반응 #168742

반응 방정식

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

5-bromo-pyrimidine-2-carboxylic acid

HOBT

DIPEA

EDC

→

title compound

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

용매

dichloromethane

반응 조건

후처리

1. 1
   온도to warm to room temperature
2. 2
   workup.STIRRINGstirred for 17 h at room temperature
3. 3
   기타quenched with 1M aqueous KHCO3 solution
4. 4
   추출extracted with dichloromethane
5. 5
   세척The organic phase was washed with water and brine
6. 6
   건조dried over Na2SO4
7. 7
   농축concentrated under reduced pressure
8. 8
   기타The residue was purified by automated column chromatography (cyclohexane/ethyl acetate)

실험 절차

[(R)-5-(3-Amino-5-bromo-phenyl)-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-carbamic acid tert-butyl ester (33 mg, 0.082 mmol), 5-bromo-pyrimidine-2-carboxylic acid (18 mg, 0.090 mmol) and HOBT (16 mg, 0.106 mmol) were dissolved in dichloromethane under N2 at 0° C. DIPEA (10.54 mg, 0.082 mmol) and EDC (17 mg, 0.090 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 over Na2SO4 and concentrated under reduced pressure. The residue was purified by automated column chromatography (cyclohexane/ethyl acetate) to yield the title compound as a tan foam. MS: 569 [(M+H)+].

출처