7-Aminoquinoline → HCID 44415654, compound

HRID 494233Notes

Reaction equation

HRID 494233 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.[C:12]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:17]=[CH:16][C:15]([C:18](O)=[O:19])=[CH:14][CH:13]=1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[N:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([NH:1][C:18]([C:15]3[CH:16]=[CH:17][C:12]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)=[CH:13][CH:14]=3)=[O:19])[CH:11]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 113777-AminoquinolineHCID 66724(1,1'-Biphenyl)-4-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 44415654HCID 44415654, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 7-aminoquinoline (D55) (100 mg, 0.69 mmol) in DCM (3 ml) was added 4-biphenylcarboxylic acid (206 mg, 1.04 mmol), 1-(3-dimethylamino-propyl)-3-ethyl-carbodiimide hydrochloride (197 mg, 1.04 mmol) and 4-dimethylaminopyridine (10 mg, 0.08 mmol) and the reaction stirred at room temperature overnight. The mixture was diluted with DCM, washed with sat. aqueous sodium bicarbonate solution, dried over MgSO4 and concentrated in vacuo to give the crude product which was purified by SPE column chromatography. Elution with 50% EtOAc in 40-60° C. petroleum ether gave the title compound as an off-white solid. 1H NMR (400 MHz, CDCl3) δ (ppm): 8.91 (dd, 1H), 8.19 (d, 1H), 8.12 (m, 2H), 8.02, (d, 2H), 7.86 (d, 1H), 7.75 (d, 2H), 7.65 (d, 2H), 7.49 (t, 2H), 7.42 (t, 1H), 7.36 (dd, 1H).

Workup

  1. washwashed with sat. aqueous sodium bicarbonate solution
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customto give the crude product which
  5. customwas purified by SPE column chromatography
  6. washElution with 50% EtOAc in 40-60° C. petroleum ether

Sources & evidence

ORD record
ord-f0743b5440eb42188c0abcb4d36540f3
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Reaction notes

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