1-[2-(Trifluoromethyl)benzoyl]piperazine → 6-[4-(2-TRIFLUOROMETHYLBENZOYL)PIPERAZIN-1-YL]PYRIDAZINE-3-CARBOXYLIC Acid (2-CYCLOBUTYLETHYL)AMIDE

HRID 2056591Notes

Reaction equation

HRID 2056591 reaction equation
[CH:1]1([CH2:5][CH2:6][NH:7][C:8]([C:10]2[N:11]=[N:12][C:13](Cl)=[CH:14][CH:15]=2)=[O:9])[CH2:4][CH2:3][CH2:2]1.[N:17]1([C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]([F:34])([F:33])[F:32])=[O:24])[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1>>[CH:1]1([CH2:5][CH2:6][NH:7][C:8]([C:10]2[N:11]=[N:12][C:13]([N:20]3[CH2:21][CH2:22][N:17]([C:23](=[O:24])[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[C:31]([F:34])([F:32])[F:33])[CH2:18][CH2:19]3)=[CH:14][CH:15]=2)=[O:9])[CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 167337841-[2-(Trifluoromethyl)benzoyl]piperazineHCID 860260456-CHLOROPYRIDAZINE-3-CARBOXYLIC Acid (2-CYCLOBUTYLETHYL)AMIDE

Product 1

HCID 112133666-[4-(2-TRIFLUOROMETHYLBENZOYL)PIPERAZIN-1-YL]PYRIDAZINE-3-CARBOXYLIC Acid (2-CYCLOBUTYLETHYL)AMIDE

Procedure

Following the procedure of Example 15, making variations only as required to use 6-chloropyridazine-3-carboxylic acid (2-cyclobutylethyl)amide in place of 6-chloropyridazine-3-carboxylic acid (2-cyclopropyl-2-hydroxyethyl)amide to react with piperazin-1-yl-(2-trifluoromethylphenyl)methanone, the title compound was obtained as a white powder (47% yield). 1H NMR (300 MHz, CDCl3) δ 8.02, 7.74, 7.73, 7.57, 7.35, 6.98, 4.03, 3.89-3.66, 3.40-3.31, 2.36, 2.09-2.00, 1.92-1.57. 13C NMR (75 MHz, CDCl3) δ 167.6, 134.3, 132.4, 129.5, 127.2, 127.0, 126.9, 126.8, 126.7, 125.5, 121.8, 112.6, 46.4, 44.6, 44.5, 41.3, 37.6, 36.5, 33.7, 28.3, 18.6. MS (ES+) m/z 462.3 (M+1).

Sources & evidence

ORD record
ord-0b497403d2444b6486a252e030f3b556
Source dataset
uspto-grants-2008_02
Patent number
US07335658B2

Reaction notes

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