Nitrogen → HCID 86636032, compound

Participants

Reaction Steps

In an oven-dried flask filled with N2 was added 3-[(3-chloropyrazin-2-yl)-(4-phenoxyphenyl)-methyl]-carbamoylazetidine-1-carboxylic acid tert-butyl ester (110 mg, 0.00022 mol), MeCN (3 mL, 0.07 mol) and DMF (0.3 mL, 0.004 mol). POCl3 was added dropwise at 0° C. The reaction was warmed up to rt and stirred at that temp overnight. The excess of POCl3 was removed under reduced pressure and the residue was quenched with 2 N NH3 in i-PrOH at 0° C. with vigorous stirring to adjust pH to 9. The crude reaction mixture was then charged with water and the aqueous layer was washed with DCM. The combined organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by prep TLC using 3% NH3 in MeOH in DCM afforded 45 mg of the title compound as a yellow oil. The compound was carried on to the next step. MS (ES+): m/z 477.02 (100)[MH+]. HPLC: tR=4.17 min (Open Lynx, polar—5 min).

Provenance & Evidence