Carbamimidoyl-acetic acid ethyl ester → 2,6-Diamino-4-(3-carbethoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester

HRID 328227Notes

Reaction equation

HRID 328227 reaction equation
[C:1]([C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=O)([O:3][CH2:4][CH3:5])=[O:2].[CH2:14]([O:16][C:17](=[O:22])[CH2:18][C:19](=[NH:21])[NH2:20])[CH3:15]>C(O)C>[CH2:14]([O:16][C:17]([C:18]1[CH:9]([C:8]2[CH:11]=[CH:12][CH:13]=[C:6]([C:1]([O:3][CH2:4][CH3:5])=[O:2])[CH:7]=2)[C:18]([C:17]([O:16][CH2:14][CH3:15])=[O:22])=[C:19]([NH2:20])[NH:21][C:19]=1[NH2:20])=[O:22])[CH3:15]

Participants

4

Reactant 2

HCID 4599837Carbamimidoyl-acetic acid ethyl esterHCID 11084437Ethyl 3-formylbenzoate

Product 1

HCID 706316882,6-Diamino-4-(3-carbethoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl esterYield 32%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Upon boiling a solution of 8.9 g 3-carbethoxybenzaldehyde and 13.0 g amidinoacetic acid ethyl ester in 100 ml ethanol for two hours, 2,6-diamino-4-(3-carbethoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester of m.p. 191° C (ethanol) is obtained.

Workup

  1. customfor two hours

Sources & evidence

ORD record
ord-79cb986292e44f239e7bf689c5ed5784
Source dataset
uspto-grants-1977_04
Patent number
US04016277

Reaction notes

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