(2-Methoxyethyl)(methyl)amine → (3-(4-(((2-Methoxyethyl)(methyl)amino)methyl)phenylthio)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanone hydrochloride

Participants

Reaction Steps

Using a similar protocol as described in Example 60 employing 60B (0.16 g, 0.41 mmol) and 2-methoxy-N-methylethanamine (0.037 g, 0.41 mmol) as starting materials afforded the desired compound in neutral form as a gum. The residue was then dissolved in MeOH (2 ml) whereupon HCl in MeOH (1.25 M, 2 ml) was added. After a little while, it was evaporated to dryness. The residue was triturated with MeOH/diethyl ether. There was obtained 0.16 g (80%) of 61 as a solid. 1H NMR (500 MHz, DMSO-d6): δ 2.64 (s, 3H), 3.15 (m, 1H), 3.23 (m, 1H), 3.27 (s, 3H), 3.73 (m, 2H), 3.98 (m, 1H), 4.25 (dd, 1H), 4.34 (dd, 1H), 4.47 (m, 2H), 4.68 (m, 1H), 5.15 (m, 1H), 7.35 (d, 2H), 7.5-7.7 (m, 5H), 8.04 (d, 2H), 11.0 (m, 1H), MS (APCI+) m/z 439 [M+H]+, LC purity: 88%.

Provenance & Evidence