Water → HCID 86686312, compound

HRID 1043872Notes

Reaction equation

HRID 1043872 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]3[CH2:17][CH2:16][O:15][CH2:14]3)[N:11]=[CH:10][C:9]=2[C:18]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:23]=2[O:30][CH3:31])=[O:19])=[C:4](Cl)[CH:3]=1.O>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[N:12]([CH:13]4[CH2:17][CH2:16][O:15][CH2:14]4)[N:11]=[CH:10][C:9]=3[C:18](=[O:19])[N:20]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:23]=3[O:30][CH3:31])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 962WaterHCID 86686311HCID 86686311, compound

Product 1

HCID 86686312HCID 86686312, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(±)-5-(4-bromo-2-chlorophenyl)-N-(2,4-dimethoxybenzyl)-1-(tetrahydrofuran-3-yl)-1H-pyrazole-4-carboxamide (1.26 g) was dissolved in THF (25 mL), and KTB (597 mg) was added at 0° C. The mixture was stirred for 12 hours while gradually warming to room temperature. The reaction mixture was cooled to 0° C., and water was added, followed by filtration. The filtration residue was separately stored. The filtrate was extracted with ethyl acetate, and the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 10% to 70%). The resulting fraction and the filtration residue obtained above were combined and concentrated to give the title compound (488 mg).

Workup

  1. additionKTB (597 mg) was added at 0° C
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. filtrationfollowed by filtration
  4. extractionThe filtrate was extracted with ethyl acetate
  5. concentrationthe organic layer was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 10% to 70%)
  7. customThe resulting fraction and the filtration residue obtained
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-9f4cef0798a44af2bc9f0f2f34c9c81e
Source dataset
uspto-grants-2013_10
Patent number
US08563565B2

Reaction notes

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