Benzoyl chloride, 3-bromo- → 3-Bromo-N-[1-cyano-1-methyl-2-(4,6,7-trichloro-2H-indazol-2-yl)ethyl]benzamide

HRID 1257041Notes

Reaction equation

HRID 1257041 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].[NH2:11][C:12]([CH3:28])([CH2:15][N:16]1[CH:24]=[C:23]2[C:18]([C:19]([Cl:27])=[C:20]([Cl:26])[CH:21]=[C:22]2[Cl:25])=[N:17]1)[C:13]#[N:14]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH:11][C:12]([C:13]#[N:14])([CH3:28])[CH2:15][N:16]1[CH:24]=[C:23]2[C:18]([C:19]([Cl:27])=[C:20]([Cl:26])[CH:21]=[C:22]2[Cl:25])=[N:17]1)=[O:6]

Participants

4

Reactant 2

HCID 74377Benzoyl chloride, 3-bromo-HCID 666208912-Amino-2-methyl-3-(4,6,7-trichloro-2H-indazol-2-yl)propionitrile

Product 1

HCID 687102423-Bromo-N-[1-cyano-1-methyl-2-(4,6,7-trichloro-2H-indazol-2-yl)ethyl]benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Using a procedure similar to that described in Example 60, except using a solution of 3-bromobenzoyl 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]=485, RT=0.75 min.

Sources & evidence

ORD record
ord-a6be7f7d8b1a43d9b8adb8601c35383a
Source dataset
uspto-grants-2013_06
Patent number
US08461176B2

Reaction notes

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