N-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]acetamide → 1-(4-aminobutyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine

HRID 11355Notes

Reaction equation

[NH2:1][C:2]1[C:7]2[N:8]=[CH:9][N:10]([CH2:11][CH2:12][CH2:13][CH2:14][NH:15]C(=O)C)[C:6]=2[C:5]([CH3:19])=[C:4]([CH3:20])[N:3]=1>Cl>[NH2:15][CH2:14][CH2:13][CH2:12][CH2:11][N:10]1[C:6]2[C:5]([CH3:19])=[C:4]([CH3:20])[N:3]=[C:2]([NH2:1])[C:7]=2[N:8]=[CH:9]1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of N-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]acetamide (˜2.1 g) in 6 N hydrochloric acid (30 mL) was sealed in a flask and then heated at 100° C. for about 30 hours. The reaction mixture was allowed to cool to ambient temperature and then filtered to remove any particulates. The filtrate was made basic (pH 14) with 25% sodium hydroxide and then extracted with chloroform (×2). The aqueous layer was combined with sodium chloride (20 g) and then extracted with chloroform (×3). The organics were combined, washed with brine, dried over sodium sulfate and then concentrated under reduced pressure to provide 1.44 g of 1-(4-aminobutyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine.

Workup

temperatureto cool to ambient temperature
filtrationfiltered
customto remove any particulates
extractionextracted with chloroform (×2)
extractionextracted with chloroform (×3)
washwashed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-744573d22e094a1085efd4fa62a9a1fb
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07098221B2

Reaction notes

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