Triethylamine → N-(3-methoxy-4-(pyrimidin-2-yloxy)phenyl)picolinamide

HRID 38246

反応式

HRID 38246 の反応式
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](Cl)=[O:9].CCN(CC)CC.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][C:26]=1[O:27][C:28]1[N:33]=[CH:32][CH:31]=[CH:30][N:29]=1)[NH2:23]>C(Cl)Cl>[CH3:18][O:19][C:20]1[CH:21]=[C:22]([NH:23][C:8](=[O:9])[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=2)[CH:24]=[CH:25][C:26]=1[O:27][C:28]1[N:29]=[CH:30][CH:31]=[CH:32][N:33]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 135033Picolinoyl Chloride HydrochlorideHCID 621109613-Methoxy-4-(pyrimidin-2-yloxy)aniline

生成物 1

HCID 42645238N-(3-methoxy-4-(pyrimidin-2-yloxy)phenyl)picolinamide収率 19.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

According to Scheme 3 Step 3: Picolinoyl chloride hydrochloride (1.33 mmol, 256 mg) and Et3N (2.67 mmol, 0.37 mL) were added sequentially to a solution of 3-methoxy-4-(pyrimidin-2-yloxy)aniline (0.89 mmol, 193 mg) in DCM (3 mL) at 0° C. The reaction mixture was stirred at room temperature for 2 hours. The organic phase was washed with a saturated solution of NaHCO3. The aqueous phase was extracted with AcOEt. The organic phase was washed with brine, was dried over MgSO4, was filtered and was concentrated under reduced pressure. The crude product was purified by flash chromatography over C18 column using water/ACN (70:30) as eluent to afford N-(3-methoxy-4-(pyrimidin-2-yloxy)phenyl)picolinamide (0.17 mmol, 55 mg, 19%) as a white solid.

後処理

  1. washThe organic phase was washed with a saturated solution of NaHCO3
  2. extractionThe aqueous phase was extracted with AcOEt
  3. washThe organic phase was washed with brine
  4. dry with materialwas dried over MgSO4
  5. filtrationwas filtered
  6. concentrationwas concentrated under reduced pressure
  7. customThe crude product was purified by flash chromatography over C18 column

出典と根拠

ORDレコード
ord-a7f5fcf130d348a486c01d6789d738a7
出典データセット
uspto-grants-2013_09
特許番号
US08524726B2

関連ノート

読み込み中…