N-[6-(Cyanomethyl)-3-pyridinyl]-4-(1-methylethyl)benzenesulfonamide → HCID 67420415, compound

HRID 1518197Notes

Reaction equation

HRID 1518197 reaction equation
[C:1]([CH2:3][C:4]1[N:9]=[CH:8][C:7]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH:20]([CH3:22])[CH3:21])=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:6][CH:5]=1)#[N:2]>C(O)C.[Ni]>[NH2:2][CH2:1][CH2:3][C:4]1[N:9]=[CH:8][C:7]([NH:10][S:11]([C:14]2[CH:15]=[CH:16][C:17]([CH:20]([CH3:22])[CH3:21])=[CH:18][CH:19]=2)(=[O:13])=[O:12])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 67419651N-[6-(Cyanomethyl)-3-pyridinyl]-4-(1-methylethyl)benzenesulfonamide

Product 1

HCID 67420415HCID 67420415, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of N-(6-cyanomethyl-pyridin-3-yl)-4-isopropyl-benzenesulfonamide (1.7 g, 5.4 mmol) aqueous ammonia (45 ml) and raney-nickel (2.7 mmol) in ethanol (50 ml) was hydrogenated at atmospheric pressure. After filtration the mixture was concentrated under reduced pressure. The residue was partitioned between ethyl acetate and saturated aqueous NaHCO3 and the aqueous layer extracted five times with ethyl acetate. The combined organic layers were dried over MgSO4, filtered, and the solvent evaporated under reduced pressure to give the product as a yellow powder after recrystallisation from methanol/ethyl acetate (1.3 g, 73%).

Workup

  1. filtrationAfter filtration the mixture
  2. concentrationwas concentrated under reduced pressure
  3. customThe residue was partitioned between ethyl acetate and saturated aqueous NaHCO3
  4. extractionthe aqueous layer extracted five times with ethyl acetate
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-00fd3fb316d546b6aff95c6c290da6be
Source dataset
uspto-grants-2012_07
Patent number
US08232426B2

Reaction notes

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