Diisopropylethylamine → HCID 59483838, Verbindung

HRID 1808377Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1808377
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([C:18](O)=[O:19])=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[B-](F)(F)(F)F.CN(C(ON1N=NC2C1=CC=CC=2)=[N+](C)C)C.O.ON1C2C=CC=CC=2N=N1.Cl.Cl.[N:56]1[CH:61]=[CH:60][C:59]([N:62]2[CH2:67][CH2:66][C:65]3([CH2:72][CH2:71][NH:70][CH2:69][CH2:68]3)[CH2:64][CH2:63]2)=[CH:58][CH:57]=1.C(N(C(C)C)CC)(C)C>O1CCCC1>[N:56]1[CH:57]=[CH:58][C:59]([N:62]2[CH2:67][CH2:66][C:65]3([CH2:72][CH2:71][N:70]([C:18]([C:12]4[CH:11]=[C:10]5[C:15]([CH2:16][CH2:17][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]5)=[CH:14][CH:13]=4)=[O:19])[CH2:69][CH2:68]3)[CH2:64][CH2:63]2)=[CH:60][CH:61]=1

Komponenten

7

Edukt 5

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27960291-Hydroxybenzotriazole hydrateHCID 189883742-((Tert-butoxy)carbonyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxylic acidHCID 66701057HCID 66701057, Verbindung

Produkt 1

HCID 59483838HCID 59483838, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxylic acid (2 g, 0.0072 mol), 0-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (2.3 g, 0.0072 mol) and 1-hydroxybenzotriazole hydrate (0.99 g, 0.0072 mol) were dissolved in tetrahydrofuran, under nitrogen, and the mixture was stirred for 30 min at RT. A solution of 3-(pyridin-4-yl)-3,9-diazaspiro[5.5]undecane dihydrochloride (F-09) (2.18 g, 0.0072 mol) and diisopropylethylamine (DIPEA) (4.28 g, 0.025 mol) in tetrahydrofuran was added, and the reaction mixture was stirred for 15 h at RT. Tetrahydrofuran was then removed in vacuo, the residue was taken up in ethyl acetate and sat. sodium hydrogen carbonate solution, and the phases were separated. The aqueous phase was extracted with ethyl acetate, and the combined organic phases were in turn washed with sat. sodium chloride solution, dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (ethyl acetate/methanol 20:1+1% 25% ammonia solution (aq.)). Yield: 1.91 g (54%).

Aufarbeitung

  1. stirringthe reaction mixture was stirred for 15 h at RT
  2. customTetrahydrofuran was then removed in vacuo
  3. customsat. sodium hydrogen carbonate solution, and the phases were separated
  4. extractionThe aqueous phase was extracted with ethyl acetate
  5. washwashed with sat. sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by column chromatography (ethyl acetate/methanol 20:1+1% 25% ammonia solution (aq.))

Quellen und Nachweise

ORD-Eintrag
ord-069327a4dedc47a9b85abf142903a4c6
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08357717B2

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