5-Fluoro-2-(trifluoromethyl)benzoyl chloride → 6-[4-(5-Fluoro-2-trifluoromethylbenzoyl)piperazin-1-YL]pyridazine-3-carboxylic acid (3-cyclopropylpropyl)amide

HRID 2424474Notes

Reaction equation

HRID 2424474 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:11]([F:14])([F:13])[F:12])=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].[CH:15]1([CH2:18][CH2:19][CH2:20][NH:21][C:22]([C:24]2[N:25]=[N:26][C:27]([N:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)=[CH:28][CH:29]=2)=[O:23])[CH2:17][CH2:16]1>>[CH:15]1([CH2:18][CH2:19][CH2:20][NH:21][C:22]([C:24]2[N:25]=[N:26][C:27]([N:30]3[CH2:31][CH2:32][N:33]([C:7](=[O:8])[C:6]4[CH:10]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=4[C:11]([F:14])([F:13])[F:12])[CH2:34][CH2:35]3)=[CH:28][CH:29]=2)=[O:23])[CH2:17][CH2:16]1

Participants

3

Reactant 2

HCID 27375605-Fluoro-2-(trifluoromethyl)benzoyl chlorideHCID 668493796-Piperazin-1-yl-pyridazine-3-carboxylic acid (3-cyclopropylpropyl)amide

Product 1

HCID 113175806-[4-(5-Fluoro-2-trifluoromethylbenzoyl)piperazin-1-YL]pyridazine-3-carboxylic acid (3-cyclopropylpropyl)amide

Procedure

Following the procedure of Example 3, making variations only as required to use 5-Fluoro-2-trifluoromethylbenzoyl chloride in place of isoxazole-5-carbonyl chloride to react with 6-piperazin-1-yl-pyridazine-3-carboxylic acid (3-cyclopropylpropyl)amide, the title compound was obtained as a white powder (28% yield). 1H NMR (400 MHz, CDCl3) δ 8.07, 7.89, 7.76, 7.28-7.24, 7.10-7.08, 7.02, 4.06-4.03, 3.90-3.86, 3.82-3.72, 3.51, 3.37, 1.76-1.70, 1.30, 0.70-0.67, 0.44-0.40, 0.03-0.003.

Sources & evidence

ORD record
ord-b4e43aadb09b4ef781c4cdb8fef5a4df
Source dataset
uspto-grants-2011_06
Patent number
US07964591B2

Reaction notes

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