4-Chlorobenzoic Acid → HCID 67773228, compound
Reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[N:42]1([CH2:46][C@@H:47]([NH:51][CH2:52][CH3:53])[CH:48]([CH3:50])[CH3:49])[CH2:45][CH2:44][CH2:43]1>CN(C=O)C.C(Cl)Cl.C([O-])(O)=O.[Na+]>[N:42]1([CH2:46][C@@H:47]([N:51]([CH2:52][CH3:53])[C:6](=[O:8])[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)[CH:48]([CH3:50])[CH3:49])[CH2:45][CH2:44][CH2:43]1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
4-Chlorobenzoic acid (0.030 mL, 0.29 mmol), TBTU (113 mg, 0.35 mmol) and DIPEA (0.303 mL, 1.74 mmol) was stirred in DMF (2 mL). (S)-1-(azetidin-1-yl)-N-ethyl-3-methylbutan-2-amine (Compound V) (50 mg, 0.29 mmol) was added and the resultant mixture was stirred at rt overnight. The reaction mixture was diluted with DCM (10 mL) and NaHCO3 (saturated, 10 mL). The organic phase was isolated, filtered through a phase separator and concentrated under reduced pressure. The residue was purified by preparative HPLC to give the title compound (2.2 mg, 2%). Mixture of rotamers: 1H NMR (600 MHz, DMSO-d6) δ 0.63-1.32, 1.60-1.76, 1.82-1.98, 2.0-3.5 (omitted signals), 7.27-7.51. HRMS (M+H)+: calculated 309.1725. found 309.1734.
Workup
- customThe organic phase was isolated
- filtrationfiltered through a phase separator
- concentrationconcentrated under reduced pressure
- customThe residue was purified by preparative HPLC
Sources & evidence
- ORD record
- ord-ce690d4eb46c4b5d9ed48163688c0ba5
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08361998B2
Reaction notes
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