Sodium Hydroxide → 5-[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]pentanamide
Reaction equation
[NH2:1]C1C=NC2C(C=1NCCCCC(OCC)=O)=CC=CC=2.C(OCC(Cl)=O)C.[CH2:29]([O:31][CH2:32][C:33]1[N:34]([CH2:46][CH2:47][CH2:48][CH2:49][C:50](OCC)=[O:51])[C:35]2[C:44]3[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=3[N:38]=[CH:37][C:36]=2[N:45]=1)[CH3:30].C([O-])(=O)C.[NH4+].[OH-].[Na+]>>[CH2:29]([O:31][CH2:32][C:33]1[N:34]([CH2:46][CH2:47][CH2:48][CH2:49][C:50]([NH2:1])=[O:51])[C:35]2[C:44]3[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=3[N:38]=[CH:37][C:36]=2[N:45]=1)[CH3:30]Participants
Reactant 5
Product 1
Conditions
- Temperature
- 110 °C
Procedure
Ethyl 5-(3-aminoquinolin-4-ylamino)pentanoate, prepared in Parts A and B of Example 34, was treated as described in Part A of Example 36. Ethoxyacetyl chloride was used instead of methoxypropionyl chloride. Ethyl 5-(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanoate (6.0 g, 17 mmol) and ammonium acetate (15 g) were sealed in a high-pressure vessel and heated for four days at 110° C. and then allowed to cool to ambient temperature. Aqueous sodium hydroxide (10%) was added, and the mixture was then extracted with dichloromethane (3×). The product crystallized from the dichloromethane and was collected in two crops to provide 2.64 g of 5-[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]pentanamide as an off-white solid, mp 157-158° C.
Workup
- additionwas treated
- temperatureto cool to ambient temperature
- extractionthe mixture was then extracted with dichloromethane (3×)
- customThe product crystallized from the dichloromethane
- customwas collected in two crops
Sources & evidence
- ORD record
- ord-fd480d040bde401587d2a14048ee60f1
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08697873B2
Reaction notes
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