Hydrochloric Acid → Ethyl 5-(3-{((1-acetylpiperidin-4-yl)carbonyl)amino}phenyl)isoxazole-3-carboxylate

HRID 1375661Notes

Reaction equation

HRID 1375661 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.Cl.[C:26]([N:29]1[CH2:34][CH2:33][CH:32]([C:35](Cl)=[O:36])[CH2:31][CH2:30]1)(=[O:28])[CH3:27].Cl>C(Cl)Cl>[C:26]([N:29]1[CH2:30][CH2:31][CH:32]([C:35]([NH:1][C:2]2[CH:3]=[C:4]([C:8]3[O:12][N:11]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:9]=3)[CH:5]=[CH:6][CH:7]=2)=[O:36])[CH2:33][CH2:34]1)(=[O:28])[CH3:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 44819012Ethyl 5-(3-aminophenyl)isoxazole-3-carboxylateHCID 534308101-Acetylpiperidine-4-carbonyl chloride hydrochloride

Product 1

HCID 69507772Ethyl 5-(3-{((1-acetylpiperidin-4-yl)carbonyl)amino}phenyl)isoxazole-3-carboxylateYield 78.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To ethyl 5-(3-aminophenyl)isoxazole-3-carboxylate (0.224 mmole) and triethylamine (0.896 mmole) in methylenechloride (3 mL) was added 1-acetyl-piperidine-4-carbonyl chloride HCl salt (0.314 mmole) via syringe at ambient temperature. After two hours, 1N HCl was added and the mixture was extracted with methylene chloride (3×40 mL). The combined organics were washed with aqueous Na2CO3, dried with anhydrous Na2SO4, filtered, concentrated under vacuo and purified by flash chromatography (10–15% ethyl acetate/Hexane) to provide (68 mg) of the titled compound.

Workup

  1. extractionthe mixture was extracted with methylene chloride (3×40 mL)
  2. washThe combined organics were washed with aqueous Na2CO3
  3. dry with materialdried with anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuo
  6. custompurified by flash chromatography (10–15% ethyl acetate/Hexane)

Sources & evidence

ORD record
ord-9170ff4822fc4e1587a10638502c28f8
Source dataset
uspto-grants-2007_01
Patent number
US07169797B2

Reaction notes

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