Propionic Acid → N-((S)-1-{2-[4-(4-CHLORO-PHENYL)-PIPERAZIN-1-YL]-5-OXO-6,7-DIHYDRO-5H-5lambda4-THIENO[3,2-D]PYRIMIDIN-4-YL}-PYRROLIDIN-2-YLMETHYL)-PROPIONAMIDE

https://huagongshe.com/reaction/1911066

Participants

Role	Name	HCID	Charge
Reactant	Propionic Acid	HCID 1032	—
Reactant	Diisopropylethylamine	HCID 81531	—
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 66735925	HCID 66735925	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Solvent	Water	HCID 962	—
Solvent	Dichloromethane	HCID 6344	—
Product	N-((S)-1-{2-[4-(4-CHLORO-PHENYL)-PIPERAZIN-1-YL]-5-OXO-6,7-DIHYDRO-5H-5lambda4-THIENO[3,2-D]PYRIMIDIN-4-YL}-PYRROLIDIN-2-YLMETHYL)-PROPIONAMIDE	HCID 59708458	—

Reaction Steps

17 μl propionic acid are placed in 800 μl dimethylsulphoxide, and 78 μl diisopropylethylamine and 94 mg O-(7-azabenzotriazol-1-yl-)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) are added. The mixture is stirred for 0.3 hours at ambient temperature, then a solution of 100 mg C-((S)-1-{2-[4-(4-chloro-phenyl)-piperazin-1-yl]-5-oxo-6,7-dihydro-5H-5λ4-thieno [3,2-d]pyrimidin-4-yl}-pyrrolidin-2-yl)-methylamine trifluoroacetate, Diastereomer 2 (Example 226) (see scheme 3, 3.17.2), in 700 μl dimethylsulphoxide is added. The reaction mixture is stirred for 15 hours at ambient temperature and then combined with water and dichloromethane. The organic phase is dried and evaporated to dryness. The product is purified by preparative HPLC (method A). 84 mg of the product are obtained as an oil. Analytical HPLC-MS (method D): RT 32 1.19 min.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08604039B2
Source dataset	uspto-grants-2013_12
ORD ID	ord-ba9e1f9623164a4daa6139bfed0e4621
Source note	uspto-grants-2013_12