HCID 68673129, compound → HCID 178442434, compound

HRID 1927688Notes

Reaction equation

HRID 1927688 reaction equation
[CH3:1][C:2]([CH3:46])([CH2:44][CH3:45])[CH2:3][C:4]1[N:5]=[C:6]([CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=3)=[C:32]([O:42]C)[CH:31]=2)[N:7](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:8]=1>Br.C(O)(=O)C>[CH3:1][C:2]([CH3:46])([CH2:44][CH3:45])[CH2:3][C:4]1[N:5]=[C:6]([CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=3)=[C:32]([OH:42])[CH:31]=2)[NH:7][CH:8]=1

Participants

4

Reactant 1

HCID 68673129HCID 68673129, compound

Product 1

HCID 178442434HCID 178442434, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

A solution of 2-(4-{2-[4-(2,2-Dimethylbutyl)-1-trityl-1H-imidazol-2-yl]ethyl}-2-methoxyphenyl)pyridine (110 mg, 0.19 mmol) in 30% HBr in acetic acid (5 mL) was heated at reflux in a sealed tube for 6 hours. Upon cooling, the volatiles were removed, and the resulting residue was purified by flash column chromatography on silica gel eluting with 0-5% methanol/ammonium hydroxide mixture in methylene chloride to give the title compound, which was converted to the HCl salt with 1M HCl in diethyl ether. 1H NMR (500 MHz, CD3OD) δ 8.75-8.73 (δ, J=5.8 Hz, 1H) 8.57-8.54 (t, J=7.6 Hz, 1H), 8.35-8.32 (d, J=8.3 Hz, 1H), 7.92-7.88 (t, J=6.6 Hz, 1H), 7.75-7.72 (d, J=8.4 Hz, 1H), 7.17 (s, 1H), 6.92-6.90 (m, 2H), 3.40-3.30 (t, 2H, masked by solvent), 3.17-3.12 (t, J=7.0 Hz, 2H), 2.52 (s, 2H), 1.28-1.21 (q, J=7.7 Hz, 2H), 0.89-0.82 (m, 9H); LC-MS: m/e 350 (M+H).

Workup

  1. temperatureat reflux in a sealed tube for 6 hours
  2. temperatureUpon cooling
  3. customthe volatiles were removed
  4. customthe resulting residue was purified by flash column chromatography on silica gel eluting with 0-5% methanol/ammonium hydroxide mixture in methylene chloride

Sources & evidence

ORD record
ord-fcbc9cf4b65a4d2cad425e770b146eca
Source dataset
uspto-grants-2012_05
Patent number
US08183275B2

Reaction notes

Loading…