Potassium Hydroxide → 6-iodo-3-(3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-3H-imidazo[4,5-b]pyridin-2-amine

HRID 2178377Notes

Reaction equation

[I:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([NH:11]C(=O)OCC)[N:8]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]4[CH:27]=[N:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=4)=[C:20]([O:34][CH3:35])[CH:19]=3)[C:5]2=[N:6][CH:7]=1.[OH-].[K+]>C(O)CO.O.[Cl-].[Na+].O>[I:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([NH2:11])[N:8]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]4[CH:27]=[N:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=4)=[C:20]([O:34][CH3:35])[CH:19]=3)[C:5]2=[N:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of ethyl (6-iodo-3-(3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-3H-imidazo[4,5-b]pyridin-2-yl)carbamate (Example 3-36-2) (0.42 g, 0.71 mmol) in ethylene glycol (6 mL) and water (1 mL) was added potassium hydroxide (0.197 g, 3.51 mmol). The resulting mixture was heated to 100° C. After 12 h, the mixture was allowed to cool to room temperature and was diluted with brine (40 mL). The mixture was extracted with ethyl acetate (3×40 mL). The combined organic phases were dried over sodium sulfate, filtered, and concentrated. Chromatographic purification of the residue (silica gel, 3% methanol in dichloromethane elute) afforded 0.206 g (56%) of 6-iodo-3-(3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-3H-imidazo[4,5-b]pyridin-2-amine as a yellow solid.

Workup

temperatureto cool to room temperature
extractionThe mixture was extracted with ethyl acetate (3×40 mL)
dry with materialThe combined organic phases were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customChromatographic purification of the residue (silica gel, 3% methanol in dichloromethane elute)

Sources & evidence

ORD record: ord-cbaad4edf45145fab08a4e2ff79707f4
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067914B1

Reaction notes

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