Toluene → N-[10,11-Dihydro-5H-dibenzo(b,f)azepin-5-ylcarbonyl]-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}thiourea

HRID 721823Notes

Reaction equation

HRID 721823 reaction equation
C1C2CCC3C=CC=CC=3N(C(Cl)=O)C=2C=CC=1.[CH:19]1[C:29]2[CH2:28][CH2:27][C:26]3[CH:30]=[CH:31][CH:32]=[CH:33][C:25]=3[N:24]([C:34]([N:36]=[C:37]=[S:38])=[O:35])[C:23]=2[CH:22]=[CH:21][CH:20]=1.[CH3:39][O:40][C:41]1[CH:42]=[C:43]2[C:48](=[CH:49][C:50]=1[O:51][CH3:52])[N:47]=[CH:46][CH:45]=[C:44]2[O:53][C:54]1[CH:60]=[CH:59][C:57]([NH2:58])=[CH:56][C:55]=1F.C1(C)C=CC=CC=1>C(O)C>[CH:19]1[C:29]2[CH2:28][CH2:27][C:26]3[CH:30]=[CH:31][CH:32]=[CH:33][C:25]=3[N:24]([C:34]([N:36]=[C:37]=[S:38])=[O:35])[C:23]=2[CH:22]=[CH:21][CH:20]=1.[CH:19]1[C:29]2[CH2:28][CH2:27][C:26]3[CH:30]=[CH:31][CH:32]=[CH:33][C:25]=3[N:24]([C:34]([NH:36][C:37]([NH:58][C:57]3[CH:59]=[CH:60][C:54]([O:53][C:44]4[C:43]5[C:48](=[CH:49][C:50]([O:51][CH3:52])=[C:41]([O:40][CH3:39])[CH:42]=5)[N:47]=[CH:46][CH:45]=4)=[CH:55][CH:56]=3)=[S:38])=[O:35])[C:23]=2[CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 11857910,11-Dihydro-5H-dibenz[b,f]azepine-5-carbonyl chlorideHCID 114269974-((6,7-Dimethoxyquinolin-4-yl)oxy)-3-fluorobenzenamineHCID 2189113510,11-Dihydro-5H-dibenzo(b,f)azepine-5-carbonyl isothiocyanate

Product 2

HCID 21890791N-[10,11-Dihydro-5H-dibenzo(b,f)azepin-5-ylcarbonyl]-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}thioureaYield 65%HCID 2189113510,11-Dihydro-5H-dibenzo(b,f)azepine-5-carbonyl isothiocyanate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

10,11-Dihydro-5H-dibenzo(b,f)azepine-5-carbonyl isothiocyanate was prepared using commercially available 10,11-dihydro-5H-dibenzo(b,f)azepine-5-carbonyl chloride (80 mg) as a starting compound according to the description of the literature. 10,11-Dihydro-5H-dibenzo(b,f)azepine-5-carbonyl isothiocyanate was dissolved in ethanol (1 ml) to prepare a solution. 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-3-fluoroaniline (50 mg), toluene (5 ml), and ethanol (1 ml) were added to the solution, and the mixture was stirred at room temperature for 2 hr. The reaction solution was concentrated, and the residue was purified by chromatography on silica gel using chloroform/acetone for development to give the title compound (61 mg, yield 65%).

Workup

  1. customto prepare a solution
  2. concentrationThe reaction solution was concentrated
  3. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-77df02d54ca746f28e50f7282c74d71a
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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