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

HRID 1951551Notes

Reaction equation

HRID 1951551 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:18]1[S:19][CH:20]=[C:21]([CH3:23])[N:22]=1)[C:13](=O)[CH2:14][O:15][CH3:16])[C:6]#[N:7].[NH2:24]/[C:25](/[CH3:29])=[CH:26]\[C:27]#[N:28]>C(O)(C)C>[C:6]([C:5]1[CH:8]=[CH:9][C:10]([CH:11]2[C:12]([C:18]3[S:19][CH:20]=[C:21]([CH3:23])[N:22]=3)=[C:13]([CH2:14][O:15][CH3:16])[NH:24][C:25]([CH3:29])=[C:26]2[C:27]#[N:28])=[C:3]([O:2][CH3:1])[CH:4]=1)#[N:7]

Participants

4

Reactant 2

HCID 5325263(2Z)-3-Amino-2-butenenitrileHCID 670179713-Methoxy-4-[4-methoxy-2-(4-methyl-1,3-thiazol-2-yl)-3-oxobut-1-en-1-yl]benzonitrile

Product 1

HCID 1358449684-(4-Cyano-2-methoxyphenyl)-6-(methoxymethyl)-2-methyl-5-(4-methyl-1,3-thiazol-2-yl)-1,4-dihydropyridine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

100 mg (0.305 mmol) of the compound from example 14A and 25 mg (0.305 mmol) of 3-amino-crotononitrile are dissolved in 3 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). 59 mg (49% 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-325fde52b85746ee823ebfe4d09b327e
Source dataset
uspto-grants-2013_03
Patent number
US08404723B2

Reaction notes

Loading…