HCID 21075760, compound → HCID 178517343, compound
Reaction equation
C([O:8][N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[CH:13][C:12]=2[N:11]=[CH:10]1)C1C=CC=CC=1.C([O:29][N:30]1[C:42]2[C:41]3[N:40]=[CH:39][CH:38]=[CH:37][C:36]=3[N:35]=[CH:34][C:33]=2[N:32]=[CH:31]1)C1C=CC=CC=1>>[NH:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[CH:13][C:12]=2[N:11]=[C:10]1[OH:29].[NH:30]1[C:42]2[C:41]3[N:40]=[CH:39][CH:38]=[CH:37][C:36]=3[N:35]=[CH:34][C:33]=2[N:32]=[C:31]1[OH:8]Participants
Procedure
In step (12) of Reaction Scheme V, the benzyl group of a benzyloxy-1H-imidazo[4,5-c]quinoline or benzyloxy-1H-imidazo[4,5-c][1,5]naphthyridine of Formula LXII is cleaved to provide a 1H-imidazo[4,5-c]quinolinol or 1H-imidazo[4,5-c][1,5]naphthyridinol of Formula LXIII. The cleavage is conveniently carried out on a Parr apparatus under hydrogenolysis conditions using a suitable heterogeneous catalyst such as palladium on carbon in a solvent such as ethanol. Alternatively, the reaction can be carried out by transfer hydrogenation in the presence of a suitable hydrogenation catalyst. The transfer hydrogenation is conveniently carried out by adding ammonium formate to a solution of a compound of Formula LXII in a suitable solvent such as ethanol in the presence of a catalyst such as palladium on carbon. The reaction is carried out at an elevated temperature, for example, the reflux temperature of the solvent.
Workup
- customIn step (12) of Reaction Scheme V
Sources & evidence
- ORD record
- ord-769136430cad4d368df225ca4d02abcf
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08034938B2
Reaction notes
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