2-Methyl-5-(6-nitrobenzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole → 2-Methyl-5-(6-aminobenzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74218Notes

Reaction equation

HRID 74218 reaction equation
[CH3:1][C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)[C:5]2[CH:13]=[CH:14][C:15]([C:17]3[O:18][C:19]4[CH:25]=[C:24]([N+:26]([O-])=O)[CH:23]=[CH:22][C:20]=4[N:21]=3)=[CH:16][C:4]=2[N:3]=1.[H][H]>[Pd].CO>[CH3:1][C:2]1[N:6]([CH:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[C:5]2[CH:13]=[CH:14][C:15]([C:17]3[O:18][C:19]4[CH:25]=[C:24]([NH2:26])[CH:23]=[CH:22][C:20]=4[N:21]=3)=[CH:16][C:4]=2[N:3]=1

Participants

5

Reactant 2

HCID 674986292-Methyl-5-(6-nitrobenzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 674987622-Methyl-5-(6-aminobenzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazoleYield 40.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Methyl-5-(6-nitrobenzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole (see Working Example 47-2) (135 mg, 0.357 mmol) was added to methanol (20 mL) containing palladium/carbon (Pd: 10%, 0.06 g), hydrogen was substituted in by successively reducing the pressure and purging with hydrogen gas 3 times, and this was stirred at room temperature for 2.5 hours. After substituting in nitrogen, the insoluble material was filtered off through a Celite layer (20 mm thickness), and this same layer was washed with methanol (20 mL, 3 times). The filtrate was combined with the wash solutions and the solvent was distilled out at reduced pressure, the residue obtained was purified by silica gel column chromatography to yield the title compound (50 mg, 40.2% yield) as brown crystals.

Workup

  1. custompurging with hydrogen gas 3 times
  2. filtrationthe insoluble material was filtered off through a Celite layer (20 mm thickness)
  3. washthis same layer was washed with methanol (20 mL, 3 times)
  4. distillationthe solvent was distilled out at reduced pressure
  5. customthe residue obtained
  6. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-833e975568284f908dc7e5138b34377f
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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