2-Fluoroethyl methanesulfonate → 1-Cyclopropyl-3-(3-fluoro-4-(2-(5-((4-((2-fluoroethyl)(methyl)amino)piperidin-1-yl)methyl)pyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)urea

HRID 1400935Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1400935
CS(O[CH2:6][CH2:7][F:8])(=O)=O.[CH:9]1([NH:12][C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]3[CH:28]=[CH:27][N:26]=[C:25]4[CH:29]=[C:30]([C:32]5[CH:37]=[CH:36][C:35]([CH2:38][N:39]6[CH2:44][CH2:43]N(CCF)C[CH2:40]6)=[CH:34][N:33]=5)[S:31][C:24]=34)=[C:18]([F:48])[CH:17]=2)=[O:14])[CH2:11][CH2:10]1>>[CH:9]1([NH:12][C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]3[CH:28]=[CH:27][N:26]=[C:25]4[CH:29]=[C:30]([C:32]5[CH:37]=[CH:36][C:35]([CH2:38][N:39]6[CH2:44][CH2:43][CH:9]([N:12]([CH2:6][CH2:7][F:8])[CH3:13])[CH2:10][CH2:40]6)=[CH:34][N:33]=5)[S:31][C:24]=34)=[C:18]([F:48])[CH:17]=2)=[O:14])[CH2:11][CH2:10]1

Komponenten

3

Edukt 2

HCID 680342-Fluoroethyl methanesulfonateHCID 866586031-Cyclopropyl-3-(3-fluoro-4-(2-(5-((4-(2-fluoroethyl)piperazin-1-yl)methyl)pyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)urea

Produkt 1

HCID 866586021-Cyclopropyl-3-(3-fluoro-4-(2-(5-((4-((2-fluoroethyl)(methyl)amino)piperidin-1-yl)methyl)pyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)urea

Versuchsvorschrift

Compound 421 (example 269) was prepared in one step by reacting the amine precursor 401 (table 31) with compound 419, similarly to compound 420 (example 268, scheme 77). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.73 (s, 1H), 8.54 (d, J=1.6 Hz, 1H), 8.52 (d, J=5.6 Hz, 1H), 8.33 (s, 1H), 8.24 (d, J=8.0 Hz, 1H), 7.85 (dd, J=8.0, 2.0 Hz, 1H), 7.73 (dd, J=13.6, 2.4 Hz, 1H), 7.38 (t, J=9.0 Hz, 1H), 7.22-7.18 (m, 1H), 6.64 (d, J=5.2 Hz, 1H), 6.56 (bd, J=2.8 Hz, 1H), 4.51 (t, J=5.2 Hz, 1H), 4.39 (t, J=5.2 Hz, 1H), 3.54 (s, 2H), 2.90-2.82 (m, 2H), 2.77-2.63 (m, 2H), 2.59-2.50 (m, 1H), 2.40-2.30 (m, 1H), 2.22 (s, 3H), 2.02-1.91 (m, 2H), 1.69-1.61 (m, 2H), 1.50-1.38 (m, 2H), 0.68-0.62 (m, 2H), 0.45-0.40 (m, 2H). MS (m/z): 593.59 (M+H).

Quellen und Nachweise

ORD-Eintrag
ord-57262cd041694e76bc1c694bf19d08f9
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906852B2

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