Hydrochloric Acid → N-(2,3-dihydro-1H-inden-5-yl)-2-((pyridin-3-yloxy)methyl)piperazine-1-carboxamide dihydrochloride
Reaction equation
[ClH:1].O1CCOCC1.OC(C(F)(F)F)=O.[CH2:15]1[C:23]2[C:18](=[CH:19][C:20]([NH:24][C:25]([N:27]3[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH:28]3[CH2:40][O:41][C:42]3[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=3)=[O:26])=[CH:21][CH:22]=2)[CH2:17][CH2:16]1>CO>[ClH:1].[ClH:1].[CH2:15]1[C:23]2[C:18](=[CH:19][C:20]([NH:24][C:25]([N:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH:28]3[CH2:40][O:41][C:42]3[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=3)=[O:26])=[CH:21][CH:22]=2)[CH2:17][CH2:16]1Participants
5
Procedure
4 M HCl in 1,4-dioxane (6 mL, 24 mmol) was added to a solution of tert-butyl 4-(2,3-dihydro-1H-inden-5-ylcarbamoyl)-3-((pyridin-3-yloxy)methyl)piperazine-1-carboxylate TFA salt (62.6 mg, 0.110 mmol) in MeOH (1 mL). After 1 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 concentrated under reduced pressure. The material was 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 30.7 mg (65%) of the title compound. LC-MS: RT=4.79 min, [M+H]+=353.2.
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
- dissolutionThe material was dissolved 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-91f3e34a6b844fa49a19ea072a95533a
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08822472B2
Reaction notes
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