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Sodium Hydroxide → HCID 136262646、化合物

HRID 591672
ノート
印刷プレビュー

反応式

HRID 591672 の反応式
[CH2:1]([N:8]([CH:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]3[NH:33][C:32](=[O:34])[C:31]4[C:26](=[CH:27][C:28]([O:37][CH3:38])=[CH:29][C:30]=4[O:35][CH3:36])[N:25]=3)=[CH:20][N:19]=2)[CH2:14][CH2:13]1)C(=O)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>Cl>[CH2:1]([NH:8][CH:12]1[CH2:13][CH2:14][N:15]([C:18]2[N:19]=[CH:20][C:21]([C:24]3[NH:33][C:32](=[O:34])[C:31]4[C:26](=[CH:27][C:28]([O:37][CH3:38])=[CH:29][C:30]=4[O:35][CH3:36])[N:25]=3)=[CH:22][CH:23]=2)[CH2:16][CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 136262645HCID 136262645、化合物

生成物 1

HCID 136262646HCID 136262646、化合物収率 60%

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

実験手順

A solution of N-benzyl-N-(1-(5-(5,7-dimethoxy-4-oxo-3,4-dihydroquinazolin-2-yl)pyridin-2-yl)piperidin-4-yl)acetamide (0.200 g, 0.39 mmol) in 2 N HCl (15 mL) was refluxed for 3 days. The resulting mixture was basified with 2 N NaOH and extracted with CH2Cl2. The organics were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 10% to 100% of 92:7:1 CHCl3/MeOH/concentrated NH4OH in CH2Cl2, afforded the title compound (0.110 g, 60%) as a white solid. 1H NMR (300 MHz, DMSO-d6): δ 11.11 (br s, 1H), 8.89 (d, J=2.3 Hz, 1H), 8.22-8.26 (m, 1H), 7.28-7.37 (m, 4H), 7.18-7.23 (m, 1H), 6.91 (d, J=7.2 Hz, 1H), 6.67 (d, J=2.2 Hz, 1H), 6.46 (d, J=2.2 Hz, 1H), 4.27-4.31 (m, 2H), 3.88 (s, 3H), 3.83 (s, 3H), 3.76 (s, 2H), 3.00-3.11 (m, 2H), 2.62-2.69 (m, 1H), 1.88-1.91 (m, 2H), 1.25-1.31 (m, 2H). ESI MS m/z 472 [M+H]+.

後処理

  1. extractionextracted with CH2Cl2
  2. washThe organics were washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica gel
  7. washeluting with 10% to 100% of 92:7:1 CHCl3/MeOH/concentrated NH4OH in CH2Cl2

出典と根拠

ORDレコード
ord-6654cebfc50b4ffa9f88a60bcd96f6f3
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09238640B2

反応ノート

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このページの内容参加物実験手順後処理出典と根拠反応ノート