(5-Fluoro-2-trifluoromethylphenyl)piperazin-1-ylmethanone → 6-[4-(5-FLUORO-2-TRIFLUOROMETHYLBENZOYL)PIPERAZIN-1-YL]PYRIDAZINE-3-CARBOXYLIC Acid (2-HYDROXY-3,3-DIMETHYLBUTYL)AMIDE

HRID 2354792Notes

Reaction equation

HRID 2354792 reaction equation
[OH:1][CH:2]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:3][NH:4][C:5]([C:7]1[N:8]=[N:9][C:10](Cl)=[CH:11][CH:12]=1)=[O:6].[N:18]1([C:24]([C:26]2[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=2[C:33]([F:36])([F:35])[F:34])=[O:25])[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1>>[OH:1][CH:2]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:3][NH:4][C:5]([C:7]1[N:8]=[N:9][C:10]([N:21]2[CH2:22][CH2:23][N:18]([C:24](=[O:25])[C:26]3[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=3[C:33]([F:36])([F:35])[F:34])[CH2:19][CH2:20]2)=[CH:11][CH:12]=1)=[O:6]

Participants

3

Reactant 2

HCID 57875818(5-Fluoro-2-trifluoromethylphenyl)piperazin-1-ylmethanoneHCID 86025983HCID 86025983, compound

Product 1

HCID 670916946-[4-(5-FLUORO-2-TRIFLUOROMETHYLBENZOYL)PIPERAZIN-1-YL]PYRIDAZINE-3-CARBOXYLIC Acid (2-HYDROXY-3,3-DIMETHYLBUTYL)AMIDE

Procedure

Following the procedure of Example 15, making variations only as required to use 6-chloropyridazine-3-carboxylic acid (2-hydroxy-3,3-dimethylbutyl)amide in place of 6-chloropyridazine-3-carboxylic acid (2-cyclopropyl-2-hydroxyethyl)amide to react with piperazin-1-yl-(5-fluoro-2-trifluoromethylphenyl)methanone, the title compound was obtained as a brown solid (51% yield). m.p. 186-189° C. 1H NMR (300 MHz, CDCl3) δ 8.20, 8.04, 7.75, 7.22, 7.07, 6.98, 4.06-3.98, 3.91-3.71, 3.47-3.23, 2.45, 0.96. 13C NMR (75 MHz, CDCl3) δ 166.3, 164.1, 160.1, 160.0, 130.1, 127.2, 116.9, 116.6, 115.0, 114.7, 112.4, 79.4, 46.4, 44.5, 44.3, 41.9, 41.3, 34.4, 25.7. MS (ES+) m/z 498 (M+1).

Sources & evidence

ORD record
ord-75bdd17dd3a94c7fa2247e2caef1d671
Source dataset
uspto-grants-2010_07
Patent number
US07754711B2

Reaction notes

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