Réaction #89835

Équation de réaction

chloride

Et3N

tert-butyl 5-(2-(3-aminophenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate

morpholine-4-carbonyl chloride

morpholine-4-carbonyl chloride

Et3N

Et3N

→

tert-butyl 5-(2-(3-(morpholine-4-carboxamido)phenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate

Solvants

CH2Cl2

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwere added
2. 2
   workup.ADDITIONwere added
3. 3
   ConcentrationThe reaction was concentrated in vacuo
4. 4
   Autrethe residue was purified by flash chromatography on silica (12:1 CH2Cl2:MeOH)

Mode opératoire

To a suspension of tert-butyl 5-(2-(3-aminophenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate (100 mg, 0.22 mmol) and morpholine-4-carbonyl chloride (51 μL, 0.44 mmol,) in CH2Cl2 (2 mL) was added Et3N (61 μL, 0.44 mmol) and catalytic amount of DMAP. The reaction mixture was stirred at RT for 2 h after which 2 equivalents each of morpholine-4-carbonyl chloride and Et3N were added. After 2 h of stirring another 2 equivalents of both the chloride and Et3N were added and continued to stir at ambient temperature for 16 hours. The reaction was concentrated in vacuo and the residue was purified by flash chromatography on silica (12:1 CH2Cl2:MeOH). The product tert-butyl 5-(2-(3-(morpholine-4-carboxamido)phenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate was isolated. (80 mg, 65%)

Source