HCID 68323240, compound → HCID 70800909, compound

Participants

Reaction Steps

To a solution of (5-((6-phenylbenzo[d]thiazol-2-yl)methyl)-1,3,4-oxadiazol-2-yl)methanamine (788 mg, 2.44 mmol) (described in WO 2011/074560) in dichloromethane (10 mL) was added N-(tert-butoxycarbonyl)-N-[4-(dimethylazaniumylidene)-1,4-dihydropyridin-1-ylsulfonyl]azanide (737 mg, 2.44 mmol), Winum, J.-Y. et al., Org. Lett., 3(14):2241-2243 (2001), and the reaction mixture stirred for 3 days. The reaction mixture was diluted with sat′d NH4Cl and the solution extracted with EtOAc (3×). The combined organic extracts were washed with brine, dried (Na2SO4) filtered and concentrated under reduced pressure. The residue was purified on silica gel eluting with 10-100% EtOAc/DCM to give Compound 24a (1.2 g, 95% yield) as a brown oil. LCMS=0.99 min using analytical method (B), 502.0 (M+H). 1H NMR (400 MHz, CDCl3) δ 8.07 (d, J=8.5 Hz, 1H), 8.06 (s, 1H), 7.74 (dd, J=8.4, 1.9 Hz, 1H), 7.68-7.61 (m, 2H), 7.49 (t, J=7.4 Hz, 2H), 7.44-7.36 (m, 1H), 6.96 (br. s., 1H), 5.26 (br. s., 2H), 4.79 (s, 2H), 4.63 (s, 2H), 1.37 (s, 9H).

Provenance & Evidence