Hydrochloric Acid → HCID 24878565, compound

HRID 70150Notes

Reaction equation

HRID 70150 reaction equation
Cl.O1CCOCC1.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]([N:25]3[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH:26]3[CH2:38][O:39][C:40]3[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=3)=[O:24])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1>CO>[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[CH:17]=[CH:18][C:19]([NH:22][C:23]([N:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH:26]3[CH2:38][O:39][C:40]3[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=3)=[O:24])=[CH:20][CH:21]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59671621Tert-butyl 4-(4'-methoxybiphenyl-4-ylcarbamoyl)-3-((pyridin-3-yloxy)methyl)piperazine-1-carboxylate

Product 1

HCID 24878565HCID 24878565, compound

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-(4′-methoxybiphenyl-4-ylcarbamoyl)-3-((pyridin-3-yloxy)methyl)piperazine-1-carboxylate (114.9 mg, 0.182 mmol) in MeOH (1 mL). After 2 h, the reaction mixture was concentrated under reduced pressure, and the material was purified by HPLC (5 to 50% MeCN/0.1% TFA in H2O/0.1% TFA gradient). The desired fractions were brought to pH 12 with 1 N NaOH in H2O and were extracted with EtOAc (3×). The combined organics were dried over Na2SO4, filtered, and concentrated under reduced pressure. This gave 28.6 mg (38%) of the desired product as a white solid. LC-MS: RT=4.97 min, [M+H]+=419.2.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customthe material was purified by HPLC (5 to 50% MeCN/0.1% TFA in H2O/0.1% TFA gradient)
  3. extractionwere extracted with EtOAc (3×)
  4. dry with materialThe combined organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3e3f5df0ff2048ceb88e3247dbcdb8f7
Source dataset
uspto-grants-2014_09
Patent number
US08822472B2

Reaction notes

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