## 3 Materials and Methods
### Chemical Syntheses
#### 3.2.5 Preparation of Phenyl(4-benzyloxy)-7-morpholinobenzo[_d_]thiazol-2-yl)carbamate (6)
The resulting precipitate was collected by filtration and dried at 60 \({}^{\circ}\)C to afford the title compound (400 mg, 83%) as beige crystals, mp 210 \({}^{\circ}\)C.  
\({}^{1}\)H-NMR (400 MHz, DMSO-\(d_{6}\)) \(\delta\) 1.14 (s, 3H, CH\({}_{3}\)), 1.35-1.53 (m, 4H, Pip-C\({}^{3}\)H\({}_{2}\) + Pip-C\({}^{5}\)H\({}_{2}\)), 3.00 (t, 4H, \(J\) = 4.5 Hz, CH\({}_{2}\)NCH\({}_{2}\)), 3.19-3.32 (m, 2H, 0.5 Pip-C\({}^{2}\)H\({}_{2}\) + 0.5 Pip-C\({}^{6}\)H\({}_{2}\)), 3.76 (t, 4H, \(J\) = 4.5 Hz, CH\({}_{2}\)OCH\({}_{2}\)), 3.79-3.90 (m, 2H, 0.5 Pip-C\({}^{2}\)H\({}_{2}\) + 0.5 Pipc\({}^{6}\)H\({}_{2}\)), 4.42 (s\({}_{\text{br}}\), 1H, OH), 5.17 (s, 2H, Bn-CH\({}_{2}\)), 6.78 (d, 1H, \(J\) = 8.5 Hz, H\({}^{6}\)), 6.96 (d, 1H, \(J\) = 8.5 Hz, \(H^{5}\)), 7.30-7.55 (m, 5H, C\({}_{6}\)H\({}_{5}\)), 12.21 (s\({}_{\text{br}}\), 1H, NH), \({}^{13}\)C-NMR (100 MHz, DMSO-\(d_{6}\)) \(\delta\) 30.3 (CH\({}_{3}\)), 38.7 (Pip-C\({}^{3,5}\)), 40.8 (Pip-C\({}^{2,6}\)), 51.9 (CNC), 66.5 (Pip-C\({}^{4}\)), 67.1 (COC), 70.7 (Bn-CH\({}_{2}\)), 109.7 (C\({}^{5}\)), 112.4 (C\({}^{6}\)), 127.4 (C\({}^{7a}\)), 128.9, 128.7, 128.4, (Bn-C\({}^{2,3,4}\)), 137.6 (Bn-C\({}^{1}\)), 140.4 (C\({}^{3a}\)), 147.3 (C\({}^{7}\)), 150.7 (C\({}^{4}\)), 153.7 (C=O), 160.4 (C\({}^{2}\)). Anal. calcd for C\({}_{25}\)H\({}_{30}\)N\({}_{4}\)O\({}_{4}\)S: C, 62.22; H, 6.27; N, 11.61; found: C, 62.20; H, 6.23; N, 11.56. HRMS \(m/z\): [M + H]\({}^{+}\) calcd: 483.2061; found: 483.2055. 3.2.7. Preparation of 4-Hydroxy-\(N\)-(4-hydroxy-7-morpholinobenzo[_d_]thiazol-2-yl)-4-methylpiperidine-1-carboxamide (8) [34]  
Ammonium formate (380 mg, 6 mmol) followed by 10% Pd/C (300 mg, 0.3 mmol) were added to a stirred solution of 7 (482 mg, 1 mmol) in anhydrous DMF (5 mL). The flask was sealed with a bubble counter and immersed in a pre-heated (55 \({}^{\circ}\)C) oil bath. The reaction mixture was stirred at 55 \({}^{\circ}\)C for ten min (TLC: ethyl acetate/hexane, 80/20, R\({}_{\text{fs,m}}\), 0.42, R\({}_{\text{fp}}\) 0.08-0.2, extended spot), cooled to ambient temperature and filtered through a layer of Quartz/Celite (prewetted with DMF). The filter cake was washed with DMF, the combined filtrate and washings were poured into ice/half-saturated brine (50:50, 50 mL) and the resulting mixture was stirred for 10 min. Crystallization was induced by scratching with a glass rod and the mixture was cooled to 5 \({}^{\circ}\)C overnight. The solid was collected by filtration, washed with MeOH and dried at 50 \({}^{\circ}\)C to afford the title compound (290 mg, 74%) as a light grey solid. For further purification, the solid was dissolved in a minimum amount of hot DMF and the same volume of water was added. The nearly colorless precipitate formed upon cooling was collected by filtration and treated with boiling MeOH. After cooling to ambient temperature, the solid was collected by filtration, washed with MeOH and dried at 50 \({}^{\circ}\)C, mp 265 \({}^{\circ}\)C (dec.). \({}^{1}\)H-NMR (400 MHz, DMSO-\(d_{6}\)) \(\delta\) 1.15 (s, 3H, CH\({}_{3}\)), 1.57-1.33 (m, 4H, Pip-C\({}^{3}H_{2}\) + Pip-C\({}^{5}H_{2}\)), 2.96 (t, 4H, \(J\) = 4.5 Hz, CH\({}_{2}\)NC\(H_{2}\)), 3.19-3.32 (m\({}_{\rm obsc}\), 2H, 0.5 Pip-C\({}^{2}H_{2}\) + 0.5 Pip-C\({}^{6}H_{2}\)), 3.76 (t, 4H, \(J\) = 4.5 Hz, CH\({}_{2}\)OCH\({}_{2}\)), 3.80-3.96 (m, 2H, 0.5 Pip-C\({}^{2}H_{2}\) + 0.5 Pip-C\({}^{6}H_{2}\)), 3.76 (t, 4H, \(J\) = 4.5 Hz, CH\({}_{2}\)OCH\({}_{2}\)), 3.80-3.96 (m, 2H, 0.5 Pip-C\({}^{2}H_{2}\) + 0.5 Pip-C\({}^{6}H_{2}\)), 4.39 (s\({}_{\rm br}\), 1H, OH), 6.66-6.76 (m, 2H, \(H^{5}\), \(H^{6}\)), 9.37 (s\({}_{\rm br}\), 1H, OH), 11.16 (s\({}_{\rm br}\), 1H, NH). 13C-NMR (100 MHz, DMSO-\(d_{6}\)) \(\delta\) 30.2 (CH\({}_{3}\)). 38.6 (Pip-C\({}^{3}\)), 40.8 (Pip-C\({}^{2,6}\)), 51.8 (CNC), 66.5 (Pip-C\({}^{4}\)), 67.0 (COC), 109.5 (\(C^{5}\)), 112.2 (\(C^{6}\)), 127.1 (\(C^{7a}\)), 140.3 (\(C^{3a}\)), 140.5 (\(C^{7}\)), 147.1 (\(C^{4}\)), 153.6 (C=O), 160.7 (\(C^{2}\)). Anal. calcd for C\({}_{18}\)H\({}_{24}\)N\({}_{4}\)O4S: C, 55.08; H, 6.16; N, 14.28; found: C, 54.99; H, 6.11; N, 14.31.