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

HRID 909361Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].Cl.[Br:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:26][CH2:27][C:28]([OH:31])([CH3:30])[CH3:29])=[C:14]([NH:19][C:20](=O)[CH2:21][O:22][CH2:23][CH3:24])[CH:15]=[N:16]2)=[N:11][CH:10]=1>C(O)C>[Br:8][C:9]1[CH:10]=[N:11][C:12]2[C:13]3[N:26]([CH2:27][C:28]([CH3:30])([OH:31])[CH3:29])[C:20]([CH2:21][O:22][CH2:23][CH3:24])=[N:19][C:14]=3[CH:15]=[N:16][C:17]=2[CH:18]=1

Participants

Conditions

Temperature: 77 °C

Procedure

Potassium carbonate (113 g) 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 washed with 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.

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 washed with water (100 mL)
customdried over two nights in a vacuum oven at 40° C.

Sources & evidence

ORD record: ord-135db7dfb4414fdd9349cfe2a0f664cc
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017779B2

Reaction notes

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