tert-butyl rel-{(3R,4R)-3-[(5-bromo-6-cyanopyridin-3-yl)amino]-1,1-dioxidotetrahydro-2H-thiopyran-4-yl}carbamate → rel-5-{[(3R,4R)-4-amino-1,1-dioxidotetrahydro-2H-thiopyran-3-yl]amino}-[(4-methoxy-6-methylpyridin-2-yl)amino]pyridine-2-carboxamide TFA salt

Participants

Reaction Steps

rel-5-{[(3R,4R)-4-amino-1,1-dioxidotetrahydro-2H-thiopyran-3-yl]amino}-[(4-methoxy-6-methylpyridin-2-yl)amino]pyridine-2-carboxamide TFA salt (Enantiomer 2) was prepared from tert-butyl rel-{(3R,4R)-3-[(5-bromo-6-cyanopyridin-3-yl)amino]-1,1-dioxidotetrahydro-2H-thiopyran-4-yl}carbamate (Enantiomer 2, from Step 2 of Example 20) using chemistry analogous to that described for the synthesis of rel-5-{[(3S,4S)-4-amino-1,1-dioxidotetrahydro-2H-thiopyran-3-yl]amino}-3-[(4-methoxy-6-methylpyridin-2-yl)amino]pyridine-2-carboxamide (Example 20, Enantiomer 1). MS ESI calc'd. for C18H25N6O4S [M+H]+ 421. found 421. 1H NMR (500 MHz, DMSO-d6) δ 11.71 (s, 1H), 8.26-8.14 (m, 3H), 8.01 (s, 1H), 7.72 (s, 1H), 7.55-7.45 (br s, 1H), 6.74-6.20 (br s, 2H), 6.65 (s, 1H), 4.26 (s, 1H), 3.86-3.76 (m, 4H), 3.55-3.42 (m, 2H), 3.38-3.26 (m, 2H), 2.46-2.34 (m, 4), 2.30-2.21 (m, 1H).

Provenance & Evidence