Potassium Carbonate → 2-{[(6-Chloro(3-pyridyl))methyl][2-(2-ethylthio-3-nitropyrrolyl)ethyl]amino}ethanenitrile
Reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8]C(NCCCl)C#N)=[CH:4][CH:3]=1.[CH2:16]([S:18][C:19]1[NH:20][CH:21]=[CH:22][C:23]=1[N+:24]([O-:26])=[O:25])[CH3:17].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:20]([CH2:21][CH2:22][C:22]2[C:23]([N+:24]([O-:26])=[O:25])=[C:19]([S:18][CH2:16][CH3:17])[NH:20][CH:21]=2)[CH2:19][C:23]#[N:24])=[CH:4][CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
This compound was prepared in a manner analogous to that set forth in Step G of Example 1, using 0.17 gram (0.0007 mole) of 2-{[(6-chloro(3-pyridyl)methyl] (2-chloroethylamino}ethanenitrile (prepared in Steps A and B of the present Example), 0.10 gram (0.00064 mole) of 2-ethylthio-3-nitropyrrole and 0.22 gram (0.0016 mole) of potassium carbonate in about 15 mL of DMF. The crude product was purified with column chromatography on silica gel. Elution was accomplished using 50% hexane in diethyl ether and 100% diethyl ether as eluants. The appropriate fractions were combined and concentrated under reduced pressure, yielding 0.10 gram of Compound I. The NMR spectrum was consistent with the proposed structure.
Workup
- customThis compound was prepared in a manner analogous to that set forth in Step G of Example 1
- customThe crude product was purified with column chromatography on silica gel
- washElution
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-ca0ddb384ff64c89a57728bcc045cb4e
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07943642B2
Reaction notes
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