تفاعل #2364598

ord-1661679caa5c46de99a31372b2624242

معادلة التفاعل

CCOC(=O)c1nc(NC(=O)Nc2ccc(OC(F)(F)F)cc2)cn1C
1-methyl-4-[({[4-(trifluoromethoxy)phenyl]-amino}carbonyl)amino]-1H-imidazole-2-carboxylic acid ethyl ester
CCOC(=O)c1nc(NC(=O)Nc2ccc(OC(F)(F)F)cc2)cn1C
1-Methyl-4-[({[4-(trifluoromethoxy)phenyl]amino}carbonyl)amino]-1H-imidazole-2-carboxylic acid ethyl ester
[Na+].[OH-]
sodium hydroxide
Cl
hydrochloric acid
Cn1cc(NC(=O)Nc2ccc(OC(F)(F)F)cc2)nc1C(=O)O
1-Methyl-4-[({[4-(trifluoromethoxy)phenyl]amino}carbonyl)amino]-1H-imidazole-2-carboxylic acid

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    workup.ADDITIONis added
  2. 2
    درجة الحرارةwhile being cooled with ice
  3. 3
    استخلاصThe solution is extracted with dichloromethane
  4. 4
    تركيزThe organic phase is concentrated by evaporation in a vacuum
  5. 5
    أخرىThe residue is purified by preparative HPLC

الإجراء التجريبي

835 mg (2.13 mmol) of 1-methyl-4-[({[4-(trifluoromethoxy)phenyl]-amino}carbonyl)amino]-1H-imidazole-2-carboxylic acid ethyl ester (Example 3A) is suspended in 5 ml of ethanol and 12 ml of tetrahydrofuran. While being cooled with ice, 2 ml (25 mmol) of 50% aqueous sodium hydroxide solution is added. The reaction mixture is stirred overnight at room temperature and then made acidic with 1N hydrochloric acid while being cooled with ice. The solution is extracted with dichloromethane. The organic phase is concentrated by evaporation in a vacuum. The residue is purified by preparative HPLC.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US09133165B2uspto-grants-2015_09