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

HRID 606108Notes

Reaction equation

[C:1](OC)(OC)(OC)[CH2:2][CH2:3][CH3:4].[Cl:11][C:12]1[C:21]([NH2:22])=[C:20]([NH:23][CH2:24][C:25]2[O:29][N:28]=[C:27]([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)[CH:26]=2)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1>Cl.N1C=CC=CC=1.C1(C)C=CC=CC=1>[Cl:11][C:12]1[C:21]2[N:22]=[C:1]([CH2:2][CH2:3][CH3:4])[N:23]([CH2:24][C:25]3[O:29][N:28]=[C:27]([C:30]4[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=4)[CH:26]=3)[C:20]=2[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N:13]=1

Participants

Conditions

Temperature: 110 °C

Procedure

Under a nitrogen atmosphere, pyridine hydrochloride (0.020 g, 0.19 mmol), trimethyl orthobutyrate (2.1 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. The volatiles were removed under reduced pressure. The crude product was purified by column chromatography on silica gel (250 g, eluting with 20% to 40% ethyl acetate in hexane) to provide 0.806 g of 4-chloro-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-2-propyl-1H-imidazo[4,5-c]quinoline as a yellow solid.

Workup

customThe volatiles were removed under reduced pressure
customThe crude product was purified by column chromatography on silica gel (250 g, eluting with 20% to 40% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-e01a81e1dd554743a6b751f1769914b5
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915281B2

Reaction notes

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