Methylhydrazine → 1-(4-Chloro-phenyl)-3-[4-hydroxy-3-(2-methyl-2H-pyrazol-3-yl)-phenyl]-urea

HRID 407472Notes

Reaction equation

HRID 407472 reaction equation
[CH3:1][NH:2][NH2:3].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([NH:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[O:21][CH:20]=[CH:19][C:18]3=O)=[O:13])=[CH:7][CH:6]=1>N1C=CC=CC=1>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([NH:14][C:15]2[CH:24]=[CH:23][C:22]([OH:21])=[C:17]([C:18]3[N:2]([CH3:1])[N:3]=[CH:20][CH:19]=3)[CH:16]=2)=[O:13])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 231394541-(4-chloro-phenyl)-3-(4-oxo-4H-chromen-6-yl)-urea

Product 1

HCID 1356979361-(4-Chloro-phenyl)-3-[4-hydroxy-3-(2-methyl-2H-pyrazol-3-yl)-phenyl]-ureaYield 65.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a cooled and stirred solution of methyl hydrazine (1.46 g, 31.6 mmol) in pyridine was added slurry of 1-(4-Chloro-phenyl)-3-(4-oxo-4H-chromen-6-yl)-urea (2.5 g, 7.9 mmol) in pyridine over a period of 10 mins. The reaction mixture was left at this temperature for another 2 hrs and then warmed to room temperature slowly. After 6 hrs the reaction mixture turned clear. The reaction was stirred at this temperature for 18 hrs and pyridine was evaporated. The dark colored residue was dissolved in DMSO and purified using Varian Prep. HPLC system. (The two regioisomers were separated. The fractions containing Compound 119 were dried in vacuo to produce a colorless powder (1.78 g, 47%) 1-(4-Chloro-phenyl)-3-[4-hydroxy-3-(2-methyl-2H-pyrazol-3-yl)-phenyl]-urea. LCMS m/z (%)=343 (M+H, 35Cl 100), 345 (M+H, 37Cl, 32.5). 1H NMR (400 MHz, DMSO-d6) δ: 9.59 (bs, 1H), 8.72 (bs, 1H), 8.48 (bs, 1H), 7.43-7.46 (dd, J=6.8, 2.07 Hz, 2H), 7.41 (d, J=1.83 Hz, 1H), 7.28-7.30 (dd, J=7.13, 2.09 Hz, 2H), 7.26 (d, J=2.72 Hz, 1H), 6.88-6.90 (d, J=9.36 Hz, 1H), 6.21 (d, J=1.84 Hz, 1H), 3.67 (s, 3H).

Workup

  1. temperatureTo a cooled
  2. waitAfter 6 hrs the reaction mixture turned clear
  3. custompyridine was evaporated
  4. dissolutionThe dark colored residue was dissolved in DMSO
  5. custompurified
  6. custom(The two regioisomers were separated
  7. additionThe fractions containing Compound 119
  8. customwere dried in vacuo

Sources & evidence

ORD record
ord-217015b8dccc456da70042bb075ae17e
Source dataset
uspto-grants-2014_06
Patent number
US08754238B2

Reaction notes

Loading…