Sodium hydride → 7(N-tert-butoxycarbonylpiperidin-4-ylmethoxy)-4-(5-chloro-2,3-methylenedioxypyrid-4-ylamino)-6-methoxyquinazoline

HRID 2374439

反応式

HRID 2374439 の反応式
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[C:4]2[O:9][CH2:10][O:11][C:3]=12.[H-].[Na+].[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH:24]([CH2:27][O:28][C:29]2[CH:38]=[C:37]3[C:32]([C:33](Cl)=[N:34][CH:35]=[N:36]3)=[CH:31][C:30]=2[O:40][CH3:41])[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15]>CN(C=O)C>[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH:24]([CH2:27][O:28][C:29]2[CH:38]=[C:37]3[C:32]([C:33]([NH:1][C:2]4[C:7]([Cl:8])=[CH:6][N:5]=[C:4]5[O:9][CH2:10][O:11][C:3]=45)=[N:34][CH:35]=[N:36]3)=[CH:31][C:30]=2[O:40][CH3:41])[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 219360467-(N-tert-butoxycarbonylpiperidin-4-ylmethoxy)-4-chloro-6-methoxyquinazolineHCID 685486516-chloro-2H-[1,3]dioxolo[4,5-b]pyridin-7-amine

生成物 1

HCID 685487457(N-tert-butoxycarbonylpiperidin-4-ylmethoxy)-4-(5-chloro-2,3-methylenedioxypyrid-4-ylamino)-6-methoxyquinazoline

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

実験手順

Using a similar procedure to that described in Example 1, a solution of 4-amino-5-chloro-2,3-methylenedioxypyridine (0.193 g) in DMF (2 ml) was added to a stirred suspension of sodium hydride (60% dispersion in mineral oil, 0.048 g) in DMF (2 ml) and the mixture was stirred at ambient temperature for 15 minutes. A solution of 7-(N-tert-butoxycarbonylpiperidin-4-ylmethoxy)-4-chloro-6-methoxyquinazoline [International Patent Application WO 02/16352 (Note [24] within Example 2 thereof; 0.38 g] in DMF (4 ml) was added and the resultant mixture was stirred at ambient temperature for 1 hour. The reaction mixture was partitioned between ethyl acetate and brine. The organic phase was dried over magnesium sulphate and evaporated. The residue was purified by column chromatography on silica using a 49:1 mixture of methylene chloride and methanol. There was thus obtained the title compound as a solid (0.24 g); NMR Spectrum: DMSOd6) 1.29 (m, 2H), 1.45 (s, 9H), 1.8 (m, 2H), 2.04 (m, 1H), 2.83 (m, 2H), 4.0 (m, 7H), 8.12 (br s, 2H), 7.17 (br s, 1H), 7.72 (m, 2H), 8.37 (br s, 1H), 9.37 (br s, 1H); Mass Spectrum: M+H+ 544 and 546.

後処理

  1. customThe reaction mixture was partitioned between ethyl acetate and brine
  2. dry with materialThe organic phase was dried over magnesium sulphate
  3. customevaporated
  4. customThe residue was purified by column chromatography on silica using
  5. additiona 49:1 mixture of methylene chloride and methanol

出典と根拠

ORDレコード
ord-d4b92020e037417db9b6e668c58cc513
出典データセット
uspto-grants-2008_12
特許番号
US07462623B2

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