4-(2-Fluoro-4-nitrophenoxy)-6-(methylsulfinyl)thieno[3,2-d]pyrimidine → N-(3-Fluoro-4-(6-(methylsulfinyl)thieno[3,2-]pyrimidin-4-yloxy)phenyl carbamothioyl)-2-phenylacetamide

HRID 1261350Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1261350
FC1C=C([N+]([O-])=O)C=CC=1OC1[C:6]2[S:13][C:12]([S:14]([CH3:16])=[O:15])=[CH:11][C:7]=2N=CN=1.[F:24][C:25]1[CH:26]=[C:27]([NH:43][C:44]([NH:46][C:47](=[O:55])[CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)=[S:45])[CH:28]=[CH:29][C:30]=1[O:31][C:32]1C2SC(SC)=CC=2[N:35]=[CH:36][N:37]=1>>[F:24][C:25]1[CH:26]=[C:27]([NH:43][C:44]([NH:46][C:47](=[O:55])[CH2:48][C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)=[S:45])[CH:28]=[CH:29][C:30]=1[O:31][C:32]1[C:7]2[CH:11]=[C:12]([S:14]([CH3:16])=[O:15])[S:13][C:6]=2[N:35]=[CH:36][N:37]=1

Komponenten

3

Edukt 2

HCID 594245544-(2-Fluoro-4-nitrophenoxy)-6-(methylsulfinyl)thieno[3,2-d]pyrimidineHCID 59424579N-(3-Fluoro-4-(6-(methylthio)thieno[3,2-d]pyrimidin-4-yloxy)phenylcarbamothioyl)-2-phenylacetamide

Produkt 1

HCID 86644589N-(3-Fluoro-4-(6-(methylsulfinyl)thieno[3,2-]pyrimidin-4-yloxy)phenyl carbamothioyl)-2-phenylacetamideAusbeute 36 %

Versuchsvorschrift

Starting from the compound 285 and following the procedure described above for the synthesis of compound 283 (scheme 64, step 4, example 225), title compound 286 was obtained in 36% yield as an off-white solid. 1H NMR (DMSO-d6) δ (ppm): 12.45(s, 1H), 11.83(s, 1H), 8.80(s, 1H), 8.13(s, 1H), 7.93(dd, 1H, J1=2.3 Hz, J2=10.9 Hz), 7.55 (t, 1H, J=8.6 Hz), 7.48 (m, 1H), 7.34-7.31(m, 4H), 7.28-7.25(m, 1H), 3.81(s, 2H), 3.08(s, 3H). MS (m/z): 501.0(M+H) (found).

Quellen und Nachweise

ORD-Eintrag
ord-83e91753653841f2a4d3ec17950d44d4
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08470850B2

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