1-[({[5,6-bis(nitrooxy)hexyl]oxy}carbonyl)oxy]-1-methylethyl 2-ethoxy-1-{[2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-benzimidazole-7-carboxylate → HCID 178467366, compound

HRID 1361917Notes

Reaction equation

HRID 1361917 reaction equation
[CH2:1]([O:3][C:4]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]3[N:26](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:25]=[N:24][N:23]=3)=[CH:12][CH:11]=2)[C:7]2[C:46]([C:50]([O:52][C:53]([O:56][C:57]([O:59][CH2:60][CH2:61][CH2:62][CH2:63][CH:64]([O:70][N+:71]([O-:73])=[O:72])[CH2:65][O:66][N+:67]([O-:69])=[O:68])=[O:58])([CH3:55])[CH3:54])=[O:51])=[CH:47][CH:48]=[CH:49][C:6]=2[N:5]=1)[CH3:2]>ClCCl.CO>[CH2:1]([O:3][C:4]1[N:8]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]3[NH:23][N:24]=[N:25][N:26]=3)=[CH:14][CH:15]=2)[C:7]2[C:46]([C:50]([O:52][C:53]([O:56][C:57]([O:59][CH2:60][CH2:61][CH2:62][CH2:63][CH:64]([O:70][N+:71]([O-:73])=[O:72])[CH2:65][O:66][N+:67]([O-:69])=[O:68])=[O:58])([CH3:55])[CH3:54])=[O:51])=[CH:47][CH:48]=[CH:49][C:6]=2[N:5]=1)[CH3:2]

Participants

3

Reactant 1

HCID 866225351-[({[5,6-bis(nitrooxy)hexyl]oxy}carbonyl)oxy]-1-methylethyl 2-ethoxy-1-{[2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-benzimidazole-7-carboxylate

Product 1

HCID 178467366HCID 178467366, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

A dichloromethane/methanol (3.5 mL, 1:7) solution of 1-[({[5,6-bis(nitrooxy)hexyl]oxy}carbonyl)oxy]-1-methylethyl 2-ethoxy-1-{[2′-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-benzimidazole-7-carboxylate (0.190 g, 0.192 mmol) was heated in a microwave apparatus (90° C., 20 minutes). Then the solution was concentrated and the residue was purified by flash chromatography (Biotage SP1, 25+M column, dichloromethane/methanol 98/2), affording the title compound. 1H NMR (300 MHz, CDCl3) δ 8.04-8.01 (m, 1H), 7.63-7.61 (m, 2H), 7.52 (dd, 1H), 7.32-7.28 (m, 1H), 6.91 (t, 1H), 6.81 (d, 3H), 6.68 (d, 2H), 5.62 (s, 2H), 5.25-5.23 (m, 1H), 4.72 (dd, 1H), 4.28-4.26 (m, 2H), 4.05 (t, 2H), 1.78-1.52 (m, 10H), 1.49-1.42 (m, 6H).

Workup

  1. concentrationThen the solution was concentrated
  2. customthe residue was purified by flash chromatography (Biotage SP1, 25+M column, dichloromethane/methanol 98/2)

Sources & evidence

ORD record
ord-2294cdc0a408495d9f5eb6170fed7d68
Source dataset
uspto-grants-2011_02
Patent number
US07880014B2

Reaction notes

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