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

HRID 606110Notes

Reaction equation

HRID 606110 reaction equation
[C:1](OCC)(OCC)(OCC)[CH3:2].[Cl:12][C:13]1[C:22]([NH2:23])=[C:21]([NH:24][CH2:25][C:26]2[O:30][N:29]=[C:28]([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)[CH:27]=2)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1>Cl.N1C=CC=CC=1.C1(C)C=CC=CC=1>[Cl:12][C:13]1[C:22]2[N:23]=[C:1]([CH3:2])[N:24]([CH2:25][C:26]3[O:30][N:29]=[C:28]([C:31]4[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=4)[CH:27]=3)[C:21]=2[C:20]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N:14]=1

Participants

5

Reactant 2

HCID 66221Triethyl orthoacetateHCID 866168902-chloro-N4-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}quinoline-3,4-diamine

Product 1

HCID 866168934-chloro-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-2-methyl-1H-imidazo[4,5-c]quinolineYield 61.8%

Reagents, catalysts & solvents 2

HCID 10176127Pyridinium chlorideCatalystHCID 1140TolueneSolvent

Procedure

Pyridine hydrochloride (0.020 g, 0.19 mmol), triethyl orthoacetate (2.3 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 treated according to the method of Part A of Example 26 to provide 2.307 g of 4-chloro-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-2-methyl-1H-imidazo[4,5-c]quinoline as a pale yellow solid.

Workup

  1. additiontreated

Sources & evidence

ORD record
ord-2d428afe10a34bdf9356b510327cc06f
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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