HCID 90449869, Verbindung → HCID 90449833, Verbindung

The 1′-acetyl-N-(5-chlorothiazol-2-yl)-5-formylspiro[indoline-3,3′-pyrrolidine]-1-carboxamide (30.0 mg, 0.074 mmol) obtained in Step 2 of Example 401 was dissolved in tetrahydrofuran (1.4 mL). Thereafter, methyl magnesium bromide (1 M tetrahydrofuran solution, 224 μL) was added to the above obtained solution under cooling on ice, and the thus obtained mixture was then stirred at the same temperature as above for 1 hour. Thereafter, the reaction solution was diluted with a saturated aqueous solution of ammonium chloride, and was then extracted with chloroform. The organic layer was washed with brine, and was then dried over anhydrous sodium sulfate, followed by concentration in vacuo. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:1) to obtain the captioned compound (28.1 mg, 91%) in the form of a white solid.