Toluene → HCID 21890679, compound

HRID 721827Notes

Reaction equation

HRID 721827 reaction equation
N1(C(Cl)=O)CCCC1.[N:9]1([C:14]([N:16]=[C:17]=[S:18])=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10]1.[Cl:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][C:26]=1[O:27][C:28]1[C:37]2[C:32](=[CH:33][C:34]([O:40][CH3:41])=[C:35]([O:38][CH3:39])[CH:36]=2)[N:31]=[CH:30][CH:29]=1)[NH2:23].C1(C)C=CC=CC=1>C(O)C>[N:9]1([C:14]([N:16]=[C:17]=[S:18])=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10]1.[Cl:19][C:20]1[CH:21]=[C:22]([NH:23][C:17]([NH:16][C:14]([N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:15])=[S:18])[CH:24]=[CH:25][C:26]=1[O:27][C:28]1[C:37]2[C:32](=[CH:33][C:34]([O:40][CH3:41])=[C:35]([O:38][CH3:39])[CH:36]=2)[N:31]=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 709371-Pyrrolidinecarbonyl chlorideHCID 117390273-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]anilineHCID 13441035HCID 13441035, compound

Product 2

HCID 13441035HCID 13441035, compoundHCID 21890679HCID 21890679, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1-Pyrrolidinecarbonyl isothiocyanate was prepared using commercially available 1-pyrrolidinecarbonyl chloride (80 mg) as a starting compound according to the description of the literature. 1-Pyrrolidinecarbonyl isothiocyanate was dissolved in ethanol (1 ml) to prepare a solution. 3-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]aniline (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 (52 mg, yield 70%).

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-8ccaae227fed489da66c63fb0bb428b8
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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