Réaction #85996

Équation de réaction

compound 2

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

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

DIEA

HATU

→

compound 13

Rendement 85.9%

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

Rendement 85.9%

Solvants

DMF

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source