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

HRID 448339ノート

反応式

HRID 448339 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-40e0dbb58dc5411f8e3c08863ef9aced
出典データセット
uspto-grants-2013_07
特許番号
US08481568B2

反応ノート

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