Acetic Anhydride → HCID 135554938, compound

HRID 1379025Notes

Reaction equation

HRID 1379025 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.[C:23](OC(=O)C)(=[O:25])[CH3:24]>C(O)(=O)C>[C:23]([N:13]1[CH2:14][CH2:15][N:10]2[N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)=[C:11]2[NH:12]1)(=[O:25])[CH3:24]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 135554955HCID 135554955, compound

Product 1

HCID 135554938HCID 135554938, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 7-(4-fluorophenyl)-8-(pyridin-4-yl)-1,2,3,4-tetrahydropyrazolo[5,1-c][1,2,4]triazine (207 mg) in acetic acid (2 ml) was added acetic anhydride (75 mg) with ice cooling. The solution was stirred at ambient temperature for 1 hour and concentrated in vacuo. The residue was dissolved in water (3 ml) and the solution was neutralized with an aqueous saturated sodium bicarbonate solution. The separated oil was extracted with dichloromethane and the extract was dried and concentrated in vacuo. The residue was crystallized from ethyl acetate to give 2-acetyl-7-(4-fluorophenyl)-8-(pyridin-4-yl)-1,2,3,4-tetrahydropyrazolo[5,1-c][1,2,4]triazine (195 mg).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in water (3 ml)
  3. extractionThe separated oil was extracted with dichloromethane
  4. customthe extract was dried
  5. concentrationconcentrated in vacuo
  6. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-5fcf88c3765a43c397fa644252934aa0
Source dataset
uspto-grants-1997_09
Patent number
US05670503

Reaction notes

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