Diisopropylamine → HCID 118092531, compound

Participants

Reaction Conditions

Reaction Steps

n-BuLi (1.6 M, 303 μL, 0.484 mmol) was added to diisopropylamine (67.3 μL, 0.473 mmol) in THF (394 μL) at −78° C. The reaction was warmed to −40° C. and was stirred for 1 hour. The reaction mixture was cooled back to −78° C. and a solution of pyrrolidin-2-one (15.1 mg, 0.177 mmol) in THF (100 μL) was added dropwise. The reaction mixture was warmed to −40° C. and stirred for 1 hour. The reaction mixture was cooled back to −78° C. and a solution of N-{3-[6-(bromomethyl)pyridin-3-yl]-5-methylphenyl}-4-(trifluoromethyl)pyrimidin-2-amine (50.0 mg, 0.118 mmol) in THF (300 μL) was added. The reaction mixture was slowly warmed to room temperature and quenched with saturated aqueous ammonium chloride (1.00 mL) and THF was removed under reduced pressure. The reaction mixture was extracted with dichloromethane and the organic was dried over sodium sulfate and concentration under reduced pressure. The residue was purified by reverse phase prep HPLC (10-80% MeCN in water with 0.5% TFA) to yield 1-{[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]methyl}pyrrolidin-2-on. MS APCI calc'd for C22H21F3N5O [M+H]+ 428. found 428. 1H NMR (500 MHz, DMSO-d6) δ 10.28 (s, 1H), 8.82 (d, J=4.9 Hz, 1H), 8.78 (d, J=2.0, 1H), 8.04 (dd, J=2.3 Hz, 8.1 Hz, 1H), 7.95 (s, 1H), 7.56 (s, 1H), 7.38 (d, J=8.1, 1H), 7.27 (d, J=4.9 Hz, 1H), 7.20 (s, 1H), 4.52 (s, 3H), 4.38 (br s, 2H), 3.37 (t, J=7.0 Hz, 2H), 2.31 (t, J=8.1 Hz, 2H), 1.96 (q, J=7.6 Hz, 15.1 Hz, 2H).

Provenance & Evidence