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Methanol → N-[2-[5-(2-hydroxyethyl)-4,5-dihydro-1,3-thiazol-2-yl]-5-(trifluoromethoxy)-1H-indol-7-yl]-N-methylthiophene-2-sulfonamide

HRID 1960525
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HRID 1960525 반응식
C([O:3][C:4](=O)[CH2:5][CH:6]1[S:10][C:9]([C:11]2[NH:12][C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([O:20][C:21]([F:24])([F:23])[F:22])=[CH:15][C:14]=3[N:25]([CH3:34])[S:26]([C:29]2[S:30][CH:31]=[CH:32][CH:33]=2)(=[O:28])=[O:27])=[N:8][CH2:7]1)C.O1CCCC1.CO.[BH4-].[Li+]>O>[OH:3][CH2:4][CH2:5][CH:6]1[S:10][C:9]([C:11]2[NH:12][C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([O:20][C:21]([F:23])([F:22])[F:24])=[CH:15][C:14]=3[N:25]([CH3:34])[S:26]([C:29]2[S:30][CH:31]=[CH:32][CH:33]=2)(=[O:28])=[O:27])=[N:8][CH2:7]1
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참가 물질

6

반응물 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4148881Lithium borohydride2회HCID 57476345ethyl {2-[7-[methyl(2-thienylsulfonyl)amino]-5-(trifluoromethoxy)-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetate

생성물 1

HCID 59135731N-[2-[5-(2-hydroxyethyl)-4,5-dihydro-1,3-thiazol-2-yl]-5-(trifluoromethoxy)-1H-indol-7-yl]-N-methylthiophene-2-sulfonamide
수율 34%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a mixture of ethyl{2-[7-[methyl(2-thienylsulfonyl)amino]-5-(trifluoromethoxy)-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetate (350 mg), tetrahydrofuran (15 mL) and methanol (3 mL) was added lithium borohydride (30 mg), and the mixture was stirred at room temperature for 2 hr. Lithium borohydride (15 mg) was added to the mixture, and the mixture was further stirred at room temperature for 2 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography, and eluted with hexane-ethyl acetate (2:1-1:4, volume ratio) to give the title compound (110 mg, yield 34%) as colorless crystals. The crystals were recrystallized from ethyl acetate-hexane to give colorless prism crystals. melting point 152-153° C.

후처리

  1. stirringthe mixture was further stirred at room temperature for 2 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. washeluted with hexane-ethyl acetate (2:1-1:4, volume ratio)

출처 및 근거

ORD 기록
ord-a93fa30ef00342a4b671652f1c8456ae
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08410087B2

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