Hydrochloric Acid → (2-(4-Methoxyphenylamino)oxazol-4-yl)(2-((pyridin-3-yloxy)methyl)piperazin-1-yl)methanone dihydrochloride

HRID 70180Notes

Reaction equation

HRID 70180 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]2[O:25][CH:26]=[C:27]([C:29]([N:31]3[CH2:36][CH2:35][N:34](C(OC(C)(C)C)=O)[CH2:33][CH:32]3[CH2:44][O:45][C:46]3[CH:47]=[N:48][CH:49]=[CH:50][CH:51]=3)=[O:30])[N:28]=2)=[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]2[O:25][CH:26]=[C:27]([C:29]([N:31]3[CH2:36][CH2:35][NH:34][CH2:33][CH:32]3[CH2:44][O:45][C:46]3[CH:47]=[N:48][CH:49]=[CH:50][CH:51]=3)=[O:30])[N:28]=2)=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 131728864HCID 131728864, compound

Product 1

HCID 66796453(2-(4-Methoxyphenylamino)oxazol-4-yl)(2-((pyridin-3-yloxy)methyl)piperazin-1-yl)methanone dihydrochlorideYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4 M HCl in 1,4-dioxane (6 mL, 24 mmol) was added to a solution of tert-butyl 4-(2-(4-methoxyphenylamino)oxazole-4-carbonyl)-3-((pyridin-3-yloxy)methyl)piperazine-1-carboxylate TFA salt (35.5 mg, 0.057 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 20 mg (73%) of the title compound as a white solid. LC-MS: RT=3.51 min, [M+H]+=410.0.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. custompurified by HPLC (5 to 50% MeCN/0.1% TFA in H2O/0.1% TFA gradient)
  3. additionThe fractions containing the desired product
  4. concentrationwere concentrated under reduced pressure
  5. dissolutiondissolved in MeOH (1 mL)
  6. additiontreated with 4 M HCl in 1,4-dioxane (6 mL)
  7. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-91eb4e0aaf204a619763ddf22c51c101
Source dataset
uspto-grants-2014_09
Patent number
US08822472B2

Reaction notes

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