Water → 1-[7-bromo-2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]-2-methylpropan-2-ol

HRID 598014Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].O.Cl.[Br:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([NH:27][CH2:28][C:29]([OH:32])([CH3:31])[CH3:30])=[C:15]([NH:20][C:21](=O)[CH2:22][O:23][CH2:24][CH3:25])[CH:16]=[N:17]2)=[N:12][CH:11]=1>C(O)C>[Br:9][C:10]1[CH:11]=[N:12][C:13]2[C:14]3[N:27]([CH2:28][C:29]([CH3:31])([OH:32])[CH3:30])[C:21]([CH2:22][O:23][CH2:24][CH3:25])=[N:20][C:15]=3[CH:16]=[N:17][C:18]=2[CH:19]=1

Participants

Conditions

Temperature: 77 °C

Procedure

Potassium carbonate (113 g) and deionized water (565 mL) were sequentially added to a solution of N-{7-bromo-4-[(2-hydroxy-2-methylpropyl)amino][1,5]naphthyridin-3-yl}-2-ethoxyacetamide hydrochloride (113 g, 261 mmol) in denatured ethanol (1.695 L), and the resulting mixture was heated at reflux (77° C.) overnight and allowed to cool to room temperature. The ethanol was removed under reduced pressure, and the resulting mixture was filtered to isolate a solid. The solid was washed with deionized water (100 mL) and dried over two nights in a vacuum oven at 40° C. to provide 90 g of 1-[7-bromo-2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]-2-methylpropan-2-ol as a brown solid. Material from a separate run was used in the next step.

Workup

temperaturethe resulting mixture was heated
temperatureto cool to room temperature
customThe ethanol was removed under reduced pressure
filtrationthe resulting mixture was filtered
customto isolate a solid
washThe solid was washed with deionized water (100 mL)
customdried over two nights in a vacuum oven at 40° C.

Sources & evidence

ORD record: ord-713d03a22cac4dae8ceb36409ba3dd3d
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897609B2

Reaction notes

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