Ethanol → 4-{2-[3-amino-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl]-4-chlorophenoxy}-5-chloro-2-fluoro-N-(methoxymethyl)-N-pyrimidin-4-ylbenzenesulfonamide

HRID 1402070Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1402070
[Cl:1][C:2]1[C:3]([O:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=2[C:30]2[C:31]([N+:41]([O-])=O)=[N:32][N:33]([CH:35]3[CH2:40][CH2:39][CH2:38][CH2:37][O:36]3)[CH:34]=2)=[CH:4][C:5]([F:21])=[C:6]([S:8]([N:11]([CH2:18][O:19][CH3:20])[C:12]2[CH:17]=[CH:16][N:15]=[CH:14][N:13]=2)(=[O:10])=[O:9])[CH:7]=1.C(O)C.[Cl-].[NH4+]>[Fe]>[NH2:41][C:31]1[C:30]([C:24]2[CH:25]=[C:26]([Cl:29])[CH:27]=[CH:28][C:23]=2[O:22][C:3]2[C:2]([Cl:1])=[CH:7][C:6]([S:8]([N:11]([CH2:18][O:19][CH3:20])[C:12]3[CH:17]=[CH:16][N:15]=[CH:14][N:13]=3)(=[O:10])=[O:9])=[C:5]([F:21])[CH:4]=2)=[CH:34][N:33]([CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][O:36]2)[N:32]=1

Komponenten

5

Edukt 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 594365105-chloro-4-(4-chloro-2-(3-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)phenoxy)-2-fluoro-N-(methoxymethyl)-N-(pyrimidin-4-yl)benzenesulfonamide

Produkt 1

HCID 594365744-{2-[3-amino-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl]-4-chlorophenoxy}-5-chloro-2-fluoro-N-(methoxymethyl)-N-pyrimidin-4-ylbenzenesulfonamideAusbeute 97,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23925IronKatalysator

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 5-chloro-4-(4-chloro-2-(3-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)phenoxy)-2-fluoro-N-(methoxymethyl)-N-(pyrimidin-4-yl)benzenesulfonamide (80 mg, 0.1 mmol) in ethanol (4 mL, 70 mmol) was added saturated aqueous ammonium chloride solution (0.4 mL, 6 mmol) and iron (328 mg, 5.87 mmol). The reaction solution was heated at 80° C. for 20 minutes then filtered. Saturated aqueous sodium bicarbonate was added until the pH was 9. The mixture was concentrated in vacuo to remove the ethanol. Water was added and the mixture was extracted three times with dichloromethane. The combined organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified on silica gel (hexane to 100% ethyl acetate gradient) to give 61 mg of a colorless oil.

Aufarbeitung

  1. filtrationthen filtered
  2. additionSaturated aqueous sodium bicarbonate was added until the pH was 9
  3. concentrationThe mixture was concentrated in vacuo
  4. customto remove the ethanol
  5. additionWater was added
  6. extractionthe mixture was extracted three times with dichloromethane
  7. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified on silica gel (hexane to 100% ethyl acetate gradient)

Quellen und Nachweise

ORD-Eintrag
ord-9106f9b4145f4ebe9a40c31f40c46b8f
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08907101B2

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