Cyanogen Bromide → N-[methyl]-N-methoxy 1-(cyclopentyl)-2-amino-1H-benzimidazole-6-carboxamide

HRID 250727Notes

Reaction equation

HRID 250727 reaction equation
[CH3:1][O:2][N:3]([CH3:19])[C:4](=[O:18])[C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[C:7]([NH:12][CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:6]=1.C[O-].[Li+].[N:23]#[C:24]Br>ClCCl>[CH3:19][N:3]([O:2][CH3:1])[C:4]([C:5]1[CH:10]=[CH:9][C:8]2[N:11]=[C:24]([NH2:23])[N:12]([CH:13]3[CH2:14][CH2:15][CH2:16][CH2:17]3)[C:7]=2[CH:6]=1)=[O:18]

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 4177230Lithium methanolateHCID 86067041N-[methoxy]-N-[methyl]3-cyclopentylamino-4-aminobenzamide

Product 1

HCID 86623264N-[methyl]-N-methoxy 1-(cyclopentyl)-2-amino-1H-benzimidazole-6-carboxamideYield 82.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine N-[methoxy]-N-[methyl]3-cyclopentylamino-4-aminobenzamide (1.79 g, 6.82 mmol) and lithium methoxide (0.27 g, 7.16 mmol) in anhydrous dichloromethane (25 mL) and stir for 20 minutes. Add a solution of cyanogen bromide (0.83 g, 7.84 mmol) anhydrous dichloromethane (8 mL) and stir overnight at room temperature under nitrogen. Concentrate under reduced pressure and partition the residue between ethyl acetate and water. Wash the organic layer sequentially saturated aqueous sodium bicarbonate (2×20 mL), saturated aqueous sodium chloride (2×20 mL), and water (2×20 mL). Dry over magnesium sulfate and concentrate under reduced pressure to provide the desired compound as a dark solid (1.62 g, 82%).

Workup

  1. concentrationConcentrate under reduced pressure
  2. custompartition the residue between ethyl acetate and water
  3. washWash the organic layer sequentially saturated aqueous sodium bicarbonate (2×20 mL), saturated aqueous sodium chloride (2×20 mL), and water (2×20 mL)
  4. dry with materialDry over magnesium sulfate
  5. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-b540c85261344a36895d583a2b04d225
Source dataset
uspto-grants-2011_01
Patent number
US07863310B2

Reaction notes

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