8-Amino-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one → 8-{5-Chloro-4-[2-fluoro-6-(tetrahydro-furan-3-ylmethoxy)-phenylamino]-pyrimidin-2-ylamino}-1,3,4,5-tetrahydro-1-benzazepin-2-one

HRID 1041308

Reaktionsgleichung

Reaktionsgleichung von HRID 1041308
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH2:10][CH2:9][C:8](=[O:12])[NH:7][C:6]=2[CH:13]=1.Cl[C:15]1[N:20]=[C:19]([NH:21][C:22]2[C:27]([O:28][CH2:29][CH:30]3[CH2:34][CH2:33][O:32][CH2:31]3)=[CH:26][CH:25]=[CH:24][C:23]=2[F:35])[C:18]([Cl:36])=[CH:17][N:16]=1>>[Cl:36][C:18]1[C:19]([NH:21][C:22]2[C:27]([O:28][CH2:29][CH:30]3[CH2:34][CH2:33][O:32][CH2:31]3)=[CH:26][CH:25]=[CH:24][C:23]=2[F:35])=[N:20][C:15]([NH:1][C:2]2[CH:3]=[CH:4][C:5]3[CH2:11][CH2:10][CH2:9][C:8](=[O:12])[NH:7][C:6]=3[CH:13]=2)=[N:16][CH:17]=1

Komponenten

3

Edukt 2

HCID 46151688-Amino-1,3,4,5-tetrahydro-2H-1-benzazepin-2-oneHCID 86633997(2,5-Dichloro-pyrimidin-4-yl)-[2-fluoro-6-(tetrahydro-furan-3-ylmethoxy)-phenyl]-amine

Produkt 1

HCID 668304588-{5-Chloro-4-[2-fluoro-6-(tetrahydro-furan-3-ylmethoxy)-phenylamino]-pyrimidin-2-ylamino}-1,3,4,5-tetrahydro-1-benzazepin-2-one

Versuchsvorschrift

Title compound was prepared from 8-Amino-1,3,4,5-tetrahydro-benzo[b]azepin-2-one and (2,5-Dichloro-pyrimidin-4-yl)-[2-fluoro-6-(tetrahydro-furan-3-ylmethoxy)-phenyl]-amine in an analogous manner to Example 1221d. Title compound was isolated as a white solid. (65 mg, 49%) HPLC purity=94%, LCMS=498.20 (M+H), 1H-NMR (DMSO-d6, 400 MHz) δ 9.47 (s, 1H), 9.14 (s, 1H), 8.77 (s, 1H), 8.14 (s, 1H), 7.34-7.31 (m, 1H), 7.11 (d, J=8.4 Hz, 1H), 6.97 (d, J=8.5 Hz, 1H), 6.94-6.90 (m, 2H), 6.84 (d, J=8.3 Hz, 1H), 3.94-3.85 (m, 2H), 3.55-3.51 (m, 3H), 3.32-3.28 (m, 1H), 2.55-2.51 (m, 2H), 2.07-2.01 (m, 4H), 2.94-2.84 (m, 1H), 1.49-1.43 (m, 1H), 1.05-1.03 (m, 1H).

Quellen und Nachweise

ORD-Eintrag
ord-b750646ca88e4f3cb28555bc5cd6331c
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552186B2

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