Potassium Carbonate → 6-((5,6-dimethoxy-1H-benzo[d]imidazol-1-yl)methyl)-2-(methylthio)benzo[d]oxazole

HRID 1847987Notes

Reaction equation

HRID 1847987 reaction equation
CS(O[CH2:6][C:7]1[CH:17]=[CH:16][C:10]2[N:11]=[C:12]([S:14][CH3:15])[O:13][C:9]=2[CH:8]=1)(=O)=O.ClCC1C=CC2N=C(SC)OC=2C=1.[CH3:31][O:32][C:33]1[C:41]([O:42][CH3:43])=[CH:40][C:36]2[N:37]=[CH:38][NH:39][C:35]=2[CH:34]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:43][O:42][C:41]1[C:33]([O:32][CH3:31])=[CH:34][C:35]2[N:39]([CH2:6][C:7]3[CH:17]=[CH:16][C:10]4[N:11]=[C:12]([S:14][CH3:15])[O:13][C:9]=4[CH:8]=3)[CH:38]=[N:37][C:36]=2[CH:40]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 6012215,6-DimethoxybenzimidazoleHCID 86681015(2-(Methylthio)benzo[d]oxazol-6-yl)methyl methanesulfonateHCID 866810166-(Chloromethyl)-2-(methylthio)benzo[d]oxazole

Product 1

HCID 866810146-((5,6-dimethoxy-1H-benzo[d]imidazol-1-yl)methyl)-2-(methylthio)benzo[d]oxazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of a 9:1 mixture of (2-(methylthio)benzo[d]oxazol-6-yl)methyl methanesulfonate and 6-(chloromethyl)-2-(methylthio)benzo[d]oxazole (1.45 g) from Step 1 of this Example and 5,6-dimethoxybenzimidazole (945 mg, 5.31 mmol) in anhydrous DMF (10 mL) at rt was added solid K2CO3 (1.47 g, 10.62 mmol). The mixture was stirred at rt for 3 h. The mixture was partitioned between water and DCM. The organic layer was separated and washed with water. The organic layer was separated, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with 100% DCM to 10% MeOH in DCM to afford 6-((5,6-dimethoxy-1H-benzo[d]imidazol-1-yl)methyl)-2-(methylthio)benzo[d]oxazole (430 mg) as a solid. 1H NMR (300 MHz, DMSO-d6) δ 8.20 (s, 1H), 7.66 (m, 1H), 7.60 (d, J=9.0 Hz, 1H), 7.32 (dd, J=9.0, 3.0 Hz, 1H), 7.19 (s, 2H), 5.53 (s, 2H), 3.76 (s, 6H), 2.73 (s, 3H). LCMS (ESI) m/z 356 (M+H)+.

Workup

  1. customat rt
  2. customThe mixture was partitioned between water and DCM
  3. customThe organic layer was separated
  4. washwashed with water
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel flash chromatography
  10. washeluting with 100% DCM to 10% MeOH in DCM

Sources & evidence

ORD record
ord-469087f6565d4f0c81a5a34f931be870
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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