Sodium Carbonate → tert-butyl {2-[{2-[3-(2-fluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]ethyl}(methyl)amino]ethyl}methylcarbamate

HRID 1818810Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1818810
Br[CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])[S:5]1(=[O:21])=[O:20].[CH3:22][N:23]([CH2:31][CH2:32][NH:33][CH3:34])[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[F:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[N:6]1[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:4]([CH2:3][CH2:2][N:33]([CH3:34])[CH2:32][CH2:31][N:23]([CH3:22])[C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[S:5]1(=[O:21])=[O:20]

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 14403871tert-Butyl methyl(2-(methylamino)ethyl)carbamateHCID 68711997HCID 68711997, Verbindung

Produkt 1

HCID 86621288tert-butyl {2-[{2-[3-(2-fluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]ethyl}(methyl)amino]ethyl}methylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
125 °C

Versuchsvorschrift

A mixture of 1-(2-bromoethyl)-3-(2-fluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (171 mg, 0.461 mmol), tert-butyl methyl[2-(methylamino)ethyl]carbamate (695 mg, 3.69 mmol, 8 equiv.), sodium carbonate (489 mg, 4.61 mmol, 10 equiv.) and N,N-dimethylformamide (5 mL) was sealed and heated at 125° C. for 5 h. After cooling, the reaction mixture was partitioned between ethyl acetate (40 mL) and water (40 mL). The organic layer was washed with brine, dried (anhydrous sodium sulfate), and concentrated. The crude liquid was pre-adsorbed onto Florisil and purified via Isco flash column chromatography (12-g redisep silica gel column, 15-70% ethyl acetate/hexane) to give tert-butyl {2-[{2-[3-(2-fluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]ethyl}(methyl)amino]ethyl}methylcarbamate as a viscous, colorless liquid. Yield: 142 mg (64%). MS (ESI) m/z 479.0 ([M+H]+). HRMS: calcd for C23H31FN4O4S+H+, 479.2123; found (ESI, [M+H]+), 479.2129. HPLC purity 96.6% at 210-370 nm, 9.0 min.; Xterra RP18, 3.5 u, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min.

Aufarbeitung

  1. customwas sealed
  2. temperatureAfter cooling
  3. customthe reaction mixture was partitioned between ethyl acetate (40 mL) and water (40 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried (anhydrous sodium sulfate)
  6. concentrationconcentrated
  7. custompurified via Isco flash column chromatography (12-g redisep silica gel column, 15-70% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-bae0199e3fbc421c993ef6f376dd56a8
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07601722B2

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