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2-Butanamine, 2-methyl- → 6,7-dichloro-2,3-dimethoxy-5-{[2-(N-(1,1-dimethylpropyl)amino)ethyl]pyrazol-1-ylmethyl}quinoxaline

HRID 1957114
Notes
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Reaction equation

HRID 1957114 reaction equation
Cl[CH2:2][CH2:3][CH:4]([N:21]1[CH:25]=[CH:24][CH:23]=[N:22]1)[C:5]1[C:14]([Cl:15])=[C:13]([Cl:16])[CH:12]=[C:11]2[C:6]=1[N:7]=[C:8]([O:19][CH3:20])[C:9]([O:17][CH3:18])=[N:10]2.[CH3:26][C:27]([NH2:31])([CH3:30])[CH2:28][CH3:29]>C(O)C>[Cl:15][C:14]1[C:5]([CH:4]([CH2:3][CH2:2][NH:31][C:27]([CH3:30])([CH3:26])[CH2:28][CH3:29])[N:21]2[CH:25]=[CH:24][CH:23]=[N:22]2)=[C:6]2[C:11](=[CH:12][C:13]=1[Cl:16])[N:10]=[C:9]([O:17][CH3:18])[C:8]([O:19][CH3:20])=[N:7]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 689862-Butanamine, 2-methyl-HCID 543391965-[(2-Chloroethyl)pyrazol-1-ylmethyl]-6,7-dichloro-2,3-dimethoxyquinoxaline

Product 1

HCID 232249886,7-dichloro-2,3-dimethoxy-5-{[2-(N-(1,1-dimethylpropyl)amino)ethyl]pyrazol-1-ylmethyl}quinoxalineYield 38%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 5-[(2-chloroethyl)pyrazol-1-ylmethyl]-6,7-dichloro-2,3-dimethoxyquinoxaline (150 mg, 0.37 mmol), 1,1-dimethyl-1-propylamine (3 mL) and ethanol (5 mL) were heated in a closed vessel at 105° C. for 7 hours. The mixture was cooled, the solvent was removed under reduced pressure, and the residue was dissolved in ethyl acetate (75 mL). The solution was washed with saturated aqueous sodium bicarbonate, dried (MgSO4) and concentrated under reduced pressure. Purification by flash chromatography (elution with dichloromethane, then an ethyl acetate/methanol/triethylamine gradient) gave 6,7-dichloro-2,3-dimethoxy-5-{[2-(N-(1,1-dimethylpropyl)amino)ethyl]pyrazol-1-ylmethyl}quinoxaline (65 mg, 38%), as a pale yellow solid.

Workup

  1. temperatureThe mixture was cooled
  2. customthe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate (75 mL)
  4. washThe solution was washed with saturated aqueous sodium bicarbonate
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash chromatography (
  8. washelution with dichloromethane

Sources & evidence

ORD record
ord-7e8695b6787e4c51a6b28f32700ac456
Source dataset
uspto-grants-1998_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05783572

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes