Cyanoacetic acid → HCID 19736553, compound

HRID 326452Notes

Reaction equation

HRID 326452 reaction equation
[CH2:1]([C:5]1[N:6]([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[N:35]([C:36]([C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[N:34]=[N:33][N:32]=3)=[CH:21][CH:20]=2)[C:7]2[CH2:12][CH:11]([C:13]([O:15][CH3:16])=[O:14])[NH:10][CH2:9][C:8]=2[N:17]=1)[CH2:2][CH2:3][CH3:4].C1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1.[C:80]([CH2:82][C:83](O)=[O:84])#[N:81].C(=O)([O-])O.[Na+]>C(OCC)(=O)C.C(#N)C>[CH2:1]([C:5]1[N:6]([CH2:18][C:19]2[CH:20]=[CH:21][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]3[N:35]([C:36]([C:43]4[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=4)([C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)[C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)[N:34]=[N:33][N:32]=3)=[CH:23][CH:24]=2)[C:7]2[CH2:12][CH:11]([C:13]([O:15][CH3:16])=[O:14])[N:10]([C:83](=[O:84])[CH2:82][C:80]#[N:81])[CH2:9][C:8]=2[N:17]=1)[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 5

HCID 9740Cyanoacetic acidHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 19736554HCID 19736554, compound

Product 1

HCID 19736553HCID 19736553, compoundYield 93.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 2-n-butyl-1-{2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl}methyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-6-carboxylate (0.81 g), dicyclohexyl-carbodiimide (0.26 g), 1-hydroxybenzotriazole (0.17 g), cyanoacetic acid (0.11 g) and acetonitrile (10 ml) is stirred at room temperature overnight. After the reaction is completed, ethyl acetate is added to the reaction mixture, and the mixture is waehed with aqueous sodium hydrogen carbonate solution, dried, and the solvent is distilled off under reduced pressure. The resulting residue is purified by silica gel column chromatography (solvent; ethyl acetate) to give methyl 2-n-butyl-5-cyanoacetyl-1-{2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl}methyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-6-carboxylate (0.83 g) as foam.

Workup

  1. customdried
  2. distillationthe solvent is distilled off under reduced pressure
  3. customThe resulting residue is purified by silica gel column chromatography (solvent; ethyl acetate)

Sources & evidence

ORD record
ord-adaf8ab1e0124c6b8eb08776ed52924e
Source dataset
uspto-grants-1993_12
Patent number
US05268377

Reaction notes

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