Acetic Anhydride → HCID 9892613, compound

HRID 1244434Notes

Reaction equation

HRID 1244434 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([CH2:17][CH:18]([NH:28][OH:29])[CH2:19][CH2:20][CH2:21][C:22]3[N:27]=[CH:26][CH:25]=[CH:24][N:23]=3)(=[O:16])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:30](OC(=O)C)(=[O:32])C>C1COCC1.C(O)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:9][CH2:10][N:11]([S:14]([CH2:17][CH:18]([N:28]([OH:29])[CH:30]=[O:32])[CH2:19][CH2:20][CH2:21][C:22]3[N:27]=[CH:26][CH:25]=[CH:24][N:23]=3)(=[O:15])=[O:16])[CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 21919399HCID 21919399, compound

Product 1

HCID 9892613HCID 9892613, compoundYield 51.1%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of N-[1-([4-(4-bromophenyl)piperazino]sulfonylmethyl)-4-pyrimidin-2-ylbutyl]hydroxylamine (497 mg, 1.0 mmol) in THF (5.0 ml) and formic acid (2.5 ml), cooled to 0° C., was added a preformed mixture of acetic anhydride (566 μl, 6.0 mmol) and formic acid (2.0 ml). The mixture was stirred at 0° C. for 1 hour and allowed to come to room temperature. The solvents were removed by rotary evaporation and the residue purified by chromatography (50 g Silica Bond Elute, eluent 0→15% Methanol/Dichloromethane), pure fractions evaporated, and crystallised from hot ethyl acetate to give N-[1-([4-(4-bromophenyl)piperazino]sulfonylmethyl)-4-pyrimidin-2-ylbutyl]-N-hydroxyformamide as a white crystalline powder (262 mg, 51%).

Workup

  1. additionwas added
  2. customto come to room temperature
  3. customThe solvents were removed by rotary evaporation
  4. customthe residue purified by chromatography (50 g Silica Bond Elute, eluent 0→15% Methanol/Dichloromethane), pure fractions
  5. customevaporated
  6. customcrystallised from hot ethyl acetate

Sources & evidence

ORD record
ord-6ab73ad7e4664ead9025c2dc48673b33
Source dataset
uspto-grants-2006_10
Patent number
US07122551B2

Reaction notes

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