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Citric Acid → N-{2-[5-(2-hydroxyethyl)-4,5-dihydro-1,3-thiazol-2-yl]-4-methyl-1H-indol-7-yl}-N-methylthiophene-2-sulfonamide

HRID 1994908
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1994908
[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]1[S:22][CH:23]([CH2:26][C:27](OCC)=[O:28])[CH2:24][N:25]=1)[NH:6]2.[BH4-].[Li+].O1CCCC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[OH:28][CH2:27][CH2:26][CH:23]1[S:22][C:21]([C:5]2[NH:6][C:7]3[C:3]([CH:4]=2)=[C:2]([CH3:1])[CH:10]=[CH:9][C:8]=3[N:11]([CH3:20])[S:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)(=[O:14])=[O:13])=[N:25][CH2:24]1
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Komponenten

6

Edukt 4

HCID 311Citric AcidHCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 59136158ethyl(2-{4-methyl-7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetate

Produkt 1

HCID 59136065N-{2-[5-(2-hydroxyethyl)-4,5-dihydro-1,3-thiazol-2-yl]-4-methyl-1H-indol-7-yl}-N-methylthiophene-2-sulfonamide
Ausbeute 94,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a mixture of ethyl (2-{4-methyl-7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetate (0.12 g), lithium borohydride (20 mg) and tetrahydrofuran (10 mL) was added methanol (2 mL), and the mixture was stirred at room temperature for 3 hr. Aqueous citric acid solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained crystals were washed with ethyl acetate-hexane to give the title compound (103 mg, yield: 94%) as pale-yellow crystals. MS: 436 (MH+). melting point 168-169° C.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washThe obtained crystals were washed with ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-f59964d265764797b43f81053a8b53f0
Quelldatensatz
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07652133B2

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