4-(2-(6-substituted-hexylidene) hydrazinyl)benzonitrile and preparation thereof

A compound selected from:

• (Z)-4-(2-(6-iodohexylidene)hydrazinyl)benzonitrile,
• (Z)-4-(2-(6-bromohexylidene)hydrazinyl)benzonitrile,
• (Z)-4-(2-(6-chlorohexylidene)hydrazinyl)benzonitrile,
• (E)-4-(2-(6-iodohexylidene)hydrazinyl)benzonitrile,
• (E)-4-(2-(6-bromohexylidene)hydrazinyl)benzonitrile,
• (E)-4-(2-(6-chlorohexylidene)hydrazinyl)benzonitrile,
• a pharmaceutically acceptable salt of the compound, a geometric isomer of the compound, or a pharmaceutically acceptable salt of the geometric isomer.

A process for preparing a compound of Formula (I-B):

• a pharmaceutically acceptable salt of the compound, a geometric isomer of the compound, or a pharmaceutically acceptable salt of the geometric isomer, the process comprising reacting a compound of Formula (II)
• with a compound of Formula (HI):
• or a pharmaceutically acceptable salt thereof;
• wherein:
• R1 is a leaving group selected from halo, cyano, azido, —ORa, —OCORa, —OCOORa, —OCONRaRb, —NH3+, —NHRaRb+, —NRaRb, —OSO2Ra, and —OP(O)(ORa)2;
• Ra and Rb are each independently selected from H, optionally substituted C1-C10 alkyl, optionally substituted C2-C10 alkenyl, optionally substituted C2-C10 alkynyl, optionally substituted C1-C10 haloalkyl, optionally substituted 5 to 14 membered heteroaryl, and optionally substituted 6 to 14 membered aryl;
• R2a, R2b, R3a, R3b, R4a, R4b, R5a, R5b, R6a, and R6b are each independently selected from H, halo, C1-C6 alkyl, C1-C6 haloalkyl and —ORa;
• and
• R7a, R7b, R8a, R8b, R9a, R9b and R10 are each independently selected from H, halo, cyano, C1-C6 alkyl, C1-C6 haloalkyl and —ORa.

A process for preparing a compound of Formula (VI):

• a pharmaceutically acceptable salt of the compound, an isomer of the compound, or a pharmaceutically acceptable salt of the isomer;
• the process comprising:
• contacting a compound of Formula (I′)
• with an acid, to form a compound of Formula (IV)
• wherein:
• R1 is a leaving group selected from halo, cyano, azido, —ORa, —OCORa, —OCOORa, —OCONRaRb, —NH3+, —NHRaRb+, —NRaRb, —OSO2Ra, and —OP(O)(ORa)2;
• and
• Ra and Rb are each independently selected from H, optionally substituted C1-C10 alkyl, optionally substituted C2-C10 alkenyl, optionally substituted C2-C10 alkynyl, optionally substituted C1-C10 haloalkyl, optionally substituted 5 to 14 membered heteroaryl, and optionally substituted 6 to 14 membered aryl.

A compound of Formula (VI) or a pharmaceutically acceptable salt thereof prepared by a process comprising:

• contacting a compound of Formula (I′)
• with an acid, to form a compound of Formula (IV)
• reacting the compound of Formula (IV) with a compound of Formula (V)
• wherein:
• R1 is a leaving group selected from halo, cyano, azido, —ORa, —OCORa, —OCOORa, —OCONRaRb, —NH3+, —NHRaRb+, —NRaRb, —OSO2Ra, and —OP(O)(ORa)2;
• and
• Ra and Rb are each independently selected from H, optionally substituted C1-C10 alkyl, optionally substituted C2-C10 alkenyl, optionally substituted C2-C10 alkynyl, optionally substituted C1-C10 haloalkyl, optionally substituted 5 to 14 membered heteroaryl, and optionally substituted 6 to 14 membered aryl, thereby preparing the compound of Formula (VI) or a pharmaceutically acceptable salt thereof, wherein the compound of Formula (VI) is present together with the compound of Formula (I′) at an amount less than 1.5 micrograms/day.