Trifluoroacetic acid → N-(5-chloro-1,3-benzodioxol-4-yl)-7-methoxy-5-(piperidin-4-yloxy)quinazolin-4-amine

HRID 1373316ノート

反応式

HRID 1373316 の反応式
Cl.Cl.C(OC([N:10]1[CH2:15][CH2:14][CH:13]([O:16][C:17]2[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[C:23]3[C:18]=2[C:19]([NH:29][C:30]2[C:35]([Cl:36])=[CH:34][CH:33]=[C:32]4[O:37][CH2:38][O:39][C:31]=24)=[N:20][CH:21]=[N:22]3)[CH2:12][CH2:11]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:36][C:35]1[C:30]([NH:29][C:19]2[C:18]3[C:23](=[CH:24][C:25]([O:27][CH3:28])=[CH:26][C:17]=3[O:16][CH:13]3[CH2:12][CH2:11][NH:10][CH2:15][CH2:14]3)[N:22]=[CH:21][N:20]=2)=[C:31]2[O:39][CH2:38][O:37][C:32]2=[CH:33][CH:34]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 221408065-(1-Tert-butoxycarbonylpiperidin-4-yloxy)-4-(6-chloro-2,3-methylenedioxyanilino)-7-methoxyquinazoline dihydrochloride

生成物 1

HCID 10274208N-(5-chloro-1,3-benzodioxol-4-yl)-7-methoxy-5-(piperidin-4-yloxy)quinazolin-4-amine収率 84.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 5-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-(6-chloro-2,3-methylenedioxyanilino)-7-methoxyquinazoline dihydrochloride (2.39 g), trifluoroacetic acid (10 ml) and methylene chloride (35 ml) was stirred at ambient temperature for 1.5 hours. The mixture was evaporated and the residue was partitioned between ethyl acetate and a 1N aqueous sodium hydroxide solution. The organic layer was washed with water and brine, dried over magnesium sulphate and evaporated. The residue was purified by column chromatography on silica using a 19:1 mixture of methylene chloride and methanol as eluent. There was thus obtained the title compound (1.44 g); NMR Spectrum: (CDCl3) 1.8–2.0 (m, 2H), 2.15–2.3 (m, 2H), 2.75–2.9 (m, 2H), 3.1–3.2 (m, 2H), 3.9 (s, 3H), 4.65 (m, 1H), 6.0 (s, 2H), 6.46 (d, 1H), 6.72 (d, 1H), 6.8 (d, 1H), 6.91 (d, 1H), 8.5 (s, 1H), 9.21 (s, 1H); Mass Spectrum: M+H+ 429 and 431.

後処理

  1. customThe mixture was evaporated
  2. customthe residue was partitioned between ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica using
  7. additiona 19:1 mixture of methylene chloride and methanol as eluent

出典と根拠

ORDレコード
ord-886aa496e63f437785806f79791f27b2
出典データセット
uspto-grants-2007_01
特許番号
US07160891B2

反応ノート

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