Cl.C(N=C=N)C.[NH2:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][N:12]=[C:11]2[NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=1.N1C=CC=CC=1.[CH2:32]1C[O:35][CH2:34][CH2:33]1.CN(C=O)C>>[ClH:25].[Cl:25][C:21]1[CH:20]=[C:19]([NH:18][C:11]2[C:10]3[C:15](=[CH:16][CH:17]=[C:8]([NH:7][C:34](=[O:35])[CH:33]=[CH2:32])[CH:9]=3)[N:14]=[CH:13][N:12]=2)[CH:24]=[CH:23][CH:22]=11-3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1902 mg, 1 mmol) was added to a solution of 6-amino-4[(3-chlorophenyl)amino]quinazoline (136 mg, 0.5 mmol) acrylic acid (74 mg, 1.0 mmol) and pyridine (201 mg, 2.5 mmol) in THF/DMF (4:1, 2.5 mL), stirred under nitrogen at 0° C. After 20 minutes the reaction mixture was stirred at 25° C. for 3 hours, and then poured onto water (12.5 mL), and extracted with EtOAc (2×10 mL). The combined extracts were treated with dilute hydrochloric acid (0.5 M, 10 mL), and the precipitate was collected by Buchner filtration, rinsed with water (10 mL), ether (2×10 mL), and air dried to give N-[4-[(3-chlorophenyl)amino]quinazolin-6-yl]acrylamide hydrochloride (93 mg, 48%) as a dull yellow solid, mp 223-227° C.
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