Valeryl chloride → {4-[6-(5-Butyl[1,2,4]oxadiazol-3-YL)pyridazin-3-YL]piperazin-1-YL}-(2-trifluoromethylphenyl)methanone

HRID 499169Notes

Reaction equation

[C:1](Cl)(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].O[NH:9][C:10]([C:12]1[N:13]=[N:14][C:15]([N:18]2[CH2:23][CH2:22][N:21]([C:24](=[O:35])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]([F:34])([F:33])[F:32])[CH2:20][CH2:19]2)=[CH:16][CH:17]=1)=[NH:11]>>[CH2:2]([C:1]1[O:6][N:11]=[C:10]([C:12]2[N:13]=[N:14][C:15]([N:18]3[CH2:19][CH2:20][N:21]([C:24]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[C:31]([F:34])([F:33])[F:32])=[O:35])[CH2:22][CH2:23]3)=[CH:16][CH:17]=2)[N:9]=1)[CH2:3][CH2:4][CH3:5]

Participants

Reactant 2

HCID 61186Valeryl chloride

HCID 178513336HCID 178513336, compound

Product 1

HCID 11604994{4-[6-(5-Butyl[1,2,4]oxadiazol-3-YL)pyridazin-3-YL]piperazin-1-YL}-(2-trifluoromethylphenyl)methanoneYield 48%

Procedure

Following the procedure as described in Example 4, making variations only as required to use valeryl chloride in place of propionyl chloride to react with N-hydroxy-6-[4-(2-trifluoromethylbenzoyl)piperazin-1-yl]pyridazine-3-carboxamidine, the title compound was obtained as white crystals in 48% yield (0.110 g). m.p. 175° C. 1H NMR (300 MHz, CDCl3) 7.90 (d, J=9.3 Hz, 1H), 7.75 (d, J=7.6 Hz, 1H), 7.67-7.48 (m, 2H), 7.30 (d, J=7.5 Hz, 1H), 7.00 (d, J=9.3 Hz, 1H), 4.15-3.65 (m, 6H), 3.32 7.30 (t, J=4.9 Hz, 2H), 2.95 (t, J=7.7 Hz, 2H), 1.92-1.75 (m, 2H), 1.48-1.35 (m, 2H), 0.90 (t, J=7.3 Hz, 2H). 13C NMR (75 MHz, CDCl3) δ 167.6, 166.5, 142.0, 134.3, 134.3, 132.3, 129.4, 127.3, 127.2, 127.1, 126.9, 126.8, 126.8, 111.8, 46.4, 44.6, 44.3, 41.2, 28.5, 26.3, 22.1, 13.5. MS (ES+) m/z 461.2 (M+1).

Sources & evidence

ORD record: ord-b37aae4cd3344217b62eb991e2822d1d
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767677B2

Reaction notes

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