反应详情

温度

80 °C

2-[(Aminocarbonyl)amino]-5-[4-formylphenyl]thiophene-3-carboxamide (0.1 g) was stirred in a mixture of DME (10 ml) and DMA(5 ml). 2-(Methylamino)ethanol (0.13 g) was added, followed by trimethyl orthoformate (5 ml) and acetic acid (0.5 ml). The reaction was stirred at 80° C. for 20 min, and then polymer-supported cyanoborohydride (0.45 g) was added. The reaction was stirred at 80° C. for a further 2 h, and then polymer-supported benzaldehyde (0.5 g) was added. The resins were removed by filtration and the filtrate was passed through a 5 g SCX column, washing with methanol (25 ml). The product was eluted using 1M methanolic ammonia (45 ml) and this solution was evaporated to dryness under reduced pressure. Purification by chromatography on silica, eluting with DCM/methanol (9:1), gave the product as an off-white solid (0.072 g). MS (ES) 349 (M+H)+. 1H NMR (DMSO-D6) 2.15 (s, 3H), 2.45 (m, 2H), 3.50 (m, 4H), 4.35 (t, 1H), 6.90 (s, 2H), 7.25-7.40 (m, 3H), 7.50 (d, 2H), 7.70 (s, 1H), 7.75 (s, 1H), 11.00 (s, 11).

1. stirringThe reaction was stirred at 80° C. for a further 2 h
2. customThe resins were removed by filtration
3. washwashing with methanol (25 ml)
4. washThe product was eluted
5. customthis solution was evaporated to dryness under reduced pressure
6. customPurification by chromatography on silica
7. washeluting with DCM/methanol (9:1)