HCID 21075760, compound → HCID 178517343, compound

HRID 1035488Notes

Reaction equation

HRID 1035488 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

4

Reactant 2

HCID 21075760HCID 21075760, compoundHCID 66650257HCID 66650257, compound

Product 2

HCID 178517343HCID 178517343, compoundHCID 178517344HCID 178517344, compound

Procedure

In step (11) of Reaction Scheme IV, the benzyl group of a benzyloxy-1H-imidazo[4,5-c]quinoline or benzyloxy-1H-imidazo[4,5-c][1,5]naphthyridine of Formula XLV is cleaved to provide a 1H-imidazo[4,5-c]quinolinol or 1H-imidazo[4,5-c][1,5]naphthyridinol of Formula XLVI. 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 XLV 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

  1. customIn step (11) of Reaction Scheme IV

Sources & evidence

ORD record
ord-2fea3a49269f4817957fc49e5d867611
Source dataset
uspto-grants-2013_10
Patent number
US08546383B2

Reaction notes

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