Dimethylformamide → HCID 68212999, Verbindung

HRID 2089631

Reaktionsgleichung

Reaktionsgleichung von HRID 2089631
[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.CN(C=O)C.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:57][O:58][C:59](=[O:66])[C:60]([CH3:65])([CH3:64])[CH2:61][O:62][CH3:63]>O.C(OCC)(=O)C>[NH2:1][C:2](=[N:36][C:37](=[O:44])[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=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[N:15]=[C:14]([O:16][CH2:57][O:58][C:59](=[O:66])[C:60]([CH3:65])([CH3:64])[CH2:61][O:62][CH3:63])[N:13]([C:17]3[N:18]=[CH:19][CH:20]=[CH:21][N:22]=3)[N:12]=2)=[CH:5][CH:4]=1

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 144596933-Methoxy-2,2-dimethylpropionic acid chloromethyl esterHCID 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 68212999HCID 68212999, VerbindungAusbeute 35,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °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, 45 mg) and DMF (2 mL), cesium carbonate (29 mg) and 3-methoxy-2,2-dimethylpropionic acid chloromethyl ester (20 mg) were sequentially added, and the resulting mixture was stirred at 60° C. for 4 hours. The resulting mixture was poured into ethyl acetate (30 mL) and water (20 mL). After shaking the mixture, the organic layer was collected. The organic layer was sequentially washed twice with water (30 mL) and with saturated aqueous sodium chloride solution (20 mL), and dried over anhydrous magnesium sulfate. The resulting mixture 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 (20 mg).

Aufarbeitung

  1. additionwere sequentially added
  2. stirringAfter shaking the mixture
  3. customthe organic layer was collected
  4. washThe organic layer was sequentially washed twice with water (30 mL) and with saturated aqueous sodium chloride solution (20 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe resulting mixture was filtered
  7. customthe filtrate obtained
  8. concentrationwas concentrated under reduced pressure
  9. customThe residue obtained
  10. customwas purified by NAM silica gel column chromatography (mixed solvent of methanol-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-527ceb6ba360489dacf24700108e7804
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08436009B2

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