2,6-Lutidine → HCID 59225852, compound
Reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3].Cl.C(N=C=NCCCN(C)C)C.ON1C2N=CC=CC=2N=N1.N1C(C)=CC=CC=1C.[Br:39][C:40]1[N:44]([C:45]2[C:54]3[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=3)[C:48]([C:55]#[N:56])=[CH:47][CH:46]=2)[C:43]([S:57][CH2:58][C:59](O)=[O:60])=[N:42][CH:41]=1>ClCCl>[Br:39][C:40]1[N:44]([C:45]2[C:54]3[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=3)[C:48]([C:55]#[N:56])=[CH:47][CH:46]=2)[C:43]([S:57][CH2:58][C:59]([NH:7][CH2:6][C:5]([O:4][CH2:2][CH3:3])=[O:8])=[O:60])=[N:42][CH:41]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
Glycine ethyl ester hydrochloride (76 mg, 0.541 mmol, 1.2 equiv.), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (130 mg, 0.676 mmol, 1.5 equiv.), 1-hydroxy-7-azabenzotriazole (92 mg, 0.676 mmol, 1.5 equiv.) and 2,6-lutidine (0.16 mL, 1.35 mmol, 3.0 equiv) were added to a solution of 2-(5-bromo-1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)acetic acid (175 mg, 0.451 mmol) in dichloromethane (2.25 mL) and stirred at room temperature for 18 hours. The crude product was purified by SGC (0-100% ethyl acetate/hexanes) to afford the title compound containing some 1-hydroxy-7-azabenzotriazole. The impure product was dissolved in ethyl acetate (50 mL), washed with aqueous HCl solution (0.1M, 2×30 mL), saturated aqueous NaHCO3 solution (30 mL), and saturated sodium chloride solution (30 mL). The organics were dried over sodium sulfate, filtered, and concentrated to afford ethyl 2-(2-(5-bromo-1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)acetamido)acetate as a yellow oil (199 mg, 93%).
Workup
- customThe crude product was purified by SGC (0-100% ethyl acetate/hexanes)
Sources & evidence
- ORD record
- ord-e0fca484ed78448695162fc115d5793a
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08193234B2
Reaction notes
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