Hydrochloric Acid → HCID 15346148, compound

HRID 1871873Notes

Reaction equation

HRID 1871873 reaction equation
[CH3:1][OH:2].[H-].[Na+].[NH2:5][C:6]1[N:10]([C:11]2[C:16]([Cl:17])=[CH:15][C:14]([C:18]([F:21])([F:20])[F:19])=[C:13](F)[N:12]=2)[N:9]=[CH:8][C:7]=1[C:23]#[N:24].Cl>C(OC)(C)(C)C>[NH2:5][C:6]1[N:10]([C:11]2[C:16]([Cl:17])=[CH:15][C:14]([C:18]([F:21])([F:20])[F:19])=[C:13]([O:2][CH3:1])[N:12]=2)[N:9]=[CH:8][C:7]=1[C:23]#[N:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 24758Sodium hydrideHCID 18689522HCID 18689522, compound

Product 1

HCID 15346148HCID 15346148, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent2×

Procedure

5 ml of methanol were added to a suspension of 0.23 g (0.0092 mol) of 95% strength sodium hydride in 75 ml of methyl tert-butyl ether at 20° C. in the course of 10 minutes and the mixture was stirred for 25 minutes to give a clear solution. 3 g (0.0098 mol) of 5-amino-4-cyano-1-(3-chloro-6-fluoro-5-trifluoromethyl-2-pyridyl)pyrazole (Active Compound Example No. 2a.001) in 50 ml of methyl tert-butyl ether were then added with stirring and the mixture was stirred at 25° C. for 2 hours. About 50 g of ice and 100 ml of 1N hydrochloric acid were added and the phases were separated. The organic phase was washed with saturated sodium chloride solution, dried and filtered through silica gel. After concentrating, stirring with ether/pentane, filtering off with suction and drying, 2.4 g (77% of theory) of the title compound of m.p. 135-139° C. were obtained (Active Compound Example No. 2c.001).

Workup

  1. customto give a clear solution
  2. stirringwith stirring
  3. stirringthe mixture was stirred at 25° C. for 2 hours
  4. customthe phases were separated
  5. washThe organic phase was washed with saturated sodium chloride solution
  6. customdried
  7. filtrationfiltered through silica gel
  8. concentrationAfter concentrating
  9. stirringstirring with ether/pentane
  10. filtrationfiltering off with suction
  11. customdrying

Sources & evidence

ORD record
ord-9134795cbabb4602833d794a4d409983
Source dataset
uspto-grants-2000_08
Patent number
US06107253

Reaction notes

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