Formic Acid → HCID 89996059, compound

HRID 1480824Notes

Reaction equation

HRID 1480824 reaction equation
[CH3:1][O:2][C:3]1[C:8]([NH2:9])=[CH:7][CH:6]=[C:5]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[N:4]=1.[CH:16](O)=[O:17]>>[CH3:1][O:2][C:3]1[C:8]([NH:9][CH:16]=[O:17])=[CH:7][CH:6]=[C:5]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[N:4]=1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 12152132526184-47-4

Product 1

HCID 89996059HCID 89996059, compoundYield 88%

Procedure

A solution of 2-methoxy-6-morpholinopyridin-3-amine (Preparation 70, 40 mg, 0.191 mmol) in formic acid (3 mL) was heated to reflux for 3 hours. The reaction mixture was concentrated in vacuo. The residue was partitioned between aqueous saturated NaHCO3 (40 mL) and EtOAc (40 mL). The aqueous layer was re-extracted with EtOAc (40 mL). The combined organic layers were washed with water (40 mL) and brine (40 mL), dried (MgSO4) and concentrated in vacuo, to give the title compound (40 mg, 88%).

Workup

  1. temperatureto reflux for 3 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customThe residue was partitioned between aqueous saturated NaHCO3 (40 mL) and EtOAc (40 mL)
  4. extractionThe aqueous layer was re-extracted with EtOAc (40 mL)
  5. washThe combined organic layers were washed with water (40 mL) and brine (40 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-32ce2748e4284442922b4f18630c6df5
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

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