Isobutyl acetoacetate → 4-(2,1,3-Benzoxadiazol-4-yl)-2,6-dimethyl-1,4-dihydro-3-methoxy carbonyl-pyridine-5-carboxylic acid isobutyl ester

HRID 1285533

Reaction equation

HRID 1285533 reaction equation
[N:1]1[O:2][N:3]=[C:4]2[C:9]([CH:10]=O)=[CH:8][CH:7]=[CH:6][C:5]=12.[CH2:12]([O:16][C:17](=[O:22])[CH2:18][C:19]([CH3:21])=O)[CH:13]([CH3:15])[CH3:14].[CH3:23][O:24][C:25](=[O:30])/[CH:26]=[C:27](\[NH2:29])/[CH3:28]>C(O)C>[CH2:12]([O:16][C:17]([C:18]1[CH:10]([C:9]2[C:4]3[C:5](=[N:1][O:2][N:3]=3)[CH:6]=[CH:7][CH:8]=2)[C:26]([C:25]([O:24][CH3:23])=[O:30])=[C:27]([CH3:28])[NH:29][C:19]=1[CH3:21])=[O:22])[CH:13]([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 522677Isobutyl acetoacetateHCID 643918Methyl 3-aminocrotonateHCID 102908732,1,3-Benzoxadiazole-4-carbaldehyde

Product 1

HCID 132311024-(2,1,3-Benzoxadiazol-4-yl)-2,6-dimethyl-1,4-dihydro-3-methoxy carbonyl-pyridine-5-carboxylic acid isobutyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3 g of 2,1,3-benzoxadiazole-4-aldehyde, 3.2 g of acetoacetic acid isobutyl ester, 2.3 g β-aminocrotonic acid methyl ester and 10 ml of ethanol are stirred under reflux for 3 hours. The mixture is subsequently evaporated and the residue is chromatographed on silica gel with chloroform/acetic acid ethyl ester (8:1) to yield the title compound. The product is recrystallised from diisopropyl ether and methylcyclohexane, m.p. 148°-158°.

Workup

  1. temperatureunder reflux for 3 hours
  2. customThe mixture is subsequently evaporated
  3. customthe residue is chromatographed on silica gel with chloroform/acetic acid ethyl ester (8:1)

Sources & evidence

ORD record
ord-19f56ac2a5814730b77eb37b2ee022b9
Source dataset
uspto-grants-1986_01
Patent number
US04567271

Linked notes

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