Diisopropylethylamine → HCID 66602058, compound

https://huagongshe.com/reaction/2064363

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Piperazin-2-one	HCID 231360	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	HCID 42640886	HCID 42640886	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 66602058	HCID 66602058	55.5%

Reaction Steps

The reaction was carried out under argon. 2-[(6S)-5-Cyano-6-[4-cyano-2-(methylsulfonyl)phenyl]-4-methyl-2-oxo-3-[3-(trifluoromethyl)phenyl]-3,6-dihydropyrimidin-1(2H)-yl]acetic acid (50 mg, 96 μmol; Example 21) was initially charged in DMF (2 ml), HATU (183 mg, 482 μmol, 5 eq.) was added at 0° C. and the mixture was stirred for 20 min. 2-Oxopiperazine (48.3 mg, 482 μmol, 5 eq.) and N,N-diisopropylethylamine (62 mg, 482 μmol, 5 eq.) were then added, and the mixture was stirred at RT for 30 min until complete conversion had been achieved (HPLC control). The reaction mixture was then concentrated under reduced pressure and the crude product was purified by preparative HPLC (column: Gromsil C-18 10 μm; mobile phase: acetonitrile/water+0.1% TFA 10:90→90:10). This gave the title compound as a colorless solid (32 mg, 55% of theory).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08288402B2
Source dataset	uspto-grants-2012_10
ORD ID	ord-db2813e8e5474388b20e6d9e032e08e5
Source note	uspto-grants-2012_10