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

HRID 595932노트

반응식

HRID 595932 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d33774b115b54df3b8b879c9c18dabfe
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242996B2

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