Hydrochloric Acid → HCID 21190198, compound

HRID 1068764Notes

Reaction equation

HRID 1068764 reaction equation
ClC(Cl)(Cl)C([C:5]1[N:9]2[C:10]([CH2:14][N:15]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:16][CH2:17][CH2:18][NH:19][S:20]([C:23]([F:26])([F:25])[F:24])(=[O:22])=[O:21])=[CH:11][CH:12]=[CH:13][C:8]2=[N:7][CH:6]=1)=O.[CH3:36][O-:37].[Na+].Cl.[CH3:40][OH:41]>>[C:36]([C:5]1[N:9]2[C:10]([CH2:14][N:15]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:16][CH2:17][CH2:18][NH:19][S:20]([C:23]([F:26])([F:24])[F:25])(=[O:22])=[O:21])=[CH:11][CH:12]=[CH:13][C:8]2=[N:7][CH:6]=1)([O:41][CH3:40])=[O:37]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887Methanol2×HCID 10942334Sodium MethoxideHCID 21190110HCID 21190110, compound

Product 1

HCID 21190198HCID 21190198, compound

Procedure

To a solution of 581 mg (1.00 mmol) of 3-trichloroacetyl-5-[N-tert-butoxycarbonyl-N-(3-trifluoromethanesulfonamidopropan-1-yl)aminomethyl]imidazo[1,2-a]pyridine in 5.0 ml of methanol was added 0.46 ml (2.00 mmol) of a 25% methanol solution of sodium methylate. The mixture was stirred for 10 minutes at room temperature. The reaction mixture was poured into ice-water, which was neutralized with 1N HCl. The mixture was extracted with 50 ml of chloroform. The organic layer was washed with 50 ml of a saturated aqueous saline solution, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform) to afford 462 mg of the desired compound (93.4%, a pale yellow liquid).

Workup

  1. extractionThe mixture was extracted with 50 ml of chloroform
  2. washThe organic layer was washed with 50 ml of a saturated aqueous saline solution
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: chloroform)

Sources & evidence

ORD record
ord-aa59593e0a8c4c61871d4ae4f5017ac4
Source dataset
uspto-grants-2001_06
Patent number
US06251905B1

Reaction notes

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