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Hydrochloric Acid → HCID 66893833, Verbindung

HRID 2250049
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2250049
C1COCC1.[CH2:6]([O:8][C:9](=[O:37])/[CH:10]=[CH:11]/[C:12]1[C:13]([NH:28][C:29]2[C:34]([F:35])=[CH:33][CH:32]=[CH:31][C:30]=2[F:36])=[N:14][C:15]([S:26][CH3:27])=[N:16][C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[CH3:25])C.Cl.CCOC(C)=O>CO.O>[CH3:6][O:8][C:9](=[O:37])[CH2:10][CH2:11][C:12]1[C:13]([NH:28][C:29]2[C:34]([F:35])=[CH:33][CH:32]=[CH:31][C:30]=2[F:36])=[N:14][C:15]([S:26][CH3:27])=[N:16][C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[CH3:25]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 10276274(E)-3-[4-(2,6-difluoro-phenylamino)-6-(4-fluoro-2-methyl-phenyl)-2-methylsulfanyl-pyrimidin-5-yl]-acrylic acid ethyl ester

Produkt 1

HCID 66893833HCID 66893833, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887
Methanol
Lösungsmittel
HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of SmI2 in THF (0.1M) (Aldrich) (15 mL, 1.5 mmol) and MeOH (3 mL) was added the product of Example 30 (100 mg, 0.22 mmol) and the reaction mixture maintained its blue color. The presence of new product and the disappearance of starting material was indicated by hplc. After 30 min, the reaction was diluted with H2O (10 mL), then 1 M HCl (3 mL), followed by EtOAc (20 mL), the layers were shaken together and separated. The aq phase was washed with EtOAc (20 mL) and the combined EtOAc was dried (MgSO4) and the solvent was evaporated in vacuo and the residue was crystalized from i-PrOH/H2O (1:1) to afford 3-[4-(2,6-difluoro-phenylamino)-6-(4-fluoro-2-methyl-phenyl)-2-methylsulfanyl-pyrimidin-5-yl]-propionic acid methyl ester. LC MS (m/e)=448.2 (MH+), Rt=2.17 min.

Aufarbeitung

  1. temperaturethe reaction mixture maintained its blue color
  2. customseparated
  3. washThe aq phase was washed with EtOAc (20 mL)
  4. dry with materialthe combined EtOAc was dried (MgSO4)
  5. customthe solvent was evaporated in vacuo
  6. customthe residue was crystalized from i-PrOH/H2O (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-5f821169c3ba47ae83582eadc917810d
Quelldatensatz
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07314934B2

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