Isosorbide Mononitrate → (diethoxyphosphoryl)methyl 2-butyl-4-chloro-1-{[2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-imidazole-5-carboxylate

HRID 222541

Reaction equation

HRID 222541 reaction equation
C(C1N(CC2C=CC(C3C=CC=CC=3C3NN=NN=3)=CC=2)C(C(O)=O)=C(Cl)N=1)CCC.[CH2:32]([C:36]1[N:37]([CH2:45][C:46]2[CH:51]=[CH:50][C:49]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=3[C:58]3[N:62]([C:63]([C:76]4[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=4)([C:70]4[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=4)[C:64]4[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=4)[N:61]=[N:60][N:59]=3)=[CH:48][CH:47]=2)[C:38]([C:42]([OH:44])=[O:43])=[C:39]([Cl:41])[N:40]=1)[CH2:33][CH2:34][CH3:35].C1O[C@@H]2[C@H](O[N+]([O-])=O)CO[C@@H]2[C@H]1O.O[CH2:96][P:97](=[O:104])([O:101][CH2:102][CH3:103])[O:98][CH2:99][CH3:100]>>[CH2:32]([C:36]1[N:37]([CH2:45][C:46]2[CH:47]=[CH:48][C:49]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=3[C:58]3[N:62]([C:63]([C:70]4[CH:71]=[CH:72][CH:73]=[CH:74][CH:75]=4)([C:64]4[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=4)[C:76]4[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=4)[N:61]=[N:60][N:59]=3)=[CH:50][CH:51]=2)[C:38]([C:42]([O:44][CH2:96][P:97]([O:101][CH2:102][CH3:103])([O:98][CH2:99][CH3:100])=[O:104])=[O:43])=[C:39]([Cl:41])[N:40]=1)[CH2:33][CH2:34][CH3:35]

Participants

5

Reactant 4

HCID 27661Isosorbide MononitrateHCID 76513Diethyl phosphonomethanolHCID 467832052-Butyl-4-chloro-1-({2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl}methyl)-1H-imidazole-5-carboxylic acidHCID 178441712HCID 178441712, compound

Product 1

HCID 86652102(diethoxyphosphoryl)methyl 2-butyl-4-chloro-1-{[2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-imidazole-5-carboxylate

Procedure

The title compound was prepared by following example 7, except that the reagent 2-butyl-4-chloro-1-{[2′-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-imidazole-5-carboxylic acid was replaced by 2-butyl-4-chloro-1-{[2′-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-imidazole-5-carboxylic acid, and isosorbide-5-mononitrate was replaced by diethyl (hydroxymethyl)phosphonate. 1H NMR (500 MHz, CDCl3) δ 7.94 (d, J=7.4 Hz, 1H), 7.52 (td, J=7.1, 1.3 Hz, 1H), 7.48 (t, J=7.7 Hz, 1H), 7.39-7.34 (m, 4H), 7.28 (t, J=7.8 Hz, 6H), 7.13 (d, J=8.3 Hz, 2H), 6.95 (d, J=8.1 Hz, 6H), 6.80 (d, J=8.1 Hz, 2H), 5.47 (s, 2H), 4.49 (d, J=8.4 Hz, 2H), 4.24-4.16 (m, 4H), 2.53 (t, J=7.8 Hz, 2H), 1.67 (quintet, J=7.7 Hz, 2H), 1.33 (t, J=7.0 Hz, 6H), 1.30 (sextet, J=7.4 Hz, 2H), 0.88 (t, J=7.4 Hz, 3H).

Sources & evidence

ORD record
ord-7cfd724c5e8549af85b5236409ca6201
Source dataset
uspto-grants-2012_06
Patent number
US08207208B2

Linked notes

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