4-(4-Bromobenzyl)morpholine → 4-(Morpholinomethyl)aniline

Participants

Reaction Steps

[5-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(4-morpholin-4-ylmethyl-phenyl)-amine was prepared from 5-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (125 mg, 0.43 mmol) and 4-(4-bromobenzyl)morpholine (122 mg, 0.48 mmol) in a manner analogous to Example 77 to yield 5-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(4-morpholin-4-ylmethyl-phenyl)-amine (73 mg, 37%) as an off-white powder following purification on a 4 g Isco silica gel column using methanol in dichloromethane (0-20%) as eluent. MP=222-223° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.66 (s, 1H), 8.32 (d, J=7.50 Hz, 2H), 8.15 (d, J=7.50 Hz, 2H), 7.66 (m, 4H), 7.30 (d, J=6.42 Hz, 1H), 7.20 (d, J=8.60 Hz, 2H), 3.55 (br s, 4H), 3.40-3.32 (m, 5H), 2.32 (br s, 4H). MS=465 (MH)+.

Provenance & Evidence