Diisopropylethylamine → 3-{[(5-Chloro-thiophene-2-carbonyl)-amino]-methyl}-[1,2,4]oxadiazole-5-carboxylic acid ethyl ester

To a stirred solution of 3-aminomethyl-[1,2,4]oxadiazole-5-carboxylic acid ethyl ester dihydrochloride (555 mg) at r.t. in DMF (10 ml) under an argon atmosphere were added N-ethyldiisopropylamine (1.82 ml), 5-chloro-2-thiophenecarboxylic acid (565 mg) and BOP (1.54 mg). The mixture was stirred over night, then diluted with EtOAc and washed with H2O. The aqueous phase was back extracted with EtOAc and brine, dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (silica gel; gradient: cyclohexane->cyclohexane/EtOAc 1:1) to give 3-{[(5-chloro-thiophene-2-carbonyl)-amino]-methyl}-[1,2,4]oxadiazole-5-carboxylic acid ethyl ester (586 mg) as off-white solid. MS 316.0 ([M+H]+)

1. washwashed with H2O
2. extractionThe aqueous phase was back extracted with EtOAc and brine
3. dry with materialdried over MgSO4
4. filtrationfiltered
5. concentrationconcentrated
6. customThe crude product was purified by column chromatography (silica gel; gradient: cyclohexane->cyclohexane/EtOAc 1:1)

ORD 기록

ord-ec9db8cc7b674cec8394dbecdebe97ee

출처 데이터셋

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07718679B2