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Potassium Carbonate → 4-(7-Azaindol-5-yloxy)-6-methoxy-7-(3-(4-methylsulphonylpiperazin-1-yl)propoxy)quinazoline

HRID 2068038
ノート
印刷プレビュー

反応式

HRID 2068038 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][N:21]([S:24]([CH3:27])(=[O:26])=[O:25])[CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[OH:28][C:29]1[CH:30]=[C:31]2[C:35](=[N:36][CH:37]=1)[NH:34][CH:33]=[CH:32]2.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[NH:34]1[C:35]2[C:31](=[CH:30][C:29]([O:28][C:2]3[C:11]4[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]5[CH2:23][CH2:22][N:21]([S:24]([CH3:27])(=[O:26])=[O:25])[CH2:20][CH2:19]5)=[C:9]([O:12][CH3:13])[CH:10]=4)[N:5]=[CH:4][N:3]=3)=[CH:37][N:36]=2)[CH:32]=[CH:33]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 220307221H-Pyrrolo[2,3-b]pyridin-5-olHCID 866180984-Chloro-6-methoxy-7-(3-(4-methylsulphonylpiperazin-1-yl)propoxy)quinazoline

生成物 1

HCID 101745984-(7-Azaindol-5-yloxy)-6-methoxy-7-(3-(4-methylsulphonylpiperazin-1-yl)propoxy)quinazoline収率 45%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

反応条件

温度
85 °C

実験手順

A suspension of 4-chloro-6-methoxy-7-(3-(4-methylsulphonylpiperazin-1-yl)propoxy)quinazoline (0.25 g, 0.66 mmol), 5-hydroxy-7-azaindole (0.089 g, 0.663 mmol), (prepared as described for the starting material in Example 2), and potassium carbonate (0.091 g, 0.66 mmol) in DMF (3 ml) was stirred at 85° C. for 3 hours. The mixture was filtered and the filtrate was purified by preparative LCtMS eluting with acetonitrile/water (containing 1% acetic acid). The fractions containing the expected product were combined and evaporated. The residue was dissolved in methylene chloride and washed with 0.5N aqueous ammonia followed by brine, dried (MgSO4) and evaporated. The residue was triturated under diethyl ether, filtered and dried under vacuum to give 4-(7-azaindol-5-yloxy)-6-methoxy-7-(3-(4-methylsulphonylpiperazin-1-yl)propoxy)quinazoline (0.138 g, 45%).

後処理

  1. custom(prepared
  2. filtrationThe mixture was filtered
  3. customthe filtrate was purified by preparative LCtMS
  4. washeluting with acetonitrile/water (containing 1% acetic acid)
  5. additionThe fractions containing the expected product
  6. customevaporated
  7. dissolutionThe residue was dissolved in methylene chloride
  8. washwashed with 0.5N aqueous ammonia
  9. dry with materialdried (MgSO4)
  10. customevaporated
  11. customThe residue was triturated under diethyl ether
  12. filtrationfiltered
  13. customdried under vacuum

出典と根拠

ORDレコード
ord-0f84e3198ab94000a7e0e2a4df767612
出典データセット
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08293902B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート