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

HRID 1271706

Reaktionsgleichung

Reaktionsgleichung von HRID 1271706
FC(F)(F)OC1[CH:5]=[C:6]2[C:11](=CC=1)N=CC=[C:7]2N.[CH2:17]([O:24][C:25](=[O:42])[NH:26][CH2:27][CH2:28][CH2:29][O:30][C:31]1[CH:32]=[C:33]2[C:38](=[CH:39][CH:40]=1)[N:37]=[CH:36][CH:35]=[C:34]2[NH2:41])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.COC.C1(O)C=CC=CC=1.Br.Cl.CO.C(OC(=O)NCCCBr)C1C=CC=CC=1.[C:72](=[O:75])([O-])[O-:73].[K+].[K+].[OH-].[Na+].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>CN(C)C=O.C(O)(C)(C)C>[C:6]([O:73][C:72](=[O:75])[NH:41][C:34]1[C:33]2[C:38](=[CH:39][CH:40]=[C:31]([O:30][CH2:29][CH2:28][CH2:27][NH:26][C:25]([O:24][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:42])[CH:32]=2)[N:37]=[CH:36][CH:35]=1)([CH3:11])([CH3:7])[CH3:5]

Komponenten

13

Edukt 10

HCID 260Hydrogen BromideHCID 996Phenol2×HCID 8254Dimethyl EtherHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 199401P,P-Diphenylphosphinic azideHCID 254436Benzyl 3-bromopropylcarbamateHCID 179890496-(Trifluoromethoxy)quinolin-4-amineHCID 21893726Hydrochloride methanolHCID 69374659[3-(4-Amino-quinolin-6-yloxy)-propyl]-carbamic acid benzyl ester

Produkt 1

HCID 69374189[6-(3-Benzyloxycarbonylamino-propoxy)-quinolin-4-yl]-carbamic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

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.

Quellen und Nachweise

ORD-Eintrag
ord-eddf1860bfbc4b819aa39fa7dc1ddd3a
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07205408B2

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