Water → HCID 44476050, compound

HRID 2096990Notes

Reaction equation

HRID 2096990 reaction equation
COC1C=CC(C[NH:8][C:9]2[C:13]3[CH:14]=[CH:15][C:16]([CH3:33])=[C:17]([C:18]4[CH:23]=[C:22]5[NH:24][C:25](=[O:32])[C:26]6([CH2:31][CH2:30][O:29][CH2:28][CH2:27]6)[C:21]5=[CH:20][CH:19]=4)[C:12]=3[O:11][N:10]=2)=CC=1.FC(F)(F)C(O)=O.O.C(=O)([O-])O.[Na+]>ClCCl.C(OCC)(=O)C>[NH2:8][C:9]1[C:13]2[CH:14]=[CH:15][C:16]([CH3:33])=[C:17]([C:18]3[CH:23]=[C:22]4[NH:24][C:25](=[O:32])[C:26]5([CH2:27][CH2:28][O:29][CH2:30][CH2:31]5)[C:21]4=[CH:20][CH:19]=3)[C:12]=2[O:11][N:10]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acid2×HCID 516892Sodium BicarbonateHCID 44476049HCID 44476049, compound

Product 1

HCID 44476050HCID 44476050, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-(3-(4-methoxybenzylamino)-6-methylbenzo[d]isoxazol-7-yl)-2′,3′,5′,6′-tetrahydrospiro[indoline-3,4′-pyran]-2-one (example 10, 0.12 g, 0.26 mmol) in dichloromethane (2 mL) was added trifluoroacetic acid (2 mL) and the solution was stirred at room temperature for 5 hours. Water and solid sodium hydrogen carbonate were added in order to neutralize the trifluoroacetic acid. Ethyl acetate was added and the organic phase was separated, dried (MgSO4), filtered and evaporated under reduced pressure. The residue was purified by flash chromatography (96:4 dichloromethane/methanol) to yield the title compound (38 mg, 44%) as a white solid.

Workup

  1. customthe organic phase was separated
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified by flash chromatography (96:4 dichloromethane/methanol)

Sources & evidence

ORD record
ord-83f776c1c9824059a9a90b73f30410ee
Source dataset
uspto-grants-2013_05
Patent number
US08450341B2

Reaction notes

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