Trifluoroacetic acid → 3-chloro-5-[(6-chloro-2-fluoro-3-{[6-(methyloxy)-1-oxo-1,3,4,9-tetrahydro-2H-beta-carbolin-2-yl]methyl}phenyl)oxy]benzonitrile

HRID 1874793Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1874793
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:21][CH2:20][C:19]3[C:18]4[C:13](=[CH:14][CH:15]=[C:16]([O:22][CH3:23])[CH:17]=4)[N:12](C(OC(C)(C)C)=O)[C:11]=3[C:10]2=[O:31])=[C:4]([F:32])[C:3]=1[O:33][C:34]1[CH:39]=[C:38]([C:40]#[N:41])[CH:37]=[C:36]([Cl:42])[CH:35]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:42][C:36]1[CH:37]=[C:38]([CH:39]=[C:34]([O:33][C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[C:5]([CH2:8][N:9]3[CH2:21][CH2:20][C:19]4[C:18]5[C:13](=[CH:14][CH:15]=[C:16]([O:22][CH3:23])[CH:17]=5)[NH:12][C:11]=4[C:10]3=[O:31])[C:4]=2[F:32])[CH:35]=1)[C:40]#[N:41]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 594515721,1-Dimethylethyl 2-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-6-(methyloxy)-1-oxo-1,2,3,4-tetrahydro-9H-beta-carboline-9-carboxylate

Produkt 1

HCID 594513583-chloro-5-[(6-chloro-2-fluoro-3-{[6-(methyloxy)-1-oxo-1,3,4,9-tetrahydro-2H-beta-carbolin-2-yl]methyl}phenyl)oxy]benzonitrileAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1,1-Dimethylethyl 2-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-6-(methyloxy)-1-oxo-1,2,3,4-tetrahydro-9H-β-carboline-9-carboxylate (0.03 g, 0.05 mmol), was dissolved in CH2Cl2 (1.0 mL) and TFA (1.0 mL) was added dropwise. The reaction mixture was stirred 1 h and the solvent was evaporated. Purification was accomplished by Reverse-Phase HPLC (water/acetonitrile with 0.1% TFA). The desired fractions were neutralized with saturated NaHCO3 and extracted with EtOAc. The organic extracts were combined, dried over Na2SO4, filtered and evaporated to afford the title compound (0.02 g, 80%) as a tan solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 11.50 (br. s., 1H), 7.80 (s, 1H), 7.47-7.55 (m, 3H), 7.39 (t, 1H), 7.27 (d, 1H), 7.04 (d, 1H), 6.86 (dd, 1H), 4.76 (s, 2H), 3.75 (s, 3H), 3.66 (t, 2H), 2.97 (t, 2H). MS: m/z 510.2 (M+1).

Aufarbeitung

  1. customthe solvent was evaporated
  2. customPurification
  3. extractionextracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-3c91a4a12c9a45128a1b6638d0880f7a
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304419B2

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