Triethylamine → HCID 54705117, compound

Participants

Reaction Steps

N-((4-fluoro-2-(3-(hydroxymethyl)-1H-1,2,4-triazol-1-yl)phenyl)methyl)-3′-hydroxy-4′-oxo-2,3,5,6,6′,7′-hexahydro-4′H-spiro[pyran-4,10′-pyrimido[1,2-d][1,4]oxazepine]-2′-carboxamide (190 mg, 0.32 mmol) was dissolved in 3 mL CH2Cl2 under N2 and treated with 100 mg triethylamine followed by mesylchloride (46 mg, 0.4 mmol) in 0.5 mL CH2Cl2. This was stirred for 30 min and then washed with dilute HCl. The crude product was purified by column chromatography on silica, eluted with EtOAc to give 170 mg of a clear gum. This was dissolved in 30 mL MeOH and heated at 70° C. in a sealed flask for 18 hrs and then concentrated. The residue was stirred with 5 mL TFA for 30 min and concentrated. The residue gave 45 mg of white crystals from 95%-EtOH. (Yield=34%) 1H NMR (500 MHz, CHLOROFORM-D) δ ppm 3.50 (s, 3H) 3.55-4.13 (m, 14H) 4.50 (d, J=5.80 Hz, 2H) 4.63 (s, 2H) 7.06-7.28 (m, 2H) 7.69 (dd, J=8.55, 5.80 Hz, 1H) 8.36 (t, J=6.87 Hz, 1H) 8.40 (s, 1H) 12.10 (s, 1H); HRMS (M+H) calcd for C24H27FN6O6: 515.2054; found: 515.2032.

Provenance & Evidence