Water → HCID 22989712, compound

A hot solution of the mixture of (2-(5-bromo(3-pyridylthio))isopropyl)methylamine and (2-(5-bromo(3-pyridylthio))propyl)methylamine (1.01 g, 3.867 mmol) in ethanol (15 mL) was treated in one portion with galactaric acid (0.406 g, 1.937 mmol). Water (3 mL) was added drop-wise, while warming the solution to reflux. To remove some white, insoluble solids, the warm solution was filtered through a glass wool plug, washing the filter plug with a warm solution of ethanol-water (4:1, v/v) (5 mL). The filtrate was diluted with ethanol (22.5 mL). The mixture was allowed to cool to ambient temperature and was allowed to stand for 16 h. The resulting solids were filtered, washed with ethanol (2×5 mL), and vacuum dried at 45° C. to give 0.512 g (36.1%) of light-beige, crystalline flakes, mp 146.5-149.5° C. Analysis indicated a 57:41 mixture of (2-(5-bromo(3-pyridylthio))-isopropyl)methylamine hemigalactarate and (2-(5-bromo(3-pyridylthio))propyl)methylamine hemigalactarate. The compound exhibits a Ki of 5500 nM.

1. temperaturewhile warming the solution
2. temperatureto reflux
3. customTo remove some white, insoluble solids
4. filtrationthe warm solution was filtered through a glass wool plug
5. washwashing the filter plug with a warm solution of ethanol-water (4:1
6. additionThe filtrate was diluted with ethanol (22.5 mL)
7. filtrationThe resulting solids were filtered
8. washwashed with ethanol (2×5 mL), and vacuum
9. customdried at 45° C.
10. customto give 0.512 g (36.1%) of light-beige, crystalline flakes, mp 146.5-149.5° C

ORD record

ord-56370b28b6af49a4913137ac4c57ef7e

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06627648B1