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Sodium Bicarbonate → N-[2-(5-{[2-(hydroxymethyl)-1H-imidazol-1-yl]methyl}-4,5-dihydro-1,3-thiazol-2-yl)-1H-indol-7-yl]-N-methylpyridine-2-sulfonamide

HRID 504949
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 504949
[CH3:1][N:2]([S:28]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1)(=[O:30])=[O:29])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:13][CH:14]([CH2:17][N:18]3[CH:22]=[CH:21][N:20]=[C:19]3[C:23](OCC)=[O:24])[CH2:15][N:16]=1)=[CH:8]2.[BH4-].[Li+].C(=O)([O-])O.[Na+]>O1CCCC1.CO>[OH:24][CH2:23][C:19]1[N:18]([CH2:17][CH:14]2[S:13][C:12]([C:9]3[NH:10][C:11]4[C:7]([CH:8]=3)=[CH:6][CH:5]=[CH:4][C:3]=4[N:2]([CH3:1])[S:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=3)(=[O:29])=[O:30])=[N:16][CH2:15]2)[CH:22]=[CH:21][N:20]=1
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Komponenten

6

Edukt 3

HCID 516892Sodium BicarbonateHCID 4148881Lithium borohydride2×HCID 59135802ethyl 1-[(2-{7-[methyl(pyridin-2-ylsulfonyl)amino]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)methyl]-1H-imidazole-2-carboxylate

Produkt 1

HCID 59135809N-[2-(5-{[2-(hydroxymethyl)-1H-imidazol-1-yl]methyl}-4,5-dihydro-1,3-thiazol-2-yl)-1H-indol-7-yl]-N-methylpyridine-2-sulfonamideAusbeute 19 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Ethyl 1-[(2-{7-[methyl(pyridin-2-ylsulfonyl)amino]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)methyl]-1H-imidazole-2-carboxylate (220 mg) was dissolved in a mixed solvent of tetrahydrofuran (8 mL) and methanol (4 mL), lithium borohydride (27 mg) was added, and the mixture was stirred at room temperature for 1 hr. Lithium borohydride (20 mg) was added, and the mixture was stirred at room temperature for 24 hr. Saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and filtrated, and the filtrate was concentrated under reduced pressure. The residue was silica gel column chromatography (methanol:ethyl acetate=0:100-15:85) to give the title compound (38 mg, yield 19%) as a white solid. MS: 482 (MH+).

Aufarbeitung

  1. additionwas added
  2. stirringthe mixture was stirred at room temperature for 24 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltrated
  7. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b3d04ab13b474690b08dff3fd253e29e
Quelldatensatz
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07777047B2

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