[CH2:1]([N:3](C(C)C)[CH:4](C)C)C.[NH2:10][C:11]1[CH:19]=[CH:18][C:14]([C:15](O)=[O:16])=[CH:13][N:12]=1.CNC.CCN=C=NCCCN(C)C>C1COCC1>[NH2:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([N:3]([CH3:4])[CH3:1])=[O:16])=[CH:13][N:12]=1N-Ethyl-N-isopropylpropan-2-amine (12.61 mL, 72.40 mmol) was added to 6-aminonicotinic acid (CAS no. 3167-49-5) (5 g, 36.20 mmol), dimethylamine (2M in THF) (21.72 mL, 43.44 mmol) and EDCI (9.02 g, 47.06 mmol) in THF (150 mL) under nitrogen. The resulting suspension was stirred at r.t. for 18 hours. The reaction mixture was dry loaded onto silica and purified by flash silica chromatography, eluting with 0 to 10% MeOH in ethyl acetate to the product (4.50 g, 75%). 1H NMR (400 MHz, DMSO) δ 2.95 (6H, s), 6.28 (2H, s), 6.38-6.44 (1H, m), 7.42-7.47 (1H, m), 7.99-8.04 (1H, m)
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