Tetrahydrofuran → HCID 68835927, compound

HRID 2112948Notes

Reaction equation

HRID 2112948 reaction equation
[NH2:1][C:2]1[N:15]=[C:5]2[CH:6]=[C:7]([Br:14])[CH:8]=[C:9]([C:10]([NH:12][NH2:13])=[O:11])[N:4]2[N:3]=1.[CH2:16]=[C:17]1[O:21][C:19](=O)[CH2:18]1.C1COCC1>C(Cl)Cl>[NH2:1][C:2]1[N:15]=[C:5]2[CH:6]=[C:7]([Br:14])[CH:8]=[C:9]([C:10]3[O:11][C:19]([CH2:18][C:17](=[O:21])[CH3:16])=[N:13][N:12]=3)[N:4]2[N:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 12661DiketeneHCID 68839704HCID 68839704, compound2×

Product 1

HCID 68835927HCID 68835927, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of Step 1, 2-amino-7-bromo-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid hydrazide (1.0 g, 3.7 mmol), diketene (0.28 mL, 3.7 mmol) and THF (˜25 mL) were placed in a flask. The mixture was stirred at room temperature for 48 hours. The solvent was removed under reduced pressure and the residue was partitioned between water and a solution of 9:1 CH2Cl2/MeOH. The organics were dried with MgSO4 and concentrated to give an oily yellow solid. The solid was dissolved in a small amount of CH2Cl2 and filtered through a plug of silica, eluting with CH2Cl2. The filtrate was concentrated to give 1-[5-(2-amino-7-bromo-[1,2,4]triazolo[1,5-a]pyridine-5-yl)-[1,3,4]oxadiazol-2-yl]-propan-2-one, which was used without further purification, in Step 3. MS (APCI+): m/z 337.0, 339.0.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between water
  3. dry with materialThe organics were dried with MgSO4
  4. concentrationconcentrated
  5. customto give an oily yellow solid
  6. filtrationfiltered through a plug of silica
  7. washeluting with CH2Cl2
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-a0572e4bba51428da4e5df39daae014a
Source dataset
uspto-grants-2009_04
Patent number
US07524860B2

Reaction notes

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