Hydrochloric Acid → HCID 22711326, compound
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]=[CH:22][CH:21]=3)=[CH:18][N:19]=2)[CH2:11][CH2:10]1)=O)(C)(C)C>CO>[ClH:1].[N:23]1[CH:22]=[CH:21][C:20]([C:17]2[S:16][C:15]([N:12]3[CH2:11][CH2:10][NH:9][CH2:14][CH2:13]3)=[N:19][CH:18]=2)=[CH:25][CH:24]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A saturated solution of hydrochloride in methanol (12 ml) was added to 1-(tert-butoxycarbonyl)-4-[5-(pyridin-4-yl)thiazol-2-yl]piperazine (400 mg) at room temperature. After stirring for 1 hour, the reaction mixture was concentrated under reduced pressure, whereby the residue, that is, 1-[5-(pyridin-4-yl)thiazol-2-yl]piperazine hydrochloride was obtained as a white solid. In a solution of the resulting residue in methylene chloride (15 ml) was dissolved [1-phenylsulfonyl-5-(trimethylsilylethynyl)indol-2-yl]sulfonyl chloride (630 mg), followed by the addition of diisopropylethylamine (746 μl) at 0° C. After stirring for 4 hours, methylene chloride (10 ml) and a saturated aqueous solution (30 ml) of sodium bicarbonate were added to the reaction mixture to separate it into layers. The water layer was extracted with methylene chloride (2×10 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=6:1), whereby 1-[5-(2-methylpyridin-4-yl)thiazol-2-yl)-4-[[1-phenylsulfonyl-5-(trimethylsilylethynyl)indol-2-yl]sulfonyl]piperazine (214 mg) was obtained as a foam.
Workup
- concentrationthe reaction mixture was concentrated under reduced pressure, whereby the residue
Sources & evidence
- ORD record
- ord-a8773298372f4deeac092c73d2b31ab2
- Source dataset
- uspto-grants-2004_06
- Patent number
- US06747023B1
Reaction notes
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