ChemicalBook CAS DataBase List 5H-Indeno[1,2-c]isoquinoline-9-sulfonaMide, 6,11-dihydro-N-[3-(4-Morpholinyl)propyl]-5-oxo-

5H-Indeno[1,2-c]isoquinoline-9-sulfonaMide, 6,11-dihydro-N-[3-(4-Morpholinyl)propyl]-5-oxo- synthesis

6synthesis methods

Product Name:5H-Indeno[1,2-c]isoquinoline-9-sulfonaMide, 6,11-dihydro-N-[3-(4-Morpholinyl)propyl]-5-oxo-
CAS Number:501364-82-5
Molecular formula:C23H25N3O4S
Molecular Weight:439.53

Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

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5H-Indeno[1,2-c]isoquinoline-9-sulfonaMide, 6,11-dihydro-N-[3-(4-Morpholinyl)propyl]-5-oxo-

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Yield: 44%

Reaction Conditions:

Stage #1:4-(3-Aminopropyl)morpholine with sodium hydrogencarbonate in water;ethyl acetate for 0.25 h;
Stage #2:9-chlorosulfonyl-5,6-dihydro-5-oxo-indeno[1,2-c]isoquinoline in water;ethyl acetate at 20; for 24 h;Product distribution / selectivity;

Steps:

1.7; 6.1.h.I
To a stirred suspension of 3-(4-morpholino)-1-propylamine (17. 28 g, 0.12 mol) in EtOAc was added sat. aq. NaHCO3 (300 mL), and the mixture was allowed to stir for 15 min. Compound 7 (4.0 g, 0.012 mol) was then introduced in small portions at room temperature. The reaction mixture was stirred for 24 h; filtered and washed with H2O, EtOAc and MeOH ; refluxed in MeOH for 30 min ; filtered while still warm; and washed with MeOH to provide compound 81 as a free base (2.33 g, 44 %).'H NMR (DMSO-d6): 81. 47-1.52 (m, 2H), 2.16-2. 21 (m, 4H), 2.47-2. 48 (m, 2H), 3.44-3. 48 (m, 2H), 3.23 (m, 4H), 4.02 (s, 2H), 7.49-7. 58 (m, lH), 7.78-7. 82 (m, 3H), 7.97 (s, 1H), 8.14 (d, J= 7. 8 Hz, 1H), 8.26 (d, J = 7.8 Hz, 1H), 9.59 (s, 1H), 12.42 (s, 1H).

References:

INOTEK PHARMACEUTICALS CORPORATION WO2005/82368, 2005, A1 Location in patent:Page/Page column 60; 86-87

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123-00-2 Synthesis