4-Chloro-1,2-diaminobenzene → N-(2-amino-4-chlorophenyl)-4,4,4-trifluoro-3-hydroxy-3-methylbutanamide
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[CH:6][CH:7]=1.[F:10][C:11]([F:20])([F:19])[C:12]([OH:18])([CH3:17])[CH2:13][C:14](O)=[O:15].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>O.CN(C=O)C>[NH2:9][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=1[NH:8][C:14](=[O:15])[CH2:13][C:12]([OH:18])([CH3:17])[C:11]([F:20])([F:19])[F:10]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 4-chlorobenzene-1,2-diamine (1.32 g, 9.3 mmol), 4,4,4-trifluoro-3-hydroxy-3-methylbutanoic acid (1.6 g, 9.3 mmol), HATU (4.24 g, 11.2 mmol), DIPEA (3.1 mL, 18.6 mmol) and DMF (25 mL) was stirred at room temperature overnight. The mixture was diluted with water (150 mL), and then extracted with EtOAc (50 mL×3). The combined organic phases were washed with brine (50 mL), and then dried over Na2SO4, then filtered and concentrated. The residue was purified with flash column (30% EtOAc in PE to EtOAc) to give N-(2-amino-4-chlorophenyl)-4,4,4-trifluoro-3-hydroxy-3-methylbutanamide as brown oil (2.1 g, 76%).
Workup
- extractionextracted with EtOAc (50 mL×3)
- washThe combined organic phases were washed with brine (50 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified with flash column (30% EtOAc in PE to EtOAc)
Sources & evidence
- ORD record
- ord-48d24de882be453ba1e9a38caa36dca2
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09206191B2
Reaction notes
Loading…