Benzyl 4-(4-carbamoylbenzo[d]oxazol-2-yl)benzyl(methyl)carbamate → 2-(4-((Methylamino)methyl)phenyl)benzo[d]oxazole-4-carboxamide

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Reaction Steps

Benzyl 4-(4-carbamoylbenzo[d]oxazol-2-yl)benzyl(methyl)carbamate (0.050 g, 0.12 mmol) was dissolved in THF (10 mL) and 10% Pd/C (5.0 mg) was added, Hydrogen was purged into the mixture, and the mixture was maintained at room temperature for 6 hr, then the Pd/C was filtered off and the filtrate was condensed to get 2-(4-((methylamino)methyl)phenyl)benzo[d]oxazole-4-carboxamide (0.0212 g, 69.6% yield). 1H-NMR (400 MHz, DMSO-d6) δ 2.59 (s, 3H), 4.24-4.26 (t, J=5.0 Hz, 1H), 7.56-7.60 (t, J=8.0 Hz, 1H), 7.80-7.82 (d, J=8.0 Hz, 2H), 8.00-8.07 (m, 3H), 8.38-8.40 (d, J=8.0 Hz, 2H), 8.49 (s, 1H), 9.39 (s, 2H); LC-MS (ESI) m/z 282 [M+1]+.

Provenance & Evidence