Acetic Acid → 2,3-Dichloro-N-[5-(hydroxymethyl)-3-(3-pyridinylmethoxy)-2-pyrazinyl]benzenesulphonamide

HRID 1444042노트

반응식

HRID 1444042 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:9]=1[S:15]([NH:18][C:19]1[N:20]=[CH:21][C:22]([C:33](OC)=[O:34])=[N:23][C:24]=1[O:25][CH2:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)(=[O:17])=[O:16].C(O)(=O)C>O1CCCC1>[Cl:7][C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:9]=1[S:15]([NH:18][C:19]1[C:24]([O:25][CH2:26][C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)=[N:23][C:22]([CH2:33][OH:34])=[CH:21][N:20]=1)(=[O:17])=[O:16]

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 21226445Aluminium lithium hydrideHCID 59168105HCID 59168105, 화합물

생성물 1

HCID 591682022,3-Dichloro-N-[5-(hydroxymethyl)-3-(3-pyridinylmethoxy)-2-pyrazinyl]benzenesulphonamide수율 42.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-65 °C

실험 절차

Lithium aluminium hydride (0.85 mL of a 1M solution in tetrahydrofuran) was added dropwise to 5-(2,3-dichlorobenzenesulphonylamino)-6-(3-pyridinylmethoxy)pyrazine-2-carboxylic acid, methyl ester (Example 134) (0.2 g) in tetrahydrofuran (10 mL) cooled to −65° C. The reaction mixture was allowed to warm to room temperature and stirred for 1h. Aqueous acetic acid was added and the mixture extracted with ethyl acetate. The organic solution was dried (MgSO4) and evaporated. Chromatography on silica gel eluting with ethyl acetate/methanol mixtures gave the title compound (0.08 g).

후처리

  1. temperatureto warm to room temperature
  2. extractionthe mixture extracted with ethyl acetate
  3. dry with materialThe organic solution was dried (MgSO4)
  4. customevaporated

출처 및 근거

ORD 기록
ord-34fa62a8e8954656841e510c9930ab45
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07662825B2

반응 노트

불러오는 중…