Hydrochloric Acid → 3-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]propane-1,2-diol
Reaction equation
Cl.CC1(C)[O:7][CH:6]([CH2:8][N:9]2[C:21]3[C:20]4[CH:19]=[CH:18][C:17]([C:22]5[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=5)=[CH:16][C:15]=4[N:14]=[C:13]([NH2:28])[C:12]=3[N:11]=[C:10]2[CH2:29][O:30][CH2:31][CH3:32])[CH2:5][O:4]1>C1COCC1>[NH2:28][C:13]1[C:12]2[N:11]=[C:10]([CH2:29][O:30][CH2:31][CH3:32])[N:9]([CH2:8][CH:6]([OH:7])[CH2:5][OH:4])[C:21]=2[C:20]2[CH:19]=[CH:18][C:17]([C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)=[CH:16][C:15]=2[N:14]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Hydrochloric acid (12 mL of 1 N) was added to a solution of 1-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine (0.75 g, 1.73 mmol) in THF, and the reaction was stirred overnight at ambient temperature. The THF was removed under reduced pressure, and 1% aqueous sodium hydroxide was added to the remaining solution to adjust to pH 9. A precipitate formed, was isolated by filtration, washed with water, and dried in an oven at 60° C. to provide 0.61 g of 3-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]propane-1,2-diol as a white solid, mp 218–220° C.
Workup
- customThe THF was removed under reduced pressure, and 1% aqueous sodium hydroxide
- additionwas added to the remaining solution
- customA precipitate formed
- customwas isolated by filtration
- washwashed with water
- customdried in an oven at 60° C.
Sources & evidence
- ORD record
- ord-64210660bf0948f5bd7e03f4a92c51a0
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07091214B2
Reaction notes
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