Sodium hydride → HCID 136492459, Verbindung

HRID 59557Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 59557
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Br[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[NH:20][C:19](=[O:21])[N:18]([C:22]3[CH:23]=[C:24]([CH:33]=[CH:34][C:35]=3[Cl:36])[CH2:25][NH:26][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])[N:17]=2)=[CH:12][CH:11]=1>CN(C=O)C>[Cl:36][C:35]1[CH:34]=[CH:33][C:24]([CH2:25][NH:26][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:23][C:22]=1[N:18]1[C:19](=[O:21])[NH:20][C:16]([C:13]2[CH:12]=[CH:11][C:10]([CH2:9][N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:15][CH:14]=2)=[N:17]1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 31268PyrrolidineHCID 136644856N-(3-(3-(4-(bromomethyl)phenyl)-4,5-dihydro-5-oxo-1,2,4-triazol-1-yl)-4-chlorobenzyl)pivalamide

Produkt 1

HCID 136492459HCID 136492459, VerbindungAusbeute 10,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a cold solution of pyrolidine (0.060 g, 0.830 mmol) in DMF was added NaH (0.034 g, 0.830 mmol) at 0° C. and stirred the reaction mass for 1 h. Then solution of N-(3-(3-(4-(bromomethyl)phenyl)-4,5-dihydro-5-oxo-1,2,4-triazol-1-yl)-4-chlorobenzyl)pivalamide (Intermediate-103, 0.200 g, 0.419) in DMF was added at 0° C. and continued stirring at 5-10° C. for 2-3 h. The reaction mass was quenched in ice and pH adjusted to 6-7 and extracted with DCM. The organic layer was dried over anhydrous sodium sulphate and concentrated. The obtained crude product was purified by column chromatography on basic alumina, eluting with 5% MeOH:DCM to afford 0.020 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 1.23 (s, 9H), 1.79 (br s, 4H), 2.53 (br s, 4H), 3.66 (s, 2H), 4.48 (d, J=5.7 Hz, 2H), 6.08 (m, 1H), 7.26-7.54 (m, 5H), 7.79 (d, J=7.8 Hz, 2H); MS (m/z): 468.51 (M+H)+.

Aufarbeitung

  1. stirringcontinued stirring at 5-10° C. for 2-3 h
  2. customThe reaction mass was quenched in ice
  3. extractionextracted with DCM
  4. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  5. concentrationconcentrated
  6. customThe obtained crude product
  7. customwas purified by column chromatography on basic alumina
  8. washeluting with 5% MeOH

Quellen und Nachweise

ORD-Eintrag
ord-32a47506a118475dac86bc07225a6aa2
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09439890B2

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