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

HRID 1257036Notes

Reaction equation

HRID 1257036 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[CH:28]=[C:27]2[C:22]([C:23]([Cl:31])=[C:24]([Cl:30])[CH:25]=[C:26]2[Cl:29])=[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[CH:28]=[C:27]2[C:22]([C:23]([Cl:31])=[C:24]([Cl:30])[CH:25]=[C:26]2[Cl:29])=[N:21]1)#[N:18]

Participants

4

Reactant 2

HCID 27347093-Fluoro-4-(trifluoromethyl)benzoyl chlorideHCID 666208912-Amino-2-methyl-3-(4,6,7-trichloro-2H-indazol-2-yl)propionitrile

Product 1

HCID 86641830N-[1-Cyano-1-methyl-2-(4,6,7-trichloro-2H-indazol-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-(4,6,7-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 (13.9 mg). It was dissolved in DMSO for further biological evaluation and analyzed by LCMS. MS (ES): M/Z [M+H]=493, RT=0.76 min.

Sources & evidence

ORD record
ord-adcdb90e92c84c40bcc20472b22e7d08
Source dataset
uspto-grants-2013_06
Patent number
US08461176B2

Reaction notes

Loading…