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. 2016 May 11;21(5):615. doi: 10.3390/molecules21050615

Scheme 5.

Scheme 5

Synthetic scheme for generating the DDAH-1 biochemical probe N-but-3-ynyl-2-chloro-acetamidine (18). Reagents and Conditions: (i) DCM, TEA, DMAP, MsCl, 0 °C for 2 h then 25 °C for 3 h, 62%; (ii) anhydrous DMF, NaN3, 70 °C, 3.5 h; (iii) Et2O, Ph3P, 0 °C for 2 h, addition of H2O, then 25 °C for 20 h, 49% (two steps); (iv) dry HCl(g) at 0 °C for 1 h, stop HCl(g), then 0 °C for 4 h and RT overnight 48%–76%; (v) H2O, pH = 10, 0 °C for 3 h, 25 °C for 2 h, neutralized, RT for 1.5 days, 62%. Adapted with permission from [109]. Copyright 2009 American Chemical Society.