Hydrochloric Acid → HCID 66850618, compound

HRID 1466581Notes

Reaction equation

HRID 1466581 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:33][CH3:34])=[C:6]([C:8]2[N:12](COCC[Si](C)(C)C)[N:11]=[CH:10][C:9]=2[NH:21][C:22]([C:24]2[CH:25]=[N:26][N:27]3[CH:32]=[CH:31][CH:30]=[N:29][C:28]=23)=[O:23])[CH:7]=1.Cl>C(O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:33][CH3:34])=[C:6]([C:8]2[NH:12][N:11]=[CH:10][C:9]=2[NH:21][C:22]([C:24]2[CH:25]=[N:26][N:27]3[CH:32]=[CH:31][CH:30]=[N:29][C:28]=23)=[O:23])[CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66850803HCID 66850803, compound

Product 1

HCID 66850618HCID 66850618, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of N-(5-(5-chloro-2-methoxyphenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (2.75 g, 5.51 mmol) in 105 mL ethanol was added HCl (8.0 mL of a 5 M solution in water, 40 mmol). The reaction mixture was then stirred at 70° C. for 2 hours. After cooling to room temperature, the product was filtered as a light yellow solid, rinsing with methanol and diethyl ether. The filtrate was reduced in volume, and more solid product filtered. The combined collected solids were dried under vacuum to yield 1.81 g (89%) of N-(5-(5-chloro-2-methoxyphenyl)-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide. LCMS (ESI) m+H=369.2; 1H NMR (400 MHz, DMSO-d6) δ: 9.66 (s, 1H), 9.33 (dd, J=7.0, 1.6, 1H), 8.78 (dd, J=4.2, 1.6, 1H), 8.65 (s, 1H), 8.20 (s, 1H), 7.50 (dd, J=8.8, 2.7, 1H), 7.44 (d, J=2.7, 1H), 7.29 (dd, J=7.8, 4.8, 2H), 3.86 (s, 3H).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe product was filtered as a light yellow solid
  3. washrinsing with methanol and diethyl ether
  4. filtrationfiltered
  5. customThe combined collected solids
  6. customwere dried under vacuum

Sources & evidence

ORD record
ord-de96a9ba86a0474cbc543edd399579aa
Source dataset
uspto-grants-2015_04
Patent number
US08999998B2

Reaction notes

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