Acetate-hydrochloric acid → HCID 178432627, compound

HRID 2377974Notes

Reaction equation

HRID 2377974 reaction equation
IC1C=CN=C(OC)C=1C1N(O)C(C2C=CC=CC=2)=C(C)N=1.[Cl:23][C:24]1[CH:25]=[C:26]([CH:30]([OH:53])[CH2:31][NH:32][C:33]2[CH:38]=[CH:37][NH:36][C:35](=[O:39])[C:34]=2[C:40]2[NH:41][C:42]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)=[C:43]([CH2:45]C)[N:44]=2)[CH:27]=[CH:28][CH:29]=1.Cl.C(O)(=O)C>[Cl-].[Ti+3].[Cl-].[Cl-]>[Cl:23][C:24]1[CH:25]=[C:26]([CH:30]([OH:53])[CH2:31][NH:32][C:33]2[CH:38]=[CH:37][NH:36][C:35](=[O:39])[C:34]=2[C:40]2[NH:41][C:42]([C:47]3[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=3)=[C:43]([CH3:45])[N:44]=2)[CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 22641269Acetate-hydrochloric acidHCID 598575802-(4-Iodo-2-methoxy-pyridin-3-yl)-4-methyl-5-phenyl-imidazol-1-olHCID 178437584HCID 178437584, compound

Product 1

HCID 178432627HCID 178432627, compound

Reagents, catalysts & solvents 1

HCID 10313229titanium(III) trichlorideCatalyst

Procedure

2-(4-Iodo-2-methoxy-pyridin-3-yl)-4-methyl-5-phenyl-imidazol-1-ol (0.093 g, 0.228 mmol) was reacted as described for the synthesis of 4-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-3-(4-ethyl-5-phenyl-1H-imidazol-2-yl)-1H-pyridin-2-one except that the compound was first treated with titanium(III) chloride and then hydrochloric acid/acetic acid. The title material was obtained (0.013 g, 14%) as a brown solid. HPLC 90.4% (220 nm), LCMS (+ESI, M+H+) m/z 421; IR ν (cm−1): 3276, 2920, 1643; HRMS calcd for C23H22N4O2Cl=421.1431, found: 421.1409; 1H NMR (400 MHz, methanol-d4) δ (ppm): 2.54 (3H, g), 3.64 (1H, dd, J=13.5 and 7.1 Hz), 3.70 (1H, dd, J=13.5 and 5.1 Hz), 4.97 (1H, t, J=5.8 Hz), 6.25 (1H, d, J=7.5 Hz), 7.21-7.68 (1OH, m), 7.71 (1H, d, J=8.0 Hz).

Sources & evidence

ORD record
ord-041b49fd2b1d4c4488175da02c8f1abf
Source dataset
uspto-grants-2008_12
Patent number
US07470713B2

Reaction notes

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