Triethylamine → 5-Cyano-N-[4-(2-furyl)-5-(tetrahydropyran-4-ylcarbonyl)thiazol-2-yl]furan-2-carboxamide

HRID 2238802Notes

Reaction equation

[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:7]=[C:8]([NH:19][C:20]([CH:22]2[CH:26]=[CH:25][C:24](=NO)[O:23]2)=[O:21])[S:9][C:10]=1[C:11]([CH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)=[O:12].[CH2:29]([N:31](CC)CC)C.[Cl-].ClC1N(C)CC[NH+]1C.C(=O)([O-])O.[Na+]>ClCCl>[C:29]([C:24]1[O:23][C:22]([C:20]([NH:19][C:8]2[S:9][C:10]([C:11]([CH:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)=[O:12])=[C:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)[N:7]=2)=[O:21])=[CH:26][CH:25]=1)#[N:31]

Participants

Conditions

Temperature: 0 °C

Procedure

Compound 514 (2.08 g, 5.00 mmol) and triethylamine (0.836 mL, 6.00 mmol) were suspended in dichloromethane (20 mL), and 2-chloro-1,3-dimethylimidazolinium chloride (2.03 g, 12.0 mmol) was added thereto at 0° C. This was stirred at 0° C. for 30 minutes, and then triethylamine (0.836 mL, 6.00 mmol) was added thereto, followed by stirring at 0° C. for 5 minutes. Aqueous saturated sodium hydrogencarbonate solution was added to the reaction mixture, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (chloroform:methanol=49:1), followed by recrystallizing from a mixed solvent (3:1) of ethanol and water to afford the entitled Compound 515 (1.26 g, 63%) as a pale brown solid.

Workup

customat 0° C
stirringby stirring at 0° C. for 5 minutes
extractionfollowed by extraction with chloroform
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
distillationthe solvent was distilled away under reduced pressure
customThe resulting residue was purified through silica gel column chromatography (chloroform:methanol=49:1)
customby recrystallizing from a mixed solvent (3:1) of ethanol and water

Sources & evidence

ORD record: ord-f4390c1c3e2a4822a2e06b8cc74de598
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07718808B2

Reaction notes

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