Hydrochloric Acid → (2-(Phenylamino)oxazol-4-yl)(2-((pyridin-3-yloxy)methyl)piperazin-1-yl)methanone dihydrochloride
Reaction equation
[ClH:1].O1CCOCC1.OC(C(F)(F)F)=O.[C:15]1([NH:21][C:22]2[O:23][CH:24]=[C:25]([C:27]([N:29]3[CH2:34][CH2:33][N:32](C(OC(C)(C)C)=O)[CH2:31][CH:30]3[CH2:42][O:43][C:44]3[CH:45]=[N:46][CH:47]=[CH:48][CH:49]=3)=[O:28])[N:26]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CO>[ClH:1].[ClH:1].[C:15]1([NH:21][C:22]2[O:23][CH:24]=[C:25]([C:27]([N:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH:30]3[CH2:42][O:43][C:44]3[CH:45]=[N:46][CH:47]=[CH:48][CH:49]=3)=[O:28])[N:26]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1Participants
5
Procedure
4 M HCl in 1,4-dioxane (6 mL, 24 mmol) was added to a solution of tert-butyl 4-(2-(phenylamino)oxazole-4-carbonyl)-3-((pyridin-3-yloxy)methyl)piperazine-1-carboxylate TFA salt (64.8 mg, 0.109 mmol) in MeOH (1 mL). After stirring overnight, 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 concentrated under reduced pressure, dissolved in MeOH (1 mL), and treated with 4 M HCl in 1,4-dioxane (6 mL). The mixture was concentrated under reduced pressure to give 41 mg (83%) of the title compound as a white solid. LC-MS: RT=3.29 min, [M+H]+=380.0.
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
- concentrationwere concentrated under reduced pressure
- dissolutiondissolved in MeOH (1 mL)
- additiontreated with 4 M HCl in 1,4-dioxane (6 mL)
- concentrationThe mixture was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-d0c0abde1d3e497ab41d5fa9709b4e12
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08822472B2
Reaction notes
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