Methyl N-(triethylammoniosulfonyl)carbamate → HCID 71577056, compound

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Reaction Steps

A mixture of N′-acetoyl-5-chloro-2-methoxy-4-(4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-ylamino)benzohydrazide (68 mg, 0.16 mmol), and 1-methoxy-N-triethylammoniosulfonyl-methanimidate (Burgess reagent) (75 mg, 0.32 mmol) in THF (4 mL) was irradiated in the microwave at 150° C. for 30 min. An additional portion of Burgess reagent (75 mg, 0.32 mmol) was added and the reaction was irradiated a further 30 min at 150° C. in the microwave. The reaction mixture was concentrated and the crude residue purified via silica gel column chromatography (0-100% ethyl acetate/isohexane) to afford a residue that was triturated with diethyl ether/methanol yielding N2-(2-chloro-5-methoxy-4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl)-N4-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine as a white solid (28 mg, 43%). HPLC (15 cm_Formic_Ascentis_HPLC_CH3CN): at 9.15 min. LCMS (10 cm_ESCI_Formic_MeCN): [MH+]=415 at 4.00 min. 1H NMR (400 MHz, CDCl): δ 8.62 (s, 1H); 8.25 (s, 1H); 7.95 (s, 1H); 7.80 (s, 1H); 5.34 (s, 1H); 4.01 (s, 3H); 3.15 (d, J=4.7, 3H); 2.61 (s, 3H).

Provenance & Evidence