Sodium Carbonate → HCID 59559590, compound

HRID 1177893Notes

Reaction equation

HRID 1177893 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[N:14]=[N:15][C:16](Cl)=[CH:17][CH:18]=1)=[O:12].[C:38]1(B(O)O)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>CN(C=O)C.O.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[N:14]=[N:15][C:16]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[CH:17][CH:18]=1)=[O:12]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 86634091HCID 86634091, compound

Product 1

HCID 59559590HCID 59559590, compoundYield 12%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Na2CO3 (183 mg, 1.73 mmol) was added to a stirred solution of 6-chloro-pyridazine-3-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide (263 mg, 0.57 mmol) in DMF (6 mL). PdCl2 (dppf) (80.4 mg, 0.11 mmol) and phenyl boronic acid (89.9 mg, 0.69 mmol) were then added and the reaction mixture was heated at 80° C. for 2 hrs. The reaction mixture was 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 get the residue. The residue obtained was purified by preparative HPLC afford 34 mg (11% yield) of 6-Phenyl-pyridazine-3-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity: 93.2%. 1H NMR (DMSO-d6): δ 9.3 (t, 1H), 8.5 (d, 1H), 8.3 (t, 3H), 8.0-7.5 (m, 7H), 4.4 (d, 2H), 3.8 (d, 4H), 3.46 (bs, 2H), 3.2 (d, 2H).

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine solution
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated
  5. customto get the residue
  6. customThe residue obtained
  7. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-d2544045e5a140028e4be0a76f2aac59
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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