3-[4-(2-Fluoro-4-nitrophenoxy)pyridin-2-yl]-1-methyl-1-(1-methylpiperidin-4-yl)urea → 3-[4-(4-Amino-2-fluorophenoxy)pyridin-2-yl]-1-methyl-1-(1-methylpiperidin-4-yl)urea

HRID 492672Notes

Reaction equation

HRID 492672 reaction equation
[F:1][C:2]1[CH:26]=[C:25]([N+:27]([O-])=O)[CH:24]=[CH:23][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:12](=[O:22])[N:13]([CH3:21])[CH:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]2)[CH:6]=1.[H][H]>O1CCCC1.CO.[C].[Pd]>[NH2:27][C:25]1[CH:24]=[CH:23][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:12](=[O:22])[N:13]([CH3:21])[CH:14]3[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH2:19]3)[CH:6]=2)=[C:2]([F:1])[CH:26]=1

Participants

6

Reactant 2

HCID 231533483-[4-(2-Fluoro-4-nitrophenoxy)pyridin-2-yl]-1-methyl-1-(1-methylpiperidin-4-yl)ureaHCID 178418361HCID 178418361, compound

Product 1

HCID 231535663-[4-(4-Amino-2-fluorophenoxy)pyridin-2-yl]-1-methyl-1-(1-methylpiperidin-4-yl)ureaYield 78%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-[4-(2-Fluoro-4-nitrophenoxy)pyridin-2-yl]-1-methyl-1-(1-methylpiperidin-4-yl)urea (243 mg) was dissolved in tetrahydrofuran (6 ml)-methanol (6 ml), and then 10% palladium carbon (128 mg) was added thereto under a nitrogen atmosphere, followed by replacing with hydrogen inside the reaction system and stirring for 3 hrs. After replacing with nitrogen inside the system, the catalyst was filtered and washed with methanol. The filtrate was concentrated under a reduced pressure to give a residue, which was then purified by silica gel column chromatography (Fuji Silysia NH, eluent; ethyl acetate) and concentrated under a reduced pressure to provide the titled compound (175 mg, 78.0%) as pale yellow powder.

Workup

  1. filtrationthe catalyst was filtered
  2. washwashed with methanol
  3. concentrationThe filtrate was concentrated under a reduced pressure
  4. customto give a residue, which
  5. customwas then purified by silica gel column chromatography (Fuji Silysia NH, eluent; ethyl acetate)
  6. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-2d16ae8006654df48091bd90364ed125
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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