Hydrogen Bromide → [6-(3-Benzyloxycarbonylamino-propoxy)-quinolin-4-yl]-carbamic acid tert-butyl ester

Participants

Reaction Steps

Example 180 was prepared from 6-trifluoromethoxy-quinolin-4-ylamine (prepared from 4-trifluoromethoxyaniline by addition to methyl propiolate, cyclisation in refluxing Dowtherm, reaction with trifluoromethane sulfonic anhydride and heating with n-propylamine) by the method of Example 7b-d. Example 181 was prepared from aldehyde 14a and [3-(4-amino-quinolin-6-yloxy)-propyl]-carbamic acid benzyl ester (prepared from Example (1a) by cleavage of the methyl ether to the corresponding phenol with concentrated hydrobromic acid, esterification using concentrated hydrochloric acid/methanol, alkylation of the phenol with (3-bromo-propyl)-carbamic acid benzyl ester using potassium carbonate in N,N-dimethylformamide, hydrolysis of the methyl ester to the corresponding acid with aqueous sodium hydroxide, Curtius rearrangement of the acid with diphenylphosphoryl azide in tert-butanol to give [6-(3-benzyloxycarbonylamino-propoxy)-quinolin-4-yl]-carbamic acid tert-butyl ester then standard treatment with trifluoroacetic acid) by the method of Example 7b-d followed by hydrogenation.

Provenance & Evidence