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

HRID 387853Notes

Reaction equation

HRID 387853 reaction equation
[CH2:1]([N:3]([CH2:27]C)[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12]([S:18][C:19]3[S:23][C:22]([NH2:24])=[CH:21][CH:20]=3)=[CH:13][CH:14]=[N:15]2)=[CH:10][C:9]=1[O:25][CH3:26])C.[F:29][C:30]1[CH:35]=[CH:34][C:33]([N:36]=[C:37]=[O:38])=[CH:32][CH:31]=1>O1CCCC1>[CH3:27][N:3]([CH3:1])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12]([S:18][C:19]3[S:23][C:22]([NH:24][C:37]([NH:36][C:33]4[CH:34]=[CH:35][C:30]([F:29])=[CH:31][CH:32]=4)=[O:38])=[CH:21][CH:20]=3)=[CH:13][CH:14]=[N:15]2)=[CH:10][C:9]=1[O:25][CH3:26]

Participants

4

Reactant 2

HCID 709554-Fluorophenyl isocyanateHCID 589308085-({7-[3-(Diethylamino)propoxy]-6-methoxy-4-quinolyl}sulfanyl)-2-thiopheneamine

Product 1

HCID 67202083N1-[5-({7-[3-(Dimethylamino)propoxy]-6-methoxy-4-quinolyl}sulfanyl)-2-thienyl]-N'-(4-fluorophenyl)ureaYield 6.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-({7-[3-(Diethylamino)propoxy]-6-methoxy-4-quinolyl}sulfanyl)-2-thiophenylamine (190 mg), parafluorophenyl 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-37967c42f7a34e688b8c9150ac24bbb8
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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