Tetrahydrofuran → HCID 17967993, compound

A solution of 1-{[3-benzyloxy-2-(hydroxyamino)propyl]sulphonyl}-4-(6-chloropyrimidin-4-yl)piperazine (29.5 g) in tetrahydrofuran (150 ml) and formic acid (25 ml), was added in portions to the above solution at 25° C. over 25 minutes. The solution was stirred at room temperature for 1 hour. The solution was evaporated (water-bath temperature 30° C.) and the residual gum was dissolved in ethyl acetate (500 ml). This solution was treated with saturated aqueous sodium hydrogen carbonate solution (2×250 ml) and the mixture (pH8) was stirred at room temperature for 16 hours. The ethyl acetate layer was separated, washed with saturated brine (100 ml), dried (Na2SO4), and evaporated to dryness. The residual foam was dissolved in methanol (70 ml) and the solution was stirred for 16 hours. The solution was evaporated to dryness (water-bath temperature 30° C.). The residual foam was stirred in ethanol (250 ml), solid separated and the mixture was stirred for 18 hours. The solid was collected by filtration, slurry washed with diethyl ether (100 ml), and dried to give N-[2-(benzyloxy)1-({[4-(6-chloropyrimidin-4-yl)piperazino]sulphonyl}methyl)ethyl]-N-hydroxyformamide (25.5 g). mp 118-120° C.

1. customThe solution was evaporated (water-bath temperature 30° C.)
2. dissolutionthe residual gum was dissolved in ethyl acetate (500 ml)
3. additionThis solution was treated with saturated aqueous sodium hydrogen carbonate solution (2×250 ml)
4. stirringthe mixture (pH8) was stirred at room temperature for 16 hours
5. customThe ethyl acetate layer was separated
6. washwashed with saturated brine (100 ml)
7. dry with materialdried (Na2SO4)
8. customevaporated to dryness
9. dissolutionThe residual foam was dissolved in methanol (70 ml)
10. stirringthe solution was stirred for 16 hours
11. customThe solution was evaporated to dryness (water-bath temperature 30° C.)
12. stirringThe residual foam was stirred in ethanol (250 ml)
13. customsolid separated
14. stirringthe mixture was stirred for 18 hours
15. filtrationThe solid was collected by filtration, slurry
16. washwashed with diethyl ether (100 ml)
17. customdried

ORD record

ord-2639717131c24177b6854c2814a07ba8

Source dataset

uspto-grants-2008_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07342020B2