Ammonia → 5-[({[3'-(aminomethyl)biphenyl-4-yl]methyl}sulfonyl)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 606517Notes

Reaction equation

HRID 606517 reaction equation
[O:1]=[C:2]1[NH:6][N:5]=[C:4]([CH2:7][S:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]#[N:25])[CH:19]=3)=[CH:14][CH:13]=2)(=[O:10])=[O:9])[NH:3]1.N.CO>C1COCC1.[Ni]>[NH2:25][CH2:24][C:20]1[CH:19]=[C:18]([C:15]2[CH:16]=[CH:17][C:12]([CH2:11][S:8]([CH2:7][C:4]3[NH:3][C:2](=[O:1])[NH:6][N:5]=3)(=[O:9])=[O:10])=[CH:13][CH:14]=2)[CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 1360545044'-({[(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl]sulfonyl}methyl)biphenyl-3-carbonitrile

Product 1

HCID 1360544705-[({[3'-(aminomethyl)biphenyl-4-yl]methyl}sulfonyl)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-oneYield 99%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 4′-({[(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl]sulfonyl}methyl)biphenyl-3-carbonitrile obtained in Reference Example 110 (0.250 g, 0.705 mmol), Raney-nickel (0.250 g) and 28% aqueous ammonia (5 mL) in THF (5 mL)-methanol (5 mL) was stirred at room temperature for 4 hr under hydrogen atmosphere (1 atm). The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. Diethyl ether was added to the residue, and the precipitated solid was collected by filtration to give the title compound as a pale-blue powder (0.250 g, 99%).

Workup

  1. filtrationThe insoluble material was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionDiethyl ether was added to the residue
  4. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-4240a1ad37f94f2c89ec042cc0a05d8a
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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