Dimethylformamide → 4-Amino-2-[1-(ethoxy-4-methoxyphenyl)-3-hydroxybutyl]isoindoline-1,3-dione

HRID 2282959노트

반응식

HRID 2282959 반응식
Cl.[NH2:2][CH:3]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10](OCC)[CH:9]=1)[CH2:4][CH:5]([OH:7])[CH3:6].[NH2:19][C:20]1[CH:35]=[CH:34][CH:33]=[C:22]2[C:23](N(C(OCC)=O)[C:26](=[O:27])[C:21]=12)=[O:24].C(N([CH2:41][CH3:42])CC)C.CN(C)C=[O:46]>>[NH2:19][C:20]1[CH:35]=[CH:34][CH:33]=[C:22]2[C:21]=1[C:26](=[O:27])[N:2]([CH:3]([C:8]1[CH:9]=[CH:10][C:11]([O:14][CH3:15])=[CH:12][C:13]=1[O:46][CH2:41][CH3:42])[CH2:4][CH:5]([OH:7])[CH3:6])[C:23]2=[O:24]

참가 물질

5

반응물 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 187583154-Amino-4-(3-ethoxy-4-methoxyphenyl)butan-2-ol hydrochlorideHCID 187583363-amino-N-ethoxycarbonylphthalimide

생성물 1

HCID 187583214-Amino-2-[1-(ethoxy-4-methoxyphenyl)-3-hydroxybutyl]isoindoline-1,3-dione수율 52%

반응 조건

온도
85 °C

실험 절차

A mixture of 4-amino-4-(3-ethoxy-4-methoxyphenyl)butan-2-ol hydrochloride (1.0 g, 3.63 mmol), 3-amino-N-ethoxycarbonylphthalimide (0.85 g, 3.63 mmol) and triethylamine (2.37 g, 3.63 mmol) in dimethylformamide (15 mL) was heated at 80-90° C. for 16 hours. The mixture was concentrated in vacuo and the residue was stirred with methylene chloride (10 mL). The mixture was filtered and the filtrate was concentrated and purified by chromatography (silica gel, methylene chloride:ethyl acetate 8:2) to give 4-amino-2-[1-(ethoxy-4-methoxyphenyl)-3-hydroxybutyl]isoindoline-1,3-dione as a white solid (0.72 g, 52%); 1H NMR (CDCl3) δ 7.41-7.35 (m, 1H), 7.11-7.05 (m, 3H), 6.83-6.80 (m, 2H), 5.54-5.48 (dd, J=4.1 and 11.8 Hz, 1H), 5.22 (s, 2H), 4.10 (q, 2H), 3.85 (s, 3H), 3.77 (m, 1H), 2.88-2.77 (m, 1H), 2.07-1.00 (m, 1H), 1.67 (s, 1H), 1.45 (t, 3H), 1.27 (d, 3H).

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. custompurified by chromatography (silica gel, methylene chloride:ethyl acetate 8:2)

출처 및 근거

ORD 기록
ord-c4dd12f9e896439984cbfdf8fa493be8
출처 데이터셋
uspto-grants-2015_09
특허 번호
USRE045685E1

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