Triethylamine → N-(2-Fluoro-1,1-dimethylethyl)-2,4-difluorobenzamide

HRID 586790Notes

Reaction equation

HRID 586790 reaction equation
CCN=C=NCCCN(C)C.Cl.[F:13][C:14]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:15]=1[C:16]([OH:18])=O.Cl.[F:25][CH2:26][C:27]([NH2:30])([CH3:29])[CH3:28].C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>C(Cl)Cl>[F:25][CH2:26][C:27]([NH:30][C:16](=[O:18])[C:15]1[CH:19]=[CH:20][C:21]([F:23])=[CH:22][C:14]=1[F:13])([CH3:29])[CH3:28]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 741022,4-Difluorobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 139352511-Fluoro-2-methylpropan-2-amine hydrochloride

Product 1

HCID 10198515N-(2-Fluoro-1,1-dimethylethyl)-2,4-difluorobenzamideYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

WSC HCl (1.15 g, 6 mmol) was added to a mixture of 2,4-difluorobenzoic acid (0.95 g, 6 mmol), 2-fluoro-1,1-dimethylethylamine hydrochloride (J. Med. Chem., 34, 29-37(1991): 0.77 g, 6 mmol), HOBt (0.81 g, 6 mmol) and triethylamine (0.91 g, 9 mmol) in methylene chloride (15 ml), and stirred at room temperature for 3 hours. The reaction mixture was concentrated, diluted with ethyl acetate and washed with saturated aqueous NaHCO3, 1N hydrochloric acid, saturated aqueous NaHCO3 and brine, successively, dried over MgSO4 and concentrated under a reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=20/1) to give the title compound (0.61 g: 44%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with ethyl acetate
  3. washwashed with saturated aqueous NaHCO3, 1N hydrochloric acid, saturated aqueous NaHCO3 and brine
  4. dry with materialsuccessively, dried over MgSO4
  5. concentrationconcentrated under a reduced pressure
  6. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-4ea4f38997dd4427b20ebededd071221
Source dataset
uspto-grants-2005_08
Patent number
US06936736B2

Reaction notes

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