Potassium Carbonate → N-(3-((5-aminopyrazin-2-yl)methylamino)-4-methylphenyl)-4-((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)benzamide

HRID 2199308Notes

Reaction equation

HRID 2199308 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:30])[C:11]2[CH:16]=[CH:15][C:14]([CH2:17][N:18]3[CH2:23][CH2:22][N:21]([CH2:24][CH3:25])[CH2:20][CH2:19]3)=[C:13]([C:26]([F:29])([F:28])[F:27])[CH:12]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].C([O-])([O-])=O.[K+].[K+].Br[CH2:38][C:39]1[N:40]=[CH:41][C:42]([NH:45]C(=O)OC(C)(C)C)=[N:43][CH:44]=1>CN(C=O)C>[NH2:45][C:42]1[N:43]=[CH:44][C:39]([CH2:38][NH:1][C:2]2[CH:3]=[C:4]([NH:9][C:10](=[O:30])[C:11]3[CH:16]=[CH:15][C:14]([CH2:17][N:18]4[CH2:23][CH2:22][N:21]([CH2:24][CH3:25])[CH2:20][CH2:19]4)=[C:13]([C:26]([F:29])([F:28])[F:27])[CH:12]=3)[CH:5]=[CH:6][C:7]=2[CH3:8])=[N:40][CH:41]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 45073740tert-Butyl (5-(bromomethyl)pyrazin-2-yl)carbamateHCID 67324831N-(3-amino-4-methylphenyl)-4-((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)benzamide

Product 1

HCID 67346239N-(3-((5-aminopyrazin-2-yl)methylamino)-4-methylphenyl)-4-((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)benzamideYield 55.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution N-(3-amino-4-methylphenyl)-4-((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)benzamide (70 mg, 0.17 mmol) in DMF (0.5 mL) were added K2CO3 (69 mg,0.50 mmol) and tert-butyl 5-(bromomethyl)pyrazin-2-ylcarbamate (48 mg,0.17 mmol). The reaction mixture was stirred for 8 hours at room temperature after which, it was partitioned between ethyl acetate and water. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by flash chromatography using (5% MeOH/CH2Cl2) as a solvent to afford title compound (50 mg, 47% yield). MS m/z: 628 [M+1].

Workup

  1. customwas partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-e0253f9c191b42bc9b87b95243b85584
Source dataset
uspto-grants-2016_06
Patent number
US09358231B2

Reaction notes

Loading…