4-Methylmorpholine → HCID 59380386, compound

Participants

Reaction Steps

3-[4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)[1]benzothieno[2,3-d]pyrimidin-7-yl]propanoic acid (25 mg, 0.05 mmol, 1 equiv), 4-methyl piperazine (6 mg, 0.06 mmol, 1.2 equiv), 1-[3-(dimethylaminopropyl)]-3-ethyl carbodiimide (14.1 mg, 0.07 mmol, 1.5 equiv), 4-methyl morpholine (10 mg, 0.1 mmol, 2 equiv) and 1-hydroxybenzotriazole (14 mg, 0.1 mmol, 2 equiv) were mixed in DMF and stirred at rt for 16 h. Water and EtOAc were added and extraction was preformed 3 times. Organic layers was concentrated and purified by preparative TLC using 5% MeOH/DCM to yield a solid product (18.5 mg, 64%). 1H-NMR (DMSO-d6) δ 8.94 (s, 1H), 8.49 (s, 1H), 8.45 (d, 1H), 7.96 (d, 1H), 7.74 (d, 1H), 7.52 (dd, 1H), 7.45 (m, 2H), 7.30 (m, 2H), 7.23 (d, 1H), 7.16 (m, 1H), 5.26 (s, 2H), 3.41 (m, 4H), 2.99 (t, 2H), 2.72 (t, 2H), 2.20 (m, 4H), 2.13 (s, 3H); LCMS RT=2.87 min, [M+H]+=590.2

Provenance & Evidence