Sodium Bicarbonate → 1-(2,4-dimethoxyphenyl)-N-(1,2,3-thiadiazol-4-ylmethyl)methanamine

To a solution of 1,2,3-thiadiazole-4-carboxaldehyde (750 mg, 6.57 mmol) and 2,4-dimethoxybenzylamine (1086 μl, 7.23 mmol) in 1,2-dichloroethane (13.1 mL) at 0° C. was added molecular sieves (powdered, 4 A) (2.50 g, 6.57 mmol) followed by sodium triacetoxyborohydride (1950 mg, 9.20 mmol). The reaction was allowed to warm to room temperature with stirring overnight. Then, the resulting suspension was poured into dichloromethane (75 mL) and aqueous sodium hydrogen carbonate (saturated, 75 mL). The layers were mixed and then filtered through celite. The aqueous layer was then extracted with dichloromethane (3×50 mL) and the combined organics were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (EtOAc/Hexanes+1% triethylamine gradient) to afford the title compound as a pale yellow liquid. LRMS (APCI) calculated for C12H16N3O2S [M+H]+, 266.1. found 266.1.

1. additionThe layers were mixed
2. filtrationfiltered through celite
3. extractionThe aqueous layer was then extracted with dichloromethane (3×50 mL)
4. dry with materialthe combined organics were dried over anhydrous Na2SO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by column chromatography on silica gel (EtOAc/Hexanes+1% triethylamine gradient)

ORD record

ord-9a3e1fb2fae24b2988e5185aa1fb1d63

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08222269B2