Hydrochloric Acid → HCID 66797122, compound

HRID 1487745Notes

Reaction equation

HRID 1487745 reaction equation
[ClH:1].O1CCOCC1.OC(C(F)(F)F)=O.[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1[S:26][C:25]([C:27]([N:29]2[CH2:34][CH2:33][N:32](C(OC(C)(C)C)=O)[CH2:31][CH:30]2[CH2:42][O:43][C:44]2[CH:45]=[N:46][CH:47]=[CH:48][CH:49]=2)=[O:28])=[CH:24][CH:23]=1>CO>[ClH:15].[ClH:1].[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1[S:26][C:25]([C:27]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH:30]2[CH2:42][O:43][C:44]2[CH:45]=[N:46][CH:47]=[CH:48][CH:49]=2)=[O:28])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 131728859HCID 131728859, compound

Product 1

HCID 66797122HCID 66797122, compoundYield 40%

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-(5-(2-chlorophenyl)thiophene-2-carbonyl)-3-((pyridin-3-yloxy)methyl)piperazine-1-carboxylate TFA salt (75.9 mg, 0.121 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 (6 mL). This was concentrated under reduced pressure, yielding 23.8 mg (40%) of the desired product as a white solid. LC-MS: RT=5.27 min, [M+H]+=414.1.

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 mL)
  6. concentrationThis was concentrated under reduced pressure

Sources & evidence

ORD record
ord-be432d8baf884db58d417905de25b320
Source dataset
uspto-grants-2016_08
Patent number
US09428522B2

Reaction notes

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