Water → HCID 178482114, Verbindung

HRID 1262335

Reaktionsgleichung

Reaktionsgleichung von HRID 1262335
CS([C:4]1[N:9]=[CH:8][C:7]2=[C:10]([O:25][CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[CH:11]=[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:19]([CH3:24])[S:20]([CH3:23])(=[O:22])=[O:21])[N:6]2[N:5]=1)=O.[OH-:34].[Na+].O>C(O)(=O)C>[OH:34][C:4]1[N:9]=[CH:8][C:7]2=[C:10]([O:25][CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:32])([CH3:33])[CH3:31])[CH:11]=[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:19]([CH3:24])[S:20]([CH3:23])(=[O:22])=[O:21])[N:6]2[N:5]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 66711169N-{2-[2-Methanesulfinyl-5-(2-trimethylsilanyl-ethoxymethoxy)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-N-methyl-methane sulfonamide

Produkt 1

HCID 178482114HCID 178482114, VerbindungAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Into a 8-dram vial, N-{2-[2-Methanesulfinyl-5-(2-trimethylsilanyl-ethoxymethoxy)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-N-methyl-methane sulfonamide (480 mg, 0.94 mmol) was added to heated solution of 19.10 M of Sodium hydroxide in Water (5.0 mL, 96 mmol) at 110° C. The reaction mixture was heated at 120° C. for 2 hours. 5 mL of Acetic acid was added to adjust pH to 5. The reaction was partitioned with water and DCM. The organic was separated, washed with Brine and dried over Na2SO4. The solid was filtered and washed with DCM. The solvent was removed under vacuum. The reaction mixture was purified via ISCO column chromatography with DCM and NH3 in methanol as eluant (2 to 15% methanol). The collected fractions afforded N-{2-[2-Hydroxy-5-(2-trimethylsilanyl-ethoxymethoxy)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-N-methyl-methanesulfonamide as a red solid (195 mg, 45%).

Aufarbeitung

  1. customThe reaction was partitioned with water and DCM
  2. customThe organic was separated
  3. washwashed with Brine
  4. dry with materialdried over Na2SO4
  5. filtrationThe solid was filtered
  6. washwashed with DCM
  7. customThe solvent was removed under vacuum
  8. customThe reaction mixture was purified via ISCO column chromatography with DCM and NH3 in methanol as eluant (2 to 15% methanol)

Quellen und Nachweise

ORD-Eintrag
ord-1b37cdd9346b471c9a364f439a1827ab
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08471005B2

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