Cyanoacetic acid → HCID 178439977, compound

HRID 326460Notes

Reaction equation

HRID 326460 reaction equation
[CH2:1]([C:4]1[N:17]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]3[NH:35][N:34]=[N:33][N:32]=3)=[CH:21][CH:20]=2)[C:7]2[CH:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:9][CH2:10][CH2:11][C:6]=2[N:5]=1)[CH2:2][CH3:3].[C:36]([CH2:38][C:39](O)=[O:40])#[N:37].Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[CH2:1]([C:4]1[N:17]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]3[NH:35][N:34]=[N:33][N:32]=3)=[CH:21][CH:20]=2)[C:7]2[CH:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:9]([C:39](=[O:40])[CH2:38][C:36]#[N:37])[CH2:10][CH2:11][C:6]=2[N:5]=1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 9740Cyanoacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178439973HCID 178439973, compound

Product 1

HCID 178439977HCID 178439977, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of ethyl 2-n-propyl-3-{2'-(1H-tetrazol-5-yl)biphenyl-4-yl}methyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-4-carboxylate (1.00 g), cyanoacetic acid (0.36 g) and methylene chloride (20 ml) is added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.82 g) at room temperature. The reaction mixture is stirred overnight at room temperature, and then washed with 2% aqueous hydrochloric acid and brine. The organic layer is dried and evaporated to remove the solvent. The crude residue is purified by silica gel column chromatography (solvent; chloroform/methanol) to give ethyl 2-n-propyl-3-{2'-(1H-tetrazol-5-yl)biphenyl-4-yl}methyl-5-cyanoacetyl-4,5,6,7-tetrahydroimidazo[4,5-c}pyridine-4-carboxylate (0.76 g) as white foam.

Workup

  1. washwashed with 2% aqueous hydrochloric acid and brine
  2. customThe organic layer is dried
  3. customevaporated
  4. customto remove the solvent
  5. customThe crude residue is purified by silica gel column chromatography (solvent; chloroform/methanol)

Sources & evidence

ORD record
ord-70f59cb0afdc4151aec694a3ff6272a4
Source dataset
uspto-grants-1993_12
Patent number
US05268377

Reaction notes

Loading…