4-Methylmorpholine → HCID 16718838, compound

Participants

Reaction Steps

A solution of 2-(4-(6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl)-2-methoxyphenoxy)acetic acid Example 15 (20 mg; 0.045 mmol), piperidine (7 uL; 0.068 mmol), EDC hydrochloride (10 mg; 0.054 mmol) and hydroxybenzotriazole hydrate (8 mg; 0.054 mmol) in 70 uL of DMF and 415 uL of CH2Cl2 was cooled to 0° C. After addition of N-methylmorpholine (6 uL; 0.054 mmol), the solution allowed to warm to rt and stir for 23 h. Following concentration under reduced pressure and dilution with water, the mixture was extracted with EtOAc. The organic layer was washed with water and brine, dried over MgSO4, filtered and the filtrate concentrated under reduced pressure. The residue was triturated in MeOH to afford the title compound (20 mg; 87%) as a white solid. 1H NMR (CDCl3) δ 1.57-1.67 (m, 6H), 3.52-3.59 (m, 4H), 3.90 (s, 3H), 4.81 (s, 2H), 6.91 (dd, J=8.25 Hz, 2.20 Hz, 1H), 6.98 (d, J=2.75 Hz, 1H), 7.09 (d, J=8.25 Hz, 1H), 7.44 (d, J=8.79 Hz, 2H), 7.53 (s, 1H), 7.66 (d, J=8.80 Hz, 2H), 8.13 (s, 1H); 13C NMR (CDCl3) δ 24.42, 25.54, 26.47, 43.27, 46.39, 56.15, 68.65, 111.13, 113.98, 119.14, 120.86, 123.21, 127.65, 129.45, 130.75, 131.54, 135.68, 148.14, 148.28, 149.88, 151.66, 156.75, 157.40, 165.65; HPLC (Method #1): 3.65 min retention time; MS (ES): m/z 510 [M+H]+.

Provenance & Evidence