2-(Trifluoromethyl)benzoyl chloride → HCID 11568653, compound

HRID 499174Notes

Reaction equation

HRID 499174 reaction equation
[N:1]1([C:7]2[N:12]=[N:11][C:10]([C:13]3[NH:17][C:16]4[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=4[N:14]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[F:22][C:23]([F:34])([F:33])[C:24]1[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26](Cl)=[O:27]>>[NH:14]1[C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=[C:13]1[C:10]1[N:11]=[N:12][C:7]([N:1]2[CH2:6][CH2:5][N:4]([C:26]([C:25]3[CH:29]=[CH:30][CH:31]=[CH:32][C:24]=3[C:23]([F:22])([F:33])[F:34])=[O:27])[CH2:3][CH2:2]2)=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 67523199HCID 67523199, compound

Product 1

HCID 11568653HCID 11568653, compoundYield 27%

Procedure

Following the procedure as described in Example 6, making variations only as required to use 2-(6-piperazin-1-ylpyridazin-3-yl)-1H-benzoimidazole in place of 2-(6-piperazin-1-ylpyridin-3-yl)-1H-benzoimidazole to react with 2-trifluoromethylbenzoyl chloride, the title compound was obtained as a white powder in 27% yield (0.122 g). 1H NMR (300 MHz, CDCl3) δ 13.25 (s, 1H), 8.16 (d, J=9.6 Hz, 1H), 7.82 (d, J=7.8 Hz, 1H), 7.75 (t, J=7.5 Hz, 1H), 7.65 (t, J=7.6 Hz, 2H), 7.54 (d, J=7.5 Hz, 1H), 7.47 (d, J=7.6 Hz, 1H), 7.42 (d, J=9.6 Hz, 1H), 7.22-7.13 (m, 2H), 3.87-3.56 (m, 6H), 3.26-3.12 (m, 2H). 13C NMR (75 MHz, CDCl3) δ 165.1, 158.2, 148.1, 142.8, 142.5, 133.7, 133.4, 131.8, 128.4, 126.4, 125.4, 124.9, 124.4, 124.3, 123.9, 121.8, 120.8, 117.8, 112.4, 110.6, 44.8, 42.9, 42.7, 39.6. MS (ES+) m/z 453.3 (M+1).

Sources & evidence

ORD record
ord-8b740c895f054e7eb346dda56d154be4
Source dataset
uspto-grants-2010_08
Patent number
US07767677B2

Reaction notes

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