4-Methoxybenzylamine → HCID 68569400, compound

HRID 2100510Notes

Reaction equation

HRID 2100510 reaction equation
Cl[C:2]1[N:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][NH2:19])=[CH:16][CH:15]=1>C(O)CO>[F:11][C:8]1[CH:9]=[N:10][C:2]([NH:19][CH2:18][C:17]2[CH:20]=[CH:21][C:14]([O:13][CH3:12])=[CH:15][CH:16]=2)=[C:3]([CH:7]=1)[C:4]([NH2:6])=[O:5]

Participants

4

Reactant 2

HCID 754524-MethoxybenzylamineHCID 126297962-Chloro-5-fluoropyridine-3-carboxamide

Product 1

HCID 68569400HCID 68569400, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A solution of 2-chloro-5-fluoro-nicotinamide (70 mg, 0.40 mmol) and 4-methoxybenzylamine (550 mg, 4.01 mmol) in ethyleneglycol (1 ml) was microwaved for 50 min at 140° C. A white solid was filtered off and the filtrate evaporated. The residue was dissolved in EtOAc, washed with water and brine, dried over MgSO4 and the solvent removed under reduced pressure. The residue was purified by column chromatography (silica gel, EtOAc/heptane, 1/1) to obtain 5-fluoro-2-(4-methoxy-benzylamino)-nicotinamide (56 mg, 0.2 mmol; 51%) as white solid. MS (m/e): 276.3 [M+H+].

Workup

  1. filtrationA white solid was filtered off
  2. customthe filtrate evaporated
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with water and brine
  5. dry with materialdried over MgSO4
  6. customthe solvent removed under reduced pressure
  7. customThe residue was purified by column chromatography (silica gel, EtOAc/heptane, 1/1)

Sources & evidence

ORD record
ord-d61cb20434f14f10894c4b0e96fd8931
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

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