Acetone → 2-(4-Chloro-phenyl)-5H-thiazolo[5,4-c]pyridin-4-one

HRID 554866Notes

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)=CC=4OC)[CH:13]=[CH:14][C:15]=3[N:16]=2)=[CH:4][CH:3]=1.O.C([O-])(O)=O.[Na+].CC(C)=O>FC(F)(F)C(O)=O>[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][CH:13]=[CH:14][C:15]=3[N:16]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Mix 2-(4-chloro-phenyl)-5-(2,4-dimethoxy-benzyl)-5H-thiazolo[5,4-c]pyridin-4-one (24.6 g, 59.6 mmol) in trifluoroacetic acid (143 mL) and heat at 70° C. for 2 h. Cool the mixture to room temperature and add water (325 mL) and saturated NaHCO3 (710 mL) with stirring. Add acetone (180 mL) and stir the resulting slurry for one hour at room temperature. Filter and wash the solids with water (110 mL) and then acetone (110 mL). Dry the solids in a vacuum oven at 60° C. overnight. Triturate the solids three times with CH3CN (700 mL) at 60° C. and filter. Dry the solids in a vacuum oven at 60° C. overnight to obtain 18.3 g (117%) of the title compound that still contains salt impurities. 1H NMR (400 MHz, DMSO-d6) δ11.86 (s, 1H), 8.12 (d, 2H, J=8.2), 7.65 (d, 2H, J=8.7), 7.49 (t, 1H, J=6.0), 6.91 (1H, J=6.6).

Workup

temperatureCool the mixture to room temperature
filtrationFilter
washwash the solids with water (110 mL)
customDry the solids in a vacuum oven at 60° C. overnight
customTriturate the solids three times with CH3CN (700 mL) at 60° C.
filtrationfilter
customDry the solids in a vacuum oven at 60° C. overnight

Sources & evidence

ORD record: ord-3be49514f2034c9c9c366f52ba27e10a
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08049013B2

Reaction notes

Loading…