Potassium Carbonate → HCID 178513391, compound

HRID 418154Notes

Reaction equation

HRID 418154 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[N:8]2[N:9]=[CH:10][C:11]([C:12]#[N:13])=[C:7]2[N:6]=[C:5]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[CH:4]=1.Cl.[NH2:27][OH:28].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[OH:28][NH:27][C:12]([C:11]1[CH:10]=[N:9][N:8]2[C:3]([C:2]([F:25])([F:24])[F:1])=[CH:4][C:5]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:16][CH:15]=3)=[N:6][C:7]=12)=[NH:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 114055925-(4-Trifluoromethyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carbonitrile

Product 1

HCID 178513391HCID 178513391, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 7-trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carbonitrile [CAS-No. 851262-50-5] (2.0 g, 5.61 mmol), hydroxylamine hydrochloride (0.78 g, 11.2 mmol) and potassium carbonate (2.33 g, 16.8 mmol) in ethanol (100 ml) was heated under reflux conditions for 3 h. After the reaction mixture reached room temperature the precipitate was collected by filtration and washed with ethanol and ethyl acetate. The combined filtrates were evaporated and the crude product purified by flash chromatography on silica gel (ethyl acetate/heptane) to yield the title compound (1.51 g, 69%) as an orange solid. MS (ISP) 389.9 [(M+H)+]; mp 252° C.

Workup

  1. temperaturewas heated under reflux conditions for 3 h
  2. customreached room temperature
  3. filtrationwas collected by filtration
  4. washwashed with ethanol and ethyl acetate
  5. customThe combined filtrates were evaporated
  6. customthe crude product purified by flash chromatography on silica gel (ethyl acetate/heptane)

Sources & evidence

ORD record
ord-9d49e94b8ada4b98886d3d0b7f523268
Source dataset
uspto-grants-2012_01
Patent number
US08093263B2

Reaction notes

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