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

HRID 1280100Notes

Reaction equation

HRID 1280100 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[C:10](O)=O.[C:13](NN)([O:15][CH2:16][C:17]1C=CC=CC=1)=O.CN(C(ON1N=N[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CC[N:49](C(C)C)C(C)C.C[N:57]([CH:59]=[O:60])C>C1COCC1.CCO.[Pd].CCOC(C)=O>[CH:34]1([N:3]2[C:4]3[CH:9]=[CH:8][C:7]([C:59]([NH:57][NH2:49])=[O:60])=[CH:6][C:5]=3[N:1]=[C:2]2[C:10]2[CH:17]=[CH:16][O:15][CH:13]=2)[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]1

Participants

9

Reactant 5

HCID 6228DimethylformamideHCID 79242Benzyl carbazateHCID 81531DiisopropylethylamineHCID 2332402-Benzimidazolecarboxylic 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 3

HCID 23938PalladiumCatalystHCID 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-b3840f76c6d445fe91ddbaa6da8edf79
Source dataset
uspto-grants-2002_09
Patent number
US06448281B1

Reaction notes

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