2-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amine → HCID 53358259, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 2-(2,2-dimethylchroman-6-sulfonamido)acetate (40 mg, 0.113 mmol) in acetonitrile (2 mL) was added 3-(bromomethyl)biphenyl (38.9 mg, 0.158 mmol) and resin-supported BEMP (74.5 mg, 0.164 mmol). The mixture was heated in an oil bath at 90° C. overnight. The reaction mixture was filtered, and the filtrate was concentrated to dryness. The crude mixture was taken in DCM (2 mL) and trifluoroacetic acid was added (1 mL). The mixture was stirred at RT for 1 hr and was concentrated to give a off white residue, which was purified by preparative HPLC using MeCN—H2O-0.1% TFA as the solvent to obtain the product as a white powder (25 mg, 45% in two steps). 1H NMR (400 MHz, CDCl3) δ 7.66-7.61 (m, 2H), 7.60 (d, J=1.4 Hz, 1H), 7.59-7.56 (m, 2H), 7.55 (d, J=1.7 Hz, 1H), 7.49-7.43 (m, 2H), 7.40-7.35 (m, 1H), 7.32 (d, J=8.2 Hz, 2H), 6.89 (dd, J=8.5, 7.2 Hz, 1H), 4.52 (s, 2H), 3.99 (s, 2H), 2.83 (t, J=6.7 Hz, 2H), 1.86 (t, J=6.7 Hz, 2H), 1.38 (s, 6H). LRMS [ESI, MH+] m/z calcd for C26H28NO5S 466.17. found 466.1.

Provenance & Evidence