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

HRID 1476389Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1476389
Br[C:2]1[CH:3]=[C:4]([C:14]([NH:16][CH2:17][C:18]2[C:19](=[O:26])[NH:20][C:21]([CH3:25])=[CH:22][C:23]=2[CH3:24])=[O:15])[C:5]2[CH:6]=[N:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=2[CH:10]=1.CC1(C)C(C)(C)OB([C:35]2[CH:36]=[CH:37][C:38]([N:41]3[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]3)=[N:39][CH:40]=2)O1>>[CH3:24][C:23]1[CH:22]=[C:21]([CH3:25])[NH:20][C:19](=[O:26])[C:18]=1[CH2:17][NH:16][C:14]([C:4]1[C:5]2[CH:6]=[N:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=2[CH:10]=[C:2]([C:35]2[CH:40]=[N:39][C:38]([N:41]3[CH2:42][CH2:43][NH:44][CH2:45][CH2:46]3)=[CH:37][CH:36]=2)[CH:3]=1)=[O:15]

Komponenten

3

Edukt 2

HCID 162179462-(Piperazin-1-yl)pyridine-5-boronic acid, pinacol esterHCID 545964906-bromo-N-((1,2-dihydro-4,6-dimethyl-2-oxopyridin-3-yl)methyl)-1-isopropyl-1H-indazole-4-carboxamide

Produkt 1

HCID 54596558N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-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-(1-methylethyl)-N-[(6-methyl-2-oxo-4-methyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide (90 mg, 0.216 mmol) and 1-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl]piperazine (94 mg, 0.324 mmol). The product obtained from HPLC purification was treated with a saturated solution of NaHCO3, and solids that crashed out were filtered. The product was evaporated from MeOH, triturated from ether and then CH3CN. After drying in vacuum oven overnight, the final product was collected as a white solid (87 mg, 78%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.53 (br. s., 1H) 8.59-8.67 (m, 2H) 8.54 (s, 1H) 8.35 (s, 1H) 8.02-8.09 (m, 2H) 7.84 (s, 1H) 6.94 (d, J=9.09 Hz, 1H) 5.89 (s, 1H) 5.14 (dt, J=13.07, 6.47 Hz, 1H) 4.39 (br. s., 1H) 4.38 (br. s., 1H) 3.41-3.47 (m, 4H) 3.17 (s, 1H) 2.22 (s, 3H) 2.13 (s, 3H) 1.50 (s, 3H) 1.49 (s, 3H). LC-MS (ES) m/z=500.4 [M+H]+ Note: some piperinzyl proton atoms hidden under water peak.

Aufarbeitung

  1. customThe product obtained from HPLC purification
  2. additionwas treated with a saturated solution of NaHCO3, and solids that
  3. filtrationcrashed out were filtered
  4. customThe product was evaporated from MeOH
  5. customtriturated from ether
  6. customAfter drying in vacuum oven overnight
  7. customthe final product was collected as a white solid (87 mg, 78%)

Quellen und Nachweise

ORD-Eintrag
ord-9334c696d6f44002ad95add01249c9d0
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09018382B2

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