Reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[F:11].[NH2:12][CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH3:20])[CH2:15][CH2:14]1.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>CC(N(C)C)=O>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:12][CH:13]2[CH2:18][CH2:17][N:16]([CH2:19][CH3:20])[CH2:15][CH2:14]2)=[O:8])=[CH:4][C:3]=1[F:11]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
4-amino-3-fluorobenzoic acid (2.115 g, 13.6 mmol), 4-Amino-1-Ethyl Piperidine (Fluorochem; 1.923 g, 15 mmol), HATU (5.7 g, 15 mmol) and DIPEA (7.1 mL, 40.8 mmol) were combined in DMA (60 mL) and the resulting yellow solution stirred at room temperature for 20 minutes. The reaction was left over the weekend at room temperature, solvent evaporated and the residue dissolved in methanol (10 mL) and loaded onto an SCX-2 column (50 g) which pre-wet with MeOH (40 mL), flushed with MeOH (4×30 ml) and eluted with 7N ammonia in MeOH (4×30 mL). Product containing, ammoniacal fractions were combined to yield the title compound as a brown solid (0.819 g, 22%)
Workup
- waitThe reaction was left over the weekend at room temperature
- customsolvent evaporated
- dissolutionthe residue dissolved in methanol (10 mL)
- customflushed with MeOH (4×30 ml)
- washeluted with 7N ammonia in MeOH (4×30 mL)
- additionProduct containing
Sources & evidence
- ORD record
- ord-60cb88dc051744b899d25578ed6a4372
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07709471B2
Linked notes
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