Acetic Acid → HCID 67387573, compound
Reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][OH:8])=[CH:3][CH:2]=1.[Li+].CC([N-]C(C)C)C.[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][N:27]([C:30]2[C:35](Cl)=[N:34][C:33]([C:37]#[N:38])=[C:32]([C:39]#[N:40])[N:31]=2)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18].C(O)(=O)C>C1COCC1>[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][N:27]([C:30]2[C:35]([O:8][CH2:7][C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)=[N:34][C:33]([C:37]#[N:38])=[C:32]([C:39]#[N:40])[N:31]=2)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 4-pyridylcarbinol (0.44 mmol, 45 mg) and anhydrous tetrahydrofuran (3 ml) cooled at 0° C. was added LDA (2M, 0.6 mmol, 300 ul). The mixture was stirred at 0° C. for 15 minutes. A solution of 3′-Chloro-5′,6′-dicyano-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid tert-butyl ester (0.29 mmol, 100 mg) in THF (2 ml) was then added to the cold mixture and stirred at 0° C. for 1 hour. Reaction mixture was poured onto 0.5M acetic acid and extracted with ethyl acetate. The crude product was purified by column chromatograph on silica using 70% EtOAc/hexanes to yield product 5′,6′-Dicyano-3′-(pyridin-4-ylmethoxy)-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid tert-butyl ester (100 mg).
Workup
- stirringstirred at 0° C. for 1 hour
- customReaction mixture
- extractionextracted with ethyl acetate
- customThe crude product was purified by column chromatograph on silica using 70% EtOAc/hexanes
Sources & evidence
- ORD record
- ord-75292c197f004ec39d8049fc9af421bd
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08013156B2
Reaction notes
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