Reaktion #85996

Reaktionsgleichung

compound 2

3-Amino-3H-imidazole-4-carboxylic acid methyl ester

1-Benzyl-4-trifluoromethyl-pyrrolidine-3-carboxylic acid

DIEA

HATU

→

compound 13

Ausbeute 85.9%

3-[(1-Benzyl-4-trifluoromethyl-pyrrolidine-3-carbonyl)-amino]-3H-imidazole-4-carboxylic acid methyl ester

Ausbeute 85.9%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resulting reaction mixture
2. 2
   SonstigeThe reaction was quenched with water (100 mL) when it
3. 3
   ExtraktionThe aqueous solution was extracted with EtOAc (80 mL×3)
4. 4
   WaschenThe combined organic phase was washed with brine
5. 5
   Einengenconcentrated
6. 6
   Sonstigeto afford the crude product
7. 7
   SonstigeThe residue was purified by silica gel column (eluted with PE/EA=5:1 to 1:2)

Vorschrift

To a solution of compound 2 (2.0 g, 14.1 mmol), 1-Benzyl-4-trifluoromethyl-pyrrolidine-3-carboxylic acid (4.06 g, 14.9 mmol) and DIEA (10 mL, 42.5 mmol) in DMF (30 mL) was added HATU (8.1 g, 21.2 mmol). The resulting reaction mixture was stirred at r.t. overnight. The reaction was monitored by LC-MS. The reaction was quenched with water (100 mL) when it was complete. The aqueous solution was extracted with EtOAc (80 mL×3). The combined organic phase was washed with brine and concentrated to afford the crude product. The residue was purified by silica gel column (eluted with PE/EA=5:1 to 1:2) to afford compound 13 (4.8 g, 85.6% yield) as white oil. LC-MS: m/z 397 [M+1]+. 1H NMR (400 MHz, CDCl3): δ 8.00 (br. s, 1H), 7.70 (s, 1H), 7.65 (s, 1H), 7.34˜7.28 (m, 5H), 3.81 (s, 3H), 3.78˜3.72 (m, 2H), 3.41˜3.38 (m, 1H), 3.30˜3.24 (m, 2H), 3.14˜3.12 (m, 1H), 2.71˜2.67 (m, 1H), 2.58˜2.53 (m, 1H).

Quelle