Methanesulfonamide → HCID 71002230, compound

Participants

Reaction Steps

To a suspension of (R)-5-hydroxy-5-(5-(4-methyl-6-((4-(trifluoromethyl)pyridin-2-yl)amino)pyridin-2-yl)thiazol-2-yl)-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid (20 mg, 0.038 mmol) and methanesulfonamide (4.34 mg, 0.046 mmol) in DCM (2 mL) at rt was added HATU (28.9 mg, 0.076 mmol) followed by Hunig's base (0.040 mL, 0.228 mmol) and the mixture was stirred at rt for 16 h. The solvent was removed under reduced pressure, and the residue was purified by reverse phase HPLC using a C18 column and a solvent system of MeCN and water modified with 0.1% TFA. The product-containing fractions were collected and lyophilized to give (R)-5-hydroxy-5-(5-(4-methyl-6-((4-(trifluoromethyl)pyridin-2-yl)amino)pyridin-2-yl)thiazol-2-yl)-N-(methylsulfonyl)-5,6,7,8-tetrahydronaphthalene-2-carboxamide (22.4 mg, 82%) as light yellow solid. MS ESI calcd for C27H24F3N5O4S2 [M+H]+ 604, found 604. 1H NMR (500 MHz, dmso) δ 10.21 (s, 1H), 8.65 (s, 1H), 8.48 (s, 1H), 8.22 (d, J=3.9, 1H), 7.74 (s, 1H), 7.69-7.61 (m, 1H), 7.39-7.29 (m, 2H), 7.26-7.17 (m, 1H), 7.10 (s, 1H), 3.34 (s, 3H), 2.87 (m, 2H), 2.40-2.32 (m, 2H), 2.30 (s, 3H), 2.17-2.06 (m, 1H), 2.05-1.88 (m, 1H) ppm.

Provenance & Evidence