Hydrochloric Acid → HCID 18936782, compound

HRID 357160Notes

Reaction equation

C(OC[O:10][CH2:11][CH2:12][C:13]([CH3:27])([CH3:26])[CH2:14][CH2:15][S:16][C:17]1[N:22]2[CH:23]=[CH:24][N:25]=[C:21]2[CH:20]=[CH:19][CH:18]=1)C1C=CC=CC=1.Cl>CO>[OH:10][CH2:11][CH2:12][C:13]([CH3:27])([CH3:26])[CH2:14][CH2:15][S:16][C:17]1[N:22]2[CH:23]=[CH:24][N:25]=[C:21]2[CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 0.71 g (1.85 mmol) of 5-(5-benzyloxymethyloxy-3,3-dimethylpentylthio)imidazo[1,2-a]pyridine in 10 ml of methanol, 0.33 ml (4.0 mmol) of concentrated hydrochloric acid was added, followed by stirring at 60° C. for 3 hours. After the reaction mixture was cooled, the solvent was distilled off. The residue was dissolved in 10 ml of water; 3 ml of 1N aqueous sodium hydroxide was added. To this mixture, 1N hydrochloric acid was added to pH 5-6. The mixture was extracted with dichloromethane and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, n-hexane/ethyl acetate=1/4→ethyl acetate) to yield 350 mg (71.6%, white crystal) of the desired product.

Workup

temperatureAfter the reaction mixture was cooled
distillationthe solvent was distilled off
dissolutionThe residue was dissolved in 10 ml of water
addition3 ml of 1N aqueous sodium hydroxide was added
additionTo this mixture, 1N hydrochloric acid was added to pH 5-6
extractionThe mixture was extracted with dichloromethane
customdried
distillationafter which the solvent was distilled off
customThe residue was purified by column chromatography (eluent, n-hexane/ethyl acetate=1/4→ethyl acetate)

Sources & evidence

ORD record: ord-86c50f2a5fa346159a3426ecd851cd81
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05840732

Reaction notes

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