Pyrazole → HCID 178486388, 화합물

HRID 1052142노트

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HRID 1052142 반응식
Br[CH2:2][CH2:3][CH2:4][N:5]1[C:14]2[C:15]3[CH:16]=[C:17]4[O:25][CH2:24][O:23][C:18]4=[CH:19][C:20]=3[C:21](=[O:22])[C:13]=2[C:12]2[C:7](=[CH:8][C:9]([O:28][CH3:29])=[C:10]([O:26][CH3:27])[CH:11]=2)[C:6]1=[O:30].[H-].[Na+].[NH:33]1[CH:37]=[CH:36][CH:35]=[N:34]1>CN(C=O)C.O>[NH:33]1[CH:37]=[CH:36][C:35]([CH2:2][CH2:3][CH2:4][N:5]2[C:14]3[C:15]4[CH:16]=[C:17]5[O:25][CH2:24][O:23][C:18]5=[CH:19][C:20]=4[C:21](=[O:22])[C:13]=3[C:12]3[C:7](=[CH:8][C:9]([O:28][CH3:29])=[C:10]([O:26][CH3:27])[CH:11]=3)[C:6]2=[O:30])=[N:34]1

참가 물질

6

반응물 3

HCID 1048PyrazoleHCID 24758Sodium hydrideHCID 106242586-(3-bromo-1-propyl)-5,6-dihydro-2,3-dimethoxy-8,9-methylenedioxy-5,11-dioxo-11H-indeno[1,2-c]isoquinoline

생성물 1

HCID 178486388HCID 178486388, 화합물수율 57.6%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

6-(3-Bromo-1-propyl)-5,6-dihydro-2,3-dimethoxy-8,9-methylenedioxy-5,11-dioxo-11H-indeno[1,2-c]isoquinoline (5y) (0.2113 g, 0.448 mmol) was added to sodium hydride (86.8 mg of a 60% suspension in mineral oil, 2.17 mmol) and pyrazole (0.1749 g, 2.57 mmol) in DMF (50 mL) and the reaction mixture was heated at 60° C. for 4 h. The reaction mixture was diluted with water (200 mL) and extracted with chloroform (200 mL). The organic layer was washed with water (7×200 mL) and concentrated. Benzene was added (2×30 mL) and the mixture was concentrated again. The residue was dissolved in chloroform (4 mL) and diethyl ether (50 mL) was added. The precipitate was washed with diethyl ether (100 mL) and a dark red solid (118.5 mg, 57.6%) was obtained: mp 262-264° C. (dec). IR (film) 3462, 3104, 2918, 1693, 1640, 1557, 1495, 1488, 1430, 1394, 1308, 1284, 1251, 1205, 868, 785, 769 cm−1; 1H NMR (DMSO-d6) δ 7.97 (s, 1H), 7.65 (d, J=1.5 Hz, 1H), 7.61 (s, 1H), 6.57 (s, 1H), 6.97 (s, 1H), 6.68 (s, 1H), 6.33 (s, 1H), 6.05 (s, 2H), 4.40 (m, 4H), 4.01 (s, 3H), 3.96 (s, 3H), 2.45 (m, 2H); ESIMS m/z (rel intensity) 460 (MH+, 100). Anal. (C25H21N3O6.0.75H2O) C, H, N.

후처리

  1. extractionextracted with chloroform (200 mL)
  2. washThe organic layer was washed with water (7×200 mL)
  3. concentrationconcentrated
  4. additionBenzene was added (2×30 mL)
  5. concentrationthe mixture was concentrated again
  6. dissolutionThe residue was dissolved in chloroform (4 mL)
  7. additiondiethyl ether (50 mL) was added
  8. washThe precipitate was washed with diethyl ether (100 mL)

출처 및 근거

ORD 기록
ord-06f8fb0b9afa416b807ae4e0d83cbc0f
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09388211B2

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