Dimethylformamide → HCID 19994642, compound

HRID 2248577Notes

Reaction equation

HRID 2248577 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([N:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)=[N:7][NH:8]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:24][CH2:25][CH2:26][CH2:27][N:28]1[C:32](=[O:33])[C:31]([CH3:35])([CH3:34])[S:30][CH2:29]1.CN(C)C=O>O>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([N:11]3[CH2:12][CH2:13][N:14]([CH2:24][CH2:25][CH2:26][CH2:27][N:28]4[C:32](=[O:33])[C:31]([CH3:34])([CH3:35])[S:30][CH2:29]4)[CH2:15][CH2:16]3)=[N:7][NH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 98158716-fluoro-3-piperazin-1-yl-1H-indazoleHCID 106117723-(4-Bromobutyl)-5,5-dimethyl-4-thiazolidinone

Product 1

HCID 19994642HCID 19994642, compoundYield 34.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 6-fluoro-3-(1-piperazinyl)-1H-indazole (4.4 g), K2CO3 (2.8 g), 3-(4-bromobutyl)-5,5-dimethyl-4-thiazolidinone (6.6 g) and dimethylformamide (75 ml) was heated at 75° for 4 hours. The reaction was poured into H2O, and the aqueous mixture extracted with ethyl acetate. The ethyl acetate was washed (H2O), dried (MgSO4) and the solvent concentrated to afford an oil. Upon standing the oil crystallized, and when the mass was triturated with ether, 3.3 g of a solid was collected. The compound was recrystallized from toluene-hexane to yield 2.8 g of 3-(4-(1-[6-fluoro-1H-indazol-3-yl]-4-piperazinyl)-butyl)-5,5-dimethyl-4-thiazolidinone, m.p. 123°-125° C.

Workup

  1. temperaturewas heated at 75° for 4 hours
  2. extractionthe aqueous mixture extracted with ethyl acetate
  3. washThe ethyl acetate was washed (H2O)
  4. dry with materialdried (MgSO4)
  5. concentrationthe solvent concentrated
  6. customto afford an oil
  7. customcrystallized
  8. customwhen the mass was triturated with ether, 3.3 g of a solid
  9. customwas collected
  10. customThe compound was recrystallized from toluene-hexane

Sources & evidence

ORD record
ord-62d0baf7b8bd4f2b85222b78258137da
Source dataset
uspto-grants-1991_08
Patent number
US05041445

Reaction notes

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