Process for preparing quinoline amines
AssigneeMinnesota Mining and Manufacturing Company
InventorsNick Nikolaides, Kyle J. Lindstrom
Life of this patent
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Abstract
A process that involves reacting a 3-nitroquinoline-2,4-disulfonate with an amine or a substituted amine to selectively aminate at the 4-position to yield 1H-imidazo[4,5-c]quinolin-4-amines is disclosed.
Claims10
A process for preparing a 4-(substituted)amino-3-nitroquinoline-2-sulfonate comprising the steps of:
- (i) providing a 3-nitroquinoline-2,4-disulfonate;
- (ii) reacting the compound from step (i) with an amine to provide a 4-(substituted)amino-3nitroquinoline-2-sulfonate.
A process for preparing a 4-(substituted)amino-3 -nitroquinoline substituted at the 2-position with a hydrogenolyzable amino substituent, comprising the steps of:
- (i) providing a 3-nitroquinoline-2,4-disulfonate;
- (ii) reacting the compound from step (i) with an amine to provide a 4-(substituted)amino-3-nitroquinoline-2-sulfonate;
- and
- (iii) reacting the compound from step (ii) with a hydrogenolyzable amine to provide a 4-(substituted)amino-3-nitroquinoline substituted at the 2-position with a hydrogenolyzable amino substituent.
A process for preparing a 3-amino-4-(substitute)aminoquinoline substituted at the 2-position with a hydrogenolyzable amino substituent comprising the steps of:
- (i) providing a 3-nitroquinoline-2,4-disulfonate;
- (ii) reacting the compound from step (i) with an amine to provide a 4-(substituted)amino-3-nitroquinoline-2-sulfonate;
- (iii) reacting the compound from step (ii) with a hydrogenolyzable amine to provide a 4-(substituted)amino-3-nitroquinoline substituted at the 2-position with a hydrogenolyzable amino substituent;
- and
- (iv) reducing the compound from step (iii) to provide a 3-amino-4-(substituted)aminoquinoline substituted at the 2-position with a hydrogenolyzable amino substituent.
A process for preparing a (1-substituted) (2-substituted) 1H-imidazo[4,5-c]-quinoline substituted at the 4-position with a hydrogenolyzable amino substituent, comprising the steps of:
- (i) providing a 3-nitroquinoline-2,4-disulfonate;
- (ii) reacting the compound from step (i) with an amine to provide a 4-(substituted)amino-3-nitroquinoline-2-sulfonate;
- (iii) reacting the compound from step (ii) with a hydrogenolyzable amine to provide a 4-(substituted)amino-3-nitroquinoline substituted at the 2-position with a hydrogenolyzable amino substituent;
- (iv) reducing the compound from step (iii) to provide a 3-amino-4-(substituted)aminoquinoline substituted at the 2-position with a hydrogenolyzable amino substituent;
- and
- (v) reacting the compound from step (iv) with a carboxylic acid or an equivalent thereof to provide a (1-substituted) (2-substituted) 1H-imidazo[4,5-c]quinoline substituted at the 4-position with a hydrogenolyzable amino substituent.
A process for preparing a (1-substituted) (2-substituted) 1H-imidazo[4,5-c]-quinolin-4-amine, comprising the steps of:
- (i) providing a 3-nitroquinoline-2,4-disulfonate;
- (ii) reacting the compound from step (i) with an amine to provide a 4-(substituted)amino-3-nitroquinoline-2-sulfonate;
- (iii) reacting the compound from step (ii) with a hydrogenolyzable amine to provide a 4-(substituted)amino-3-nitroquinoline substituted at the 2-position with a hydrogenolyzable amino substituent;
- (iv) reducing the compound from step (iii) to provide a 3-amino-4-(substituted)aminoquinoline substituted at the 2-position with a hydrogenolyzable amino substituent;
- (v) reacting the compound from step (iv) with a carboxylic acid or an equivalent thereof to provide a (1-substituted) (2-substituted) 1H-imidazo[4,5-c] quinoline substituted at the 4-position with a hydrogenolyzable amino substituent;
- and
- (vi) hydrogenolyzing the compound from step (v) to provide a (1-substituted) (2-substituted) 1H-imidazo[4,5-c]quinolin-4-amine.
A compound selected from the group consisting of 3-nitro-2,4-bis [(trifluoromethyl)sulfonyloxy]quinoline and 3-nitro-2,4-bis(methylsulfonyloxy)quinoline.
A compound selected from the group consisting of [4-(2-methylpropyl)amino-3-nitroquinolin-2-yl]trifluoromethanesulfonate, [4-(2-hydroxy-2-methylpropyl)amino-3-nitroquinolin-2-yl]trifluoromethanesu lfonate, [4-(2-methylpropyl)amino-3-nitroquinolin-2-yl]methanesulfonate, and [4-(2-hydroxy-2-methylpropyl)amino-3-nitroquinolin-2yl]methanesulfonat e.
A compound selected from the group consisting of N.sup.2,N.sup.2 -Bis(phenylmethyl)-N.sup.4 -(2-methylpropyl)-3-nitroquinoline-2,4-diamine and N.sup.2,N.sup.2 -bis(phenylmethyl)-N.sup.4 -(2-hydroxy-2-methylpropyl)-3-nitroquinoline-2,4-diamine.
A compound selected from the group consisting of N.sup.2,N.sup.2 -bis (phenylmethyl)-N.sup.4 -(2-methylpropyl )quinoline-2,3,4-triamine and N.sup.2,N.sup.2 -bis(phenylmethyl)-N.sup.4 -(2-hydroxy-2-methylpropyl)quinoline-2,3,4-triamine.
A compound selected from the group consisting of N,N-bis(phenylmethyl)-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine and N,N-bis(phenylmethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinol in-4-amine.
Dependencies are inferred from the claim text.