Hexanoic Acid → 7-methyl-2-pentyl-3H-Imidazo[4,5-b]pyridine

HRID 1029567Notes

Reaction equation

HRID 1029567 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([CH3:9])[CH:5]=[CH:4][N:3]=1.[C:10](O)(=O)[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]>>[CH3:9][C:6]1[CH:5]=[CH:4][N:3]=[C:2]2[N:1]=[C:10]([CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[NH:8][C:7]=12

Participants

3

Reactant 2

HCID 8892Hexanoic AcidHCID 3174954-Methylpyridine-2,3-diamine

Product 1

HCID 198141217-methyl-2-pentyl-3H-Imidazo[4,5-b]pyridine

Procedure

The title compound was prepared from 2,3-diamino-4-picoline (0.246 g, 2 mmol) and hexanoic acid (0.25 ml, 2 mmols) according to the procedure described in Step 1 of Example 9. The crude product was purified by flash chromatography on silica-gel using EtOAc-MeOH (9:1) to give the pure product (0.28 g, 69%) as a tan colored solid. 1H NMR (300 MHz, CDCl3): 8.17 (d, 1H, J=5 Hz), 7.05 (d, 1H, J=5 Hz), 3.03 (t, 2H, J=7.8 Hz), 2.70 (s, 3H), 1.32-2.1 (m, 6H), 0.92 (t, 3H, J=7.8 Hz).

Workup

  1. customThe crude product was purified by flash chromatography on silica-gel

Sources & evidence

ORD record
ord-49770a00bf45423d857fa46a25d5c2ed
Source dataset
uspto-grants-1992_04
Patent number
US05102880

Reaction notes

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