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Hydrazine → 2-Amino-7-aminomethyl-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester

HRID 1166800
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1166800
[C:1]([O:5][C:6]([C:8]1[C:16]2[CH2:15][CH2:14][N:13]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[CH:12]([CH2:26][N:27]3C(=O)C4C(=CC=CC=4)C3=O)[C:11]=2[S:10][C:9]=1[NH2:38])=[O:7])([CH3:4])([CH3:3])[CH3:2].NN>C(O)C>[C:1]([O:5][C:6]([C:8]1[C:16]2[CH2:15][CH2:14][N:13]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=3)[CH:12]([CH2:26][NH2:27])[C:11]=2[S:10][C:9]=1[NH2:38])=[O:7])([CH3:4])([CH3:2])[CH3:3]
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Komponenten

4

Edukt 2

HCID 9321HydrazineHCID 695604722-Amino-7-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester

Produkt 1

HCID 219366842-Amino-7-aminomethyl-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl esterAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702Ethanol
Lösungsmittel

Versuchsvorschrift

In a 500 ml round-bottom flask, a suspension of 2-amino-7-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester (5.00 g, 9.4 mmol) in absolute ethanol (200 ml) was flushed with nitrogen. The reaction mixture was stirred at room temperature and hydrazine (1.5 ml, 47.8 mmol) was added. The reaction mixture was heated to 80° C. for 6 hours and then cooled to room temperature. After 14 hours at room temperature, the precipitate was filtered off and washed with absolute ethanol. The mother liquid was concentrated in vacuo and the residue was dissolved in dichloromethane (75 ml) and refiltered to remove an additional precipitate. Concentration of the mother liquid afforded 3.2 g (85%) of 2-amino-7-aminomethyl-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester as a solid.

Aufarbeitung

  1. customwas flushed with nitrogen
  2. temperatureThe reaction mixture was heated to 80° C. for 6 hours
  3. temperaturecooled to room temperature
  4. filtrationthe precipitate was filtered off
  5. washwashed with absolute ethanol
  6. concentrationThe mother liquid was concentrated in vacuo
  7. dissolutionthe residue was dissolved in dichloromethane (75 ml)
  8. customto remove an additional precipitate

Quellen und Nachweise

ORD-Eintrag
ord-fa4710e814884b5fa3b8b3852cd6b1c8
Quelldatensatz
uspto-grants-2003_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06613903B2

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