Potassium Hydroxide → HCID 178456993, compound
Reaction equation
[OH-].[K+].Cl[C:4]1[S:12][C:11]2[S:10](=[O:14])(=[O:13])[N:9]=[C:8]([NH:15][CH:16]([CH3:18])[CH3:17])[NH:7][C:6]=2[CH:5]=1>CO.[Pd]>[CH:16]([NH:15][C:8]1[NH:7][C:6]2[CH:5]=[CH:4][S:12][C:11]=2[S:10](=[O:13])(=[O:14])[N:9]=1)([CH3:18])[CH3:17]Participants
Procedure
Powdered potassium hydroxide (128 mg, 2.28 mmol) was added to a solution of 6-chloro-3-isopropylamino-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide (319 mg, 1.14 mmol) in 25 ml of methanol and the mixture was hydrogenated at room temperature and atmospheric pressure for 3 days with 150 mg of 10% palladium on carbon. The catalyst was removed by filtration and washed with ethanol and water. The combined filtrate was acidified with 4 M hydrochloric acid and evaporated to dryness. The residue was recrystallised from water/ethanol and finally from ethyl acetate with decolorising charcoal affording the title compound contaminated with starting material, which could be removed by silica gel column chromatography; 1H-NMR (DMSO-d6): δ1.16 (d, 6H, 2×CH3), 3.88 (m, 1H, CH), 6.95 (d, 1H, H-5), 7.03 (br d, 1H, NH), 7.88 (d, 1H, H-6), 10.70 (br s, 1H).
Workup
- customwas hydrogenated at room temperature
- customThe catalyst was removed by filtration
- washwashed with ethanol and water
- customevaporated to dryness
- customThe residue was recrystallised from water/ethanol and finally from ethyl acetate with decolorising charcoal affording the title compound
- customcould be removed by silica gel column chromatography
Sources & evidence
- ORD record
- ord-cbf5d864f47b4ffdac1d29e8061750fe
- Source dataset
- uspto-grants-2001_05
- Patent number
- US06225310B1
Reaction notes
Loading…