5-(Chloromethyl)-2-(trifluoromethyl)pyridine → 6-(2-chlorophenyl)-7-(4-chlorophenyl)-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one

HRID 2250347Notes

Reaction equation

HRID 2250347 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[CH:10][C:11]2[N:12]([C:14](=[O:17])[NH:15][N:16]=2)[N:13]=1.Cl[CH2:26][C:27]1[CH:28]=[CH:29][C:30]([C:33]([F:36])([F:35])[F:34])=[N:31][CH:32]=1.FC(F)(F)C1C=CC(CN2C(=O)N3N=C(C4C=CC=CC=4Cl)C(C4C=CC(Cl)=CC=4)=CC3=N2)=CC=1>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([C:18]2[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=2)=[CH:10][C:11]2[N:12]([C:14](=[O:17])[N:15]([CH2:26][C:27]3[CH:32]=[N:31][C:30]([C:33]([F:36])([F:34])[F:35])=[CH:29][CH:28]=3)[N:16]=2)[N:13]=1

Participants

4

Reactant 3

HCID 27738105-(Chloromethyl)-2-(trifluoromethyl)pyridineHCID 156035292-(4-(trifluoromethyl)benzyl)-6-(2-chlorophenyl)-7-(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-oneHCID 596416776-(2-chlorophenyl)-7-(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one

Product 1

HCID 156035306-(2-chlorophenyl)-7-(4-chlorophenyl)-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one

Procedure

The title compound was prepared from 6-(2-chlorophenyl)-7-(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (79 mg, 0.22 mmol) and 5-(chloromethyl)-2-(trifluoromethyl)pyridine (74 mg, 0.38 mmol) according to the procedures described for 2-(4-(trifluoromethyl)benzyl)-6-(2-chlorophenyl)-7-(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (Example 2). The crude product was purified using a silica gel cartridge (12 g) eluting with a gradient of EtOAc (0-80%) in hexanes to obtain the desired product as a yellow foam, which was lyophilized in acetonitrile to afford 87 mg (76%) of the title compound as a yellow powder. LC/MS (method A): retention time=3.76 min, (M+H)+=516. 1H NMR (CDCl3, 400 MHz): δ 8.86 (s, 1H), 8.02 (d,J=8.3 Hz, 1H), 7.47 (m, 1H), 7.42 (s, 1H), 7.33 (m, 2H), 7.25 (m, 2H), 7.20 (d,J=8.8 Hz, 2H), 7.02 (d,J=8.8 Hz, 2H), 5.34 (s, 2H).

Workup

  1. customThe crude product was purified
  2. washeluting with a gradient of EtOAc (0-80%) in hexanes

Sources & evidence

ORD record
ord-4e23f5d51f2044f4b7d9f3d8ce694032
Source dataset
uspto-grants-2008_01
Patent number
US07317012B2

Reaction notes

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