Hydrochloric Acid → 2-[4-(5-Dimethylamino-naphthalene-1-sulfonyl)-piperazin-1-yl]-thiazole-5-carboxylic acid hydroxyamide

HRID 1392953

반응식

HRID 1392953 반응식
CO[C:3]([C:5]1[S:9][C:8]([N:10]2[CH2:15][CH2:14][N:13]([S:16]([C:19]3[C:28]4[C:23](=[C:24]([N:29]([CH3:31])[CH3:30])[CH:25]=[CH:26][CH:27]=4)[CH:22]=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH2:12][CH2:11]2)=[N:7][CH:6]=1)=[O:4].Cl.[NH2:33][OH:34].C[O-].[Na+].CO.Cl>O1CCOCC1>[OH:34][NH:33][C:3]([C:5]1[S:9][C:8]([N:10]2[CH2:15][CH2:14][N:13]([S:16]([C:19]3[C:28]4[C:23](=[C:24]([N:29]([CH3:30])[CH3:31])[CH:25]=[CH:26][CH:27]=4)[CH:22]=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH2:12][CH2:11]2)=[N:7][CH:6]=1)=[O:4]

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 691997234-(5-Dimethylamino-naphthalene-1-sulfonyl)-piperazin-1-yl-thiazole-5-carboxylic acid methyl ester

생성물 1

HCID 111554392-[4-(5-Dimethylamino-naphthalene-1-sulfonyl)-piperazin-1-yl]-thiazole-5-carboxylic acid hydroxyamide수율 8%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

To a solution of compound (12k) (125 mg, 0.270 mmol) in 1,4-dioxane (2 mL) were added hydroxylamine hydrochloride (187 mg, 2.70 mmol) and a freshly prepared solution of sodium methoxide in methanol (92 mg, 4.00 mmol of sodium dissolved in 1 mL of methanol) under a N2 atmosphere. The reaction mixture was stirred at room temperature for 2 h (progress of the reaction was monitored by TLC analysis). 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 13k (10 mg, yield 8.0%). HPLC: 90.69% (Rt=12.77 min).

후처리

  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

출처 및 근거

ORD 기록
ord-ed097858cb66406d8f9d0b7f7ceaed99
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07345043B2

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