(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

HRID 1951562Notes

Reaction equation

HRID 1951562 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

HCID 5325263(2Z)-3-Amino-2-butenenitrileHCID 670179873-Methoxy-4-[2-(5-methyl-1,3,4-thiadiazol-2-yl)-3-oxobut-1-en-1-yl]benzonitrile

Product 1

HCID 1358449834-(4-Cyano-2-methoxyphenyl)-2,6-dimethyl-5-(5-methyl-1,3,4-thiadiazol-2-yl)-1,4-dihydropyridine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

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.

Workup

  1. customthe volatile components are removed in a rotary evaporator
  2. customthe crude product is purified by preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 20:80→95:5)
  3. customCrystallization from ethyl acetate/diethyl ether

Sources & evidence

ORD record
ord-02ed827ae5964fb7afd0e7fa87586d13
Source dataset
uspto-grants-2013_03
Patent number
US08404723B2

Reaction notes

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