Acetic Acid → HCID 178467501, compound

HRID 658373Notes

Reaction equation

HRID 658373 reaction equation
[NH2:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[NH:13][C:14]2[CH:19]=[CH:18][C:17]([I:20])=[CH:16][C:15]=2[F:21])=[N:4][N:3]=1.[CH2:22](O)[CH3:23].C(O)(=O)C>CCOC(C)=O>[CH2:22]([O:6][C:2]1[NH:1][C:5]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[NH:13][C:14]2[CH:19]=[CH:18][C:17]([I:20])=[CH:16][C:15]=2[F:21])=[N:4][N:3]=1)[CH3:23]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 702EthanolHCID 17747573HCID 17747573, compound

Product 1

HCID 178467501HCID 178467501, compoundYield 27.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of [4-(5-Amino-[1,3,4]oxadiazol-2-yl)-pyridin-3-yl]-(2-floro-4-iodo-phenyl)-amine (150 mg, 0.38 mmol) in ethanol (10 mL) KOH 9212 mg, 3.78 mmol) was added. The reaction mixture was refluxed for 3 hrs. Then, added acetic acid was added to bring the pH to 5. The volatives were stripped and the residue was dissolved in EtOAc, and washed with 5% Na2CO3, and brine, and then dried over anhydrous MgSO4. After filtration and solvent removal the remaining crude product was subjected to silica gel column chromatography (eluent:Hex:ane EtOAc=1:1) to afford the desired product (45 mg). [5.08 min; 394(M+1)]

Workup

  1. temperatureThe reaction mixture was refluxed for 3 hrs
  2. additionwas added
  3. washwashed with 5% Na2CO3, and brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationAfter filtration and solvent removal the remaining crude product

Sources & evidence

ORD record
ord-849a67188a334aa58e55eb557e77edd8
Source dataset
uspto-grants-2011_12
Patent number
US08076486B2

Reaction notes

Loading…