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US 2004/0106803 A1Published application
Production method of 1-substituted-1,2,3-triazole derivatives
OwnerTomomi Ikemoto, Tatsuya Ito +4inventors
InventorsTomomi Ikemoto, Tatsuya Ito, Kiminori Tomimatsu, Yasuhiro Sawai, Hirohiko Nishiyama, Yasushi Isogami
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Abstract
A method for producing a compound of the formula: 1 by reacting 2 (1) in a secondary or tertiary alcohol in the presence of a base, or (2) in the absence of a base is provided. According to this method, a 1-substituted-1,2,3-triazole compound having a tyrosine kinase inhibitory action can be produced efficiently in a high yield at an industrial large scale by a convenient method
Claims48
A method for producing a compound of the formula:
- 112
- wherein
- Ra1 and Ra2 are each a hydrogen atom, a substituted hydroxy, a substituted thiol, a substituted amino, an optionally substituted hydrocarbon group, an optionally substituted heterocyclic group or an acyl;
- Ra3 is a group of the formula:
- 113
- wherein Ra4 and Ra5 are each a hydrogen atom, an optionally substituted hydroxy, an optionally substituted thiol, an optionally substituted amino, an optionally substituted hydrocarbon group, an optionally substituted heterocyclic group or an acyl, or Ra4 and Ra5 in combination form oxo,
- Ra6 is an optionally substituted aromatic group, and
- ma is an integer of 0 to 10;
- or p1 two or three from Ra1, Ra2 and Ra3 form an optionally substituted ring, together with the adjacent carbon atom;
- and
- Ra7 and Ra8 are each a hydrogen atom, a halogen, an optionally substituted hydroxy, an optionally substituted thiol, an optionally substituted amino, an optionally substituted hydrocarbon group, an optionally substituted heterocyclic group or an acyl,
- which method comprises reacting a compound of the formula:
- 114
- wherein Xa is a leaving group and other symbols are as defined above, or a salt thereof, and a compound of the formula:
- 115
- wherein each symbol is as defined above, or a salt thereof,
- (1) in a secondary or tertiary alcohol in the presence of a base, or
- (2) in the absence of a base.
15 more elements
The production method of cliam 1, wherein Ra1 and Ra2 are each a hydrogen atom.
A salt of a compound of the formula:
- 117
A compound of the formula:
- 118
- wherein Xa′ is a halogen atom, OSO2Ra or OCORa wherein Ra is an optionally substituted hydrocarbon group.
A method for producing a compound of the formula:
- 119
- wherein Xa′ is a halogen atom, OSO2Ra or OCORa wherein Ra is an optionally substituted hydrocarbon group, which comprises reacting a compound of the formula:
- 120
- wherein Ma is a hydrogen atom, an alkali metal atom or an alkaline earth metal atom, and 1) thionyl halide, 2) oxalyl halide, 3) a compound of the formula:
- RaSO2Xa or (RaSO2)2O
- wherein Ra is as defined above and Xa is a leaving group, or 4) a compound of the formula:
- RaCOXa or (RaCO)2O
- wherein Ra and Xa are as defined above, under basic conditions.
5 more elements
A compound of the formula:
- 121
- or a salt thereof.
A method for producing a compound of the formula:
- 122
- which comprises reacting a compound of the formula:
- 123
- wherein Ma is a hydrogen atom, an alkaline metal atom or an alkaline earth metal atom, and 1) thionyl halide, 2) oxalyl halide, 3) a compound of the formula:
- RaSO2Xa or (RaSO2)2O
- wherein Ra is an optionally substituted hydrocarbon group and Xa is a leaving group or 4) a compound of the formula:
- RaCOXa or (RaCO)2O
- wherein Ra and Xa are as defined above, under basic conditions to give a compound of the formula:
- 124
- wherein Xa′ is a halogen atom, OSO2Ra or OCORa wherein Ra is as defined above, and reacting this compound with a compound of the formula:
- 125
- or a salt thereof, (1) in the presence of a base in a secondary or tertiary alcohol, or
- (2) in the absence of a base to give a compound of the formula:
- 126
- and deprotecting this compound.
12 more elements
A method for producing a compound of the formula:
- 127
- which comprises deprotecting a compound of the formula:
- 128
A method for producing a compound of the formula:
- 129
- which comprises deprotecting a compound of the formula:
- 130
A method for producing a compound of the formula:
- 131
- wherein Rb1, Rb2 and Rb3 are each a hydrogen atom, an optionally substituted hydroxy, an optionally substituted thiol, an optionally substituted amino, an optionally substituted hydrocarbon group, an optionally substituted heterocyclic group or an acyl, or two or three from Rb1, Rb2 and Rb3 form, together with the adjacent carbon atom, an optionally substituted ring, and Rb4 and Rb5 are each a hydrogen atom, an optionally substituted hydroxy, an optionally substituted thiol, an optionally substituted amino, an optionally substituted hydrocarbon group, an optionally substituted heterocyclic group or an acyl, and Rb6 is an optionally substituted alkyl or an optionally substituted phenyl, or a salt thereof, which comprises reacting a compound of the formula:
- 132
- wherein each symbol is as defined above, or a salt thereof and a compound of the formula:
- 133
- wherein Xb1 and Xb2 are each a halogen, and Rb4, Rb5 and Rb6 are as defined above, or a salt thereof, and treating the reaction mixture with a base.
3 more elements
A method for producing a compound of the formula:
- 135
- wherein, Rb10 is an optionally substituted amino, an optionally substituted hydrocarbon group, an optionally substituted heterocyclic group or an acyl, Rb11 is a substituent, nb is an integer of 0 to 4, and Rb12 is an optionally substituted alkylene, an optionally substituted alkenylene or an optionally substituted alkynylene, or a salt thereof, which comprises reacting a compound of the formula:
- 136
- wherein each symbol is as defined above, or a salt thereof and a compound of the formula:
- HOOC—Rb12—NH2
- wherein Rb12 is as defined above, a salt thereof or a reactive derivative thereof.
3 more elements
A method for producing a compound of the formula:
- 146
- wherein Arc is an optionally substituted aromatic group, Rc1 and Rc2 are each a hydrogen atom or a lower alkyl, Rc3 and Rc4 are each a hydrogen atom or a lower alkyl, Yc is C, S or SO and Rc5 is a hydrogen atom, a lower alkyl, an optionally substituted phenyl, an optionally substituted benzyloxy or an optionally substituted benzylamino, or a salt thereof, which comprises reacting a reaction mixture of a compound of the formula:
- 147
- wherein each symbol is as defined above, or a salt thereof and a compound of the formula:
- 148
- wherein Xc1 and Xc2 are each a halogen, and other symbols are as defined above, or a salt thereof, with a compound of the formula:
- 149
- wherein Mc is a hydrogen atom or a metal, and other symbols are as defined above, or a salt thereof.
5 more elements
A compound of the formula:
- 169
1-[4-[4-[[2-[(E)-2-[4-(Trifluoromethyl)phenyl]ethenyl]-1,3-oxazol-4-yl]methoxy]phenyl]butyl]-1H-1,2,3-triazole.
Dependencies are inferred from the claim text.