2-(Trifluoromethyl)benzoyl chloride → HCID 11502479, compound

HRID 499172Notes

Reaction equation

HRID 499172 reaction equation
[N:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[F:19][C:20]([F:31])([F:30])[C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23](Cl)=[O:24]>>[N:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:10]1[CH:11]=[N:12][C:7]([N:1]2[CH2:6][CH2:5][N:4]([C:23]([C:22]3[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=3[C:20]([F:19])([F:30])[F:31])=[O:24])[CH2:3][CH2:2]2)=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 67523240HCID 67523240, compound

Product 1

HCID 11502479HCID 11502479, compoundYield 20%

Procedure

Following the procedure as described in Example 5, making variations only as required to use 6′-piperazin-1-yl-[2,3′]bipyridine in place of 3-piperazin-1-yl-6-pyridin-2-ylpyridazine to react with 2-trifluoromethylbenzoyl chloride, the title compound was obtained as a white solid in 20% yield (0.102 g). 1H NMR (300 MHz, CDCl3) δ 8.75 (m, 1H), 8.62 (m, 1H), 8.19 (m, 1H), 7.73-7.67 (m, 2H), 7.63-7.58 (m, 2H), 7.53 (t, J=7.4 Hz, 7.39, 1H), 7.35 (d, J=7.4 Hz, 1H), 7.16 (m, 1H), 6.73 (d, J=8.9 Hz, 1H), 4.01-3.85 (m, 2H), 3.73-3.69 (m, 2H), 3.59-3.56 (m, 2H), 3.31-3.28 (m, 2H). 13C NMR (75 MHz, CDCl3) δ 167.5, 158.9, 155.1, 149.7, 146.6, 136.7, 136.3, 132.2, 129.3, 127.3, 126.8, 126.7, 125.3, 121.5, 119.2, 106.9, 134.6, 46.7, 45.0, 44.9, 41.4. MS (ES+) m/z 413.1 (M+1).

Sources & evidence

ORD record
ord-d5ff6673ff134e5291b2beadef586f01
Source dataset
uspto-grants-2010_08
Patent number
US07767677B2

Reaction notes

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