Dimethylformamide → HCID 58958459, compound

Participants

Reaction Steps

N-Cyclopropyl-2-[(trimethylsilyl)amino]-1,3-thiazole-5-carboxamide 23-5 (0.26 g, 1.0 mmol) was treated with 2 mL of phosgene (as a 20% solution in toluene) and 1 mL of methylene chloride at room temperature for 4 hours. The suspension was concentrated to dryness and the residue was treated with a suspension of DIEA (0.16 g, 1.2 mmol) and 4-boc-amino-1-piperidine 23-6 (0.20 g, 1.0 mmol) in 1 mL of dry DMF and 1 mL of methylene chloride overnight at room temperature. The intermediate product was purified on C18 column and the residue treated with TFA. The crude product was purified on a C18 preparative HPLC column and isolated via lyophilization to afford the final product 23-7. Hi-Res MS: calc: 310.1332 found: 310.1334. 1H-NMR (DMSO): 8.33 ppm (s, 1H); 7.92 ppm (s, 1H); 7.84 ppm (m, 3H); 3.27 ppm (m, 1H); 2.91 ppm (t, 2H); 2.75 ppm (m, 1H); 1.90 ppm (d, 2H); 1.40 ppm (q, 2H); 0.67 ppm (m, 2H); 0.52 ppm (m, 2H).

Provenance & Evidence