Sodium hydride → US9777003, Example 24

HRID 628265Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 628265
[H-].[Na+].[CH3:3][C:4]1[N:8]2[C:9]3[CH:15]=[C:14]([CH3:16])[NH:13][C:10]=3[CH:11]=[CH:12][C:7]2=[N:6][N:5]=1.Br[CH:18]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:19][CH2:20][CH2:21][CH3:22]>CN(C=O)C>[CH3:3][C:4]1[N:8]2[C:9]3[CH:15]=[C:14]([CH3:16])[N:13]([CH:18]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH2:19][CH2:20][CH2:21][CH3:22])[C:10]=3[CH:11]=[CH:12][C:7]2=[N:6][N:5]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 10900349(1-Bromopentyl)benzeneHCID 1369631111,7-dimethyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine

Produkt 1

HCID 118159523US9777003, Example 24

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sodium hydride (0.011 g, 0.27 mmol, 60% in mineral oil) was added to a solution of 1,7-dimethyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine (50.0 mg, 0.268 mmol, from Example 2, Step 5) in DMF (6 mL). After stirring for 10 minutes, (1-bromopentyl)benzene (0.061 g, 0.27 mmol, from Step 1) was added. After stirring for 45 minutes, the reaction was quenched by the addition of water and the mixture was diluted with MeCN, filtered and purified via preparative HPLC-MS (Waters XBridge C18, eluting with a gradient of MeCN/H2O containing 0.15% NH4OH) (0.01 g, 10%).

Aufarbeitung

  1. stirringAfter stirring for 45 minutes
  2. customthe reaction was quenched by the addition of water
  3. additionthe mixture was diluted with MeCN
  4. filtrationfiltered
  5. custompurified via preparative HPLC-MS (Waters XBridge C18
  6. washeluting with a gradient of MeCN/H2O containing 0.15% NH4OH) (0.01 g, 10%)

Quellen und Nachweise

ORD-Eintrag
ord-d5663a6d55b741bd9316bd34c98067b8
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309246B2

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