Hydrochloric Acid → HCID 11202388, compound

HRID 2217811Notes

Reaction equation

HRID 2217811 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:22])[C:8]=2[NH:12][C:13](=[O:21])[CH2:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[NH2:29][CH2:30][CH2:31][NH:32][CH2:33][CH2:34][OH:35].[ClH:36]>CN1CCCC1=O.ClCCl.CO.O1CCOCC1.O>[ClH:1].[ClH:36].[Cl:22][C:7]1[C:8]([NH:12][C:13](=[O:21])[CH2:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([NH:29][CH2:30][CH2:31][NH:32][CH2:33][CH2:34][OH:35])[CH:11]=[CH:10]2

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 8112N-(2-Hydroxyethyl)ethylenediamineHCID 11430Potassium CarbonateHCID 86012996N-(2,6-Dichloro-5-quinolinyl)-cyclohexaneacetamide

Product 1

HCID 11202388HCID 11202388, compound

Reagents, catalysts & solvents 5

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of N-(2,6-dichloro-5-quinolinyl)-cyclohexaneacetamide (Example 1 (a)) (170 mg) and potassium carbonate (350 mg) in N-methylpyrrolidinone (4 mL) was added 2-[(2-aminoethyl)amino]-ethanol (500 μL). The mixture was heated at 120° C. for 5 hours after which it was cooled and poured into water. The resulting solid was isolated by filtration, dried and suspended in dichloromethane (5 mL). The suspension was then treated with di-tert-butyl dicarbonate (220 mg) and triethylamine (200 μL) and stirred for 2 hours. The mixture was poured into water and extracted with dichloromethane (3×20 mL). The combined organic layers were dried, filtered and concentrated. Purification (SiO2, methanol:dichloromethane solution 2.5:97.5 as eluant) yielded the desired isomer which was then dissolved in dichloromethane (5 mL) and methanol (0.5 mL), and treated with hydrochloric acid in 1,4-dioxane (4M, 1 mL) for 1 hour. The resultant suspension was evaporated to dryness and recrystallised from methanol/ethyl acetate to give the title compound as a colourless solid (65 mg).

Workup

  1. temperaturewas cooled
  2. customThe resulting solid was isolated by filtration
  3. customdried
  4. additionThe suspension was then treated with di-tert-butyl dicarbonate (220 mg) and triethylamine (200 μL)
  5. additionThe mixture was poured into water
  6. extractionextracted with dichloromethane (3×20 mL)
  7. customThe combined organic layers were dried
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification (SiO2, methanol:dichloromethane solution 2.5:97.5 as eluant)
  11. customyielded the desired isomer which
  12. customThe resultant suspension was evaporated to dryness
  13. customrecrystallised from methanol/ethyl acetate

Sources & evidence

ORD record
ord-86f18a18045d4951a5e44088b7dc4d50
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

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