Dimethylamine → HCID 23153179, compound

HRID 492667Notes

Reaction equation

HRID 492667 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=2[F:18])[CH:5]=[CH:4][N:3]=1.[CH2:19]([N:21]([CH2:24]C)[CH2:22]C)C.ClC(OC1C=CC=CC=1)=[O:28].CNC>O1CCCC1.CO>[CH3:19][N:21]([CH3:24])[C:22]([NH:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=2[F:18])[CH:5]=[CH:4][N:3]=1)=[O:28]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 231531982-Amino-4-(2-fluoro-4-nitrophenoxy)pyridine

Product 1

HCID 23153179HCID 23153179, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Amino-4-(2-fluoro-4-nitrophenoxy)pyridine (249 mg) was dissolved in tetrahydrofuran (5 ml) under a nitrogen atmosphere, and then triethylamine (0.21 ml) and phenyl chloroformate (0.19 ml) were added dropwise thereto while cooling in an ice water bath, followed by stirring at room temperature for 15 min. To the reaction mixture was added 2 M solution of dimethylamine in methanol (4.0 ml), followed by stirring for 2 days. The solvent was evaporated under a reduced pressure to give a residue, which was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=1:3, then ethyl acetate) to provide the titled compound (219 mg, 68%) as pale yellow crystals.

Workup

  1. temperaturewhile cooling in an ice water bath
  2. stirringby stirring for 2 days
  3. customThe solvent was evaporated under a reduced pressure
  4. customto give a residue, which
  5. customwas purified by silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-761ae5a3fa394f51bf2f43eed65f6657
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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