Hydrochloric Acid → HCID 135483507, compound

HRID 2377975Notes

Reaction equation

HRID 2377975 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12](O)[C:11]([C:14]3[C:15](=[O:31])[NH:16][CH:17]=[CH:18][C:19]=3[NH:20][CH2:21][CH:22]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=3)[OH:23])=[N:10][CH:9]=2)=[CH:4][CH:3]=1.Cl>CO.[Cl-].[Ti+3].[Cl-].[Cl-]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([C:14]3[C:15](=[O:31])[NH:16][CH:17]=[CH:18][C:19]=3[NH:20][CH2:21][CH:22]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=3)[OH:23])=[N:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 136331968HCID 136331968, compound

Product 1

HCID 135483507HCID 135483507, compoundYield 41.2%

Reagents, catalysts & solvents 2

HCID 10313229titanium(III) trichlorideCatalystHCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a stirred solution of 3-[5-(4-bromo-phenyl)-1-hydroxy-1H-imidazol-2-yl]-4-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-1H-pyridin-2-one (0.015 g, 0.030 mmol) in methanol (4 mL) was treated with titanium(III) chloride ((9.25 wt % in 27.4 wt % hydrochloric acid, ˜200 μL). The reaction was heated at 65° C. for 1 hour, then quenched with water and the solvents were evaporated. The residue was purified by Prep HPLC (ammonium acetate/acetonitrile/water) to give the title material (0.006 g, 41%) as a beige solid. HPLC 100% (220 nm), LCMS (+ESI, M+H+) m/z 485,487, (−ESI, M−H−) m/z 483, 485; 1H NMR (400 MHz, methanol-d4) δ (ppm): 3.64 (1H, dd, J=13.3 and 7.1 Hz), 3.74 (1H, dd, J=13.3 and 4.5 Hz), 5.03 (1H, m), 6.26 (1H, d, J=7.5 Hz), 7.23-7.56 (9H, m), 7.77 (1H, d, J=8.6 Hz).

Workup

  1. customquenched with water
  2. customthe solvents were evaporated
  3. customThe residue was purified by Prep HPLC (ammonium acetate/acetonitrile/water)

Sources & evidence

ORD record
ord-6f98d53d4819489083fccb151e4ac8ff
Source dataset
uspto-grants-2008_12
Patent number
US07470713B2

Reaction notes

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