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

HRID 219685노트

반응식

HRID 219685 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-863c4a259fb546c9a5712c49d3071187
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202863B2

반응 노트

불러오는 중…