2,4-Difluorobenzoyl chloride → N-[1-Cyano-1-methyl-2-(4,6,7-trichloro-2H-indazol-2-yl)ethyl]-2,4-difluorobenzamide

HRID 1257040Notes

Reaction equation

HRID 1257040 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[NH2:12][C:13]([CH3:29])([CH2:16][N:17]1[CH:25]=[C:24]2[C:19]([C:20]([Cl:28])=[C:21]([Cl:27])[CH:22]=[C:23]2[Cl:26])=[N:18]1)[C:14]#[N:15]>C1COCC1>[C:14]([C:13]([NH:12][C:4](=[O:5])[C:3]1[CH:7]=[CH:8][C:9]([F:11])=[CH:10][C:2]=1[F:1])([CH3:29])[CH2:16][N:17]1[CH:25]=[C:24]2[C:19]([C:20]([Cl:28])=[C:21]([Cl:27])[CH:22]=[C:23]2[Cl:26])=[N:18]1)#[N:15]

Participants

4

Reactant 2

HCID 5880812,4-Difluorobenzoyl chlorideHCID 666208912-Amino-2-methyl-3-(4,6,7-trichloro-2H-indazol-2-yl)propionitrile

Product 1

HCID 68710867N-[1-Cyano-1-methyl-2-(4,6,7-trichloro-2H-indazol-2-yl)ethyl]-2,4-difluorobenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Using a procedure similar to that described in Example 60, except using a solution of 2,4-difluorobenzoyl 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]=443, RT=0.71 min.

Sources & evidence

ORD record
ord-5ce4adfa60a444c7a2790e6a9857e0ec
Source dataset
uspto-grants-2013_06
Patent number
US08461176B2

Reaction notes

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