4-Chlorobenzoic Acid → HCID 67772438, compound
Reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.[CH3:11]N(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN1CCOCC1.[N:40]1([CH2:44][C@@H:45]([NH:49][CH3:50])[CH2:46][CH2:47]C)[CH2:43][CH2:42][CH2:41]1>CN(C=O)C>[N:40]1([CH2:44][C@@H:45]([N:49]([CH3:50])[C:6](=[O:8])[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)[CH:46]([CH3:47])[CH3:11])[CH2:41][CH2:42][CH2:43]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
4-Chlorobenzoic acid (1.300 mL, 12.80 mmol) and TBTU (4.31 g, 13.44 mmol) was mixed in DMF (35 mL). The mixture was cooled to 0° C. and NMM (1.689 mL, 15.36 mmol) was dropwise added. After 10 min at 0° C. was (S)-1-(azetidin-1-yl)-N-methylpentan-2-amine (Compound J1) (2 g, 12.80 mmol) added. The resultant mixture was stirred at 0° C. for 30 min and at rt for 16 h. The mixture was concentrated and the residue dissolved in DCM (25 mL). The organic phase was washed with NaHCO3 (saturated, 2×50 mL), and brine (50 mL), filtered through a phase separator and concentrated under reduced pressure. The residue was purified by preparative HPLC to give the title compound (2.49 g, 66%).
Workup
- concentrationThe mixture was concentrated
- dissolutionthe residue dissolved in DCM (25 mL)
- washThe organic phase was washed with NaHCO3 (saturated, 2×50 mL), and brine (50 mL)
- filtrationfiltered through a phase separator
- concentrationconcentrated under reduced pressure
- customThe residue was purified by preparative HPLC
Sources & evidence
- ORD record
- ord-601fb141b45d43cd91f5001fe09a9d46
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08361998B2
Reaction notes
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