5-Fluoro-2-(trifluoromethyl)benzoyl chloride → 6-(4-(5-Fluoro-2-trifluoromethylbenzoyl)piperazin-1-yl)pyridazine-3-carboxylic acid (2-cyclopropylethyl)amide

HRID 2424468Notes

Reaction equation

HRID 2424468 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][NH:20][C:21]([C:23]2[N:24]=[N:25][C:26]([N:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)=[CH:27][CH:28]=2)=[O:22])[CH2:17][CH2:16]1>>[CH:15]1([CH2:18][CH2:19][NH:20][C:21]([C:23]2[N:24]=[N:25][C:26]([N:29]3[CH2:34][CH2:33][N:32]([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])[CH2:31][CH2:30]3)=[CH:27][CH:28]=2)=[O:22])[CH2:17][CH2:16]1

Participants

3

Reactant 2

HCID 27375605-Fluoro-2-(trifluoromethyl)benzoyl chlorideHCID 66849327N-(2-cyclopropylethyl)-6-(1-piperazinyl)-3-pyridazinecarboxamide

Product 1

HCID 160358766-(4-(5-Fluoro-2-trifluoromethylbenzoyl)piperazin-1-yl)pyridazine-3-carboxylic acid (2-cyclopropylethyl)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 (2-cyclopropylethyl)amide, the title compound was obtained as a white powder (65% yield). 1H NMR (400 MHz, CDCl3) δ 8.05, 7.98, 7.74, 7.27-7.24, 7.09-7.06, 7.00, 4.08-3.96, 3.94-3.68, 3.55, 3.36, 1.50, 0.79-0.69, 0.48-0.42, 0.11-0.09.

Sources & evidence

ORD record
ord-4515e28cb96d449eb8f720fbbfaa68ee
Source dataset
uspto-grants-2011_06
Patent number
US07964591B2

Reaction notes

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