Hydrochloric Acid → HCID 15346148, compound

HRID 1290147Notes

Reaction equation

HRID 1290147 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 in the course of 10 minutes at 20° C. to a suspension of 0.23 g (0.0092 mol) of 95% sodium hydride in 75 ml of methyl tert-butyl ether and the mixture was stirred for 25 minutes until a clear solution was obtained. 3 g (0.0098 mol) 10 of 5-amino-4-cyano-1-(3-chloro-6-fluoro-5-trifluoromethylpyrid-2-yl) pyrazole (Example IV.1.) in 50 ml of methyl tert-butyl ether were subsequently added with stirring and the mixture was stirred for 2 hours at 25 C. Approximately 50 g of ice and 100 ml of hydrochloric acid were added and the phases were separated. The organic phase was washed using saturated sodium chloride solution, dried and filtered through silica gel. After concentration, stirring with ether/pentane, filtration with suction and drying, 2.4 g (77% of theory) of the title compound of m.p. 135°-139° C. were obtained (active ingredient example No. 5.003).

Workup

  1. customwas obtained
  2. stirringwith stirring
  3. stirringthe mixture was stirred for 2 hours at 25 C
  4. customthe phases were separated
  5. washThe organic phase was washed
  6. customdried
  7. filtrationfiltered through silica gel
  8. concentrationAfter concentration
  9. stirringstirring with ether/pentane, filtration with suction
  10. customdrying

Sources & evidence

ORD record
ord-c950c6e158de4f5a81df6cbd9aeca046
Source dataset
uspto-grants-1998_05
Patent number
US05750705

Reaction notes

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