Water → HCID 178507844, compound

HRID 274983Notes

Reaction equation

HRID 274983 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:32]=[CH:31][C:27]3[NH:28][CH:29]=[N:30][C:26]=3[CH:25]=2)[C:14]([N:16]2[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]2)=[O:15])(=[O:11])=[O:10])=[CH:4][C:3]=1[Cl:33].[BH4-].[Na+].O>CN(C)C=O>[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:32]=[CH:31][C:27]3[NH:28][CH:29]=[N:30][C:26]=3[CH:25]=2)[C:14]([N:16]2[CH2:17][CH2:18][CH:19]([OH:22])[CH2:20][CH2:21]2)=[O:15])(=[O:10])=[O:11])=[CH:4][C:3]=1[Cl:33]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 178507843HCID 178507843, compound

Product 1

HCID 178507844HCID 178507844, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

410 mg (0.8 mMol) of 4-amino-N-[1-(1H-benzimidazol-5-yl-methyl)-2-(piperidin-4-on-1-yl]-2-oxo-ethyl]-3,5-dichloro-benzenesulphonamide are dissolved in 8 ml of absolute dimethylformamide, mixed with 100 mg (2.6 mMol) of sodium borohydride and left to stand for 12 hours at ambient temperature. Then the reaction mixture is poured into water and extracted 3 times with ethyl acetate. The organic phase is washed twice with water, dried with sodium sulphate and evaporated down. The residue is purified over a silica gel column, the evaporated eluate is triturated with ether and suction filtered.

Workup

  1. waitleft
  2. extractionextracted 3 times with ethyl acetate
  3. washThe organic phase is washed twice with water
  4. dry with materialdried with sodium sulphate
  5. customevaporated down
  6. customThe residue is purified over a silica gel column
  7. customthe evaporated eluate is triturated with ether and suction
  8. filtrationfiltered

Sources & evidence

ORD record
ord-c254e35f55eb4c1487105a5ec823f0e1
Source dataset
uspto-grants-1995_02
Patent number
US05391556

Reaction notes

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