HCID 2778779, compound → HCID 66939152, compound

HRID 1257456Notes

Reaction equation

HRID 1257456 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[C:6]=1[F:15])=O.[NH2:16][C:17](=[S:29])[CH2:18][C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=1>CO>[F:15][C:6]1[C:7]([C:11]([F:14])([F:13])[F:12])=[CH:8][CH:9]=[CH:10][C:5]=1[C:3]1[N:16]=[C:17]([CH2:18][C:19]2[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=2)[S:29][CH:2]=1

Participants

4

Reactant 2

HCID 2778779HCID 2778779, compoundHCID 58127823HCID 58127823, compound

Product 1

HCID 66939152HCID 66939152, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the compound (285 mg, 1.0 mmol) obtained in Example 186a in methanol (5 mL) was added the compound (209 mg, 1.00 mmol) obtained in Example 178a, and the mixture was heated under reflux for 3 hr. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with diluted aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate) to give the title compound (300 mg, 76%) as a colorless solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionthe residue was diluted with diluted aqueous sodium hydrogen carbonate solution
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate)

Sources & evidence

ORD record
ord-55a7c66f4e1a4beaaa9f9b8ef1e835f3
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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