3-Pyridinemethanamine → HCID 86757971, compound

HRID 843147Notes

Reaction equation

HRID 843147 reaction equation
[CH:1]1([CH2:7][CH2:8][NH:9][C:10]([C:12]2[O:13][C:14]3[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][CH2:24][CH2:25]Br)[C:15]=3[C:16]=2[CH3:17])=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N:27]1[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33][NH2:34])[CH:28]=1>CN1CCCC1=O.C(OCC)(=O)C>[CH:1]1([CH2:7][CH2:8][NH:9][C:10]([C:12]2[O:13][C:14]3[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][CH2:24][CH2:25][NH:34][CH2:33][C:29]4[CH:28]=[N:27][CH:32]=[CH:31][CH:30]=4)[C:15]=3[C:16]=2[CH3:17])=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 310183-PyridinemethanamineHCID 54533680HCID 54533680, compound

Product 1

HCID 86757971HCID 86757971, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

4-(3-Bromo-propoxy)-3-methyl-benzofuran-2-carboxylic acid (2-cyclohexyl-ethyl)-amide (100 mg) and 3-picolyl amine (250 μl) were dissolved in 1-methylpyrrolidone (2 ml) and heated at 100° C. for two hours. The reaction mixture was dissolved in ethyl acetate and washed with saturated ammonium chloride solution and water. The organic solvent was dried over anhydrous sodium sulfate and evaporated to dryness. The residue was purified by silica gel column chromatography (dichloromethane-MeOH) to afford 3-methyl-4-{3-[(pyridin-3-ylmethyl)-amino]-propoxy}-benzofuran-2-carboxylic acid (2-cyclohexyl-ethyl)-amide. ESI-MS: m/z 450 (MH+); 1H-NMR (CDCl3): δ 0.85-1.85 (13H, m), 2.05 (2H, quintet, J=6.5 Hz), 2.72 (3H, s), 2.90 (2H, t, J=6.5 Hz), 3.46 (2H, m), 3.85 (2H, s), 4.15 (2H, t, J=6.5 Hz), 6.53 (1H, t, J=6 Hz), 6.62 (1H, d, 8 Hz), 7.01 (1H, d, J=8 Hz), 7.26 (2H, m), 7.68 (1H, dd, J=1.5 Hz, 8 Hz), 8.49 (1H, br d, J=3.5 Hz), 8.56 (1H, br s).

Workup

  1. washwashed with saturated ammonium chloride solution and water
  2. dry with materialThe organic solvent was dried over anhydrous sodium sulfate
  3. customevaporated to dryness
  4. customThe residue was purified by silica gel column chromatography (dichloromethane-MeOH)

Sources & evidence

ORD record
ord-bd5d5bce33e148718de73449c6d0c42f
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

Loading…