Hydrochloric Acid → HCID 86595760, compound

HRID 1765554Notes

Reaction equation

HRID 1765554 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][CH:22]1[C:27]2=[C:28]3[C:33](=[CH:34][CH:35]=[C:26]2[O:25][CH2:24][CH:23]1[NH2:36])[N:32]=[CH:31][CH:30]=[CH:29]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][CH:22]1[C:27]2=[C:28]3[C:33](=[CH:34][CH:35]=[C:26]2[O:25][CH2:24][CH:23]1[NH2:36])[N:32]=[CH:31][CH:30]=[CH:29]3

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 962WaterHCID 10953452Ether hydrochlorideHCID 86595761HCID 86595761, compound

Product 1

HCID 86595760HCID 86595760, 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) (0.42 g, 2.1 mmol), 3-(2-bromoethyl)-5-fluoro-1H-indole (0.39 g, 1.60 mmol), and triethylamine (0.22 mL, 3.20 mmol) in anhydrous dimethylsulfoxide (20 ml) was stirred at 100° C. for 9 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 (2% MeOH/CH2Cl2) afforded 0.22 g (38%) 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-[2-(5-fluoro-1H-indol-3-yl)ethyl-2,3-dihydro-1H-pyrano[3,2-f]quinolin-2-amine bis-hydrochloride salt as a green solid: mp 91° C./dec. MS ESI m/z 362 [M+H]+. Elemental analysis for C22H20FN3O·2.00 HCl.1.50 H2O; Calculated: C, 57.27; H, 5.46; N, 9.11. Found: C, 57.53; H, 5.29; N, 8.64.

Sources & evidence

ORD record
ord-561a04071ed644cb81d4edc703d51daa
Source dataset
uspto-grants-2007_06
Patent number
US07227023B2

Reaction notes

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