Telmisartan → 1-{[(2-{[(2R)-2,3-bis(nitrooxy)propyl]oxy}ethoxy)carbonyl]oxy}ethyl 4'-[(1,7'-dimethyl-2'-propyl-1H,3'H-2,5'-bibenzimidazol-3'-yl)methyl]biphenyl-2-carboxylate

HRID 1361918Notes

Reaction equation

HRID 1361918 reaction equation
[N+]([O-])(OC[C@H](O[N+]([O-])=O)CC[CH2:8][CH2:9][OH:10])=O.[N+:16]([O-:30])([O:18][CH2:19][C@H:20]([O:26][N+:27]([O-:29])=[O:28])[CH2:21][O:22][CH2:23][CH2:24][OH:25])=[O:17].C(C1N(CC2C=CC(C3C=CC=CC=3C3N(C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)N=NN=3)=CC=2)C([C:41](O)=[O:42])=C(Cl)N=1)CCC.[CH3:81][N:82]1[C:86]2[CH:87]=[CH:88][CH:89]=[CH:90][C:85]=2[N:84]=[C:83]1[C:91]1[CH:118]=[C:117]([CH3:119])[C:94]2[N:95]=[C:96]([CH2:114][CH2:115][CH3:116])[N:97]([CH2:98][C:99]3[CH:104]=[CH:103][C:102]([C:105]4[C:106]([C:111]([OH:113])=[O:112])=[CH:107][CH:108]=[CH:109][CH:110]=4)=[CH:101][CH:100]=3)[C:93]=2[CH:92]=1>>[CH3:81][N:82]1[C:86]2[CH:87]=[CH:88][CH:89]=[CH:90][C:85]=2[N:84]=[C:83]1[C:91]1[CH:118]=[C:117]([CH3:119])[C:94]2[N:95]=[C:96]([CH2:114][CH2:115][CH3:116])[N:97]([CH2:98][C:99]3[CH:100]=[CH:101][C:102]([C:105]4[C:106]([C:111]([O:113][CH:9]([O:10][C:41]([O:25][CH2:24][CH2:23][O:22][CH2:21][C@@H:20]([O:26][N+:27]([O-:29])=[O:28])[CH2:19][O:18][N+:16]([O-:30])=[O:17])=[O:42])[CH3:8])=[O:112])=[CH:107][CH:108]=[CH:109][CH:110]=4)=[CH:103][CH:104]=3)[C:93]=2[CH:92]=1

Participants

5

Reactant 4

HCID 65999TelmisartanHCID 467832052-Butyl-4-chloro-1-({2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl}methyl)-1H-imidazole-5-carboxylic acidHCID 59370633(2R)-3-(2-hydroxyethoxy)propane-1,2-diyl dinitrate2×HCID 59556786(2R)-6-hydroxyhexane-1,2-diyl dinitrate

Product 1

HCID 249893201-{[(2-{[(2R)-2,3-bis(nitrooxy)propyl]oxy}ethoxy)carbonyl]oxy}ethyl 4'-[(1,7'-dimethyl-2'-propyl-1H,3'H-2,5'-bibenzimidazol-3'-yl)methyl]biphenyl-2-carboxylate

Procedure

The title compound was prepared by following the procedure for example 1, except that the reagent (2R)-6-hydroxyhexane-1,2-diyl dinitrate was replaced by (2R)-3-(2-hydroxyethoxy)propane-1,2-diyl dinitrate (intermediate 5), and 2-butyl-4-chloro-1-{[2′-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-imidazole-5-carboxylic acid was replaced by 4′-[(1,7′-dimethyl-2′-propyl-1H,3′H-2,5′-bibenzimidazol-3′-yl)methyl]biphenyl-2-carboxylic acid. 1H NMR (300 MHz, CDCl3) δ 7.85 (m, 2H), 7.60-7.20 (m, 12H), 6.74 (q, 1H), 5.48 (s, 2H), 5.35 (m, 1H), 4.77 (m, 1H), 4.58 (m, 1H), 4.24 (t, 2H), 3.84 (s, 3H), 3.72 (m, 4H), 2.96 (t, 2H), 2.79 (s, 3H), 1.91 (m, 2H), 1.27 (d, 3H) 1.08 (t, 3H).

Sources & evidence

ORD record
ord-771721c4fa134ad3994b6823aaab806f
Source dataset
uspto-grants-2011_02
Patent number
US07880014B2

Reaction notes

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