Tetrahydrofuran → 1-(3-Diethylaminopropyl)-3-[4-(4-amino-2-fluorophenoxy)pyridin-2-yl]urea

HRID 492676Notes

Reaction equation

HRID 492676 reaction equation
[CH2:1]([N:3]([CH2:28][CH3:29])[CH2:4][CH2:5][CH2:6][NH:7][C:8]([NH:10][C:11]1[CH:16]=[C:15]([O:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][C:19]=2[F:27])[CH:14]=[CH:13][N:12]=1)=[O:9])[CH3:2].O1CCCC1>CO.[C].[Pd]>[CH2:28]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][CH2:6][NH:7][C:8]([NH:10][C:11]1[CH:16]=[C:15]([O:17][C:18]2[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][C:19]=2[F:27])[CH:14]=[CH:13][N:12]=1)=[O:9])[CH3:29]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 231534831-(3-Diethylaminopropyl)-3-[4-(2-fluoro-4-nitrophenoxy)pyridin-2-yl]urea

Product 1

HCID 231530591-(3-Diethylaminopropyl)-3-[4-(4-amino-2-fluorophenoxy)pyridin-2-yl]ureaYield 62.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-(3-diethylaminopropyl)-3-[4-(2-fluoro-4-nitrophenoxy)pyridin-2-yl]urea (547 mg, 1.35 mmol) in methanol (40 ml)-tetrahydrofuran (20 ml) was added 10% palladium carbon (200 mg), followed by stirring under a hydrogen atmosphere at room temperature for 12 hrs. 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, ethyl acetate, then ethyl acetate:methanol=10:1) to provide the titled compound (316 mg, 62.3%) as a yellow oil.

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, ethyl acetate

Sources & evidence

ORD record
ord-38cb687f5175412a9098cf3367aac06c
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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