5-Bromonicotinic acid → 5-bromo-N-(4'-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl1,1'-biphenyl-3-yl)nicotinamide

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Reaction Steps

5′-Amino-N-(cyclopropylmethyl)-2′-methyl-1,1′-biphenyl-4-carboxamide (26.4 mg, 0.009 mmol) and 5-bromonicotinic acid (38 mg, 0.18 mmol) were mixed in THF (2 ml) and the mixture shaken in a varian tube for 5 min at room temperature. Carbodiimde resin (250 mg, 0.27 mmol) was added and shaking continued for 72 h. The solution was filtered off and concentrated under vacuum. The residue was chromatographed on a silica gel flash column eluting with ethyl acetate/hexane (1:2 then 1:1) and the solvent evaporated under vacuum to give 5-bromo-N-(4′-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl1,1′-biphenyl-3-yl)nicotinamide (37 mg, 85%). NMR; δH [2H6]—DMSO 10.50,(1H, s), 9.05,(1H, m), 8.90,(1H, m), 8.62,(1H, t), 8.54,(1H, t), 7.93,(2H, d), 7.70,(1H, dd), 7.66,(1H, d), 7.44,(2H, d), 7.31,(1H, d), 3.16,(2H, t), 2.21,(3H, s), 1.04,(1H, m), 0.43,(2H, m). LCMS: retention time 3.44 min, MH+464/466.

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