Dimethylformamide → HCID 77230824, compound

HRID 1616241Notes

Reaction equation

HRID 1616241 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH:10]=[CH2:11])[C:5]([NH2:12])=[CH:4][CH:3]=1.CN([CH:16]=[O:17])C.O=C1CCC(=O)C1OC(=O)OC1C(=O)CCC1=O.C([O-])(O)=O.[Na+]>CCOC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:9][CH:10]=[CH2:11])[C:16](=[O:17])[NH:12][C:5]2=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 54297327HCID 54297327, compoundHCID 77230825HCID 77230825, compound

Product 1

HCID 77230824HCID 77230824, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

6-Chloro-N-(prop-2-en-1-yl)pyridine-2,3-diamine (71-3, 9.52 g, 51.8 mmol, 1.0 equiv) was added to anhydrous DMF (55 mL) to give a dark purple solution. Bis(2,5-dioxocyclopentyl)carbonate (13.18 g, 51.8 mmol, 1.0 equiv) was added in one portion to give a dark green solution. The resulting reaction mixture was then heated to 80° C. After 18 h, the reaction contents were cooled to RT, diluted with EtOAc (100 mL) and added slowly to saturated aqueous NaHCO3 (200 mL). The layers were separated and the aqueous layer was back-extracted with 3×100 mL EtOAc. The combined organics were dried over Na2SO4, filtered and concentrated to give a dark purple residue. Purification by normal-phase HPLC provided 5-chloro-3-(prop-2-en-1-yl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (71-4) as a tan solid. LRMS (M+H)+: observed=210.0, calculated=209.6.

Workup

  1. customto give a dark purple solution
  2. customto give a dark green solution
  3. customThe resulting reaction mixture
  4. customthe reaction contents
  5. temperaturewere cooled to RT
  6. customThe layers were separated
  7. extractionthe aqueous layer was back-extracted with 3×100 mL EtOAc
  8. dry with materialThe combined organics were dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give a dark purple residue
  12. customPurification by normal-phase HPLC

Sources & evidence

ORD record
ord-8e65bc3bbccc4c9bace9dbb5e516f2b5
Source dataset
uspto-grants-2014_07
Patent number
US08765784B2

Reaction notes

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