Cl.[NH2:2][C@H:3]1[CH2:6][C@H:5]([N:7]2[C:11]3=[N:12][CH:13]=[C:14]([F:16])[CH:15]=[C:10]3[C:9]([F:18])([F:17])[C:8]2=[O:19])[CH2:4]1.Cl[C:21]1[S:22][C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=1.C(N(CC)C(C)C)(C)C>CS(C)=O.O>[S:22]1[C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=[C:21]1[NH:2][C@H:3]1[CH2:6][C@H:5]([N:7]2[C:11]3=[N:12][CH:13]=[C:14]([F:16])[CH:15]=[C:10]3[C:9]([F:18])([F:17])[C:8]2=[O:19])[CH2:4]11-(Trans-3-aminocyclobutyl)-3,3,5-trifluoro-1H-pyrrolo[2,3-b]pyridin-2(3H)-one hydrochloride (0.105 g, 0.358 mmol), 2-chlorobenzothiazole (0.0728 g, 0.429 mmol), and N,N-diisopropylethylamine (0.249 mL, 1.430 mmol) were mixed in DMSO (0.5 mL) in a sealed tube. The reaction mixture was stirred at 120° C. for 1.5 h. The reaction mixture was cooled to room temperature, diluted with water, and extracted with EtOAc. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting crude product was purified by silica gel column chromatography eluting with EtOAc in hexanes to yield the title compound (0.032 g, 0.082 mmol, 22.9% yield) as a white solid. M+1: 391.1 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.46-2.56 (m, 2 H) 3.37-3.48 (m, 2 H) 4.58 (m, J=3.50 Hz, 1 H) 5.23 (quin, J=8.61 Hz, 1 H) 5.76 (br. s., 1 H) 7.12 (t, J=7.53 Hz, 1 H) 7.32 (t, J=7.73 Hz, 1 H) 7.56-7.66 (m, 3 H) 8.30 (s, 1 H).
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