Sodium hydride → HCID 15222104, compound

HRID 1707762Notes

Reaction equation

HRID 1707762 reaction equation
[H-].[Na+].[C:3]([C:7]1[N:8]=[C:9]([CH2:16][CH2:17][CH3:18])[NH:10][C:11]=1[C:12]([O:14][CH3:15])=[O:13])([O:5][CH3:6])=[O:4].Br[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:33]2[N:37]([C:38]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[N:36]=[N:35][N:34]=2)=[CH:23][CH:22]=1>CN(C=O)C>[C:12]([C:11]1[N:10]=[C:9]([CH2:16][CH2:17][CH3:18])[N:8]([CH2:20][C:21]2[CH:22]=[CH:23][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]3[N:37]([C:38]([C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)([C:45]4[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=4)[C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[N:36]=[N:35][N:34]=3)=[CH:25][CH:26]=2)[C:7]=1[C:3]([O:5][CH3:6])=[O:4])([O:14][CH3:15])=[O:13]

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazoleHCID 15222105Dimethyl 2-propyl-1H-imidazole-4,5-dicarboxylate

Product 1

HCID 15222104HCID 15222104, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

Sodium hydride (1.06 g, 44.2 mmol, 1 eq) was added to a solution of 4,5-dicarbomethoxy-2-n-propylimidazole (10.00 g, 44.2 mmol, 1 eq) in DMF at room temperature. Foaming and gas evolution occurred. The temperature was increased to 60° C. for 15 minutes to dissolve all of the sodium hydride. Gas evolution ceased and the mixture was cooled to room temperature. To this mixture was added a DMF solution of 4-bromomethyl-2'-(N-triphenylmethyl-(1H-tetrazol-5-yl))biphenyl (24.64 g, 44.2 mmol, 1 eq). After 24 h, the solvent was removed in vacuo, and the residue was flash chromatographed in 75:25 hexane/ethyl acetate to 100% ethyl acetate over silica gel to yield 15.78 g (51%) of a white glass which was suitable for further transformation. Recrystallization from ethanol yielded an analytical sample (white crystals); top: 124.0°-125.5° C. NMR (CDCl3) δ 7.91 (d of d,1H,J=3,9 Hz); 7.59-7.20 (m12H); 7.09 (d,2H,J=9Hz); 6.94 (m, 6H); 6.76 (d,2H,J=9Hz); 5.30 (s,2H); 3.89 (s,3H); 2.50 (t,2H,J=7Hz); 1.67 (t of t, 2H,J=7,7Hz); 0.85 (t,3H,J=7Hz). IR (neat) 1718 cm-1. Anal. calcd. for C43H38N6O4 : C, 73.49; H, 5.45; N, 11.96. Found: C, 73.23; H, 5.48; N, 12.22. ##STR78##

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. customthe solvent was removed in vacuo
  3. customchromatographed in 75:25 hexane/ethyl acetate to 100% ethyl acetate over silica gel

Sources & evidence

ORD record
ord-ab1c501d96704e57b4665874e90e2917
Source dataset
uspto-grants-1994_10
Patent number
US05354867

Reaction notes

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