Ammonia → 1-(4-Amino-2-(methoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol

HRID 1006636Notes

Reaction equation

Cl[C:2]1[C:11]([NH:12][C:13](=O)[CH2:14]COC)=[C:10]([NH:19][CH2:20][C:21]([OH:24])([CH3:23])[CH3:22])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH3:25].[CH3:26][OH:27]>O.C(=O)(O)[O-].[Na+]>[NH2:25][C:2]1[C:11]2[N:12]=[C:13]([CH2:14][O:27][CH3:26])[N:19]([CH2:20][C:21]([CH3:22])([CH3:23])[OH:24])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

Conditions

Temperature: 150 °C

Procedure

N-[2-Chloro-4-(2-hydroxy-2-methylpropyl)amino-3-quinolinyl]-3-methoxypropanamide (6 g, Example 110) was added to 5% ammonia in methanol (60 mL). The mixture was heated in a Parr bomb for 5 hours at approximately 150° C. The solvent was evaporated under vacuum to give a brown residue. The residue was diluted with water and sodium bicarbonate then extracted with ethyl acetate. The ethyl acetate extract was washed with water, dried over magnesium sulfate then evaporated to provide a tan solid. The solid was purified by silica gel chromatography to provide 1.64 g of the desired product as a solid, m.p. 174-175° C. Analysis: Calculated: %C, 65.0; %H, 7.0; %N, 17.8; Found: %C, 64.8; %H, 7.0; %N, 17.7.

Workup

customThe solvent was evaporated under vacuum
customto give a brown residue
extractionthen extracted with ethyl acetate
extractionThe ethyl acetate extract
washwas washed with water
dry with materialdried over magnesium sulfate
customthen evaporated
customto provide a tan solid
customThe solid was purified by silica gel chromatography

Sources & evidence

ORD record: ord-2120041e2e30474386919eb922a341d3
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06790961B2

Reaction notes

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