(2Z)-3-Amino-2-butenenitrile → 4-(4-Cyano-2-methoxyphenyl)-2,6-dimethyl-5-(4-methyl-1,3-thiazol-2-yl)-1,4-dihydropyridine-3-carbonitrile
Reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[O:11][CH3:12])=O.[CH3:13][C:14]1[N:15]=[C:16]([CH2:19][C:20]([CH3:22])=O)[S:17][CH:18]=1.[NH2:23]/[C:24](/[CH3:28])=[CH:25]\[C:26]#[N:27]>C(O)(C)C>[C:7]([C:6]1[CH:9]=[CH:10][C:3]([CH:1]2[C:19]([C:16]3[S:17][CH:18]=[C:14]([CH3:13])[N:15]=3)=[C:20]([CH3:22])[NH:23][C:24]([CH3:28])=[C:25]2[C:26]#[N:27])=[C:4]([O:11][CH3:12])[CH:5]=1)#[N:8]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
800 mg (4.96 mmol) of the compound from example 3A, 770 mg (4.96 mmol) of the compound from example 4A and 407 mg (4.96 mmol) of 3-aminocrotononitrile are dissolved in 12 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 taken up in 20 ml of ethyl acetate. After stirring at the reflux temperature for 60 min, the resulting solid is filtered off hot. The precipitate obtained in this way is washed with a little diethyl ether. 720 mg (40% of theory) of the title compound are obtained.
Workup
- customthe volatile components are removed in a rotary evaporator
- stirringAfter stirring at the reflux temperature for 60 min
- filtrationthe resulting solid is filtered off hot
- customThe precipitate obtained in this way
- washis washed with a little diethyl ether
Sources & evidence
- ORD record
- ord-f25b6f896a5e41a8a3c32823b71f22bc
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08404723B2
Reaction notes
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