Triethylamine → 5-[3-(1H-indazol-5-yl)-1,2,4-oxadiazol-5-yl]-2-[(1-methylethyl)oxy]benzonitrile

HRID 2189775Notes

Reaction equation

HRID 2189775 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH:13]([CH3:15])[CH3:14])[C:6](Cl)=[O:7])#[N:2].O[NH:17][C:18]([C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][N:24]=[CH:23]2)=[NH:19].C(N(CC)CC)C>C(#N)C>[NH:25]1[C:26]2[C:22](=[CH:21][C:20]([C:18]3[N:17]=[C:6]([C:5]4[CH:9]=[CH:10][C:11]([O:12][CH:13]([CH3:15])[CH3:14])=[C:3]([CH:4]=4)[C:1]#[N:2])[O:7][N:19]=3)=[CH:28][CH:27]=2)[CH:23]=[N:24]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 575058423-Cyano-4-isopropoxybenzoyl chlorideHCID 178513242HCID 178513242, compound

Product 1

HCID 532473675-[3-(1H-indazol-5-yl)-1,2,4-oxadiazol-5-yl]-2-[(1-methylethyl)oxy]benzonitrileYield 20.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Cyano-4-[(1-methylethyl)oxy]benzoyl chloride (D106) (545 mg, 2.437 mmol) and N-hydroxy-1H-indazole-5-carboximidamide (D2) (685 mg, 2.437 mmol) were dissolved in acetonitrile (30 ml) before adding triethylamine (0.374 ml, 2.68 mmol). The resulting mixture was stirred at room temperature for 3 h then at 80° C. for 48 h, then cooled at room temperature. The precipitate formed was filtered off and dissolved in EtOAc and washed with water, evaporated and chromatographed [0-15% EtOAc in cyclohexane] to give the title compound (170 mg, 17%) as a pink solid. MS (ES): C19H15N5O2 requires 345; found (MH+) 346

Workup

  1. waitat 80° C. for 48 h
  2. temperaturecooled at room temperature
  3. customThe precipitate formed
  4. filtrationwas filtered off
  5. dissolutiondissolved in EtOAc
  6. washwashed with water
  7. customevaporated
  8. customchromatographed [0-15% EtOAc in cyclohexane]

Sources & evidence

ORD record
ord-c7f25a267cde4006be43d6e2ca68044e
Source dataset
uspto-grants-2012_12
Patent number
US08324254B2

Reaction notes

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