Pyrazole → HCID 178486388, compound

HRID 1052142Notes

Reaction equation

HRID 1052142 reaction equation
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

Participants

6

Reactant 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

Product 1

HCID 178486388HCID 178486388, compoundYield 57.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-06f8fb0b9afa416b807ae4e0d83cbc0f
Source dataset
uspto-grants-2016_07
Patent number
US09388211B2

Reaction notes

Loading…