Sodium Carbonate → 2-(1-methylethyl)-6-(4-morpholinyl)-1-(1-naphthalenylmethyl)-1H-benzimidazol-4-amine

HRID 1188785Notes

Reaction equation

HRID 1188785 reaction equation
[CH3:1][CH:2]([C:4]1[N:8]([CH2:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)[C:7]2[CH:20]=[C:21]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[CH:22]=[C:23]([N+:24]([O-])=O)[C:6]=2[N:5]=1)[CH3:3].C([O-])([O-])=O.[Na+].[Na+]>CO>[CH3:3][CH:2]([C:4]1[N:8]([CH2:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)[C:7]2[CH:20]=[C:21]([N:27]3[CH2:28][CH2:29][O:30][CH2:31][CH2:32]3)[CH:22]=[C:23]([NH2:24])[C:6]=2[N:5]=1)[CH3:1]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 669769602-(1-methylethyl)-6-(4-morpholinyl)-1-(1-naphthalenylmethyl)-4-nitro-1H-benzimidazole

Product 1

HCID 669769232-(1-methylethyl)-6-(4-morpholinyl)-1-(1-naphthalenylmethyl)-1H-benzimidazol-4-amineYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

TiCl3 (16.3 mL) was added to a solution of 2-(1-methylethyl)-6-(4-morpholinyl)-1-(1-naphthalenylmethyl)-4-nitro-1H-benzimidazole (1.6 g) and NH4OAc (4 g) in MeOH (40 mL). After stirring for 4 h at room temperature, TLC showed no starting material. The pH of the mixture was made basic by adding Na2CO3 aqueous solution. The solvent was evaporated off under reduced pressure and the residue was extracted with DCM (250 mL×2). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in-vacuo to afford the desired product as a white solid (1.2 g, 81%). LC-MS: m/e=401 [M+1]+.

Workup

  1. customThe solvent was evaporated off under reduced pressure
  2. extractionthe residue was extracted with DCM (250 mL×2)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-e5e106b355f94e2087dea12088a4beb0
Source dataset
uspto-grants-2014_03
Patent number
US08674090B2

Reaction notes

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