Water → Topiroxostat

HRID 1486665Notes

Reaction equation

HRID 1486665 reaction equation
O.P(=O)(O)(O)O.[C:7]([C:9]1[CH:14]=[C:13]([C:15]([NH:17][NH:18][C:19]([C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)=O)=[NH:16])[CH:12]=[CH:11][N:10]=1)#[N:8]>CC(O)CC>[N:24]1[CH:25]=[CH:26][C:21]([C:19]2[NH:18][N:17]=[C:15]([C:13]3[CH:12]=[CH:11][N:10]=[C:9]([C:7]#[N:8])[CH:14]=3)[N:16]=2)=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1004Phosphoric AcidHCID 178510073HCID 178510073, compound

Product 1

HCID 5288320Topiroxostat

Reagents, catalysts & solvents 1

HCID 6568(+-)-2-ButanolSolvent

Conditions

Temperature
80 °C

Procedure

Water (82 mL), 2-butanol (8.2 mL), and phosphoric acid (4.00 g) were added to 4-pyridinecarboxylic acid N′-(2-cyanopyridine-4-carbonimidoyl)hydrazide (4) (9.25 g), and the mixture was stirred at 80° C. for 8 hours. The reaction mixture was cooled to room temperature, and precipitated crystals were recovered through filtration. The crystals were washed with a water-2-butanol (10:1) mixture (92.5 mL). The thus-washed crystal were dried at 80° C. for 13 hours under reduced pressure, to thereby yield 7.89 g of 4-[5-(pyridin-4-yl)-1H-1,2,4-triazol-3-yl]pyridine-2-carbonitrile (1).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customprecipitated crystals
  3. filtrationwere recovered through filtration
  4. washThe crystals were washed with a water-2-butanol (10:1) mixture (92.5 mL)
  5. customThe thus-washed crystal were dried at 80° C. for 13 hours under reduced pressure

Sources & evidence

ORD record
ord-087ac9db0ca34ce3843860b045736736
Source dataset
uspto-grants-2016_08
Patent number
US09428488B2

Reaction notes

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