(2-Methoxy-phenyl)-acetyl isothiocyanate → N-(3-Fluoro-4-(2-(3-hydroxyazetidine-1-carbonyl)thieno[3,2-b]pyridin-7-yloxy)phenylcarbamothioyl)-2-(2-methoxyphenyl)acetamide

HRID 1261360Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1261360
[NH2:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[CH:13]=[C:14]([C:16]([N:18]4[CH2:21][CH:20]([OH:22])[CH2:19]4)=[O:17])[S:15][C:8]=23)=[C:4]([F:25])[CH:3]=1.CSC1SC2C(=NC=CC=2OC2C=CC(NC(NC(=O)CC3C=CC=CC=3)=S)=CC=2F)C=1.[CH3:58][O:59][C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][C:61]=1[CH2:66][C:67]([N:69]=[C:70]=[S:71])=[O:68]>>[F:25][C:4]1[CH:3]=[C:2]([NH:1][C:70]([NH:69][C:67](=[O:68])[CH2:66][C:61]2[CH:62]=[CH:63][CH:64]=[CH:65][C:60]=2[O:59][CH3:58])=[S:71])[CH:24]=[CH:23][C:5]=1[O:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]2[CH:13]=[C:14]([C:16]([N:18]3[CH2:19][CH:20]([OH:22])[CH2:21]3)=[O:17])[S:15][C:8]=12

Komponenten

4

Edukt 3

HCID 21890860(2-Methoxy-phenyl)-acetyl isothiocyanateHCID 249017001-(4-(2-(Methylthio)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-3-(2-phenylacetyl)thioureaHCID 59424504(7-(4-Amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)(3-hydroxyazetidin-1-yl)methanone

Produkt 1

HCID 59424675N-(3-Fluoro-4-(2-(3-hydroxyazetidine-1-carbonyl)thieno[3,2-b]pyridin-7-yloxy)phenylcarbamothioyl)-2-(2-methoxyphenyl)acetamideAusbeute 39 %

Versuchsvorschrift

Starting from the amine 299, following the procedure described above for the synthesis of compound 232a (scheme 50, example 203) but replacing 2-phenylacetyl isothiocyanate with (2-methoxy-phenyl)-acetyl isothiocyanate and title compound 300 was obtained in 39% yield as a creamy solid. 1HNMR: (CD3OD) δ (ppm): 12.58 (s, 1H), 11.77 (s, 1H), 8.62 (m, 1H), 8.09 (d, J=12.3 Hz, 1H), 7.95 (s, 1H), 7.56 (m, 2H), 7.26 (m, 2H), 7.00 (m, 1H), 6.92 (m, 1H), 6.77 (m, 1H), 6.50 (d, J=5.9 Hz, 1H), 4.81 (m, 1H), 4.59 (m, 1H), 4.35 (m, 2H), 3.87-3.78 (m, 6H). MS (m/z): 567.0 (M+1).

Quellen und Nachweise

ORD-Eintrag
ord-30f54335d2bf405384e036067829a5a9
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08470850B2

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