Sodium hydride → 6-Methoxy-7-(2-methoxyethoxy)-4-(5-(2-morpholinoacetyl)oxindol-3-yl)quinazoline hydrochloride

HRID 1386313ノート

反応式

HRID 1386313 の反応式
[H-].[Na+].[O:3]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][C:16](=[O:21])[CH2:15]3)=[O:11])[CH2:5][CH2:4]1.[Cl:22][C:23]1[C:32]2[C:27](=[CH:28][C:29]([O:35][CH2:36][CH2:37][O:38][CH3:39])=[C:30]([O:33][CH3:34])[CH:31]=2)[N:26]=[CH:25][N:24]=1>CN(C=O)C>[ClH:22].[CH3:34][O:33][C:30]1[CH:31]=[C:32]2[C:27](=[CH:28][C:29]=1[O:35][CH2:36][CH2:37][O:38][CH3:39])[N:26]=[CH:25][N:24]=[C:23]2[CH:15]1[C:14]2[C:18](=[CH:19][CH:20]=[C:12]([C:10](=[O:11])[CH2:9][N:6]3[CH2:7][CH2:8][O:3][CH2:4][CH2:5]3)[CH:13]=2)[NH:17][C:16]1=[O:21]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 107306534-Chloro-6-methoxy-7-(2-methoxyethoxy)quinazolineHCID 21717309HCID 21717309、化合物

生成物 1

HCID 217172846-Methoxy-7-(2-methoxyethoxy)-4-(5-(2-morpholinoacetyl)oxindol-3-yl)quinazoline hydrochloride収率 42.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Sodium hydride (58 mg, 2.4 mmol) was added to solution of 5-(2-morpholinoacetyl)oxindole (312 mg, 1.2 mmol) and 4-chloro-6-methoxy-7-(2-methoxyethoxy)quinazoline (160 mg, 0.6 mmol), (prepared as described for the starting material in Example 2), in DMF (15 ml). The mixture was stirred for 1.5 hours at ambient temperature and the volatiles were removed by evaporation. The residue was purified by column chromatography eluting with methylene chloride/methanol (96/4 followed by 94/6). The purified solid product was triturated with ether, collected by filtration, washed with ether and dried under vacuum. The solid was dissolved in methylene chloride (10 ml) and methanol (10 ml) and 1M methanolic hydrogen chloride (2 ml) was added. The volatiles were removed by evaporation and the solid residue was suspended in ether, collected by filtration, washed with ether and dried under vacuum to give 6-methoxy-7-(2-methoxyethoxy)-4-(5-(2-morpholinoacetyl)oxindol-3-yl)quinazoline hydrochloride (136 mg, 39%).

後処理

  1. custom(prepared
  2. customthe volatiles were removed by evaporation
  3. customThe residue was purified by column chromatography
  4. washeluting with methylene chloride/methanol (96/4 followed by 94/6)
  5. customThe purified solid product was triturated with ether
  6. filtrationcollected by filtration
  7. washwashed with ether
  8. customdried under vacuum
  9. dissolutionThe solid was dissolved in methylene chloride (10 ml)
  10. additionmethanol (10 ml) and 1M methanolic hydrogen chloride (2 ml) was added
  11. customThe volatiles were removed by evaporation
  12. filtrationcollected by filtration
  13. washwashed with ether
  14. customdried under vacuum

出典と根拠

ORDレコード
ord-1235ee365948454aa6b0b0f91fd14dea
出典データセット
uspto-grants-2001_07
特許番号
US06265411B1

反応ノート

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