Methanol → 2-Amino-3-(4-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-propionic acid methyl ester hydrochloride salt

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Reaction Steps

Thionyl chloride (27.5 mL) was added dropwise over 15 minutes to a cooled (0° C.) suspension of 2-amino-3-(4-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-propionic acid hydrochloride (7.28 g, 22.3 mmol) in methanol (150 mL). On complete addition, the mixture was heated under reflux for 66 hours. The mixture was allowed to cool to ambient temperature and evaporated. The resultant residue was azeotroped with toluene (2×150 mL) to afford the title compound as a fawn solid (7.7 g, 99%). 1H NMR (400 MHz, DMSO-d6): 12.06 (s, 1H), 8.39 (s, 3H), 8.17 (d, J=5.2 Hz, 1H), 7.50 (d, J=2.5 Hz, 1H), 7.19 (d, J=5.2 Hz, 1H), 4.07-4.06 (m, 1H), 3.54 (dd, J=14.9, 5.8 Hz, 1H), 3.30 (dd, J=14.9, 9.0 Hz, 1H).

Provenance & Evidence