N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamide → 5-[1-(1,3-Dimethyl-1H-pyrazol-4-yl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-8-yl]-pyridine-2-carboxylic acid methylamide

HRID 445559Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 445559
Br[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([CH3:23])[C:13](=[O:22])[N:14]([C:15]4[C:16]([CH3:21])=[N:17][N:18]([CH3:20])[CH:19]=4)[C:5]=3[C:4]=2[CH:3]=1.[CH3:24][NH:25][C:26]([C:28]1[CH:33]=[CH:32][C:31](B2OC(C)(C)C(C)(C)O2)=[CH:30][N:29]=1)=[O:27]>>[CH3:24][NH:25][C:26]([C:28]1[CH:33]=[CH:32][C:31]([C:2]2[CH:11]=[CH:10][C:9]3[N:8]=[CH:7][C:6]4[N:12]([CH3:23])[C:13](=[O:22])[N:14]([C:15]5[C:16]([CH3:21])=[N:17][N:18]([CH3:20])[CH:19]=5)[C:5]=4[C:4]=3[CH:3]=2)=[CH:30][N:29]=1)=[O:27]

Komponenten

3

Edukt 2

HCID 44119560N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamideHCID 596197398-Bromo-1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one2×

Produkt 1

HCID 498353095-[1-(1,3-Dimethyl-1H-pyrazol-4-yl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-8-yl]-pyridine-2-carboxylic acid methylamide

Versuchsvorschrift

The title compound was synthesized in a similar manner as described for Example 1.1 using 8-bromo-1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (Intermediate A, 40 mg, 0.105 mmol) and 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine-2-carboxylic acid methylamide (Stage 15.1.1, 42 mg, 0.160 mmol) to give the title compound as a lightly yellow solid. (HPLC: tR 2.39 min (Method A); M+H=428 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 9.01 (s, 1H), 8.87-8.80 (m, 1H), 8.71-8.67 (m, 1H), 8.18-8.07 (m, 4H), 8.04-7.98 (m, 1H), 7.65 (s, 1H), 3.92 (s, 3H), 3.58 (s, 3H), 2.83 (s, 3H), 1.97 (s, 3H))

Aufarbeitung

  1. customThe title compound was synthesized in a similar manner

Quellen und Nachweise

ORD-Eintrag
ord-0a2d65ff93694977a00acb8f3b11d2b7
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476294B2

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