Triethylamine → Tert-butyl 2-(2-cyano-6-(trifluoromethyl)quinolin-4-ylamino)acetate
Reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[N:5]=[C:4]([C:16]#[N:17])[CH:3]=1.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.Cl.[NH2:50][CH2:51][C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53]>O1CCOCC1>[C:16]([C:4]1[CH:3]=[C:2]([NH:50][CH2:51][C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[N:5]=1)#[N:17]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Into a 25 mL vial, was placed a solution of 4-hydroxy-6-(trifluoromethyl)quinoline-2-carbonitrile (238 mg, 1.00 mmol, 1.00 equiv) in dioxane (2 mL), PyBrOP (217 mg, 0.47 mmol, 1.10 equiv), triethylamine (354 mg, 3.50 mmol, 2.50 equiv) and tert-butyl 2-aminoacetate hydrochloride (217 mg, 1.30 mmol, 1.30 equiv). The reaction mixture was stirred overnight at room temperature. The reaction was then quenched by the addition of 25 mL of water. The resulting solution was extracted with 3×10 mL of ethyl acetate. The combined organic layers dried over anhydrous sodium sulfate and concentrated under vacuum. The residue purified by chromatography over a silica gel column with EtOAc/petroleum ether (1:1-1:10). The title compound was obtained as a white solid.
Workup
- customThe reaction was then quenched by the addition of 25 mL of water
- extractionThe resulting solution was extracted with 3×10 mL of ethyl acetate
- dry with materialThe combined organic layers dried over anhydrous sodium sulfate
- concentrationconcentrated under vacuum
- customThe residue purified by chromatography over a silica gel column with EtOAc/petroleum ether (1:1-1:10)
Sources & evidence
- ORD record
- ord-bd312c27fbc849f7ab97fea9dff9980e
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08518969B2
Reaction notes
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