Formic Acid → HCID 178428650, compound

HRID 274958Notes

Reaction equation

HRID 274958 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([S:9]([NH:12][CH:13]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([NH2:30])=[C:26]([N+:31]([O-])=O)[CH:25]=2)[C:14]([N:16]2[CH2:21][CH2:20][CH:19]([CH3:22])[CH2:18][CH2:17]2)=[O:15])(=[O:11])=[O:10])=[CH:4][C:3]=1[Cl:34].[CH:35](O)=O>[Pd]>[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([S:9]([NH:12][CH:13]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]3[NH:30][CH:35]=[N:31][C:26]=3[CH:25]=2)[C:14]([N:16]2[CH2:21][CH2:20][CH:19]([CH3:22])[CH2:18][CH2:17]2)=[O:15])(=[O:11])=[O:10])=[CH:4][C:3]=1[Cl:34]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 200890424-Amino-N-[1-((4-amino-3-nitro-phenyl)-methyl)-2-(4-methyl-piperidin-1-yl)-2-oxo-ethyl]-3,5-dichlorobenzenesulphonamide

Product 1

HCID 178428650HCID 178428650, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
50 °C

Procedure

1.06 g (2 mMol) of 4-amino-N-[1-((4-amino-3-nitro-phenyl)methyl)-2-(4-methyl-piperidin-1-yl)-2-oxo-ethyl]-3,5-dichloro-benzenesulphonamide are suspended in 20 ml of formic acid and hydrogenated, with the addition of 0.1 g palladium/charcoal, in an autoclave under a hydrogen pressure of 5 bar at ambient temperature for 80 minutes. Then the catalyst is filtered off and the filtrate is heated to 50° C. for 2 hours. It is then concentrated by evaporation, mixed with 30 ml of water, made alkaline with concentrated ammonia and extracted twice with ethyl acetate. The organic phase is washed twice with water, dried over magnesium sulphate and evaporated down. The residue obtained is purified on a silica gel column (ethyl acetate/methanol/ammonia=95:5:0.5). After evaporation the residue is recrystallised from isopropanol.

Workup

  1. filtrationThen the catalyst is filtered off
  2. concentrationIt is then concentrated by evaporation
  3. additionmixed with 30 ml of water
  4. extractionextracted twice with ethyl acetate
  5. washThe organic phase is washed twice with water
  6. dry with materialdried over magnesium sulphate
  7. customevaporated down
  8. customThe residue obtained
  9. customis purified on a silica gel column (ethyl acetate/methanol/ammonia=95:5:0.5)
  10. customAfter evaporation the residue
  11. customis recrystallised from isopropanol

Sources & evidence

ORD record
ord-498bf6ece9194d52b1af1837e2702f9d
Source dataset
uspto-grants-1995_02
Patent number
US05391556

Reaction notes

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