4-Cyanophenylhydrazine Hydrochloride → 6-[1-(4-Cyanophenyl)-1H-pyrazol-5-yl]-N,N,5-trimethyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxamide

HRID 1958300Notes

Reaction equation

HRID 1958300 reaction equation
C(O[CH:4](OCC)[C:5]#[C:6][C:7]1[N:12]=[C:11]([C:13]([N:15]([CH3:17])[CH3:16])=[O:14])[C:10](=[O:18])[N:9]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=2)[C:8]=1[CH3:29])C.Cl.[C:34]([C:36]1[CH:41]=[CH:40][C:39]([NH:42][NH2:43])=[CH:38][CH:37]=1)#[N:35]>CN(C=O)C>[C:34]([C:36]1[CH:41]=[CH:40][C:39]([N:42]2[C:6]([C:7]3[N:12]=[C:11]([C:13]([N:15]([CH3:16])[CH3:17])=[O:14])[C:10](=[O:18])[N:9]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:26])[F:27])[CH:20]=4)[C:8]=3[CH3:29])=[CH:5][CH:4]=[N:43]2)=[CH:38][CH:37]=1)#[N:35]

Participants

4

Reactant 2

HCID 162129624-Cyanophenylhydrazine HydrochlorideHCID 667387186-(3,3-Diethoxyprop-1-ynyl)-N,N,5-trimethyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxamide

Product 1

HCID 248903136-[1-(4-Cyanophenyl)-1H-pyrazol-5-yl]-N,N,5-trimethyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxamideYield 29.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

6-(3,3-Diethoxyprop-1-ynyl)-N,N,5-trimethyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxamide (0.028 g, 0.062 mmol) was dissolved in DMF (1 ml) in a microwave vial. 4-Cyanophenylhydrazine hydrochloride (0.013 g, 0.074 mmol) was added. The vial was sealed and heated with stirring to 120° C. for 5 minutes. The crude mixture was purified on preparative HPLC to give 9 mg (29%) of the title compound as a white solid.

Workup

  1. customThe vial was sealed
  2. temperatureheated
  3. customThe crude mixture was purified on preparative HPLC

Sources & evidence

ORD record
ord-8f4fe226f98444298edfbccc6b42ec9e
Source dataset
uspto-grants-2013_04
Patent number
US08410114B2

Reaction notes

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