Methylamine → 5-(4-Amino-3-fluorophenoxy)-N-methylnicotinamide

HRID 658485

Reaction equation

HRID 658485 reaction equation
CO[C:3](=[O:19])[C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[C:13]([F:18])[CH:12]=2)[CH:7]=[N:6][CH:5]=1.[CH3:20][NH2:21]>CO>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]([O:10][C:8]2[CH:7]=[N:6][CH:5]=[C:4]([CH:9]=2)[C:3]([NH:21][CH3:20])=[O:19])=[CH:12][C:13]=1[F:18]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 599875035-(4-Amino-3-fluorophenoxy)nicotinic acid methyl ester

Product 1

HCID 583854225-(4-Amino-3-fluorophenoxy)-N-methylnicotinamideYield 80.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 5-(4-amino-3-fluorophenoxy)nicotinic acid methyl ester (0.50 g, 1.91 mmol) in MeOH (2 mL) was added methylamine (0.63 g, 19.1 mmol, 2.0 M in MeOH). The reaction flask was sealed and heated at 40° C. for 4 h. Solvent was removed under reduced pressure, and the crude product was purified by column chromatography eluted with 5% MeOH/CH2Cl2 to give the 0.4 g (80%) of the title compound. 1H-NMR (DMSO-d6) δ 8.65 (d, J=1.8 Hz, 1H), 8.62 to 8.60 (m, 1H), 7.54 to 7.52 (m, 1H), 6.94 (dd, J=2.7, 12.0 Hz, 1H), 6.81 to 6.67 (m, 3H), 5.10 (s, 2H), 2.72 (d, J=2.4 Hz, 3H); MS LC-MS [M+H]+=262.2, RT=0.27 min.

Workup

  1. customThe reaction flask was sealed
  2. customSolvent was removed under reduced pressure
  3. customthe crude product was purified by column chromatography
  4. washeluted with 5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-2277c1b07ca24255be14d2e82eee4ea1
Source dataset
uspto-grants-2011_12
Patent number
US08076488B2

Linked notes

Loading…