N'-(5-bromo-4-(4-chlorophenyl)pyridin-2-yl)-2-(6-(trifluoromethyl)pyridin-3-yl)acetohydrazide → 6-Bromo-7-(4-chlorophenyl)-3-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-a]pyridine

HRID 1867896Notes

Reaction equation

[Br:1][C:2]1[C:3]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)=[CH:4][C:5]([NH:8][NH:9][C:10](=O)[CH2:11][C:12]2[CH:13]=[N:14][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:17]=2)=[N:6][CH:7]=1>FC(C1C=CC=CC=1)(F)F>[Br:1][C:2]1[C:3]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)=[CH:4][C:5]2[N:6]([C:10]([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:9][N:8]=2)[CH:7]=1

Participants

Conditions

Temperature: 200 °C

Procedure

To a suspension of N′-(5-bromo-4-(4-chlorophenyl)pyridin-2-yl)-2-(6-(trifluoromethyl)pyridin-3-yl)acetohydrazide (24 mg, 0.05 mmol) in (trifluoromethyl)benzene (0.45 mL) was added glacial acidic acid (0.15 mL). The reaction mixture was sealed and heated in a microwave reactor at 200° C. for 30 min. The reaction mixture was allowed to cool to 20° C. and concentrated in vacuo. The residue was purified using reverse phase preparative HPLC (Conditions: Phemomenex Luna 5μC18 30×75 mm; Eluted with 0% to 100% B, 10 min gradient, 100% B hold for 2 min, (A=90% H2O, 10% CH3CN, 0.1% trifluoroacetic acid and B=10% H2O, 90% CH3CN, 0.1% trifluoroacetic acid); Flow rate at 40 mL/min, UV detection at 220 nm) to afford 21 mg (90%) of the title compound as a white solid. LC/MS (method B): retention time=1.86 min, [M+H]+=467.0.

Workup

customThe reaction mixture was sealed
temperatureto cool to 20° C.
concentrationconcentrated in vacuo
customThe residue was purified
washEluted with 0% to 100% B, 10 min gradient, 100% B hold for 2 min

Sources & evidence

ORD record: ord-998850aa948d4a4fa0d381207126d7bb
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07632837B2

Reaction notes

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