4-Fluorobenzylamine → HCID 178432814, compound

HRID 2267094Notes

Reaction equation

HRID 2267094 reaction equation
[Br:1][C:2]1[C:3]([CH3:12])=[N:4][CH:5]=[C:6]([C:10]=1[OH:11])[C:7]([OH:9])=O.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[F:35][C:36]1[CH:43]=[CH:42][C:39]([CH2:40][NH2:41])=[CH:38][CH:37]=1>CNC=O.O>[Br:1][C:2]1[C:3]([CH3:12])=[N:4][CH:5]=[C:6]([C:10]=1[OH:11])[C:7]([NH:41][CH2:40][C:39]1[CH:42]=[CH:43][C:36]([F:35])=[CH:37][CH:38]=1)=[O:9]

Participants

7

Reactant 4

HCID 673264-FluorobenzylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178432818HCID 178432818, compound

Product 1

HCID 178432814HCID 178432814, compoundYield 77.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31254N-MethylformamideSolvent

Procedure

The compound 20 (138 g, 0.596 mol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (148 g, 0.775 mol), and 1-hydroxybenzotriazole (100 g, 0.656 mol) were dissolved in methylformamide (970 ml), and 4-fluorobenzylamine (79 ml, 0.715 mol) was added. After the reaction solution was stirred at room temperature for 9 hours, water (2000 ml) was added, and crystals were collected by filtration, followed by washing with ether. 5-Bromo-N-(4-fluorobenzyl)-4-hydroxy-6-methylnicotinamide 21 (156 g, 77%) was obtained as a colorless crystal.

Workup

  1. filtrationcrystals were collected by filtration
  2. washby washing with ether

Sources & evidence

ORD record
ord-dd1e4333125646d89f121f0312e59044
Source dataset
uspto-grants-2010_12
Patent number
US07858788B2

Reaction notes

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