Sodium borohydride → HCID 71666214, compound

Participants

Reaction Steps

The compound of this example is prepared as described in Example 13 above except that the acetyl group of tert-butyl 4-(2-(3-acetyl-5-(2-((tert-butoxycarbonyl)amino)-acetamido)phenyl)-5-oxo-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-yl)piperazine-1-carboxylate is further reduced to tert-butyl 4-(2-(3-(2-((tert-butoxycarbonyl)amino)acetamido)-5-(1-hydroxyethyl)phenyl)-5-oxo-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-yl)piperazine-1-carboxylate using sodium borohydride. The resulting product is then deprotected as described in Step 6 of Example 1. 1H NMR (400 MHz, DMSO-d6) δ 10.73 (s, 1H), 8.95-8.80 (br.s., 2H), 8.16 (t, J=1.8 Hz, 1H), 8.16-8.07 (br.s., 2H), 7.76 (t, J=1.8 Hz, 1H), 7.59 (s, J=1.8 Hz, 1H), 5.61 (s, 1H), 5.50-5.45 (br.s., 1H), 4.83 (q, J=6.7 Hz, 1H), 3.81 (s, 2H), 3.78 (t, J=5.2 Hz, 4H), 3.19 (t, J=5.2 Hz, 4H), 1.36 (d, J=6.7 Hz, 3H); LC/MS: tR=2.417 min; HRMS: m/z (M+H+)=(Calculated for C19H24N7O3S=430.1661).

Provenance & Evidence