Acetic Acid → N1-(benzo[d]isothiazol-3-yl)-N3-((4'-methoxybiphenyl-4-yl)methyl)propane-1,3-diamine

N1-(Benzo[d]isothiazol-3-yl)propane-1,3-diamine (600 mg, 2.8 mmol) and 4′-methoxy-biphenyl-4-carboxaldehyde (614 mg, 2.8 mmol) were combined in 1,2-dichloroethane (20 mL) and treated with sodium triacetoxyborohydride (1.2 g, 5.7 mmol) and acetic acid (160 μL, 5.6 mmol). The mixture was stirred at room temperature overnight. The reaction was quenched by addition of saturated aqueous sodium bicarbonate solution. The crude product was extracted with ethyl acetate (2×50 mL). The organic extract was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography, on silica gel, eluting with 98:2 methylene chloride: methanol to yield N1-(benzo[d]isothiazol-3-yl)-N3-((4′-methoxybiphenyl-4-yl)methyl)propane-1,3-diamine (330 mg) as a light yellow foam. 1H NMR (CDCl3): 7.80 (d, 1H), 7.75 (d, 1H), 7.25-7.45 (m, 8H), 6.90 (d, 2H), 3.95 (s, 2H), 3.85 (s, 3H), 3.70 (t, 2H), 3.00 (t, 2H), 2.30-2.40 ppm (m, 2H).

1. customThe reaction was quenched by addition of saturated aqueous sodium bicarbonate solution
2. extractionThe crude product was extracted with ethyl acetate (2×50 mL)
3. extractionThe organic extract
4. dry with materialwas dried over anhydrous sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe resulting residue was purified by column chromatography, on silica gel
8. washeluting with 98:2 methylene chloride

ORD 기록

ord-0b03cffb4a1c4688b2a28eae2f6c1950

출처 데이터셋

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07776847B2