Sodium Hydroxide → HCID 10266363, compound

HRID 1008023Notes

Reaction equation

C([O-])(=O)C.[NH4+:5].[CH3:6][C:7]1[N:8]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][S:30][CH3:31])[C:9]2[C:14]([CH3:15])=[C:13]([CH3:16])[N:12]=[C:11](OC3C=CC=CC=3)[C:10]=2[N:24]=1.[OH-].[Na+]>O>[CH3:6][C:7]1[N:8]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][S:30][CH3:31])[C:9]2[C:14]([CH3:15])=[C:13]([CH3:16])[N:12]=[C:11]([NH2:5])[C:10]=2[N:24]=1

Participants

Conditions

Temperature: 160 °C

Procedure

Ammonium acetate (25 g) and 2,6,7-trimethyl-1-[5-(methylthio)pentyl]-4-phenoxy-1H-imidazo[4,5-c]pyridine (2.75 g, 7.45 mmol) were combined and heated at 160° C. overnight. The reaction mixture was cooled to 0° C. and then diluted with water (50 mL). The pH was adjusted to >13 with 15% sodium hydroxide and then the mixture was extracted with chloroform (2×100 mL). The combined extracts were dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified on deactivated silica gel (triethylamine) eluting with 2% methanol in chloroform and then recrystallized from ethyl acetate/hexanes to provide 1.089 g of 2,6,7-trimethyl-1-[5-(methylthio)pentyl]-1H-imidazo[4,5-c]pyridin-4-amine as an off white solid, m.p. 121-122° C.

Workup

temperatureThe reaction mixture was cooled to 0° C.
extractionthe mixture was extracted with chloroform (2×100 mL)
dry with materialThe combined extracts were dried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified on deactivated silica gel (triethylamine)
washeluting with 2% methanol in chloroform
customrecrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record: ord-62966b8c5309434f9c45129a036530a7
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06797718B2

Reaction notes

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