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

HRID 1843607Notes

Reaction equation

HRID 1843607 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-52025abab2e141149fefc6d6ca14c10d
Source dataset
uspto-grants-2015_02
Patent number
US08946250B2

Reaction notes

Loading…