Imidazole → HCID 178468579, compound

HRID 2068280Notes

Reaction equation

HRID 2068280 reaction equation
[NH2:1][C:2]1[N:6]([C@H:7]2[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9][CH2:8]2)[C:5]2[CH:14]=[CH:15][C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:17][C:4]=2[N:3]=1.CN(C)C=O.N1C=CN=C1.[Si:33](Cl)([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34]>C(OCC)(=O)C>[NH2:1][C:2]1[N:6]([C@H:7]2[CH2:12][CH2:11][C@H:10]([O:13][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])[CH2:9][CH2:8]2)[C:5]2[CH:14]=[CH:15][C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:17][C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 178468578HCID 178468578, compound

Product 1

HCID 178468579HCID 178468579, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 2-amino-1-(trans-4-hydroxycyclohexyl)-1H-benzimidazole-5-carboxylate (0.97 g, 0.0032 mol) was dissolved in N,N-dimethylformamide (10 mL, 0.2 mol) at room temperature. 1H-Imidazole (0.50 g, 0.0074 mol) and tert-butyldimethylsilyl chloride (0.53 g, 0.0035 mol) were added and the mixture stirred at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate and washed with saturated bicarbonate then brine. The organics were collected and dried over sodium sulfate and concentrated. The crude solid was purified by combiflash chromatography using methylene chloride and methanol as eluent. Product fractions were concentrated to give an off white solid (1.099 g). MS (ESI (+)m/z) 418.04 (M+H+)

Workup

  1. washwashed with saturated bicarbonate
  2. customThe organics were collected
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe crude solid was purified by combiflash chromatography
  6. concentrationProduct fractions were concentrated

Sources & evidence

ORD record
ord-560dd890ce4f4f19ac41c6fed1fef5aa
Source dataset
uspto-grants-2012_10
Patent number
US08293923B2

Reaction notes

Loading…