1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 66550546, compound

Participants

Reaction Steps

To a solution of (S)-4-(7-(3-(2-methylpyrrolidin-1-yl)phenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzoic acid (80 mg, 0.19 mmol) and N1,N1-dimethylethane-1,2-diamine (18 mg, 0.2 mmol) in DCM (20 mL) was added 1-methyl-1H-indozole (92 mg, 1.12 mmol) and EDCI (217 mg, 1.12 mmol). The reaction mixture was stirred at room temperature for 3 h. The solvent was removed in vacuo and the residue was purified by column chromatography (DCM:MeOH=50:1) and product treated with conc. HCl to give (S)—N-(2-(dimethylamino)ethyl)-4-(7-(3-(2-methylpyrrolidin-1-yl)phenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzamide (22 mg, 24%) as HCl salt. 1H NMR (300 MHz, CD3OD): δ 9.15 (s, 1H), 8.37 (s, 1H), 8.34 (s, 1H), 8.27 (s, 1H), 7.97-7.91 (m, 3H), 7.63-7.57 (m, 1H), 7.41 (d, 1H, J=8.1 Hz), 4.06-3.93 (m, 2H), 3.77-3.68 (m, 3H), 3.37-3.33 (m, 2H), 2.91 (s, 6H), 2.53-2.42 (m, 1H), 2.35-2.18 (m, 2H), 2.06-1.87 (m, 1H), 1.36 (d, 3H, J=6.6 Hz). LC-MS: 502 [M+H]+, tR=1.344 min. HPLC: 97.57% at 214 nm, 97.17% at 254 nm, tR=4.793 min.

Provenance & Evidence