Potassium trimethylsilanolate → N-(7-(2-Fluoro-4-iodophenylamino)-8-fluoro-4-methylquinazolin-6-yl)cyclopropanesulfonamide

HRID 558251Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 558251
[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]([CH:27]2[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]([CH:27]1[CH2:28][CH2:29]1)(=[O:25])=[O:26]

Komponenten

4

Edukt 2

HCID 23668039Potassium trimethylsilanolateHCID 595194453-(2-Fluoro-4-iodophenyl)-1-(cyclopropylsulfonyl)-4-fluoro-8-methyl-1H-imidazo[4,5-g]quinazolin-2(3H)-one

Produkt 1

HCID 25161111N-(7-(2-Fluoro-4-iodophenylamino)-8-fluoro-4-methylquinazolin-6-yl)cyclopropanesulfonamideAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3-(2-fluoro-4-iodophenyl)-1-(cyclopropylsulfonyl)-4-fluoro-8-methyl-1H-imidazo[4,5-g]quinazolin-2(3H)-one (46 mg, 0.09 mmol) in THF (5 ml) was added potassium trimethylsilanolate (35 mg, 0.27 mmol). The reaction was stirred at room temperature for 16 h, quenched with saturated aqueous NH4Cl solution (5 ml), and extracted with EtOAc (2×10 ml). The combined organic solution was washed with brine (15 ml), dried over MgSO4, and concentrated. Silica gel chromatography (EtOAc:Hexanes=50:50) yielded 39 mg (90%) of the title compound as a light yellow solid. m/z=515 [M−1]−. 1H NMR (DMSO-d6, 400 MHz): δ 0.85 (m, 4H), 2.75 (m, 1H), 2.87 (s, 3H), 6.61 (m, 1H), 7.36 (d, J=8 Hz, 1H), 7.67 (d, J=11 Hz, 1H), 8.02 (s, 2H), 9.07 (s, 1H), 9.78 (s, 1H).

Aufarbeitung

  1. customquenched with saturated aqueous NH4Cl solution (5 ml)
  2. extractionextracted with EtOAc (2×10 ml)
  3. washThe combined organic solution was washed with brine (15 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5491b829407f425da8c111e6fadd5750
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063049B2

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