Sodium cyanoborohydride → N*3*-(3,5-Dichloro-phenyl)-N*5*-(1-methanesulfonyl-piperidin-4-yl)-1H-[1,2,4]triazole-3,5-diamine

To a stirred solution of N3-(3,5-dichlorophenyl)-1H-1,2,4-triazole-3,5-diamine Intermediate 2 (122 mg, 0.50 mmol) in methanol (8 mL) at rt, was added 1-(methylsulfonyl)piperidin-4-one (89 mg, 0.50 mmol). The mixture was stirred for 2 hrs, after which, sodium cyanoborohydride (94.2 mg, 1.5 mmol) and three drops of acetic acid were added. The reaction mixture was stirred at rt for 6 hrs, then diluted with water (25 mL) and extracted with EtOAc (3×10 mL). The extracts were dried with sodium sulfate and the solvent was removed under reduced pressure. The residue was chromatographed on a silica gel column to give 16 mg (8%) of desired product as a white solid. MS +m/z: 404.9 (M+H)+

1. stirringThe reaction mixture was stirred at rt for 6 hrs
2. extractionextracted with EtOAc (3×10 mL)
3. dry with materialThe extracts were dried with sodium sulfate
4. customthe solvent was removed under reduced pressure
5. customThe residue was chromatographed on a silica gel column

ORD-Eintrag

ord-35ea24d76d614e88b3802581edf5bb1a

Quelldatensatz

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09428469B2