Реакция #10391

Уравнение реакции

4-[3-(tert-butoxycarbonylamino)pyrrolidin-1-yl]-5-chloro-2,3-difluorobenzoic acid ethyl ester

cyclopropylamine

→

title compound

Выход 48.7%

4-[3-(tert-Butoxycarbonylamino)pyrrolidin-1-yl]-5-chloro-2-cyclopropylamino-3-fluorobenzoic acid ethyl ester

Выход 48.7%

Растворители

N,N-dimethylacetamide

Условия реакции

Обработка

1. 1
   КонцентрированиеThe solution is then concentrated under high vacuum
2. 2
   Другоеpurified by column chromatography (1:9 ethyl acetate/hexanes)

Методика

A solution of 4-[3-(tert-butoxycarbonylamino)pyrrolidin-1-yl]-5-chloro-2,3-difluorobenzoic acid ethyl ester (Example 21, 3.75 g, 9.3 mmol) and cyclopropylamine (14.0 mL, 201 mmol) in N,N-dimethylacetamide (5 mL) is heated in a sealed glass tube for 48 hours at 100° C. The solution is then concentrated under high vacuum and purified by column chromatography (1:9 ethyl acetate/hexanes) to afford the title compound (2.0 g). 1H NMR (CDCl3): δ 7.64 (d, 1H), 7.56 (bs, 1H), 4.98–4.90 (bd, 1H), 4.40–4.20 (m, 3H), 3.78–3.63 (m, 4H), 2.97–2.83 (m, 1H), 2.35–2.21 (m, 1H), 1.93–1.81 (m, 1H), 1.46 (s, 9H), 1.38 (t, 3H), 0.75–0.61 (m, 2H), 0.57–0.50 (m, 2H).

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