4-Fluorophenyl isocyanate → N1-[5-({7-[3-(Dimethylamino)propoxy]-6-methoxy-4-quinolyl}sulfanyl)-2-thienyl]-N'-(4-fluorophenyl)urea

HRID 853376Notes

Reaction equation

HRID 853376 reaction equation
[CH3:1][N:2]([CH3:26])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11]([S:17][C:18]3[S:22][C:21]([NH2:23])=[CH:20][CH:19]=3)=[CH:12][CH:13]=[N:14]2)=[CH:9][C:8]=1[O:24][CH3:25].[F:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]=[C:35]=[O:36])=[CH:30][CH:29]=1>O1CCCC1>[CH3:26][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11]([S:17][C:18]3[S:22][C:21]([NH:23][C:35]([NH:34][C:31]4[CH:32]=[CH:33][C:28]([F:27])=[CH:29][CH:30]=4)=[O:36])=[CH:20][CH:19]=3)=[CH:12][CH:13]=[N:14]2)=[CH:9][C:8]=1[O:24][CH3:25]

Participants

4

Reactant 2

HCID 709554-Fluorophenyl isocyanateHCID 673051175-((7-[3-(Dimethylamino)propoxy]-6-methoxy-4-quinolyl}sulfanyl)-2-thiophenylamine

Product 1

HCID 67202083N1-[5-({7-[3-(Dimethylamino)propoxy]-6-methoxy-4-quinolyl}sulfanyl)-2-thienyl]-N'-(4-fluorophenyl)ureaYield 6.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-({7-[3-(Dimethylamino)propoxy]-6-methoxy-4-quinolyl}sulfanyl)-2-thiophenylamine (190 mg), para-fluorophenyl isocyanate (69 mg) and tetrahydrofuran (30 ml) were stirred together at room temperature for 30 minutes. The organic solvent was distilled off under reduced pressure, and the residue was purified by column chromatography (ethyl acetate, followed by ethyl acetate:methanol=10:1) using NH type silica gel. The solvent was distilled off under reduced pressure, and ethyl acetate was added to the residue for solidification to obtain 16 mg of a yellowish-brown solid.

Workup

  1. distillationThe organic solvent was distilled off under reduced pressure
  2. customthe residue was purified by column chromatography (ethyl acetate, followed by ethyl acetate:methanol=10:1)
  3. distillationThe solvent was distilled off under reduced pressure, and ethyl acetate
  4. additionwas added to the residue for solidification

Sources & evidence

ORD record
ord-483ddd78bfb04a75bc12249b3d5cd452
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Reaction notes

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