Benzenesulfonyl chloride → methyl [4-amino-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]carbamate

HRID 1097610Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1097610
[OH:1][C:2]([CH3:24])([CH3:23])[CH2:3][N:4]1[C:16]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N+:9]([O-])=[CH:8][C:7]=2[N:6]=[C:5]1[NH:18][C:19](=[O:22])[O:20][CH3:21].[OH-].[NH4+:26].C1(S(Cl)(=O)=O)C=CC=CC=1>CO>[NH2:26][C:8]1[C:7]2[N:6]=[C:5]([NH:18][C:19](=[O:22])[O:20][CH3:21])[N:4]([CH2:3][C:2]([OH:1])([CH3:24])[CH3:23])[C:16]=2[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:9]=1

Komponenten

5

Edukt 3

HCID 7369Benzenesulfonyl chloride2×HCID 14923Ammonium HydroxideHCID 86626309methyl [1-(2-hydroxy-2-methylpropyl)-5-oxido-1H-imidazo[4,5-c]quinolin-2-yl]carbamate

Produkt 1

HCID 57550537methyl [4-amino-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]carbamateAusbeute 45,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A suspension of methyl [1-(2-hydroxy-2-methylpropyl)-5-oxido-1H-imidazo[4,5-c]quinolin-2-yl]carbamate (0.80 g, 2.4 mmol) in methanol (10 mL) was stirred vigorously and cooled to 0° C. Concentrated ammonium hydroxide (0.8 mL, 25 mmol) was added followed by benzenesulfonyl chloride (0.9 g, 5 mmol), which was added dropwise. The mixture was stirred for two hours at 0° C. to 5° C. An analysis by LC/MS indicated the reaction was incomplete. Additional benzenesulfonyl chloride (0.9 g) was added, and the reaction mixture was stirred overnight at room temperature. The solvent was removed under reduced pressure, and the residue was purified by automated flash chromatography (40+M silica cartridge, eluting with 0% to 25% CMA in chloroform) followed by recrystallization from ethyl acetate to provide 0.36 g of methyl [4-amino-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]carbamate as a white solid, mp 255-258° C. (decomposition).

Aufarbeitung

  1. additionwas added dropwise
  2. stirringThe mixture was stirred for two hours at 0° C. to 5° C
  3. stirringthe reaction mixture was stirred overnight at room temperature
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by automated flash chromatography (40+M silica cartridge, eluting with 0% to 25% CMA in chloroform)
  6. customfollowed by recrystallization from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-e5d65f421c004249bd3844edb1cfded0
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143270B2

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