Isopropyl acetoacetate → 1,4-Dihydro-2,6-dimethyl-4-thieno[3,2-c]pyridin-3-yl-3,5-pyridinedicarboxylic acid, 3-ethyl 5-isopropyl ester

HRID 542775Notes

Reaction equation

HRID 542775 reaction equation
[S:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[C:3]([CH:10]=O)=[CH:2]1.[C:12]([O:18][CH:19]([CH3:21])[CH3:20])(=[O:17])[CH2:13][C:14]([CH3:16])=O.[NH2:22]/[C:23](/[CH3:30])=[CH:24]\[C:25]([O:27][CH2:28][CH3:29])=[O:26]>C(O)C>[CH3:30][C:23]1[NH:22][C:14]([CH3:16])=[C:13]([C:12]([O:18][CH:19]([CH3:21])[CH3:20])=[O:17])[CH:10]([C:3]2[C:4]3[CH:5]=[N:6][CH:7]=[CH:8][C:9]=3[S:1][CH:2]=2)[C:24]=1[C:25]([O:27][CH2:28][CH3:29])=[O:26]

Participants

5

Reactant 3

HCID 68329Isopropyl acetoacetateHCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 15718106Thieno[3,2-c]pyridine-3-carboxaldehyde

Product 1

HCID 138268691,4-Dihydro-2,6-dimethyl-4-thieno[3,2-c]pyridin-3-yl-3,5-pyridinedicarboxylic acid, 3-ethyl 5-isopropyl esterYield 29.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1 g of thieno[3,2-c]pyridine-3-carboxaldehyde, 1.08 g of isopropyl acetoacetate, and 0.9 g of ethyl 3-aminocrotonate in 4 ml of ethanol was heated to reflux for approximately 18 hours. Upon cooling, a solid formed which was recovered by filtration providing 0.73 g of the desired title product, m.p. 212°-215° C.

Workup

  1. temperatureto reflux for approximately 18 hours
  2. temperatureUpon cooling
  3. customa solid formed which
  4. filtrationwas recovered by filtration

Sources & evidence

ORD record
ord-08b630dadfd04a1c9446120afa8a8211
Source dataset
uspto-grants-1987_04
Patent number
US04659717

Reaction notes

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