Dimethylformamide → 2-Phenyl-pyrimidine-5-carboxylic acid (3-phenyl-[1,2,4]thiadiazol-5-yl)-amide

HRID 219685ノート

反応式

HRID 219685 の反応式
[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]=1

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 285611,2,4-Thiadiazol-5-amine, 3-phenyl-HCID 65578Oxalyl chlorideHCID 7473892-Phenylpyrimidine-5-carboxylic acid

生成物 1

HCID 598058282-Phenyl-pyrimidine-5-carboxylic acid (3-phenyl-[1,2,4]thiadiazol-5-yl)-amide収率 59.6%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  1. additionis added at 0° C.
  2. temperaturewarmed to room temperature
  3. stirringstirred for 20 additional min
  4. concentrationThe mixture is concentrated in vacuo
  5. dissolutionThe residue is dissolved in DCM
  6. stirringThe mixture is stirred at room temperature for two hours
  7. concentrationconcentrated in vacuo
  8. customThe residue is triturated in DCM

出典と根拠

ORDレコード
ord-863c4a259fb546c9a5712c49d3071187
出典データセット
uspto-grants-2012_06
特許番号
US08202863B2

反応ノート

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