[Cl:1][C:2]1[NH:3][C:4]([NH:11][CH2:12][C:13]2[N:14]=[CH:15][S:16][CH:17]=2)=[C:5]([F:10])[C:6](=[N:8][NH2:9])[N:7]=1.[CH:18]1([CH2:23][C@H:24]([CH2:28][N:29]([CH:37]=[O:38])[O:30][CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][O:32]2)[C:25](O)=[O:26])[CH2:22][CH2:21][CH2:20][CH2:19]1.CN1CCOCC1.C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][NH:9][C:25](=[O:26])[C@H:24]([CH2:23][CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22]2)[CH2:28][N:29]([O:30][CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][O:32]2)[CH:37]=[O:38])[C:5]([F:10])=[C:4]([NH:11][CH2:12][C:13]2[N:14]=[CH:15][S:16][CH:17]=2)[N:3]=12-Chloro-5-fluoro-6-[(1,3-thiazol-4-ylmethyl)amino]-4(1H)-pyrimidinone hydrazone (0.105 g) and (2R)-3-cyclopentyl-2-{[formyl(tetrahydro-2H-pyran-2-yloxy)amino]methyl}propanoic acid (0.182 g, 0.422 mmol) were dissolved in DMF (5 mL). NMM (0.21 mL, 1.91 mmol) was added, followed by HOAt (0.063 g, 0.463 mmol) and EDC (0.088 g, 0.459 mmol). After stirring for 2 days, the reaction mixture was purified by RP-HPLC to provide [(2R)-3-(2-{2-chloro-5-fluoro-6-[(1,3-thiazol-4-ylmethyl)amino]-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamide as a maroon solid (0.1133 g). LCMS: (M+H)+=556.0.
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