3-Aminopiperidine-2,6-dione hydrochloride → 2-(2,6-Dioxopiperidin-3-yl)-4-(3-ethoxy-4-methoxyphenylamino)-isoindole-1,3-dione

HRID 448339노트

반응식

HRID 448339 반응식
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([NH:12][C:13]2[CH:21]=[CH:20][CH:19]=[C:15]([C:16]([OH:18])=O)[C:14]=2[C:22]([OH:24])=O)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2].Cl.[NH2:26][CH:27]1[CH2:33][CH2:32][C:31](=[O:34])[NH:30][C:28]1=[O:29]>N1C=CC=CC=1>[O:29]=[C:28]1[CH:27]([N:26]2[C:22](=[O:24])[C:14]3[C:15](=[CH:19][CH:20]=[CH:21][C:13]=3[NH:12][C:6]3[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=3)[C:16]2=[O:18])[CH2:33][CH2:32][C:31](=[O:34])[NH:30]1

참가 물질

4

반응물 2

HCID 1345483-Aminopiperidine-2,6-dione hydrochlorideHCID 583071773-(3-Ethoxy-4-methoxyphenylamino)phthalic acid

생성물 1

HCID 588273482-(2,6-Dioxopiperidin-3-yl)-4-(3-ethoxy-4-methoxyphenylamino)-isoindole-1,3-dione수율 67%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

A mixture of 3-(3-ethoxy-4-methoxyphenylamino)phthalic acid (0.85 g, 2.6 mmol) and rac-α-aminoglutarimide hydrochloride (0.43 g, 2.6 mmol) in pyridine (10 mL) was heated to reflux for 16 hours. The mixture was cooled and evaporated under vacuum. The residue was dissolved in ethyl acetate (150 mL), washed with dilute aqueous HCl (2×100 mL) and water (2×100 mL), and evaporated. The residue was chromatographed in 95:5 methylene chloride-methanol, eluting 0.72 g of the product, in 67% yield: mp 162-164° C.; 1H NMR (CDCl3) δ 1.46 (t, J=7.0 Hz, 3H), 2.11-2.18 (m, 1H), 2.72-2.94 (m, 3H), 3.89 (s, 3H), 4.06 (q, J=7.0 Hz, 3H), 4.96 (dd, J=12.0 Hz, J=5.0 Hz, 1H), 6.76-6.89 (m, 3H), 7.14-7.19 (m, 2H), 7.43 (t, J=7.8 Hz, 1H), 7.86 (s, 1H), 8.43 (s, 1H); 13C NMR (CDCl3) δ 14.7, 22.8, 31.4, 49.0, 56.2, 64.5, 109.9, 110.8, 112.1, 113.1, 116.4, 118.5, 131.7, 132.4, 135.9, 145.2, 147.4, 149.1, 167.5, 168.4, 169.4, 171.1; Anal. calcd for C22H21N3O6: C, 62.41; H, 5.00; N, 9.92. Found: C, 62.16; H, 4.89; N, 9.72.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 16 hours
  3. temperatureThe mixture was cooled
  4. customevaporated under vacuum
  5. dissolutionThe residue was dissolved in ethyl acetate (150 mL)
  6. washwashed with dilute aqueous HCl (2×100 mL) and water (2×100 mL)
  7. customevaporated
  8. customThe residue was chromatographed in 95:5 methylene chloride-methanol
  9. washeluting 0.72 g of the product

출처 및 근거

ORD 기록
ord-40e0dbb58dc5411f8e3c08863ef9aced
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481568B2

반응 노트

불러오는 중…