HCID 58000840, compound → HCID 178515783, compound

HRID 2358257Notes

Reaction equation

HRID 2358257 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:21]3[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:28])[N:11](O)[C:12]=2[C:13]2[CH:18]=[CH:17][NH:16][C:15](=[O:19])[CH:14]=2)=[CH:4][CH:3]=1>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:21]3[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:28])[NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][NH:16][C:15](=[O:19])[CH:14]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 58000840HCID 58000840, compound

Product 1

HCID 178515783HCID 178515783, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of the intermediate from Example 1 Step C (11 g, 0.024 mol) in methanol (0.5 L) at 0° C. under nitrogen was added TiCl3 (15˜20%, 120 mL) over 45 minutes while maintaining the reaction temperature under 10° C. The solution was warmed to RT and stirred overnight. The volatiles were removed under reduced pressure, and the solution was made basic with saturated NaHCO3 and 5 N NaOH. Ethyl acetate was added and the mixture was stirred overnight. The solution was filtered through a Solka floe pad to remove the solids. The filtrate was extracted with EtOAc and the organic layer was then washed twice with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to provide the crude residue which was purified by on silica gel (gradient elution with 2%-10% DCM-methanol as an eluant) to yield the title compound. 1H NMR (300 MHz, DMSO-d6): δ13.12 (m, 1H), 11.45 (br, 1H), 7.22˜7.70 (m, 9H), 6.10˜6.32 (m, 2H).

Workup

  1. temperatureThe solution was warmed to RT
  2. customThe volatiles were removed under reduced pressure
  3. additionEthyl acetate was added
  4. stirringthe mixture was stirred overnight
  5. filtrationThe solution was filtered through a Solka floe pad
  6. customto remove the solids
  7. extractionThe filtrate was extracted with EtOAc
  8. washthe organic layer was then washed twice with brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customto provide the crude residue which
  13. customwas purified by on silica gel (
  14. washgradient elution with 2%-10% DCM-methanol as an eluant)

Sources & evidence

ORD record
ord-c580dc5c267640efb409de61269c558d
Source dataset
uspto-grants-2010_07
Patent number
US07763634B2

Reaction notes

Loading…