Diisopropylethylamine → HCID 68764188, compound

86 mg (0.45 mmol) of N-(tert-butoxycarbonyl)-L-alanine were initially charged in 5.0 ml of DMF, and 95 mg (0.49 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 95 mg (0.62 mmol) of 1-hydroxy-1H-benzotriazole hydrate and 266.13 g (2.06 mmol) of N,N-diisopropylethylamine were added. The mixture was stirred until a clear solution had been obtained. 330 mg (0.41 mmol) of 2-{4-(2-({(2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyano-6-(pyrrolidin-1-yl)pyridin-4-yl)phenoxy}ethyl L-leucinate trifluoroacetate were then added, and the mixture was stirred at room temperature for 18 h. The reaction mixture was added to 300 ml of water. The residue formed was filtered off with suction and washed with 20 ml of water. The crude product was suspended in 15 ml of methanol and sonicated in an ultrasonic bath for 5 min. The residue was filtered off with suction and washed with 10 ml of diethyl ether. This gave 0.15 g (43% of theory) of the desired target compound.

1. customhad been obtained
2. stirringthe mixture was stirred at room temperature for 18 h
3. customThe residue formed
4. filtrationwas filtered off with suction
5. washwashed with 20 ml of water
6. customsonicated in an ultrasonic bath for 5 min
7. filtrationThe residue was filtered off with suction
8. washwashed with 10 ml of diethyl ether

ORD record

ord-7a29010553304ce9b5e3afdf0acf04cd

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08420825B2