3-Pyridinemethanamine → HCID 22615077, compound

HRID 843154Notes

Reaction equation

HRID 843154 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][CH:18]3[CH2:20][O:19]3)[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].[N:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][NH2:28])[CH:22]=1>C(O)C.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][CH:18]([OH:19])[CH2:20][NH:28][CH2:27][C:23]3[CH:22]=[N:21][CH:26]=[CH:25][CH:24]=3)[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 310183-PyridinemethanamineHCID 54566649HCID 54566649, compound

Product 1

HCID 22615077HCID 22615077, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

3-Methyl-4-oxiranylmethoxy-benzofuran-2-carboxylic acid ethyl ester (500 mg) (Naresh K. Sangwan et al., Eur. J. Med. Chem. (1987), 22(2), 153-6) and 3-picolylamine (1 ml) were dissolved in ethanol (5 ml) and stirred at 70° 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 4-[2-hydroxy-3-[(pyridin-3-ylmethyl)-amino]-propoxy]-3-methyl-benzofuran-2-carboxylicacid ethyl ester (330 mg) as a white powder. FAB-MS: m/z 385 (MH+); 1H-NMR (CDCl3): δ 1.44 (3H, t, J=7 Hz), 2.70 (3H, s),2.86 (1H, dd, J1=12 Hz, J2=7 Hz),2.97 (1H, dd, J1=12 Hz, J2=3.5 Hz), 3.85 (1H, d, J=14 Hz), 3.91 (1H, d, J=14 Hz), 4.13 (3H, m), 4.44 (2H, q, J=7 Hz), 6.63 (1H, d, J=8 Hz), 7.14 (1H, d, J=8 Hz), 7.26 (1H, m), 7.28 (1H, t, J=8 Hz), 7.68 (1H, br d, J=8 Hz),8.52 (1H, dd, J1=5 Hz, J2=2 Hz), 8.58 (1H, d, J=2 Hz).

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-14d5b9571f9844bda4a8b5a2ae38f3fc
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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