Reaction #1143443

Reaction equation

HCl

ethyl 2-(1-((tert-butoxycarbonyl)amino)cyclopropyl)-5-(2-methyl-3-((2,2,2-trifluoroethyl)amino)quinoxalin-5-yl)-1H-pyrrole-3-carboxylate

→

2-(1-aminocyclopropyl)-5-(2-methyl-3-((2,2,2-trifluoroethyl)amino)quinoxalin-5-yl)-1H-pyrrole-3-carboxylic acid hydrochloride

Solvents

1,4-dioxane

dioxane

water

Conditions

Workup

1. 1
   ConcentrationIt was concentrated to dryness
2. 2
   ConcentrationThe reaction mixture was concentrated

Procedure

A mixture of ethyl 2-(1-((tert-butoxycarbonyl)amino)cyclopropyl)-5-(2-methyl-3-((2,2,2-trifluoroethyl)amino)quinoxalin-5-yl)-1H-pyrrole-3-carboxylate (381a, 970 mg, 1.81 mmol) and LiOH monohydrate (381 mg, 9.09 mmol) in dioxane (8.0 mL) and water (4.00 mL) was heated at 110° C. for 5 h. It was concentrated to dryness and the remaining solid was treated with 4.0 M HCl solution in 1,4-dioxane (11.36 mL, 45.5 mmol) at RT and stirred for 30 min. The reaction mixture was concentrated to give 2-(1-aminocyclopropyl)-5-(2-methyl-3-((2,2,2-trifluoroethyl)amino)quinoxalin-5-yl)-1H-pyrrole-3-carboxylic acid hydrochloride (381b) as a red-orange solid. It was used in the subsequent step without further purification assuming quantitative yield. m/z (ESI, +ve ion) 406.1 (M−35)+.

Source