Dipropylamine → HCID 25116530, compound

HRID 1099434Notes

Reaction equation

HRID 1099434 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([C:11]([OH:13])=O)=[N:9][CH:10]=1)=[O:4].[CH2:14]([NH:17][CH2:18][CH2:19][CH3:20])[CH2:15][CH3:16].[OH-].[Na+]>CN(C)C=O.C(O)C>[CH2:14]([N:17]([CH2:18][CH2:19][CH3:20])[C:11]([C:8]1[CH:7]=[CH:6][C:5]([C:3]([OH:2])=[O:4])=[CH:10][N:9]=1)=[O:13])[CH2:15][CH3:16]

Participants

6

Reactant 3

HCID 8902DipropylamineHCID 14798Sodium HydroxideHCID 3149925-(Methoxycarbonyl)pyridine-2-carboxylic acid

Product 1

HCID 25116530HCID 25116530, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

N,N′-carbonyldiimidazole (145 mg, 0.89 mmol) was added to a solution of 5-(methoxycarbonyl)pyridine-2-carboxylic acid (162 mg, 0.89 mmol) in N,N-dimethylformamide (2.5 mL) at 60° C. The reaction mixture was stirred at 60° C. for 10 min. Dipropylamine (90 mg, 0.89 mmol) in N,N-dimethylformamide (1 mL) was added, and the reaction mixture was stirred at ambient temperature over night. The mixture was partitioned between saturated sodium bicarbonate and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuo. Half the amount of the crude intermediate (83 mg, 0.31 mmol) was dissolved in ethanol (3 mL) and 1 M sodium hydroxide (3 mL, 3 mmol) and heated to 50° C. for 30 min. The solvents were removed in vacuo and the residue was dissolved in water (3 mL) and cooled on ice. A 6 M hydrochloric acid solution was added dropwise and the solvents were removed in vacuo. The residue was added acetonitrile followed by evaporation in vacuo in order to remove trace of water. The procedure was repeated twice. The material was suspended in N,N-dimethylformamide and filtered. The filtrate was concentrated in vacuo to give 80 mg (64% total yield); MS (APPI/APCI) m/z 251[M+H+].

Workup

  1. stirringthe reaction mixture was stirred at ambient temperature over night
  2. customThe mixture was partitioned between saturated sodium bicarbonate and ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe solvents were removed in vacuo
  7. dissolutionthe residue was dissolved in water (3 mL)
  8. temperaturecooled on ice
  9. additionA 6 M hydrochloric acid solution was added dropwise
  10. customthe solvents were removed in vacuo
  11. additionThe residue was added acetonitrile
  12. customfollowed by evaporation in vacuo in order
  13. customto remove trace of water
  14. filtrationfiltered
  15. concentrationThe filtrate was concentrated in vacuo
  16. customto give
  17. custom80 mg (64% total yield)

Sources & evidence

ORD record
ord-4f046da05b3d4bb0b45080caaf80e5ef
Source dataset
uspto-grants-2012_03
Patent number
US08143408B2

Reaction notes

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