Hydrochloric Acid → {3-[(Pyridine-3-sulfonylamino)-methyl]-phenyl}acetic acid methyl ester

HRID 842746노트

반응식

HRID 842746 반응식
Cl.[CH3:2][O:3][C:4](=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][NH2:13])[CH:7]=1.C(NC(C)C)(C)C.[N:22]1[CH:27]=[CH:26][CH:25]=[C:24]([S:28](Cl)(=[O:30])=[O:29])[CH:23]=1.Cl>ClCCl>[CH3:2][O:3][C:4](=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][NH:13][S:28]([C:24]2[CH:23]=[N:22][CH:27]=[CH:26][CH:25]=2)(=[O:30])=[O:29])[CH:7]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 3164136Pyridine-3-sulfonyl chlorideHCID 21185371Methyl 2-[3-(aminomethyl)phenyl]acetate hydrochloride

생성물 1

HCID 54480791{3-[(Pyridine-3-sulfonylamino)-methyl]-phenyl}acetic acid methyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (3-aminomethyl-phenyl)-acetic acid methyl ester hydrochloride (0.56 g) and diisopropylamine (2.2 mL) in 10 mL dichloromethane was added pyridine-3-sulfonyl chloride (0.601 g, 2.83 mmol) and the reaction was stirred at room temperature for 16 h. Aqueous 1N HCl was added and the solution was extracted with CH2Cl2. The organic solution was washed with saturated NaHCO3, dried over MgSO4, filtered and concentrated in vacuo to afford the title compound. Purification via flash chromatography on silica gel (2:1 hexanes: EtOAc) afforded the title compound as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.91 (s, 1H), 8.71 (d, 1H), 8.04 (d, 1H), 7.37 (m, 1H), 7.05-7.24 (m, 4H), 5.87 (bs, 1H), 4.14 (s, 1H), 2H), 3.62 (s, 3H), 3.52 (s, 2H).

후처리

  1. extractionthe solution was extracted with CH2Cl2
  2. washThe organic solution was washed with saturated NaHCO3
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-1d4cfda45efb4b759715795e1a543993
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06376502B1

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