Pyrazole → HCID 21949919, compound

HRID 2114646Notes

Reaction equation

HRID 2114646 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.Br[CH2:7][C:8]1[N:12]([CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[N:11]=[C:10]([CH2:23][CH3:24])[C:9]=1[O:25][C:26]1[CH:31]=[C:30]([Cl:32])[CH:29]=[C:28]([Cl:33])[CH:27]=1.[H-].[Na+]>CN(C)C=O>[Cl:33][C:28]1[CH:27]=[C:26]([CH:31]=[C:30]([Cl:32])[CH:29]=1)[O:25][C:9]1[C:10]([CH2:23][CH3:24])=[N:11][N:12]([CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C:8]=1[CH2:7][N:1]1[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 1048PyrazoleHCID 24758Sodium hydrideHCID 21949785HCID 21949785, compound

Product 1

HCID 21949919HCID 21949919, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Pyrazole (23 mg, 0.330 mmol) was added in one portion to a stirred solution of the bromide of Example 137 (148 mg, 0.300 mmol) and sodium hydride (60% dispersion in oil, 13.2 mg, 0.330 mmol) in N,N-dimethylformamide (2 ml) at room temperature under nitrogen. The reaction was stirred for 5 hours, quenched with water (1.00 ml) and concentrated under reduced pressure. The residue was dissolved in dichloromethane (30 ml) and the resulting solution was washed with 1M aqueous potassium carbonate solution (10 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (98:2, by volume) to provide the title compound (125 mg) as a colourless oil.

Workup

  1. customquenched with water (1.00 ml)
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in dichloromethane (30 ml)
  4. washthe resulting solution was washed with 1M aqueous potassium carbonate solution (10 ml)
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (98:2, by volume)

Sources & evidence

ORD record
ord-425c207aa6e547b4b960c35504afe78d
Source dataset
uspto-grants-2008_10
Patent number
US07435728B2

Reaction notes

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