1-Hydroxybenzotriazole → 7-(2-Fluoro-4-methylsulfanyl-phenylamino)-pyrrolo[1,2-c]pyrimidine-6-carboxylic acid (2-vinyloxy-ethoxy)-amide

7-(2-Fluoro-4-methylsulfanyl-phenylamino)-pyrrolo[1,2-c]pyrimidine-6-carboxylic acid (200 mg, 0.63 mmol), O-(2-vinyloxy-ethyl)-hydroxylamine (106 mg, 0.69 mmol), HOBt (94 mg, 0.69 mmol), EDCI hydrochloride (132 mg, 0.69 mmol) and DIPEA (118 μL, 0.69 mmol) were dissolved in DMF (5 mL). The reaction was stirred at room temperature for 16 hours then concentrated in vacuo. The resultant residue was dissolved in ethyl acetate (10 mL), washed with aqueous saturated sodium bicarbonate solution (10 mL) and the aqueous fraction extracted twice with ethyl acetate (2×10 mL). The combined organic fractions were washed with brine, dried (MgSO4) and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 0-100% ethylacetate in cyclohexane) to yield the title compound as a brown solid (139 mg, 55%). LCMS (Method B): RT=3.35 min, M+H+=403.

1. concentrationthen concentrated in vacuo
2. dissolutionThe resultant residue was dissolved in ethyl acetate (10 mL)
3. washwashed with aqueous saturated sodium bicarbonate solution (10 mL)
4. extractionthe aqueous fraction extracted twice with ethyl acetate (2×10 mL)
5. washThe combined organic fractions were washed with brine
6. dry with materialdried (MgSO4)
7. concentrationconcentrated in vacuo

ORD 기록

ord-309adfda30f1448ea33ceb67d0dc14f7

출처 데이터셋

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08486963B2