Potassium Carbonate → HCID 135554946, compound

HRID 1379033Notes

Reaction equation

HRID 1379033 reaction equation
C([O:4][C:5]1[CH:34]=[CH:33][C:8]([C:9]([N:11]2[CH2:16][CH2:15][N:14]3[N:17]=[C:18]([C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)[C:19]([C:20]4[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=4)=[C:13]3[NH:12]2)=[O:10])=[CH:7][CH:6]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CO>[F:32][C:29]1[CH:30]=[CH:31][C:26]([C:18]2[C:19]([C:20]3[CH:21]=[CH:22][N:23]=[CH:24][CH:25]=3)=[C:13]3[NH:12][N:11]([C:9](=[O:10])[C:8]4[CH:7]=[CH:6][C:5]([OH:4])=[CH:34][CH:33]=4)[CH2:16][CH2:15][N:14]3[N:17]=2)=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 136161708HCID 136161708, compound

Product 1

HCID 135554946HCID 135554946, compoundYield 62.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-(4-acetoxybenzoyl)-7-(4-fluorophenyl)-8-(pyridin-4-yl)-1,2,3,4-tetrahydropyrazolo[5,1-c][1,2,4]triazine (65 mg, 0.142 mmol) and potassium carbonate (20 mg, 0.142 mmol) in methanol (1.3 ml) was stirred for 30 minutes at ambient temperature. The mixture was adjusted to pH 6 with an aqueous saturated ammonium chloride solution, and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by chromatography on silica gel (eluent:dichloromethane/methanol; 30/1~20/1), and the obtained amorphous product was crystallized from diisopropyl ether to give 7-(4-fluorophenyl)-2-(4-hydroxybenzoyl)-8-(pyridin-4-yl)-1,2,3,4-tetrahydropyrazolo[5,1-c][1,2,4]triazine (37 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography on silica gel (eluent:dichloromethane/methanol; 30/1~20/1)
  6. customthe obtained amorphous product was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-b46291340c274ed88c6938a1ea2f0784
Source dataset
uspto-grants-1997_09
Patent number
US05670503

Reaction notes

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