HCID 19932982, compound → ethyl 2-n-propyl-3-[2'-(1-trityl-1 H-tetrazol-5-yl)biphenyl-4-yl]methyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-4-carboxylate

HRID 1655130Notes

Reaction equation

HRID 1655130 reaction equation
[CH2:1]([C:4]1[N:5]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]3[N:29]([C:30]([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)[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[N:28]=[N:27][N:26]=3)=[CH:15][CH:14]=2)[CH:6]=[C:7]([CH2:9][CH2:10][NH2:11])[N:8]=1)[CH2:2][CH3:3].O.[C:50]([O:54][CH2:55][CH3:56])(=[O:53])[CH:51]=O>O1CCCC1>[CH2:1]([C:4]1[N:5]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]3[N:29]([C:30]([C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[N:28]=[N:27][N:26]=3)=[CH:17][CH:18]=2)[C:6]2[CH:51]([C:50]([O:54][CH2:55][CH3:56])=[O:53])[NH:11][CH2:10][CH2:9][C:7]=2[N:8]=1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 19932982HCID 19932982, compoundHCID 22414697Ethyl glyoxylate hydrate

Product 1

HCID 15291714ethyl 2-n-propyl-3-[2'-(1-trityl-1 H-tetrazol-5-yl)biphenyl-4-yl]methyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-4-carboxylateYield 68.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-n-propyl-4-(2-aminoethyl)-1-[2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methylimidazole (6.92 g), ethyl glyoxylate hydrate (1.30 g) and tetrahydrofuran (70 ml) is stirred overnight at room temperature. The mixture is evaporated, and the residue is purified by silica gel column chromatography (solvent; chloroform/ethanol) to give ethyl 2-n-propyl-3-[2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-4-carboxylate (5.32 g) as a foam.

Workup

  1. customThe mixture is evaporated
  2. customthe residue is purified by silica gel column chromatography (solvent; chloroform/ethanol)

Sources & evidence

ORD record
ord-988a3b767e8744bc8866a6694c63b63c
Source dataset
uspto-grants-1995_04
Patent number
US05409936

Reaction notes

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