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Triethylamine → 5-[2-(4,4-Dimethyl-2-oxo-1,3-oxazolidin-3-yl)-1,3-thiazol-4-yl]-1-methyl-1H-pyrrole-3-carbonitrile

HRID 1436470
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1436470
[OH:1][CH2:2][C:3]([NH:6][C:7]1[S:8][CH:9]=[C:10]([C:12]2[N:16]([CH3:17])[CH:15]=[C:14]([C:18]#[N:19])[CH:13]=2)[N:11]=1)([CH3:5])[CH3:4].C(N(CC)CC)C.Cl[C:28](Cl)([O:30]C(=O)OC(Cl)(Cl)Cl)Cl>O1CCCC1>[CH3:4][C:3]1([CH3:5])[CH2:2][O:1][C:28](=[O:30])[N:6]1[C:7]1[S:8][CH:9]=[C:10]([C:12]2[N:16]([CH3:17])[CH:15]=[C:14]([C:18]#[N:19])[CH:13]=2)[N:11]=1
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Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 866186245-{2-[(2-hydroxy-1,1-dimethylethyl)amino]-1,3-thiazol-4-yl}-1-methyl-1H-pyrrole-3-carbonitrile

Produkt 1

HCID 689018825-[2-(4,4-Dimethyl-2-oxo-1,3-oxazolidin-3-yl)-1,3-thiazol-4-yl]-1-methyl-1H-pyrrole-3-carbonitrileAusbeute 66,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

To a solution of 5-{2-[(2-hydroxy-1,1-dimethylethyl)amino]-1,3-thiazol-4-yl}-1-methyl-1H-pyrrole-3-carbonitrile (1.10 g, 3.98 mmol), prepared in the previous step, in dry tetrahydrofuran (10 mL) under nitrogen was added triethylamine (0.56 mL, 4 mmol), followed by triphosgene (1.18 g, 4 mmol). After 2 h, the mixture was partitioned between water and ethyl acetate. The organic layers were washed with water, dried (anhydrous sodium sulfate) and evaporated. The residue was then purified by silica gel column chromatography (ethyl acetate:hexanes, gradient elution) to afford the title compound (0.80 g, 66%) as an off white powder. HRMS: calcd for C14H14N4O2S [M+H]+, 303.09102; found (ESI, [M+H]+), 303.093, ANLC 99.4% at 210-370 nm, 8.6 min; 99.7% at 246 nm, 8.6 min, the Xterra® RP18 column, 3.5%, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min.

Aufarbeitung

  1. customthe mixture was partitioned between water and ethyl acetate
  2. washThe organic layers were washed with water
  3. dry with materialdried (anhydrous sodium sulfate)
  4. customevaporated
  5. customThe residue was then purified by silica gel column chromatography (ethyl acetate:hexanes, gradient elution)

Quellen und Nachweise

ORD-Eintrag
ord-40ee992707fb48c09fc33ce3338a5295
Quelldatensatz
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07618990B2

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