4-Amino-3-penten-2-one → HCID 68717311, compound

HRID 1947248Notes

Reaction equation

HRID 1947248 reaction equation
[C:1]([C:3]1[CH:24]=[CH:23][C:6]([CH:7]=[C:8]([C:14](=O)[CH:15]([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:5]([O:25][CH3:26])[CH:4]=1)#[N:2].[NH2:27][C:28]([CH3:33])=[CH:29][C:30](=[O:32])[CH3:31]>C(O)(C)C>[C:30]([C:29]1[CH:7]([C:6]2[CH:23]=[CH:24][C:3]([C:1]#[N:2])=[CH:4][C:5]=2[O:25][CH3:26])[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:14]([CH:15]([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])[NH:27][C:28]=1[CH3:33])(=[O:32])[CH3:31]

Participants

4

Reactant 2

HCID 1368734-Amino-3-penten-2-oneHCID 68717167HCID 68717167, compound

Product 1

HCID 68717311HCID 68717311, compoundYield 28.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

720 mg (1.992 mmol) of ethyl 2-(4-cyano-2-methoxybenzylidene)-4,4-diethoxy-3-oxobutanoate are taken up in 15 ml of isopropanol, 197.5 mg (4.84 mmol) of 4-amino-3-penten-2-one are added, and the mixture is heated at the reflux temperature overnight. The mixture is then concentrated and the residue is purified by preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 20:80→95:5). 250 mg (28.6% of theory) of ethyl 5-acetyl-4-(4-cyano-2-methoxyphenyl)-2-(diethoxymethyl)-6-methyl-1,4-dihydropyridine-3-carboxylate are obtained [LC-MS (method 11): Rt=2.48 min; [M+H]+ (EIpos): m/z=443].

Workup

  1. temperaturethe mixture is heated at the reflux temperature overnight
  2. concentrationThe mixture is then concentrated
  3. customthe residue is purified by preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 20:80→95:5)

Sources & evidence

ORD record
ord-0923011ca6bf4a8ea02a73d941ee7730
Source dataset
uspto-grants-2013_03
Patent number
US08399471B2

Reaction notes

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