Hydrochloric Acid → 1-[5-(2-Methylpyridin-4-yl)thiazol-2-yl]piperazine hydrochloride
Reaction equation
[ClH:1].C(OC([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[S:16][C:17]([C:20]3[CH:25]=[CH:24][N:23]=[C:22]([CH3:26])[CH:21]=3)=[CH:18][N:19]=2)[CH2:11][CH2:10]1)=O)(C)(C)C>CO>[ClH:1].[CH3:26][C:22]1[CH:21]=[C:20]([C:17]2[S:16][C:15]([N:12]3[CH2:13][CH2:14][NH:9][CH2:10][CH2:11]3)=[N:19][CH:18]=2)[CH:25]=[CH:24][N:23]=1Participants
Procedure
A saturated solution of hydrochloride in methanol (12 ml) was added to 1-(t-butoxycarbonyl)-4-[5-(2-methylpyridin-4-yl)thiazol-2-yl]piperazine (400 mg) at room temperature. After stirring for 10 minutes, the reaction mixture was concentrated under reduced pressure, whereby 1-[5-(2-methylpyridin-4-yl)thiazol-2-yl]piperazine hydrochloride was obtained as a white solid. In a solution of the resulting hydrochloride in methylene chloride (12 ml) was dissolved 5-chloro-1-phenylsulfonylindol-2-sulfonyl chloride (522 mg), followed by the addition of diisopropylethylamine (538 μl) at room temperature. After stirring for 3 hours, a saturated aqueous solution (50 ml) of sodium bicarbonate was added to the reaction. mixture to separate it into layers. The water layer was extracted with methylene chloride (2×15 ml). The organic layers were combined, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (methylene chloride:acetone=7:1), whereby the title compound (240 mg) was obtained as a foam.
Workup
- concentrationthe reaction mixture was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-6eed87210b764a9191ef036f199d542e
- Source dataset
- uspto-grants-2004_06
- Patent number
- US06747023B1
Reaction notes
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