOAc 85:15

出典と根拠

ORDレコード
ord-6180f48b8c914cc6a17af5fac2fa0775
出典データセット
uspto-grants-2013_08
特許番号
US08518916B2

反応ノート

読み込み中…