Trichloroacetyl chloride → HCID 21190140, compound

HRID 619474Notes

Reaction equation

HRID 619474 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:20][C:21]1[N:26]2[CH:27]=[CH:28][N:29]=[C:25]2[CH:24]=[CH:23][CH:22]=1)[CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:30][C:31]([Cl:36])([Cl:35])[C:32](Cl)=[O:33]>CN(C1C=CN=CC=1)C.C1COCC1>[Cl:30][C:31]([Cl:36])([Cl:35])[C:32]([C:27]1[N:26]2[C:21]([CH2:20][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:19])[C:15]([F:18])([F:17])[F:16])=[CH:22][CH:23]=[CH:24][C:25]2=[N:29][CH:28]=1)=[O:33]

Participants

5

Reactant 2

HCID 6420Trichloroacetyl chlorideHCID 21190090HCID 21190090, compound

Product 1

HCID 21190140HCID 21190140, compoundYield 47.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7.69 g (18.56 mmol) of 5-[N-tert-butoxycarbonyl-N-(4-trifluoroacetamidobutan-1-yl)amino methyl]imidazo[1,2-a]pyridine and 10.20 g (83.52 mmol) of 4-(N,N-dimethylamino)pyridine in 100 ml of THF was added 6.21 ml (55.67 mmol) of trichloroacetyl chloride. The reaction mixture was heated for 16 hours under reflux. The reaction mixture was poured into ice-water, and extracted with 100 ml of ethyl acetate. The organic layer was washed with 150 ml of a saturated aqueous saline solution, dried over magnesium sulfate, and distilled off the solvent under reduced pressure. The residue was purified by silica gel column chromatography (eluent; chloroform) to afford 4.98 g of the desired compound (48.0%, a pale yellow amorphous).

Workup

  1. temperatureThe reaction mixture was heated for 16 hours
  2. temperatureunder reflux
  3. extractionextracted with 100 ml of ethyl acetate
  4. washThe organic layer was washed with 150 ml of a saturated aqueous saline solution
  5. dry with materialdried over magnesium sulfate
  6. distillationdistilled off the solvent under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent; chloroform)

Sources & evidence

ORD record
ord-1e25b9e1881344f68f451991b7634520
Source dataset
uspto-grants-1999_09
Patent number
US05958942

Reaction notes

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