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

HRID 2221027Notes

Reaction equation

HRID 2221027 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.COC(=O)CN(CC1C=CC=CC=1)CC(NC(OC(C)(C)C)=O)C>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 4653p-FluorophenethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 7359652-Amino-4,5-difluorobenzoic acidHCID 60208241HCID 60208241, compoundHCID 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, EDCI (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-95af06f8277a40719dcd1e5d1eefa584
Source dataset
uspto-grants-2008_05
Patent number
US07368453B2

Reaction notes

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