Hydrochloric Acid → HCID 66797519, compound

HRID 70191Notes

Reaction equation

HRID 70191 reaction equation
[ClH:1].O1CCOCC1.OC(C(F)(F)F)=O.[F:15][C:16]1[CH:44]=[CH:43][CH:42]=[CH:41][C:17]=1[C:18]([N:20]1[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH:21]1[CH2:33][O:34][C:35]1[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=1)=[O:19]>CO>[ClH:1].[ClH:1].[F:15][C:16]1[CH:44]=[CH:43][CH:42]=[CH:41][C:17]=1[C:18]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH:21]1[CH2:33][O:34][C:35]1[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=1)=[O:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 131728866HCID 131728866, compound

Product 1

HCID 66797519HCID 66797519, compoundYield 86%

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-fluorobenzoyl)-3-((pyridin-3-yloxy)methyl)piperazine-1-carboxylate TFA salt (26 mg, 0.050 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 desired chromatography fractions were concentrated under reduced pressure, dissolved in MeOH (1 mL), and treated with 4 M HCl in 1,4-dioxane. This was concentrated under reduced pressure, yielding 16.3 mg (86%) of the title compound as an off-white solid. LC-MS: RT=3.00 min, [M+H]+=316.3.

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. concentrationThe desired chromatography fractions were concentrated under reduced pressure
  4. dissolutiondissolved in MeOH (1 mL)
  5. additiontreated with 4 M HCl in 1,4-dioxane
  6. concentrationThis was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c9d00c282dcd48fb9dc2e76abc18fd56
Source dataset
uspto-grants-2014_09
Patent number
US08822472B2

Reaction notes

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