HCID 67183816, compound → 1-[3-(1-Piperidin-4-yl-4-pyridin-4-yl-1h-pyrazol-3-yl)-phenyl]-3-(4-trifluoromethyl-phenyl)-urea

HRID 45819Notes

Reaction equation

HRID 45819 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH:18]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)[C:16]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([NH:31][C:32]([NH:34][C:35]4[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:37][CH:36]=4)=[O:33])[CH:26]=3)=[N:15]2)[CH2:10][CH2:9]1)=O)(C)(C)C>O1CCOCC1.C(OCC)(=O)C>[NH:8]1[CH2:9][CH2:10][CH:11]([N:14]2[CH:18]=[C:17]([C:19]3[CH:20]=[CH:21][N:22]=[CH:23][CH:24]=3)[C:16]([C:25]3[CH:26]=[C:27]([NH:31][C:32]([NH:34][C:35]4[CH:36]=[CH:37][C:38]([C:41]([F:44])([F:42])[F:43])=[CH:39][CH:40]=4)=[O:33])[CH:28]=[CH:29][CH:30]=3)=[N:15]2)[CH2:12][CH2:13]1

Participants

4

Reactant 1

HCID 67183816HCID 67183816, compound

Product 1

HCID 446228131-[3-(1-Piperidin-4-yl-4-pyridin-4-yl-1h-pyrazol-3-yl)-phenyl]-3-(4-trifluoromethyl-phenyl)-urea

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To 4-(4-pyridin-4-yl-3-{3-[3-(4-trifluoromethyl-phenyl)-ureido]-phenyl}-pyrazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (100 mg, 0.16 mmol) in dioxane (2 mL) HCl 4M in dioxane (1 mL, 3.30 mmol) was added. After one hour the reaction was diluted with ethyl acetate (50 mL) and washed with saturated NaHCO3 solution (3×50 mL) and brine (1×50 mL). The organic phase was dried over Na2SO4, filtered and the solvent was evaporated under reduced pressure. The deprotected urea was isolated by reverse phase chromatography.

Workup

  1. washwashed with saturated NaHCO3 solution (3×50 mL) and brine (1×50 mL)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-12dbcc4149eb4bd581d12cb21bb2d37c
Source dataset
uspto-grants-2013_09
Patent number
US08541575B2

Reaction notes

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