Isobutyl iodide → HCID 11492918, compound

HRID 1371564Notes

Reaction equation

HRID 1371564 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C:12]3[C:13]([NH2:17])=[N:14][O:15][N:16]=3)[NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:20](I)[CH:21]([CH3:23])[CH3:22]>CN(C=O)C>[CH2:20]([N:10]1[CH:11]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]=[C:9]1[C:12]1[C:13]([NH2:17])=[N:14][O:15][N:16]=1)[CH:21]([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 10556Isobutyl iodideHCID 24758Sodium hydrideHCID 178509304HCID 178509304, compound

Product 1

HCID 11492918HCID 11492918, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Synthesis of 4-(4-phenyl-1H-imidazol-2-yl)-1,2,5-oxadiazol-3-amine (50 mg, 0.22 mmol) was dissolved in DMF and NaH (15 mg, 0.7 mmol) was added. The reaction mixture became dark red. Isobutyl iodide (60 mg, 0.33 mmol) was added and the reaction mixture heated to 120 CC in the microwave for 5 minutes. The reaction mixture was concentrated to an oil which was purified by RPHPLC (CH3CN/H2O, 0.1% TFA) to give the product, 12 mg, 0.042 mmol, 19% yield. HPLC Method B Rt 4.50 min, MH+ 284.30. 1H NMR (500 MHz, CDCl3) δ 7.71 (m, 2H), 7.34 (m, 2H), 7.28 (s, 1H), 7.23 (m, 1H), 4.19 (d, J=7.4 Hz, 2H), 2.12 (m, 1H), 0.92 (d, J=6.7 Hz, 6H).

Workup

  1. temperaturethe reaction mixture heated to 120 CC in the microwave for 5 minutes
  2. concentrationThe reaction mixture was concentrated to an oil which
  3. customwas purified by RPHPLC (CH3CN/H2O, 0.1% TFA)
  4. customto give the product, 12 mg, 0.042 mmol, 19% yield

Sources & evidence

ORD record
ord-68534211d38247019b44355b547ffc84
Source dataset
uspto-grants-2007_01
Patent number
US07157476B2

Reaction notes

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