5-Amino-2-(piperidin-1-yl)benzonitrile → N-(3-Cyano-4-piperidinophenyl)-1,5-dimethylpyrazole-4-carboxamide

HRID 1744552Notes

Reaction equation

[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([C:8]([OH:10])=O)[CH:4]=[N:3]1.ON1C2C=CC=CC=2N=N1.[NH2:21][C:22]1[CH:23]=[CH:24][C:25]([N:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)=[C:26]([CH:29]=1)[C:27]#[N:28]>C(O)C>[C:27]([C:26]1[CH:29]=[C:22]([NH:21][C:8]([C:5]2[CH:4]=[N:3][N:2]([CH3:1])[C:6]=2[CH3:7])=[O:10])[CH:23]=[CH:24][C:25]=1[N:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1)#[N:28]

Participants

Conditions

Temperature: 78 °C

Procedure

1-Hydroxybenzotriazole 1,5-dimethylpyrazole-4-carboxylate (1.2 g) and 5-amino-2-piperidinobenzonitrile (0.9 g) were added to ethanol (20 ml) and the mixture was stirred at 78° C. for 3 h. After evaporation of the solvent, aqueous potassium carbonate solution was added to the residue and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. n-Hexane was added to the residue to allow crystallization. The crystals were recrystallized from hydrous ethanol to give the title compound (0.7 g), melting point: 217–218° C.

Workup

customAfter evaporation of the solvent, aqueous potassium carbonate solution
additionwas added to the residue
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customafter which the solvent was evaporated under reduced pressure
additionn-Hexane was added to the residue
customcrystallization
customThe crystals were recrystallized from hydrous ethanol

Sources & evidence

ORD record: ord-21eeb7599b8c4d37a0462f8b5b9a2398
Source dataset: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07015218B1

Reaction notes

Loading…