Glycol monoethyl ether → 4-({3-chloro-4-[(1-methyl-1H-imidazole-2-yl)sulfanyl]phenyl}amino)-6-ethoxy-7-fluoro-3-quinolinecarbonitrile

HRID 499109Notes

Reaction equation

HRID 499109 reaction equation
Cl[C:2]1(OCC)[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]1[C:13]#[N:14].[Cl:18][C:19]1[CH:20]=[C:21]([NH2:32])[CH:22]=[CH:23][C:24]=1[S:25][C:26]1[N:27]([CH3:31])[CH:28]=[CH:29][N:30]=1.Cl.N1C=CC=CC=1.[CH2:40]([O:42]CCO)[CH3:41]>>[Cl:18][C:19]1[CH:20]=[C:21]([NH:32][C:2]2[C:11]3[C:6](=[CH:7][C:8]([F:12])=[C:9]([O:42][CH2:40][CH3:41])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:13]#[N:14])[CH:22]=[CH:23][C:24]=1[S:25][C:26]1[N:27]([CH3:31])[CH:28]=[CH:29][N:30]=1

Participants

5

Reactant 4

HCID 8076Glycol monoethyl etherHCID 10176127Pyridinium chlorideHCID 114590883-chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)phenylamineHCID 684605564-Chloro-4-ethoxy-7-fluoro-3-quinolinecarbonitrile

Product 1

HCID 684586754-({3-chloro-4-[(1-methyl-1H-imidazole-2-yl)sulfanyl]phenyl}amino)-6-ethoxy-7-fluoro-3-quinolinecarbonitrile

Procedure

Following the procedure of Example 1, a mixture of 2.4 g (9.72 mmol) 4-chloro-4-ethoxy-7-fluoro-3-quinolinecarbonitrile, 2.56 g (10.7 mmol) of 3-chloro-4-(1-methyl-1H-imidazole-2-ylsulfanyl)phenylamine and 1.2 g (10.38 mmol) of pyridine hydrochloride are refluxed in 2-ethoxyethanol (30 mL) at 110° C. for 1 hour to yield 4-({3-chloro-4-[(1-methyl-1H-imidazole-2-yl)sulfanyl]phenyl}amino)-6-ethoxy-7-fluoro-3-quinolinecarbonitrile as a pink solid, mp 251-254° C.

Sources & evidence

ORD record
ord-9ca14b91468345d188e30163013aaacb
Source dataset
uspto-grants-2010_08
Patent number
US07767671B2

Reaction notes

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