Benzyl (2-fluoro-4-{2-[3-methyl-3-(1-methylpiperidin-4-yl)ureido]pyridin-4-yloxy}phenyl)carbamate → 3-[4-(4-Amino-3-fluorophenoxy)pyridin-2-yl]-1-methyl-1-(1-methylpiperidin-4-yl)urea
Reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([N:18]([CH3:26])[CH:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)=[O:17])[CH:10]=2)[CH:5]=[CH:4][C:3]=1[NH:27]C(=O)OCC1C=CC=CC=1>O1CCCC1.[C].[Pd]>[NH2:27][C:3]1[CH:4]=[CH:5][C:6]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16](=[O:17])[N:18]([CH3:26])[CH:19]3[CH2:20][CH2:21][N:22]([CH3:25])[CH2:23][CH2:24]3)[CH:10]=2)=[CH:7][C:2]=1[F:1]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of benzyl (2-fluoro-4-{2-[3-methyl-3-(1-methylpiperidin-4-yl)ureido]pyridin-4-yloxy}phenyl)carbamate (110 mg) in tetrahydrofuran (10 ml) was 10% palladium carbon (46.2 mg), followed by stirring under a hydrogen atmosphere at room temperature for 18 hrs. The reaction mixture was filtered to remove the catalyst, which was then washed with tetrahydrofuran. The filtrate was dried over anhydrous sodium sulfate, and concentrated to a volume of 40 ml to give a solution of the target compound in tetrahydrofuran (40 ml) as a pale yellow solution. Assuming that the reaction preceded quantitatively, the solution was used for a next reaction.
Workup
- filtrationThe reaction mixture was filtered
- customto remove the catalyst, which
- washwas then washed with tetrahydrofuran
- dry with materialThe filtrate was dried over anhydrous sodium sulfate
- concentrationconcentrated to a volume of 40 ml
- customto give a solution of the target compound in tetrahydrofuran (40 ml) as a pale yellow solution
- customthe solution was used for a next reaction
Sources & evidence
- ORD record
- ord-8051baad5e114fcaa8b6cd4e5c03d663
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07531532B2
Reaction notes
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