Trichloroacetyl chloride → HCID 21190277, compound

HRID 1068711Notes

Reaction equation

HRID 1068711 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:22][C:23]1[N:28]2[CH:29]=[CH:30][N:31]=[C:27]2[CH:26]=[CH:25][CH:24]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][S:15]([C:18]([F:21])([F:20])[F:19])(=[O:17])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:32][C:33]([Cl:38])([Cl:37])[C:34](Cl)=[O:35].C(=O)([O-])O.[Na+]>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[Cl:32][C:33]([Cl:38])([Cl:37])[C:34]([C:29]1[N:28]2[C:23]([CH2:22][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][S:15]([C:18]([F:20])([F:19])[F:21])(=[O:17])=[O:16])=[CH:24][CH:25]=[CH:26][C:27]2=[N:31][CH:30]=1)=[O:35]

Participants

6

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 21190097HCID 21190097, compound

Product 1

HCID 21190277HCID 21190277, compoundYield 58.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 3.55 g (7.64 mmol) of 5-[N-tert-butoxycarbonyl-N-[5-(trifluoromethanesulfonamido)pentan-1-yl]aminomethyl]imidazo[1,2-a]pyridine and 2.80 g (22.92 mmol) of 4-dimethylaminopyridine in 35 ml of chloroform was added dropwise 2.6 ml (22.92 mmol) of trichloroacetyl chloride, while stirring at room temperature for 3 minutes. The reaction mixture was heated for 15 hours under reflux. The reaction mixture was poured into ice-water, which was neutralized with a saturated aqueous solution of sodium hydrogencarbonate, which was extracted with 150 ml of chloroform. The organic layer was washed with 250 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 2.70 g of the desired compound (58.2%, pale yellow liquid).

Workup

  1. temperatureThe reaction mixture was heated for 15 hours
  2. temperatureunder reflux
  3. extractionwas extracted with 150 ml of chloroform
  4. washThe organic layer was washed with 250 ml of a saturated aqueous saline solution, which
  5. dry with materialwas dried over magnesium sulfate
  6. distillationby distilling off the solvent under reduced pressure
  7. customThe residue was purified by silicagel column chromatography (eluent: chloroform/methanol=100:1)

Sources & evidence

ORD record
ord-8787ca3d8ae44ca697cc15f8f2b6f963
Source dataset
uspto-grants-2001_06
Patent number
US06251905B1

Reaction notes

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