Hydrochloric Acid → HCID 11269280, compound

HRID 1765558Notes

Reaction equation

HRID 1765558 reaction equation
Cl.Cl.CCOCC.Cl.Cl.[F:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[CH2:20][CH2:21][CH2:22][CH2:23][NH:24][CH:25]1[CH2:38][O:37][C:28]2=[C:29]3[C:34](=[CH:35][CH:36]=[C:27]2[CH2:26]1)[N:33]=[CH:32][CH:31]=[CH:30]3.O>C(OCC)(=O)C>[F:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[CH2:20][CH2:21][CH2:22][CH2:23][NH:24][CH:25]1[CH2:38][O:37][C:28]2=[C:29]3[C:34](=[CH:35][CH:36]=[C:27]2[CH2:26]1)[N:33]=[CH:32][CH:31]=[CH:30]3

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 962WaterHCID 10953452Ether hydrochlorideHCID 69497651HCID 69497651, compound

Product 1

HCID 11269280HCID 11269280, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3,4-dihydro-2H-pyrano[2,3-f]quinolin-3-amine (intermediate 1a) (0.20 g, 1.0 mmol), 3-(4-bromobutyl)-5-fluoro-1H-indole (0.19 g, 0.84 mmol), and triethylamine (0.28 mL, 1.68 mmol) in anhydrous dimethylsulfoxide (20 ml) was stirred at 100° C. for 14 hrs. The reaction mixture was poured into ice-H2O and extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. Chromatography (5% MeOH/CH2Cl2) afforded 0.06 g (18%) of product as a light brown oil and unreacted starting material. It was converted to the HCl salt by dissolution in ethyl acetate and addition of 1M HCl/Et2O solution (2.4 eq) to generate N-[4-(5-fluoro-1H-indol-3-yl)butyl]-3,4-dihydro-2H-pyrano[2,3-f]quinolin-3-amine bis-hydrochloride salt as an off-white solid: mp 173° C./dec. MS ESI m/z 390 [M+H]+. Elemental Analysis for C24H24FN3O·2.00 HCl.3.00 H2O; Calculated: C, 55.82; H, 6.25; N, 8.14. Found: C, 55.57; H, 6.06; N, 7.76.

Sources & evidence

ORD record
ord-87f48d14cc7d432eb4f0da05996626a5
Source dataset
uspto-grants-2007_06
Patent number
US07227023B2

Reaction notes

Loading…