Triethylamine → HCID 53308148, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18](=[O:26])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C:14](O)=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C.[CH3:56][C@H:57]1[CH2:62][CH2:61][CH2:60][C@@H:59]([CH3:63])[NH:58]1>CN(C)C=O>[Cl:25][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][CH:22]=1)[C:18]([NH:17][C:4]1[C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]([N:58]3[C@H:59]([CH3:63])[CH2:60][CH2:61][CH2:62][C@@H:57]3[CH3:56])=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)=[O:26]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 0.040 g (0.11 mmol) of 5′-chloro-3′-(3-chloro-benzoylamino)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid in N,N-dimethylformamide (2 mL) is added 0.048 g (0.15 mmol) of O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate followed by 0.042 mL (0.304 mmol) of triethylamine. The mixture is stirred at room temperature for 1 h then 0.034 g (0.304 mmol) of cis-2,6-dimethylpiperidine is added and the mixture is stirred at room temperature overnight. The mixture is concentrated under reduced pressure and the residue is purified by preparative reverse phase HPLC to provide 0.002 g (4%) of the title compound (273) as a white solid. [M+H]+=489.2.
Workup
- stirringthe mixture is stirred at room temperature overnight
- concentrationThe mixture is concentrated under reduced pressure
- customthe residue is purified by preparative reverse phase HPLC
Sources & evidence
- ORD record
- ord-07fdedc4548745b289e30766a18805e6
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952004B2
Reaction notes
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