Potassium trimethylsilanolate → N-(7-(2-Fluoro-4-iodophenylamino)-8-fluoro-4-methylquinazolin-6-yl)-1-(2-(tert-butyldimethylsilyloxy)ethyl)cyclopropane-1-sulfonamide

HRID 558253Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 558253
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:21]2[C:12](=[CH:13][C:14]3[C:15]([CH3:23])=[N:16][CH:17]=[N:18][C:19]=3[C:20]=2[F:22])[N:11]([S:24]([C:27]2([CH2:30][CH2:31][O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])[CH2:29][CH2:28]2)(=[O:26])=[O:25])C1=O.C[Si](C)(C)[O-].[K+]>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:21]1[C:20]([F:22])=[C:19]2[C:14]([C:15]([CH3:23])=[N:16][CH:17]=[N:18]2)=[CH:13][C:12]=1[NH:11][S:24]([C:27]1([CH2:30][CH2:31][O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:34])[CH3:35])[CH2:28][CH2:29]1)(=[O:25])=[O:26]

Komponenten

4

Edukt 2

HCID 23668039Potassium trimethylsilanolateHCID 595194813-(2-Fluoro-4-iodophenyl)-1-(1-(2-(tert-butyldimethylsilyloxy)ethyl)cyclopropylsulfonyl)-4-fluoro-8-methyl-1H-imidazo[4,5-g]quinazolin-2(3H)-one

Produkt 1

HCID 59519447N-(7-(2-Fluoro-4-iodophenylamino)-8-fluoro-4-methylquinazolin-6-yl)-1-(2-(tert-butyldimethylsilyloxy)ethyl)cyclopropane-1-sulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3-(2-fluoro-4-iodophenyl)-1-(1-(2-(tert-butyldimethylsilyloxy)ethyl)cyclopropylsulfonyl)-4-fluoro-8-methyl-1H-imidazo[4,5-g]quinazolin-2(3H)-one (66 mg, 0.1 mmol) in THF (5 ml) is added potassium trimethylsilanolate (65 mg, 0.5 mmol). The resulting solution is stirred at room temperature for 24 h. The reaction is quenched with saturated aqueous NH4Cl solution (10 ml) and extracted with EtOAc (2×10 ml). The combined organic solution is washed with brine (10 ml), dried over MgSO4 and concentrated. Silica gel chromatography yields the desired product.

Aufarbeitung

  1. customThe reaction is quenched with saturated aqueous NH4Cl solution (10 ml)
  2. extractionextracted with EtOAc (2×10 ml)
  3. washThe combined organic solution is washed with brine (10 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e2a035c06dc14ee8a4d4e2b0f39a7a07
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063049B2

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