Benzyl Bromide → HCID 42645471, 화합물

HRID 38254노트

반응식

HRID 38254 반응식
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:9][C:10]1[CH:11]=[C:12]([NH:22][C:23](=[O:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)[CH:13]=[CH:14][C:15]=1[N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH2:2]([N:19]1[CH2:20][CH2:21][N:16]([C:15]2[CH:14]=[CH:13][C:12]([NH:22][C:23](=[O:30])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)=[CH:11][C:10]=2[Cl:9])[CH2:17][CH2:18]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 67441344N-(3-chloro-4-(piperazin-1-yl)phenyl)picolinamide

생성물 1

HCID 42645471HCID 42645471, 화합물수율 192.2%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

According to Scheme 5 Step 5 Method B: A suspension of (bromomethyl)benzene (0.61 mmol, 74 μL), N-(3-chloro-4-(piperazin-1-yl)phenyl)picolinamide (0.51 mmol, 161 mg) and of K2CO3 (0.51 mmol, 70 mg) in ACN (3 mL) was stirred at 80° C. for 30 minutes. After evaporation of the solvent, water and AcOEt were added. 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 silica gel using DCM/AcOEt (80:20) as eluent and finally crystallized in pentane to obtain N-(4-(4-benzylpiperazin-1-yl)-3-chlorophenyl)picolinamide (0.98 mmol, 40 mg, 20%) as a white solid.

후처리

  1. customAfter evaporation of the solvent, water and AcOEt
  2. additionwere added
  3. extractionThe aqueous phase was extracted with AcOEt
  4. washThe organic phase was washed with brine
  5. dry with materialwas dried over Na2SO4
  6. filtrationwas filtered
  7. concentrationwas concentrated under reduced pressure
  8. customThe crude product was purified by flash chromatography over silica gel
  9. customfinally crystallized in pentane

출처 및 근거

ORD 기록
ord-ffabc75a608944ac845f7dfd6409fe52
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524726B2

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