[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]([C:19](O)=[O:20])=[N:11][C:12]3[N:13]([N:16]=[CH:17][CH:18]=3)[C:14]=2[F:15])=[C:4]([F:22])[CH:3]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)[N:41]=[N:40]C=2C=1.NN.CCN(CC)CC>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]([C:19]([NH:40][NH2:41])=[O:20])=[N:11][C:12]3[N:13]([N:16]=[CH:17][CH:18]=3)[C:14]=2[F:15])=[C:4]([F:22])[CH:3]=1A mixture of 6-(4-bromo-2-fluorophenylamino)-7-fluoropyrazolo[1,5-a]pyrimidine-5-carboxylic acid (1.00 equivalent), EDCI (1.50 equivalents), and HOBt (1.50 equivalents) in DMF is stirred for 30 minutes. Hydrazine (3.00 equivalents) is added followed by Et3N (2.50 equivalents). After 3 hours, the reaction mixture is diluted with EtOAc and washed with saturated NH4Cl solution, saturated NaHCO3 solution and brine. The organic layer is dried (MgSO4) and concentrated. The product is purified by flash chromatography as necessary.
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