1,8-Diazabicyclo(5.4.0)undec-7-ene → N-{[2-(2,6-Dioxo(3-piperidyl))-1,3-dioxoisoindolin-4-yl]methyl}-3,3-dimethylbutanamide

1,8-Diazabicyclo[5,4,0]undec-7-ene (0.62 g, 4 mmol) was added to a stirred suspension of 4-(aminomethyl)-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione hydrochloride (0.6 g, 1.9 mmol) in acetonitrile (50 ml). After stirring for 20 min, t-butylacetyl chloride (0.25 g, 1.9 mmol) was added. The mixture was stirred at room temperature for 17 hours. Solvent was removed in vacuo and the residue was dissolved in dichloromethane (90 ml) and washed with 0.1N HCl (30 ml), water (30 ml), brine (30 ml) and then dried. Solvent was removed in vacuo and the solid residue was slurried in ethanol (10 ml) to give after filtration 0.55 g (77%) of the product: mp 145–147° C.; 1H NMR (DMSO-d6) δ 11.14 (s, 1H), 8.39 (t, J=5.7 Hz, 1H), 7.87–7.69 (m, 3H), 5.19–5.12 (dd, J=5.3 and 12.4 Hz, 1H), 4.72 (d, J=5.8 Hz, 2H), 2.92–2.83 (m, 1H), 2.63–2.51 (m, 2H), 2.08 (s, 2H), 2.08–2.04 (m, 1H), 0.97 (s, 9H); 13C NMR (DMSO-d6) δ 172.69, 171.35, 169.74, 167.51, 166.96, 139.61, 134.69, 133.41, 131.52, 127.11, 121.87, 48.86, 48.62, 37.53, 30.93, 30.52, 29.71, 22.00; Anal. Calcd. For C20H23N3O5+0.28 water: C, 61.52; H, 6.08; N, 10.76. Found: C, 61.23; H, 6.18; N, 10.57.

1. stirringThe mixture was stirred at room temperature for 17 hours
2. customSolvent was removed in vacuo
3. dissolutionthe residue was dissolved in dichloromethane (90 ml)
4. washwashed with 0.1N HCl (30 ml), water (30 ml), brine (30 ml)
5. customdried
6. customSolvent was removed in vacuo
7. customto give
8. filtrationafter filtration 0.55 g (77%) of the product

ORD 기록

ord-d6c052b5e4264548a1573f008ef022f3

출처 데이터셋

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07091353B2