3-Fluoro-4-methoxybenzoyl chloride → N-[1-Cyano-1-methyl-2-(4,6,7-trichloro-2H-indazol-2-yl)ethyl]-3-fluoro-4-methoxybenzamide

HRID 1257038Notes

Reaction equation

HRID 1257038 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5](Cl)=[O:6].[NH2:13][C:14]([CH3:30])([CH2:17][N:18]1[CH:26]=[C:25]2[C:20]([C:21]([Cl:29])=[C:22]([Cl:28])[CH:23]=[C:24]2[Cl:27])=[N:19]1)[C:15]#[N:16]>C1COCC1>[C:15]([C:14]([NH:13][C:5](=[O:6])[C:4]1[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:2]([F:1])[CH:3]=1)([CH3:30])[CH2:17][N:18]1[CH:26]=[C:25]2[C:20]([C:21]([Cl:29])=[C:22]([Cl:28])[CH:23]=[C:24]2[Cl:27])=[N:19]1)#[N:16]

Participants

4

Reactant 2

HCID 27792553-Fluoro-4-methoxybenzoyl chlorideHCID 666208912-Amino-2-methyl-3-(4,6,7-trichloro-2H-indazol-2-yl)propionitrile

Product 1

HCID 68712117N-[1-Cyano-1-methyl-2-(4,6,7-trichloro-2H-indazol-2-yl)ethyl]-3-fluoro-4-methoxybenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Using a procedure similar to that described in Example 60, except using a solution of 3-fluoro-4-methoxybenzoyl chloride (0.16 mmole) in THF and a solution of 2-amino-2-methyl-3-(4,6,7-trichloro-2H-indazol-2-yl)propionitrile (0.075 mmole, described in Example 147) in THF mixed with TEA (3% v./v.), the title compound was isolated as solid residue (6.6 mg). It was dissolved in DMSO for further biological evaluation and analyzed by LCMS. MS (ES): M/Z [M+H]=455, RT=0.69 min.

Sources & evidence

ORD record
ord-22e8aca394b6423cbc0fc6b683fbe24f
Source dataset
uspto-grants-2013_06
Patent number
US08461176B2

Reaction notes

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