Hydrochloric Acid → 1-(4-Amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-yl 2-aminoacetate
Reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][C:13]([O:15][C:16]([CH3:47])([CH3:46])[CH2:17][N:18]1[C:30]2[C:29]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[N:23]=[C:22]([N:31]3C(=O)C4C(=CC=CC=4)C3=O)[C:21]=2[N:20]=[C:19]1[CH2:42][O:43][CH2:44][CH3:45])=[O:14].NN.O.Cl>C(Cl)Cl.C1COCC1>[NH2:3][CH2:12][C:13]([O:15][C:16]([CH3:46])([CH3:47])[CH2:17][N:18]1[C:30]2[C:29]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[N:23]=[C:22]([NH2:31])[C:21]=2[N:20]=[C:19]1[CH2:42][O:43][CH2:44][CH3:45])=[O:14]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
1-(4-(1,3-Dioxoisoindolin-2-yl)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-yl 2-(1,3-dioxoisoindolin-2-yl)acetate (300 mg, 475 μmol) was combined with THF (5 mL) to give a white suspension. To this suspension was added hydrazine in water (1000 μl, 11.2 mmol) and the solution was stirred for 0.75 hour at room temperature. The mixture was cooled to 0° C., 1N hydrochloric acid (30 mL) and DCM (50 mL) were added. The white precipitate a (phtalylhydrazide) was removed by filtration and the organic phase was discarded. The aqueous phase was lyophilized and the residue was taken up with acetonitrile (20 mL) and DIEA (pH 10). After evaporation of solvent, the residue was purified by preparative HPLC (Gemini NX 3u 50×4.6mm; acetonitrile/water/Et3N) to give the title compound (111 mg, 63%) as amorphous white solid; LC-MS (UV peak area, ESI) 99%, 372.4 (MH+).
Workup
- customto give a white suspension
- temperatureThe mixture was cooled to 0° C.
- customThe white precipitate a (phtalylhydrazide) was removed by filtration
- customAfter evaporation of solvent
- customthe residue was purified by preparative HPLC (Gemini NX 3u 50×4.6mm; acetonitrile/water/Et3N)
Sources & evidence
- ORD record
- ord-c7db16d9d773462e94a580f3e67d7cfd
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09447097B2
Reaction notes
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