Sodium Iodide → HCID 58833698, compound
Reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][N:12]([CH3:16])[CH2:11]1.[I-].[Na+].[OH:19][C:20]1[CH:29]=[CH:28][C:27]2[N:26]=[C:25]([NH2:30])[C:24]3[N:31]=[C:32]([CH2:37][O:38][CH3:39])[N:33]([CH2:34][CH2:35][CH3:36])[C:23]=3[C:22]=2[CH:21]=1>CC(C)=O>[CH3:39][O:38][CH2:37][C:32]1[N:33]([CH2:34][CH2:35][CH3:36])[C:23]2[C:22]3[CH:21]=[C:20]([O:19][CH2:9][CH:10]4[CH2:15][CH2:14][CH2:13][N:12]([CH3:16])[CH2:11]4)[CH:29]=[CH:28][C:27]=3[N:26]=[C:25]([NH2:30])[C:24]=2[N:31]=1Participants
Procedure
Potassium carbonate (1.48 g, 10.75 mmol), 3-chloromethyl-1-methyl-piperidine hydrochloride (483 mg, 2.62 mmol), sodium iodide (100 mg, 0.66 mmol), and 8-hydroxy-2-methoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine (500 mg, 1.75 mmol) were combined in acetone and heated at reflux overnight. No desired product was detected and the reaction mixture was filtered. The filtrate was concentrated under reduced pressure, dissolved in DMF, and heated at 90° C. overnight. The reaction mixture was then cooled to ambient temperature, filtered, and concentrated under reduced pressure to provide a dark oil. The oil was dissolved in dichloromethane, filtered, purified by chromatography on a HORIZON HPFC system (eluted with a gradient of CMA:chloroform from 0:100 to 35:65), and crystallized from acetonitrile to afford 160 mg of 2-methoxymethyl-8-(1-methyl-piperidin-3-yl-methoxy)-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine as a tan powder, mp 194-196° C.
Workup
- temperatureheated
- temperatureat reflux overnight
Sources & evidence
- ORD record
- ord-5585c70e3f2a4f56bdcf5eeef71b2068
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365567B2
Reaction notes
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