Potassium Carbonate → 7-(3-(1,1-Dioxothiomorpholino)propoxy)-6-methoxy-4-(quinolin-7-yloxy)quinazoline

HRID 453990ノート

反応式

HRID 453990 の反応式
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][S:21](=[O:25])(=[O:24])[CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[OH:32][C:33]1[CH:42]=[C:41]2[C:36]([CH:37]=[CH:38][CH:39]=[N:40]2)=[CH:35][CH:34]=1.[OH-].[Na+]>CN(C=O)C>[O:24]=[S:21]1(=[O:25])[CH2:22][CH2:23][N:18]([CH2:17][CH2:16][CH2:15][O:14][C:8]2[CH:7]=[C:6]3[C:11]([C:2]([O:32][C:33]4[CH:42]=[C:41]5[C:36]([CH:37]=[CH:38][CH:39]=[N:40]5)=[CH:35][CH:34]=4)=[N:3][CH:4]=[N:5]3)=[CH:10][C:9]=2[O:12][CH3:13])[CH2:19][CH2:20]1

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 219360004-Chloro-7-(3-(1,1-dioxothiomorpholino)propoxy)-6-methoxyquinazolineHCID 1354268667-Hydroxyquinoline

生成物 1

HCID 98703767-(3-(1,1-Dioxothiomorpholino)propoxy)-6-methoxy-4-(quinolin-7-yloxy)quinazoline収率 73%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

A mixture of 4-chloro-7-(3-(1,1-dioxothiomorpholino)propoxy)-6-methoxyquinazoline (220 mg, 0.57 mmol), potassium carbonate (106 mg, 0.77 mmol) and 7-hydroxyquinoline (111 mg, 0.76 mmol) in DMF (7.5 ml) was stirred at 100° C. for 5 hours then allowed to cool to ambient temperature. The reaction mixture was treated with 1M aqueous sodium hydroxide solution (40 ml) and stirred at ambient temperature for a few minutes. The crude solid was collected by filtration washing with water. The resultant solid was dissolved in dichloromethane (2 ml) and was filtered through phase separating paper. The filtrate was evaporated under vacuum to give a solid residue which was triturated with ether, filtered and dried to give 7-(3-(1,1-dioxothiomorpholino)propoxy)-6-methoxy-4-(quinolin-7-yloxy)quinazoline (205 mg, 73%).

後処理

  1. temperatureto cool to ambient temperature
  2. stirringstirred at ambient temperature for a few minutes
  3. filtrationThe crude solid was collected by filtration
  4. washwashing with water
  5. dissolutionThe resultant solid was dissolved in dichloromethane (2 ml)
  6. filtrationwas filtered through phase
  7. customseparating paper
  8. customThe filtrate was evaporated under vacuum
  9. customto give a solid residue which
  10. customwas triturated with ether
  11. filtrationfiltered
  12. customdried

出典と根拠

ORDレコード
ord-7ddb8060bdc544a5b9d8d4bb1b57115a
出典データセット
uspto-grants-2013_07
特許番号
US08492560B2

反応ノート

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