Pyrazol-3-ylamine → HCID 22637128, compound

HRID 2416028Notes

Reaction equation

HRID 2416028 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])=[C:18]([F:23])[CH:17]=1.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>[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:50][C:49]2[NH:45][N:46]=[CH:47][CH:48]=2)=[O:43])=[C:18]([F:23])[CH:17]=1

Participants

7

Reactant 5

HCID 74561Pyrazol-3-ylamineHCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 113014704-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline

Product 1

HCID 22637128HCID 22637128, compoundYield 11.1%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent2×

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline (20 mg) was dissolved in chlorobenzene (1.5 ml) and N,N-diisopropylethylamine (0.15 ml) to prepare a solution. A solution of triphosgene (19 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 100° 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 (3 mg, yield 11%).

Workup

  1. stirringthe mixture was further stirred at 100° 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-98553c953c1b48dc8a6307a5227a9c19
Source dataset
uspto-grants-2004_11
Patent number
US06821987B2

Reaction notes

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