StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Trifluoroacetic acid → 1-(3-(Dimethylphosphoryl)phenyl)-3-(3-fluoro-4-(2-(5-((2-methoxyethylamino)methyl)pyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)urea

HRID 1026800
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1026800
[CH3:1][P:2]([C:5]1[CH:6]=[C:7]([NH:11][C:12](=[O:50])[NH:13][C:14]2[CH:48]=[CH:47][C:17]([O:18][C:19]3[CH:24]=[CH:23][N:22]=[C:21]4[CH:25]=[C:26]([C:28]5[N:33]=[CH:32][C:31]([CH2:34][N:35]([CH2:43][CH2:44][O:45][CH3:46])C(=O)OC(C)(C)C)=[CH:30][CH:29]=5)[S:27][C:20]=34)=[C:16]([F:49])[CH:15]=2)[CH:8]=[CH:9][CH:10]=1)([CH3:4])=[O:3].FC(F)(F)C(O)=O>ClCCl>[CH3:4][P:2]([C:5]1[CH:6]=[C:7]([NH:11][C:12]([NH:13][C:14]2[CH:48]=[CH:47][C:17]([O:18][C:19]3[CH:24]=[CH:23][N:22]=[C:21]4[CH:25]=[C:26]([C:28]5[CH:29]=[CH:30][C:31]([CH2:34][NH:35][CH2:43][CH2:44][O:45][CH3:46])=[CH:32][N:33]=5)[S:27][C:20]=34)=[C:16]([F:49])[CH:15]=2)=[O:50])[CH:8]=[CH:9][CH:10]=1)([CH3:1])=[O:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 67049417Tert-butyl(6-(7-(4-(3-(3-(dimethylphosphoryl)phenyl)ureido)-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)pyridin-3-yl)methyl(2-methoxyethyl)carbamate

Produkt 1

HCID 670482601-(3-(Dimethylphosphoryl)phenyl)-3-(3-fluoro-4-(2-(5-((2-methoxyethylamino)methyl)pyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)ureaAusbeute 38,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

To a solution of compound 288 (230 mg, 0.32 mmol) in dichloromethane (7 mL) under nitrogen at room temperature was added trifluoroacetic acid (2.5 mL, 32 mmol). The reaction mixture was stirred for 16 h at room temperature. The solvent was removed under reduced pressure and a saturated aqueous solution of sodium bicarbonate was added. The aqueous phase was extracted with ethyl acetate (3×), the combined organic layers were concentrated. The residue was purified via Biotage (linear gradient 0-20%, methanol/dichloromethane; 25M column) to afford compound 289 as an off-white solid (75.3 mg, 0.122 mmol, 38.0%). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.15 (s, 1H), 9.06 (s, 1H), 8.57 (d, J=1.6 Hz, 1H), 8.53 (d, J=5.6 Hz, 1H), 8.31 (s, 1H), 8.23 (d, J=8.0 Hz, 1H), 7.92-7.83 (m, 2H), 7.76 (dd, J=13.2, 2.4 Hz, 1H), 7.67-7.62 (m, 1H), 7.49-7.42 (m, 2H), 7.41-7.33 (m, 1H), 7.32-7.26 (m, 1H), 6.67 (d, J=5.6 Hz, 1H), 3.78 (s, 2H), 3.54-3.34 (2H, hidden under water signal), 3.24 (s, 3H), 2.65 (t, J=5.6 Hz, 2H), 1.65 (d, J=13.2 Hz, 6H). MS (m/z): 620.4 (M+H).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. additiona saturated aqueous solution of sodium bicarbonate was added
  3. extractionThe aqueous phase was extracted with ethyl acetate (3×)
  4. concentrationthe combined organic layers were concentrated
  5. customThe residue was purified via Biotage (linear gradient 0-20%, methanol/dichloromethane; 25M column)

Quellen und Nachweise

ORD-Eintrag
ord-48e5cf7236bb4a839f2489e92f6a7eb3
Quelldatensatz
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08729268B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion