Hydrochloric Acid → HCID 21190107, compound

HRID 1068762Notes

Reaction equation

HRID 1068762 reaction equation
ClC(Cl)(Cl)C([C:5]1[N:9]2[C:10]([CH2:14][N:15]([C:30]([O:32]C(C)(C)C)=O)[CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:29])[C:22]([F:28])([F:27])[C:23]([F:26])([F:25])[F:24])=[CH:11][CH:12]=[CH:13][C:8]2=[N:7][CH:6]=1)=O.Cl>C(O)C>[F:28][C:22]([F:27])([C:23]([F:26])([F:24])[F:25])[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:30]1=[O:32])=[O:29]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21190229HCID 21190229, compound

Product 1

HCID 21190107HCID 21190107, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5.00 g (8.2 mmol) of 3-trichloroacetyl-5-[N-tert-butoxycarbonyl-N-(4-pentafluoropropionamidobutan-1-yl)aminomethyl]imidazo[1,2-a]pyridine in 100 ml of ethanol was added 3.4 ml (41.0 mmol) of 12N hydrochloric acid. The mixture was stirred for one hour at room temperature. The solvent and an excess volume of hydrochloric acid were distilled off under reduced pressure. The residue was dissolved in a mixture of 50 ml of purified water and 50 ml of ethanol. The solution was neutralized with 2N aqueous solution of sodium hydroxide. This solution was extracted with 150 ml of dichloromethane. The organic layer was washed with 150 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 2.11 g of the desired compound (66.1%, a pale yellow solid).

Workup

  1. distillationThe solvent and an excess volume of hydrochloric acid were distilled off under reduced pressure
  2. dissolutionThe residue was dissolved in a mixture of 50 ml of purified water and 50 ml of ethanol
  3. extractionThis solution was extracted with 150 ml of dichloromethane
  4. washThe organic layer was washed with 150 ml of a saturated aqueous saline solution
  5. dry with materialdried over magnesium sulfate
  6. distillationdistilled off the solvent under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent; dichloromethane:methanol=20:1)

Sources & evidence

ORD record
ord-8e7357c4bf4c49d8a78313192aa16989
Source dataset
uspto-grants-2001_06
Patent number
US06251905B1

Reaction notes

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