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

HRID 276941

Reaction equation

HRID 276941 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 1140TolueneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-b20287faa830487eb32ce42fa4bd440f
Source dataset
uspto-grants-2002_03
Patent number
US06355640B1

Linked notes

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