(3S)-(-)-3-(Dimethylamino)pyrrolidine → 7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-2-(methoxymethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

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(3S)-3-(Dimethylamino)pyrrolidine (76 μl, 0.60 mmol) was added to a dimethyl sulfoxide (4 ml) solution of 7-fluoro-2-(methoxymethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-59) (58 mg, 0.20 mmol), followed by stirring at 90° C. for 1 hour. After cooling to room temperature, the above brown oily substance and saturated sodium bicarbonate water were added, followed by extraction three times with ethyl acetate, the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate. After filtration and concentration under reduced pressure, the resulting residue was subjected to column chromatography, and the eluate with chloroform:methanol (50:1) was concentrated under reduced pressure, the residue was dissolved in ethyl acetate, washed twice with saturated brine, then dried over anhydrous magnesium sulfate. After filtration and concentration tinder reduced pressure, the entitled compound (39 mg, 17%) was obtained as a brown oily substance.

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