Cyclopropylamine → HCID 47451248, compound

Participants

Reaction Steps

To a solution of 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol (7.77 g, 57.1 mmol), 2-(tert-butoxycarbonylamino)acetic acid (10 g, 57.1 mmol), cyclopropanamine (3.91 g, 68.5 mmol) and DMAP (8.37 g, 68.5 mmol) in DMF (28 mL) was added N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrogen chloride salt and the mixture stirred at room temperature for 16 h. The mixture was diluted with ethyl acetate, washed with 0.1N aqueous HCl, aqueous NaHCO3 and brine, dried over MgSO4, filtered and concentrated in vacuo to give tert-butyl 2-(cyclopropylamino)-2-oxoethylcarbamate (8.90 g, 41.5 mmol, 72.8%) as a pale yellow oil: 1H NMR (400 MHz, CDCl3) δ 6.18 (s, 1H), 3.74 (d, J=5.9 Hz, 2H), 2.71 (m, 1H), 1.45 (s, 9H); 0.84-0.7 (m, 2H), 0.56-0.43 (m, 2H); EIMS m/z 214 ([M]+). To a solution of tert-butyl 2-(cyclopropylamino)-2-oxoethylcarbamate (8.5 g, 39.7 mmol) in dioxane (20 mL) was added HCl (100 mmol, 25 mL 4 M in dioxane) and the mixture stirred at 10° C. for 3 h. The mixture was diluted with hexanes and filtered under vacuum to give 2-amino-N-cyclopropylacetamide, HCl salt as a white solid (5.2 g, 83%): mp 139-142° C.; 1H NMR (400 MHz, DMSO-d6) δ 8.66 (bs, 1H), 8.19 (bs, 3H), 3.46 (s, 2H), 2.73-2.60 (m, 1H), 0.71-0.60 (m, 2H), 0.48-0.36 (m, 2H).

Provenance & Evidence