4-N-[2-(dimethylamino)ethyl]-4-N-methylbenzene-1,4-diamine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A urea formation procedure similar to that used for the synthesis of ethyl 4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(4-(3-ethylureido)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate is used, utilizing N1-(2-(dimethylamino)ethyl)-N1-methylbenzene-1,4-diamine as the aniline component. (40%, MS=570.5 (M+H))

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepared from 1-acetyl-3-(1-ethoxy-1-ethyl-methylidene)-5,6-dimethoxy-2-indolinone and N-(2-dimethylaminoethyl)-N-methyl-p-phenylenediamine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The product was prepared according to general working method I from (2-chloro-4-trifluoromethyl-phenoxy)-acetic acid (Z2b) and N-(2-dimethylamino-ethyl)-N-methylbenzene-1,4-diamine (141b). The product was prepared

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The product was prepared according to general working method I from (2-chloro-4-trifluoromethyl-phenoxy)-acetic acid (Z2b) and N-(2-dimethylamino-ethyl)-N-methylbenzene-1,4-diamine (141b). The product was prepared

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of 5.770 g (25.842 mmol), N,N′-trimethyl-N′-(4-nitro-phenyl)-ethane-1,2-diamine (141a) and 0.60 g Pd/C (10%) in EtOH was hydrogenated for 4.5 h at 50 psi. The catalyst was filtered off and the filtrate evaporated down i. vac. The crude product was further reacted immediately. The catalyst was filtered off the filtrate evaporated down i The crude product was further reacted immediately

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The compound was prepared by zinc dust reduction of N,N,N′-trimethyl-N′-(4-nitrophenyl)ethane-1,2-diamine in analogy to the method in example 3. The product with the molecular weight of 193.29 (C11H19N3); MS (ESI): 194 ([M+H]+), was obtained in this way. MS (ESI): 194 ([M+H]+), was obtained in this way

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The compound was prepared by zinc dust reduction of N,N,N′-trimethyl-N′-(4-nitrophenyl)ethane-1,2-diamine in analogy to the method in example 3. The product with the molecular weight of 193.29 (C11H19N3); MS (ESI): 194 ([M+H]+), was obtained in this way. MS (ESI): 194 ([M+H]+), was obtained in this way

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of N,N,N′-trimethyl-N′-(4-nitrophenyl)ethane-1,2-diamine in ethanol, containing 5 drops of concentrated hydrochloric acid, is hydrogenated overnight at atmospheric pressure over 10% Pd/C. The mixture is filtered through a pad of diatomaceous earth and concentrated under reduced pressure to give N-[2-(dimethylamino)ethyl]-N-methylbenzene-1,4-diamine as a dark maroon oil. The mixture is filtered through a pad of diatomaceous earth concentrated under reduced pressure