Hydrochloric Acid → N-(3-chloro-4-(piperazin-1-yl)phenyl)picolinamide

HRID 38252ノート

反応式

HRID 38252 の反応式
Cl.O1CCOCC1.[Cl:8][C:9]1[CH:14]=[C:13]([NH:15][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[CH:12]=[CH:11][C:10]=1[N:24]1[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]1>C(Cl)Cl>[Cl:8][C:9]1[CH:14]=[C:13]([NH:15][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[CH:12]=[CH:11][C:10]=1[N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 67441071Tert-butyl 4-(2-chloro-4-(picolinamido)phenyl)piperazine-1-carboxylate

生成物 1

HCID 67441344N-(3-chloro-4-(piperazin-1-yl)phenyl)picolinamide収率 40%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

According to Scheme 5 Step 4: HCl 4 M in dioxane (12.3 mmol, 3.07 mL) was added to a solution of tert-butyl 4-(2-chloro-4-(picolinamido)phenyl)piperazine-1-carboxylate (2.46 mmol, 1.02 g) in DCM (10 mL). The reaction mixture was stirred at room temperature overnight. After evaporation, DCM was added and then a NaOH 1 M solution. The aqueous phase was extracted with DCM. 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 silica gel using cyclohexane/AcOEt (60:40) as eluent to afford N-(3-chloro-4-(piperazin-1-yl)phenyl)picolinamide (0.97 mmol, 308 mg, 40%) as an orange solid.

後処理

  1. customAfter evaporation, DCM
  2. additionwas added
  3. extractionThe aqueous phase was extracted with DCM
  4. washThe organic phase was washed with brine
  5. dry with materialwas dried over MgSO4
  6. filtrationwas filtered
  7. concentrationwas concentrated under reduced pressure
  8. customThe crude product was purified by flash chromatography over silica gel

出典と根拠

ORDレコード
ord-85b89279c2bd4d0dafccb9dbb4150929
出典データセット
uspto-grants-2013_09
特許番号
US08524726B2

反応ノート

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