Potassium Hydroxide → HCID 178456993、化合物

HRID 1975929ノート

反応式

HRID 1975929 の反応式
[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]

参加物

5

反応物 2

HCID 14797Potassium HydroxideHCID 1784569956-chloro-1,1-dioxo-N-propan-2-yl-4H-thieno[3,2-e][1,2,4]thiadiazin-3-amine

生成物 1

HCID 178456993HCID 178456993、化合物

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

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).

後処理

  1. customwas hydrogenated at room temperature
  2. customThe catalyst was removed by filtration
  3. washwashed with ethanol and water
  4. customevaporated to dryness
  5. customThe residue was recrystallised from water/ethanol and finally from ethyl acetate with decolorising charcoal affording the title compound
  6. customcould be removed by silica gel column chromatography

出典と根拠

ORDレコード
ord-cbf5d864f47b4ffdac1d29e8061750fe
出典データセット
uspto-grants-2001_05
特許番号
US06225310B1

反応ノート

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