Ethanolamine → HCID 17985565, compound

HRID 557213Notes

Reaction equation

HRID 557213 reaction equation
Cl[C:2]1[C:7]2[CH:8]=[CH:9][O:10][C:6]=2[C:5]([CH2:11][C:12]([NH2:14])=[O:13])=[CH:4][N:3]=1.C(CN)O.[CH3:19][N:20](C)[CH:21]=O>>[CH3:19][N:20]([CH3:21])[C:2]1[C:7]2[CH:8]=[CH:9][O:10][C:6]=2[C:5]([CH2:11][C:12]([NH2:14])=[O:13])=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 700Ethanolamine2×HCID 6228DimethylformamideHCID 17985468HCID 17985468, compound

Product 1

HCID 17985565HCID 17985565, compoundYield 43%

Conditions

Temperature
130 °C

Procedure

Combine 2-(4-chlorofuro[3,2-c]pyridin-7-yl)acetamide (850 mg, 4.21 mmol), dimethylformamide (5 mL) and ethanolamine (0.76 mL, 12.63 mmol). Heat the reaction at 130° C. overnight. Add additional ethanolamine (0.25 ml) and heat at 130° C. overnight. Cool to room temperature, concentrate, and dilute with ethyl acetate. Wash with saturated aqueous sodium bicarbonate and concentrate. Subject to flash chromatography, eluting with ethylacetate:methanol to provide the title compound as a white solid (400 mg, 43%).

Workup

  1. temperatureHeat
  2. customthe reaction at 130° C. overnight
  3. temperatureCool to room temperature
  4. concentrationconcentrate
  5. additiondilute with ethyl acetate
  6. washWash with saturated aqueous sodium bicarbonate
  7. concentrationconcentrate
  8. washeluting with ethylacetate

Sources & evidence

ORD record
ord-d5b64bdf6bc2449c86b0e74defd62b24
Source dataset
uspto-grants-2011_11
Patent number
US08058425B2

Reaction notes

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