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

HRID 61720

Reaktionsgleichung

Reaktionsgleichung von HRID 61720
Cl.[CH3:2][C:3]1([CH3:31])[C:15]2[NH:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([C:16]#[N:17])[CH:12]=3)[C:7]=2[C:6](=[O:18])[C:5]2[CH:19]=[CH:20][C:21]([O:23][CH2:24][CH:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)=[CH:22][C:4]1=2.[O:32]1[CH2:35][C:34](=O)[CH2:33]1.C1COCC1.C([BH3-])#N.[Na+]>C(O)(=O)C.O.CO>[CH3:2][C:3]1([CH3:31])[C:15]2[NH:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([C:16]#[N:17])[CH:12]=3)[C:7]=2[C:6](=[O:18])[C:5]2[CH:19]=[CH:20][C:21]([O:23][CH2:24][CH:25]3[CH2:30][CH2:29][N:28]([CH:34]4[CH2:35][O:32][CH2:33]4)[CH2:27][CH2:26]3)=[CH:22][C:4]1=2

Komponenten

8

Edukt 4

HCID 8028TetrahydrofuranHCID 5003444Sodium cyanoborohydrideHCID 150242543-OxetanoneHCID 668343006,6-Dimethyl-11-oxo-8-(piperidin-4-ylmethoxy)-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile hydrochloric acid salt

Produkt 1

HCID 668344386,6-Dimethyl-8-(1-oxetan-3-yl-piperidin-4-ylmethoxy)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrileAusbeute 43,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

6,6-Dimethyl-11-oxo-8-(piperidin-4-ylmethoxy)-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile hydrochloric acid salt (Compound A7-25, 30 mg, 0.075 mmol) and oxetan-3-one (38 mg, 7 eq.) were dissolved in acetic acid (0.2 ml), THF (1 ml) and methanol (1 ml), added with sodium cyanoborohydride (33 mg, 7 eq.) at room temperature, and stirred overnight. The reaction solution was added with water, and then extracted with ethyl acetate. The solution was dried over sodium sulfate and the solvent was removed under vacuum and the resulting residues were purified by preparative TLC (chloroform: 2 N ammonia methanol=9:1) to obtain the target compound (15 mg).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe solution was dried over sodium sulfate
  3. customthe solvent was removed under vacuum
  4. customthe resulting residues were purified by preparative TLC (chloroform: 2 N ammonia methanol=9:1)

Quellen und Nachweise

ORD-Eintrag
ord-b18223b5a281405fb046a292826eac0a
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440922B2

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