Triethylamine → (R)-3-(5-Methylpyridin-2-yl)-5-(methylsulfonyl)-N-(1-(6-(trifluoromethyl)pyridin-3-yl)ethyl)benzamide
Reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH:14]=[C:15]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:16]=2)[C:11]([OH:13])=O)=[N:6][CH:7]=1.[F:21][C:22]([F:33])([F:32])[C:23]1[N:28]=[CH:27][C:26]([C@H:29]([NH2:31])[CH3:30])=[CH:25][CH:24]=1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH:14]=[C:15]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:16]=2)[C:11]([NH:31][C@@H:29]([C:26]2[CH:27]=[N:28][C:23]([C:22]([F:33])([F:21])[F:32])=[CH:24][CH:25]=2)[CH3:30])=[O:13])=[N:6][CH:7]=1Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
Into a round-bottom flask were charged 3-(5-methylpyridin-2-yl)-5-(methylsulfonyl)benzoic acid (40% mixture with BaCl2, 250 mg, 0.34 mmol), (R)-1-(6-(trifluoromethyl)pyridin-3-yl)ethanamine (130 mg, 0.69 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (130 mg, 0.69 mmol), 1-hydroxybenzotriazole hydrate (100 mg, 0.69 mmol), triethylamine (87 mg, 0.86 mmol) and CH2Cl2 (3 mL). The mixture was stirred at room temperature overnight and then concentrated. The residue was purified via flash chromatography to afford the desired product as a white solid.
Workup
- concentrationconcentrated
- customThe residue was purified via flash chromatography
Sources & evidence
- ORD record
- ord-cd936445c35b4695a3afdb20056b77dc
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946439B2
Reaction notes
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