5-(4-tert-butoxycarbonylamino-pyridin-3-yl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester → 3-(1,2,3,4-Tetrahydro-isoquinolin-5-yl)-pyridin-4-ylamine

HRID 8736Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 8736
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[C:18]2[CH:19]=[N:20][CH:21]=[CH:22][C:23]=2[NH:24]C(OC(C)(C)C)=O)[CH2:9]1)=O)(C)(C)C>FC(F)(F)C(O)=O.ClCCl>[CH2:9]1[C:10]2[C:15](=[C:14]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][C:23]=3[NH2:24])[CH:13]=[CH:12][CH:11]=2)[CH2:16][CH2:17][NH:8]1

Komponenten

4

Edukt 1

HCID 695955295-(4-tert-butoxycarbonylamino-pyridin-3-yl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Produkt 1

HCID 219836983-(1,2,3,4-Tetrahydro-isoquinolin-5-yl)-pyridin-4-ylamineAusbeute 79,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

5-(4-tert-Butoxycarbonylamino-pyridin-3-yl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (0.18 g, 0.42 mmol) was dissolved at room temperature in 20 mL of 10% trifluoroacetic acid in dichloromethane and stirred to room temperature for 18 h. The volatiles were evaporated, the residue was suspended in toluene and evaporated again. The residue was purified by flash chromatography eluting with 7% methanol in dichloromethane containing 0.7% of ammonium hydroxide to yield 0.075 g of 3-(1,2,3,4-tetrahydro-isoquinolin-5-yl)-pyridin-4-ylamine.

Aufarbeitung

  1. customThe volatiles were evaporated
  2. customevaporated again
  3. customThe residue was purified by flash chromatography
  4. washeluting with 7% methanol in dichloromethane containing 0.7% of ammonium hydroxide

Quellen und Nachweise

ORD-Eintrag
ord-22d804a479bd47db9e903fb2062703f6
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091200B2

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