Water → 9-Benzhydryloxy-7-(2,4-dimethoxy-benzyl)-5-methoxy-pyrrolo[3,4-g]quinoline-6,8-dione

HRID 853699

반응식

HRID 853699 반응식
C(=O)([O-])[O-].[K+].[K+].C(O[C:10](=O)[O:11][C:12]1[C:21]2[C:22](=[O:37])[N:23]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][C:28]=3[O:35][CH3:36])[C:24](=[O:25])[C:20]=2[C:19]([O:38][CH:39]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[C:18]2[C:13]=1[CH:14]=[CH:15][CH:16]=[N:17]2)C.O.IC>O1CCCC1.C(OCC)(=O)C>[CH:39]([O:38][C:19]1[C:20]2[C:24](=[O:25])[N:23]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][C:28]=3[O:35][CH3:36])[C:22](=[O:37])[C:21]=2[C:12]([O:11][CH3:10])=[C:13]2[C:18]=1[N:17]=[CH:16][CH:15]=[CH:14]2)([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium Carbonate2회HCID 58928675carbonic acid 9-benzhydryloxy-7-(2,4-dimethoxy-benzyl)-6,8-dioxo-7,8-dihydro-6H-pyrrolo [3,4-g]quinolin-5-yl ester ethyl ester

생성물 1

HCID 589290149-Benzhydryloxy-7-(2,4-dimethoxy-benzyl)-5-methoxy-pyrrolo[3,4-g]quinoline-6,8-dione수율 100%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

Potassium carbonate (2.6 g, 19.0 mmol) and N,N-dimethyl-aminopyridine (DMAP, 0.464 g, 3.8 mmol) were added to carbonic acid 9-benzhydryloxy-7-(2,4-dimethoxy-benzyl)-6,8-dioxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinolin-5-yl ester ethyl ester 301 (1.2 g, 1.9 mmol) dissolved in tetrahydrofuran (40 ml) and water (20 ml) was added. After stirring overnight at room temperature, the reaction mixture was concentrated in vacuo and diluted with ethyl acetate. It was washed twice with 5% citric Acid (aqueous), twice with water, once with brine, dried over magnesium sulfate, and concentrated in vacuo. The resulting residue was dissolved in dimethylformamide (10 ml). To this reaction mixture was added potassium carbonate (1.24 g, 9.0 mmol) and iodomethane (methyl iodide, MeI, 2.55 g, 18.0 mmol). After stirring overnight at room temperature, the reaction mixture was diluted with ethyl acetate, washed twice with 5% citric acid, twice with water, once with brine, and concentrated in vacuo to afford 9-benzhydryloxy-7-(2,4-dimethoxy-benzyl)-5-methoxy-pyrrolo[3,4-g]quinoline-6,8-dione 302 (1.1 g, 1.9 mmol, 100%). 1H NMR (d-DMSO) δ 9.16 (dd, 1H), 8.60 (dd, 1H), 7.82 (s, 1H), 7.75 (m, 1H), 7.54 (d, 4H), 7.16 (m, 6H), 6.82 (d, 1H), 6.56 (d, 1H), 6.44 (dd, 1H), 4.66 (s, 2H), 4.10 (s, 3H), 3.76 (s, 3H), 3.70 (s, 3H). MS: 583.2 (M+23).

후처리

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additiondiluted with ethyl acetate
  3. washIt was washed twice with 5% citric Acid (aqueous), twice with water, once with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. dissolutionThe resulting residue was dissolved in dimethylformamide (10 ml)
  7. stirringAfter stirring overnight at room temperature
  8. washwashed twice with 5% citric acid, twice with water, once with brine
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-7c57823a803446cfa812c31b1b310a2c
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253180B2

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