Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: Br[C:2]1[CH:3]=[C:4]([CH:8]2[C:13](=[O:14])[NH:12][C:11]3[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=3[O:9]2)[CH:5]=[CH:6][CH:7]=1.O.[CH3:20][N:21](C=O)C>[C-]#N.[Zn+2].[C-]#N>[C:20]([C:2]1[CH:3]=[C:4]([CH:8]2[C:13](=[O:14])[NH:12][C:11]3[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=3[O:9]2)[CH:5]=[CH:6][CH:7]=1)#[N:21]
Reactant: O=C1Nc2ccccc2OC1c1cccc(Br)c1
Reactant: CN(C)C=O
Agent: [C-]#N
Agent: [Zn+2]
Solvent: O
Product: N#Cc1cccc(C2Oc3ccccc3NC2=O)c1
Temperature: 100 °C
Yield: 76 %

Procedure:
To a solution of 2-(3-bromophenyl)-3,4-dihydro-2H-1,4-benzoxazin-3-one (I7) (3.00 g, 9.87 mmol) in DMF (20 mL) was added Zinc cyanide (0.68 g, 5.79 mmol) and then tetrakistriphenylphosphine palladium (0) (0.96 g, 8 mol %). The degassed solution was heated at 100° C. for 5 hours, cooled to room temperature, and then treated with water (50 mL). The product was extracted into ethyl acetate (2×100 mL), washed with brine (50 mL), dried over MgSO4, and then purified by silica gel chromatography, eluant 50% ethyl acetate in hexane. This process affords the title compound (1.866 g, 76%) that was recrystallized from ethanol/water.
Reaction SMILES: O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)=[CH:13][C:12]2=[O:25])=[CH:5][CH:4]=1.[NH:26]1[CH2:31][CH2:30][CH:29]([NH:32][C:33](=[O:35])[CH3:34])[CH2:28][CH2:27]1>>[O:25]=[C:12]1[CH:13]=[C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH:15]=[CH:16][N:11]1[CH2:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][N:26]2[CH2:31][CH2:30][CH:29]([NH:32][C:33](=[O:35])[CH3:34])[CH2:28][CH2:27]2)=[CH:4][CH:5]=1
Reactant: CC(=O)NC1CCNCC1
Reactant: O=c1cc(OCc2ccccn2)ccn1CCc1ccc(CO)cc1
Product: CC(=O)NC1CCN(Cc2ccc(CCn3ccc(OCc4ccccn4)cc3=O)cc2)CC1

Procedure:
N-[1-(4-{2-[2-Oxo-4-(pyridin-2-ylmethoxy)-2H-pyridin-1-yl]-ethyl}-benzyl)-piperidin-4-yl]-acetamide is prepared as example 3.1b from 150 mg (0.45 mmol) 1-[2-(4-hydroxymethylphenyl)-ethyl]-4-(pyridin-2-ylmethoxy)-1H-pyridin-2-one (example 3.1a) and 127 mg (0.89 mmol) N-piperidin-4-yl-acetamide. The product is purified via reverse HPLC chromatography (Zorbax stable bond, C18; water (0.1% formic acid)/acetonitrile (0.1% formic acid) 95:5 to 10:90).