تفاعل #60265

معادلة التفاعل

cyclopropyl methyl hydroxylamine hydrochloride

PyBOP

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

Hunig's base

→

pure desired product

المردود 70.0%

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

المردود 70.0%

المذيبات

ethyl acetate

THF methylene chloride

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONis added
2. 2
   workup.WAITAfter 16 hours
3. 3
   غسيلwashed with 0.1 N HCl, saturated NaHCO3, and brine
4. 4
   تجفيفThe organic layer is dried (Na2SO4)
5. 5
   تركيزconcentrated under reduced pressure
6. 6
   أخرىThe crude yellow residue is purified by FCC
7. 7
   غسيلeluted with ethyl acetate

الإجراء التجريبي

6-(4-Bromo-2-methyl-phenylamino)-7-fluoro-3-pent-4-enyl-3H-benzoimidazole-5-carboxylic acid 10d (0.390 g, 0.902 mmol) is dissolved in 1:1 THF/methylene chloride (6 mL) and Hunig's base (0.346 mL, 1.985 mmol) is added followed by PyBOP (0.563 g, 1.083 mmol). After 10 minutes, cyclopropyl methyl hydroxylamine hydrochloride (0.134 g, 1.083 mmol) is added. After 16 hours, the reaction mixture is diluted with ethyl acetate and washed with 0.1 N HCl, saturated NaHCO3, and brine. The organic layer is dried (Na2SO4) and concentrated under reduced pressure. The crude yellow residue is purified by FCC eluted with ethyl acetate to give 0.315 g (70%) pure desired product as a yellow solid: MS APCI (+) m/z 503, 501 (M+1 Br pattern) detected.

المصدر