Trichloroacetyl chloride → HCID 21190083, compound

HRID 619486Notes

Reaction equation

HRID 619486 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:25][C:26]1[N:31]2[CH:32]=[CH:33][N:34]=[C:30]2[CH:29]=[CH:28][CH:27]=1)[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][NH:17][S:18]([C:21]([F:24])([F:23])[F:22])(=[O:20])=[O:19])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:35][C:36]([Cl:41])([Cl:40])[C:37](Cl)=[O:38].C(=O)([O-])O.[Na+]>CN(C1C=CN=CC=1)C.C(Cl)(Cl)Cl>[Cl:35][C:36]([Cl:41])([Cl:40])[C:37]([C:32]1[N:31]2[C:26]([CH2:25][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C:9]3[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][NH:17][S:18]([C:21]([F:24])([F:22])[F:23])(=[O:20])=[O:19])=[CH:13][CH:14]=3)=[CH:27][CH:28]=[CH:29][C:30]2=[N:34][CH:33]=1)=[O:38]

Participants

6

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 21190225HCID 21190225, compound

Product 1

HCID 21190083HCID 21190083, compoundYield 54.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 2.00 g of 5-[N-tert-butoxycarbonyl-N-[4-(2-trifluoromethanesulfonamidoethan-1-yl)phenyl] aminomethyl]imidazo[1,2-a]pyridine and 1.47 g (12.04 mmol) of 4-(N,N-dimethylamino)pyridine in 20 ml of chloroform was added dropwise 1.34 ml (12.04 mmol) of trichloroacetyl chloride at room temperature. The reaction mixture was heated for 18 hours under reflux. The reaction mixture was poured into ice-water. The mixture was neutralized with a saturated aqueous solution of sodium hydrogencarbonate, and extracted with 100 ml of chloroform. The organic layer was washed with 100 ml of purified water three times and further with 100 ml of a saturated aqueous saline solution, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform) to afford 1415 mg of the desired compound (54.8%, a yellow liquid).

Workup

  1. temperatureThe reaction mixture was heated for 18 hours
  2. temperatureunder reflux
  3. extractionextracted with 100 ml of chloroform
  4. washThe organic layer was washed with 100 ml of purified water three times and further with 100 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-e358a69371534a30ad6f8c7d565c6c4c
Source dataset
uspto-grants-1999_09
Patent number
US05958942

Reaction notes

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