Diisopropylethylamine → HCID 178433037, compound

Temperature

20 °C

To 2-methyl-1,3-thiazole-4-carboxylic acid (24 mg) in DMF (0.375 ml) was added HATU (69 mg) followed by DIPEA (0.043 ml), and the solution stirred for 10 min at 20° C. To this was then added a solution of 3-fluoro-6-(1H-indol-4-yl)-1H-indazol-4-amine (67 mg) in DMF (0.375 ml) and the top was placed on the vial which had been pierced with a needle. The solution was stirred at 20° C. for 73 h, heated at 50° C. for 3 h, then left to stand for 3.5 days. A further portion of 2-methyl-1,3-thiazole-4-carboxylic acid (0.024 g) in DMF (0.375 ml) was treated with HATU (0.069 g) followed by DIPEA (0.043 ml). This solution was stirred for 15 min at 20° C. then added to the original reaction mixture. This was then stirred at 20° C. for a further 72 h then loaded onto a dried aminopropyl SPE cartridge (1 g) which had been preconditioned with chloroform. The material was left on the cartridge for 2 h, then the cartridge was eluted with methanol (3 column volumes) and the solvent blown off. This was purified directly by mass directed preparative HPLC (Method A). The residue was azeotroped with methanol (5 ml) to give the title compound (7 mg) as a beige solid.

1. stirringThe solution was stirred at 20° C. for 73 h
2. temperatureheated at 50° C. for 3 h
3. waitleft
4. waitto stand for 3.5 days
5. stirringThis solution was stirred for 15 min at 20° C.
6. additionthen added to the original reaction mixture
7. stirringThis was then stirred at 20° C. for a further 72 h
8. waitThe material was left on the cartridge for 2 h
9. washthe cartridge was eluted with methanol (3 column volumes)
10. customThis was purified directly by mass
11. customThe residue was azeotroped with methanol (5 ml)

ORD record

ord-6fc31eb79ff441058a51713b4ae8bdf9

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08658635B2