N-bromobutanimide → 4-(6-Amino-5-bromopyridin-3-yl)-1-methylpiperidin-2-one

HRID 595916노트

반응식

HRID 595916 반응식
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([CH3:14])[C:10](=[O:15])[CH2:9]2)=[CH:4][CH:3]=1.C1C(=O)N([Br:23])C(=O)C1>C(#N)C>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([CH3:14])[C:10](=[O:15])[CH2:9]2)=[CH:4][C:3]=1[Br:23]

참가 물질

4

반응물 2

HCID 67184N-bromobutanimideHCID 118054586(+/-)-4-(6-Aminopyridin-3-yl)-1-methylpiperidin-2-one

생성물 1

HCID 1180545914-(6-Amino-5-bromopyridin-3-yl)-1-methylpiperidin-2-one

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of (+/−)-4-(6-aminopyridin-3-yl)-1-methylpiperidin-2-one (291 mg, 1.418 mmol) in acetonitrile (14.200 mL) was added NBS (202 mg, 1.134 mmol) at 0° C. The reaction mixture was stirred for 30 min upon warming-up to room temperature. After quenched with Na2S2O3 solution, the reaction mixture was extracted with EtOAc, which was washed with NaHCO3 solution and brine. The organic layer was dried over anhydrous Na2SO4, filtered off, concentrated in vacuo. The crude product (+/−)-4-(6-amino-5-bromopyridin-3-yl)-1-methylpiperidin-2-one (98%) was used for the next step. LCMS (m/z): 284/286 (MH+), 0.34 min.

후처리

  1. customAfter quenched with Na2S2O3 solution
  2. extractionthe reaction mixture was extracted with EtOAc, which
  3. washwas washed with NaHCO3 solution and brine
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered off
  6. concentrationconcentrated in vacuo
  7. custom284/286 (MH+), 0.34 min.

출처 및 근거

ORD 기록
ord-58b1500f41cb4e9199c4c8dd8876de13
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242996B2

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