HCID 69849118, compound → HCID 22714176, compound

HRID 352242Notes

Reaction equation

HRID 352242 reaction equation
C(OC(=O)[NH:7][CH:8]([C:11](=[O:35])[NH:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH:15]([N:19]2[C:28]3[CH:27]=[CH:26][CH:25]=[C:24]([Cl:29])[C:23]=3[C:22]3=[N:30][O:31][C:32]([CH3:33])=[C:21]3[C:20]2=[O:34])[CH2:14]1)[CH2:9][OH:10])(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH2:7][CH:8]([CH2:9][OH:10])[C:11]([NH:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH:15]([N:19]2[C:28]3[CH:27]=[CH:26][CH:25]=[C:24]([Cl:29])[C:23]=3[C:22]3=[N:30][O:31][C:32]([CH3:33])=[C:21]3[C:20]2=[O:34])[CH2:14]1)=[O:35]

Participants

4

Reactant 1

HCID 69849118HCID 69849118, compound

Product 1

HCID 22714176HCID 22714176, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of {1-[3-(9-Chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-cyclohexylcarbamoyl]-2-hydroxy-ethyl }-carbamic acid tert-butyl ester, 92.3 mg (0.18 mmol) in 8 mL of 25% TFA in CH2Cl2 was stirred rt. for three hours then concentrated to dryness. The residue was partitioned between 20% isopropanol/chloroform and saturated aqueous NaHCO3. The organics were washed with saturated NaHCO3, washed with brine, dried over Na2SO4, filtered and concentrated to dryness. The residue was purified by radial chromatography using MeOH/chloroform as eluent and concentrated to dryness to yield 37 mg (50%) of the title compound as a white solid. MS (IS) 419.2 (M+).

Workup

  1. concentrationfor three hours then concentrated to dryness
  2. customThe residue was partitioned between 20% isopropanol/chloroform and saturated aqueous NaHCO3
  3. washThe organics were washed with saturated NaHCO3
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by radial chromatography
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-0bfa91f609bf4e6c9b5938979c0a1f92
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

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