Reaktion #45423

Reaktionsgleichung

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

Ausbeute 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

Ausbeute 77.3%

Lösungsmittel

DMF

HOBT

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigepartitioned between 1N NaOH and ethyl acetate
2. 2
   TrocknenThe combined extracts were dried (Na2SO4)
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated

Vorschrift

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.

Quelle