Hydrochloric Acid → HCID 12149008, compound

HRID 1007564Notes

Reaction equation

HRID 1007564 reaction equation
CN(C)C=[N:4][S:5]([C:8]1[CH:9]=[N:10][C:11]([N:14]2[C:18](Cl)=[C:17]([C:20]#[N:21])[C:16]([C:22]([F:25])([F:24])[F:23])=[N:15]2)=[CH:12][CH:13]=1)(=[O:7])=[O:6].[CH3:27][C:28]([CH3:32])([CH3:31])[CH2:29][OH:30].[F-].[Cs+].Cl>CS(C)=O.C(#N)C.O>[C:20]([C:17]1[C:16]([C:22]([F:24])([F:23])[F:25])=[N:15][N:14]([C:11]2[N:10]=[CH:9][C:8]([S:5]([NH2:4])(=[O:6])=[O:7])=[CH:13][CH:12]=2)[C:18]=1[O:30][CH2:29][C:28]([CH3:32])([CH3:31])[CH3:27])#[N:21]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6404Neopentyl alcoholHCID 25953Cesium fluorideHCID 69835511HCID 69835511, compound

Product 1

HCID 12149008HCID 12149008, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
20 °C

Procedure

6-[5-chloro-4-cyano-3-trifluoromethyl-pyrazol-1-yl]-pyridine-3-sulfonic acid dimethyl-aminomethyleneamide (81.3 mg, 0.2 mmol) and 2,2-dimethyl-1-propanol (35.3 mg, 0.4 mmol) were dissolved in dry DMSO (0.5 ml) and cesium fluoride (60.7 mg, 0.4 mmol) was added to the solution. The resulting mixture was stirred at 20° C. for a period of 24 hours. Analytical HPLC indicated the reaction completion. The reaction mixture was poured into water (2 ml) and the resulting mixture was extracted with ethyl acetate (2 ml). The ethyl acetate mixture was filtered into a vial and evaporated to dryness under nitrogen atmosphere to leave a residue. Acetonitrile (2 ml) was added, and the mixture shaken to dissolve the residue. 2N HCl (1.5 ml) was added into the acetonitrile mixture, and the reaction mixture warmed to 70° C. for a period of 18 hours. After cooling down, the acetonitrile was evaporated under reduced pressure, and ethyl acetate (5 ml) was added to the evaporated mixture with stirring. The ethyl acetate layer was then separated, washed with saturated sodium chloride (5 ml), dried over magnesium sulfate and concentrated. HPLC purification of the residue obtained above gives the title compound. (37.6 mg, 46%). MS: 404.5, r.t.: 2.7.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate (2 ml)
  2. filtrationThe ethyl acetate mixture was filtered into a vial and
  3. customevaporated to dryness under nitrogen atmosphere
  4. customto leave a residue
  5. stirringthe mixture shaken
  6. dissolutionto dissolve the residue
  7. temperaturethe reaction mixture warmed to 70° C. for a period of 18 hours
  8. temperatureAfter cooling down
  9. customthe acetonitrile was evaporated under reduced pressure, and ethyl acetate (5 ml)
  10. additionwas added to the evaporated mixture
  11. stirringwith stirring
  12. customThe ethyl acetate layer was then separated
  13. washwashed with saturated sodium chloride (5 ml)
  14. dry with materialdried over magnesium sulfate
  15. concentrationconcentrated
  16. customHPLC purification of the residue
  17. customobtained

Sources & evidence

ORD record
ord-0a47fdb6458b4bc1a02496a0fa975f25
Source dataset
uspto-grants-2004_09
Patent number
US06794512B2

Reaction notes

Loading…