Acetohydrazide → (S)-N'-acetyl-8-chloro-3-(1-(1,3-dioxoisoindolin-2-yl)-ethyl)quinoline-2-carbohydrazide

HRID 2044897노트

반응식

HRID 2044897 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12](O)=[O:13])[C:8]([C@@H:15]([N:17]1[C:25](=[O:26])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]1=[O:27])[CH3:16])=[CH:7]2.C(=O)(O)[O-].[Na+].[C:33]([NH:36][NH2:37])(=[O:35])[CH3:34]>CN(C=O)C.C(OCC)(=O)C.O>[C:33]([NH:36][NH:37][C:12]([C:9]1[C:8]([C@@H:15]([N:17]2[C:18](=[O:27])[C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:25]2=[O:26])[CH3:16])=[CH:7][C:6]2[C:11](=[C:2]([Cl:1])[CH:3]=[CH:4][CH:5]=2)[N:10]=1)=[O:13])(=[O:35])[CH3:34]

참가 물질

7

반응물 3

HCID 14039AcetohydrazideHCID 516892Sodium BicarbonateHCID 57707755(S)-8-chloro-3-(1-(1,3-dioxoisoindolin-2-yl)ethyl)-quinoline-2-carboxylic acid

생성물 1

HCID 57707959(S)-N'-acetyl-8-chloro-3-(1-(1,3-dioxoisoindolin-2-yl)-ethyl)quinoline-2-carbohydrazide

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of (S)-8-chloro-3-(1-(1,3-dioxoisoindolin-2-yl)ethyl)-quinoline-2-carboxylic acid (100 mg, 0.26 mmol) in DMF (3.0 mL) was added sodium bicarbonate (66 mg, 0.79 mmol), hoat (54 mg, 0/39 mmol), acetic hydrazide (23 mg, 0.31 mmol) and edc (76 mg, 0.39 mmol). The reaction was stirred at r.t. for 2 hours and then it was diluted with ethyl acetate (60 mL) and water (20 mL). The separated aqueous layer was extracted with ethyl acetate (30 mL) and the combined organic layers were washed with LiCl (1.0 M aqueous solution, 30 mL), brine (30 mL) and then dried (MgSO4), filtered and evaporated in vacuo to give (S)—N′-acetyl-8-chloro-3-(1-(1,3-dioxoisoindolin-2-yl)ethyl)-quinoline-2-carbohydrazide.1H NMR (400 MHz, CDCl3) δ ppm 10.45 (1H, s), 8.88 (1H, s), 8.64 (1H, s), 7.70-7.84 (4H, m), 7.64-7.66 (2H, m), 7.52 (1H, dd, J=5.3, 2.9 Hz), 6.87 (1H, q, J=7.0 Hz), 2.13 (3H, s), 1.98 (3H, d, J=7.0 Hz). Mass Spectrum (ESI) m/e=437.0 (M+1).

후처리

  1. extractionThe separated aqueous layer was extracted with ethyl acetate (30 mL)
  2. washthe combined organic layers were washed with LiCl (1.0 M aqueous solution, 30 mL), brine (30 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-df279f90f032450e884a5a7c191cb17c
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586739B2

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