Cyclopropanecarbonyl chloride → HCID 11993183, compound

HRID 421841Notes

Reaction equation

HRID 421841 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)[N: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[N: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 136381720HCID 136381720, compound

Product 1

HCID 11993183HCID 11993183, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-{4-[Amino(hydroxyimino)methyl]pyrimidin-2-yl}-4-(4,4-dimethylpentanoyl)piperazine (59.5 mg) was dissolved in pyridine (1 mL), and cyclopropanecarbonyl chloride (0.020 mL) was added thereto and heated under reflux for 3 hours. The reaction liquid was diluted with ethyl acetate, washed with aqueous saturated ammonium chloride solution, 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=3/2) to obtain 31.9 mg of the entitled compound as a colorless solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hours
  3. customThe reaction liquid
  4. washwashed with aqueous saturated ammonium chloride solution, 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=3/2)

Sources & evidence

ORD record
ord-fd533cfe3cd24cb4b4a701df6f2c449d
Source dataset
uspto-grants-2012_01
Patent number
US08101618B2

Reaction notes

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