Hydrochloric Acid → 2-(2-((Pyridin-3-yloxy)methyl)piperazin-1-yl)benzo[d]thiazole
Reaction equation
Cl.O1CCOCC1.OC(C(F)(F)F)=O.OC(C(F)(F)F)=O.[S:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[N:24]=[C:23]1[N:31]1[CH2:36][CH2:35][N:34](C(OC(C)(C)C)=O)[CH2:33][CH:32]1[CH2:44][O:45][C:46]1[CH:47]=[N:48][CH:49]=[CH:50][CH:51]=1>CO>[N:48]1[CH:49]=[CH:50][CH:51]=[C:46]([O:45][CH2:44][CH:32]2[CH2:33][NH:34][CH2:35][CH2:36][N:31]2[C:23]2[S:22][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[N:24]=2)[CH:47]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
4 M HCl in 1,4-dioxane (6 mL, 24 mmol) was added to a solution of tert-butyl 4-(benzo[d]thiazol-2-yl)-3-((pyridin-3-yloxy)methyl)piperazine-1-carboxylate di-TFA salt (116.4 mg, 0.215 mmol) in MeOH (1 mL). After 12 h, the reaction mixture was concentrated under reduced pressure and purified by HPLC (5 to 50% MeCN/0.1% TFA in H2O/0.1% TFA gradient). The fractions containing the desired product were brought to pH 12 with 1 N NaOH and were extracted with EtOAc (3×). The combined organics were dried over Na2SO4, filtered, and concentrated under reduced pressure. This gave 41.7 mg (59%) of the desired product as an off-white, sticky solid. LC-MS: RT=4.38 min, [M+H]+=327.1.
Workup
- concentrationthe reaction mixture was concentrated under reduced pressure
- custompurified by HPLC (5 to 50% MeCN/0.1% TFA in H2O/0.1% TFA gradient)
- additionThe fractions containing the desired product
- extractionwere extracted with EtOAc (3×)
- dry with materialThe combined organics were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-bc3e092f5c974af18e253b59174e497b
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08822472B2
Reaction notes
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