Potassium Bicarbonate → Carbonic acid 1-(5-{(4-{amino[benzoylimino]methyl}phenylamino)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxy)ethyl ester cyclohexyl ester

HRID 2089629

Reaktionsgleichung

Reaktionsgleichung von HRID 2089629
[NH2:1][C:2](=[N:36][C:37](=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]([C:23]2[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[C:25]([O:31][CH2:32][CH2:33][OH:34])[C:24]=2[F:35])[C:11]2[NH:15][C:14](=[O:16])[N:13]([C:17]3[N:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[N:12]=2)=[CH:5][CH:4]=1.C(=O)([O-])O.[K+].[C:50](=[O:62])([O:55][CH:56]1[CH2:61][CH2:60][CH2:59][CH2:58][CH2:57]1)[O:51][CH:52](Cl)[CH3:53]>CN(C=O)C>[CH:56]1([O:55][C:50](=[O:62])[O:51][CH:52]([O:16][C:14]2[N:13]([C:17]3[N:18]=[CH:19][CH:20]=[CH:21][N:22]=3)[N:12]=[C:11]([CH:10]([NH:9][C:6]3[CH:7]=[CH:8][C:3]([C:2]([NH2:1])=[N:36][C:37](=[O:44])[C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)=[CH:4][CH:5]=3)[C:23]3[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[C:25]([O:31][CH2:32][CH2:33][OH:34])[C:24]=3[F:35])[N:15]=2)[CH3:53])[CH2:61][CH2:60][CH2:59][CH2:58][CH2:57]1

Komponenten

5

Edukt 3

HCID 516893Potassium BicarbonateHCID 112295291-Chloroethyl Cyclohexyl CarbonateHCID 136334022N-[1-amino-1-(4-{[[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]-(5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]triazol-3-yl)methyl]amino}phenyl)methylidene]benzamide

Produkt 1

HCID 67471168Carbonic acid 1-(5-{(4-{amino[benzoylimino]methyl}phenylamino)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxy)ethyl ester cyclohexyl esterAusbeute 52,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

To a mixture of N-[1-amino-1-(4-{[[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]-(5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]triazol-3-yl)methyl]amino}phenyl)methylidene]benzamide (Example 1a, 1.0 g) and DMF (20 mL), potassium hydrogen carbonate (1.67 g) and 1-chloroethyl cyclohexyl carbonate (2.76 g) were added, and the resulting mixture was stirred at 55° C. for 26 hours. The reaction solution was filtered, 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 (680 mg).

Aufarbeitung

  1. additionwere added
  2. filtrationThe reaction solution was filtered
  3. customthe filtrate obtained
  4. concentrationwas concentrated under reduced pressure
  5. customThe residue obtained
  6. customwas purified by NAM silica gel column chromatography (mixed solvent of methanol-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-2b6ad9cf33da400599b25bbc2a97d622
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08436009B2

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