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(2-Methoxyethyl)(methyl)amine → (E)-N-(2-Methoxyethyl)-N-methyl-4-[2-(1H-indazol-3-yl)vinyl]benzamide

HRID 2378716
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2378716
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=2)=[N:2]1.[CH3:21][O:22][CH2:23][CH2:24][NH:25][CH3:26].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(=O)([O-])O.[Na+]>C1COCC1>[CH3:21][O:22][CH2:23][CH2:24][N:25]([CH3:26])[C:16](=[O:18])[C:15]1[CH:14]=[CH:13][C:12](/[CH:11]=[CH:10]/[C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][N:2]=2)=[CH:20][CH:19]=1
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Komponenten

7

Edukt 5

HCID 300977(2-Methoxyethyl)(methyl)amineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 11437002(E)-4-(2-(1H-indazol-3-yl)vinyl)benzoic acid

Produkt 1

HCID 67089879
(E)-N-(2-Methoxyethyl)-N-methyl-4-[2-(1H-indazol-3-yl)vinyl]benzamide
Ausbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(E)-4-[2-(1H-indazol-3-yl)vinyl]benzoic acid (0.18 g, 0.67 mmol) obtained in Step 6 of Example 1 was dissolved in THF (4 mL), and the solution was added with N-(2-methoxyethyl)methylamine (0.11 mL, 1.00 mmol), 1-hydroxybenzotriazole monohydrate (0.12 g, 0.85 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.18 g, 0.92 mmol), followed by stirring at room temperature for 2 hours. The reaction mixture was added with a saturated aqueous sodium hydrogencarbonate solution, was extracted with ethyl acetate, the organic layer was sequentially washed with water and saturated brine, was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=25/1) to obtain Compound 5 (0.22 g, 99%).

Aufarbeitung

  1. extractionwas extracted with ethyl acetate
  2. washthe organic layer was sequentially washed with water and saturated brine
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform/methanol=25/1)

Quellen und Nachweise

ORD-Eintrag
ord-036f3c2d665e40989bfe4d9c1e719264
Quelldatensatz
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07470717B2

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