Sodium hydride → methyl 5-diphenylacetyl-3-[2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-4-carboxylate

HRID 21853Notes

Reaction equation

HRID 21853 reaction equation
[C:1]1([CH:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:8]([N:10]2[CH2:15][CH2:14][C:13]3[NH:16][CH:17]=[N:18][C:12]=3[CH:11]2[C:19]([O:21][CH3:22])=[O:20])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[C:31]([N:50]1[C:54]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][C:56]=2[C:61]2[CH:66]=[CH:65][C:64]([CH2:67]Br)=[CH:63][CH:62]=2)=[N:53][N:52]=[N:51]1)([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C)C=O>[C:23]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]([N:10]2[CH2:15][CH2:14][C:13]3[N:16]=[CH:17][N:18]([CH2:67][C:64]4[CH:63]=[CH:62][C:61]([C:56]5[CH:57]=[CH:58][CH:59]=[CH:60][C:55]=5[C:54]5[N:50]([C:31]([C:44]6[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=6)([C:38]6[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=6)[C:32]6[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=6)[N:51]=[N:52][N:53]=5)=[CH:66][CH:65]=4)[C:12]=3[CH:11]2[C:19]([O:21][CH3:22])=[O:20])=[O:9])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazoleHCID 15291695Methyl 5-diphenylacetyl-4,5,6,7-tetrahydroimidazo-[4,5-c]pyridine-4-carboxylate

Product 1

HCID 15291696methyl 5-diphenylacetyl-3-[2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-4-carboxylateYield 11.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 5-diphenylacetyl-4,5,6,7-tetrahydroimidazo-[4,5-c]pyridine-4-carboxylate (1.60 g) is dissolved in dimethylformamide (20 ml), and thereto is added sodium hydride (60% oil-dispersion, 176 mg) under ice-cooling. The mixture is stirred at 0° C. for 20 minutes, and thereto is added [2'-(1-trityl-1H-tetrazol-5-yl)bipheyl-4-yl]methyl bromide (2.40 g), and the mixture is stirred under ice-cooling for one hour, and further at room temperature for one hour. The reaction solution is concentrated under reduced pressure, and to the residue are added chloroform and water. The organic layer is dried, and evaporated to remove the solvent. The resulting residue is purified by silica gel column chromatography (solvent; chloroform/methanol=100:1) to give methyl 5-diphenylacetyl-3-[2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-4-carboxylate (430 mg) as a colorless foam.

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred under ice-
  3. temperaturecooling for one hour
  4. waitfurther at room temperature for one hour
  5. concentrationThe reaction solution is concentrated under reduced pressure
  6. additionto the residue are added chloroform and water
  7. customThe organic layer is dried
  8. customevaporated
  9. customto remove the solvent
  10. customThe resulting residue is purified by silica gel column chromatography (solvent; chloroform/methanol=100:1)

Sources & evidence

ORD record
ord-c41500c146aa4c8fb9484ec1dc825c47
Source dataset
uspto-grants-1995_06
Patent number
US05424316

Reaction notes

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