Реакция #45423

Уравнение реакции

mixture

(2E)-3-[4-amino-3-(3-methoxy-4-{[(1-methyl-1H-indol-2-yl)carbonyl]amino}phenyl)thieno[3,2-c]pyridin-7-yl]acrylic acid

N,N-diisopropylethylamine

2-piperidin-1-ylethylamine

HBTU

→

desired product

Выход 77.3%

N-{4-[4-amino-7-((1E)-3-oxo-3-{[2-(1-piperidinyl)ethyl]amino}-1-propenyl)thieno[3,2-c]pyridin-3-yl]-2-methoxyphenyl}-1-methyl-1H-indole-2-carboxamide

Выход 77.3%

Растворители

DMF

HOBT

DMF

DMF

Условия реакции

Обработка

1. 1
   Другоеpartitioned between 1N NaOH and ethyl acetate
2. 2
   СушкаThe combined extracts were dried (Na2SO4)
3. 3
   Фильтрацияfiltered
4. 4
   Концентрированиеconcentrated

Методика

A mixture of Example 271 (30.6 mg, 0.044 mmol), N,N-diisopropylethylamine (35 μL, 0.20 mmol), 2-piperidin-1-ylethylamine (14.3 μL, 0.10 mmol), and DMF (1 mL) was treated sequentially with 0.5M (0.09 mL) of HBTU in DMF and 0.5M (0.09 mL) of HOBT in DMF. The reaction was stirred for 24 hours at ambient temperature and partitioned between 1N NaOH and ethyl acetate. The combined extracts were dried (Na2SO4), filtered, and concentrated to provide the desired product (20.4 mg, 0.034 mmol). LCMS m/e 609.2; retention time: 2.93 min.

Источник