5,6-Dimethoxybenzimidazole → HCID 86680991, compound

HRID 1847956Notes

Reaction equation

HRID 1847956 reaction equation
CS(O[CH2:6][C:7]1[CH:16]=[CH:15][C:10]2[N:11]=[C:12]([Br:14])[S:13][C:9]=2[CH:8]=1)(=O)=O.[CH3:17][O:18][C:19]1[C:27]([O:28][CH3:29])=[CH:26][C:22]2[NH:23][CH:24]=[N:25][C:21]=2[CH:20]=1>CN(C=O)C.CCOC(C)=O>[Br:14][C:12]1[S:13][C:9]2[CH:8]=[C:7]([CH2:6][N:23]3[C:22]4[CH:26]=[C:27]([O:28][CH3:29])[C:19]([O:18][CH3:17])=[CH:20][C:21]=4[N:25]=[CH:24]3)[CH:16]=[CH:15][C:10]=2[N:11]=1

Participants

5

Reactant 2

HCID 6012215,6-DimethoxybenzimidazoleHCID 86680990HCID 86680990, compound

Product 1

HCID 86680991HCID 86680991, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2-bromobenzo[d]thiazol-6-yl)methyl methanesulfonate (460 mg, 1.4 mmol) from Step 3 of this Example in DMF (5 mL) was added 5,6-dimethoxy-1H-benzo[d]imidazole (560 mg, 3.14 mmol) portion wise at rt. The mixture was stirred at rt overnight. The resulting solution was diluted with 40 mL of EtOAc and washed with water, brine. The separated organic layer was dried over MgSO4, and concentrated under reduced pressure The crude product was purified on a silica gel column using a mixture of MeOH—CH2Cl2 (1:20, v/v) as eluent to give 2-bromo-6-((5,6-dimethoxy-1H-benzo[d]imidazol-1-yl)methyl)benzo[d]thiazole as a light yellow solid (427 mg, 75%). LCMS (ESI) m/z 404, 406 (M+H)+.

Workup

  1. customwise at rt
  2. washwashed with water, brine
  3. dry with materialThe separated organic layer was dried over MgSO4
  4. concentrationconcentrated under reduced pressure The crude product
  5. customwas purified on a silica gel column
  6. additiona mixture of MeOH—CH2Cl2 (1:20

Sources & evidence

ORD record
ord-b9f1272bc9724d2198f73f4f88eed5f7
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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