4-Fluoroaniline → 2-amino-N-(4-fluorophenyl)nicotinamide

HRID 2241392Notes

Reaction equation

HRID 2241392 reaction equation
C1C=CC2N(O)N=NC=2C=1.O.CCN=C=NCCCN(C)C.[NH2:23][C:24]1[N:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26]([OH:28])=O.CCN(C(C)C)C(C)C.[F:42][C:43]1[CH:48]=[CH:47][C:46]([NH2:49])=[CH:45][CH:44]=1>O.CN(C=O)C>[NH2:23][C:24]1[N:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26]([NH:49][C:46]1[CH:47]=[CH:48][C:43]([F:42])=[CH:44][CH:45]=1)=[O:28]

Participants

8

Reactant 5

HCID 97314-FluoroanilineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 729302-Aminonicotinic acidHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 551366622-amino-N-(4-fluorophenyl)nicotinamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A 1 L round-bottomed flask was charged with HOBT-H2O (20.37 g, 133.0 mmol), EDCI (25.50 g, 133.0 mmol), 2-aminonicotinic acid (12.25 g, 88.69 mmol), and DMF (750 mL). The reaction mixture was stirred for 30 minutes, then Hunig's base (30.90 ml, 177.4 mmol) and 4-fluorobenzenamine (10.65 ml, 110.9 mmol) were added. The reaction mixture was stirred for 18 hours, then diluted with water. After 30 minutes the resulting precipitate was collected by filtration and dried to provide the product. LRMS M+1 (231.9) observed.

Workup

  1. stirringThe reaction mixture was stirred for 18 hours
  2. filtrationAfter 30 minutes the resulting precipitate was collected by filtration
  3. customdried
  4. customto provide the product

Sources & evidence

ORD record
ord-a3f227340ccd48559ca12393d3099ff0
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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