Cyclopropanecarbonyl chloride → HCID 11993094, compound

HRID 421839Notes

Reaction equation

HRID 421839 reaction equation
[NH2:1][C:2](=[N:23][OH:24])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([N:9]2[CH2:14][CH2:13][N:12]([C:15](=[O:22])[CH2:16][CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:11][CH2:10]2)[CH:4]=1.[CH:25]1([C:28](Cl)=O)[CH2:27][CH2:26]1>N1C=CC=CC=1.C(OCC)(=O)C>[CH3:19][C:18]([CH3:20])([CH3:21])[CH2:17][CH2:16][C:15]([N:12]1[CH2:13][CH2:14][N:9]([C:5]2[CH:4]=[C:3]([C:2]3[N:1]=[C:28]([CH:25]4[CH2:27][CH2:26]4)[O:24][N:23]=3)[CH:8]=[CH:7][N:6]=2)[CH2:10][CH2:11]1)=[O:22]

Participants

5

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 136381719HCID 136381719, compound

Product 1

HCID 11993094HCID 11993094, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-{4-[Amino(hydroxyimino)methyl]pyridin-2-yl}-4-(4,4-dimethylpentanoyl)piperazine (235 mg) obtained in Example 56-1) was dissolved in pyridine (1 mL), then cyclopropanecarbonyl chloride (0.065 mL) was added thereto and heated under reflux for 90 minutes. The reaction liquid was diluted with ethyl acetate, washed with water, aqueous saturated sodium hydrogencarbonate solution and saturated saline water, and dried with anhydrous sodium sulfate. The solvent was evaporated away, and the resulting residue was isolated and purified through thin-layer silica gel chromatography (hexane/ethyl acetate=1/1) to obtain 187 mg of the entitled compound as a colorless solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 90 minutes
  3. customThe reaction liquid
  4. washwashed with water, aqueous saturated sodium hydrogencarbonate solution and saturated saline water
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe solvent was evaporated away
  7. customthe resulting residue was isolated
  8. custompurified through thin-layer silica gel chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-357fd160cc434fdfa6fb059e8ea043ee
Source dataset
uspto-grants-2012_01
Patent number
US08101618B2

Reaction notes

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