p-Toluenesulfonic acid → HCID 178481364, compound

HRID 559190Notes

Reaction equation

HRID 559190 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:34](=[O:35])[N:33]([CH3:36])[C:11]3[N:12]([CH3:32])[C:13]4[C:18]([C:10]=3[CH:9]=2)=[CH:17][C:16]([C:19]2[NH:20][N:21]=[C:22]([CH2:24][O:25]C3CCCCO3)[CH:23]=2)=[CH:15][CH:14]=4)=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:34](=[O:35])[N:33]([CH3:36])[C:11]3[N:12]([CH3:32])[C:13]4[C:18]([C:10]=3[CH:9]=2)=[CH:17][C:16]([C:19]2[NH:20][N:21]=[C:22]([CH2:24][OH:25])[CH:23]=2)=[CH:15][CH:14]=4)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 178481363HCID 178481363, compound2×

Product 1

HCID 178481364HCID 178481364, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

110 mg (0.2 mmol) of compound from Example 86 above, 3-(4-bromophenyl)-1,9-dimethyl-6-[5-(tetrahydropyran-2-yloxymethyl)-2H-pyrazol-3-yl]-1,9-dihydropyrido[2,3-b]indol-2-one are dissolved in 6 ml of MeOH. A spatula tip of p-toluenesulphonic acid is added and the mixture is refluxed overnight. The reaction medium is evaporated to dryness. A saturated NaHCO3 solution is added and the mixture is extracted with EtOAc. The organic phase is evaporated to dryness. The product obtained is triturated in water, filtered and washed with water. The product is taken up in methanol and evaporated to dryness.

Workup

  1. temperaturethe mixture is refluxed overnight
  2. customThe reaction medium is evaporated to dryness
  3. additionA saturated NaHCO3 solution is added
  4. extractionthe mixture is extracted with EtOAc
  5. customThe organic phase is evaporated to dryness
  6. customThe product obtained
  7. customis triturated in water
  8. filtrationfiltered
  9. washwashed with water
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-9c8317c973994e8186db99cf244617e5
Source dataset
uspto-grants-2011_11
Patent number
US08063061B2

Reaction notes

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