Hydrochloric Acid → HCID 66796921, compound

HRID 70208Notes

Reaction equation

HRID 70208 reaction equation
[ClH:1].O1CCOCC1.[O:8]1[C:16]2[C:11](=[N:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[C:9]1[N:17]1[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH:18]1[CH2:30][O:31][C:32]1[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=1>CO>[ClH:1].[N:34]1[CH:35]=[CH:36][CH:37]=[C:32]([O:31][CH2:30][CH:18]2[CH2:19][NH:20][CH2:21][CH2:22][N:17]2[C:9]2[O:8][C:16]3[C:11]([N:10]=2)=[N:12][CH:13]=[CH:14][CH:15]=3)[CH:33]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 312751,4-Dioxane2×HCID 59671471HCID 59671471, compound

Product 1

HCID 66796921HCID 66796921, compoundYield 64%

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-(oxazolo[4,5-b]pyridin-2-yl)-3-((pyridin-3-yloxy)methyl)piperazine-1-carboxylate (273 mg, 0.664 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 fractions containing the desired product were combined and brought to pH 12 with 1 N NaOH and were extracted with EtOAc (3×). The combined organics were dried over Na2SO4, filtered, and concentrated under reduced pressure. The material was dissolved in MeOH (1 mL) and 4 M HCl in 1,4-dioxane (1 equiv. HCl, 0.116 mL) was added. The mixture was concentrated under reduced pressure to give 148 mg (64%) of the desired product as the hydrochloride salt. LC-MS: RT=2.18 min, [M+H]+=312.5.

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. extractionwere extracted with EtOAc (3×)
  5. dry with materialThe combined organics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. dissolutionThe material was dissolved in MeOH (1 mL)
  9. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8ebb355a40d84e97854845a242446c27
Source dataset
uspto-grants-2014_09
Patent number
US08822472B2

Reaction notes

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