Morpholine → HCID 59380488, compound

Participants

Reaction Steps

To a solution of (4-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}[1]benzothieno[2,3-d]pyrimidin-7-yl)acetic acid (50 mg, 0.10 mmol, 1 eq, from example 94) in DCM (2 mL) were added HOBt (14 mg, 0.10 mmol, 1 equiv) and EDCI (24 mg, 0.13 mmol, 1.2 equiv) under nitrogen. After the mixture was stirred at rt for 5 min, morpholine was added. The resulting reaction mixture was stirred at rt for 15 h. The solvent was concentrated in vacuo. Methanol was added to the residue and a white solid was precipitated out from the solution. The solid was filtered, washed with methanol (2×3 mL) then dried in vacuo to obtain a white solid (27.8 mg, 0.05 mmol, 51%). 1H-NMR (DMSO-d6) δ 9.0 (broad s, 1H), 8.58 (d, J=4.6 Hz, 1H), 8.51 (s, 1H), 8.49 (d, J=8.5 Hz, 1H), 7.94 (s, 1H), 7.87 (t, 1H), 7.76 (d, J=2.2 Hz, 1H), 7.57 (d, J=7.8 Hz, 1H), 7.53 (dd, J=2.6, 8.8 Hz, 1H), 7.45 (d, J=8.5 Hz, 1H), 7.35 (m, 1H), 7.24 (d, J=8.7 Hz, 1H), 5.30 (s, 2H), 3.91 (s, 2H), 3.50 (m, 8H); LCMS RT=2.69 min, [M+H]+=546.20

Provenance & Evidence