3-Fluoro-4-(trifluoromethyl)benzoyl chloride → N-[1-Cyano-1-methyl-2-(4,5,7-trichloro-2H-benzotriazol-2-yl)-ethyl]-3-fluoro-4-trifluoromethylbenzamide

HRID 1256994Notes

Reaction equation

HRID 1256994 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([F:14])([F:13])[F:12])[C:5](Cl)=[O:6].[NH2:15][C:16]([CH3:32])([CH2:19][N:20]1[N:24]=[C:23]2[C:25]([Cl:31])=[CH:26][C:27]([Cl:30])=[C:28]([Cl:29])[C:22]2=[N:21]1)[C:17]#[N:18]>C1COCC1>[C:17]([C:16]([NH:15][C:5](=[O:6])[C:4]1[CH:8]=[CH:9][C:10]([C:11]([F:14])([F:13])[F:12])=[C:2]([F:1])[CH:3]=1)([CH3:32])[CH2:19][N:20]1[N:24]=[C:23]2[C:25]([Cl:31])=[CH:26][C:27]([Cl:30])=[C:28]([Cl:29])[C:22]2=[N:21]1)#[N:18]

Participants

4

Reactant 2

HCID 27347093-Fluoro-4-(trifluoromethyl)benzoyl chlorideHCID 666199812-Amino-2-methyl-3-(4,5,7-trichloro-2H-benzotriazol-2-yl)-propionitrile

Product 1

HCID 86641826N-[1-Cyano-1-methyl-2-(4,5,7-trichloro-2H-benzotriazol-2-yl)-ethyl]-3-fluoro-4-trifluoromethylbenzamide

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-trifluoromethylbenzoyl chloride (0.16 mmole) in THF and a solution of 2-amino-2-methyl-3-(4,5,7-trichloro-2H-benzotriazol-2-yl)-propionitrile (0.075 mmole, described in Example 39) in THF mixed with TEA (3% v./v.), the title compound was isolated as solid residue (13.9 mg). It was dissolved in DMSO for further biological evaluation and analyzed by LCMS. MS (ES): M/Z [M+H]=494, RT=0.73 min.

Sources & evidence

ORD record
ord-6f41b21f3b7346769961c391d5830788
Source dataset
uspto-grants-2013_06
Patent number
US08461176B2

Reaction notes

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