2,5-Hexanedione → HCID 68941558, compound

HRID 1024653Notes

Reaction equation

HRID 1024653 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=3)[C:10](=[O:27])[C:11]3[CH:16]=[N:15][N:14]([C:17]4[CH:18]=[C:19]([S:23]([NH2:26])(=[O:25])=[O:24])[CH:20]=[CH:21][CH:22]=4)[C:12]=3[N:13]=2)=[CH:4][CH:3]=1.[CH3:35][C:36](=O)[CH2:37][CH2:38][C:39](=O)[CH3:40].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=3)[C:10](=[O:27])[C:11]3[CH:16]=[N:15][N:14]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([S:23]([N:26]5[C:39]([CH3:40])=[CH:38][CH:37]=[C:36]5[CH3:35])(=[O:24])=[O:25])[CH:18]=4)[C:12]=3[N:13]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 80352,5-HexanedioneHCID 521998p-Toluenesulfonic acid monohydrateHCID 24782073HCID 24782073, compound

Product 1

HCID 68941558HCID 68941558, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-[6-(4-bromo-phenyl)-5-(4-chloro-phenyl)-4-oxo-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-1-yl]-benzene sulfonamide (prepared as described in example 6, 10.00 g, 17.95 mmol), hexane-2,5-dione (6.14 g, 53.9 mmol), and p-toluenesulfonic acid monohydrate (1.000 g, 5.257 mmol) in dry toluene (250 mL) is heated to reflux in a Dean-Stark apparatus for 18 h. The reaction mixture is concentrated and the residue obtained is stirred in ethyl acetate and filtered. About 7.1 g of starting material is recovered. Concentration of the filtrate afforded the crude product. It is then purified by column chromatography (silica gel, 60-120 mesh) to afford the 6-(4-bromo-phenyl)-5-(4-chloro-phenyl)-1-[3-(2,5-dimethyl-pyrrole-1-sulfonyl)-phenyl]-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one.

Workup

  1. temperatureis heated
  2. temperatureto reflux in a Dean-Stark apparatus for 18 h
  3. concentrationThe reaction mixture is concentrated
  4. customthe residue obtained
  5. filtrationfiltered
  6. customAbout 7.1 g of starting material is recovered
  7. customConcentration of the filtrate afforded the crude product
  8. customIt is then purified by column chromatography (silica gel, 60-120 mesh)

Sources & evidence

ORD record
ord-a996c9c31aec4e24abd1e63b9f88eb67
Source dataset
uspto-grants-2014_05
Patent number
US08722691B2

Reaction notes

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