Potassium Iodide → Azd-0424

HRID 2374442ノート

反応式

HRID 2374442 の反応式
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([NH:15][C:16]3[C:21]([Cl:22])=[CH:20][N:19]=[C:18]4[O:23][CH2:24][O:25][C:17]=34)=[N:10][CH:11]=[N:12]2)=[C:7]([O:26][CH:27]([CH3:29])[CH3:28])[CH:6]=1.[C:30]([N:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1)(=[O:32])[CH3:31].[I-].[K+]>CC(N(C)C)=O>[C:30]([N:33]1[CH2:38][CH2:37][N:36]([CH2:2][CH2:3][O:4][C:5]2[CH:14]=[C:13]3[C:8]([C:9]([NH:15][C:16]4[C:21]([Cl:22])=[CH:20][N:19]=[C:18]5[O:23][CH2:24][O:25][C:17]=45)=[N:10][CH:11]=[N:12]3)=[C:7]([O:26][CH:27]([CH3:28])[CH3:29])[CH:6]=2)[CH2:35][CH2:34]1)(=[O:32])[CH3:31]

参加物

5

反応物 3

HCID 4875Potassium IodideHCID 837951-AcetylpiperazineHCID 68541592HCID 68541592、化合物

生成物 1

HCID 9893171Azd-0424収率 90.2%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
100 °C

実験手順

A mixture of 7-(2-chloroethoxy)-4-(5-chloro-2,3-methylenedioxypyrid-4-ylamino)-5-isopropoxyquinazoline (24 g), 1-acetylpiperazine (21 g), potassium iodide (18 g) and DMA (500 ml) was stirred and heated to 100° C. for 4 hours. The solvent was evaporated and the residue was partitioned between methylene chloride (1 liter) and water (500 ml). The aqueous layer was extracted with methylene chloride. The organic solutions were combined, washed with brine, dried over magnesium sulphate and evaporated. The residue was purified by column chromatography on silica using increasingly polar mixtures of methylene chloride and methanol (from a 20:1 mixture to a 10:1 mixture) as eluent. After evaporation of the solvent, the material so obtained was triturated under diethyl ether. There was thus obtained the title compound as a white solid (26.2 g); m.p. 208-210° C.

後処理

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between methylene chloride (1 liter) and water (500 ml)
  3. extractionThe aqueous layer was extracted with methylene chloride
  4. washwashed with brine
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica using
  8. temperatureincreasingly polar mixtures of methylene chloride and methanol (from a 20:1 mixture to a 10:1 mixture) as eluent
  9. customAfter evaporation of the solvent
  10. customthe material so obtained
  11. customwas triturated under diethyl ether

出典と根拠

ORDレコード
ord-2af2a81bc1bd45f7b5a28f614ce1caf7
出典データセット
uspto-grants-2008_12
特許番号
US07462623B2

反応ノート

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