Sodium Iodide → 2,2-dimethylmalonic acid 5-{(4-{amino[benzoylimino]methyl}phenylamino)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxymethyl ester 2,2-dimethylpropyl ester

HRID 2089665

Reaktionsgleichung

Reaktionsgleichung von HRID 2089665
[NH2:1][C:2](=[N:38][C:39](=[O:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]([C:24]2[N:28]=[C:27]([O:29][CH2:30]Cl)[N:26]([C:32]3[N:37]=[CH:36][CH:35]=[CH:34][N:33]=3)[N:25]=2)[C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[C:13]([O:19][CH2:20][CH2:21][OH:22])[C:12]=2[F:23])=[CH:5][CH:4]=1.[CH3:47][C:48]([CH3:60])([CH3:59])[CH2:49][O:50][C:51](=[O:58])[C:52]([CH3:57])([CH3:56])[C:53]([OH:55])=[O:54].[I-].[Na+].C(=O)([O-])O.[K+]>C(OCC)(=O)C.CC(N(C)C)=O>[CH3:47][C:48]([CH3:60])([CH3:59])[CH2:49][O:50][C:51](=[O:58])[C:52]([CH3:57])([CH3:56])[C:53]([O:55][CH2:30][O:29][C:27]1[N:26]([C:32]2[N:33]=[CH:34][CH:35]=[CH:36][N:37]=2)[N:25]=[C:24]([CH:10]([NH:9][C:6]2[CH:7]=[CH:8][C:3]([C:2]([NH2:1])=[N:38][C:39](=[O:46])[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[CH:4][CH:5]=2)[C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[C:13]([O:19][CH2:20][CH2:21][OH:22])[C:12]=2[F:23])[N:28]=1)=[O:54]

Komponenten

7

Edukt 4

HCID 5238Sodium IodideHCID 516893Potassium BicarbonateHCID 183316662,2-Dimethylmalonic acid mono-(2,2-dimethylpropyl)esterHCID 67470606N-[1-amino-1-[4-({(5-chloromethoxy-1-pyrimidin-2-yl-1H-[1,2,4]triazol-3-yl)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}amino)phenyl]methylidene]benzamide

Produkt 1

HCID 682128732,2-dimethylmalonic acid 5-{(4-{amino[benzoylimino]methyl}phenylamino)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxymethyl ester 2,2-dimethylpropyl esterAusbeute 79,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of N-[1-amino-1-[4-({(5-chloromethoxy-1-pyrimidin-2-yl-1H-[1,2,4]triazol-3-yl)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}amino)phenyl]methylidene]benzamide (500 mg), 2,2-dimethylmalonic acid mono-(2,2-dimethylpropyl)ester (1.56 g), sodium iodide (1.16 g), potassium hydrogen carbonate (543 mg), and DMA (50 mL) was stirred at 50° C. for 7 hours. After cooling the mixture to room temperature, ethyl acetate was added thereto, and the resulting mixture was sequentially washed twice with water and with saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the filtrate obtained was concentrated under reduced pressure. The residue obtained was purified by NAM silica gel column chromatography (mixed solvent of methanol-ethyl acetate) to obtain the captioned compound (500 mg).

Aufarbeitung

  1. temperatureAfter cooling the mixture to room temperature
  2. washthe resulting mixture was sequentially washed twice with water and with saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe desiccant was filtered off
  5. customthe filtrate obtained
  6. concentrationwas concentrated under reduced pressure
  7. customThe residue obtained
  8. customwas purified by NAM silica gel column chromatography (mixed solvent of methanol-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-7d63cafaf1214cec9ef0542b37132436
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08436009B2

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