7-Chloro-8-(4-chlorophenyl)-2-(6-(trifluoromethyl)pyridin-3-yl)methyl-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one → 8-(4-chlorophenyl)-7-(4-(oxazol-2-yl)phenyl)-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one

HRID 2224258Notes

Reaction equation

HRID 2224258 reaction equation
Cl[C:2]1[CH:7]=[N:6][N:5]2[C:8](=[O:22])[N:9]([CH2:11][C:12]3[CH:13]=[N:14][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:17]=3)[N:10]=[C:4]2[C:3]=1[C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1.CC1(C)C(C)(C)OB([C:38]2[CH:43]=[CH:42][C:41]([C:44]3[O:45][CH:46]=[CH:47][N:48]=3)=[CH:40][CH:39]=2)O1>>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([C:3]2[C:4]3[N:5]([C:8](=[O:22])[N:9]([CH2:11][C:12]4[CH:13]=[N:14][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:16][CH:17]=4)[N:10]=3)[N:6]=[CH:7][C:2]=2[C:38]2[CH:43]=[CH:42][C:41]([C:44]3[O:45][CH:46]=[CH:47][N:48]=3)=[CH:40][CH:39]=2)=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 597169037-Chloro-8-(4-chlorophenyl)-2-(6-(trifluoromethyl)pyridin-3-yl)methyl-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-oneHCID 597169152-(4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3-oxazole

Product 1

HCID 597165758-(4-chlorophenyl)-7-(4-(oxazol-2-yl)phenyl)-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one

Procedure

7-Chloro-8-(4-chlorophenyl)-2-(6-(trifluoromethyl)pyridin-3-yl)methyl-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one, prepared as described in Example 277 and 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)oxazole were reacted using procedures analogous to those described in Example 276 to give the title compound, 8-(4-chlorophenyl)-7-(4-(oxazol-2-yl)phenyl)-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one. HPLC: 99% at 8.42 min (retention time) (Conditions: Zorbax SB C18 (4.6×75 mm); Eluted with 0% to 100% B, 8 min gradient. (A=90% H2O—10% MeOH—0.1% H3PO4 and B=10% H2O—90% MeOH—0.1% H3PO4); Flow rate at 2.5 mL/min. UV detection at 220 nm). MS (ES): m/z 549 [M+H]+; 1H NMR (CDCl3, 400 MHz): δ 5.32 (s, 2H), 7.23-7.32 (m, 2H), 7.40-7.59 (m, 4H), 7.62-7.78 (m, 4H), 7.90-8.05 (m, 2H), 8.24-8.27 (m, 1H), 8.81 (s, 1H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-ca7d602d900844399511e163ce52ead1
Source dataset
uspto-grants-2008_05
Patent number
US07378418B2

Reaction notes

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