Pyridine → HCID 70108430, compound

HRID 1379027Notes

Reaction equation

HRID 1379027 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)=[C:11]3[NH:12][NH:13][CH2:14][CH2:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:29]([O:32][CH2:33][C:34](Cl)=[O:35])(=[O:31])[CH3:30]>CN1CCCC1=O.C(=O)(O)[O-].[Na+]>[C:29]([O:32][CH2:33][C:34]([N:12]1[C:11]2=[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[N:9][N:10]2[CH2:15][CH2:14][NH:13]1)=[O:35])(=[O:31])[CH3:30]

Participants

6

Reactant 3

HCID 1049PyridineHCID 26297Acetoxyacetyl chlorideHCID 135554955HCID 135554955, compound

Product 1

HCID 70108430HCID 70108430, compoundYield 56.7%

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a mixture of 7-(4-fluorophenyl)-8-(pyridin-4-yl)-1,2,3,4-tetrahydropyrazolo[5,1-c][1,2,4]triazine (100 mg, 0.339 mmol) and pyridine (54 mg, 0.678 mmol) in N-methyl-2-pyrrolidone (1.5 ml) was added acetoxyacetyl chloride (60 mg, 0.441 mmol) in N-methyl-2-pyrrolidone (0.5 ml) under nitrogen atmosphere with ice cooling. After stirring for 30 minutes, the reaction mixture was diluted with an aqueous saturated sodium bicarbonate solution, then 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; 100/1~20/1) and the obtained amorphous product was crystallized from diisopropyl ether to give 2-acetoxyacetyl-7-(4-fluorophenyl)-8-(pyridin-4-yl)-1,2,3,4-tetrahydropyrazolo-[5,1-c][1,2,4]triazine (76 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; 100/1~20/1)
  6. customthe obtained amorphous product was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-123cd74d5905427085e8291d0133e2ae
Source dataset
uspto-grants-1997_09
Patent number
US05670503

Reaction notes

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