A common compound: 25808-30-4, name is 2-(Methylamino)acetonitrile hydrochloride, belongs to nitriles-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 25808-30-4
tert-butyl (4-chloro-2-formylphenyl)carbamate (3.00 g, 11.7 mmol, 1 eq.), 2-(methylamino)-acetonitrile hydrochloride (3.74 g, 35.1 mmol, 3 eq.), and DIPEA (6.16 g, 35.1 mmol, 3 eq.) were mixed in DCE (76 mL) and stirred for 15 min at 25 C. Acetic acid (2.1 mL, 35.1 mmol, 3 eq.)) and MgSO4 (4.32 g, 35.1 mmol, 3 eq.) were added, and the suspension was stirred for 2 h at 60 C. After the reaction mixture was cooled to 25 C, sodium triacetoxyborohydride (6.21 g, 29.3 mmol, 2.5 eq.) was added in two portions, and the reaction was stirred for 18 h at 25 C. The reaction was quenched with methanol and sodium bicarbonate (sat. aq.) to pH 8, and the aqueous layer was extracted with ethyl acetate twice. The organic layers were combined, dried over MgSO4, and evaporated under reduced pressure. The residue was purified by column chromatography (SiO2, 0-30percent EtOAc/Hex) to give tert-butyl (4-chloro-2- (((cyanomethyl)(methyl)amino)methyl)phenyl)carbamate (1.33 g, 37percent yield) as a white solid. LCMS (ESI): m/z 310 (M+H); Retention time: 3.36 min (50-100 percent ACN/H2O, method 3).
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 25808-30-4, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; BLACKTHORN THERAPEUTICS, INC.; JONES, Robert, M.; URBANO, Mariangela; BRANDT, Gary; HARDICK, David; KNIGHT, Chris; (337 pag.)WO2018/226769; (2018); A1;,
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Nitriles – Chemistry LibreTexts