Hydrochloric Acid → (R)-2-(3-(piperidin-1-yl)pyrrolidin-1-yl)benzo[d]thiazol-6-amine

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A solution of (R)-6-bromo-2-(3-(piperidin-1-yl)pyrrolidin-1-yl)benzo[d]thiazole (Example 14, 100 mg, 0.273 mmol), tri-tert-butylphosphine (66.3 mg, 0.033 mmol), tris(dibenxylideneacetone)dipalladium(0) (12.5 mg, 0.014 mmol) and lithium bis(trimethylsilyl)amide (63.9 mg, 0.382 mmol) in toluene (1 ml) was heated in a microwave reactor to 160° C. for 30 minutes. The mixture was treated with HCl (1 N, 1 mL) and stirred for 5 minutes. It was then basified with NaOH (10%), diluted with ether and partitioned. The organic was separated, dried with MgSO4 and concentrated under reduced pressure. The residue was chromatographed on silica gel column eluting with 2% (9:1 methanol:concentrated NH4OH) in dichloromethane to provide the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.43-1.52 (m, 2H), 1.58-1.68 (m, 4H), 1.91-2.07 (m, 1H), 2.20-2.34 (m, 1H), 2.39-2.56 (m, 4H), 2.90-3.05 (m, 1H), 3.39 (t, J=9.12 Hz, 1H), 3.46-3.58 (m, 3H), 3.66-3.76 (m, 1H), 3.82 (dd, J=9.52, 7.54 Hz, 1H), 6.69 (dd, J=8.33, 2.38 Hz, 1H), 6.96 (d, J=1.98 Hz, 1H), 7.39 (d, J=8.33 Hz, 1H); MS (DCI/NH3) m/z 303 (M+H)+.

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