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Sodium hydride → HCID 11421062, Verbindung

HRID 1036751
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1036751
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][OH:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl[C:20]1[N:25]=[CH:24][N:23]=[C:22]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][CH:28]=2)[C:21]=1[N+:37]([O-:39])=[O:38]>CC(N(C)C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][O:16][C:20]2[C:21]([N+:37]([O-:39])=[O:38])=[C:22]([NH:26][C:27]3[CH:28]=[CH:29][C:30]([S:33]([CH3:36])(=[O:34])=[O:35])=[CH:31][CH:32]=3)[N:23]=[CH:24][N:25]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidineHCID 218978866-Chloro-N-(4-(methylsulfonyl)phenyl)-5-nitropyrimidin-4-amine

Produkt 1

HCID 11421062HCID 11421062, VerbindungAusbeute 82,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374Dimethylacetamide
Lösungsmittel

Versuchsvorschrift

4-(2-Hydroxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester (1.0 mmol, 230 μL) and sodium hydride (1.0 mmol, 26 mg) were dissolved in dimethyl acetamide (1.0 mL) and stirred for 30 minutes at room temperature. Then, (6-chloro-5-nitro-pyrimidin-4-yl)-(4-methanesulfonyl-phenyl)-amine (0.21 mmol, 70 mg) was added. The reaction was stirred at 70° C. for 20 minutes. Its progress was monitored by thin layer chromatography and LCMS. Sodium hydride was quenched with water and the desired compound was extracted in ethyl acetate. Organic solvents were evaporated in vacuo. Flash chromatography (Silica gel 60; 40/60 EtoAc/Hexanes) provided Compound A14 as a yellow oil (90 mg, 82%). 1H NMR (400 MHz, CDCl3) δ (ppm): 10.26 (s, 1H), 8.40 (s, 1H), 7.98 (d, 2H), 7.86 (d, 2H), 4.51 (t, 2H), 4.09 (m, 2H), 3.73 (t, 2H), 3.07 (s, 3H), 2.72 (m, 2H), 1.76 (m, 1H), 1.55 (q, 2H), 1.46 (s, 9H), 1.15 (m, 2H). LCMS (ESI), m/z 422.2 (M+H+, 100%).

Aufarbeitung

  1. stirringThe reaction was stirred at 70° C. for 20 minutes
  2. customSodium hydride was quenched with water
  3. extractionthe desired compound was extracted in ethyl acetate
  4. customOrganic solvents were evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-33c4ffa51b33414481cad7b261d17bab
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08546429B2

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