4-Chloro-2-fluoroaniline → N-(4-chloro-2-fluorophenyl)-6-methoxy-7-(2-methoxyethoxy)cinnolin-4-amine

HRID 7467

Reaction equation

HRID 7467 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][O:17][CH3:18])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[N:4][CH:3]=1.[Cl:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[C:22]([F:27])[CH:21]=1>CN(C=O)C>[Cl:19][C:20]1[CH:26]=[CH:25][C:23]([NH:24][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][O:17][CH3:18])=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[N:4][CH:3]=2)=[C:22]([F:27])[CH:21]=1

Participants

4

Reactant 2

HCID 938984-Chloro-2-fluoroanilineHCID 107070484-Chloro-6-methoxy-7-(2-methoxyethoxy)cinnoline

Product 1

HCID 6326408N-(4-chloro-2-fluorophenyl)-6-methoxy-7-(2-methoxyethoxy)cinnolin-4-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-chloro-6-methoxy-7-(2-methoxyethoxy)cinnoline (0.4 g, 1.5 mmol), (prepared as described for the starting material in Example 2), and 4-chloro-2-fluoroaniline (282 μl, 2.5 mmol) in DMF (5 ml) was treated as described in Example 2, to give 4-(4-chloro-2-fluoroanilino)-6-methoxy-7-(2-methoxyethoxy)cinnoline as the hydrochloride salt (450 mg, 72%).

Workup

  1. additionwas treated

Sources & evidence

ORD record
ord-a7456a49a4744a4b88f2eea3063a6601
Source dataset
uspto-grants-2006_08
Patent number
US07087602B2

Linked notes

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