Triethylamine → HCID 58541943, compound

HRID 1966754Notes

Reaction equation

HRID 1966754 reaction equation
[Br:1][C:2]1[CH:24]=[CH:23][C:5]2[N:6]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:7]([C:9]3[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=3[C:11]([NH:13][NH2:14])=[O:12])=[N:8][C:4]=2[CH:3]=1.C(N(CC)CC)C.C1N=CN([C:37](N2C=NC=C2)=[O:38])C=1>C1COCC1.CCOC(C)=O.O>[Br:1][C:2]1[CH:24]=[CH:23][C:5]2[N:6]([C:19]([CH3:20])([CH3:21])[CH3:22])[C:7]([C:9]3[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=3[C:11]3[O:12][C:37](=[O:38])[NH:14][N:13]=3)=[N:8][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 58541917HCID 58541917, compound

Product 1

HCID 58541943HCID 58541943, compoundYield 42.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 22728543Water ethylacetateSolvent

Procedure

To a round bottom flask is added 2-(5-bromo-1-tert-butyl-1H-benzimidazol-2-yl)-benzoic acid hydrazide (310 mg, 0.8 mmol) in THF (4 mL), followed by the addition of triethylamine (2 mL) and CDI (390 mg, 2.405 mmol). The reaction mixture is stirred at room temperature for 18 hours. The reaction mixture is diluted with EtOAc/water. The organic layer is separated, washed with brine, dried under anhydrous Na2SO4, filtered and concentrated. The residue is purified by silica gel flash column chromatography with 0-5% MeOH/CH2Cl2 as the eluent to afford 5-[2-(5-bromo-1-tert-butyl-1H-benzimidazol-2-yl)-phenyl]-3H-[1,3,4]oxadiazol-2-one (140 mg, 42%) as a light brown solid. LCMS (ESMS): m/z 413.07, 415.04 (M++1).

Workup

  1. customThe organic layer is separated
  2. washwashed with brine
  3. customdried under anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by silica gel flash column chromatography with 0-5% MeOH/CH2Cl2 as the eluent

Sources & evidence

ORD record
ord-fafd5b916bfa492f97e39e13126cc919
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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