Trifluoroacetic acid → N-(azetidin-3-yl)-2-((2-cyano-6-(trifluoromethyl)quinolin-4-yl)amino)acetamide
Reaction equation
[C:1]([C:3]1[CH:12]=[C:11]([NH:13][CH2:14][C:15]([NH:17][CH:18]2[CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19]2)=[O:16])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:29]([F:32])([F:31])[F:30])[CH:9]=2)[N:4]=1)#[N:2].C1(SC)C=CC=CC=1.FC(F)(F)C(O)=O>C(Cl)Cl.CCOCC>[NH:20]1[CH2:21][CH:18]([NH:17][C:15](=[O:16])[CH2:14][NH:13][C:11]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:29]([F:32])([F:31])[F:30])[CH:9]=3)[N:4]=[C:3]([C:1]#[N:2])[CH:12]=2)[CH2:19]1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of tert-butyl 3-(2-((2-cyano-6-(trifluoromethyl)quinolin-4-yl)amino)acetamido)azetidine-1-carboxylate (3.35 g, 7.45 mmol) from above step E, in DCM (50 mL) was treated with thioanisole (0.25 mL, 2 mmol) and stirred for 10 min and then treated with trifluoroacetic acid (50 mL) dropwise. The resulting opaque solution was stirred for 2.5 h at room temperature and diluted with Et2O (200 mL). Precipitate was formed. This mixture was cooled in the refrigerator and the solvent decanted (solid sticks to the flask). The solid was dried under high vacuum and recrystallized from iPrOH to give the title compound.
Workup
- stirringThe resulting opaque solution was stirred for 2.5 h at room temperature
- customPrecipitate was formed
- temperatureThis mixture was cooled in the refrigerator
- customthe solvent decanted (solid sticks to the flask)
- customThe solid was dried under high vacuum
- customrecrystallized from iPrOH
Sources & evidence
- ORD record
- ord-7664bd3099334cd0bcd4c31616f4c7e5
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09062048B2
Reaction notes
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