Sodium Bicarbonate → 6-chloro-imidazo[2,1-b]thiazole-5-sulfonic acid (2-methyl-2,3,4,9-tetrahydro-1H-beta-carbolin-6-yl)-amide

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Reaction Steps

To a solution of 6-amino-2-methyl-2,3,4,9-tetrahydro-1H-β-carboline (description 2) (150 mg, 0.68 mmol) in pyridine (5 mL) cooled in an ice bath, were added 200 mg of 6-chloro-imidazo[2,1-b]thiazole-5-sulfonyl chloride (0.68 mmol). Under N2, the reaction mixture was left to reach room temperature and stirred for 1 h at this temperature. The reaction mixture was basified with aqueous saturated solution of NaHCO3 and the pyridine evaporated. The mixture was treated with EtOAc and H2O, the organic phase washed with aqueous saturated solution of NaHCO3, separated and dried with Na2SO4. The crude was further purified using SiO2 column chromatography with EtOAc/MeOH/NH3 mixtures to yield 130 mg of 6-chloro-imidazo[2,1-b]thiazole-5-sulfonic acid (2-methyl-2,3,4,9-tetrahydro-1H-β-carbolin-6-yl)-amide. Cream colored amorphous solid, mp 232-233° C. 1H-NMR (300 MHz, DMSO-d6): (ppm) 2.36 (s, 3H); 2.54 (bb, 2H); 2.61 (bb, 2H); 3.45 (bb, 2H); 6.65 (dd, 1H, J=8.7, 2.1 Hz); 6.99 (d, 1H, J=1.8 Hz); 7.09 (d, 1H, J=8.7 Hz); 7.53 (d, 1H, J=4.5 Hz); 7.81 (d, 1H, J=4.5 Hz); 10.37 (bb, 1H); 10.74 (s, 1H).

Provenance & Evidence