Hydrogen chloride-ethyl acetate → HCID 67777844, compound

HRID 1026338Notes

Reaction equation

HRID 1026338 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]2[N:8]([N:10]=[C:11]([C:14]3[CH:31]=[CH:30][C:17]([O:18][CH2:19][C@@H:20]([NH:22][C:23](=O)[O:24]C(C)(C)C)[CH3:21])=[CH:16][C:15]=3[F:32])[C:12]=2[F:13])[CH:9]=1)[CH3:2].Cl.[C:34](OCC)(=O)C>C(OCC)(=O)C>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]2[N:8]([N:10]=[C:11]([C:14]3[CH:31]=[CH:30][C:17]([O:18][CH2:19][C@@H:20]([NH:22][C:23](=[O:24])[CH3:34])[CH3:21])=[CH:16][C:15]=3[F:32])[C:12]=2[F:13])[CH:9]=1)[CH3:2]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 86666320HCID 86666320, compound

Product 1

HCID 67777844HCID 67777844, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of tert-butyl {(1S)-2-[4-(6-ethoxy-3-fluoropyrazolo[1,5-a]pyridin-2-yl)-3-fluorophenoxy]-1-methylethyl}carbamate (52 mg), 4 M hydrogen chloride/ethyl acetate (2 mL), and ethyl acetate (1 mL) was stirred at room temperature for 6 hr. The mixture was concentrated under reduced pressure. The residue was mixed with pyridine (1 mL) and acetic anhydride (1 mL). The mixture was stirred at room temperature overnight. 1 M hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (18.7 mg) as white crystals.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionThe residue was mixed with pyridine (1 mL) and acetic anhydride (1 mL)
  3. stirringThe mixture was stirred at room temperature overnight
  4. addition1 M hydrochloric acid was added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-522b42fad1534f10a5599da7d5a16151
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

Loading…