Trichloroacetyl chloride → HCID 21190252, compound

HRID 619533Notes

Reaction equation

HRID 619533 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[N:15]2[CH:16]=[CH:17][N:18]=[C:14]2[CH:13]=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC(Cl)(Cl)[C:21](Cl)=[O:22].C(=O)([O-])O.[Na+]>CN(C1C=CN=CC=1)C.C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][C:10]2[N:15]3[C:16](=[CH:17][N:18]=[C:14]3[CH:13]=[CH:12][CH:11]=2)[C:21]1=[O:22])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 211900715-(Tert-butoxycarbonylamino)methylimidazo[1,2-a]pyridine

Product 1

HCID 21190252HCID 21190252, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent2×

Procedure

To a solution of 989 mg (4.0 mmol) of 5-(tert-butoxycarbonylamino)methylimidazo[1,2-a]pyridine and 2200 mg (18.0 mmol) of 4-(N,N-dimethylamino)pyridine in 25 ml of chloroform was added dropwise 1.34 ml (12.0 mmol) of trichloroacetyl chloride at room temperature. The reaction mixture was heated for 5 hours under reflux. The reaction mixture was poured into ice-water. The mixture was neutralized with a saturated aqueous solution of sodium hydrogencarbonate. To the mixture was added 100 ml of chloroform for extraction of the desired compound. The organic layer was washed with 100 ml of a saturated saline, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform:methanol=20:1) to give 492 mg of the desired compound (45.0%, pale yellow solid).

Workup

  1. temperatureThe reaction mixture was heated for 5 hours
  2. temperatureunder reflux
  3. extractionfor extraction of the desired compound
  4. washThe organic layer was washed with 100 ml of a saturated saline
  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:methanol=20:1)

Sources & evidence

ORD record
ord-1ed3a3b5d1864dbea7381de95a50e788
Source dataset
uspto-grants-1999_09
Patent number
US05958942

Reaction notes

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