Formic Acid → HCID 22719697, compound

HRID 1582067Notes

Reaction equation

HRID 1582067 reaction equation
C(O[C:5](=[O:7])C)(=O)C.C(O)=O.[Cl:11][C:12]1[N:17]=[CH:16][N:15]=[C:14]([N:18]2[CH2:23][CH2:22][N:21]([S:24]([CH2:27][CH:28]([NH:37][OH:38])[CH2:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)(=[O:26])=[O:25])[CH2:20][CH2:19]2)[CH:13]=1>O1CCCC1>[Cl:11][C:12]1[N:17]=[CH:16][N:15]=[C:14]([N:18]2[CH2:19][CH2:20][N:21]([S:24]([CH2:27][CH:28]([N:37]([OH:38])[CH:5]=[O:7])[CH2:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)(=[O:26])=[O:25])[CH2:22][CH2:23]2)[CH:13]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 22719688HCID 22719688, compound

Product 1

HCID 22719697HCID 22719697, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetic anhydride (19 ml) was added directly to formic acid (76 ml). The solution was stirred at room temperature for 30 minutes. A solution of 1-(6-chloropyrimidin-4-yl)-4-{[2-(hydroxyamino)-4-phenylbutyl]sulphonyl}piperazine (17.2 g) in tetrahydrofuran (85 ml) was added in portions, to the above solution at 27° C. over 25 minutes. The solution was stirred at room temperature for 1 hour. The solution was evaporated (water-bath temperature 30° C.) and the residual gum was dissolved in ethyl acetate (500 ml). This solution was treated with saturated aqueous sodium hydrogen carbonate solution (200 ml) and the mixture (pH8) was stirred at room temperature for 16 hours. The ethyl acetate layer was separated, washed with saturated brine (100 ml), dried (Na2SO4), and evaporated to dryness. The residual foam was dissolved in ethanol, a solid separated and the miixture was stirred for 2 days. The solid was collected by filtration, slurry washed with diethyl ether (100 ml), and dried to give N-[1-({[4-(6-chloropyrimidin-4-yl)piperazino]sulphonyl}methyl)-3-phenylpropyl]-N-hydroxyformamide as a colourless solid (12.8 g). mp 155-157° C.

Workup

  1. stirringThe solution was stirred at room temperature for 1 hour
  2. customThe solution was evaporated (water-bath temperature 30° C.)
  3. dissolutionthe residual gum was dissolved in ethyl acetate (500 ml)
  4. additionThis solution was treated with saturated aqueous sodium hydrogen carbonate solution (200 ml)
  5. stirringthe mixture (pH8) was stirred at room temperature for 16 hours
  6. customThe ethyl acetate layer was separated
  7. washwashed with saturated brine (100 ml)
  8. dry with materialdried (Na2SO4)
  9. customevaporated to dryness
  10. dissolutionThe residual foam was dissolved in ethanol
  11. customa solid separated
  12. stirringthe miixture was stirred for 2 days
  13. filtrationThe solid was collected by filtration, slurry
  14. washwashed with diethyl ether (100 ml)
  15. customdried

Sources & evidence

ORD record
ord-bcd32f46b6ff47158b9b2b72ad29fdce
Source dataset
uspto-grants-2004_05
Patent number
US06734184B1

Reaction notes

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