Sodium Carbonate → HCID 57855683, compound

HRID 1177892Notes

Reaction equation

HRID 1177892 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[O:7]=[C:8]([N:20]1[CH2:25][CH2:24][N:23]([C:26](=[O:37])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:33]([F:36])([F:35])[F:34])[CH2:22][CH2:21]1)[CH2:9][NH:10][C:11]([C:13]1[CH:18]=[N:17][C:16](Cl)=[CH:15][N:14]=1)=[O:12].[C:38]1(B(O)O)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>CN(C=O)C.Cl[Pd]Cl>[O:7]=[C:8]([N:20]1[CH2:25][CH2:24][N:23]([C:26](=[O:37])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:33]([F:36])([F:35])[F:34])[CH2:22][CH2:21]1)[CH2:9][NH:10][C:11]([C:13]1[CH:18]=[N:17][C:16]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[CH:15][N:14]=1)=[O:12]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 86634090HCID 86634090, compound

Product 1

HCID 57855683HCID 57855683, compoundYield 13.3%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Na2CO3 (140 mg, 1.32 mmol) was added to a stirred solution of 5-chloro-pyrazine-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide (200 mg, 0.44 mmol) in DMF (3 mL). PdCl2 (dppf) (96 mg, 0.13 mmol) and phenyl boronic acid (64 mg, 0.52 mmol) were then added and the reaction mixture was heated at 90° C. overnight. The reaction mixture was filtered, filtrate was then diluted with water and the product was extracted with ethyl acetate. The organic layer was washed with saturated brine solution, dried over sodium sulphate and concentrated to afford 29 mg (13.3% yield) of 5-phenyl-pyrazine-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity: 93.2%. 1H NMR (CDCl3): δ 9.4 (d, 1H), 9.0 (d, 1H), 8.7-8.6 (m, 1H), 8.1-8.0 (m, 2H), 7.8-7.7 (d, 1H), 7.7-7.5 (m, 5H), 7.4-7.3 (d, 1H), 4.46-4.18 (m, 2H), 4.46-4.18 (m, 2H), 4.1-3.86 (m, 2H), 3.8-3.5 (m, 4H), 3.5-3.4 (m, 1H), 3.3-3.2 (m, 2H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. additionfiltrate was then diluted with water
  3. extractionthe product was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine solution
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4572b2ea971f4c5a8261486653fc7432
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

Loading…