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

HRID 492673Notes

Reaction equation

HRID 492673 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.[CH2:19]([N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])[CH3:20].ClC([O:29][C:30]1C=CC=CC=1)=O.[CH2:36]([N:38](CC)[CH2:39]CCNC)C>O1CCCC1.C(OCC)(=O)C.CN(C)C=O>[CH2:19]([N:21]([CH2:24][CH3:25])[CH2:22][CH2:23][CH2:36][N:38]([CH3:39])[C:30]([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:29])[CH3:20]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 79577N,N-Diethyl-N'-methyl-1,3-propanediamineHCID 231531982-Amino-4-(2-fluoro-4-nitrophenoxy)pyridine

Product 1

HCID 231532451-(3-Diethylaminopropyl)-3-[4-(2-fluoro-4-nitrophenoxy)pyridin-2-yl]-1-methylureaYield 100%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(2-fluoro-4-nitrophenoxy)pyridin-2-ylamine (300 mg, 1.2 mmol) and triethylamine (0.335 ml, 2.4 mmol) in tetrahydrofuran (30 ml) was added phenyl chloroformate (0.226 ml, 1.8 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 (6.0 ml) and N,N-diethyl-N′-methyl-1,3-propanediamine (606 mg, 4.2 mmol) were added, followed by stirring at room temperature for 4 hrs 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 filtered by silica gel (Fuji Silysia NH, hexane:ethyl acetate=3:1 to 1:1) to provide the titled compound (503 mg, 100%) as a 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 4 hrs 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. filtrationwas filtered by silica gel (Fuji Silysia NH, hexane:ethyl acetate=3:1 to 1:1)

Sources & evidence

ORD record
ord-42588a2a971b4cbabe83477ef8b5ca54
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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