Cyclopropylamine → 6-[1-(6-Cyanopyridin-3-yl)-1H-pyrazol-5-yl]-N-cyclopropyl-5-methyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxamide

HRID 1958303Notes

Reaction equation

HRID 1958303 reaction equation
[C:1]([C:3]1[N:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[N:19]=[C:18]([C:20]([O:22]C)=O)[C:17](=[O:24])[N:16]([C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=4)[C:15]=3[CH3:35])=[CH:12][CH:11]=[N:10]2)=[CH:5][CH:4]=1)#[N:2].[CH:36]1([NH2:39])[CH2:38][CH2:37]1>C(#N)C.C(O)C>[C:1]([C:3]1[N:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[N:19]=[C:18]([C:20]([NH:39][CH:36]4[CH2:38][CH2:37]4)=[O:22])[C:17](=[O:24])[N:16]([C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:33])([F:34])[F:32])[CH:26]=4)[C:15]=3[CH3:35])=[CH:12][CH:11]=[N:10]2)=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 2

HCID 69828CyclopropylamineHCID 66738829Methyl 6-[1-(6-cyanopyridin-3-yl)-1H-pyrazol-5-yl]-5-methyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxylate

Product 1

HCID 248904856-[1-(6-Cyanopyridin-3-yl)-1H-pyrazol-5-yl]-N-cyclopropyl-5-methyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxamideYield 37%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 6-[1-(6-cyanopyridin-3-yl)-1H-pyrazol-5-yl]-5-methyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxylate (0.026 g, 0.054 mmol) in acetonitrile (0.33 ml) and ethanol (0.074 ml) were placed in a vial. Cyclopropylamine (0.14 ml, 2.0 mmol) was added, the vial sealed and stirred at 60° C. for 10 h. After evaporation, the residue was purified by preparative HPLC to give 0.010 g (37%) of the title compound.

Workup

  1. customthe vial sealed
  2. customAfter evaporation
  3. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-55eb21fe73c847ffa7b6a8ce8dcccc12
Source dataset
uspto-grants-2013_04
Patent number
US08410114B2

Reaction notes

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