2-(Piperazin-1-yl)pyridine-5-boronic acid, pinacol ester → 1-cyclopentyl-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-6-[6-(1-piperazinyl)-3-pyridinyl]-1H-indazole-4-carboxamide

HRID 85465Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 85465
Br[C:2]1[CH:3]=[C:4]([C:16]([NH:18][CH2:19][C:20]2[C:21](=[O:28])[NH:22][C:23]([CH3:27])=[CH:24][C:25]=2[CH3:26])=[O:17])[C:5]2[CH:6]=[N:7][N:8]([CH:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)[C:9]=2[CH:10]=1.CC1(C)C(C)(C)OB([C:37]2[CH:38]=[CH:39][C:40]([N:43]3[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]3)=[N:41][CH:42]=2)O1>>[CH:11]1([N:8]2[C:9]3[CH:10]=[C:2]([C:37]4[CH:42]=[N:41][C:40]([N:43]5[CH2:44][CH2:45][NH:46][CH2:47][CH2:48]5)=[CH:39][CH:38]=4)[CH:3]=[C:4]([C:16]([NH:18][CH2:19][C:20]4[C:21](=[O:28])[NH:22][C:23]([CH3:27])=[CH:24][C:25]=4[CH3:26])=[O:17])[C:5]=3[CH:6]=[N:7]2)[CH2:15][CH2:14][CH2:13][CH2:12]1

Komponenten

3

Edukt 2

HCID 162179462-(Piperazin-1-yl)pyridine-5-boronic acid, pinacol esterHCID 545970746-bromo-1-cyclopentyl-N-[(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]-1H-indazole-4-carboxamide

Produkt 1

HCID 545972291-cyclopentyl-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-6-[6-(1-piperazinyl)-3-pyridinyl]-1H-indazole-4-carboxamide

Versuchsvorschrift

The title compound was prepared in a similar manner as described for example 8 from 6-bromo-1-cyclopentyl-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide (200 mg, 0.451 mmol) and 1-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl]piperazine (196 mg, 0.677 mmol). The product was collected as a white solid (92 mg, 37%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.54 (br. s., 1H) 8.64-8.67 (m, 1H) 8.60 (t, J=4.80 Hz, 1H) 8.35 (s, 1H) 8.03-8.09 (m, 2H) 7.84 (d, J=1.26 Hz, 1H) 6.89-6.99 (m, 1H) 5.89 (s, 1H) 5.27-5.35 (m, 1H) 4.39 (br. s., 1H) 4.38 (br. s., 1H) 3.41-3.56 (m, 4H) 2.69-2.91 (m, 4H) 2.22 (s, 3H) 2.07-2.20 (m, 6H) 1.97-2.06 (m, 2H) 1.85-1.93 (m, 2H) 1.65-1.74 (m, 2H). LC-MS (ES) m/z=526.3 [M+H]+

Aufarbeitung

  1. customThe product was collected as a white solid (92 mg, 37%)

Quellen und Nachweise

ORD-Eintrag
ord-4ada0d32fa8747338fb6be311a7e1a11
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846935B2

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