(2Z)-3-Amino-2-butenenitrile → 4-(4-Cyano-2-methoxyphenyl)-6-ethyl-2-methyl-5-(4-methyl-1,3-thiazol-2-yl)-1,4-dihydropyridine-3-carbonitrile

HRID 1951545Notes

Reaction equation

HRID 1951545 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](=O)[CH2:21][CH3:22])[S:17][CH:18]=1.[NH2:24]/[C:25](/[CH3:29])=[CH:26]\[C:27]#[N:28]>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]([CH2:21][CH3:22])[NH:24][C:25]([CH3:29])=[C:26]2[C:27]#[N:28])=[C:4]([O:11][CH3:12])[CH:5]=1)#[N:8]

Participants

5

Reactant 3

HCID 5325263(2Z)-3-Amino-2-butenenitrileHCID 166592514-Formyl-3-methoxybenzonitrileHCID 594923371-(4-Methyl-1,3-thiazol-2-yl)butan-2-one

Product 1

HCID 1358449614-(4-Cyano-2-methoxyphenyl)-6-ethyl-2-methyl-5-(4-methyl-1,3-thiazol-2-yl)-1,4-dihydropyridine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

100 mg (0.620 mmol) of the compound from example 3A, 100 mg (0.310 mmol, 50% purity) of the compound from example 5A and 51 mg (0.620 mmol) of 3-aminocrotononitrile are dissolved in 4 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). 78 mg (66% of theory) of the title compound are obtained.

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)

Sources & evidence

ORD record
ord-34dfbf5742e74ed1a39e39d638163559
Source dataset
uspto-grants-2013_03
Patent number
US08404723B2

Reaction notes

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