Dimethylformamide → HCID 15953285, compound

HRID 271448Notes

Reaction equation

[CH3:1][NH:2][C:3]1[N:8]2[C:9](=[O:12])[NH:10][N:11]=[C:7]2[C:6]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[C:5]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[N:4]=1.CN(C=O)C.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:39][C:40]1[CH:41]=[CH:42][C:43]([C:46]([F:49])([F:48])[F:47])=[N:44][CH:45]=1>CCOC(C)=O>[CH3:1][NH:2][C:3]1[N:8]2[C:9](=[O:12])[N:10]([CH2:39][C:40]3[CH:45]=[N:44][C:43]([C:46]([F:49])([F:47])[F:48])=[CH:42][CH:41]=3)[N:11]=[C:7]2[C:6]([C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)=[C:5]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[N:4]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a mixture of crude 5-(methylamino)-7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one, DMF (0.5 mL), and potassium carbonate (38 mg, 0.28 mmol) was added 5-chloromethyl-2-(trifluoromethyl)pyridine (18 mg, 0.09 mmol). The resulting reaction mixture was stirred at 70° C. for 1 h. The reaction mixture was then diluted with EtOAc, washed with water and saturated aqueous NaCl, dried (Na2SO4), and concentrated at reduced pressure. The residue was purified by preparative reverse phase HPLC to obtain 25 mg (51% over two steps) of the title compound as a light yellow solid. HPLC/MS: retention time=4.40 min, [M+H]30 =545.

Workup

customThe resulting reaction mixture
washwashed with water and saturated aqueous NaCl
dry with materialdried (Na2SO4)
concentrationconcentrated at reduced pressure
customThe residue was purified by preparative reverse phase HPLC

Sources & evidence

ORD record: ord-65cc318fddad4045bfdd3aa59d991e1a
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07452892B2

Reaction notes

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