Dimethylformamide → HCID 178424676, compound

HRID 1828173Notes

Reaction equation

HRID 1828173 reaction equation
Cl.NC1N[C:6]([C:8]2[CH:23]=[CH:22][C:11]3[N:12]([CH:17]4[CH2:21]CC[CH2:18]4)[C:13](=[O:16])[N:14]([CH3:15])[C:10]=3[CH:9]=2)=[C:5]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26](Cl)[CH:25]=2)N=1.Cl.[N:32]1[CH:37]=[CH:36][N:35]=[CH:34][C:33]=1[C:38]([NH2:40])=[NH:39].[CH3:41]N(C=O)C>O>[CH:17]([N:12]1[C:11]2[CH:22]=[CH:23][C:8]([C:6]3[N:39]=[C:38]([C:33]4[CH:34]=[N:35][CH:36]=[CH:37][N:32]=4)[NH:40][C:5]=3[C:24]3[CH:25]=[C:26]([CH3:41])[CH:27]=[CH:28][CH:29]=3)=[CH:9][C:10]=2[N:14]([CH3:15])[C:13]1=[O:16])([CH3:18])[CH3:21]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 470895Pyrazine-2-carboxamidine hydrochlorideHCID 22063817HCID 22063817, compound

Product 1

HCID 178424676HCID 178424676, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A stirred mixture of 5-(bromo-m-tolyl-acetyl)-1-isopropyl-3-methyl-1,3-dihydro-benzoimidazol-2-one (prepared as described in example 142, 0.5 gm, 1.25 mmol), pyrazine-2-carboxamidine hydrochloride (0.395 gm, 2,49 mmol) cesium carbonate (1.22 gm, 3.74 mmol) and DMF (4.0 mL) was heated to 60° C. After 1 hour, the reaction was determined to be complete by LCMS. The reaction was cooled to room temperature and diluted with water (40 mL). After stirring for 1 hour, the crude suspension was filtered and the solids were purified by flash chromatography (diethyl ether, followed by ethyl acetate) to afford 40 mg of the title compound as a light tan solid. MS (M+1)=425.1

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationthe crude suspension was filtered
  3. customthe solids were purified by flash chromatography (diethyl ether, followed by ethyl acetate)

Sources & evidence

ORD record
ord-5a3b2c52d1424f0286cfa922dcc74161
Source dataset
uspto-grants-2006_06
Patent number
US07056918B2

Reaction notes

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