3-Aminopiperidine-2,6-dione hydrochloride → 2-(2,6-Dioxo-3-piperidyl)-4-(pentylamino)isoindoline-1,3-dione

HRID 9997

반응식

HRID 9997 반응식
[CH2:1]([NH:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:9]([C:10]([OH:12])=O)[C:8]=1[C:16]([OH:18])=O)[CH2:2][CH2:3][CH2:4][CH3:5].Cl.[NH2:20][CH:21]1[CH2:26][CH2:25][C:24](=[O:27])[NH:23][C:22]1=[O:28]>C(O)(=O)C>[O:28]=[C:22]1[CH:21]([N:20]2[C:16](=[O:18])[C:8]3[C:9](=[CH:13][CH:14]=[CH:15][C:7]=3[NH:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[C:10]2=[O:12])[CH2:26][CH2:25][C:24](=[O:27])[NH:23]1

참가 물질

4

반응물 2

HCID 1345483-Aminopiperidine-2,6-dione hydrochlorideHCID 219885603-Pentylamino-phthalic acid

생성물 1

HCID 99026612-(2,6-Dioxo-3-piperidyl)-4-(pentylamino)isoindoline-1,3-dione수율 53%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

To a stirred solution of 3-pentylamino-phthalic acid (2.51 g, 10 mmol) in acetic acid (50 ml) was added 3-amino-piperidine-2,6-dione hydrochloride (1.81 g, 11 mmol). The reaction mixture was heated to reflux overnight. The solvent was evaporated in vacuo and the residue dissolved in ethyl acetate (100 ml). The ethyl acetate mixture was washed with water (2×100 ml), saturated aqueous sodium bicarbonate (2×100 ml), brine (1×100 ml), and dried (MgSO4). The solvent was evaporated in vacuo and the solid residue was purified by chromatography (25% ethyl acetate/hexane) to give 1.82 g (53%) of product as a yellow solid: mp 141–143° C.; 1H NMR (DMSO-d6) d 11.09 (s, 1H), 7.58 (t, J=8.3 Hz, 1H), 7.08 (d, J=8.6 Hz, 1H), 7.02 (d, J=7.0 Hz, 1H), 6.519 (t, J=5.7 Hz, 1H), 5.06 (dd, J=5.3 and 12.4 Hz, 1H), 3.32–3.25 (m, 2H), 2.97–2.82 (m, 1H), 2.62–2.46 (m, 2H), 2.06–2.01 (m, 1H), 1.61–1.55 (m, 2H), 1.35–1.32 (m, 4H), 0.88 (t, J=6.7 Hz, 3H); 13C NMR (DMSO-d6) d 172.72, 170.01, 168.92, 167.25, 146.39, 136.21, 132.14, 117.08, 110.31, 108.99, 48.52, 41.77, 30.94, 28.46, 28.33, 22.12, 21.82, 13.85; Anal. Calcd. For C18H21N3O4: C, 62.96; H, 6.16; N, 12.24. Found: C, 62.92; H, 6.17; N, 12.15.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux overnight
  3. customThe solvent was evaporated in vacuo
  4. dissolutionthe residue dissolved in ethyl acetate (100 ml)
  5. washThe ethyl acetate mixture was washed with water (2×100 ml), saturated aqueous sodium bicarbonate (2×100 ml), brine (1×100 ml)
  6. dry with materialdried (MgSO4)
  7. customThe solvent was evaporated in vacuo
  8. customthe solid residue was purified by chromatography (25% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-7a35a5908175421aac37278eea689741
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091353B2

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