HCID 22842497, compound → HCID 19893845, compound

A solution of (2S,4S,5S)-N-butyl-6-cyclohexyl-4-hydroxy-2-isopropyl-5-[3-(1-triphenylmethylimidazol-4-yl)-(2RS)-2-(8-propyl-6-(3-pyridyl)-1,2,4-triazolo[4,3-a]pyrazin-3-yl)propionamido]hexanamide (A) (187 mg) in trifluoroacetic acid (8 ml) and water (2 ml) was stirred for 75 minutes. Volatile material was removed by evaporation and saturated sodium hydrogen carbonate solution (10 ml) added to the residue. The mixture was extracted with chloroform (2×20 ml) and the combined extracts were washed successively with water (10 ml) and saturated sodium chloride solution (10 ml) and dried (MgSO4). The solvent was removed by evaporation and the residue triturated with ether to give (2S,4S,5S)-N-butyl-6-cyclohexyl-4-hydroxy-5-[3-a]pyrazin-3-yl)propionamido]-2-isopropylhexanamide as a white powder (60 mg); NMR (d6 -DMSO/d4 -acetic acid): 0.3-1.7 (complex m, 32H), 2.0 (m, 3H), 2.9-3.9 (complex m, 8H), 4.9 (m, 1H), 7.3 (m, 1H), 7.6 (m, 1H), 8.5 (m, 2H), 8.7 (m, 1H), 9.25 and 9.35 (both S, ratio 1:1, total 1H), 9.3 (m, 1H); mass spectrum (+ve FAB, DMSO): 686 (M+H)+, 360, 332.

1. customVolatile material was removed by evaporation and saturated sodium hydrogen carbonate solution (10 ml)
2. additionadded to the residue
3. extractionThe mixture was extracted with chloroform (2×20 ml)
4. washthe combined extracts were washed successively with water (10 ml) and saturated sodium chloride solution (10 ml)
5. dry with materialdried (MgSO4)
6. customThe solvent was removed by evaporation
7. customthe residue triturated with ether

ORD record

ord-5c768d6dc372468aaa0c2bf3c90ccffc

Source dataset

uspto-grants-1992_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05091425