Pyrazol-3-ylamine → N-{3-Chloro-4-[(6,7-dimethoxy-4-quinolyl)-oxy]phenyl}-N'-(1H-5-pyrazolyl)urea

HRID 2416027Notes

Reaction equation

HRID 2416027 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]=[CH:12][CH:11]=1)[NH2:5].C(N(CC)C(C)C)(C)C.ClC(Cl)(O[C:37](=[O:43])OC(Cl)(Cl)Cl)Cl.[NH:45]1[C:49]([NH2:50])=[CH:48][CH:47]=[N:46]1.C(=O)([O-])O.[Na+]>ClC1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:37]([NH:50][C:49]2[NH:45][N:46]=[CH:47][CH:48]=2)=[O:43])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]=[CH:12][CH:11]=1

Participants

7

Reactant 5

HCID 74561Pyrazol-3-ylamineHCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 117390273-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]aniline

Product 1

HCID 22637138N-{3-Chloro-4-[(6,7-dimethoxy-4-quinolyl)-oxy]phenyl}-N'-(1H-5-pyrazolyl)ureaYield 4%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent2×

Procedure

3-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]aniline (20 mg) was dissolved in chlorobenzene (2 ml) and N,N-diisopropylethylamine (0.2 ml) to prepare a solution. A solution of triphosgene (18 mg) in chlorobenzene (0.5 ml) was then added to the solution, and the mixture was stirred at room temperature for 30 min. Next, 1H-5-pyrazolamine (10 mg) was added thereto, and the mixture was further stirred at 110° C. overnight. The reaction solution was developed through diatomaceous earth impregnated with a saturated aqueous sodium hydrogencarbonate solution, followed by extraction with chloroform. The solvent in the extract was removed by distillation. The residue was purified by HPLC using chloroform/methanol for development to give the title compound (1 mg, yield 4%).

Workup

  1. stirringthe mixture was further stirred at 110° C. overnight
  2. extractionfollowed by extraction with chloroform
  3. customThe solvent in the extract was removed by distillation
  4. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-90762b6a96d24cc68ba5c9890541c350
Source dataset
uspto-grants-2004_11
Patent number
US06821987B2

Reaction notes

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