2-Methyl-2-butanol → 2-[2-Fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-5-{[6-(2-hydroxy-1-morpholin-4-ylethyl)pyridin-2-yl]amino}-1,3-thiazole-4-carboxamide

Participants

Reaction Steps

The title compound was prepared as described in Example 1, Step 2 using 5-amino-2-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-1,3-thiazole-4-carboxamide (115 mg, 0.39 mmol), 2-(6-bromopyridin-2-yl)-2-morpholin-4-ylethanol (Enantiomer B) (Example 3, Step 1, chiral separation) (112 mg, 0.39 mmol), Pd2(dba)3 (36 mg, 0.039 mmol), X-PHOS (93 mg, 0.20 mmol), potassium carbonate (54 mg, 0.39 mmol), and tert-amyl alcohol (0.8 ml) as starting materials. 1H NMR (500 MHz, d6-DMSO) δ 11.25 (s, 1H), 8.29 (t, 1H), 7.86 (s, 1H), 7.70 (m, III), 7.65 (s, 1H), 7.42 (m, 2H), 7.10 (d, 1H), 6.92 (d, 1H), 5.24 (s, 1H), 4.47 (t, 1H), 4.00 (m, 2H), 3.65 (t, 1H), 3.54 (m, 4H), 2.51 (m, 4H), 1.44 (s, 6H). LRMS (APCI) calc'd for C24H29FN5O4S [M+H]+ 502.2, found 502.0.

Provenance & Evidence