Diisopropylethylamine → N-(3 hydroxyadamant-1-yl)-2,5-dimethyl-1-phenyl-1H-imidazole-4-carboxamide

To a magnetically stirred solution of 2,5-dimethyl-1-phenyl-1H-imidazole-4-carboxylic acid (0.66 gram, 0.00306 mol) in dichloromethane (35 ml) was successively added diisopropylethylamine (DIPEA) (3.1 ml), CIP (2-chloro-1,3-dimethylimidazolinium hexafluorophosphate). (2.55 gram) and 3-hydroxyadamantane amine (0.612 gram, 0.00366 mol). The resulting mixture was reacted at 20° C. for 16 hours and subsequently concentrated in vacuo. The resulting residue was taken up in dichloromethane and washed with 5% aqueous NaHCO3 solution. The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The resulting residue was purified by flash chromatography (dichoromethane/methanol=98/2 (v/v)) to give N-(3 hydroxyadamant-1-yl)-2,5-dimethyl-1-phenyl-1H-imidazole-4-carboxamide (0.75 gram, 67% yield). Rf (silica gel/dichoromethane/methanol=98/2 (v/v))˜0.6. Melting point: 215-220° C.

1. customThe resulting mixture was reacted at 20° C. for 16 hours
2. concentrationsubsequently concentrated in vacuo
3. washwashed with 5% aqueous NaHCO3 solution
4. dry with materialThe organic layer was dried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe resulting residue was purified by flash chromatography (dichoromethane/methanol=98/2 (v/v))

ORD 기록

ord-1393384b68b146fdafa96a648774b271

출처 데이터셋

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08937184B2