Glycol monoethyl ether → 4-(3-Bromo-phenylamino)-6-methoxy-7-(3-morpholin-4-yl-propoxy)-quinoline-3-carbonitrile

HRID 1935124Notes

Reaction equation

HRID 1935124 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:24]#[N:25].[Br:26][C:27]1[CH:28]=[C:29]([CH:31]=[CH:32][CH:33]=1)[NH2:30].Cl.N1C=CC=CC=1.C(OCCO)C>>[Br:26][C:27]1[CH:28]=[C:29]([NH:30][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:24]#[N:25])[CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 4

HCID 8076Glycol monoethyl etherHCID 115623-BromoanilineHCID 10176127Pyridinium chlorideHCID 224666014-Chloro-6-methoxy-7-(3-morpholinopropoxy)quinoline-3-carbonitrile

Product 1

HCID 224666084-(3-Bromo-phenylamino)-6-methoxy-7-(3-morpholin-4-yl-propoxy)-quinoline-3-carbonitrile

Procedure

The method of Example 312 was used as well as 0.3 g of 4-chloro-6-methoxy-7-(3-morpholin-4-yl-propoxy)-quinoline-3-carbonitrile, 0.12 ml of 3-bromo aniline, 0.1 g of pyridine hydrochloride and 4.0 ml of 2-ethoxy ethanol. This afforded an oil which was purified by silica gel flash chromatography utilizing a gradient of methylene chloride/methanol (96:4 to 92:8) to give 0.22 g of the title compound as an off white solid,mp 115-118 C; mass spectrum (ES,m/e): M+H499.

Workup

  1. customThis afforded an oil which
  2. customwas purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-3618143dea0e4b30b0bf1a6b7da9247c
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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