Benzoyl isothiocyanate → 4-[(Benzoylamino)thioxomethyl]-4,5-dihydro-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 2073193Notes

Reaction equation

HRID 2073193 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([C:9]2[N:14]3[N:15]=[CH:16][C:17]([C:18]([NH2:20])=[O:19])=[C:13]3[NH:12][CH2:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[C:23]([N:31]=[C:32]=[S:33])(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CC(C)=O>[C:23]([NH:31][C:32](=[S:33])[N:12]1[CH2:11][CH:10]=[C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:21])([F:1])[F:22])[CH:4]=2)[N:14]2[N:15]=[CH:16][C:17]([C:18]([NH2:20])=[O:19])=[C:13]12)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanate2×HCID 27370934,5-Dihydro-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide

Product 1

HCID 157027764-[(Benzoylamino)thioxomethyl]-4,5-dihydro-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a stirred solution of 3.08 g of 4,5-dihydro-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide (Example 4) in 30 ml of dry acetone, under nitrogen was added 1.5 ml of benzoyl isothiocyanate in 5 ml of dry acetone. The mixture was heated at reflux for 3 hours, then an additional 4.5 ml of benzoyl isothiocyanate was added and the mixture was heated at reflux for 16 hours. The mixture was cooled to room temperature and the solid precipitate that had formed was collected by filtration and washed with ether to give 600 mg of 4-[(benzoylamino)thioxomethyl]-4,5-dihydro-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide, m.p. 210°-212° C. To a stirred mixture of 1.5 g of the preceding product (prepared as described above), 30 ml of N,N-dimethylformamide and 2.0 ml of 1N sodium hydroxide was added 4.0 ml of methyl iodide. This mixture was stirred at room temperature for 3 hours then an additional 1.0 ml of 1N sodium hydroxide and 2.0 ml of methyl iodide were added and stirring was continued. After one hour the addition of 1.0 ml of sodium hydroxide and 2.0 ml of methyl iodide was repeated and stirring was concluded within one hour of this addition. The mixture was mixed with water and the solid precipitate was collected by filtration, washed with water and dried in vacuo to give 1.4 g of 3-(aminocarbonyl)-N-benzoyl-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-4(5H)-carboximidothioic acid, methyl ester, m.p. 172°-175° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 hours
  3. temperaturethe mixture was heated
  4. temperatureat reflux for 16 hours
  5. customthe solid precipitate that had formed
  6. filtrationwas collected by filtration
  7. washwashed with ether

Sources & evidence

ORD record
ord-93fac654bc584e27a85b5d37c62ea194
Source dataset
uspto-grants-1990_04
Patent number
US04916137

Reaction notes

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