D-Lactic Acid → HCID 25001555, compound

Participants

Reaction Steps

To a solution of 4-(2-fluoro-4-methylphenylamino)-7-methoxy-6-(piperazin-1-yl)cinnoline-3-carboxamide (Example 46, 0.395 g, 0.96 mmol) in CH2Cl2 (20 mL) and MeOH (5 mL) was added benzotriazol-1-yloxytripyrrolidino-phosphonium hexafluorophosphate (0.551 g, 1.06 mmol), (R)-2-hydroxypropanoic acid (0.079 mL, 1.06 mmol), and N-ethyldiisopropylamine (0.181 mL, 1.06 mmol). After 1 hour, an additional portion of benzotriazol-1-yloxytripyrrolidino-phosphonium hexafluorophosphate (1.10 g, 2.12 mmol) was added. After 2 hours, water (100 mL) was added, and the mixture extracted with CH2Cl2. The organic extract was concentrated under reduced pressure, and the residue purified with silica chromatography (Hex/EtOAc, then with CH2Cl2/MeOH). The crude product was triturated with CH3CN and filtered to give 173 mg (37%) yellow solid. 1H NMR: 11.33 (s, 1H), 8.77 (s, 1H), 7.91 (s, 1H), 7.60 (s, 1H), 7.17 (m, 2H), 7.06 (m, 1H), 6.62 (s, 1H), 4.98 (d, 1H), 4.39 (m, 1H), 4.01 (s, 3H), 3.54 (m, 4H), 2.72 (m, 4H), 2.32 (s, 3H), 1.16 (d, 3H); m/z 484.

Provenance & Evidence