(2Z)-3-Amino-2-butenenitrile → 4-(4-Cyano-2-methoxyphenyl)-2,6-dimethyl-5-(5-methyl-1,3,4-thiadiazol-2-yl)-1,4-dihydropyridine-3-carbonitrile
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[CH:11]=[C:12]([C:16]1[S:17][C:18]([CH3:21])=[N:19][N:20]=1)[C:13](=O)[CH3:14])[C:6]#[N:7].[NH2:22]/[C:23](/[CH3:27])=[CH:24]\[C:25]#[N:26]>C(O)(C)C>[C:6]([C:5]1[CH:8]=[CH:9][C:10]([CH:11]2[C:12]([C:16]3[S:17][C:18]([CH3:21])=[N:19][N:20]=3)=[C:13]([CH3:14])[NH:22][C:23]([CH3:27])=[C:24]2[C:25]#[N:26])=[C:3]([O:2][CH3:1])[CH:4]=1)#[N:7]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
150 mg (0.501 mmol) of the compound from example 25A and 41 mg (0.501 mmol) of 3-amino-crotononitrile are dissolved in 5 ml of isopropanol and stirred at the reflux temperature overnight. After cooling to room temperature, the volatile components are removed in a rotary evaporator, and the crude product is purified by preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 20:80→95:5). Crystallization from ethyl acetate/diethyl ether results in 30 mg (16% of theory) of the title compound.