4-(N,N-dimethlyamino)pyridine in dichloromethane 1 h; Ambient temperature;

1: dimethylformamide 2: H2 / Pd/C / methanol View Scheme

1: dimethylformamide 2: H2 / Pd/C / methanol 3: dimethylformamide View Scheme

in N,N-dimethyl-formamide

1: 1) NEt3, 2) N-methylmorpholine / 1) DMF, 0 deg C, 1 h, then rt, 12 h, 2) pH 8, 24 h 2: aq. NaOH / acetone / 2 h / Ambient temperature 3: 75 percent / N-methylmorpholine, dicyclohexylcarbodiimide, HOBt / dimethylformamide / 1) pH 8, -20 deg C, 1 h, 2) rt, 48 h 4: 90 percent / aq. NaOH / dioxane; H2O / 1 h 5: H2 / 10percent Pd/C / dimethylformamide / 1 h View Scheme

sodium hydrogencarbonate in ethanol Ambient temperature;

N-ethyl-N,N-diisopropylamine in N,N-dimethyl-formamide 2 h; Ambient temperature;

1: 87 percent / N,N-diisopropyl N-ethylamine / dimethylformamide / 2 h / Ambient temperature 2: H2, cc. HCl / Pd/C / ethanol / 5 h View Scheme

sodium hydrogencarbonate in ethanol Ambient temperature;

(i) Et3N, dimethoxyethane, (ii) N,N-dimethyl-propanediyl-diamine; Multistep reaction;