1,3,4-Thiadiazole, 2-amino-5-methyl- → N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-3-methylphenyl}-N'-(5-methyl-1,3,4-thiadiazol-2-yl)urea

HRID 1348864Notes

Reaction equation

HRID 1348864 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[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][C:17]=1[CH3:23].C(N(C(C)C)CC)(C)C.ClC(Cl)(O[C:37](=[O:43])OC(Cl)(Cl)Cl)Cl.[NH2:45][C:46]1[S:47][C:48]([CH3:51])=[N:49][N:50]=1>C(Cl)(Cl)Cl.O>[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[CH:22]=[CH:21][C:19]([NH:20][C:37]([NH:45][C:46]2[S:47][C:48]([CH3:51])=[N:49][N:50]=2)=[O:43])=[CH:18][C:17]=1[CH3:23]

Participants

7

Reactant 4

HCID 669491,3,4-Thiadiazole, 2-amino-5-methyl-HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 218911624-[(6,7-Dimethoxy-4-quinolyl)oxy]-3-methyl-aniline

Product 1

HCID 23118613N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-3-methylphenyl}-N'-(5-methyl-1,3,4-thiadiazol-2-yl)ureaYield 39.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-3-methylaniline (100 mg) was dissolved in chloroform (5 ml) and diisopropylethylamine (0.5 ml) to prepare a solution. A solution of triphosgene (100 mg) in chloroform was then added to the solution, and the mixture was stirred at room temperature for 15 min. Next, 2-amino-5-methyl-1,3,4-thiadiazole (49 mg) was added thereto, and the mixture was further stirred at room temperature overnight. Distilled water was added to the reaction solution, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine and was dried over sodium sulfate. The organic layer was concentrated under the reduced pressure, and the residue was purified by HPLC using chloroform/acetone for development to give 58 mg of the title compound.

Workup

  1. stirringthe mixture was further stirred at room temperature overnight
  2. extractionthe mixture was subjected to separatory extraction with chloroform
  3. washThe organic layer was washed with saturated brine
  4. dry with materialwas dried over sodium sulfate
  5. concentrationThe organic layer was concentrated under the reduced pressure
  6. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-f1130a4f061c4121b553f2b2fc523273
Source dataset
uspto-grants-2007_05
Patent number
US07211587B2

Reaction notes

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