Hydrochloric Acid → HCID 9799764, compound

HRID 1765551Notes

Reaction equation

HRID 1765551 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][NH:23][CH:24]1[CH2:37][O:36][C:35]2[C:26](=[C:27]3[C:32](=[CH:33][CH:34]=2)[N:31]=[CH:30][CH:29]=[CH:28]3)[CH2:25]1.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][NH:23][CH:24]1[CH2:37][O:36][C:35]2[C:26](=[C:27]3[C:32](=[CH:33][CH:34]=2)[N:31]=[CH:30][CH:29]=[CH:28]3)[CH2:25]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 10953452Ether hydrochlorideHCID 69497608HCID 69497608, compound

Product 1

HCID 9799764HCID 9799764, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2,3-dihydro-1H-pyrano[3,2-f]quinolin-2-amine (intermediate 1a) (0.68 g, 3.4 mmol), 3-(3-bromopropyl)-5-fluoro-1H-indole (0.58 g, 2.26 mmol), and triethylamine (0.63 mL, 4.52 mmol) in anhydrous dimethylsulfoxide (40 mL) was stirred at 80° C. for 12 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 0.54 g (64%) of product as a brown oil. 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-[3-(5-fluoro-1H-indol-3-yl)propyl]-2,3-dihydro-1H-pyrano[3,2-f]quinolin-2-amine bis-hydrochloride salt as a light brown solid: mp>180° C. MS ESI m/z 376 [M+H]+. Elemental Analysis for C23H22FN3O·2.00 HCl·0.25 H2O; Calculated: C, 61.00; H, 5.45; N, 9.28. Found: C, 61.02; H, 5.66; N, 9.03.

Sources & evidence

ORD record
ord-b08d680b94a44267aa6cf916ee61525c
Source dataset
uspto-grants-2007_06
Patent number
US07227023B2

Reaction notes

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