Triethylamine → HCID 21912961, compound

HRID 1352537Notes

Reaction equation

HRID 1352537 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[C:14]([NH:15][C:16](=O)[CH2:17][CH2:18][CH2:19][CH3:20])=[C:13]([NH:22][CH2:23][CH2:24][O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:12]([CH3:32])=[C:11]([CH3:33])[N:10]=1>C(O)C>[CH2:17]([C:16]1[N:22]([CH2:23][CH2:24][O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:13]2[C:12]([CH3:32])=[C:11]([CH3:33])[N:10]=[C:9]([Cl:8])[C:14]=2[N:15]=1)[CH2:18][CH2:19][CH3:20]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 21913341HCID 21913341, compound

Product 1

HCID 21912961HCID 21912961, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Triethylamine (1.93 ml), anhydrous ethanol (35 ml), and N-{2-chloro-5,6-dimethyl-4-[(2-phenoxyethyl)amino]pyridin-3-yl}pentanamide (1.32 g) from Part A were combined and heated to reflux for 24 hours. The reaction stalled, so the mixture was cooled and the solvent was removed under reduced pressure. Pyridine (75 ml) and an equivalent of pyridine HCl was added and the reaction mixture was heated to reflux for 16 hours. TLC analysis indicated that the reaction was complete. The reaction was allowed to cool and the solvent was removed under reduced pressure. The resulting product was dissolved in ethyl acetate and washed 4 times with water (150 ml each) to remove the pyridine HCl. The organic layer was dried with magnesium sulfate and the solvent was removed under reduced pressure. NMR analysis of the dried brown solid indicated sufficient purity for use of the product in the next step.

Workup

  1. temperatureheated
  2. temperatureto reflux for 24 hours
  3. temperaturewas cooled
  4. customthe solvent was removed under reduced pressure
  5. additionPyridine (75 ml) and an equivalent of pyridine HCl was added
  6. temperaturethe reaction mixture was heated
  7. temperatureto reflux for 16 hours
  8. temperatureto cool
  9. customthe solvent was removed under reduced pressure
  10. dissolutionThe resulting product was dissolved in ethyl acetate
  11. washwashed 4 times with water (150 ml each)
  12. customto remove the pyridine HCl
  13. dry with materialThe organic layer was dried with magnesium sulfate
  14. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-802c98e7dec640d9af27086c57530170
Source dataset
uspto-grants-2007_05
Patent number
US07220758B2

Reaction notes

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