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

HRID 706503Notes

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-1c81f4c5c24b445bbc0f7416bfa8bf58
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174986B2

Reaction notes

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