4-Methylmorpholine → HCID 136333985, compound

Participants

Reaction Steps

2.00 g of 5-nitro-3-pyrazolecarboxylic acid, 2.24 g of HOBt, 2.81 g of EDCI, 3.86 g of NMM and 2.58 g of 1-Boc-amino-2,2-dimethyl-1,3-propanediamine are dissolved in DMF (30 ml) and the solution is stirred at RT for 8 h. The reaction mixture is admixed with sat. NaHCO3 solution and ethyl acetate. The organic phase is removed and the aqueous phase is extracted three times more with ethyl acetate. The combined organic phases are dried over Na2SO4 and concentrated. The residue is purified by chromatography (silica gel, ethyl acetate:heptane). The 3.21 g of tert-butyl {3-[(5-nitro-1H-pyrazole-3-carbonyl)amino]-2,2-dimethylpropyl}carbamate thus obtained are dissolved in MeOH (20 ml) and admixed with 140 mg of palladium on carbon (10%). Hydrogenation is effected with hydrogen pressure 4.5 bar for 3 h. The solution is filtered and the solvent is removed under reduced pressure.

Provenance & Evidence