Methyl iodide → 5-Chlorothieno[3,2-b]pyridine-2-sulfonic acid [1-(3-cyanobenzyl)-2-oxo-pyrrolidin-3-(S)-yl]-methylamide

HRID 2763

반응식

HRID 2763 반응식
[C:1]([C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][CH:29]=1)[CH2:6][N:7]1[CH2:11][CH2:10][C@H:9]([NH:12][S:13]([C:16]2[S:24][C:23]3[C:18](=[N:19][C:20]([Cl:25])=[CH:21][CH:22]=3)[CH:17]=2)(=[O:15])=[O:14])[C:8]1=[O:26])#[N:2].CI.[H-].[Na+].[CH3:34]COC(C)=O>CN(C=O)C>[C:1]([C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][CH:29]=1)[CH2:6][N:7]1[CH2:11][CH2:10][C@H:9]([N:12]([CH3:34])[S:13]([C:16]2[S:24][C:23]3[C:18](=[N:19][C:20]([Cl:25])=[CH:21][CH:22]=3)[CH:17]=2)(=[O:15])=[O:14])[C:8]1=[O:26])#[N:2]

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 543133655-Chlorothieno[3,2-b]pyridine-2-sulfonic acid [1-(3-cyanobenzyl)-2-oxo-pyrrolidin-3-(S)-yl]-amide

생성물 1

HCID 538582545-Chlorothieno[3,2-b]pyridine-2-sulfonic acid [1-(3-cyanobenzyl)-2-oxo-pyrrolidin-3-(S)-yl]-methylamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

5-Chlorothieno[3,2-b]pyridine-2-sulfonic acid [1-(3-cyanobenzyl)-2-oxo-pyrrolidin-3-(S)-yl]-amide (0.25 g, 0.56 mmol) is dissolved in 6 mL of DMF and cooled to 0° C. To the solution is added methyl iodide (0.40 g, 2.82 mmol) and sodium hydride (25 mg of a 60% dispersion in mineral oil, 0.62 mmol). The reaction mixture is allowed to warm to room temperature and is stirred for 2 h. At this time, the solution is diluted with and EtOAc and the layers are separated. The organic layer is washed with 1N HCl, H2O, saturated NaHCO3 solution and saturated NaCl. The organic phase is then dried over MgSO4, filtered and concentrated to give the title compound (0.25 g, 0.54 mmol) as a solid.

후처리

  1. temperatureto warm to room temperature
  2. customthe layers are separated
  3. washThe organic layer is washed with 1N HCl, H2O, saturated NaHCO3 solution and saturated NaCl
  4. dry with materialThe organic phase is then dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e34502d7c6c04c4ba22048fd23ff4bf0
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05731315

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