2-Methoxyethylamine → HCID 68686226, compound

HRID 1994120Notes

Reaction equation

HRID 1994120 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1)[C:7]([OH:9])=O)([O-:3])=[O:2].[CH3:17][O:18][CH2:19][CH2:20][NH2:21].CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:17][O:18][CH2:19][CH2:20][NH:21][C:7](=[O:9])[C:6]1[CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

6

Reactant 3

HCID 80182-MethoxyethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 6166023-Nitro-5-(trifluoromethyl)benzoic acid

Product 1

HCID 68686226HCID 68686226, compoundYield 635.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-nitro-5-(trifluoromethyl)benzoic acid (1.00 g, 0.42 mmol) in DCM (20 mL), were added 2-methoxyethanamine (0.41 mL, 0.47 mmol), DMAP (620 mg, 0.51 mmol) and EDCI (900 mg, 0.47 mmol). The reaction mixture was allowed to stir at rt overnight and then concentrated. The residue was diluted with EtOAc and washed with water. The organic solution was dried (MgSO4) and evaporated. The residue was purified by chromatography (SiO2, MeOH/DCM) to yield the title compound as a white solid (780 mg, 63%). LCMS: (FA) ES+ 293.2 (M+1), ES− 291.2 (M−1).

Workup

  1. concentrationconcentrated
  2. additionThe residue was diluted with EtOAc
  3. washwashed with water
  4. dry with materialThe organic solution was dried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by chromatography (SiO2, MeOH/DCM)

Sources & evidence

ORD record
ord-539a7d3c9824494183cea6c8dac8d212
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

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