Water → 6-bromo-1-cyclopentyl-N-((4-(hydroxymethyl)-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1H-indazole-4-carboxamide

HRID 1854159Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1854159
[Br:1][C:2]1[CH:3]=[C:4]([C:16]([OH:18])=O)[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.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[NH2:52][CH2:53][C:54]1[C:55](=[O:70])[NH:56][C:57]([CH3:69])=[CH:58][C:59]=1[CH2:60][O:61][Si](C(C)(C)C)(C)C.O>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:16]([NH:52][CH2:53][C:54]2[C:55](=[O:70])[NH:56][C:57]([CH3:69])=[CH:58][C:59]=2[CH2:60][OH:61])=[O:18])[C:5]2[CH:6]=[N:7][N:8]([CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15]3)[C:9]=2[CH:10]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 2724699PyBOPHCID 674684486-bromo-1-cyclopentyl-1H-indazole-4-carboxylic acidHCID 682947603-(aminomethyl)-4-(((tert-butyldimethylsilyl)oxy)methyl)-6-methylpyridin-2(1H)-one

Produkt 1

HCID 682948306-bromo-1-cyclopentyl-N-((4-(hydroxymethyl)-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1H-indazole-4-carboxamideAusbeute 40,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a solution of 6-bromo-1-cyclopentyl-1H-indazole-4-carboxylic acid (2.3 g, 7.5 mmol) in DMSO (30 mL), PyBOP (5.82 g, 11.20 mmol) was added and reaction stirred at room temperature for 15 min. 3-(Aminomethyl)-4-(((tert-butyldimethylsilyl)oxy)methyl)-6-methylpyridin-2(1H)-one (2.52 g, 8.96 mmol) was then added and reaction mixture stirred overnight. On completion, water was added and the resulting precipitate filtered and washed with water. This solid was then stirred with acetonitrile for 10 min and filtered again to obtain 6-bromo-1-cyclopentyl-N-((4-(hydroxymethyl)-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1H-indazole-4-carboxamide (1.4 g, 40.9%).

Aufarbeitung

  1. customreaction
  2. customreaction mixture
  3. stirringstirred overnight
  4. filtrationthe resulting precipitate filtered
  5. washwashed with water
  6. stirringThis solid was then stirred with acetonitrile for 10 min
  7. filtrationfiltered again

Quellen und Nachweise

ORD-Eintrag
ord-4f345ed09aba4a6ab4107a3c588990a1
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962620B2

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