Acetic Acid Mixture with Hydrobromic Acid → HCID 23020383, compound
Reaction equation
[C:1]([C:3]1[CH:38]=[CH:37][CH:36]=[CH:35][C:4]=1[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:17]CC3C=CC(OC)=CC=3)[CH:12]=2)[N:8]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[C:7]1=[O:34])#[N:2].Br.C(O)(=O)C>>[NH2:17][C:13]1[CH:12]=[C:11]([C:9]2[N:8]([C:27]3[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=3)[C:7](=[O:34])[N:6]([CH2:5][C:4]3[CH:35]=[CH:36][CH:37]=[CH:38][C:3]=3[C:1]#[N:2])[CH:10]=2)[CH:16]=[CH:15][N:14]=1Participants
3
Conditions
- Temperature
- 70 °C
Procedure
To 1.5 g of 1-(2-cyanobenzyl)-3-(4-fluorophenyl)-4-[2-(4-methoxybenzylamino)pyridin-4-yl]-4-imidazolin-2-one (Compound of Example 5) was added 3 ml of 25% hydrogen bromide-acetic acid solution, and the mixture was stirred at 70° C. for one hour. The reaction mixture was concentrated under reduced pressure, and the residue was made alkali with an aqueous sodium bicarbonate solution. The mixture was extracted with ethyl acetate, washed with brine and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was purified by silica gel column chromatography (chloroform:methanol=20:1) to give 572 mg of the title compound as colorless crystal. Melting point:182-183° C.
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure
- extractionThe mixture was extracted with ethyl acetate
- washwashed with brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationAfter concentration under reduced pressure
- customthe residue was purified by silica gel column chromatography (chloroform:methanol=20:1)
Sources & evidence
- ORD record
- ord-e76274890d5540c2b833aa70fb7c230a
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07473695B2
Reaction notes
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