(2-(trifluoromethyl)phenyl)acetic acid → 6-{4-[2-(2-TRIFLUOROMETHYLPHENYL)ACETYL]PIPERAZIN-1-YL}PYRIDAZINE-3-CARBOXYLIC Acid (2-CYCLOPROPYLETHYL)AMIDE

HRID 2354734Notes

Reaction equation

HRID 2354734 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([OH:12])=O.[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:10](=[O:12])[CH2:9][C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=4[C:2]([F:1])([F:14])[F:13])[CH2:31][CH2:30]3)=[CH:27][CH:28]=2)=[O:22])[CH2:17][CH2:16]1

Participants

3

Reactant 2

HCID 594597(2-(trifluoromethyl)phenyl)acetic acidHCID 66849327N-(2-cyclopropylethyl)-6-(1-piperazinyl)-3-pyridazinecarboxamide

Product 1

HCID 116698046-{4-[2-(2-TRIFLUOROMETHYLPHENYL)ACETYL]PIPERAZIN-1-YL}PYRIDAZINE-3-CARBOXYLIC Acid (2-CYCLOPROPYLETHYL)AMIDE

Procedure

Following the procedure of Example 9, making variations only as required to use (2-trifluoromethylphenyl)acetic acid in place of 2,5-dichlorobenzoic acid to react with 6-piperazin-1-ylpyridazine-3-carboxylic acid (2-cyclopropylethyl)-amide, the title compound was obtained as a white solid (78.7% yield). 1H NMR (300 MHz, CDCl3) δ 8.03, 7.97, 7.67-7.64, 7.53-7.48, 7.39-7.35, 6.96, 3.91, 3.87-3.67, 3.66-3.6, 3.58-3.51, 1.53-1.46, 0.78-0.64, 0.48-0.42, 0.10-0.06. 13C NMR (75 MHz, CDCl3) δ 168.8, 162.9, 159.9, 145.3, 133.2, 132.0, 131.5, 128.5, 128.2, 127.2, 127.0, 126.3, 126.2, 125.5, 112.3, 45.0, 44.7, 44.2, 41.2, 39.6, 37.13, 37.11, 34.4, 8.6, 4.2. MS (ES+) m/z 462.2 (M+1).

Sources & evidence

ORD record
ord-4fc959f2d91e4998be421b2d3747a555
Source dataset
uspto-grants-2010_07
Patent number
US07754711B2

Reaction notes

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