Diisopropylethylamine → N-[2-[4-(4,5-Dihydro-1H-imidazol-2-yl)-phenyl]-ethyl]-2-[2-[(6-methoxy-naphthalen-2-yl)sulfonyl]-1,2,3,4-tetrahydro-pyrrolo[1,2-a]pyrazin-1-yl]-acetamide

HATU (563 mg, 1.48 mmol, 2.0 eq.) was added to a mixture of 2-(2-(6-methoxynaphthalen-2-ylsulfonyl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-1-yl)acetic acid (S-2) (297 mg, 0.74 mmol, 1.0 eq.), 2-(4-(4,5-Dihydro-1H-imidazol-2-yl)phenyl)ethanamine (A49) (140 mg, 0.74 mmol, 1.0 eq.), and DIPEA (0.39 ml, 2.22 mmol, 3.0 eq.) in THF (10 ml) at 0° C. and the resulting reaction mixture was stirred at RT for 14 h. The solvent was evaporated under reduced pressure, the residue dissolved in DCM (30 ml) and washed with saturated ammonium chloride solution (15 ml), saturated sodium bicarbonate solution (15 ml), water (15 ml) and brine (15 ml). The organic layer was dried over Na2SO4 and concentrated under reduced pressure to yield the crude product which was purified by column chromatography (neutral alumina; 1% MeOH/DCM) to afford the desired product as an off-white solid. Yield: 35% (140 mg, 0.245 mmol); MS, Rt=3.3 min; m/z=572.5 [MH]+

1. customthe resulting reaction mixture
2. customThe solvent was evaporated under reduced pressure
3. dissolutionthe residue dissolved in DCM (30 ml)
4. washwashed with saturated ammonium chloride solution (15 ml), saturated sodium bicarbonate solution (15 ml), water (15 ml) and brine (15 ml)
5. dry with materialThe organic layer was dried over Na2SO4
6. concentrationconcentrated under reduced pressure
7. customto yield the crude product which
8. customwas purified by column chromatography (neutral alumina; 1% MeOH/DCM)

ORDレコード

ord-e8eccae2e9cd4287885d2bcd44781204

出典データセット

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08158628B2