Hydrochloric Acid → HCID 66797129, compound

HRID 70184Notes

Reaction equation

HRID 70184 reaction equation
[ClH:1].O1CCOCC1.[Br:8][C:9]1[CH:10]=[C:11]([CH:35]=[CH:36][CH:37]=1)[C:12]([N:14]1[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH:15]1[CH2:27][O:28][C:29]1[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=1)=[O:13]>CO>[ClH:1].[ClH:1].[Br:8][C:9]1[CH:10]=[C:11]([C:12]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH:15]2[CH2:27][O:28][C:29]2[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=2)=[O:13])[CH:35]=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59671502Tert-butyl 4-(3-bromobenzoyl)-3-((pyridin-3-yloxy)methyl)piperazine-1-carboxylate

Product 1

HCID 66797129HCID 66797129, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4 M HCl in 1,4-dioxane (5 mL, 20 mmol) was added to a solution of tert-butyl 4-(3-bromobenzoyl)-3-((pyridin-3-yloxy)methyl)piperazine-1-carboxylate (126 mg, 0.264 mmol) in MeOH (1 mL). After stirring for 4 h, the reaction mixture was concentrated under reduced pressure and purified by HPLC (5 to 95% MeCN/0.1% TFA in H2O/0.1% TFA gradient). This gave 80.5 mg (68%) of the desired product as a white solid upon conversion to the dihydrochloride salt. LC-MS: RT=3.91 min, [M+H]+=376.5.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. custompurified by HPLC (5 to 95% MeCN/0.1% TFA in H2O/0.1% TFA gradient)

Sources & evidence

ORD record
ord-b059137da7964c289bd32d51f33a9717
Source dataset
uspto-grants-2014_09
Patent number
US08822472B2

Reaction notes

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