Sodium Hydroxide → HCID 70110969, compound

HRID 1379032Notes

Reaction equation

HRID 1379032 reaction equation
C([O:4][CH2:5][C:6]([N:8]1[C:13]2=[C:14]([C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)[C:15]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)=[N:16][N:12]2[CH2:11][CH2:10][NH:9]1)=[O:7])(=O)C.[OH-].[Na+]>C(O)C>[F:23][C:20]1[CH:19]=[CH:18][C:17]([C:15]2[C:14]([C:24]3[CH:25]=[CH:26][N:27]=[CH:28][CH:29]=3)=[C:13]3[N:8]([C:6](=[O:7])[CH2:5][OH:4])[NH:9][CH2:10][CH2:11][N:12]3[N:16]=2)=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70108430HCID 70108430, compound

Product 1

HCID 70110969HCID 70110969, compoundYield 29.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-acetoxyacetyl-7-(4-fluorophenyl)-8-(pyridin-4-yl)-1,2,3,4-tetrahydropyrazolo[5,1-c][1,2,4]triazine (75 mg, 0.190 mmol) and an aqueous sodium hydroxide solution (1N, 0.38 ml, 0.380 mmol) in ethanol (1.5 ml) was stirred for 30 minutes at ambient temperature. After dilution of an aqueous saturated ammonium chloride solution, the mixture was extracted with ethyl acetate. The extracts were dried over sodium sulfate, and concentrated in vacuo. The residue was purified by chromatography on silica gel (eluent:dichloromethane/methanol; 50/1~10/1), and the obtained amorphous product was crystallized from diisopropyl ether to give 7-(4-fluorophenyl)- 2-hydroxyacetyl-8-(pyridin-4-yl)-1,2,3,4-tetrahydropyrazolo[5,1-c][1,2,4]triazine (20 mg).

Workup

  1. extractionAfter dilution of an aqueous saturated ammonium chloride solution, the mixture was extracted with ethyl acetate
  2. dry with materialThe extracts were dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography on silica gel (eluent:dichloromethane/methanol; 50/1~10/1)
  5. customthe obtained amorphous product was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-9e87c52475794bcebda2c9dd4a20ed8c
Source dataset
uspto-grants-1997_09
Patent number
US05670503

Reaction notes

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