Triphenylphosphine → 5-(4-Methoxy-phenyl)-7-methyl-2-(3-piperidin-1-yl-propoxy)-5,6,7,8-tetrahydro-[1,7]naphthyridine

HRID 2220492

Reaktionsgleichung

Reaktionsgleichung von HRID 2220492
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:18][N:17]([CH3:19])[CH2:16][C:15]3[N:14]=[C:13]([OH:20])[CH:12]=[CH:11][C:10]2=3)=[CH:5][CH:4]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OC([N+](C(OC(C)(C)C)=O)=[N-])=O)(C)(C)C.[N:56]1([CH2:62][CH2:63][CH2:64]O)[CH2:61][CH2:60][CH2:59][CH2:58][CH2:57]1>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:18][N:17]([CH3:19])[CH2:16][C:15]3[N:14]=[C:13]([O:20][CH2:64][CH2:63][CH2:62][N:56]4[CH2:61][CH2:60][CH2:59][CH2:58][CH2:57]4)[CH:12]=[CH:11][C:10]2=3)=[CH:7][CH:8]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 66032Piperidine-1-propanolHCID 19106893Di-t-butyl diazodicarboxylateHCID 178488753HCID 178488753, Verbindung

Produkt 1

HCID 159821725-(4-Methoxy-phenyl)-7-methyl-2-(3-piperidin-1-yl-propoxy)-5,6,7,8-tetrahydro-[1,7]naphthyridineAusbeute 20,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

To a mixture of 5-(4-methoxy-phenyl)-7-methyl-5,6,7,8-tetrahydro-[1,7]naphthyridin-2-ol (0.10 g, 0.37 mmol) and PPh3 (0.097 g, 0.37 mmol) in THF (5 mL) was added a solution of di-tert-butyldiazodicarboxylate (0.085 g, 0.37 mmol) in THF (5 mL). After 30 min, a solution of 3-piperidin-1-yl-propan-1-ol (0.053 g, 0.37 mmol) in THF (5 mL) was added slowly. After 18 h, the mixture was concentrated, and the resulting solid was purified (SiO2; 0-8% 2 M NH3 in MeOH/DCM) to give the title compound (30 mg, 20%). MS (ESI): mass calcd. for C24H33N3O2, 395.26; m/z found, 396.6 [M+H]+. 1H NMR (CDCl3): 7.10-7.04 (m, 3H), 6.83 (d, J=8.6, 2H), 6.45 (d, J=8.4, 1H), 4.33-4.25 (m, 2H), 4.15-4.10 (m, 1H), 3.79 (s, 3H), 3.76-3.70 (m, 1H), 3.57-3.50 (m, 1H), 3.02-2.97 (m, 1H), 2.53-2.45 (m, 3H), 2.44 (s, 3H), 2.42-2.38 (m, 3H), 2.00-1.92 (m, 2H), 1.66-1.54 (m, 7H).

Aufarbeitung

  1. waitAfter 18 h
  2. concentrationthe mixture was concentrated
  3. customthe resulting solid was purified (SiO2; 0-8% 2 M NH3 in MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-611f227c2bf54854bd1e3b0aa33f9d5c
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07417054B2

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