Ammonium Chloride → N2-(4-(cyclopropyl(6-methoxypyridin-3-yl)methoxy)-3-methoxybenzyl)-5-(1-methyl-1H-pyrazol-4-yl)pyridine-2,3-diamine

HRID 2178384Notes

Reaction equation

[CH:1]1([CH:4]([C:31]2[CH:32]=[N:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=2)[O:5][C:6]2[CH:28]=[CH:27][C:9]([CH2:10][NH:11][C:12]3[C:17]([N+:18]([O-])=O)=[CH:16][C:15]([C:21]4[CH:22]=[N:23][N:24]([CH3:26])[CH:25]=4)=[CH:14][N:13]=3)=[CH:8][C:7]=2[O:29][CH3:30])[CH2:3][CH2:2]1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[CH:1]1([CH:4]([C:31]2[CH:32]=[N:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=2)[O:5][C:6]2[CH:28]=[CH:27][C:9]([CH2:10][NH:11][C:12]3[C:17]([NH2:18])=[CH:16][C:15]([C:21]4[CH:22]=[N:23][N:24]([CH3:26])[CH:25]=4)=[CH:14][N:13]=3)=[CH:8][C:7]=2[O:29][CH3:30])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of N-(4-(cyclopropyl(6-methoxypyridin-3-yl)methoxy)-3-methoxybenzyl)-5-(1-methyl-1H-pyrazol-4-yl)-3-nitropyridin-2-amine (1.10 g, 2.13 mmol) and ammonium chloride (0.564 g, 10.54 mmol) in ethanol (8 mL) and water (2 mL) was added iron powder (0.596 g, 10.67 mmol). The mixture was heated to 80° C. After 2 h, the mixture was allowed to cool to room temperature and was filtered through Celite. The filtrate was concentrated. Chromatographic purification of the residue (neutral alumina, 2% methanol in dichloromethane elute) afforded 0.984 g (95%) of N2-(4-(cyclopropyl(6-methoxypyridin-3-yl)methoxy)-3-methoxybenzyl)-5-(1-methyl-1H-pyrazol-4-yl)pyridine-2,3-diamine as a brown solid.

Workup

temperatureto cool to room temperature
filtrationwas filtered through Celite
concentrationThe filtrate was concentrated
customChromatographic purification of the residue (neutral alumina, 2% methanol in dichloromethane elute)

Sources & evidence

ORD record: ord-0f0c7f07f65f410eaa653a474b2765e5
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067914B1

Reaction notes

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