Tetrahydrofuran → HCID 90411156, compound

HRID 1521975Notes

Reaction equation

HRID 1521975 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([N+]([O-])=O)[CH:12]=[C:11]([Cl:18])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-:19].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.O.C(OCC)(=O)C>CN(C)C=O>[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([F:19])[CH:12]=[C:11]([Cl:18])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 15565813HCID 15565813, compoundHCID 22728543Water ethylacetate

Product 1

HCID 90411156HCID 90411156, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A solution of Example 212A (70 mg, 0.265 mmol) in 3 mL of N,N-dimethylformamide was treated with 1M tetra-n-butyl ammonium fluoride in tetrahydrofuran (0.531 mL, 0.531 mmol) and the mixture was heated at 65° C. for 12 hours. The mixture was poured into 30 mL 1:1 water/ethyl acetate and the organic layer was washed with water and brine, dried over sodium sulfate, filtered, and concentrated. Purification by column chromatography (silica, 5% ethyl acetate-hexane) afforded the title compound. LCMS: 236.8 (M+H)+.

Workup

  1. washthe organic layer was washed with water and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by column chromatography (silica, 5% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-4a7ed227288141829585c04bb235f129
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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