7-Aminoquinoline → 4-(2-Methylpyrid-4-yl)-N-quinolin-7-yl-benzamide

HRID 494268Notes

Reaction equation

HRID 494268 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[CH3:12][C:13]1[CH:18]=[C:17]([C:19]2[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=2)[CH:16]=[CH:15][N:14]=1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:12][C:13]1[CH:18]=[C:17]([C:19]2[CH:27]=[CH:26][C:22]([C:23]([NH:1][C:2]3[CH:11]=[C:10]4[C:5]([CH:6]=[CH:7][CH:8]=[N:9]4)=[CH:4][CH:3]=3)=[O:24])=[CH:21][CH:20]=2)[CH:16]=[CH:15][N:14]=1

Participants

6

Reactant 3

HCID 113777-AminoquinolineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 186177484-(2-Methylpyridin-4-yl)benzoic acid

Product 1

HCID 576826614-(2-Methylpyrid-4-yl)-N-quinolin-7-yl-benzamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-aminoquinoline (D55) (338 mg, 0.26 mmol) in DCM (3 ml) was added 4-(2-methylpyrid-4-yl)-benzoic acid (D72) (62 mg, 0.29 mmol), 1-(3-dimethylamino-propyl)-3-ethyl-carbodiimide hydrochloride (74 mg, 0.39 mmol) and 4-dimethylaminopyridine (6 mg, 0.05 mmol) and the reaction stirred at room temperature until complete by tlc. The resultant precipitate was filtered off to give the title compound as an off-white solid. MS(ES): MH+ 340, M-H+ 338

Workup

  1. filtrationThe resultant precipitate was filtered off

Sources & evidence

ORD record
ord-ccc5117e17fb44eeb8d9f511de4b310b
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Reaction notes

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