Benzyl carbazate → 1H-Benzimidazole-5-carboxylic acid, 1-cyclohexyl-2-(3-furanyl)-, hydrazide

HRID 1007724Notes

Reaction equation

HRID 1007724 reaction equation
[CH:1]1([N:7]2[C:11]3[CH:12]=[CH:13][C:14]([C:16]([OH:18])=O)=[CH:15][C:10]=3[N:9]=[C:8]2[C:19]2[CH:23]=[CH:22][O:21][CH:20]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([NH:34][NH2:35])(OCC1C=CC=CC=1)=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.C1COCC1.CCO.[Pd].CCOC(C)=O>[CH:1]1([N:7]2[C:11]3[CH:12]=[CH:13][C:14]([C:16]([NH:34][NH2:35])=[O:18])=[CH:15][C:10]=3[N:9]=[C:8]2[C:19]2[CH:23]=[CH:22][O:21][CH:20]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

9

Reactant 4

HCID 79242Benzyl carbazateHCID 81531DiisopropylethylamineHCID 4911131-Cyclohexyl-2-(furan-3-yl)-1H-benzimidazole-5-carboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 233781581H-Benzimidazole-5-carboxylic acid, 1-cyclohexyl-2-(3-furanyl)-, hydrazide

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

The benzimidazole carboxylic acid of example 2 (0.500 g, 1.61 mmol) was stirred in DMF (10 mL) with N-Cbz-hydrazine (0.268 g, 1.61 mmol), TBTU (0.620 g, 1.93 mmol) and DIEA (0.727 g, 563 mmol) for 3 days. EtOAc was added and the reaction mixture was washed twice with 10% aqueous citric acid, twice with saturated aqueous NaHCO3 and once with brine. The organic layer was dried over anhydrous MgSO4, filtered and concentrated to give a brown foam that was hydrogenolyzed in THF-EtOH (1:1) with 10% Pd/C (70 mg) under an atmosphere of hydrogen for 8 h. The suspension was filtered and concentrated to dryness to give 1-cyclohexyl-2-furan-3-yl-1H-benzoimidazole-5-carboxylic acid hydrazide as a brown foam.

Workup

  1. washthe reaction mixture was washed twice with 10% aqueous citric acid, twice with saturated aqueous NaHCO3 and once with brine
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a brown foam that
  6. filtrationThe suspension was filtered
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-32acb6836aaf464cbcbd4c07eb8519b8
Source dataset
uspto-grants-2004_09
Patent number
US06794404B2

Reaction notes

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