HCID 57600282, compound → HCID 57600178, compound

HRID 2368623Notes

Reaction equation

HRID 2368623 reaction equation
[NH:1]1[C:9](=[O:10])[C:8]2[C:4]([N:5]=[CH:6][N:7]=2)=[N:3][C:2]1=[N:11][NH2:12].[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[O:25][N:24]=[C:23]([CH2:26][CH2:27][CH:28]=O)[N:22]=2)=[CH:17][CH:16]=1>C(O)C>[CH3:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[O:25][N:24]=[C:23]([CH2:26][CH2:27][C:28]3[N:1]4[C:9](=[O:10])[C:8]5[NH:7][CH:6]=[N:5][C:4]=5[N:3]([CH2:17][CH2:16][CH2:15][CH2:20][CH3:19])[C:2]4=[N:11][N:12]=3)[N:22]=2)=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 57600282HCID 57600282, compoundHCID 178514337HCID 178514337, compound

Product 1

HCID 57600178HCID 57600178, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1H-purine-2,6-dione 2-hydrazone (680 mg, 2.88 mmol) and 3-[5-(4-methoxyphenyl)-1,2,4-oxadiazol-3-yl]propanal (900 mg, 3.88 mol) in ethanol (20 mL) was refluxed for 4 hours. The reaction mixture was concentrated and the residue was mixed with acetic acid (10 mL). The resulting mixture was refluxed for 3 hours. The reaction mixture was concentrated and then diluted with water and extracted with EtOAc (3×). The combined organic layers was dried over Na2SO4, filtered, concentrated and purified by preparative LCMS to give the desired product (830 mg, 64% yield). LCMS calculated for C22H25N8O3 (M+H): 449.2. Found: 449.2.

Workup

  1. temperaturewas refluxed for 4 hours
  2. concentrationThe reaction mixture was concentrated
  3. additionthe residue was mixed with acetic acid (10 mL)
  4. temperatureThe resulting mixture was refluxed for 3 hours
  5. concentrationThe reaction mixture was concentrated
  6. additiondiluted with water
  7. extractionextracted with EtOAc (3×)
  8. dry with materialThe combined organic layers was dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-9445f305cc7249e388de132f9efb6458
Source dataset
uspto-grants-2014_04
Patent number
US08703783B2

Reaction notes

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