Trifluoroacetic anhydride → HCID 117987805, compound

HRID 2205980Notes

Reaction equation

HRID 2205980 reaction equation
[O:1]=[C:2]1[C:7]2[C:8]([C:16]3[CH:17]=[C:18]([C:21]([NH2:23])=O)[S:19][CH:20]=3)=[CH:9][N:10]([CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])[C:6]=2[CH:5]=[CH:4][NH:3]1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>CC(N(C)C)=O.O>[O:1]=[C:2]1[C:7]2[C:8]([C:16]3[CH:17]=[C:18]([C:21]#[N:23])[S:19][CH:20]=3)=[CH:9][N:10]([CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])[C:6]=2[CH:5]=[CH:4][NH:3]1

Participants

5

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 117988213HCID 117988213, compound

Product 1

HCID 117987805HCID 117987805, compoundYield 74.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 4-(4-oxo-1-(pentan-3-yl)-4,5-dihydro-1H-pyrrolo[3,2-c]pyridin-3-yl)thiophene-2-carboxamide (13.0 mg) obtained in Example 8 in DMA (2 mL) was slowly added dropwise trifluoroacetic anhydride (8.36 μL) under nitrogen atmosphere at 0° C., and the mixture was allowed to be warmed to room temperature, and stirred overnight at room temperature. The reaction mixture was diluted with water, and the mixture was extracted three times with ethyl acetate. The combined organic layers were washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate) to give the title compound (9.2 mg).

Workup

  1. extractionthe mixture was extracted three times with ethyl acetate
  2. washThe combined organic layers were washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-c0b634858d62429fae797a12ccbbae04
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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