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

HRID 1879330ノート

反応式

HRID 1879330 の反応式
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.CCN(CC)CC>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

参加物

5

反応物 3

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

生成物 1

HCID 593162336-(7-Azabicyclo[2.2.1]heptan-7-yl)-4-methylpyridin-3-amine収率 81.9%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

To a solution of 2-fluoro-4-methyl-5-nitropyridine (150 mg, 0.9608 mmol) in acetonitrile (5 mL) was added 7-azabicyclo[2.2.1]heptane hydrochloride (152.9 mg, 1.153 mmol) and Et3N (243.1 mg, 334.8 μL, 2.402 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 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) 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).

後処理

  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

出典と根拠

ORDレコード
ord-f9f80694cdd2474f880ac8457c037cf6
出典データセット
uspto-grants-2012_11
特許番号
US08314239B2

反応ノート

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