Carbon Dioxide → HCID 9905671, compound

HRID 2073198Notes

Reaction equation

HRID 2073198 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(=O)=O.[H-].[Na+].[N:28]#[C:29]Br>O1CCCC1.O.CC(C)=O>[NH2:28][C:29]1[N:12]2[C:13]3[N:14]([C:9]([C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:21])([F:1])[F:22])[CH:4]=4)=[CH:10][CH2:11]2)[N:15]=[CH:16][C:17]=3[C:18](=[O:19])[N:20]=1

Participants

8

Reactant 4

HCID 280Carbon DioxideHCID 10476Cyanogen BromideHCID 24758Sodium hydrideHCID 27370934,5-Dihydro-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide

Product 1

HCID 9905671HCID 9905671, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 556 mg of 4,5-dihydro-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide (prepared as described in Example 4) in 25 ml of dry tetrahydrofuran, under nitrogen, cooled to -78° C. (dry-ice, acetone), was added 159 mg of sodium hydride (60% dispersion in mineral oil) in one portion. After stirring the mixture at -78° C. for 30 minutes, 191 mg of cyanogen bromide was added in one portion. The reaction mixture temperature was maintained at -78° C. for 4 hours, then was allowed to warm to room temperature over 16 hours. The mixture was diluted with water and the solid which separated was collected and washed with water and ether to give the product as a brown solid, m.p. 287°-289° C. (dec).

Workup

  1. temperatureThe reaction mixture temperature was maintained at -78° C. for 4 hours
  2. temperatureto warm to room temperature over 16 hours
  3. customthe solid which separated
  4. customwas collected
  5. washwashed with water and ether

Sources & evidence

ORD record
ord-c2d21d007dd84f0eaeab07d7fb89b067
Source dataset
uspto-grants-1990_04
Patent number
US04916137

Reaction notes

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