Trifluoroacetic acid → 5-(4-methyltetrahydro-2H-pyran-4-yl)pyridin-2-amine

HRID 595932ノート

反応式

HRID 595932 の反応式
COC1C=C(OC)C=CC=1C[NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2([CH3:19])[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:9][N:8]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:19][C:13]1([C:10]2[CH:11]=[CH:12][C:7]([NH2:6])=[N:8][CH:9]=2)[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 118045285N-(2,4-dimethoxybenzyl)-5-(4-methyltetrahydro-2H-pyran-4-yl)pyridin-2-amine

生成物 1

HCID 1180456035-(4-methyltetrahydro-2H-pyran-4-yl)pyridin-2-amine収率 89.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

To an ice cold solution of N-(2,4-dimethoxybenzyl)-5-(4-methyltetrahydro-2H-pyran-4-yl)pyridin-2-amine (100 mg, 0.29 mmol) in DCM (6 mL) was added 10 mL 30% TFA in DCM solution. The resulting solution was stirred at 0° C. for 15 min. The solvent was removed via vacuum. The resulting residue was redissolved in ethyl acetate, and the organic solution was washed with 1M NaOH, brine, dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography on silicagel (ISCO) eluting with 0-100% ethyl acetate in heptane to give 5-(4-methyltetrahydro-2H-pyran-4-yl)pyridin-2-amine (50 mg, 0.26 mmol, 89% yield) as white color solid. LCMS (m/z): 193 (MH+), 0.35 min.

後処理

  1. customThe solvent was removed via vacuum
  2. dissolutionThe resulting residue was redissolved in ethyl acetate
  3. washthe organic solution was washed with 1M NaOH, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography on silicagel (ISCO)
  7. washeluting with 0-100% ethyl acetate in heptane

出典と根拠

ORDレコード
ord-d33774b115b54df3b8b879c9c18dabfe
出典データセット
uspto-grants-2016_01
特許番号
US09242996B2

反応ノート

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