Acetic Acid → 5-(cyclopentylamino)-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-4'-((dimethylamino)methyl)-4-methyl-[1,1'-biphenyl]-3-carboxamide

HRID 1530200Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1530200
[CH:1]1([NH:6][C:7]2[C:8]([CH3:34])=[C:9]([C:21]([NH:23][CH2:24][C:25]3[C:26](=[O:33])[NH:27][C:28]([CH3:32])=[CH:29][C:30]=3[CH3:31])=[O:22])[CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([CH:19]=O)=[CH:15][CH:14]=3)[CH:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:35][NH:36][CH3:37].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH:1]1([NH:6][C:7]2[C:8]([CH3:34])=[C:9]([C:21]([NH:23][CH2:24][C:25]3[C:26](=[O:33])[NH:27][C:28]([CH3:32])=[CH:29][C:30]=3[CH3:31])=[O:22])[CH:10]=[C:11]([C:13]3[CH:14]=[CH:15][C:16]([CH2:19][N:36]([CH3:37])[CH3:35])=[CH:17][CH:18]=3)[CH:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 674DimethylamineHCID 5003444Sodium cyanoborohydrideHCID 866726395-(cyclopentylamino)-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-4'-formyl-4-methyl-[1,1'-biphenyl]-3-carboxamide

Produkt 1

HCID 708723055-(cyclopentylamino)-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-4'-((dimethylamino)methyl)-4-methyl-[1,1'-biphenyl]-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 5-(cyclopentylamino)-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-4′-formyl-4-methyl-[1,1′-biphenyl]-3-carboxamide (0.11 g, 0.24 mmol) and N,N-dimethylamine (0.044 g, 1.2 mmol) in methanol (3 mL) was added acetic acid (0.014 g, 0.24 mmol) and the solution stirred at room temperature for 3 h. Then sodium cyanoborohydride (0.030 g, 0.48 mmol) was added and the solution stirred overnight. The solvent was removed under reduced pressure and the residue purified by column chromatography over silica gel to afford desired 5-(cyclopentylamino)-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-4′-((dimethylamino)methyl)-4-methyl-[1,1′-biphenyl]-3-carboxamide

Aufarbeitung

  1. stirringthe solution stirred overnight
  2. customThe solvent was removed under reduced pressure
  3. customthe residue purified by column chromatography over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-a64b9388dd304a13a5191c0ffe8392ec
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090562B2

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