Trichloroacetyl chloride → HCID 21190127, compound

HRID 1068714Notes

Reaction equation

HRID 1068714 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:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:12][CH2:13][CH2:14][CH2:15][NH:16][S:17]([C:20]([F:23])([F:22])[F:21])(=[O:19])=[O:18])[N:5]2[CH:31]=1.[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>[CH3:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]([C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])[CH2:12][CH2:13][CH2:14][CH2:15][NH:16][S:17]([C:20]([F:21])([F:23])[F:22])(=[O:19])=[O:18])[N:5]2[C:31]=1[C:34](=[O:35])[C:33]([Cl:38])([Cl:37])[Cl:32]

Participants

6

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 21190074HCID 21190074, compound

Product 1

HCID 21190127HCID 21190127, compoundYield 65.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 2.90 g (6.24 mmol) of 2-methyl-5-[N-tert-butoxycarbonyl-N-[4-(trifluoromethanesulfonamido)butan-1-yl]aminomethyl]imidazo[1,2-a]pyridine and 2.29 g (18.73 mmol) of 4-dimethylaminopyridine in 25 ml of chloroform was added dropwise, for 3 minutes, 2.1 ml (18.73 mmol) of trichloroacetyl chloride. The reaction mixture was heated for 20 hours under reflux. The reaction mixture was then 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 and 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 2.47 g of the desired compound (65.2%, pale yellow liquid).

Workup

  1. temperatureThe reaction mixture was heated for 20 hours
  2. temperatureunder reflux
  3. extractionfollowed by extraction 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. 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-9ad4640d4b2b471d955a5c4648426726
Source dataset
uspto-grants-2001_06
Patent number
US06251905B1

Reaction notes

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