3-Pyridinemethanamine → HCID 489114, compound

HRID 843158Notes

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][CH2:18][CH2:19]Br)[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][CH2:18][CH2:19][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

Conditions

Temperature: 50 °C

Procedure

4-(3-bromo-propoxy)-3-methyl-benzofuran-2-carboxylic acid ethyl ester (Example 5-a: 180 mg) and 3-picolylamine (500 μl) were dissolved in ethanol (2 ml) and heated at 50° C. for 16 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 ethyl ester (150 mg) as a colorless oil. EI-MS: m/z 368 (M+); 1H-NMR (CDCl3): δ 1.44 (3H, t, J=7 Hz), 2.07 (2H, quintet, J=6.5 Hz), 2.67 (3H, s), 2.89 (2H, t, J=7 Hz), 3.84 (2H, s), 4.17 (2H, t, J=6 Hz), 4.44 (2H, q, J=7 Hz), 6.62 (1H, d, 8 Hz), 7.12 (1H, d, J=8 Hz), 7.21 (1H, dd, J1=8 Hz, J2=5 Hz), 7.30 (1H, t, J=8 Hz), 7.66 (1H, dd, J1=8 Hz, J2=2 Hz), 8.49 (1H, dd, J1=5 Hz, J2=2 Hz), 8.57 (1H, d, J=2 Hz).

Workup

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

Sources & evidence

ORD record: ord-809ec9774a274e95a27e2b258278c759
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06376491B1

Reaction notes

Loading…