Benzamide → 2-Amino-4,5-difluoro-N-[2-(4-fluorophenyl)ethyl]benzamide

HRID 2265920Notes

Reaction equation

HRID 2265920 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:12])[C:5](=[CH:9][C:10]=1[F:11])[C:6]([OH:8])=O.O.OC1C2N=NNC=2C=CC=1.C(N(C(C)C)CC)(C)C.[F:33][C:34]1[CH:39]=[CH:38][C:37]([CH2:40][CH2:41][NH2:42])=[CH:36][CH:35]=1.CCN=C=NCCCN(C)C.Cl.C(N)(=O)C1C=CC=CC=1>C1COCC1.CCOC(C)=O>[NH2:12][C:4]1[CH:3]=[C:2]([F:1])[C:10]([F:11])=[CH:9][C:5]=1[C:6]([NH:42][CH2:41][CH2:40][C:37]1[CH:38]=[CH:39][C:34]([F:33])=[CH:35][CH:36]=1)=[O:8]

Participants

9

Reactant 6

HCID 2331BenzamideHCID 4653p-FluorophenethylamineHCID 81531DiisopropylethylamineHCID 7359652-Amino-4,5-difluorobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178526939HCID 178526939, compound2×

Product 1

HCID 210275152-Amino-4,5-difluoro-N-[2-(4-fluorophenyl)ethyl]benzamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 4,5-difluoro anthranilic acid (2.0 g, 11.6 mmol) in anhydrous THF (30 mL) was added hydroxybenzotriazole hydrate (HOBt) (1.56 g, 11.6 mmol), diisopropylethyl amine (2.01 mL, 11.6. mmol), and 4-fluorophenylethyl amine (1.52 mL, 11.6 mmol). After all of the HOBt had completely dissolved, EDCl (2.21 g, 11.6 mmol) was added and the resulting orange solution was stirred at room temperature for 16 hours. The solvent was removed, and the residue was chromatographed on silica eluting with 15% EtOAc in hexanes giving the desired benzamide (2) as white crystals (3.07 g, 10.4 mmol, 90%).

Workup

  1. customThe solvent was removed

Sources & evidence

ORD record
ord-3550612cd3834e14ba37912d91f7b807
Source dataset
uspto-grants-2010_12
Patent number
US07858631B2

Reaction notes

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