Hydrochloric Acid → HCID 18452640, compound

HRID 1271306Notes

Reaction equation

C([O:5][C:6](=[O:36])[CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]([C:17]1[C:22]([Cl:23])=[N:21][C:20]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:19]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:18]=1)[CH:14]([CH3:16])[CH3:15])(C)(C)C.Cl.[OH-].[Na+]>O1CCOCC1>[Cl:23][C:22]1[C:17]([N:13]([CH2:12][CH2:11][CH2:10][CH2:9][O:8][CH2:7][C:6]([OH:36])=[O:5])[CH:14]([CH3:16])[CH3:15])=[N:18][C:19]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[C:20]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:21]=1

Participants

Conditions

Temperature: 80 °C

Procedure

218 mg of 2-{4-[N-(3-chloro-5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butyloxy}acetic acid tert-butyl ester was dissolved in 2 ml of 1,4-dioxane and 2 ml of 1N hydrochloric acid was added, followed by stirring at 80° C. for one hour. The mixture was further stirred at 110° C. for 4 hours. The reaction solution was neutralized with 1N sodium hydroxide solution and then extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and then the solvent was evaporated under reduced pressure. The resulting crude crystal was washed with a solvent of hexane-ethyl acetate (4:1) to obtain 120 mg of the desired product as a gray crystal having a melting point of 136 to 138° C.

Workup

stirringThe mixture was further stirred at 110° C. for 4 hours
extractionextracted with ethyl acetate
dry with materialThe extract was dried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
washThe resulting crude crystal was washed with a solvent of hexane-ethyl acetate (4:1)

Sources & evidence

ORD record: ord-8ef8ce9aaaa347aa82c7374b4458efeb
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07205302B2

Reaction notes

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