Trichloroacetyl chloride → HCID 21190229, compound

HRID 1068761Notes

Reaction equation

HRID 1068761 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:23][C:24]1[N:29]2[CH:30]=[CH:31][N:32]=[C:28]2[CH:27]=[CH:26][CH:25]=1)[CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:22])[C:15]([F:21])([F:20])[C:16]([F:19])([F:18])[F:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:33][C:34]([Cl:39])([Cl:38])[C:35](Cl)=[O:36]>CN(C1C=CN=CC=1)C.C(Cl)(Cl)Cl>[Cl:33][C:34]([Cl:39])([Cl:38])[C:35]([C:30]1[N:29]2[C:24]([CH2:23][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:22])[C:15]([F:21])([F:20])[C:16]([F:19])([F:17])[F:18])=[CH:25][CH:26]=[CH:27][C:28]2=[N:32][CH:31]=1)=[O:36]

Participants

5

Reactant 2

HCID 6420Trichloroacetyl chlorideHCID 21190182HCID 21190182, compound

Product 1

HCID 21190229HCID 21190229, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 11.78 g (25.36 mmol) of 5-[N-tert-butoxycarbonyl-N-(4-pentafluoropropionamidobutan-1-yl)aminomethyl]imidazo[1,2-a]pyridine and 13.94 g (114.36 mmol) of 4-(N,N-dimethylamino)pyridine in 250 ml of chloroform was added 8.50 ml (76.09 mmol) of trichloroacetyl chloride. The mixture was heated for 16 hours under reflux. The reaction mixture was poured into ice-water, and extracted with 100 ml of chloroform. The organic layer was washed with 200 ml of a saturated aqueous saline solution, dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform) to afford 6.80 g of the desired compound (44.0%, a pale yellow liquid).

Workup

  1. temperatureThe mixture was heated for 16 hours
  2. temperatureunder reflux
  3. extractionextracted with 100 ml of chloroform
  4. washThe organic layer was washed with 200 ml of a saturated aqueous saline solution
  5. dry with materialdried over magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: chloroform)

Sources & evidence

ORD record
ord-785eeb46b7334f77b7509d7ea02c43a8
Source dataset
uspto-grants-2001_06
Patent number
US06251905B1

Reaction notes

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