Potassium Carbonate → HCID 67371851, compound

HRID 1375374Notes

Reaction equation

[CH2:1]([N:5]1[C:9]([CH2:10]O)=[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[NH:7][CH:6]1[I:18])[CH2:2][CH2:3][CH3:4].O=S(Cl)Cl.[CH2:23]([O:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29][NH2:30])[CH3:24].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.CN(C=O)C>[CH2:1]([N:5]1[C:9]([CH2:10][NH:30][CH2:29][C:28]2[CH:31]=[CH:32][CH:33]=[C:26]([O:25][CH2:23][CH3:24])[CH:27]=2)=[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[NH:7][CH:6]1[I:18])[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 0 °C

Procedure

(1-Butyl-2-iodo-4-phenyl-3H-imidazol-5-yl)-methanol (1.96 g), prepared by the method given in Example 2, step 2, is dissolved in 20 mL CH2Cl2. The solution is cooled to 0° C. and 3 equivalents of SOCl2 are added. The resulting solution is stirred at room temperature for 2 hours and then evaporated to dryness. The residue is dissolved in 5 mL of DMF and added to an ice cooled solution of 2 equivalents of 3-ethoxybenzylamine and 2 equivalents K2CO3 in 10 mL DMF. The mixture is stirred overnight at room temperature. The reaction is quenched with 20 mL water, extracted with EtOAc (3×30 mL), washed with water and brine, and dried over Na2SO4. Concentration and purification via silica gel chromatography provides (1-Butyl-2-iodo-4-phenyl-3H-imidazol-5-ylmethyl)-(3-ethoxy-benzyl)-amine.

Workup

customevaporated to dryness
dissolutionThe residue is dissolved in 5 mL of DMF
stirringThe mixture is stirred overnight at room temperature
customThe reaction is quenched with 20 mL water
extractionextracted with EtOAc (3×30 mL)
washwashed with water and brine
dry with materialdried over Na2SO4
concentrationConcentration and purification via silica gel chromatography

Sources & evidence

ORD record: ord-054e8bcd35ce4e4189b88dea0efdd0e0
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07169775B2

Reaction notes

Loading…