2,4-Dichloro-5-methoxyaniline → 4-[(2,4-Dichloro-5-methoxyphenyl)amino]-7-fluoro-6-(2-morpholin-4-ylethoxy)-3-quinolinecarbonitrile

HRID 1837345Notes

Reaction equation

HRID 1837345 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:21])=[C:9]([O:12][CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:22]#[N:23].[Cl:24][C:25]1[CH:31]=[C:30]([Cl:32])[C:29]([O:33][CH3:34])=[CH:28][C:26]=1[NH2:27].Cl.N1C=CC=CC=1>>[Cl:24][C:25]1[CH:31]=[C:30]([Cl:32])[C:29]([O:33][CH3:34])=[CH:28][C:26]=1[NH:27][C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:21])=[C:9]([O:12][CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:22]#[N:23]

Participants

4

Reactant 3

HCID 14766362,4-Dichloro-5-methoxyanilineHCID 10176127Pyridinium chlorideHCID 234980934-Chloro-7-fluoro-6-[2-(4-morpholinyl)ethoxy]-3-quinolinecarbonitrile

Product 1

HCID 234981014-[(2,4-Dichloro-5-methoxyphenyl)amino]-7-fluoro-6-(2-morpholin-4-ylethoxy)-3-quinolinecarbonitrile

Procedure

Following the procedure of Reference Example 8, a mixture of 4-chloro-7-fluoro-6-(2-morpholin-4-ylethoxy)-3-quinolinecarbonitrile (136 mg, 0.41 mmol), 2,4-dichloro-5-methoxyaniline (90.5 mg, 0.47 mmol) and pyridine hydrochloride (95 mg, 0.82 mmol) provides, after preparative thin layer chromatography eluting with 7% methanol in dichloromethane, 58 mg of 4-[(2,4-dichloro-5-methoxyphenyl)amino]-7-fluoro-6-(2-morpholin-4-ylethoxy)-3-quinolinecarbonitrile, mp 166-168° C.

Workup

  1. customprovides
  2. washafter preparative thin layer chromatography eluting with 7% methanol in dichloromethane, 58 mg of 4-[(2,4-dichloro-5-methoxyphenyl)amino]-7-fluoro-6-(2-morpholin-4-ylethoxy)-3-quinolinecarbonitrile, mp 166-168° C.

Sources & evidence

ORD record
ord-2a564c0ef419407a99b1c7c60c18d3de
Source dataset
uspto-grants-2004_08
Patent number
US06780996B2

Reaction notes

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