Cesium carbonate → HCID 46199250, compound

HRID 1959353Notes

Reaction equation

HRID 1959353 reaction equation
Br[C:2]1[N:3]=[C:4]([C:9]2[NH:13][C:12]3[CH:14]=[C:15]([CH3:18])[CH:16]=[CH:17][C:11]=3[N:10]=2)[C:5]([NH2:8])=[N:6][CH:7]=1.[NH:19]1[CH:24]=[CH:23][C:22](=[O:25])[CH:21]=[CH:20]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1C(=O)CCC1.CCOC(C)=O.[Cu]>[NH2:8][C:5]1[N:6]=[CH:7][C:2]([N:19]2[CH:24]=[CH:23][C:22](=[O:25])[CH:21]=[CH:20]2)=[N:3][C:4]=1[C:9]1[NH:13][C:12]2[CH:14]=[C:15]([CH3:18])[CH:16]=[CH:17][C:11]=2[N:10]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 122904-PyridinolHCID 580842975-bromo-3-(6-methyl-1H-benzo[d]imidazol-2-yl)pyrazin-2-amine

Product 1

HCID 46199250HCID 46199250, compoundYield 30%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 5-bromo-3-(6-methyl-1H-benzimidazol-2-yl)pyrazin-2-amine (80 mg, 0.263 mmol), pyridin-4(1H)-one (287 mg, 2.63 mmol), cesium carbonate (257 mg, 0.8 mmol) and copper (5 mg, 0.08 mmol) were heated in NMP (2 mL) at 150° C. for 1 hour. The reaction mixture was diluted with EtOAc, washed with 1N NaOH, and the organic layer filtered through a pad of celite and concentrated in vacuo. The resulting solid was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were collected and freeze-dried to give the title compound (24.7 mg, 30% Yield).

Workup

  1. washwashed with 1N NaOH
  2. filtrationthe organic layer filtered through a pad of celite
  3. concentrationconcentrated in vacuo
  4. customThe resulting solid was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]
  5. customThe fractions were collected
  6. customfreeze-dried

Sources & evidence

ORD record
ord-13067b5e5f5541d0b86230f1c59a9414
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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