Sodium hydride → 3-Methyl-1-phenyl-5-(3-pyrazin-2-yl-5-m-tolyl-1H-imidazol-4-yl)-1,3-dihydro-benzoimidazol-2-one

HRID 1828165Notes

Reaction equation

[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([C:11]3[N:12]=[CH:13][NH:14][C:15]=3[C:16]3[CH:17]=[C:18]([CH3:22])[CH:19]=[CH:20][CH:21]=3)[CH:9]=[CH:10][C:5]=2[N:4]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:3]1=[O:29].[H-].[Na+].Cl[C:33]1[CH:38]=[N:37][CH:36]=[CH:35][N:34]=1>CN(C=O)C>[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([C:11]3[N:12]([C:33]4[CH:38]=[N:37][CH:36]=[CH:35][N:34]=4)[CH2:13][NH:14][C:15]=3[C:16]3[CH:17]=[C:18]([CH3:22])[CH:19]=[CH:20][CH:21]=3)[CH:9]=[CH:10][C:5]=2[N:4]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:3]1=[O:29]

Participants

Conditions

Temperature: 120 °C

Procedure

To a stirred solution of 3-Methyl-1-phenyl-5-(5-m-tolyl-1H-imidazol-4-yl)-1,3-dihydro-benzoimidazol-2-one (prepared as described previously in Example 200, 33 mg, 0.087 mmol) in DMF (0.1 mL) was added NaH (4 mg, 0.095 mmol). After stirring for 20 min, 2-chloropyrazine (9.3 mL, 0.10 μmol) was added and the reaction mixture was heated to 120° C. for 14 hours. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was purified by LC (Waters Symmetry C8, formic acid/acetonitrile/water) to afford 2 mg of the title compound.

Workup

temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated in vacuo
customThe residue was purified by LC (Waters Symmetry C8, formic acid/acetonitrile/water)

Sources & evidence

ORD record: ord-15fdf6f96b1b4eaaad02dab362d73ceb
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07056918B2

Reaction notes

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