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

HRID 1925345Notes

Reaction equation

HRID 1925345 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-813b94087f064b7abf62e243da2a15fe
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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