Hydrochloric Acid → N-(4-methoxyphenyl)-2-((pyridin-3-ylamino)methyl)piperazine-1-carboxamide dihydrochloride
Reaction equation
[ClH:1].O1CCOCC1.OC(C(F)(F)F)=O.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]([N:26]2[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH:27]2[CH2:39][NH:40][C:41]2[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=2)=[O:25])=[CH:19][CH:18]=1>CO>[ClH:1].[ClH:1].[CH3:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([NH:23][C:24]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH:27]2[CH2:39][NH:40][C:41]2[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=2)=[O:25])=[CH:21][CH:22]=1Participants
5
Procedure
4 M HCl in 1,4-dioxane (6 mL, 24 mmol) was added to a solution of tert-butyl 4-(4-methoxyphenylcarbamoyl)-3-((pyridin-3-ylamino)methyl)piperazine-1-carboxylate TFA salt (81.7 mg, 0.147 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 49.9 mg (82%) of the title compound as a white solid. LC-MS: RT=1.95 min, [M+H]+=342.1.
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
- 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-1fa5ac3c992e41058c6b48415328a2c3
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08822472B2
Reaction notes
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