1,2-Dichloroethane → 4-Azido-N-[2-(2-fluoro-4-methoxy-phenyl)-ethyl]-benzamide

HRID 890378Notes

Reaction equation

HRID 890378 reaction equation
[N:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=1)=[N+:2]=[N-:3].C(Cl)CCl.CCN(C(C)C)C(C)C.[F:26][C:27]1[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[CH:29][C:28]=1[CH2:35][CH2:36][NH2:37]>C1COCC1.CN(C1C=CN=CC=1)C.CCOC(C)=O>[N:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:37][CH2:36][CH2:35][C:28]2[CH:29]=[CH:30][C:31]([O:33][CH3:34])=[CH:32][C:27]=2[F:26])=[O:10])=[CH:11][CH:12]=1)=[N+:2]=[N-:3]

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 30341844-Azidobenzoic acidHCID 221750092-(2-Fluoro-4-methoxyphenyl)ethanamine

Product 1

HCID 222509594-Azido-N-[2-(2-fluoro-4-methoxy-phenyl)-ethyl]-benzamide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Azidobenzoic acid (1.5 equivalents) was dissolved in THF. EDC (1.5 equivalents), DIEA (1.5 equivalents) and DMAP (0.1 equivalents) were added followed by 2-(2-fluoro-4-methoxy-phenyl)-ethylamine (1 equivalent). The reaction was then allowed to stir overnight at room temperature. EtOAc was added and the reaction was washed with 10% citric acid, 10% sodium bicarbonate and brine. After drying over Na2SO4, solvent was removed and the residue was purified by flash chromatography 20% EtOAc/DCM to yield the title compounds as a white powder.

Workup

  1. washthe reaction was washed with 10% citric acid, 10% sodium bicarbonate and brine
  2. dry with materialAfter drying over Na2SO4, solvent
  3. customwas removed
  4. customthe residue was purified by flash chromatography 20% EtOAc/DCM

Sources & evidence

ORD record
ord-9f6171c55d914dc0b5d81ac611348253
Source dataset
uspto-grants-2006_02
Patent number
US06995269B2

Reaction notes

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