Potassium Carbonate → HCID 58851551, compound

HRID 1696463Notes

Reaction equation

HRID 1696463 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:15]=2[Cl:21])=[O:12])[N:7]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][CH2:29][NH:30]C(=O)C(F)(F)F)[CH:23]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+]>CO.O>[NH2:30][CH2:29][CH2:28][C:24]1[CH:23]=[C:22]([N:7]2[C:8]([NH:10][C:11]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:15]=3[Cl:21])=[O:12])=[CH:9][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[N:6]2)[CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 58011043HCID 58011043, compound

Product 1

HCID 58851551HCID 58851551, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
62.5 °C

Procedure

To a stirring solution of 1-(3-t-butyl-1-(3-(2-(2,2,2-trifluoro-acetamido)ethyl)phenyl)-1 H-pyrazol-5-yl)-3-(2,3-dichloro-phenyl)urea (0.134 g, 0.264 mmol) in MeOH (10 mL) and H2O (0.6 mL) at RT was added K2CO3 (0.182 g, 1.32 mmol). The resulting suspension was stirred at 60-65° C. for 2 h, then cooled to RT and the volatiles evaporated. The residue was carefully dissolved in 1N HCl to pH 1-2 and extracted with Et2O (2×). The aqueous was then basified (pH 13-14) with 3M NaOH and extracted with CH2Cl2 (4×). The combined CH2Cl2 extracts were washed with brine (1×), dried (Na2SO4), filtered, and concentrated to provided 1-{1-[3-(2-aminoethyl)phenyl]-3-t-butyl-1H-pyrazol-5-yl}-3-(2,3-dichlorophenyl)urea as a foam (25.6 mg, 97% yield). 1H NMR (400 MHz, CDCl3): δ 8.17 (dd, J=1.2, and 8.0 Hz, 1H), 7.31-7.28 (m, 4H), 7.14-7.06 (m, 4H), 6.45 (s, 1H), 3.48 (brt, J=4.4 Hz, 2H), 3.46-3.39 (m, 2H), 2.86 (t, J=7.0 Hz, 2H), 1.3 (s, 9H); MS (ESI) m/z: 446.3 (M+H+).

Workup

  1. temperaturecooled to RT
  2. customthe volatiles evaporated
  3. dissolutionThe residue was carefully dissolved in 1N HCl to pH 1-2
  4. extractionextracted with Et2O (2×)
  5. extractionextracted with CH2Cl2 (4×)
  6. washThe combined CH2Cl2 extracts were washed with brine (1×)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-d771aff4e258411d99b8d5a2c90b6003
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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