[CH:1]1([C:5]2[NH:9][N:8]=[C:7]([NH2:10])[CH:6]=2)[CH2:4][CH2:3][CH2:2]1.[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1.[CH3:20][C:21]1(C)OC(=O)CC(=O)[O:22]1>CCO>[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]2[CH2:20][C:21](=[O:22])[NH:10][C:7]3=[N:8][NH:9][C:5]([CH:1]4[CH2:4][CH2:3][CH2:2]4)=[C:6]23)=[CH:14][CH:13]=1To 5-cyclobutyl-1H-pyrazol-3-ylamine (1.0 g, 7.3 mmol) in EtOH (20 mL) was added 4-chlorobenzaldehyde (1.1 g, 8.0 mmol) followed by Meldrum's Acid (1.1 g, 8.0 mmol). The reaction mixture was then heated to 75° C. (oil bath). After 30 min, the reaction was cooled to room temperature, the solid was filtered off, and then washed with MeOH (5 mL) and hexanes (10 mL). The solid was collected and dried under reduced pressure to give the title compound (1.3 g, 59% yield) as a colorless solid. 500 MHz 1H NMR (DMSO-d6) d 12.0 (s, 1H), 10.3 (s, 1H), 7.34 (d, J=8.7 Hz, 2H), 7.11 (d, J=8.3 Hz, 2H), 4.20 (dd, J=7.1, 4.2 Hz, 1H), 3.17 (dddd, J=8.7, 8.7, 8.7, 8.7 Hz, 1H), 2.84 (dd, 15.8, 7.1 Hz, 1H), 2.44 (dd, J=16.2, 4.6 Hz, 1H), 2.09-1.87 (m, 4H), 1.83-1.69 (m, 1H), 1.68-1.61 (m, 1H). 13C NMR (125 Mz, DMSO-d6) d 169.8, 149.5, 144.1, 142.8, 131.7, 129.4, 129.2, 101.1, 41.3, 33.9, 31.0, 28.8, 28.4, 18.7. LRMS m/z (APCI+) 303 (M+1).
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