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

HRID 1486591Notes

Reaction equation

HRID 1486591 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:14]=[C:13]([NH2:15])[NH:12][N:11]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.ClC1C=C(N=C=S)C=C(Cl)C=1C#N.[CH3:29][S:30]([N:33]1[CH2:38][CH2:37][C:36](=O)[CH2:35][CH2:34]1)(=[O:32])=[O:31].C([BH3-])#N.[Na+]>CO.C(O)(=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:14]=[C:13]([NH:15][CH:36]3[CH2:37][CH2:38][N:33]([S:30]([CH3:29])(=[O:32])=[O:31])[CH2:34][CH2:35]3)[NH:12][N:11]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

8

Reactant 4

HCID 5003444Sodium cyanoborohydrideHCID 120720291-(Methylsulphonyl)piperidin-4-oneHCID 727146143-Amino-5-(3,5-dichloroanilino)-s-triazoleHCID 867076002,6-Dichloro-4-isothiocyanatobenzonitrile

Product 1

HCID 178504948N*3*-(3,5-Dichloro-phenyl)-N*5*-(1-methanesulfonyl-piperidin-4-yl)-1H-[1,2,4]triazole-3,5-diamineYield 8%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

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)+

Workup

  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

Sources & evidence

ORD record
ord-35ea24d76d614e88b3802581edf5bb1a
Source dataset
uspto-grants-2016_08
Patent number
US09428469B2

Reaction notes

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