HCID 118114020, compound → N2-(3-ethoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-5-iodopyridine-2,3-diamine

HRID 706472Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][C:21]=1[O:22][CH2:23][C:24]1[CH:25]=[N:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=1)[CH2:7][NH:8][C:9]1[C:14]([N+:15]([O-])=O)=[CH:13][C:12]([I:18])=[CH:11][N:10]=1)[CH3:2]>C(O)(=O)C.C(OCC)(=O)C.[Fe]>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][C:21]=1[O:22][CH2:23][C:24]1[CH:25]=[N:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=1)[CH2:7][NH:8][C:9]1[C:14]([NH2:15])=[CH:13][C:12]([I:18])=[CH:11][N:10]=1)[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

To a stirred suspension of N-(3-ethoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-5-iodo-3-nitropyridin-2-amine (4.34 g, 8.09 mmol) in acetic acid (25 mL) was added iron powder (2.26 g, 40.46 mmol). The reaction mixture was heated to 90° C. After 15 min, the reaction mixture became a gray-brown suspension. The mixture was allowed to cool to room temperature and was diluted with ethyl acetate (200 mL). The mixture was filtered through Celite with the aid of additional ethyl acetate (50 mL). The filtrate was washed with water (2×50 mL) and then with 1N sodium hydroxide solution (3×50 mL). The organic phase was dried over magnesium sulfate, filtered, and concentrated to provide 3.99 g (97%) of N2-(3-ethoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-5-iodopyridine-2,3-diamine as a tan solid.

Workup

temperatureto cool to room temperature
filtrationThe mixture was filtered through Celite with the aid of additional ethyl acetate (50 mL)
washThe filtrate was washed with water (2×50 mL)
dry with materialThe organic phase was dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-7f5d0ffb37f84dc88f09b86b89a9f52e
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174986B2

Reaction notes

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