Acetonitrile → HCID 73347360, compound
Reaction equation
[OH:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[C:12]([OH:14])=O)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH2:15]([N:17](C(C)C)C(C)C)C.N1([C:29]([N:31]2[CH:35]=[CH:34][N:33]=[CH:32]2)=[O:30])C=CN=C1.[C:36](#N)[CH3:37]>>[C:34]([C@@H:35]1[CH2:37][CH2:36][CH2:32][N:31]1[C:29](=[O:30])[CH2:15][NH:17][C:12]([C:11]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[OH:1])=[O:14])#[N:33]Participants
Conditions
- Temperature
- 75 °C
Procedure
To a 50 mL round bottom flask, was added 3-hydroxyquinoline-4-carboxylic acid (0.1 g, 0.529 mmol), acetonitrile (Volume: 10 ml) and N-ethyl-N-isopropylpropan-2-amine (0.157 g, 1.216 mmol) at room temperature with stirring until a solution was observed. Then, di(1H-imidazol-1-yl)methanone (0.094 g, 0.581 mmol) was added in one portion and the mixture was held for 4 h. Then the amine(S)-1-(2-aminoacetyl)pyrrolidine-2-carbonitrile 2,2,2-trifluoroacetate (0.198 g, 0.740 mmol) was added in one portion. The mixture was heated to 75° C., held at 75° C. for 5 h, cooled to room temperature, and stirred at room temperature overnight. The volatiles were evaporated and the residue was redissolved in EtOAc, washed with 0.3N citric acid, saturated sodium bicarbonate, brine, dried over sodium sulfate, filtered and evaporated. The crude product was purified using column chromatography with ethyl acetate-methanol (95-5) mixture to yield the product (0.076 g, 44%)
Workup
- waitheld at 75° C. for 5 h
- temperaturecooled to room temperature
- stirringstirred at room temperature overnight
- customThe volatiles were evaporated
- dissolutionthe residue was redissolved in EtOAc
- washwashed with 0.3N citric acid, saturated sodium bicarbonate, brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- customevaporated
- customThe crude product was purified
Sources & evidence
- ORD record
- ord-3d035ccdedcf45aeb99bd4adca893205
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09346814B2
Reaction notes
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