Potassium Carbonate → HCID 22030734、化合物

HRID 454190ノート

反応式

HRID 454190 の反応式
[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:18](=[O:21])([O-])[O-].[K+].[K+].ClC1[C:34]2[C:29](=[CH:30][C:31]([O:37][CH2:38][CH2:39][CH2:40][N:41]3[CH2:46][CH2:45][O:44][CH2:43][CH2:42]3)=[C:32]([O:35][CH3:36])[CH:33]=2)[N:28]=[CH:27][N:26]=1.[H-].[Na+]>CN(C)C=O.C(OCC)(=O)C.O>[CH3:36][O:35][C:32]1[CH:33]=[C:34]2[C:29](=[CH:30][C:31]=1[O:37][CH2:38][CH2:39][CH2:40][N:41]1[CH2:42][CH2:43][O:44][CH2:45][CH2:46]1)[N:28]=[CH:27][N:26]=[C:18]2[O:21][C:14]1[CH:13]=[C:12]2[C:17](=[CH:16][CH:15]=1)[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10][CH2:11]2

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 10633398tert-Butyl 3,4-dihydroquinoline-1(2H)-carboxylateHCID 118239414-Chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazoline

生成物 1

HCID 22030734HCID 22030734、化合物収率 71%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

6-Hydroxy-4-(1-tertbutoxycarbonyl-1,2,3,4-tetrahydroquinoline (82 mg, 0.32 mmol) was dissolved in anhydrous dimethylformamide under argon, with potassium carbonate (61 mg, 0.44 mmol) and 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (100 mg, 0.3 mmol), (prepared as described for the starting material in Example 1). No reaction occurred after 2 hours at 60° C. Sodium hydride (12 mg, 0.3 mmol) was added and the reaction mixture was heated at 120° C. for 90 minutes. The cooled mixture was poured into water and ethyl acetate. The organic phase was washed with water, brine, dried (MgSO4), filtered and the solvent evaporated. The residue was purified by flash chromatography using first dichloromethane/methanol (97/3) as solvent. Evaporation of the solvent gave 6-methoxy-7-(3-morpholinopropoxy)-4-((1-tertbutoxycarbonyl-1,2,3,4-tetrahydroquinolin-6-yl)oxy)quinazoline (115 mg, 71%) as a white solid.

後処理

  1. custom(prepared
  2. washThe organic phase was washed with water, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent evaporated
  6. customThe residue was purified by flash chromatography
  7. customEvaporation of the solvent

出典と根拠

ORDレコード
ord-dc8906df9d564b788c3d96baa50b55de
出典データセット
uspto-grants-2013_07
特許番号
US08492560B2

反応ノート

読み込み中…