Ethyl orthopropionate → 4-chloro-2-ethyl-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-1H-imidazo[4,5-c]quinoline

HRID 606106Notes

Reaction equation

[C:1](OCC)(OCC)(OCC)[CH2:2][CH3:3].[Cl:13][C:14]1[C:23]([NH2:24])=[C:22]([NH:25][CH2:26][C:27]2[O:31][N:30]=[C:29]([C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=3)[CH:28]=2)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1>Cl.N1C=CC=CC=1.C1(C)C=CC=CC=1>[Cl:13][C:14]1[C:23]2[N:24]=[C:1]([CH2:2][CH3:3])[N:25]([CH2:26][C:27]3[O:31][N:30]=[C:29]([C:32]4[CH:33]=[CH:34][C:35]([F:38])=[CH:36][CH:37]=4)[CH:28]=3)[C:22]=2[C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:15]=1

Participants

Conditions

Temperature: 110 °C

Procedure

Under a nitrogen atmosphere, pyridine hydrochloride (0.020 g, 0.19 mmol), triethyl orthopropionate (2.5 g, 14 mmol), 2-chloro-N4-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}quinoline-3,4-diamine (3.5 g, 9.5 mmol), and toluene (50 mL) were combined and heated at 110° C. for 18 hours. Most of the volatiles were removed under reduced pressure to provide a suspension. The solid was isolated by filtration, washed with diethyl ether, and dried to provide 2.624 g of 4-chloro-2-ethyl-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-1H-imidazo[4,5-c]quinoline as a tan solid.

Workup

customMost of the volatiles were removed under reduced pressure
customto provide a suspension
customThe solid was isolated by filtration
washwashed with diethyl ether
customdried

Sources & evidence

ORD record: ord-4d3566a0f6eb4e7e9b2f6ace7075bd34
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915281B2

Reaction notes

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