Ammonia → HCID 57447077, compound
Reaction equation
[NH3:1].[CH2:2]([O:4][CH2:5][C:6]1[N:7]([CH2:19][CH2:20][CH2:21][C:22](Cl)=[O:23])[C:8]2[C:17]3[N:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:18]=1)[CH3:3]>O1CCOCC1.ClCCl>[CH2:2]([O:4][CH2:5][C:6]1[N:7]([CH2:19][CH2:20][CH2:21][C:22]([NH2:1])=[O:23])[C:8]2[C:17]3[N:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:18]=1)[CH3:3]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of ammonia in dioxane (33 mL of 0.5 M) was added to a solution of 4-[2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]butanoyl chloride (4.64 mmol, prepared as described in Parts A and B of Example 38) in dichloromethane (20 mL), and the reaction was stirred overnight at ambient temperature. An analysis by HPLC indicated the reaction was incomplete; ammonia gas was bubbled through the solution for 10 minutes. The reaction was then stirred for one hour and concentrated under reduced pressure. The residue was triturated with water and isolated by filtration to provide 1.02 g of 4-[2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]butanamide. The filtrate was extracted with dichloromethane (3×20 mL), and the combined extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide an additional 0.39 g of product. The combined solids were mixed with material from another run.
Workup
- customammonia gas was bubbled through the solution for 10 minutes
- stirringThe reaction was then stirred for one hour
- concentrationconcentrated under reduced pressure
- customThe residue was triturated with water
- customisolated by filtration
Sources & evidence
- ORD record
- ord-e9cc9b085b214b65a9535f1a518a3450
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08697873B2
Reaction notes
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