Hydrochloric Acid → 2-[4-(4-Acetyl-benzenesulfonyl)-piperazin-1-yl]-thiazole-5-carboxylic acid hydroxyamide

HRID 1392948ノート

反応式

HRID 1392948 の反応式
C[O:2][C:3]([C:5]1[S:9][C:8]([N:10]2[CH2:15][CH2:14][N:13]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25](=[O:27])[CH3:26])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH2:12][CH2:11]2)=[N:7][CH:6]=1)=O.Cl.[NH2:29][OH:30].C[O-].[Na+].CO.Cl>O1CCOCC1>[OH:30][NH:29][C:3]([C:5]1[S:9][C:8]([N:10]2[CH2:15][CH2:14][N:13]([S:16]([C:19]3[CH:20]=[CH:21][C:22]([C:25](=[O:27])[CH3:26])=[CH:23][CH:24]=3)(=[O:18])=[O:17])[CH2:12][CH2:11]2)=[N:7][CH:6]=1)=[O:2]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 692013072-[4-(4-Acetyl-benzenesulfonyl)-piperazin-1-yl]-thiazole-5-carboxylic acid methyl ester

生成物 1

HCID 113957682-[4-(4-Acetyl-benzenesulfonyl)-piperazin-1-yl]-thiazole-5-carboxylic acid hydroxyamide収率 12%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

To a solution of compound (12h) (125 mg, 0.305 mmol) in 1,4-dioxane (2 mL) were added hydroxylamine hydrochloride (211 mg, 3.05 mmol) and a freshly prepared solution of sodium methoxide in methanol (105 mg, 4.57 mmol of sodium dissolved in 1 mL of methanol) under a N2 atmosphere. The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was acidified to pH˜6 with 1M HCl and the formed precipitates were filtered off. The filtrate was diluted with ethyl acetate (5 mL) and water (2 mL) and the organic layer was separated. The aqueous layer was washed with ethyl acetate (5 mL) and the combined organic layers were dried on sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by preparative HPLC to give 13 h (15 mg, yield 12.0%). HPLC: 92.26% (Rt=12.51 min).

後処理

  1. customthe formed precipitates
  2. filtrationwere filtered off
  3. additionThe filtrate was diluted with ethyl acetate (5 mL) and water (2 mL)
  4. customthe organic layer was separated
  5. washThe aqueous layer was washed with ethyl acetate (5 mL)
  6. customthe combined organic layers were dried on sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by preparative HPLC
  10. customto give 13 h (15 mg, yield 12.0%)

出典と根拠

ORDレコード
ord-aa264ed95b5846b1b6d3e88b8a69d796
出典データセット
uspto-grants-2008_03
特許番号
US07345043B2

反応ノート

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