1-Pyrrolidineethanamine → N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,5-dimethylphenyl}-N'-[2-(1-pyrrolidinyl)ethyl]thiourea

HRID 721459Notes

Reaction equation

HRID 721459 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[C:22]([CH3:23])=[CH:21][C:19]([NH2:20])=[C:18]([CH3:24])[CH:17]=1.C(N(CC)CC)C.[C:32](Cl)(Cl)=[S:33].[NH2:36][CH2:37][CH2:38][N:39]1[CH2:43][CH2:42][CH2:41][CH2:40]1>CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[C:22]([CH3:23])=[CH:21][C:19]([NH:20][C:32]([NH:36][CH2:37][CH2:38][N:39]2[CH2:43][CH2:42][CH2:41][CH2:40]2)=[S:33])=[C:18]([CH3:24])[CH:17]=1

Participants

7

Reactant 4

HCID 13441-PyrrolidineethanamineHCID 8471TriethylamineHCID 10040ThiophosgeneHCID 218904214-((6,7-Dimethoxyquinolin-4-yl)oxy)-2,5-dimethylaniline

Product 1

HCID 21890755N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,5-dimethylphenyl}-N'-[2-(1-pyrrolidinyl)ethyl]thioureaYield 10.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,5-dimethylaniline (51 mg) was dissolved in N,N-dimethylformamide (2 ml) and triethylamine (1 ml) to prepare a solution. Thiophosgene (51 mg) was then added to the solution, and the mixture was stirred at room temperature for 6 hr. Next, 1-(2-aminoethyl)pyrrolidine (50 mg) was added thereto, and the mixture was further stirred at room temperature for 16 hr. Ethyl acetate was added to the reaction solution, followed by washing with water and saturated brine in that order. The organic layer was then dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by HPLC using chloroform/methanol for development to give the title compound (8 mg, yield 10%).

Workup

  1. stirringthe mixture was further stirred at room temperature for 16 hr
  2. washby washing with water and saturated brine in that order
  3. dry with materialThe organic layer was then dried over anhydrous sodium sulfate
  4. customThe solvent was removed by distillation under the reduced pressure
  5. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-6963fc7f0334446ca8646a6b2fc99a8a
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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