تفاعل #1156166

معادلة التفاعل

Isobutyl chloroformate

N-methylmorpholine

4-[bis-(2-methoxy-ethyl)-amino]-but-2-ynoic acid

N-(3-bromophenyl)-4,6-quinazolindiamine

→

4-[Bis-(2-methoxy-ethyl)-amino]-but-2-ynoic acid [4-(3-bromo-phenylamino)-quinazolin-6-yl]-amide

المردود 27.1%

المذيبات

tetrahydrofuran

pyridine

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe mixture was stirred for 2 hr at 0° C
2. 2
   أخرىThe reaction was then quenched with ice water
3. 3
   workup.ADDITIONpoured into saturated sodium bicarbonate
4. 4
   استخلاصthe product was extracted with ethyl acetate
5. 5
   استخلاصChromatography of the extract on silica gel
6. 6
   غسيلeluting with methanol/ethyl acetate (15:85)

الإجراء التجريبي

Isobutyl chloroformate (0.845 g, 6.2 mmol) and N-methylmorpholine (0.963 g, 9.52 mmol) were added to an ice cold solution of 2.100 g (9.52 mmol) of 4-[bis-(2-methoxy-ethyl)-amino]-but-2-ynoic acid in 50 mL of tetrahydrofuran under nitrogen. After stirring for 30 min, a solution of 1.500 g of N-(3-bromophenyl)-4,6-quinazolindiamine in 10 mL of pyridine was added and the mixture was stirred for 2 hr at 0° C. The reaction was then quenched with ice water, poured into saturated sodium bicarbonate, and the product was extracted with ethyl acetate. Chromatography of the extract on silica gel, eluting with methanol/ethyl acetate (15:85), gave 0.660 g of 4-[Bis-(2-methoxy-ethyl)-amino]-but-2-ynoic acid [4-(3-bromo-phenylamino)-quinazolin-6-yl]-amide: mass spectrum (m/e): M+H 512.

المصدر