Triethylamine → 1-(3-Diethylaminopropyl)-3-[4-(2-fluoro-4-nitrophenoxy)pyridin-2-yl]urea

HRID 492675Notes

Reaction equation

HRID 492675 reaction equation
[F:1][C:2]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH2:11])[CH:6]=1.C(N(CC)CC)C.Cl[C:27](OC1C=CC=CC=1)=[O:28].[CH2:36]([N:38]([CH2:43][CH3:44])[CH2:39][CH2:40][CH2:41][NH2:42])[CH3:37]>O1CCCC1.C(OCC)(=O)C.CN(C)C=O>[CH2:36]([N:38]([CH2:43][CH3:44])[CH2:39][CH2:40][CH2:41][NH:42][C:27]([NH:11][C:7]1[CH:6]=[C:5]([O:4][C:3]2[CH:12]=[CH:13][C:14]([N+:16]([O-:18])=[O:17])=[CH:15][C:2]=2[F:1])[CH:10]=[CH:9][N:8]=1)=[O:28])[CH3:37]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 61011N,N-Diethyl-1,3-propanediamineHCID 231531982-Amino-4-(2-fluoro-4-nitrophenoxy)pyridine

Product 1

HCID 231534831-(3-Diethylaminopropyl)-3-[4-(2-fluoro-4-nitrophenoxy)pyridin-2-yl]ureaYield 100%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(2-fluoro-4-nitrophenoxy)pyridin-2-ylamine (400 mg, 1.61 mmol) and triethylamine (0.455 ml, 3.26 mmol) in tetrahydrofuran (40 ml) was added phenyl chloroformate (0.307 ml, 2.45 mmol) dropwise while stirring in an ice bath, followed by stirring for 0.5 hr. The reaction mixture was concentrated under a reduced pressure to give a residue, to which N,N-dimethylformamide (20 ml) and N,N-diethyl-1,3-propanediamine (606 mg, 4.2 mmol) were then added, followed by stirring at room temperature for 1 hr and 45 min. To the reaction mixture was added ethyl acetate (150 ml), washed with a saturated aqueous solution of sodium hydrogencarbonate, and dried over anhydrous sodium sulfate. The solvent was evaporated to give a residue, which was then purified by silica gel column chromatography (Fuji Silysia NH, eluent; hexane:ethyl acetate=1:2, then ethyl acetate) to provide the titled compound (653 mg, 83.8%) as a pale yellow oil.

Workup

  1. stirringby stirring for 0.5 hr
  2. concentrationThe reaction mixture was concentrated under a reduced pressure
  3. customto give a residue
  4. stirringby stirring at room temperature for 1 hr and 45 min
  5. washwashed with a saturated aqueous solution of sodium hydrogencarbonate
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated
  8. customto give a residue, which
  9. customwas then purified by silica gel column chromatography (Fuji Silysia NH, eluent

Sources & evidence

ORD record
ord-a17e36f834384864a6b15a8b67124491
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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