Diisopropylcarbodiimide → HCID 70981759, compound

HRID 1409365Notes

Reaction equation

HRID 1409365 reaction equation
[NH2:1][C:2](=[N:8][OH:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:10][N:11]1[C:15]([CH3:16])=[CH:14][C:13]([C:17](O)=O)=[N:12]1.C(N=C=NC(C)C)(C)C>C(Cl)Cl>[CH3:10][N:11]1[C:15]([CH3:16])=[CH:14][C:13]([C:17]2[O:9][N:8]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[N:1]=2)=[N:12]1

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 5877571,5-dimethyl-1H-pyrazole-3-carboxylic acidHCID 6785548Ethyl 2-amino-2-(hydroxyimino)acetate

Product 1

HCID 70981759HCID 70981759, compoundYield 31.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl aminohydroxyiminoacetate (3.78 mmol, 0.5 g), 1,5-dimethyl-1H-pyrazole-3-carboxylic acid (95%, 3.78 mmol, 0.530 g) and 1,3-diisopropylcarbodiimide (4.16 mmol, 0.525 g) were suspended in DCM (70 ml) under nitrogen atmosphere. The mixture was stirred at RT for a day. The solvent was evaporated and pyridine was added to the residue. The resulting mixture was refluxed for 6 h and stirred at RT overnight. Pyridine was evaporated and the residue diluted with DCM and water. The phases were separated and the water phase was extracted four times with DCM. The combined organics were washed with aqueous HCl solution, saturated NaHCO3, water and brine. The organic phase was dried, filtered and evaporated. The crude product was purified by flash chromatography. 0.285 g of the title compound was obtained. 1H-NMR (400 MHz, MeOH-d4): δ 1.43 (t, 3H), 2.30 (s, 3H), 4.23 (s, 3H), 4.49 (q, 2H), 6.96 (s, 1H).

Workup

  1. customThe solvent was evaporated
  2. additionpyridine was added to the residue
  3. temperatureThe resulting mixture was refluxed for 6 h
  4. stirringstirred at RT overnight
  5. customPyridine was evaporated
  6. additionthe residue diluted with DCM and water
  7. customThe phases were separated
  8. extractionthe water phase was extracted four times with DCM
  9. washThe combined organics were washed with aqueous HCl solution, saturated NaHCO3, water and brine
  10. customThe organic phase was dried
  11. filtrationfiltered
  12. customevaporated
  13. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-d9cb5d0781634ae8872db7ea9b7a3914
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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