Ethanol → (rac) 3-[6-(4-Chlorophenoxy)-1-methyl-hexylamino]-4-(pyridin-3-yl-amino)-cyclobut-3-ene-1,2-dione

HRID 2097335Notes

Reaction equation

HRID 2097335 reaction equation
C(O[C:4]1[C:5](=[O:16])[C:6](=[O:15])[C:7]=1[NH:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)C.[Cl:17][C:18]1[CH:32]=[CH:31][C:21]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]([NH2:30])[CH3:29])=[CH:20][CH:19]=1.CCO.CC#N>C(O)(C(F)(F)F)=O>[Cl:17][C:18]1[CH:32]=[CH:31][C:21]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]([NH:30][C:4]2[C:5](=[O:16])[C:6](=[O:15])[C:7]=2[NH:8][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[CH3:29])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 6342AcetonitrileHCID 105129913-(Pyridin-3-ylamino)-4-ethoxy-cyclobut-3-ene-1,2-dioneHCID 597815546-(4-Chlorophenoxy)-1-methyl-hexylamine

Product 1

HCID 87612561(rac) 3-[6-(4-Chlorophenoxy)-1-methyl-hexylamino]-4-(pyridin-3-yl-amino)-cyclobut-3-ene-1,2-dioneYield 12%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The title compound was prepared from 3-ethoxy-4-(pyridine-3-yl-amino)-3-cyclobutene-1,2-dione (164 mg, 0.75 mmol) prepared according to example 1A and crude 6-(4-chlorophenoxy)-1-methyl-hexylamine (738 mg) in refluxing EtOH (15 ml). After 36 h the solvent was evaporated and the product was isolated by preparative HPLC chromatography using a gradient of 30 to 50% MeCN in 0.01% aq. TFA and subsequent freeze drying of the product containing fractions.

Workup

  1. customprepared
  2. customAfter 36 h the solvent was evaporated
  3. customthe product was isolated by preparative HPLC chromatography
  4. customdrying of the product
  5. additioncontaining fractions

Sources & evidence

ORD record
ord-4cc0153fa1cb40eb95c6c589e6f899c2
Source dataset
uspto-grants-2013_05
Patent number
US08450348B2

Reaction notes

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