Morpholine → 6,6-Dimethyl-8-(1-oxetan-3-yl-piperidin-4-yl)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 2202436Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2202436
[NH:1]1[CH2:6][CH2:5]O[CH2:3][CH2:2]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH:21]([C:23]1[CH:24]=[CH:25][C:26]2[C:38](=[O:39])[C:37]3[C:36]4[C:31](=[CH:32][C:33]([C:40]#[N:41])=[CH:34][CH:35]=4)[NH:30][C:29]=3[C:28]([CH3:43])([CH3:42])[C:27]=2[CH:44]=1)=O.[O:45]1[CH2:48][C:47](=O)[CH2:46]1>C1COCC1>[CH3:42][C:28]1([CH3:43])[C:29]2[NH:30][C:31]3[C:36](=[CH:35][CH:34]=[C:33]([C:40]#[N:41])[CH:32]=3)[C:37]=2[C:38](=[O:39])[C:26]2[CH:25]=[CH:24][C:23]([CH:21]3[CH2:3][CH2:2][N:1]([CH:47]4[CH2:46][O:45][CH2:48]4)[CH2:6][CH2:5]3)=[CH:44][C:27]1=2

Komponenten

6

Edukt 4

HCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 150242543-OxetanoneHCID 866638188-Formyl-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

Produkt 1

HCID 533573286,6-Dimethyl-8-(1-oxetan-3-yl-piperidin-4-yl)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

With the same condition as the method for synthesizing the Compound B3-32 (morpholine (6 μl, 1.5 eq.) and sodium triacetoxy borohydride (81 mg, 2.0 eq.) were added to THF (1 ml) solution of the Compound B2-29: 8-formyl-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (30 mg, 0.095 mmol), and stirred at room temperature for 1 hour. The reaction solution was filtered to remove insoluble matters. The residues obtained after concentration under reduced pressure were purified by high performance liquid chromatography to obtain the Compound B3-32 (6,6-dimethyl-8-morpholin-4-yl methyl-11-oxo-6,11-dihydro-5H-benzo carbazole-3-carbonitrile) (19 mg, 50%)), the title compound was synthesized from the Compound B3-13-2 and oxetan-3-one.

Aufarbeitung

  1. customWith the same condition as the method for synthesizing the Compound
  2. filtrationThe reaction solution was filtered
  3. customto remove insoluble matters
  4. customThe residues obtained
  5. concentrationafter concentration under reduced pressure
  6. customwere purified by high performance liquid chromatography
  7. customto obtain the Compound

Quellen und Nachweise

ORD-Eintrag
ord-1952870e6d774c6aa6359839fe36fe86
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365514B2

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