Formic Acid → HCID 9935464, compound

HRID 1582062Notes

Reaction equation

HRID 1582062 reaction equation
C(O[C:5](=[O:7])C)(=O)C.C(O)=O.[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([N:18]2[CH2:23][CH2:22][N:21]([S:24]([CH2:27][CH:28]([NH:37][OH:38])[C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([Cl:36])[CH:30]=3)(=[O:26])=[O:25])[CH2:20][CH2:19]2)=[N:16][CH:17]=1.C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([N:18]2[CH2:19][CH2:20][N:21]([S:24]([CH2:27][CH:28]([N:37]([OH:38])[CH:5]=[O:7])[C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([Cl:36])[CH:30]=3)(=[O:26])=[O:25])[CH2:22][CH2:23]2)=[N:16][CH:17]=1

Participants

7

Reactant 4

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 22719717HCID 22719717, compound

Product 1

HCID 9935464HCID 9935464, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

Acetic anhydride (0.63 ml) was added directly to formic acid (2.48 ml). The solution was stirred at room temperature for 30 minutes and then added a solution of N-[2-{[4-(5-chloropyridin-2-yl)piperazino]sulfonyl}-1-(3,4-dichlorophenyl)ethyl]hydroxylamine (0.6 g) in tetrahydrofuran (10 ml). The solution was stirred at room temperature for 3 hours and then diluted with ethyl acetate, neutralised the pH with saturated aqueous sodium hydrogen carbonate solution The ethyl acetate layer was separated, dried (Na2SO4), and evaporated to dryness. The residue was purified by chromatography using a 10 g silica isolute eluting with 10% ethyl acetate/heaxane—80% ethyl acetate/hexane and then evaporated to dryness. The resulting white solid was filtered from diethyl ether to give N-[2-{[4-(5-chloropyridin-2-yl)piperazino]sulfonyl}-1-(3,4-dichlorophenyl)ethyl]-N-hydroxyformamide (0.43 1 g), 211-212° C.

Workup

  1. stirringThe solution was stirred at room temperature for 3 hours
  2. customwas separated
  3. dry with materialdried (Na2SO4)
  4. customevaporated to dryness
  5. customThe residue was purified by chromatography
  6. washisolute eluting with 10% ethyl acetate/heaxane—80% ethyl acetate/hexane
  7. customevaporated to dryness
  8. filtrationThe resulting white solid was filtered from diethyl ether

Sources & evidence

ORD record
ord-a53d17e3d7b64367b70a35de831dce6d
Source dataset
uspto-grants-2004_05
Patent number
US06734184B1

Reaction notes

Loading…