(S)-tert-butyl 1-(2-(cyclopropylamino)-3-fluorophenylamino)-1-oxopropan-2-ylcarbamate → (S)-1-(1-cyclopropyl-7-fluoro-1H-benzo[d]imidazol-2-yl)ethanamine
Reaction equation
[CH:1]1([NH:4][C:5]2[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:6]=2[NH:12][C:13](=O)[C@@H:14]([NH:16]C(=O)OC(C)(C)C)[CH3:15])[CH2:3][CH2:2]1>CC(O)=O>[CH:1]1([N:4]2[C:5]3[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:6]=3[N:12]=[C:13]2[C@@H:14]([NH2:16])[CH3:15])[CH2:3][CH2:2]1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A stirred solution of (S)-tert-butyl 1-(2-(cyclopropylamino)-3-fluorophenylamino)-1-oxopropan-2-ylcarbamate (651.7 mg, 1.932 mmol) in AcOH (20 mL) was heated at 60° C. for 30 min, after being concentrated under reduced pressure, the residue was subjected to 4 M HCl in 1,4-Dioxane (20 mL). The resultant mixture was stirred at rt for 40 min. The mixture was concentrated under reduced pressure and dissolved in water (5 mL) and then basified with 1 N NaOH to pH 9.5. The mixture was concentrated under reduced pressure and triturated with MeOH-CDM (1:1). The crude product was purified by column chromatography on a silica gel column using DCM-MeOH—NH4OH (9:1:0.05) as eluent to give (S)-1-(1-cyclopropyl-7-fluoro-1H-benzo[d]imidazol-2-yl)ethanamine: LC-MS (ESI) m/z 220.0 [M+H]+.
Workup
- concentrationafter being concentrated under reduced pressure
- concentrationThe mixture was concentrated under reduced pressure
- dissolutiondissolved in water (5 mL)
- concentrationThe mixture was concentrated under reduced pressure
- customtriturated with MeOH-CDM (1:1)
- customThe crude product was purified by column chromatography on a silica gel column
Sources & evidence
- ORD record
- ord-9deb13ecd48c454e9083b43b29d9e5a3
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08575183B2
Reaction notes
Loading…