Hydrochloric Acid → HCID 21190174, compound

HRID 1068765Notes

Reaction equation

HRID 1068765 reaction equation
[C:1]([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)(OC)=[O:2].[BH4-].[Li+].Cl>C1COCC1.CO>[OH:2][CH2:1][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:25])([F:24])[F:26])(=[O:21])=[O:22])=[CH:11][CH:12]=[CH:13][C:8]2=[N:7][CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 21190198HCID 21190198, compound

Product 1

HCID 21190174HCID 21190174, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 396 mg (0.80 mmol) of 3-carbomethoxy-5-[N-tert-butoxycarbonyl-N-(3-trifluoromethanesulfonamidopropan-1-yl)aminomethyl]imidazo[1,2-a]pyridine in a mixture of 5.0 ml of THF and 1.0 ml of methanol was added, at room temperature, 87.12 mg (4.00 mmol) of lithium borohydride with small portions. The mixture was heated for 30 minutes under reflux. The reaction mixture was cooled to room temperature, and poured into ice-water. The mixture was neutralized with 1N HCl, and extracted with 50 ml of chloroform. The organic layer was washed with 50 ml of a saturated aqueous saline solution, which was dried over magnesium sulfate. The solvent was then distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; chloroform:methanol=20:1) to afford 269 mg of the desired compound (72%, a pale yellow liquid).

Workup

  1. additionwas added, at room temperature
  2. temperatureThe mixture was heated for 30 minutes
  3. temperatureunder reflux
  4. extractionextracted with 50 ml of chloroform
  5. washThe organic layer was washed with 50 ml of a saturated aqueous saline solution, which
  6. dry with materialwas dried over magnesium sulfate
  7. distillationThe solvent was then distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent; chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-b50912306e04468ba425fbed7b8a498e
Source dataset
uspto-grants-2001_06
Patent number
US06251905B1

Reaction notes

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