Trichloroacetyl chloride → HCID 21190286, compound

HRID 619434Notes

Reaction equation

HRID 619434 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][S:18]([C:21]([F:24])([F:23])[F:22])(=[O:20])=[O:19])[N:5]2[CH:32]=1.[Cl:33][C:34]([Cl:39])([Cl:38])[C:35](Cl)=[O:36].[C:40](=O)([O-])O.[Na+]>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[CH2:1]([C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]([C:25]([O:27][C:28]([CH3:29])([CH3:31])[CH3:30])=[O:26])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][S:18]([C:21]([F:22])([F:23])[F:24])(=[O:19])=[O:20])[N:5]2[C:32]=1[C:35](=[O:36])[C:34]([Cl:39])([Cl:38])[Cl:33])[CH3:40]

Participants

6

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 21190290HCID 21190290, compound

Product 1

HCID 21190286HCID 21190286, compoundYield 55.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 2.85 g (5.79 mmol) of 2-methyl-5-[N-tert-butoxycarbonyl-N-[5-(trifluoromethane-sulfonamido)pentan-1-yl]aminomethyl]imidazo[1,2-a]pyridine and 3.53 g (28.93 mmol) of 4-dimethylaminopyridine in 35 ml of chloroform was added dropwise, for 3 minutes under stirring at room temperature, 3.2 ml (28.93 mmol) of trichloroacetyl chloride. The reaction mixture was heated for 20 hours under reflux. After completion of the reaction, the reaction mixture was poured into ice-water, which was neutralized with a saturated aqueous solution of sodium hydrogencarbonate, followed by extraction with 100 ml of chloroform. The organic layer was washed with 200 ml of a saturated aqueous saline solution, which was dried over magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was purified by silicagel column chromatography (eluent: chloroform/methanol=100:1) to give 2.04 g of the desired compound (55.2%, pale yellow liquid).

Workup

  1. temperatureThe reaction mixture was heated for 20 hours
  2. temperatureunder reflux
  3. customAfter completion of the reaction
  4. extractionfollowed by extraction with 100 ml of chloroform
  5. washThe organic layer was washed with 200 ml of a saturated aqueous saline solution, which
  6. dry with materialwas dried over magnesium sulfate
  7. distillationby distilling off the solvent under reduced pressure
  8. customThe residue was purified by silicagel column chromatography (eluent: chloroform/methanol=100:1)

Sources & evidence

ORD record
ord-f28d21d7f34a4748845c876fbc176f73
Source dataset
uspto-grants-1999_09
Patent number
US05958942

Reaction notes

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