Trifluoroacetic acid → N-[2-(3-Cyano-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazol-8-yloxy)-ethyl]-methanesulfonamide

HRID 61721Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 61721
FC(F)(F)C(O)=O.[NH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]2[C:27](=[O:28])[C:26]3[C:25]4[C:20](=[CH:21][C:22]([C:29]#[N:30])=[CH:23][CH:24]=4)[NH:19][C:18]=3[C:17]([CH3:32])([CH3:31])[C:16]=2[CH:33]=1.C(N(C(C)C)CC)(C)C.[CH3:43][S:44](Cl)(=[O:46])=[O:45]>ClCCl.O>[C:29]([C:22]1[CH:21]=[C:20]2[C:25]([C:26]3[C:27](=[O:28])[C:15]4[CH:14]=[CH:13][C:12]([O:11][CH2:10][CH2:9][NH:8][S:44]([CH3:43])(=[O:46])=[O:45])=[CH:33][C:16]=4[C:17]([CH3:31])([CH3:32])[C:18]=3[NH:19]2)=[CH:24][CH:23]=1)#[N:30]

Komponenten

7

Edukt 4

HCID 6422Trifluoroacetic acidHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 668337928-(2-amino-ethoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

Produkt 1

HCID 66833850N-[2-(3-Cyano-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazol-8-yloxy)-ethyl]-methanesulfonamideAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trifluoroacetic acid salt of 8-(2-amino-ethoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound A8-2, 19 mg, 0.044 mmol) was suspended in dichloromethane (0.5 mL), added with diisopropylethylamine (0.0157 mL, 2 eq.) and methanesulfonyl chloride (0.0034 mL, 1 eq.), and then stirred at room temperature for 2 hr. The reaction solution was added to water, and then extracted with dichloromethane. After washing with saturated brine, the organic layer was dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were separated by silica gel preparative TLC (ethyl acetate 100%) to obtain the target compound (5.5 mg, 29%).

Aufarbeitung

  1. extractionextracted with dichloromethane
  2. washAfter washing with saturated brine
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. customThe drying agent was removed by filtration
  5. customthe residues obtained
  6. concentrationafter concentration under reduced pressure
  7. customwere separated by silica gel preparative TLC (ethyl acetate 100%)

Quellen und Nachweise

ORD-Eintrag
ord-506c277519da482291685818c6d45abd
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440922B2

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