Triethylamine → N-(3-chloro-4-(4-isobutyrylpiperazin-1-yl)phenyl)picolinamide

HRID 38249

反応式

HRID 38249 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.[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][N:28]([C:31](=[O:35])[CH:32]([CH3:34])[CH3:33])[CH2:27][CH2:26]2)=[C:21]([Cl:36])[CH:20]=1>C(Cl)Cl>[Cl:36][C:21]1[CH:20]=[C:19]([NH:18][C:8](=[O:9])[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=2)[CH:24]=[CH:23][C:22]=1[N:25]1[CH2:30][CH2:29][N:28]([C:31](=[O:35])[CH:32]([CH3:33])[CH3:34])[CH2:27][CH2:26]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 135033Picolinoyl Chloride HydrochlorideHCID 9369261-(4-(4-Amino-2-chlorophenyl)piperazin-1-yl)-2-methylpropan-1-one

生成物 1

HCID 42645025N-(3-chloro-4-(4-isobutyrylpiperazin-1-yl)phenyl)picolinamide収率 18%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

According to Scheme 4 Step 3: Picolinoyl chloride hydrochloride (0.93 mmol, 178 mg) and Et3N (1.86 mmol, 0.26 mL) were added to a solution of 1-(4-(4-amino-2-chlorophenyl)piperazin-1-yl)-2-methylpropan-1-one (0.62 mmol, 175 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 Na2SO4, was filtered and was concentrated under reduced pressure. The crude product was purified by flash chromatography over C18 column using water/ACN (60:40) as eluent to afford N-(3-chloro-4-(4-isobutyrylpiperazin-1-yl)phenyl)picolinamide (0.11 mmol, 42 mg, 18%) 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 Na2SO4
  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-bf9a8f47cc0d45d592b8c2e6d4a9879b
出典データセット
uspto-grants-2013_09
特許番号
US08524726B2

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