Dimethylacetamide → N-methyl-N-[4-methyl-2-(1,3-thiazol-2-yl)-1H-indol-7-yl]thiophene-2-sulfonamide

HRID 1851571노트

반응식

HRID 1851571 반응식
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N:11]([CH3:20])[S:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)(=[O:14])=[O:13])=[C:7]2[C:3]=1[CH:4]=[C:5]([C:21](=[S:23])[NH2:22])[NH:6]2.Br[CH2:25][CH:26](OCC)OCC.CN(C)C(=O)C>C(OCC)(=O)C>[CH3:20][N:11]([C:8]1[CH:9]=[CH:10][C:2]([CH3:1])=[C:3]2[C:7]=1[NH:6][C:5]([C:21]1[S:23][CH:25]=[CH:26][N:22]=1)=[CH:4]2)[S:12]([C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)(=[O:14])=[O:13]

참가 물질

5

반응물 3

HCID 31374DimethylacetamideHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 574760084-methyl-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carbothioamide

생성물 1

HCID 57901591N-methyl-N-[4-methyl-2-(1,3-thiazol-2-yl)-1H-indol-7-yl]thiophene-2-sulfonamide수율 43%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

A mixed solution of 4-methyl-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carbothioamide (0.20 g), 1-bromo-2,2-diethoxyethane (0.23 mL) and N,N-dimethylacetamide (10 ml) was stirred at 100° C. for 6 hr. The reaction solution was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=25:75-35:65), and the obtained oil was crystallized from ethyl acetate-hexane to give the title compound (92 mg, yield 43%) as pale-yellow prism crystals. melting point 159-160° C.

후처리

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customthe obtained oil was crystallized from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-1fc8b3471dd7433093729c97be2a73e6
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957070B2

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