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Preparation of 9-ethyl-6,6-dimethyl-8-(4-morpholinopiperidin-1-yl)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

IP.com Disclosure Number: IPCOM000250294D
Publication Date: 2017-Jun-23
Document File: 2 page(s) / 237K

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Preparation of 9-ethyl-6,6-dimethyl-8-(4-morpholinopiperidin-1-yl)-11-oxo-6,11-dihydro-5H- benzo[b]carbazole-3-carbonitrile

6-cyano-2-(2-(4-ethyl-3-(4-morpholinopiperidin-1-yl)phenyl)propan-2-yl)-1H-indole-3-

carboxylic acid (1.0 g) was dissolved in a mixture of dimethylacetamide (19 ml),

diisopropylethylamine (2.4 ml) and acetic anhydride (0.5 ml) under nitrogen stream. The mixture

was stirred at 90ºC for 1 h. After cooling down, methanol (7 ml) and subsequently water (12.5

ml) were added. The precipitated solid was filtered, washed with a mixture of methanol:water

1:2 and dried at 45ºC under vacuum to obtain the title compound (0.780 g, 81% yield; XRD fig.

1).

1H NMR (400 MHz, DMSO-d6): δ 12.69 (s, 1H), 8.32 (dd, J = 8.2, 0.7 Hz, 1H), 8.04 (s, 1H), 8.06 –

7.97 (m, 1H), 7.60 (dd, J = 8.2, 1.4 Hz, 1H), 7.33 (s, 1H), 3.61 (s, 3H), 3.30 – 3.18 (m, 2H), 2.82 –

2.65 (m, 3H), 2.53 (s, 2H), 1.94 (d, J = 8.3 Hz, 1H), 1.75 (s, 4H), 1.60 (d, J = 12.8 Hz, 1H), 1.27 (t, J

= 7.5 Hz, 2H).

The title compound (0.5 g) was suspended in methanol (10 ml), heated to 60ºC and hold for 1 h.

The suspension was cooled down to room temperature. The solid was filtered, washed with

methanol and dried at 45ºC under vacuum to obtain the title compound (0.49 g, 98% yield; XRD

fig. 2).

Figure 1. XRD of 9-ethyl-6,6-dimethyl-8-(4-morpholinopiperidin-1-yl)-11-oxo-6,11-dihydro-5H-

benzo[b]carbazole-3-carbonitrile

Figure 2. XRD of 9-ethyl-6,6-dimethyl-8-(4-morpholinopiperidin-1-yl)-11-oxo-6,11-dihydro-5H-

benz...