3,4-Diaminopyridine → (S)-tert-butyl 2-(biphenyl-4-yl)-1-(3H-imidazo[4,5-c]pyridin-2-yl)ethylcarbamate

To a solution of (S)-3-(biphenyl-4-yl)-2-(tert-butoxycarbonylamino)propanoic acid (400 mg, 1.172 mmol) in DMF (5 mL) were added BOP (580 mg, 1.289 mmol) and DIPEA (0.246 mL, 1.406 mmol) at room temperature. After being stirred for 10 minutes, pyridine-3,4-diamine (130 mg, 1.230 mmol) was added and stirred for 1 hour. The reaction mixture was diluted with EtOAc and washed with H2O and brine. The organic layer was dried over Na2SO4, concentrated under reduced pressure, and purified by silica gel flash column chromatography (10% MeOH in DCM/DCM). The obtained residue was stirred in acetic acid (5 mL) for 4 hours. The reaction mixture was concentrated and purified by silica gel flash column chromatography to give (S)-tert-butyl 2-(biphenyl-4-yl)-1-(3H-imidazo[4,5-c]pyridin-2-yl)ethylcarbamate; 1H NMR (400 MHz, CDCl3) δ 1.41 (s, 9H), 3.33-3.56 (m, 2H), 5.18-5.27 (m, 1H), 5.37-5.48 (m, 1H), 7.22-7.29 (m, 2H), 7.30-7.36 (m, 1H), 7.42 (t, J=7.83 Hz, 2H), 7.48-7.58 (m, 4H), 7.60-7.66 (m, 1H), 8.32 (d, J=5.81 Hz, 1H), 8.94 (s, 1H); MS: m/z (MH+) 415.

1. stirringstirred for 1 hour
2. washwashed with H2O and brine
3. dry with materialThe organic layer was dried over Na2SO4
4. concentrationconcentrated under reduced pressure
5. custompurified by silica gel flash column chromatography (10% MeOH in DCM/DCM)
6. stirringThe obtained residue was stirred in acetic acid (5 mL) for 4 hours
7. concentrationThe reaction mixture was concentrated
8. custompurified by silica gel flash column chromatography

ORD 기록

ord-953106d223ec441084912d376cf38299

출처 데이터셋

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08877815B2