[Cl:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([O:12][CH2:13][C:14]([OH:16])=O)=[CH:8][C:9]=2[CH3:11])[N:4]([CH3:17])[N:3]=1.CN(C(ON1N=N[C:28]2[CH:29]=[CH:30][CH:31]=N[C:27]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CC[N:44]([CH:48]([CH3:50])[CH3:49])C(C)C.O.[CH3:52]N(C=O)C>>[Cl:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([O:12][CH2:13][C:14]([NH:44][C@H:48]([C:49]3[CH:27]=[CH:28][CH:29]=[CH:30][C:31]=3[CH3:52])[CH3:50])=[O:16])=[CH:8][C:9]=2[CH3:11])[N:4]([CH3:17])[N:3]=1To a solution of 2-((3-chloro-1,4-dimethyl-1H-pyrazolo[3,4-b]pyridin-6-yl)oxy)acetic acid in DMF (5 ml) was added HATU (1.03 g, 2.72 mmol) and DIPEA (1.2 ml, 6.81 mmol). After 20 min at rt, (S)-1-(p-tolylethan)amine (0.43 ml, 2.95 mmol) was added to the mixture. After 16 h, water was added and the mixture extracted with CH2Cl2. The organic phases were dried over Na2SO4 and the solvent removed under reduced pressure. Purification by column chromatography (eluent 60% hexane in EtOAc) yielded 420 mg (50%) of the title compound. [1H-NMR (DMSO-d6, 600 MHz) δ 8.51 (d, 1H), 7.16 (d, 2H), 7.05 (d, 2H), 6.63 (s, 1H), 4.93 (t, 1H), 4.83 (d, 1H), 4.79 (d, 1H), 3.77 (s, 3H), 2.60 (s, 3H), 2.25 (s, 3H), 1.35 (d, 3H); HPLC-MS RtJ=1.15 min; [M+H]+=373.1, 375.1]
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