5-Phenyl-6-[4-({[4-(1,2,3-thiadiazol-4-yl)benzyl]amino}methyl)phenyl]nicotinonitrile → HCID 178420071, compound

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Reaction Steps

A mixture of 5-phenyl-6-[4({[4-(1,2,3-thiadiazol-4-yl)benzyl]amino}methyl)phenyl]nicotinonitrile (1-5; TFA salt) (69 mg, 0.1 mmol), 2M of NaN3 water solution (0.75 mL, 1.5 mmol), 2M of ZnBr2 water solution (0.5 mL, 1.0 mmol) was microwaved (Smith-Synthesizer) at 165° C. for 15 min. After this time, the solution was concentrated. The residue was re-dissolved in DMSO (1 mL) and purified by LCMS to afford the pure desired product (TFA salt) as a slightly yellow solid (1-6). Analytical LCMS: single peak (214 nm), 2.339 min. 1H NMR (500 MHz, DMSO-d6): δ 9.70 (s, 1H), 9.32 (d, J=2.1 Hz, 1H), 8.42 (d, J=2.1 Hz, 1H), 8.22 (d, J=8.2 Hz, 2H), 7.68 (d, J=8.3 Hz, 2H), 7.42-7.48 (M, 4H), 7.35-7.40 (m,3H), 7.28-7.32 (m, 2H), 4.26 (s, 2H), 4.23 (s, 2H); HRMS, calc'd for C28H22N8S (M+1), 503.1761; found 503.1769.

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