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Dimethylformamide → HCID 15953285, compound

HRID 271448
Notes
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Reaction equation

HRID 271448 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 27738105-(Chloromethyl)-2-(trifluoromethyl)pyridineHCID 58772831HCID 58772831, compound

Product 1

HCID 15953285HCID 15953285, compound

Reagents, catalysts & solvents 1

HCID 8857
Ethyl Acetate
Solvent

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

  1. customThe resulting reaction mixture
  2. washwashed with water and saturated aqueous NaCl
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated at reduced pressure
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes