Cesium carbonate → HCID 178423467, compound

HRID 1842490Notes

Reaction equation

HRID 1842490 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].Cl.Cl.[NH:9]1[CH2:12][CH:11]([C:13]2[NH:17][C:16]3[CH:18]=[CH:19][C:20]([CH3:22])=[CH:21][C:15]=3[N:14]=2)[CH2:10]1.[Cl:23][C:24]1[C:29](Cl)=[N:28][CH:27]=[CH:26][N:25]=1>CN1C(=O)CCC1>[Cl:23][C:24]1[C:29]([N:9]2[CH2:12][CH:11]([C:13]3[NH:17][C:16]4[CH:18]=[CH:19][C:20]([CH3:22])=[CH:21][C:15]=4[N:14]=3)[CH2:10]2)=[N:28][CH:27]=[CH:26][N:25]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 785752,3-DichloropyrazineHCID 178423463HCID 178423463, compound

Product 1

HCID 178423467HCID 178423467, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of cesium carbonate (4.44 g, 13.6 mmol) and 2-(azetidin-3-yl)-5-methyl-1H-benzo[d]imidazole dihydrochloride (1.05 g, 4.04 mmol) was added NMP (6 mL) and 2,3-dichloropyrazine (1.0 mL, 9.6 mmol). The reaction mixture was degassed and heated to 100° C. for 30 min. The reaction was diluted with EtOAc. The organic phase was washed with water (2×), brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (50% to 100% EtOAc in hexanes) gave 2-(1-(3-chloropyrazin-2-yl)azetidin-3-yl)-5-methyl-1H-benzo[d]imidazole (0.532 g, 1.78 mmol, 44% yield) as an orange solid.

Workup

  1. customThe reaction mixture was degassed
  2. additionThe reaction was diluted with EtOAc
  3. washThe organic phase was washed with water (2×), brine (1×)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash column chromatography on silica gel (50% to 100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-93e79b56ff1745a698a67540d464f8e1
Source dataset
uspto-grants-2015_02
Patent number
US08946230B2

Reaction notes

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