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Pyrazole → 2-ethoxymethyl-1-(3-methoxypropyl)-7-(pyrazol-1-yl)-1H-imidazo[4,5-c]quinolin-4-amine

HRID 9468
Notes
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Reaction equation

HRID 9468 reaction equation
P([O-])([O-])([O-])=O.[K+].[K+].[K+].[NH:9]1[CH:13]=[CH:12][CH:11]=[N:10]1.Br[C:15]1[CH:16]=[CH:17][C:18]2[C:19]3[N:28]([CH2:29][CH2:30][CH2:31][O:32][CH3:33])[C:27]([CH2:34][O:35][CH2:36][CH3:37])=[N:26][C:20]=3[C:21]([NH2:25])=[N:22][C:23]=2[CH:24]=1.N[C@@H]1CCCC[C@H]1N>[Cu]I.O1CCOCC1>[CH2:36]([O:35][CH2:34][C:27]1[N:28]([CH2:29][CH2:30][CH2:31][O:32][CH3:33])[C:19]2[C:18]3[CH:17]=[CH:16][C:15]([N:9]4[CH:13]=[CH:12][CH:11]=[N:10]4)=[CH:24][C:23]=3[N:22]=[C:21]([NH2:25])[C:20]=2[N:26]=1)[CH3:37]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 1048PyrazoleHCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 219840707-bromo-2-ethoxymethyl-1-(3-methoxypropyl)-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 219842812-ethoxymethyl-1-(3-methoxypropyl)-7-(pyrazol-1-yl)-1H-imidazo[4,5-c]quinolin-4-amineYield 25%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Procedure

A 4 dram vial containing a stir bar was charged sequentially with copper(I) iodide (0.038 g), potassium phosphate (0.890 g), pyrazole (0.164 g), 7-bromo-2-ethoxymethyl-1-(3-methoxypropyl)-1H-imidazo[4,5-c]quinolin-4-amine (0.786 g), (±)-trans-1,2-diaminocyclohexane (0.030 mL), and anhydrous 1,4-dioxane (2 mL). The vial was flushed with nitrogen, capped, and placed in an oil bath at 110° C. After 15.5 hours, the reaction was cooled to room temperature and purified by flash column chromatography using a gradient of CMA/chloroform as the eluent. Subsequent recrystallization from acetonitrile yielded 0.190 g of 2-ethoxymethyl-1-(3-methoxypropyl)-7-(pyrazol-1-yl)-1H-imidazo[4,5-c]quinolin-4-amine as a white solid, mp 159.0–160.0° C.

Workup

  1. additionA 4 dram vial containing a stir bar
  2. customThe vial was flushed with nitrogen
  3. customcapped
  4. customplaced in an oil bath at 110° C
  5. custompurified by flash column chromatography
  6. customSubsequent recrystallization from acetonitrile

Sources & evidence

ORD record
ord-a0b7a3a3e0674a5c922c7e18e8da34dc
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07091214B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes