Acetic Acid → HCID 21081678, compound

HRID 2117181Notes

Reaction equation

HRID 2117181 reaction equation
O[C:2]1[C:7]2=[C:8]([CH3:15])[C:9]([C:11]([NH:13][NH2:14])=[O:12])=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1.[CH3:16][C:17](O)=O.O=P(Cl)(Cl)[Cl:22]>>[Cl:22][C:2]1[C:7]2=[C:8]([CH3:15])[C:9]([C:11]3[O:12][C:16]([CH3:17])=[N:14][N:13]=3)=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 24813Phosphorus oxychlorideHCID 178429575HCID 178429575, compound

Product 1

HCID 21081678HCID 21081678, compound

Conditions

Temperature
80 °C

Procedure

To a suspension of 4-hydroxy-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carbohydrazide (100 mg, 0.48 mmol) in POCl3 (5 mL) was added AcOH (50 mg, 0.83 mmol). The reaction mixture was heated at 80° C. for 3 d, cooled to rt, and concentrated in vacuo. The resulting residue was dissolved in EtOAc and treated with sat. aq. NaHCO3 solution, brine, and dried over MgSO4. Filtration, followed by concentration, provide the title compound, which was used directly in next step. MS (ESI) m/z 250.1/252.1 (M+H)+.

Workup

  1. temperaturecooled to rt
  2. concentrationconcentrated in vacuo
  3. dissolutionThe resulting residue was dissolved in EtOAc
  4. additiontreated with sat. aq. NaHCO3 solution, brine
  5. dry with materialdried over MgSO4
  6. filtrationFiltration
  7. concentrationfollowed by concentration

Sources & evidence

ORD record
ord-463c7588efa34e609fa2fcf94c5f226a
Source dataset
uspto-grants-2008_10
Patent number
US07439246B2

Reaction notes

Loading…