Reaktion #60259

Reaktionsgleichung

Cyclopropyl methyl hydroxylamine hydrochloride

6-(4-Bromo-2-chloro-phenylamino)-7-fluoro-3H-benzoimidazole-5-carboxylic acid

HOBt

EDCI

triethyl amine

→

pure desired product

Ausbeute 89.0%

6-(4-Bromo-2-chloro-phenylamino)-7-fluoro-3H-benzoimidazole-5-carboxylic acid cyclopropylmethoxy-amide

Ausbeute 89.0%

Lösungsmittel

ethyl acetate

water

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONis added
2. 2
   Sonstigethe layers separated
3. 3
   WaschenThe organic layer is washed with saturated NH4Cl, brine, saturated NaHCO3, water and brine
4. 4
   TrocknenThe organic layer is dried (MgSO4)
5. 5
   Einengenconcentrated under reduced pressure

Vorschrift

6-(4-Bromo-2-chloro-phenylamino)-7-fluoro-3H-benzoimidazole-5-carboxylic acid 10b (22 mg, 0.057 mmol) is dissolved in DMF (1 mL) and HOBt (9 mg, 0.062 mmol) followed by triethyl amine (18 μL, 0.132 mmol) is added. Cyclopropyl methyl hydroxylamine hydrochloride (8 mg, 0.062 mmol) is added followed by EDCI (14 mg, 0.074 mmol). After 16 hours, the reaction mixture is diluted with ethyl acetate and water and the layers separated. The organic layer is washed with saturated NH4Cl, brine, saturated NaHCO3, water and brine. The organic layer is dried (MgSO4) and concentrated under reduced pressure to give 23 mg (89%) pure desired product. MS APCI (+) m/z 455, 453 (M+Br pattern) detected; MS APCI (−) m/z 453, 451 (M−Br pattern) detected; 1H NMR (400 MHz, DMSO-d6) δ 11.69 (broad s, 1H), 8.43 (s, 1H), 7.62 (d, 1H), 7.28 (dd, 1H), 6.42 (m, 1H), 3.63 (d, 2H), 1.03 (m, 1H), 0.48 (m, 2H), 0.19 (m, 2H); 19F NMR (376 MHz, DMSO-d6) −132.95 (s).

Quelle