Dichloromethane → HCID 58010071, Verbindung

A round-bottomed flask was charged with 2-hydrazinyl-5-tosyl-5H-pyrrolo[2,3-b]pyrazine (2.0 g, 6.6 mmol, Step J) and DCM (40 mL) to give a brown suspension. 4-(tert-Butoxycarbonylamino)-2-ethylcyclopentanecarboxylic acid (2.0 g, 7.8 mmol, Step G), HATU (2.51 g, 6.59 mmol), and TEA (4.59 mL, 33.0 mmol) were added to the suspension and the resulting mixture was stirred at ambient temperature for about 24 h with dissolution occurring after about 2 h. Water (20 mL) was added and the layers were partitioned. The organic layer was washed with additional water (2×15 mL), brine (2×25 mL), dried over anhydrous MgSO4, filtered, and solvent was removed under reduced pressure to give a brown residue. The crude material was purified by silica gel chromatography eluting with a gradient of 0-10% MeOH/DCM. The recovered impure material was re-purified by silica gel chromatography eluting with a gradient of 0-10% MeOH/DCM. The product-containing fractions from the two columns were combined and concentrated to give tert-butyl-3-ethyl-4-(2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)hydrazinecarbonyl)cyclopentylcarbamate (2.45, 69%) as a brown solid: LC/MS (Table 2, Method d) Rt=1.47 min; MS m/z: 543 (M+H)+.

1. customto give a brown suspension
2. waitoccurring after about 2 h
3. customthe layers were partitioned
4. washThe organic layer was washed with additional water (2×15 mL), brine (2×25 mL)
5. dry with materialdried over anhydrous MgSO4
6. filtrationfiltered
7. customsolvent was removed under reduced pressure
8. customto give a brown residue
9. customThe crude material was purified by silica gel chromatography
10. washeluting with a gradient of 0-10% MeOH/DCM
11. customThe recovered impure material was re-purified by silica gel chromatography
12. washeluting with a gradient of 0-10% MeOH/DCM
13. concentrationconcentrated

ORD-Eintrag

ord-b2663156099b427a8038b78cdfb0e221

Quelldatensatz

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08962629B2