3-(Dimethylamino)-1-propanol → 4-({3-chloro-4-[(1-methyl-1H-imidazol-2-yl)sulfanyl]phenyl}amino)-7-[3-(dimethylamino)propoxy]-6-(2-methoxyethoxy)-3-quinolinecarbonitrile

HRID 1837365Notes

Reaction equation

HRID 1837365 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:15][C:16]2[C:25]3[C:20](=[CH:21][C:22](F)=[C:23]([O:26][CH2:27][CH2:28][O:29][CH3:30])[CH:24]=3)[N:19]=[CH:18][C:17]=2[C:32]#[N:33])[CH:5]=[CH:6][C:7]=1[S:8][C:9]1[N:10]([CH3:14])[CH:11]=[CH:12][N:13]=1.[CH3:34][N:35]([CH3:40])[CH2:36][CH2:37][CH2:38][OH:39]>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:15][C:16]2[C:25]3[C:20](=[CH:21][C:22]([O:39][CH2:38][CH2:37][CH2:36][N:35]([CH3:40])[CH3:34])=[C:23]([O:26][CH2:27][CH2:28][O:29][CH3:30])[CH:24]=3)[N:19]=[CH:18][C:17]=2[C:32]#[N:33])[CH:5]=[CH:6][C:7]=1[S:8][C:9]1[N:10]([CH3:14])[CH:11]=[CH:12][N:13]=1

Participants

3

Reactant 2

HCID 766463-(Dimethylamino)-1-propanolHCID 234980784-({3-chloro-4-[(1-methyl-1H-imidazol-2-yl)sulfanyl]phenyl}amino)-7-fluoro-6-(2-methoxyethoxy)-3-quinolinecarbonitrile

Product 1

HCID 99854164-({3-chloro-4-[(1-methyl-1H-imidazol-2-yl)sulfanyl]phenyl}amino)-7-[3-(dimethylamino)propoxy]-6-(2-methoxyethoxy)-3-quinolinecarbonitrile

Procedure

Following the procedure of Example 19, 4-({3-chloro-4-[(1-methyl-1H-imidazol-2-yl)sulfanyl]phenyl}amino)-7-fluoro-6-(2-methoxyethoxy)-3-quinolinecarbonitrile (300 mg, 0.62 mmol) and 2 mL of 3-dimethylamino-1-propanol provides 115 mg of 4-({3-chloro-4-[(1-methyl-1H-imidazol-2-yl)sulfanyl]phenyl}amino)-7-[3-(dimethylamino)propoxy]-6-(2-methoxyethoxy)-3-quinolinecarbonitrile, mp 194-203° C.

Sources & evidence

ORD record
ord-c10fee4c179f49549d58d24014f80ca8
Source dataset
uspto-grants-2004_08
Patent number
US06780996B2

Reaction notes

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