Triethylamine → 6-(7-Azabicyclo[2.2.1]heptan-7-yl)-4-methylpyridin-3-amine

HRID 383398노트

반응식

HRID 383398 반응식
F[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-])=O)=[CH:4][N:3]=1.Cl.[CH:13]12[NH:19][CH:16]([CH2:17][CH2:18]1)[CH2:15][CH2:14]2.C(N(CC)CC)C>C(#N)C>[CH:16]12[N:19]([C:2]3[N:3]=[CH:4][C:5]([NH2:9])=[C:6]([CH3:8])[CH:7]=3)[CH:13]([CH2:18][CH2:17]1)[CH2:14][CH2:15]2

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 27831772-Fluoro-4-methyl-5-nitropyridineHCID 162795037-Azabicyclo[2.2.1]heptane hydrochloride

생성물 1

HCID 593162336-(7-Azabicyclo[2.2.1]heptan-7-yl)-4-methylpyridin-3-amine수율 82%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
80 °C

실험 절차

To a solution of 2-fluoro-4-methyl-5-nitropyridine (150 mg, 0.96 mmol) in acetonitrile (5 mL) was added 7-azabicyclo[2.2.1]heptane hydrochloride (153 mg, 1.15 mmol) and triethylamine (335 μL, 2.40 mmol). The reaction was heated at 80° C. for 16 h. The reaction was quenched with water (2 mL) and solvent was evaporated. The residue was dissolved in ethyl acetate (15 mL), washed with 1N HCl (10 mL), dried over MgSO4, filtered and concentrated in vacuo to afford 6-(7-azabicyclo[2.2.1]heptan-7-yl)-4-methylpyridin-3-amine (160 mg, 71% yield) as yellow solid which was used in next step without purification. 1H NMR (400.0 MHz, CDCl3) δ 8.96 (s, 1H), 6.37 (s, 1H), 4.59 (s, 2H), 2.59 (d, J=0.4 Hz, 3H), 1.83-1.80 (m, 4H), 1.61-1.54 (m, 4H).

후처리

  1. customThe reaction was quenched with water (2 mL) and solvent
  2. customwas evaporated
  3. dissolutionThe residue was dissolved in ethyl acetate (15 mL)
  4. washwashed with 1N HCl (10 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-61778505f3504c5c96b67bedb266f5cc
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367660B2

반응 노트

불러오는 중…