Formic Acid → HCID 90408107, compound

HRID 871079Notes

Reaction equation

HRID 871079 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:9][CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[C:5]([NH2:16])=[CH:4][CH:3]=1.[CH:17](O)=O>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:16]=[CH:17][N:8]([CH2:9][CH:10]3[CH2:11][CH2:12][O:13][CH2:14][CH2:15]3)[C:6]=2[CH:7]=1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 65342903HCID 65342903, compound

Product 1

HCID 90408107HCID 90408107, compound

Procedure

A solution of the crude product of Example 5B (8.41 g, 29.5 mmol) in formic acid (10 mL, 261 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 297 (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-03eef9201949401ab1294a038197d118
Source dataset
uspto-grants-2015_03
Patent number
US08969375B2

Reaction notes

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