HCID 11065264, compound → HCID 15521428, compound

HRID 843253Notes

Reaction equation

HRID 843253 reaction equation
[CH:1]([C:4]1[N:5]=[C:6]([CH2:9][O:10][C:11]2[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=2)[CH:14]=O)[S:7][CH:8]=1)([CH3:3])[CH3:2].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([NH:29][CH2:30][CH2:31][CH2:32][CH2:33][NH2:34])(=[O:28])=[O:27])=[CH:22][CH:21]=1>C(O)C>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([S:26]([NH:29][CH2:30][CH2:31][CH2:32][CH2:33][NH:34][CH2:14][C:13]2[CH:16]=[CH:17][CH:18]=[C:11]([O:10][CH2:9][C:6]3[S:7][CH:8]=[C:4]([CH:1]([CH3:3])[CH3:2])[N:5]=3)[CH:12]=2)(=[O:27])=[O:28])=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 11065264HCID 11065264, compoundHCID 15521427HCID 15521427, compound

Product 1

HCID 15521428HCID 15521428, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.27 g (8.69 mmol) of 3-[(4-isopropyl-2-thiazolyl)methoxy]benzaldehyde and 2.27 g (8.69 mmol) of 4-(4-chlorophenylsulfonylamino)butanamine were dissolved in 150 ml of ethanol and refluxed together with 4.0 g of molecular sieves 3A for 16 hours. The molecular sieves 3A was filtered out, and the filtrate was stirred together with 873 mg of sodium borohydride at room temperature for 3 hours. The reaction solution was evaporated in vacuo for removal of ethanol as the solvent and mixed with water and ethyl acetate for ethyl acetate extraction. The ethyl acetate layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo for removal of the solvent. The residue was purified by silica gel column chromatography (eluent; chloroform to chloroform:methanol=98:2) to give N-[4-(4-chlorobenzenesulfonylamino)butyl]-3-[(4-isopropyl-2-thiazolyl)methoxy]benzylamine (Compound No.1a).

Workup

  1. filtrationThe molecular sieves 3A was filtered out
  2. customThe reaction solution was evaporated in vacuo for removal of ethanol as the solvent
  3. additionmixed with water and ethyl acetate for ethyl acetate extraction
  4. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo for removal of the solvent
  7. customThe residue was purified by silica gel column chromatography (eluent; chloroform to chloroform:methanol=98:2)

Sources & evidence

ORD record
ord-0d6fb30735e540309c35130abc9fcbfe
Source dataset
uspto-grants-2002_04
Patent number
US06376671B1

Reaction notes

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