3-(2-Fluorophenyl)-5-(4-oxopiperidin-1-yl)-[1,2,3]triazolo[1,5-a]quinazoline → 3-(2-Fluorophenyl)-5-(4-hydroxy-4-methylpiperidin-1-yl)-[1,2,3]triazolo[1,5-a]quinazoline

HRID 1581632ノート

反応式

HRID 1581632 の反応式
[CH3:1][Mg]Br.[F:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[N:12]=[N:13][N:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([N:24]3[CH2:29][CH2:28][C:27](=[O:30])[CH2:26][CH2:25]3)=[N:16][C:15]=12>O1CCCC1.O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[F:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[N:12]=[N:13][N:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([N:24]3[CH2:25][CH2:26][C:27]([OH:30])([CH3:1])[CH2:28][CH2:29]3)=[N:16][C:15]=12

参加物

6

反応物 2

HCID 99251083-(2-Fluorophenyl)-5-(4-oxopiperidin-1-yl)-[1,2,3]triazolo[1,5-a]quinazolineHCID 178418573HCID 178418573、化合物

生成物 1

HCID 101341923-(2-Fluorophenyl)-5-(4-hydroxy-4-methylpiperidin-1-yl)-[1,2,3]triazolo[1,5-a]quinazoline収率 47%

試薬・触媒・溶媒 3

HCID 311Citric Acid溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Methylmagnesium bromide (3M in diethyl ether, 0.24 ml, 0.72 mmol) was added to a stirred solution of 3-(2-fluorophenyl)-5-(4-oxopiperidin-1-yl)-[1,2,3]triazolo[1,5-α]quinazoline (Example 22) (0.107 g, 0.3 mmol) in dry tetrahydrofuran (2 ml) at room temperature under nitrogen. After stirring for 2 h, the mixture was diluted with water (20 ml) and 1M aqueous citric acid (5 ml). The mixture was extracted with dichloromethane (20 ml) and the organic extract was dried (Na2SO4), filtered and concentrated. Preparative thin layer chromatography on silica, eluting with 2% methanol:dichloromethane, gave 3-(2-fluorophenyl)-5-(4-hydroxy-4-methylpiperidin-1-yl)-[1,2,3]triazolo[1,5-α]quinazoline (0.053 g, 47%). δH (360 MHz; CDCl3) 1.38 (3H, s), 1.75-1.85 (2H, m), 1.90-2.00 (2H, m), 3.56-3.64 (2H, m), 3.83-3.89 (2H, m), 7.20-7.30 (2H, m), 7.30-7.40 (1H, m), 7.60 (1H, dd, J=7 and 7), 7.88 (1H, dd, J=7 and 7), 8.02 (1H, d, J=7), 8.15 (1H, dd, J=7 and 7), 8.68 (1H, d, J=7); m/z (ES+) 378 (M+H+).

後処理

  1. extractionThe mixture was extracted with dichloromethane (20 ml)
  2. extractionthe organic extract
  3. dry with materialwas dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washPreparative thin layer chromatography on silica, eluting with 2% methanol

出典と根拠

ORDレコード
ord-2eaaeba0e0f5418885ea0c1db43c7f89
出典データセット
uspto-grants-2004_05
特許番号
US06730681B2

反応ノート

読み込み中…