Production method of isoxazoline-substituted benzoic acid amide compound
A production method of an isoxazoline-substituted benzoic acid amide compound of Formula (1) where X is a halogen atom, C 1-6 haloalkyl, etc., Y is a halogen atom, C 1-6 alkyl, etc., R 1 is a C 1-6 haloalkyl, etc., R 2 and R 3 independently of each other are a hydrogen atom, C 1-6 alkyl, etc., R 4 is C 1-6 alkyl, C 1-6 haloalkyl, etc., R 5 is a hydrogen atom, c 1-6 alkyl, etc., m is an integer of 0 to 5, n is an integer of 0 to 4, including: reacting an isoxazoline-substituted benzene compound of Formula (3) where X, Y, R 1 , m, and n are the same as defined above, L is a chlorine atom, a bromine atom, —C(O)OH, —C(O)J, etc., J is a halogen atom, with a 2-aminoacetic acid amide compound of Formula (2) where R 2 , R 3 , R 4 , and R 5 are the same as defined above, or a salt thereof; crystal forms and the production method thereof.
1. A process of preparing an isoxazoline-substituted benzoic acid amide compound of Formula (1):
[where X is a halogen atom, cyano, nitro, —SF 5 , C 1-6 alkyl, C 1-6 haloalkyl, hydroxy(C 1-6 )alkyl, hydroxy(C 1-6 )haloalkyl, C 1-6 alkoxy(C 1-6 )alkyl, C 1-6 haloalkoxy (C 1-6 ) alkyl, C 1-6 alkoxy(C 1-6 )haloalkyl, C 1-6 haloalkoxy(C 1-6 )haloalkyl, C 3-8 cycloalkyl, C 3-8 halocycloalkyl, —OR 6 , —OSO 2 R 6 , —S(O),R 6 , or —N(R 8 )R 7 , where when m is 2 or more, Xs are optionally the same as or different from each other,
Y is a halogen atom, cyano, nitro, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, C 1-6 alkylthio, C 1-6 haloalkylthio, C 1-6 alkylsulfonyl, C 1-6 haloalkylsulfonyl, or —N(R 8 )R 7 , where when n is 2 or more, Ys are optionally the same as or different from each other,
R 1 is a hydrogen atom, C 1-6 alkyl, C 1-6 haloalkyl, C 3-8 cycloalkyl, or C 3-8 halocycloalkyl,
R 2 is a hydrogen atom, cyano, C 1-6 alkyl, or C 1-6 haloalkyl,
R 3 is a hydrogen atom or C 1-6 alkyl, or R 3 together with R 2 optionally form a C 2-5 alkylene chain to form together with a carbon atom to which R 3 is bonded a 3- to 6-membered ring, and at this time, the alkylene chain optionally contains one oxygen atom, one sulfur atom, or one nitrogen atom,
R 4 is a hydrogen atom, C 1-6 alkyl, C 1-6 alkyl optionally substituted with R 11 , C 1-6 haloalkyl, C 3-8 cycloalkyl, C 3-8 halocycloalkyl, C 3-6 alkenyl, C 3-6 haloalkenyl, C 3-6 alkynyl, phenyl, or phenyl substituted with (Z) t ,
R 5 is a hydrogen atom, C 1-6 alkyl, C 1-6 haloalkyl, C 3-8 cycloalkyl, C 3-8 halocycloalkyl, —CHO, C 1-6 alkylcarbonyl, C 1-6 haloalkylcarbonyl, C 1-6 alkoxycarbonyl, C 1-6 alkylsulfonyl, or C 1-6 haloalkylsulfonyl, or R 5 together with R 4 optionally form a C 2-6 alkylene chain to form together with a nitrogen atom to which R 5 is bonded a 3- to 7-membered ring, and at this time, the alkylene chain optionally contains one oxygen atom, one sulfur atom, or one nitrogen atom and is optionally substituted with a halogen atom, a C 1-6 alkyl group, a C 1-6 alkoxy group, a formyl group, a C 1-6 alkylcarbonyl group, a C 1-6 alkoxycarbonyl group, an oxo group, or a thioxo group,
R 6 is C 1-6 alkyl, C 1-4 alkoxy(C 1-4 )alkyl, C 1-6 haloalkyl, or C 1-4 haloalkoxy(C 1-4 ) haloalkyl,
R 7 is C 1-6 alkyl, —CHO, C 1-6 alkylcarbonyl, C 1-6 haloalkylcarbonyl, C 1-6 alkoxycarbonyl, C 1-6 alkylsulfonyl, or C 1-6 haloalkylsulfonyl,
R 8 is a hydrogen atom or C 1-6 alkyl,
R 11 is cyano, C 3-8 cycloalkyl, C 3-8 halocycloalkyl, —OR 6 , —S(O),R 6 , —N(R 8 )R 7 , phenyl, or phenyl substituted with (Z) 1 ,
Z is a halogen atom, cyano, nitro, C 1-6 alkyl, C 1-6 haloalkyl, C 3-8 cycloalkyl, C 3-8 halocycloalkyl, —OR 6 , —OSO 2 R 6 , —S(O) r R 6 , or —N(R 8 )R 7 , where when t is 2 or more, Zs are optionally the same as or different from each other,
m is an integer of 0 to 5,
n is an integer of 0 to 4,
r is an integer of 0 to 2, and
t is an integer of 1 to 5],
the production method comprising: reacting an isoxazoline-substituted benzene compound of Formula (3):
[where X, Y, R 1 , m, and n are the same as defined above,
L is a chlorine atom, a bromine atom, an iodine atom, —OSO 2 R 9 , —C(O)OH, —C(O)OR 10 , or —C(O)J,
R 9 is C 1-6 alkyl, C 1-6 haloalkyl, phenyl, or phenyl substituted with (Z) t ,
R 10 is C 1-6 alkyl, C 1-4 alkoxy(C 1-4 )alkyl, C 1-6 haloalkyl, C 1-4 haloalkoxy(C 1-4 ) haloalkyl, benzyl, phenyl, or phenyl substituted with (Z) t ,
Z, r and t are the same as defined above, and
J is a halogen atom],
with a 2-aminoacetic acid amide compound of Formula (2):
[where R 2 , R 3 , R 4 , and R 5 are the same as defined above] or a salt thereof.
2. The process of preparing an isoxazoline-substituted benzoic acid amide compound according to claim 1 , wherein a compound of Formula (3) (where L is a chlorine atom, a bromine atom, an iodine atom, or —OSO 2 R 9 ) is reacted with a compound of Formula (2) in the presence of carbon monoxide and a palladium catalyst.
3. The process of preparing an isoxazoline-substituted benzoic acid amide compound according to claim 1 , wherein a compound of Formula (3) (where L is —C(O)OH) is reacted with a compound of Formula (2) in the presence of a condensing agent.
4. The process of preparing an isoxazoline-substituted benzoic acid amide compound according to claim 1 , wherein a compound of Formula (3) (where L is —C(O)OR 10 or —C(O)J) is reacted with a compound of Formula (2) in the presence of a base.
5. The process of preparing a compound of Formula (1-1):
according to claim 1 .
6. The process of preparing a compound of Formula (1-1):
according to claim 2 .
7. The process of preparing a compound of Formula (1-1):
according to claim 3 .
8. The process of preparing a compound of Formula (1-1):
according to claim 4 .