Ethanol hydrochloride → 6-Cyclopentadienyl-2-cyclopropyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-1,3-benzoxazole-4-carbonitrile

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2-Cyclopropyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-6-(3-hydroxycyclopent-1-enyl)-5-methyl-1,3-benzoxazole-4-carbonitrile (I-306) (83 mg, 0.21 mmol) was dissolved in ethanol (0.85 ml) and diethyl ether (1.7 ml), and at room temperature, 1 M hydrochloric acid/ethanol solution (222 μl, 0.22 mmol) was added. After stirring at the same temperature for 4 hours, the solvent was evaporated away under reduced pressure. Ether was added to the residue, and this was concentrated under reduced pressure. This operation was repeated once again. Ether was added to the residue, followed by sonication, and the solvent was removed with a pipette. The residue was dried at 60° C. under reduced pressure for 2 hours to obtain the entitled compound (62 g, 65%) as a brown solid.

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