1,1'-Carbonyl-di-(1,2,4-triazole) → HCID 131734789, Verbindung

HRID 1777973Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1777973
N1([C:6](N2C=NC=N2)=[O:7])C=NC=N1.[NH2:13][C:14]1[CH:21]=[C:20]([NH:22][CH2:23][CH2:24][O:25][CH3:26])[C:17]([C:18]#[N:19])=[CH:16][N:15]=1.[CH3:27][O:28][CH:29]([O:57][CH3:58])[C:30]1[C:39]([CH2:40][N:41]2[CH2:46][CH2:45][N:44]([C:47]([O:49][CH2:50][CH2:51][Si:52]([CH3:55])([CH3:54])[CH3:53])=[O:48])[CH2:43][C:42]2=[O:56])=[CH:38][C:37]2[CH2:36][CH2:35][CH2:34][NH:33][C:32]=2[N:31]=1>CN(C=O)C>[C:18]([C:17]1[C:20]([NH:22][CH2:23][CH2:24][O:25][CH3:26])=[CH:21][C:14]([NH:13][C:6]([N:33]2[C:32]3[N:31]=[C:30]([CH:29]([O:28][CH3:27])[O:57][CH3:58])[C:39]([CH2:40][N:41]4[CH2:46][CH2:45][N:44]([C:47]([O:49][CH2:50][CH2:51][Si:52]([CH3:53])([CH3:55])[CH3:54])=[O:48])[CH2:43][C:42]4=[O:56])=[CH:38][C:37]=3[CH2:36][CH2:35][CH2:34]2)=[O:7])=[N:15][CH:16]=1)#[N:19]

Komponenten

5

Edukt 3

HCID 43939611,1'-Carbonyl-di-(1,2,4-triazole)HCID 1180369516-Amino-4-((2-methoxyethyl)amino)nicotinonitrile2×HCID 1317347902-(Trimethylsilyl)ethyl 4-((2-(dimethoxymethyl)-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)methyl)-3-oxopiperazine-1-carboxylate2×

Produkt 1

HCID 131734789HCID 131734789, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

A solution of di(1H-1,2,4-triazol-1-yl)methanone (2.78 g, 15.23 mmol) in DMF (15 ml) was added to 6-amino-4-((2-methoxyethyl)amino)nicotinonitrile (intermediate 75, 2.96 g, 15.23 mmol) in anhydrous DMF (15 ml) at 0° C. After stirring for 2.5 h at room temperature a solution of 2-(trimethylsilyl)ethyl 4-((2-(dimethoxymethyl)-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)methyl)-3-oxopiperazine-1-carboxylate (intermediate 123, 2.83 g, 6.09 mmol) in DMF (20 ml) was added. The reaction mixture was stirred for 17.5 h at room temperature, then partitioned between saturated aqueous NaHCO3 solution and EtOAc, the EtOAc phase washed with brine, dried over MgSO4 and evaporated. The residue was applied to a RediSep® silica column and purified by normal phase chromatography, eluting with EtOAc then a gradient from hexane to 50% EtOAc in hexane. Product containing fractions were combined and evaporated to give the title compound as a clear pale yellow oil. (UPLC-MS 7) tR 1.28; ESI-MS 683.5 [M+H]+.

Aufarbeitung

  1. additionwas added
  2. custompartitioned between saturated aqueous NaHCO3 solution and EtOAc
  3. washthe EtOAc phase washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. custompurified by normal phase chromatography
  7. washeluting with EtOAc
  8. additionProduct containing fractions
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-d114627c980d436a8946ffb7dfffee69
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09266883B2

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