Ammonia → HCID 68521339, compound

Participants

Reaction Steps

Prepared according to the method described in example R-13 with the exception that step c was performed as follows: To a solution of 5-(4-(4-(tert-butoxycarbonyl)piperazin-1-yl)phenyl)-2-(pyridin-3-ylamino)oxazole-4-carboxylic acid (0.046 g, 0.1 mmol) in DMF (1 ml) was added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.065 g, 0.17 mmol), diisopropylethylamine (0.03 m, 0.17 mmol) and 0.5M NH3 in dioxane (0.6 m, 0.3 mmol) and the resultant mixture stirred at room temperature overnight. A further portion of O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.020 g, 0.05 mmol), diisopropylethylamine (0.01 m, 0.056 mmol) and 0.5M NH3 in dioxane (0.2 m, 0.1 mmol) was added and the reaction stirred for 1 hour. The solvent was removed in vacuo and the residue purified by preparative HPLC to afford tert-butyl 4-(4-(4-carbamoyl-2-(pyridin-3-ylamino)oxazol-5-yl)phenyl)piperazine-1-carboxylate (0.006 g, 0.013 mmol, 13%). LCMS (2) Rt: 2.64 min; m/z (ES+) 465. 1H NMR (DMSO) δ 2.84 (4H, t), 3.16 (4H, t), 6.99 (2H, d), 7.35 (1H, dd), 7.44 (1H, br s), 7.66 (1H, br s), 8.07 (2H, d), 8.19 (1H, dd), 8.35 (1H, dd), 8.77 (1H, d), 10.60 (1H, br s). LCMS (2) Rt: 1.62 min; m/z (ES+) 365.

Provenance & Evidence