Diisopropylethylamine → HCID 57955617, compound

Participants

Reaction Steps

To a solution of 4-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxybenzoic acid (100 mg, 0.22 mmol) in DMF (1 mL) was added tert-butyl 4-(3-aminoazetidin-1-yl)piperidine-1-carboxylate (72 mg, 0.25 mmol), HATU (125 mg, 0.33 mmol), and DIEA (80 μL, 0.44 mmol). The reaction mixture was stirred for 1 h. It was then poured into 100 mL of rapidly stirring water. A white solid forms and was filtered, washed with water and dried. This solid was treated with TFA in DCM (3 mL 1:1) for 2 days. The solvent was then removed, and the product purified by reverse phase HPLC, free based and lyophilized to yield a white solid (17.8 mg, 14% yield 1H NMR (400 MHz, DMSO-d6) δ ppm 1.02 (br. s., 2 H) 1.50-1.79 (m, 9 H) 1.93 (br. s., 2 H) 2.07 (br. s., 1 H) 2.35-2.44 (m, 2 H) 2.85-3.00 (m, 4 H) 3.52 (t, J=7.20 Hz, 2 H) 3.94 (s, 3 H) 4.05 (t, J=14.02 Hz, 2 H) 4.37-4.50 (m, 1 H) 4.68-4.84 (m, 1 H) 7.47-7.52 (m, 2 H) 7.98 (s, 1 H) 8.26 (s, 1 H) 8.29 (d, 1 H) 8.61 (d, J=6.57 Hz, 1 H). [M+H] calc'd for C29H38F2N8O3, 585; found 585.

Provenance & Evidence