Hydrochloric Acid → HCID 21190242, compound

HRID 619475Notes

Reaction equation

HRID 619475 reaction equation
ClC(Cl)(Cl)C([C:5]1[N:9]2[C:10]([CH2:14][N:15]([C:27](OC(C)(C)C)=[O:28])[CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])=[CH:11][CH:12]=[CH:13][C:8]2=[N:7][CH:6]=1)=O.Cl>C(O)C>[F:24][C:22]([F:25])([F:23])[C:21]([NH:20][CH2:19][CH2:18][CH2:17][CH2:16][N:15]1[CH2:14][C:10]2[N:9]3[C:5](=[CH:6][N:7]=[C:8]3[CH:13]=[CH:12][CH:11]=2)[C:27]1=[O:28])=[O:26]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21190140HCID 21190140, compound

Product 1

HCID 21190242HCID 21190242, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2.60 g (4.64 mmol) of 3-trichloro acetyl-5-[N-tert-butoxycarbonyl-N-(4-trifluoroacetamidobutan-1-yl)aminomethyl]imidazo[1,2-a]pyridine in 20 ml of ethanol was added 1.90 ml (23.22 mmol) of 12N HCl. The mixture was stirred for one hour at room temperature. The solvent and excess volume of hydrochloric acid were distilled off under reduced pressure. The residue was dissolved in a mixture of 20 ml of purified water and 20 ml of ethanol. To this solution was added a 2N aqueous solution of sodium hydroxide to neutralize. This solution was extracted with 100 ml of dichloromethane. The organic layer was washed with 100 ml of a saturated aqueous saline solution, dried over magnesium sulfate, and distilled off the solvent under reduced pressure. The residue was purified by silica gel column chromatography (eluent; dichloromethane:methanol=20:1) to afford 1.26 g of the desired compound (75.9%, pale yellow amorphous).

Workup

  1. distillationThe solvent and excess volume of hydrochloric acid were distilled off under reduced pressure
  2. dissolutionThe residue was dissolved in a mixture of 20 ml of purified water and 20 ml of ethanol
  3. additionTo this solution was added a 2N aqueous solution of sodium hydroxide
  4. extractionThis solution was extracted with 100 ml of dichloromethane
  5. washThe organic layer was washed with 100 ml of a saturated aqueous saline solution
  6. dry with materialdried over magnesium sulfate
  7. distillationdistilled off the solvent under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent; dichloromethane:methanol=20:1)

Sources & evidence

ORD record
ord-b559587c393748488a4bc08464369051
Source dataset
uspto-grants-1999_09
Patent number
US05958942

Reaction notes

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