p-Toluenesulfonic acid → HCID 15896315, compound

HRID 968215Notes

Reaction equation

HRID 968215 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][C:9](OCC)=[O:10])=[C:6]([NH:14]CC2C=CC(OC)=CC=2OC)[N:5]=[C:4]([S:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[C:29]=2[F:35])[N:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]2[CH2:8][C:9](=[O:10])[NH:14][C:6]=2[N:5]=[C:4]([S:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[C:29]=2[F:35])[N:3]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 86601100HCID 86601100, compound

Product 1

HCID 15896315HCID 15896315, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of the product from example 1, step (d) (0.5 g) in dry toluene (50 ml) containing p-toluene sulphonic acid (25 mg) was heated under reflux for 4 hours. [Analysis of the reaction mixture by 1 c/ms indicated cyclisation was complete but with loss of the acid labile dimethoxybenzyl adduct.] The reaction mixture was evaporated to dryness and the residue purified by chromatography on silica eluting with ethyl acetate to afford the subtitle compound (0.20 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. custom] The reaction mixture was evaporated to dryness
  4. customthe residue purified by chromatography on silica eluting with ethyl acetate

Sources & evidence

ORD record
ord-f8fb41be458f4eb995e8a43a59483130
Source dataset
uspto-grants-2005_10
Patent number
US06958344B2

Reaction notes

Loading…