Methylamine → 4-[2-(4-bromophenyl)-1-(4-methoxyphenyl)ethyl]-1-methyl-1H-imidazol-2-amine

HRID 452559

Reaction equation

Br[CH2:2][C:3](=O)[CH:4]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][CH:7]=1.[CH3:22][NH2:23].Br.C(S[C:28](=[NH:30])[NH2:29])C.[OH-].[Na+]>CO>[Br:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH:4]([C:3]2[N:30]=[C:28]([NH2:29])[N:23]([CH3:22])[CH:2]=2)[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 25 °C

Procedure

1-bromo-4-(4-bromophenyl)-3-(4-methoxyphenyl)butan-2-one (0.15 g, 0.36 mmol) was dissolved in methanol (1.8 mL) and methylamine (0.36 mL, 0.72 mmol, 2M solution in methanol) was added in one portion and the reaction was allowed to stir at 25° C. for 0.5 hour. S-ethylisothiourea hydrobromide (0.27 mg, 1.46 mmol) and NaOH (0.61 mL, 1.82 mmol, 3M solution in water) were added to the solution and the resulting solution was allowed to stir at 25° C. for 16 hours. The reaction was purified using reverse phase C-18 chromatography (acetontitrile and water system) to afford 140 mg of 4-[2-(4-bromophenyl)-1-(4-methoxyphenyl)ethyl]-1-methyl-1H-imidazol-2-amine as a yellow solid.

Workup

stirringto stir at 25° C. for 16 hours
customThe reaction was purified

Sources & evidence

ORD record: ord-af88c8423c9e4317bb520879787aed68
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492387B2

Linked notes

Loading…