Réaction #308850

Équation de réaction

[5-(3-Amino-phenyl)-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-carbamic acid tert-butyl ester

furan-2-carboxylic acid

HOBT

DIPEA

EDC

→

title compound

(5-{3-[(Furan-2-carbonyl)-amino]-phenyl}-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-yl)-carbamic acid tert-butyl ester

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   Températureto warm to room temperature
2. 2
   workup.STIRRINGstirred for 17 h at room temperature
3. 3
   Autrequenched with 1M aqueous KHCO3 solution
4. 4
   Extractionextracted with dichloromethane
5. 5
   LavageThe organic phase was washed with water and brine
6. 6
   Séchagedried with Na2SO4
7. 7
   Concentrationconcentrated under reduced pressure
8. 8
   AutreThe residue was purified by chromatography on silica gel (cyclohexane/EtOAc)

Mode opératoire

[5-(3-Amino-phenyl)-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-carbamic acid tert-butyl ester (264 mg, 0.865 mmol), furan-2-carboxylic acid (107 mg, 0.951 mmol) and HOBT (172 mg, 1.124 mmol) were dissolved in dichloromethane under N2 at 0° C. DIPEA (112 mg, 0.865 mmol) and EDC (182 mg, 0.951 mmol) were added. The mixture was stirred at 0° C. for 10 min, then allowed to warm to room temperature, stirred for 17 h at room temperature, quenched with 1M aqueous KHCO3 solution and extracted with dichloromethane. The organic phase was washed with water and brine, dried with Na2SO4 and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (cyclohexane/EtOAc) to yield the title compound in the form of a colourless solid. 1H-NMR (400 MHz, DMSO-d6): 9.86 (br, 1H), 9.27 (br, 1H), 7.83 (d, 1H), 7.69 (m, 2H), 7.30 (m, 2H), 7.15 (dd, 1H), 6.65 (m, 1H), 4.40-4.30 (m, 2H), 3.75-3.55 (m, 2H), 1.52 (s, 3H), 1.44 (s, 9H); MS: 400 [(M+H)+].

Source