4-Chloro-7-(2-chloroethoxy)-6-methoxy-3-quinolinecarbonitrile → Pyridinium chloride

HRID 269762Notes

Reaction equation

HRID 269762 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][Cl:17])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:18]#[N:19].[Cl:20][C:21]1[CH:22]=[C:23]([NH2:34])[CH:24]=[CH:25][C:26]=1[S:27][C:28]1[N:29]([CH3:33])[CH:30]=[CH:31][N:32]=1>C(OCCO)C>[ClH:1].[N:5]1[CH:6]=[CH:11][CH:2]=[CH:3][CH:4]=1.[Cl:17][CH2:16][CH2:15][O:14][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:34][C:23]3[CH:24]=[CH:25][C:26]([S:27][C:28]4[N:29]([CH3:33])[CH:30]=[CH:31][N:32]=4)=[C:21]([Cl:20])[CH:22]=3)=[C:3]([C:18]#[N:19])[CH:4]=[N:5]2)=[CH:10][C:9]=1[O:12][CH3:13]

Participants

5

Reactant 2

HCID 111092524-Chloro-7-(2-chloroethoxy)-6-methoxy-3-quinolinecarbonitrileHCID 114590883-chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)phenylamine

Product 2

HCID 10176127Pyridinium chlorideHCID 684582127-(2-chloroethoxy)-4-{3-chloro-4-[(1-methyl-1H-imidazole-2-yl)sulfanyl]anilino]-6-methoxy-3-quinolinecarbonitrile

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

Following the procedure of Example 9, 1.0 g (3.36 mmol) of 4-chloro-7-(2-chloroethoxy)-6-methoxy-3-quinolinecarbonitrile (Boschelli, Diane H.; Ye, Fei; Wang, Yanong D.; Dutia, Minu; Johnson, Steve L.; Wu, Biqi; Miller, Karen; Powell, Dennis W.; Yaczko, Deanna; Young, Mairead; Tischler, Mark; Arndt, Kim; Discafani, Carolyn; Etienne, Carlo; Gibbons, Jay; Grod, Janet; Lucas, Judy; Weber, Jennifer M.; Boschelli, Frank. J. Med. Chem. 2001, 44, 3965-3977) is reacted with 0.9 g (3.7 mmol) of 3-chloro-4-(1-methyl-1H-imidazole-2-ylsulfanyl)phenylamine (U.S. Pat. No. 4,973,599) and 0.4 g (3.46 mmol) of pyridine hydrochloride in 2-ethoxyethanol (10 mL) to provide 1.44 g of 7-(2-chloroethoxy)-4-{3-chloro-4-[(1-methyl-1H-imidazole-2-yl)sulfanyl]anilino}-6-methoxy-3-quinolinecarbonitrile as a tan solid, mp 278-280° C.

Sources & evidence

ORD record
ord-308e438242904cc99c5c7af2cd330546
Source dataset
uspto-grants-2008_11
Patent number
US07449460B2

Reaction notes

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