4-Methylmorpholine → HCID 67773853, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([OH:7])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN1CCOCC1.[F:41][C:42]1([F:55])[CH2:47][CH2:46][CH2:45][N:44]([CH2:48][C@@H:49]([NH:53][CH3:54])[CH:50]([CH3:52])[CH3:51])[CH2:43]1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([N:53]([C@@H:49]([CH:50]([CH3:52])[CH3:51])[CH2:48][N:44]1[CH2:45][CH2:46][CH2:47][C:42]([F:55])([F:41])[CH2:43]1)[CH3:54])=[O:7]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
3-Chloro-4-fluorobenzoic acid (0.087 g, 0.50 mmol), TBTU (0.175 g, 0.54 mmol) and NMM (0.125 mL, 1.13 mmol) was mixed in DMF (2 mL). After 10 min at rt was (S)-1-(3,3-difluoropiperidin-1-yl)-N,3-dimethylbutan-2-amine (Compound S2) (0.1 g, 0.45 mmol) and additional DMF (1 mL) added. The resultant mixture was stirred at rt overnight. The mixture was concentrated and the residue dissolved in DCM (5 mL). The organic phase was washed with NaHCO3 (saturated, 5 mL), filtered through a phase separator and concentrated under reduced pressure. The residue was purified by preparative HPLC to give the title compound (80 mg, 47%). HRMS (M+H)+: calculated 377.1607. found 377.1613.
Workup
- concentrationThe mixture was concentrated
- dissolutionthe residue dissolved in DCM (5 mL)
- washThe organic phase was washed with NaHCO3 (saturated, 5 mL)
- filtrationfiltered through a phase separator
- concentrationconcentrated under reduced pressure
- customThe residue was purified by preparative HPLC
Sources & evidence
- ORD record
- ord-53644f506d164290aeab4a5cef95bad2
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08361998B2
Reaction notes
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