Azaadamantane formate ester and process for preparing azaadamantane derivatives
AssigneeAbbVie Inc.
InventorsAlbert Wayne KRUGER, Shuang CHEN, Steven Cramer CULLEN, James Joseph NAPIER
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Abstract
A compound, (4s)-1-azaadamantane-4yl formate ester, is described. In addition, a process is described for preparing (4s)-1-azaadamantane-4yl formate ester, aminothiadiazole-phenyl phosphate salt, bromothiadizole-phenyl or (4s)-4-(5-phenyl-1,3,4-thiadiazol-2-yloxy)-1-azatricyclo[3.3.1.13,7]-decane dihydrogen citrate. Furthermore, a process is described, comprising step of hydrolyzing (4s)-1-azaadamantane-4yl formate ester to form (4s)-1-azaadamantan-4-ol HBr salt.
Claims26
A process for preparing a compound, or salt of a compound, or solvate of a compound, of Formula (I)
- the process comprising step of:
- contacting (E)-N-benzylidene-1-(cyclohex-3-en-1-yl)methanamine with an aldehyde, or with an acetal, or with a hemiacetal, in presence of formic acid and a reaction medium.
A process for preparing a compound, or salt of a compound, or solvate of a compound, of Formula (II)
- the process comprising step of:
- contacting a compound of Formula (I)
- with a hydrolyzing agent in a reaction medium.
A process for preparing a compound, or salt of a compound, or solvate of a compound, of Formula (II)
- the process comprising:
- (a) contacting (E)-N-benzylidene-1-(cyclohex-3-en-1-yl)methanamine with an aldehyde, or with an acetal, or with a hemiacetal, in presence of formic acid and a reaction medium to form a compound of Formula (I)
- and
- (b) contacting a compound of Formula (I) with a hydrolyzing agent in a reaction medium.
A process for preparing a compound, or salt of a compound, or solvate of a compound, of Formula (II)
- the process comprising:
- (a) contacting (E)-N-(cyclohex-3-en-1-ylmethylene)-1-phenylmethanamine with an isomerizing agent to form (E)-N-benzylidene-1-(cyclohex-3-en-1-yl)methanamine;
- (b) contacting (E)-N-benzylidene-1-(cyclohex-3-en-1-yl)methanamine with an aldehyde, or with an acetal, or with a hemiacetal, in presence of formic acid and a reaction medium to form a compound of Formula (I)
- and
- (c) contacting a compound of Formula (I) with a hydrolyzing agent in a reaction medium.
A process for preparing a compound, or salt of a compound, or solvate of a compound, of Formula (II)
- the process comprising:
- (a) condensing benzylamine with cyclohex-3-enecarbaldehyde to form (E)-N-(cyclohex-3-en-1-ylmethylene)-1-phenylmethanamine;
- (b) contacting (E)-N-(cyclohex-3-en-1-ylmethylene)-1-phenylmethanamine with an isomerizing agent to form (E)-N-benzylidene-1-(cyclohex-3-en-1-yl)methanamine;
- (c) contacting (E)-N-benzylidene-1-(cyclohex-3-en-1-yl)methanamine with an aldehyde, or with an acetal, or with a hemiacetal, in presence of formic acid and a reaction medium to form a compound of Formula (I)
- and
- (d) contacting a compound of Formula (I) with a hydrolyzing agent in a reaction medium.
A compound, or a salt of a compound, or solvate of a compound, which is
A process comprising step of contacting (E)-N-(cyclohex-3-en-1-ylmethylene)-1-phenylmethanamine with an isomerizing agent present in an amount ranging from about 0.05 to 0.2 molar equivalents of the isomerizing agent to the (E)-N-(cyclohex-3-en-1-ylmethylene)-1-phenylmethanamine.
A process for preparing a 2-amino-5-phenyl-1,3,4-thiadiazole salt, the process comprising step of contacting aminothiourea and benzoic acid in presence of polyphosphoric acid.
A process for preparing 2-bromo-5-phenyl-1,3,4-thiadiazole, or salt or solvate thereof, the process comprising step of contacting a 2-amino-5-phenyl-1,3,4-thiadiazole salt, a Cu(II)halide and an alkyl-nitrite, in presence of a polar aprotic solvent.
A process for preparing 2-bromo-5-phenyl-1,3,4-thiadiazole, or salt or solvate thereof, the process comprising steps of:
- (a) contacting aminothiourea and benzoic acid in presence of polyphosphoric acid to form a 2-amino-5-phenyl-1,3,4-thiadiazole salt;
- and
- (b) contacting the 2-amino-5-phenyl-1,3,4-thiadiazole salt, a Cu(II)halide and an alkyl-nitrite, in presence of a polar aprotic solvent.
A process for preparing a compound, or a salt of a compound, or a solvate thereof, of Formula (III)
- the process comprising step of contacting a compound, or a salt of a compound, or a solvate of a compound, of Formula (II)
- with 2-bromo-5-phenyl-1,3,4-thiadiazole, in presence of a metal (alkylsilyl)amide and a reaction medium, to form a reaction mixture, and optionally contacting the reaction mixture with citric acid.
A process for preparing a compound, or a salt of a compound, or a solvate thereof, of Formula (III)
- the process comprising steps of:
- (a) condensing benzylamine with cyclohex-3-enecarbaldehyde to form (E)-N-(cyclohex-3-en-1-ylmethylene)-1-phenylmethanamine;
- (b) contacting (E)-N-(cyclohex-3-en-1-ylmethylene)-1-phenylmethanamine with an isomerizing agent to form (E)-N-benzylidene-1-(cyclohex-3-en-1-yl)methanamine;
- (c) contacting (E)-N-benzylidene-1-(cyclohex-3-en-1-yl)methanamine with an aldehyde, or with an acetal, or with a hemiacetal, in presence of formic acid and a reaction medium to form a compound of Formula (I)
- (d) contacting a compound of Formula (I) with a hydrolyzing agent in a reaction medium to form a compound, or a salt of a compound, of Formula (II)
- (e) contacting aminothiourea and benzoic acid in presence of polyphosphoric acid to form a 2-amino-5-phenyl-1,3,4-thiadiazole salt;
- (f) contacting a 2-amino-5-phenyl-1,3,4-thiadiazole salt, a Cu(II)halide and an alkyl-nitrite, in presence of a polar aprotic solvent to form 2-bromo-5-phenyl-1,3,4-thiadiazole;
- and
- (g) contacting a compound of Formula (II) with 2-bromo-5-phenyl-1,3,4-thiadiazole, in presence of a metal (alkylsilyl)amide and a reaction medium, to form a reaction mixture, and optionally contacting the reaction mixture with citric acid.
Dependencies are inferred from the claim text.