Benzaldehyde → 2-[1-(1-Benzylpiperidin-3-yl)-ethylamino]-4-[benzimidazol-1-yl]pyrimidine

To a solution of 2-[1-(piperidin-3-yl)-ethylamino]-4-[benzimidazol-1-yl]pyrimidine (EXAMPLE 18) (19.9 mg, 0.062 mmol) in 1,2-dichloroethane (0.5 mL) was added benzaldehyde (6.3 μL, 0.062 mmol) and stirred for 10 min at room temperature. This was followed by the addition of sodium triacetoxyborohydride (18.4 mg, 0.087 mmol) and the reaction mixture was stirred for 3 h. The reaction mixture was quenched with saturated aqueous NaHCO3 and was extracted with EtOAc (3×5 mL). The combined extracts were washed with brine and dried over Na2SO4. The crude product was purified by preparative thin layer chromatography eluting with 1:9 MeOH:CH2Cl2 to obtain 17.9 mg of the title compound. Partial 1H NMR (500 MHz, CDCl3): δ 8.61 (s, 1H); 8.35 (br s, 1H); 8.16 (d, J=7.5 Hz, 1H); 7.86 (d, J=8.9 Hz, 1H); 7.38 (m, 2H); 7.25 (m, 5H); 6.76 (d, J=5.5 Hz, 1H); 4.16 (m, 1H); 3.5 (Abq, JAB=13.2 Hz, 2H); 2.91 (d, J=10.5 Hz, 1H); 2.76 (d, J=11.2 Hz, 1H); 1.23 (d, J=6.6 Hz, 3H). Mass spectrum 413.4 (ESI, M+1).

1. stirringthe reaction mixture was stirred for 3 h
2. customThe reaction mixture was quenched with saturated aqueous NaHCO3
3. extractionwas extracted with EtOAc (3×5 mL)
4. washThe combined extracts were washed with brine
5. dry with materialdried over Na2SO4
6. customThe crude product was purified by preparative thin layer chromatography
7. washeluting with 1:9 MeOH

ORD-Eintrag

ord-9471b74be2f245e1a1a259ffd2f0f6a7

Quelldatensatz

uspto-grants-2001_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06329380B1