2-Bromo-1-(4-(dimethylamino)phenyl)ethanone → 4-(6-chloroimidazo[1,2-a]pyrazin-2-yl)-N,N-dimethylbenzenamine

HRID 2367859Notes

Reaction equation

HRID 2367859 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.Br[CH2:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([N:19]([CH3:21])[CH3:20])=[CH:15][CH:14]=1)=O.C([O-])(O)=O.[Na+]>C(#N)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:6]([CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([N:19]([CH3:21])[CH3:20])=[CH:15][CH:14]=3)[N:8]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 1422252-Bromo-1-(4-(dimethylamino)phenyl)ethanoneHCID 516892Sodium BicarbonateHCID 128084192-Amino-5-chloropyrazine

Product 1

HCID 177593314-(6-chloroimidazo[1,2-a]pyrazin-2-yl)-N,N-dimethylbenzenamineYield 7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a double necked round bottomed flask equipped with condenser and under nitrogen flow were introduced 5-chloro-2-amino-pyrazine (61 mg, 0.47 mmol), 2-bromo-4′-dimethylamino-acetophenone (170 mg, 0.71 mmol) and anhydrous acetonitrile (7 mL). The reaction mixture was refluxed for 3 hrs. After it cooled down, NaHCO3 (71 mg, 0.85 mmol) was added. The reaction was refluxed for another 6 hrs. The solvent was removed and the crude product (221 mg) was purified by FCC (hex/DCM/AcOEt=2:2:1), to afford 9 mg (yield 7%) of the product as yellow solid. 1HNMR (270 MHz; CDCl3), δ 8.82 (s, 1H, Ar—H), 8.09 (s, 1H, Ar—H), 7.822 (s, 1H, Ar—H), 7.818 (d, 3JHH=8.9 Hz, 2H, Ar—H), 6.77 (d, 3JHH=8.7 Hz, 2H, Ar—H), 3.02 (s, 6H, NCH3). m/z (CI-MS): 273 ([M+1]+), 261, 239 ([M−Cl+1]+).

Workup

  1. customIn a double necked round bottomed flask equipped with condenser and under nitrogen flow
  2. temperatureThe reaction mixture was refluxed for 3 hrs
  3. temperatureAfter it cooled down
  4. temperatureThe reaction was refluxed for another 6 hrs
  5. customThe solvent was removed
  6. customthe crude product (221 mg) was purified by FCC (hex/DCM/AcOEt=2:2:1)

Sources & evidence

ORD record
ord-1ec772cb162942a9877afc8508fbebfe
Source dataset
uspto-grants-2014_04
Patent number
US08703096B2

Reaction notes

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