2-(Trifluoromethyl)benzoyl chloride → HCID 11576726, compound

HRID 499175Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([C:10]3[N:11]=[N:12][C:13]([N:16]4[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]4)=[CH:14][CH:15]=3)[NH:7][C:6]=2[CH:22]=1.[F:23][C:24]([F:35])([F:34])[C:25]1[CH:33]=[CH:32][CH:31]=[CH:30][C:26]=1[C:27](Cl)=[O:28]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([C:10]3[N:11]=[N:12][C:13]([N:16]4[CH2:17][CH2:18][N:19]([C:27]([C:26]5[CH:30]=[CH:31][CH:32]=[CH:33][C:25]=5[C:24]([F:23])([F:34])[F:35])=[O:28])[CH2:20][CH2:21]4)=[CH:14][CH:15]=3)[NH:7][C:6]=2[CH:22]=1

Participants

Reactant 2

HCID 675612-(Trifluoromethyl)benzoyl chloride

HCID 67523347HCID 67523347, compound

Product 1

HCID 11576726HCID 11576726, compoundYield 24%

Procedure

Following the procedure as described in Example 6, making variations only as required to use 6-chloro-2-(6-piperazin-1-yl-pyridazin-3-yl)-1H-benzoimidazole in place of 2-(6-piperazin-1-ylpyridin-3-yl)-1H-benzoimidazole to react with 2-trifluoromethyl-benzoyl chloride, the title compound was obtained as a white powder in 24% yield (0.118 g). 1H NMR (300 MHz, CDCl3) δ 13.4 (m, 1H), 8.15 (d, J=9.5 Hz, 1H), 7.82 (d, J=7.8 Hz, 1H), 7.76 (t, J=7.5 Hz, 1H), 7.70-7.63 (m, 2H), 7.54 (d, J=7.5 Hz, 1H), 7.48-7.45 (m, 1H), 7.42 (d, J=9.6 Hz, 1H), 7.24-7.16 (m, 1H), 3.83-3.59 (m, 6H), 3.30-3.20 (m, 2H). MS (ES+) m/z 487.4 (M+1).

Sources & evidence

ORD record: ord-f84404919d074b4591d3f693a8d17ca0
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767677B2

Reaction notes

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