Dimethylformamide → 2-Phenyl-pyrimidine-5-carboxylic acid (3-phenyl-[1,2,4]thiadiazol-5-yl)-amide
Reaction equation
[C:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13]([OH:15])=O)=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.CN(C=O)C.[C:27]1([C:33]2[N:37]=[C:36]([NH2:38])[S:35][N:34]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(Cl)Cl.CN1C(=O)CCC1>[C:27]1([C:33]2[N:37]=[C:36]([NH:38][C:13]([C:10]3[CH:11]=[N:12][C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[N:8][CH:9]=3)=[O:15])[S:35][N:34]=2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a suspension of 2-phenyl-pyrimidine-5-carboxylic acid (400 mg, 2 mmol) in DCM (10 mL), oxalyl chloride (0.2 mL, 2.3 mmol) is added at 0° C. followed by DMF (0.23 mL, 3 mmol). The mixture is stirred at 0° C. for 20 minutes, warmed to room temperature and stirred for 20 additional min. The mixture is concentrated in vacuo. The residue is dissolved in DCM and 3-phenyl-[1,2,4]thiadiazol-5-ylamine (248 mg, 1.4 mmol) is added followed by NMP (0.5 mL). The mixture is stirred at room temperature for two hours, and concentrated in vacuo. The residue is triturated in DCM to afford 2-phenyl-pyrimidine-5-carboxylic acid (3-phenyl-[1,2,4]thiadiazol-5-yl)-amide (300 mg) as a solid. MS: 360 (M+H); IC50=30 nM.
Workup
- additionis added at 0° C.
- temperaturewarmed to room temperature
- stirringstirred for 20 additional min
- concentrationThe mixture is concentrated in vacuo
- dissolutionThe residue is dissolved in DCM
- stirringThe mixture is stirred at room temperature for two hours
- concentrationconcentrated in vacuo
- customThe residue is triturated in DCM
Sources & evidence
- ORD record
- ord-863c4a259fb546c9a5712c49d3071187
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08202863B2
Reaction notes
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