Water → 3-[2-{(1R*,2R*)-2-hydroxy-2-methylcyclohexyl}-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]-pyridine

HRID 276941

反応式

HRID 276941 の反応式
[O:1]=[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)=[N:4][NH:3]1.[CH3:23][C:24]12[O:30][CH:25]1[CH2:26][CH2:27][CH2:28][CH2:29]2.[OH-].[Na+].O>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.C1(C)C=CC=CC=1>[OH:30][C@:24]1([CH3:23])[CH2:29][CH2:28][CH2:27][CH2:26][C@H:25]1[N:3]1[C:2](=[O:1])[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)=[N:4]1

参加物

7

反応物 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 2242431-Methyl-1,2-epoxycyclohexaneHCID 105894183(2H)-Pyridazinone, 6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-

生成物 1

HCID 701575183-[2-{(1R*,2R*)-2-hydroxy-2-methylcyclohexyl}-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]-pyridine収率 6%

試薬・触媒・溶媒 2

HCID 5963Benzyltrimethylammonium chloride触媒HCID 1140Toluene溶媒

実験手順

A mixture of 3-(3-oxo-2,3-dihydropyridazin-6-yl)-2-phenylpyrazolo[1,5-a]pyridine (2.25 g), 1-methyl-1,2-epoxycyclohexane (1.31 g), benzyltrimethylammonium chloride (178 mg), 1N aqueous sodium hydroxide (7.8 ml), water (17 ml), and toluene was heated to reflux for 8 hours and 20 minutes. After the reaction mixture was cooled to room temperature, the precipitates were collected by filtration, washed with water, and dried. The crude material was purified by column chromatography on silica gel (CH2Cl2:EtOAc=10:2) to give colorless crystals of 3-[2-{(1R*,2R*)-2-hydroxy-2-methylcyclohexyl}-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]-pyridine (189 mg).

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 8 hours and 20 minutes
  3. filtrationthe precipitates were collected by filtration
  4. washwashed with water
  5. customdried
  6. customThe crude material was purified by column chromatography on silica gel (CH2Cl2:EtOAc=10:2)

出典と根拠

ORDレコード
ord-b20287faa830487eb32ce42fa4bd440f
出典データセット
uspto-grants-2002_03
特許番号
US06355640B1

関連ノート

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