Cl[C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][C:3]=1[F:10].[NH:11]1[CH2:14][CH:13]([N:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH3:22])[CH2:17][CH2:16]2)[CH2:12]1.C(C1C=CC=CC=1)C1C=CC=CC=1.C1CCN2C(=NCCC2)CC1>O.CN1C(=O)CCC1>[CH2:21]([N:18]1[CH2:19][CH2:20][N:15]([CH:13]2[CH2:12][N:11]([C:2]3[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][C:3]=3[F:10])[CH2:14]2)[CH2:16][CH2:17]1)[CH3:22]
To a mixed solution of a commercially available product of (6-chloro-5-fluoropyridin-2-yl)methanol (200 mg, 1.24 mmol) and NMP (2.00 mL) were added a mixture (627 mg) of 1-(azetidin-3-yl)-4-ethylpiperazine and benzylbenzene described in Production Example 1-3-2 and DBU (565 mg, 3.71 mmol) at room temperature. The resultant mixture was irradiated with a microwave at 180° C. for 8 hours. The reaction mixture was cooled to room temperature, then water was added thereto, and the resultant solution was extracted with dichloromethane. An organic layer was dried over anhydrous magnesium sulfate and then filtrated. The solvent was evaporated under a reduced pressure, and the resultant residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:4 and subsequently ethyl acetate) to give a crude product (402 mg) of the title compound.
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