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

HRID 38252노트

반응식

HRID 38252 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-85b89279c2bd4d0dafccb9dbb4150929
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524726B2

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