Stannous chloride dihydrate → HCID 86647005, compound

Participants

Reaction Steps

A mixture of 12z (0.25 g, 0.66 mmol) and SnCl2.2H2O (1.35 g, 6.0 mmol) in methanol was refluxed for 48 h. Evaporation of the solvent under reduced pressure afforded 4-(3aminophenyl)-N-(5-chloro-2-methoxyphenyl)-5-methylthiazol-2-amine as a solid which was dissolved in chloroform and cooled in an ice bath to 0° C. Triethylamine (93 μL, 0.66 mmol) was added and the mixture was stirred for 15 min at the same temperature. Pivaloyl chloride (0.08 g, 0.66 mmol) was then added dropwise at 0° C. and the mixture was stirred overnight at which point the mixture was poured onto ice-cold water and the aqueous layer was extracted with DCM. The collected organic extract was washed with sat. aq. NaHCO3 and brine, dried over anhydrous MgSO4, and filtered. Evaporation of the solvent under reduced pressure afforded 13z as a yellowish white solid (0.21 g, 75%). Mp decomposition at 195° C. 1H NMR (300 MHz, CDCl3): δ 7.83 (s, 1H), 7.76 (s, 1H), 7.45 (m, 1H), 7.38 (d, J=2.40 Hz, 1H), 7.33 (s, 1H), 7.27 (m, 1H), 6.93 (d, J=9.0 Hz, 1H), 3.89 (s, 3H), 2.42 (s, 3H), 1.33 (s, 9H). 13C NMR (150 MHz, CDCl3): δ 177.4, 168.4, 151.5, 139.1, 129.9, 127.8, 125.9, 124.3, 123.6, 121.3, 120.3, 118.5, 114.5, 113.3, 111.4, 111.0, 56.4, 39.9, 27.7, 12.5. HRMS m/z (ESI) calcd. for C22H24ClN3O2S (M+H)+ 430.1351. Found 430.1345.

Provenance & Evidence