Formic Acid → HCID 10227239, compound

HRID 1244438Notes

Reaction equation

HRID 1244438 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:38][OH:39])[CH2:29][CH2:30][C:31]3[N:36]=[CH:35][C:34]([F:37])=[CH:33][N:32]=3)(=[O:26])=[O:25])[CH2:20][CH2:19]2)=[N:16][CH:17]=1>O1CCCC1>[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:38]([OH:39])[CH:5]=[O:7])[CH2:29][CH2:30][C:31]3[N:36]=[CH:35][C:34]([F:37])=[CH:33][N:32]=3)(=[O:25])=[O:26])[CH2:22][CH2:23]2)=[N:16][CH:17]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 21919395HCID 21919395, compound

Product 1

HCID 10227239HCID 10227239, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Acetic anhydride (0.51 ml) was added directly to formic acid (2.0 ml) which had been cooled to 0° C. and then added a solution of 2-[4-[4-(5-chloropyridin-2-yl)piperazino]sulfonyl-3-(hydroxyamino)butyl]-5-fluoropyrimidine (0.485 g) in tetrahydrofuran (11 ml). The solution was stirred at room temperature for 3 hours and then evaporated in vacuo, the resulting residue was azeotroped with toluene and then it was dissolved in methanol and heated to 40° C. for 30 minutes. The solution was evaporated to dryness and then added diethylether and stirred at room temperature for 10 minutes, solid filtered, dried in vacuo to give N-[1-([4-(5-chloropyridin-2-yl)piperazino]sulfonylmethyl)-3-(5-fluoropyrimidin-2-yl)propyl]-N-hydroxyformamide, (0218 g), mp 154–155° C.

Workup

  1. customevaporated in vacuo
  2. customthe resulting residue was azeotroped with toluene
  3. dissolutionit was dissolved in methanol
  4. temperatureheated to 40° C. for 30 minutes
  5. customThe solution was evaporated to dryness
  6. stirringadded diethylether and stirred at room temperature for 10 minutes
  7. filtrationsolid filtered
  8. customdried in vacuo

Sources & evidence

ORD record
ord-dd5360423014474aa65c222ac6c23e23
Source dataset
uspto-grants-2006_10
Patent number
US07122551B2

Reaction notes

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