Benzimidazole → HCID 23633224, compound

HRID 1158761Notes

Reaction equation

HRID 1158761 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[N:7]=[C:8]([N:26]([CH3:28])[CH3:27])[N:9]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:10]=1[C:11]([O:13][C:14]([CH3:19])([CH3:18])[CH2:15][O:16][CH3:17])=[O:12])=[O:4].[N:29]1[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2[NH:31][CH:30]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N:29]1([CH2:2][C:3]([NH:5][C:6]2[N:7]=[C:8]([N:26]([CH3:28])[CH3:27])[N:9]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:10]=2[C:11]([O:13][C:14]([CH3:19])([CH3:18])[CH2:15][O:16][CH3:17])=[O:12])=[O:4])[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2[N:31]=[CH:30]1

Participants

5

Reactant 3

HCID 5798BenzimidazoleHCID 11430Potassium CarbonateHCID 68644062HCID 68644062, compound

Product 1

HCID 23633224HCID 23633224, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

2-Methoxy-1,1-dimethylethyl 4-[(bromoacetyl)amino]-2-(dimethylamino)-1-phenyl-1H-imidazole-5-carboxylate (35 mg, 1 eq), synthesized in an analogous manner/method as described for example 90), benzimidazole (2.5 eq) and K2CO3 (22 mg, 2 eq) were dissolved in DMF (5 mL). The reaction was stirred for 1 h at 75° C. The solvent was evaporated off and to the residue was added K2CO3(aq) (1 M, 50 mL) and extracted with ether. The organic phases were pooled, dried (MgSO4.H2O), filtered and evaporated. Eventually the crude material was purified by preparatory HPLC, which gave the desired pure product. Yield: 41%. 1H-NMR d (CDCl3): 1.29 (s, 6H), 2.68 (s, 6H), 3.27 (s, 2H), 3.31 (s, 3H), 5.3-5.9 (s, 2H), 7.24-7.32 (m, 4H), 7.41 (m, 4H), 7.80 (d, 1H), 8.02 (s, 1H), 9.50 (s, 1H).

Workup

  1. customThe solvent was evaporated off and to the residue
  2. additionwas added K2CO3(aq) (1 M, 50 mL)
  3. extractionextracted with ether
  4. dry with materialdried (MgSO4.H2O)
  5. filtrationfiltered
  6. customevaporated
  7. customEventually the crude material was purified by preparatory HPLC, which
  8. customgave the desired pure product

Sources & evidence

ORD record
ord-2d6882d621264a96a6613058f4af3823
Source dataset
uspto-grants-2010_10
Patent number
US07812026B2

Reaction notes

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