HCID 53630190, compound → 1-[2-(4-aminophenyl)-5-tert-butyl-2H-pyrazol-3-yl]-3-[4-(pyridin-4-yloxy)phenyl]urea

HRID 221884Notes

Reaction equation

HRID 221884 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:19][C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]3[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=3)=[CH:25][CH:24]=2)=[O:21])[N:8]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>CCO.[Pd]>[NH2:16][C:13]1[CH:14]=[CH:15][C:10]([N:8]2[C:7]([NH:19][C:20]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][C:30]4[CH:31]=[CH:32][N:33]=[CH:34][CH:35]=4)=[CH:25][CH:24]=3)=[O:21])=[CH:6][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[N:9]2)=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 53630190HCID 53630190, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 536301891-[2-(4-aminophenyl)-5-tert-butyl-2H-pyrazol-3-yl]-3-[4-(pyridin-4-yloxy)phenyl]ureaYield 77%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-[5-tert-butyl-2-(4-nitrophenyl)-2H-pyrazol-3-yl]-3-[4-(pyridin-4-yloxy)phenyl]urea (2.5 g, 5.3 mmol) in anhydrous EtOH (40 mL) was added to a round bottle (100 mL) flask containing 10% Pd/C (30 mg). The reaction vessel was fitted with a balloon adapter and charged with hydrogen and evacuated three times until the reaction was under a H2 atmosphere. The reaction mixture was stirred at room temperature for 18 h, and then filtered through a pad of celite. The celite was washed with EtOH (200 mL) and the filtrate was concentrated at reduced pressure. The residue was purified by MPLC (1:1 hexanes/EtOAc) to give 1.8 g (77%) of the desired product. 1H-NMR (DMSO-d6) δ 9.16 (s, 1H), 8.42 (d, J=5.4 Hz, 2H), 8.17 (s, 1H), 7.47 (d, J=6.9 Hz, 2H), 7.09 to 7.04 (m, 4H), 6.86 (d, J=5.7 Hz, 2H), 6.64 (d, J=6.6 Hz, 2H), 6.28 (s, 1H), 6.38 (s, 2H), 1.18 (s, 9H); MS LC-MS [M+H]+=443, RT=1.95 min.

Workup

  1. customThe reaction vessel was fitted with a balloon adapter
  2. customevacuated three times until the reaction
  3. filtrationfiltered through a pad of celite
  4. washThe celite was washed with EtOH (200 mL)
  5. concentrationthe filtrate was concentrated at reduced pressure
  6. customThe residue was purified by MPLC (1:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-c6acef2d54dc46d3b0d1334eba8a4e47
Source dataset
uspto-grants-2012_06
Patent number
US08207166B2

Reaction notes

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