P-Anisidine → N-(6-((6,7-bis(methoxy)-4-quinolinyl)oxy)-1-naphthalenyl)-N'-(4-(methoxy)phenyl)thiourea

HRID 2115843Notes

Reaction equation

HRID 2115843 reaction equation
[N:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8]([O:14][C:15]1[C:24]3[C:19](=[CH:20][C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=3)[N:18]=[CH:17][CH:16]=1)=[CH:9]2)=[C:2]=[S:3].[CH3:29][O:30][C:31]1[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][CH:32]=1>C(Cl)Cl>[CH3:26][O:25][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][C:21]=1[O:27][CH3:28])[N:18]=[CH:17][CH:16]=[C:15]2[O:14][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[C:4]([NH:1][C:2]([NH:35][C:34]1[CH:36]=[CH:37][C:31]([O:30][CH3:29])=[CH:32][CH:33]=1)=[S:3])=[CH:13][CH:12]=[CH:11]2

Participants

4

Reactant 2

HCID 7732P-AnisidineHCID 860623144-(5-Isothiocyanatonaphthalen-2-yloxy)-6,7-dimethoxyquinoline

Product 1

HCID 59813195N-(6-((6,7-bis(methoxy)-4-quinolinyl)oxy)-1-naphthalenyl)-N'-(4-(methoxy)phenyl)thiourea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(5-isothiocyanatonaphthalen-2-yloxy)-6,7-dimethoxyquinoline (27 mg, 0.070 mmol) in DCM (348 μL) at RT was added 4-methoxyaniline (17.2 mg, 0.140 mmol) in one portion. After stirring for 14 h, the crude mixture was concentrated under reduced pressure and purified by silica gel chromatography. MS (ESI, pos. ion) m/z: 512.1. (M+1). Mass Calc'd for C18H15NO3: 511.60.

Workup

  1. concentrationthe crude mixture was concentrated under reduced pressure
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-56369a6364b5415f91ae2be441bfe27d
Source dataset
uspto-grants-2008_10
Patent number
US07435823B2

Reaction notes

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