p-Toluenesulfonic acid → 2-(4-Chloro-phenyl)-6,7-dihydro-5H-thiazolo[5,4-c]pyridin-4-one

HRID 601523Notes

Reaction equation

HRID 601523 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[C:11](=[O:28])[N:12](CC4C=CC(OC)=C(OC)C=4)[CH2:13][CH2:14][C:15]=3[N:16]=2)=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[C:11](=[O:28])[NH:12][CH2:13][CH2:14][C:15]=3[N:16]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 575017402-(4-chloro-phenyl)-5-(3,4-dimethoxy-benzyl)-6,7-dihydro-5H-thiazolo[5,4-c]pyridin-4-one

Product 1

HCID 575017522-(4-Chloro-phenyl)-6,7-dihydro-5H-thiazolo[5,4-c]pyridin-4-oneYield 70.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Dissolve 2-(4-chloro-phenyl)-5-(3,4-dimethoxy-benzyl)-6,7-dihydro-5H-thiazolo[5,4-c]pyridin-4-one (376 mg, 0.91 mmol) in toluene (5.0 mL) and treat with para-toluene sulfonic acid (176 mg, 0.92 mmol). Stir the solution at reflux for 2 d, then concentrate and purify the crude material by flash chromatography, using 5% MeOH (2N NH3)/CH2Cl2 as eluent, to give the title compound as a white solid (170 mg, 70%). MS (ES+) 265.0 (M+1)+. 1H NMR (CDCl3): δ 8.02 (d, 2H, J=8.8 Hz), 7.94 (s, 1H), 7.60 (d, 2H, J=8.4 Hz), 3.52 (dt, 2H, J=7.1, 2.5 Hz), 3.04 (t, 2H, J=7.3 Hz).

Workup

  1. temperatureat reflux for 2 d
  2. concentrationconcentrate
  3. custompurify the crude material by flash chromatography

Sources & evidence

ORD record
ord-a522cdada2a64faf9258ef8379d6a0e8
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

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