4-[(2,4-Dichloro-5-methoxyphenyl)amino]-7-fluoro-6-methoxy-3-quinolinecarbonitrile → HCID 10029878, compound

HRID 1837372Notes

Reaction equation

HRID 1837372 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH3:10])=[CH:4][C:3]=1[NH:11][C:12]1[C:21]2[C:16](=[CH:17][C:18](F)=[C:19]([O:22][CH3:23])[CH:20]=2)[N:15]=[CH:14][C:13]=1[C:25]#[N:26].[CH3:27][N:28]1[CH2:33][CH2:32][CH:31]([CH2:34][CH2:35][CH2:36][NH2:37])[CH2:30][CH2:29]1>CN1CCCC1=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH3:10])=[CH:4][C:3]=1[NH:11][C:12]1[C:21]2[C:16](=[CH:17][C:18]([NH:37][CH2:36][CH2:35][CH2:34][CH:31]3[CH2:30][CH2:29][N:28]([CH3:27])[CH2:33][CH2:32]3)=[C:19]([O:22][CH3:23])[CH:20]=2)[N:15]=[CH:14][C:13]=1[C:25]#[N:26]

Participants

4

Reactant 2

HCID 114861534-[(2,4-Dichloro-5-methoxyphenyl)amino]-7-fluoro-6-methoxy-3-quinolinecarbonitrileHCID 234980804-Piperidinepropanamine,1-methyl-(9CI)

Product 1

HCID 10029878HCID 10029878, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Following the procedure used to prepare Example 27, 250 mg (0.64 mmol) of 4-[(2,4-dichloro-5-methoxyphenyl)amino]-7-fluoro-6-methoxyquinoline-3-carbonitrile is reacted with 600 mg (3.80 mmol) of 3-(1-methylpiperidin-4-yl)propylamine in 2 mL of 1-methyl-2-pyrrolidinone at 105° C. for 18 hours to yield 130 mg of 4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-7-{[3-(1-methylpiperidin-4-yl)propyl]amino}quinoline-3-carbonitrile as a white solid, mp 122-124° C.

Sources & evidence

ORD record
ord-1c202d140408408e8ef286215b77e320
Source dataset
uspto-grants-2004_08
Patent number
US06780996B2

Reaction notes

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