Method for producing pyrrole-imidazole (poly)amide

A method for producing a pyrrole-imidazole (poly)amide, comprising the steps of reacting a compound represented by the following formula (1):

• wherein in the formula (1),
• Ra is a (poly)amide organic group having 1 or more and 3 or less kinds of a unit selected from the units represented by the formulas (2a), (2b), and (2c) as a constituent unit, wherein a total number of the constituent unit is 1 or more and 30 or less,
• Q1 is a carrier, or an amino group optionally having a hydroxy group, an organic group, or a substituent,
• wherein the carrier is either a solid-phase carrier or a soluble carrier, the solid-phase carrier is a resin solid-phase carrier, and the soluble carrier is at least one selected from the group consisting of 3,4,5-tri(n-octadecyloxy)benzyl alcohol, 3,5-di(docosyloxy)benzyl alcohol, 2,4-di(docosyloxy)benzyl alcohol, and 2-[12-(docosyloxy) dodecyloxy]-9-(3-fluorophenyl)-9-bromofluorene,
• and wherein the organic group is a C1-12 alkoxy group optionally having a substituent, a C2-12 alkenyloxy group optionally having a substituent, a C6-12 aryloxy group optionally having a substituent, or a C7-12 aralkyloxy group optionally having a substituent,
• m is 0 or 1,
• R1 to R3 independently represent a C1-12 alkyl group,
• when the compound represented by the formula (1) has a plurality of units represented by the formula (2a), a plurality of R2 may be the same as or different from each other,
• when the compound represented by the formula (1) has a plurality of units represented by the formula (2b), a plurality of R3 may be the same as or different from each other,
• Rb represents a C1-10 alkylene group wherein the alkylene group may be bonded with one or more groups selected from an amino group having a substituent, a C1-12 alkoxy group optionally having a substituent, a C2-12 alkenyloxy group optionally having a substituent, a C6-12 aryloxy group optionally having a substituent, and a C7-12 aralkyloxy group optionally having a substituent,
• when the compound represented by the formula (1) has a plurality of units represented by the formula (2c), a plurality of Rb may be the same as or different from each other,
• wherein the substituent that may be present in the C1-12 alkoxy group, C2-12 alkenyloxy group, C6-12 aryloxy group, and C7-12 aralkyloxy group is a nitro group, a nitrile group, or a halogen atom,
• and wherein the substituent that may be present in the amino group is a C1-12 alkyl group, a C2-12 alkenyl group, a C7-12 aralkyl group, or a C6-12 aryl group, wherein the alkyl group, alkenyl group, aralkyl group, and aryl group may optionally have a C1-12 alkylamino group bonded thereto,
• represents a bond,
• with a compound represented by the following formula (3):
• wherein in the formula (3),
• Rc is a (poly)amide organic group having 1 or more and 3 or less kinds of the unit selected from the units represented by the formulas (4a), (4b), and (4c) as a constituent unit and the total number of the constituent unit is 1 or more and 30 or less,
• Q2 is a protective group of an amino group, or a group represented by the formulas (5a), (5b), (5c) or (5d),
• E is a leaving group,
• n is 0 or 1,
• R4 to R8 each independently represents a C1-12 alkyl group,
• when the compound represented by the formula (3) has a plurality of units represented by the formula (4a), a plurality of R5 may be the same as or different from each other,
• when a compound represented by the formula (3) has a plurality of units represented by the formula (4b), a plurality of R6 may be the same as or different from each other,
• Rd represents a C1-10 alkylene group wherein the alkylene group may be bonded with one or more groups selected from an amino group having a substituent, a C1-12 alkoxy group optionally having a substituent, a C2-12 alkenyloxy group optionally having a substituent, and a C6-12 aryloxy group optionally having a substituent, and a C7-12 aralkyloxy group optionally having a substituent,
• when a compound represented by the formula (3) has a plurality of units represented by the formula (4c), a plurality of Rd may be the same as or different from each other,
• Re represents a C1-10 alkyl group wherein the alkyl group may be bonded with one or more groups selected from an amino group having a substituent, a C1-12 alkoxy group optionally having a substituent, a C2-12 alkenyloxy group optionally having a substituent, a C6-12 aryloxy group optionally having a substituent, and a C7-12 aralkyloxy group optionally having a substituent,
• wherein the substituent that may be present in the C1-12 alkoxy group, C2-12 alkenyloxy group, C6-12 aryloxy group, and C7-12 aralkyloxy group is a nitro group, a nitrile group, or a halogen atom,
• and wherein the substituent that may be present in the amino group is a C1-12 alkyl group, a C2-12 alkenyl group, a C7-12 aralkyl group, or a C6-12 aryl group, wherein the alkyl group, alkenyl group, aralkyl group, and aryl group may optionally have a C1-12 alkylamino group bonded thereto,
• represents a bond,
• in the presence of a heterocyclic aromatic compound as a solvent to produce the pyrrole-imidazole (poly)amide represented by the following formula (6):
• wherein in the formula (6), Ra, Rc, Q1, Q2, R1, R4, m and n are the same as described above,
• wherein the reaction between the compound represented by the formula (1) and the compound represented by the formula (3) is carried out in the presence of a tertiary amine.