Diisopropylethylamine → N-{[(2S)-4-(2,3-dichlorobenzyl)morpholin-2-yl]methyl}-N'-prop-2-ynylurea

A solution of Intermediate 22 (0.024 g) in dichloromethane (1 ml) was stirred with Intermediate 20 (0.033 g) and N,N-diisopropylethylamine (0.022 ml) for 3 h at 23° C. The solvent was removed in vacuo and the residue was purified by solid phase extraction (Isolute SCX sulphonic acid column) eluting with methanol followed by 10% 0.880 ammonia solution in methanol. The basic fraction was concentrated in vacuo, and the residue was dissolved in dichloromethane (5 ml), and the solution shaken with polystyrene methyl isocyanate resin (Argonaut technologies, 0.256 g, 1.43 mmol/g) for 16 h. The solution Was drained from the resin and the resin washed with dichloromethane (8 ml); the combined filtrate and washings were concentrated in vacuo to give the title compound as a pale yellow gum (0.02 g).

1. customThe solvent was removed in vacuo
2. customthe residue was purified by solid phase extraction (Isolute SCX sulphonic acid column)
3. washeluting with methanol
4. concentrationThe basic fraction was concentrated in vacuo
5. dissolutionthe residue was dissolved in dichloromethane (5 ml)
6. washthe resin washed with dichloromethane (8 ml)
7. concentrationthe combined filtrate and washings were concentrated in vacuo

ORD-Eintrag

ord-e36ede6d838840ebaf43c9322f13bf2c

Quelldatensatz

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07157457B2