Benzimidazole → HCID 22607246, compound

HRID 2307830Notes

Reaction equation

HRID 2307830 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([O:8][CH2:9][CH:10]2[CH2:12][O:11]2)[CH:7]=1.[NH:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[CH:14]1>CC(O)C.C(OCC)(=O)C>[N:13]1([CH2:12][CH:10]([OH:11])[CH2:9][O:8][C:6]2[CH:5]=[N:4][CH:3]=[C:2]([Br:1])[CH:7]=2)[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[CH:14]1

Participants

5

Reactant 2

HCID 5798BenzimidazoleHCID 22607599HCID 22607599, compound

Product 1

HCID 22607246HCID 22607246, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Example 436A (500 mg, 2.17 mmol) and 1H-Benzoimidazole (28 mg, 2.39 mmol) in 2-propanol (10 mL) was refluxed under N2 for 2 hrs. The reaction mixture was cooled, diluted with ethyl acetate(50 mL) and washed with brine (2×25 mL). The residue was concentrated and purified by flash column chromatography on silica gel eluting with 100% ethyl acetate to 5% methanol/ethyl acetate to provide the desire product (1.08 mmol, 50%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with brine (2×25 mL)
  3. concentrationThe residue was concentrated
  4. custompurified by flash column chromatography on silica gel eluting with 100% ethyl acetate to 5% methanol/ethyl acetate

Sources & evidence

ORD record
ord-f84e8f6d2dc44456b20f3e82f706d0b3
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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