2-Chlorobenzoyl chloride → HCID 11992995, compound

HRID 2267154Notes

Reaction equation

HRID 2267154 reaction equation
[OH:1][NH:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)=[NH:4].[Cl:18][C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21](Cl)=O>N1C=CC=CC=1.C(OCC)C>[Cl:18][C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21]1[O:1][N:2]=[C:3]([N:5]2[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:10]2)[N:4]=1

Participants

5

Reactant 2

HCID 691102-Chlorobenzoyl chlorideHCID 178452346tert-butyl 4-(N-hydroxyamidino)-piperazine-1-carboxylate

Product 1

HCID 11992995HCID 11992995, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

tert-Butyl 4-(N-hydroxyamidino)-piperazine-1-carboxylate (290 mg) prepared in Example 36 was dissolved in 2 ml of pyridine, 0.20 ml of 2-chlorobenzoyl chloride was added thereto and the mixture was heated to reflux for 1 hour. The reaction solution was diluted with diethyl ether, washed with 1N hydrochloric acid, a saturated aqueous solution of sodium hydrogen carbonate and a saturated saline solution and dried over anhydrous magnesium sulfate. The residue prepared by evaporation of the solvent was purified by a preparative thin-layer silica gel chromatography (hexane:ethyl acetate=7:3) to give 64.0 mg of the title compound as a white solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 hour
  3. washwashed with 1N hydrochloric acid
  4. dry with materiala saturated aqueous solution of sodium hydrogen carbonate and a saturated saline solution and dried over anhydrous magnesium sulfate
  5. customThe residue prepared by evaporation of the solvent
  6. customwas purified by a preparative thin-layer silica gel chromatography (hexane:ethyl acetate=7:3)

Sources & evidence

ORD record
ord-5df2239bd1f64369a62b0d3f2aabcf14
Source dataset
uspto-grants-2010_12
Patent number
US07858800B2

Reaction notes

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