1,3-Cyclohexanedione → HCID 178515825, compound

HRID 1696672Notes

Reaction equation

HRID 1696672 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][NH:4][N:3]=1.[F:7][C:8]1[C:16]2[N:15]=[C:14]([S:17][C:18]3[O:22][C:21]([CH:23]=O)=[CH:20][CH:19]=3)[NH:13][C:12]=2[CH:11]=[C:10]([F:25])[CH:9]=1.[C:26]1(=O)[CH2:31][CH2:30][CH2:29][C:28](=[O:32])[CH2:27]1>C(O)CCC>[F:25][C:10]1[CH:9]=[C:8]([F:7])[C:16]2[NH:15][C:14]([S:17][C:18]3[O:22][C:21]([CH:23]4[C:27]5[C:28](=[O:32])[CH2:29][CH2:30][CH2:31][C:26]=5[NH:1][C:2]5=[N:3][NH:4][CH:5]=[C:6]45)=[CH:20][CH:19]=3)=[N:13][C:12]=2[CH:11]=1

Participants

5

Reactant 3

HCID 104341,3-CyclohexanedioneHCID 86623886HCID 86623886, compoundHCID 178418806HCID 178418806, compound

Product 1

HCID 178515825HCID 178515825, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 3-aminopyrazole (0.089 g, 1.07 mmol), 5-(4,6-difluoro-1H-benzimidazol-2-ylsulfanyl)-furan-2-carbaldehyde (described in example 142, 0.30 g, 1.07 mmol) and 1,3-cyclohexanedione (0.12 g, 1.07 mmol) in 5 ml of 1-butanol is heated at reflux temperature for 3 hours. The reaction mixture is then concentrated under reduced pressure and the residue is purified on a silica gel column (40 g) eluted with a mixture of cyclohexane and ethyl acetate (2/8, v/v). The fractions containing the expected product are concentrated under reduced pressure and the obtained solid is washed with pentane (25 ml) and diisopropylether (25 ml) and dried under vacuum to yield 323 mg of 4-[5-(5,7-difluoro-1H-benzimidazol-2-ylsulfanyl)-furan-2-yl]-2,4,6,7,8,9-hexahydro-pyrazolo[3,4-b]quinolin-5-one as a white powder. Yield=69%. Analytical LC/MS (method C): m/z=438 (negative ion mode [M−H]−), m/z=440 (positive ion mode [M+H]+)

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 3 hours
  3. concentrationThe reaction mixture is then concentrated under reduced pressure
  4. customthe residue is purified on a silica gel column (40 g)
  5. washeluted with a mixture of cyclohexane and ethyl acetate (2/8, v/v)
  6. additionThe fractions containing the expected product
  7. concentrationare concentrated under reduced pressure
  8. washthe obtained solid is washed with pentane (25 ml) and diisopropylether (25 ml)
  9. customdried under vacuum

Sources & evidence

ORD record
ord-2ab09df66c35440dace105356d90238d
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

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