Triethylamine → HCID 71667229, compound
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[C:12]([OH:14])=O.ClC(N(C)C)=C(C)C.FC(F)(F)C(O)=O.[NH2:30][CH2:31][C:32]([N:34]1[CH2:38][CH2:37][CH2:36][C@H:35]1[C:39]#[N:40])=[O:33].C(N(CC)CC)C>C(Cl)Cl.C1COCC1>[C:39]([C@@H:35]1[CH2:36][CH2:37][CH2:38][N:34]1[C:32](=[O:33])[CH2:31][NH:30][C:12]([C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=2)[N:8]=[CH:7][CH:6]=1)=[O:14])#[N:40]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
6-Fluoroquinoline-4-carboxylic acid (17) (0.054 g, 0.282 mmol) was dissolved in a 1:1 mixture of dry DCM and THF (5 mL). 1-chloro-N,N,2-trimethylprop-1-en-1-amine (0.052 mL, 0.395 mmol) was added to this solution, and the mixture was stirred for 30 minutes at rt. Then, a solution of (S)-1-(2-aminoacetyl)pyrrolidine-2-carbonitrile 2,2,2-trifluoroacetate (0.075 g, 0.282 mmol) prepared as described in general procedure B and triethylamine (80 μL, 0.571 mmol) in 3 mL dry THF was added, and the mixture was stirred for 2 h. After evaporation of volatiles, the residue was dissolved in DCM (15 mL), washed with saturated sodium bicarbonate and brine. The organic layer was dried over sodium sulfate, filtrated and purified using flash chromatography (95-5 ethyl acetate-methanol) to yield white crystals
Workup
- additionwas added
- stirringthe mixture was stirred for 2 h
- customAfter evaporation of volatiles
- dissolutionthe residue was dissolved in DCM (15 mL)
- washwashed with saturated sodium bicarbonate and brine
- dry with materialThe organic layer was dried over sodium sulfate
- filtrationfiltrated
- custompurified
- customto yield white crystals
Sources & evidence
- ORD record
- ord-b0d19142e60e4fe98e8acfc0cd9842f7
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09346814B2
Reaction notes
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