Water → (1R,2R)-1-(6-CHLORO-1H-BENZIMIDAZOL-2-YL)-1-{2-[4-(4-CHLORO-PHENYL)-PIPERAZIN-1-YL]-5-OXO-6,7-DIHYDRO-5H-5lambda4-THIENO[3,2-D]PYRIMIDIN-4-YLAMINO}-PROPAN-2-OL

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	4-Chloro-2-[4-(4-chloro-phenyl)-piperazin-1-yl]-6,7-dihydro-thieno[3,2-d]pyrimidine 5-oxide	HCID 59475895	—
Reactant	(1R)-1-(5-chloro-1H-benzimidazol-2-yl)-2-methoxyethylamine	HCID 59708426	—
Solvent	Dichloromethane	HCID 6344	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	(1R,2R)-1-(6-CHLORO-1H-BENZIMIDAZOL-2-YL)-1-{2-[4-(4-CHLORO-PHENYL)-PIPERAZIN-1-YL]-5-OXO-6,7-DIHYDRO-5H-5lambda4-THIENO[3,2-D]PYRIMIDIN-4-YLAMINO}-PROPAN-2-OL	HCID 59708389	—

Reaction Conditions

Temperature	120 °C

Reaction Steps

200 mg 4-chloro-2-[4-(4-chloro-phenyl)-piperazin-1-yl]-6,7-dihydro-thieno[3,2-d]pyrimidine 5-oxide (cf Example 124), 353.41 mg (R)-1-(6-chloro-1H-benzimidazol-2-yl)-2-methoxy-ethylamine and 179.62 μl diisopropylethylamine are placed in 4 ml dioxane, heated to 120° C. in the microwave for 2×0.3 hours. Then the reaction mixture is combined with water and dichloromethane and extracted. The product is purified by semipreparative HPLC (method A). 150 mg of the product are obtained as a powder. Analytical HPLC-MS (method B): RT=1.90 min.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08822474B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-f8726b2d119c4a7c9247322e3336317d
Source note	uspto-grants-2014_09