Hydrochloric Acid → HCID 58851318, compound

HRID 1696566Notes

Reaction equation

HRID 1696566 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][C:29]([NH:31][CH3:32])=O)[CH:23]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].B.C1COCC1.Cl.[OH-].[Na+]>C1COCC1>[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:31][CH3:32])[CH:23]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 58851610HCID 58851610, compound

Product 1

HCID 58851318HCID 58851318, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1-(3-t-butyl-1-(3-(2-(methylamino)-2-oxoethyl)phenyl)-1H-pyrazol-5-yl)-3-(2,3-dichlorophenyl)urea (0.071 g, 0.15 mmol) in THF (2 mL) was added a solution of 1M BH3-THF (1 mL, 1 mmol) at 0° C. under Ar. After stirring the mixtureat 60° C. for 24 h, it was cooled to 0° C., and 3M HCl was added slowly. The mixture was heated to 60° C. for 30 min, cooled to 0° C., and basified with 20% NaOH solution. The product was extracted with CHCl3 (3×25 mL). The combined organic extracts were washed with H2O (1×30 mL), brine, dried (Na2SO4) and concentrated. The resultant residue was dissolved in CH2Cl2 (2 mL) and 3M HCl/EtOAc solution (1 mL) was added and stirred for 10 min to yield (0.025 g, 36%) 1-(3-t-butyl-1-(3-(2-(methylamino)ethyl)phenyl)-1H-pyrazol-5-yl)-3-(2,3-dichlorophenyl)urea as a solid. 1H NMR (300 MHz, DMSO-d6): □ 9.52 (s, 1H), 8.92 (s, 1H), 8.70-8.66 (brs, 2H), 8.05 (dd, J=6.0 Hz, 4.0 Hz, 1H), 7.51-7.42 (m, 3H), 7.34-7.28 (m, 3H), 6.39 (s, 1H), 3.24-3.17 (m, 2H), 3.02-2.98 (m, 2H), 2.58-2.55 (m, 3H), 1.28 (s, 9H). MS (ESI) m/z: 460.2 (M+H+).

Workup

  1. temperatureit was cooled to 0° C.
  2. temperatureThe mixture was heated to 60° C. for 30 min
  3. temperaturecooled to 0° C.
  4. extractionThe product was extracted with CHCl3 (3×25 mL)
  5. washThe combined organic extracts were washed with H2O (1×30 mL), brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. dissolutionThe resultant residue was dissolved in CH2Cl2 (2 mL)
  9. addition3M HCl/EtOAc solution (1 mL) was added
  10. stirringstirred for 10 min

Sources & evidence

ORD record
ord-20ed515ae27b430e99c2a21251f63bf8
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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