5-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazole → 2-butyl-5-pyrrol-1-yl-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]imidazole-4-carbonitrile

HRID 1197585Notes

Reaction equation

HRID 1197585 reaction equation
[CH2:1]([C:5]1[NH:6][C:7]([C:15]#[N:16])=[C:8]([N:10]2[CH:14]=[CH:13][CH:12]=[CH:11]2)[N:9]=1)[CH2:2][CH2:3][CH3:4].CC(C)([O-])C.[K+].C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[N:30]2[C:34]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[C:41]3[CH:46]=[CH:45][C:44]([CH2:47]Br)=[CH:43][CH:42]=3)=[N:33][N:32]=[N:31]2)C=CC=CC=1>O1CCCC1>[CH2:1]([C:5]1[N:6]([CH2:47][C:44]2[CH:45]=[CH:46][C:41]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=3[C:34]3[NH:30][N:31]=[N:32][N:33]=3)=[CH:42][CH:43]=2)[C:7]([C:15]#[N:16])=[C:8]([N:10]2[CH:11]=[CH:12][CH:13]=[CH:14]2)[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazoleHCID 149628802-Butyl-5-cyano-4-(1H-pyrrol-1-yl)imidazoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 1784417822-butyl-5-pyrrol-1-yl-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]imidazole-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 2-butyl-5-cyano-4-(1H-pyrrol-1-yl)imidazole (Example 8, 1.7 g) in anhydrous tetrahydrofuran (20 mL) was treated with a solution of potassium tert-butoxide (0.97 g) in anhydrous tetrahydrofuran (20 mL) at room temperature. The mixture was stirred for 5 minutes then a solution of N-triphenylmethyl-5-[4'-(bromomethyl)biphenyl-2-yl]tetrazole (Example 12, 6.0 g) in anhydrous tetrahydrofuran (20 mL) was added. The reaction was stirred at room temperature under nitrogen atmosphere for 18 hours. The resulting suspension was filtered and the filtrate was evaporated. The residue was purified by flash chromatography on silica gel, eluting with chloroform hexane (90:10) to give the title compound in its triphenylmethyl-protected form. The triphenylmethyl protecting group was removed by refluxing in methanol for 24 hours. Evaporation gave a residue that was purified by chromatography on silica gel, eluting with a gradient of ethyl acetate-hexane (50:50) to ethyl acetate. Evaporation of solvents gave a gum that was redissolved in dichloromethane and evaporated to give the title compound as a solid foam. MS (FAB, thioglycerol) 470 (m+Na-1), 448 (m).

Workup

  1. stirringThe reaction was stirred at room temperature under nitrogen atmosphere for 18 hours
  2. filtrationThe resulting suspension was filtered
  3. customthe filtrate was evaporated
  4. customThe residue was purified by flash chromatography on silica gel
  5. washeluting with chloroform hexane (90:10)

Sources & evidence

ORD record
ord-6632d4c307e04a9b8510c64f1e40f6a8
Source dataset
uspto-grants-1994_01
Patent number
US05276048

Reaction notes

Loading…