Triethylamine → HCID 21190188, compound

HRID 619443Notes

Reaction equation

HRID 619443 reaction equation
[I-].C(O[C:5]([C:7]1[N:12]2[CH:13]=[CH:14][N:15]=[C:11]2[C:10](C[N+](C)(C)C)=[CH:9][CH:8]=1)=[O:6])C.[F:21][C:22]([F:33])([F:32])[S:23]([NH:26][CH2:27][CH2:28][CH2:29][CH2:30][NH2:31])(=[O:25])=[O:24].[CH2:34](N(CC)CC)C>C(#N)C>[F:33][C:22]([F:32])([F:21])[S:23]([NH:26][CH2:27][CH2:28][CH2:29][CH2:30][N:31]1[C:5](=[O:6])[C:7]2[N:12]3[C:13](=[CH:14][N:15]=[C:11]3[CH:10]=[CH:9][CH:8]=2)[CH2:34]1)(=[O:24])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11276038HCID 11276038, compoundHCID 86584076HCID 86584076, compound

Product 1

HCID 21190188HCID 21190188, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 778 mg (2.0 mmol) of 5-ethoxycarbonylimidazo[1,2-a]pyridin-8-ylmethyl trimethylammonium iodide, 616 mg (2.4 mmol) of 4-trifluoromethanesulfonamido-1-butylamine and 1.12 ml (8.0 mmol) of triethylamine in 40 ml of acetonitrile was heated for 14 hours under reflux. The solvent was distilled off. To the residue was added chloroform, and washed with water. The aqueous layer was further extracted with chloroform. The chloroform layers were combined, and dried over anhydrous magnesium sulfate. The solvent was distilled off. The residue was crystallized from chloroform. The crystalline product was collected by filtration, washed with chloroform and dried to afford 141 mg (18.8%, colorless crystals) of the desired compound.

Workup

  1. temperatureunder reflux
  2. distillationThe solvent was distilled off
  3. additionTo the residue was added chloroform
  4. washwashed with water
  5. extractionThe aqueous layer was further extracted with chloroform
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off
  8. customThe residue was crystallized from chloroform
  9. filtrationThe crystalline product was collected by filtration
  10. washwashed with chloroform
  11. customdried

Sources & evidence

ORD record
ord-fc88e62cb71b4079a698b2a2b31bcaeb
Source dataset
uspto-grants-1999_09
Patent number
US05958942

Reaction notes

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