Reaktion #172862

Reaktionsgleichung

LiOH

TFA

4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-3a-(2-(pyridin-3-ylamino)ethylamino)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoic acid

2-bromo-1-methyl-1H-imidazole

→

title compound

4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-(2-(1-methyl-1H-imidazol-2-ylamino)ethylamino)-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoic acid

Lösungsmittel

methanol

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeoccurred spontaneously during the course of the amination reaction
2. 2
   SonstigeThe product was isolated
3. 3
   Sonstigeafter reverse phase preparative HPLC purification

Vorschrift

The title compound was prepared following a similar procedure as described for the synthesis of 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-3a-(2-(pyridin-3-ylamino)ethylamino)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoic acid, except 2-bromo-1-methyl-1H-imidazole (0.015 g, 8.88 μL, 0.091 mmol) was used in place of 3-bromopyridine. Also, addition of LiOH, water and methanol were unnecessary for this example, as the ester hydrolysis occurred spontaneously during the course of the amination reaction. The product was isolated after reverse phase preparative HPLC purification using Prep HPLC Method 8 as a beige solid (38.1 mg, 51.5% yield) bis TFA salt. LCMS: m/e 653.4 (M+H)+, 3.88 min (method 16). 1H NMR (500 MHz, 1:1 mixture of CDCl3 and MeOD, MeOD lock) δ ppm 7.91 (d, J=8.2 Hz, 2H), 7.19 (d, J=7.9 Hz, 2H), 6.86 (s, 1H), 6.83-6.79 (m, 1H), 5.28 (d, J=5.5 Hz, 1H), 4.84 (s, 1H), 4.73 (s, 1H), 4.71 (br. s., 1H), 3.98-3.82 (m, 2H), 3.58 (s, 3H), 3.25 (br. s., 1H), 2.89-2.78 (m, 1H), 2.18-2.07 (m, 3H), 2.05-1.92 (m, 3H), 1.90-1.79 (m, 1H), 1.72 (s, 4H), 1.69 (br. s., 1H), 1.62-1.54 (m, 3H), 1.53-1.47 (m, 3H), 1.46-1.34 (m, 5H), 1.28-1.20 (m, 2H), 1.18-1.12 (m, 1H), 1.11 (s, 3H), 1.09-1.03 (m, 4H), 1.01 (s, 3H), 0.93 (br. s., 3H), 0.93 (br. s., 3H).

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