Formic Acid → HCID 90408160, compound

HRID 871086Notes

Reaction equation

HRID 871086 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:11]=[N:12][CH:13]=[C:14]([F:16])[CH:15]=2)[C:5]([NH2:17])=[CH:4][CH:3]=1.[CH:18](O)=O>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:17]=[CH:18][N:8]([CH2:9][C:10]3[CH:11]=[N:12][CH:13]=[C:14]([F:16])[CH:15]=3)[C:6]=2[CH:7]=1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 90408190HCID 90408190, compound

Product 1

HCID 90408160HCID 90408160, compound

Procedure

A solution of Example 12B (1.615 g, 5.45 mmol) in formic acid (4.53 mL, 120 mmol) was heated at 95° C. for 1 hour. After cooling, the mixture was concentrated and dissolved in ethyl acetate. The mixture was washed with 10% aqueous potassium carbonate and brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel flash chromatography (Isco®, Redi-Sep® column) eluting with a gradient of 50-100% ethyl acetate/hexane then 10% 2:1 methanol/water in ethyl acetate, followed by recrystallization from ethyl acetate/hexane, afforded the title compound. MS (ESI) m/z 305.8 (M+H)+.

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated
  3. dissolutiondissolved in ethyl acetate
  4. washThe mixture was washed with 10% aqueous potassium carbonate and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by silica gel flash chromatography (Isco®, Redi-Sep® column)
  9. washeluting with a gradient of 50-100% ethyl acetate/hexane
  10. custom10% 2:1 methanol/water in ethyl acetate, followed by recrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-7df0268c2f5244ff81916c438a390136
Source dataset
uspto-grants-2015_03
Patent number
US08969375B2

Reaction notes

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