Quipazine → Methyl 2-chloro-6-[5-(4-quinolin-2-ylpiperazin-1-yl)pentanoylamino]benzoate

HRID 1714793Notes

Reaction equation

HRID 1714793 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([NH:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:10]=1[C:11]([O:13][CH3:14])=[O:12])=[O:7].[N:20]1([C:26]2[CH:35]=[CH:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]=2)[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[Cl:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:9]([NH:8][C:6](=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2][N:23]2[CH2:24][CH2:25][N:20]([C:26]3[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[N:27]=3)[CH2:21][CH2:22]2)[C:10]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 3

HCID 5011QuipazineHCID 8471TriethylamineHCID 23155867Methyl 2-(5-bromopentanoylamino)-6-chlorobenzoate

Product 1

HCID 23155741Methyl 2-chloro-6-[5-(4-quinolin-2-ylpiperazin-1-yl)pentanoylamino]benzoateYield 64%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1.29 g of methyl 2-(5-bromopentanoylamino)-6-chloro-benzoate as synthesized in above Step 7-18-B, 800 mg of 2-piperazin-1-ylquinoline as synthesized in Step 7-1-A, 400 mg of triethylamine and 20 ml of toluene was heated under reflux for 3 hours. After cooling, the solution was washed with water, dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified on silica gel column chromatography (ethyl acetate:methanol=15:1) to provide 1.13 g (64%) of methyl 2-chloro-6-[5-(4-quinolin-2-ylpiperazin-1-yl)pentanoylamino]benzoate.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. temperatureAfter cooling
  4. washthe solution was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified on silica gel column chromatography (ethyl acetate:methanol=15:1)

Sources & evidence

ORD record
ord-c466439beef046a298ab8013f29e7066
Source dataset
uspto-grants-2010_09
Patent number
US07799775B2

Reaction notes

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