Triethylamine → HCID 117777986, compound

HRID 1503237Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[C:23]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][NH2:30])[CH:24]=1.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C>[C:23]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][NH:30][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][C:2]([Cl:1])=[N:3][CH:4]=2)[CH:24]=1

Participants

Conditions

Temperature: 100 °C

Procedure

6-Chloronicotinic acid (0.29 g) and 1,1′-carbonylbis(1H-imidazole) (0.34 g) were dissolved in N,N-dimethylformamide (5 mL), and the solution was heated with stirring at 100° C. for 45 minutes. The reaction solution was brought back to room temperature. 1-Biphenyl-3-ylmethanamine (0.37 g) and triethylamine (0.51 mL) were added thereto, and the mixture was stirred at 70° C. for 2 hours. Ethyl acetate was added thereto, and the organic layer was washed with water and dried over sodium sulfate. After concentration under reduced pressure, the obtained residue was purified by silica gel column chromatography (Moritex Corporation, elution solvent: hexane/ethyl acetate) to obtain the title compound (0.48 g) as a white solid (yield: 81%).

Workup

temperaturethe solution was heated
customwas brought back to room temperature
stirringthe mixture was stirred at 70° C. for 2 hours
washthe organic layer was washed with water
dry with materialdried over sodium sulfate
concentrationAfter concentration under reduced pressure
customthe obtained residue was purified by silica gel column chromatography (Moritex Corporation, elution solvent: hexane/ethyl acetate)

Sources & evidence

ORD record: ord-35eeefc3f7ad46a3be6d335f20238844
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212170B2

Reaction notes

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