3-Pyridinemethanamine → 4-[4-(Hydroxymethyl)-5-methyl-1,3-oxazol-2-yl]-N-(3-pyridinylmethyl)benzamide

Temperature

20 °C

HBTU (170 mg, 0.45 mmol) was added to a solution of acid 55 (80 mg, 0.34 mmol) and diisopropylethylamine (0.13 mL, 0.69 mmol) in anhydrous DMF (7 mL). The solution was stirred at 20° C. for 10 min. 3-Pyridinylmethanamine (0.14 mL, 1.4 mmol) was then added and the reaction mixture was stirred at 20° C. for 1 h. It was the diluted with DCM (300 mL) and washed with H2O (3×50 mL) and then washed with brine (50 mL). The combined organic phase was dried, filtered and the solvent evaporated. The residue was purified by column chromatography, eluting with 10% MeOH/DCM, to give amide 56 (65 mg, 59%) as a cream powder: mp (MeOH/DCM) 182-184° C.; 1H NMR δ 9.19 (t, J=5.7Hz, 1 H, NH), 8.57 (br s, 1 H, H-2′), 8.46 (br d, J=4.6Hz, 1 H, H-6′), 8.00 (s, 4 H, H-2, H-3, H-5, H-6), 7.74 (br d, J=7.8Hz, 1 H, H-4′), 7.36 (dd, J=7.8, 4.8Hz, 1 H, H-5′), 5.06 (t, J=5.6Hz, 1 H, OH), 4.51 (d, J=5.8Hz, 2 H, CH2N), 4.39 (d, J=5.6Hz, 2 H, CH2O), 2.41 (s, 3 H, CH3); MS m/z 324.8 (MH+, 100%); Anal. calcd for C18H17N3O3.¼H2O: C, 65.94; H, 5.38; N, 12.82. Found: C, 66.06; H, 5.20; N, 12.85.

1. stirringthe reaction mixture was stirred at 20° C. for 1 h
2. washwashed with H2O (3×50 mL)
3. washwashed with brine (50 mL)
4. customThe combined organic phase was dried
5. filtrationfiltered
6. customthe solvent evaporated
7. customThe residue was purified by column chromatography
8. washeluting with 10% MeOH/DCM

ORD record

ord-5d04ab59c15b49ae9fe1b48c9ca5c7d6

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09085570B2