Methanol → 3-[4-(2-Hydroxyethoxy)-3-methoxyphenyl]-8-[2-(4-morpholin-4-ylphenoxy)ethyl]-5,10-dihydro-11h-dibenzo[b,e][1,4]diazepin-11-one

HRID 272730

Reaktionsgleichung

Reaktionsgleichung von HRID 272730
[Si]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]=[CH:20][C:21]3[C:27](=[O:28])[NH:26][C:25]4[CH:29]=[C:30]([CH2:33][CH2:34][O:35][C:36]5[CH:41]=[CH:40][C:39]([N:42]6[CH2:47][CH2:46][O:45][CH2:44][CH2:43]6)=[CH:38][CH:37]=5)[CH:31]=[CH:32][C:24]=4[NH:23][C:22]=3[CH:48]=2)=[CH:14][C:13]=1[O:49][CH3:50])(C(C)(C)C)(C)C.CO.O.[F-].C([N+](CC)(CC)CC)C>O1CCOCC1>[OH:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]=[CH:20][C:21]3[C:27](=[O:28])[NH:26][C:25]4[CH:29]=[C:30]([CH2:33][CH2:34][O:35][C:36]5[CH:41]=[CH:40][C:39]([N:42]6[CH2:43][CH2:44][O:45][CH2:46][CH2:47]6)=[CH:38][CH:37]=5)[CH:31]=[CH:32][C:24]=4[NH:23][C:22]=3[CH:48]=2)=[CH:14][C:13]=1[O:49][CH3:50]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 16211652Tetraethylammonium fluoride hydrateHCID 692197303-[4-(2-{[Tert-butyl(dimethyl)silyl]oxy}ethoxy)-3-methoxyphenyl]-8-[2-(4-morpholin-4-ylphenoxy)ethyl]-5,10-dihydro-11h-dibenzo[b,e][1,4]diazepin-11-one

Produkt 1

HCID 692179193-[4-(2-Hydroxyethoxy)-3-methoxyphenyl]-8-[2-(4-morpholin-4-ylphenoxy)ethyl]-5,10-dihydro-11h-dibenzo[b,e][1,4]diazepin-11-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of Example 609A (23 mg, 0.033 mmol) in 1:1 MeOH:dioxane (2 mL) was treated with tetraethylammonium fluoride hydrate (49.4 mg, 0.33 mmol) at 50° C. for 24 hours. The reaction was then cooled to room temperature, concentrated, diluted with ethyl acetate, washed with water and brine, dried (MgSO4), filtered and concentrated. The residue was purified by preparative HPLC to provide the title compound. MS (ESI) m/e 582 (M+H)+; 1H NMR (300 MHz, DMSO-d6) □ 9.75 (s, 1H), 7.84 (s, 1H), 7.72 (d, J=8.1 Hz, 1H), 7.25 (d, J=1.4 Hz, 1H), 7.15-7.20 (m, 3H), 7.07 (m, 1H), 6.80-6.96 (m, 7H), 4.00-4.06 (m, 4H), 3.85 (s, 3H), 3.70-3.75 (m, 6H), 2.96-2.99 (m, 4H), 2.86 (t, J=6.4 Hz, 2H).

Aufarbeitung

  1. concentrationconcentrated
  2. additiondiluted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-c2466413a495452f9dde97f90696a8ba
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456169B2

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