3-((2-Cyanoethyl)disulfanyl)propanenitrile → 3-(3-Pyridin-3-yl-1H-pyrazol-4-ylsulfanyl)-propionitrile

HRID 1027522Notes

Reaction equation

HRID 1027522 reaction equation
[CH3:1][S:2][C:3]1[C:4]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)=[N:5][NH:6][CH:7]=1.[C:14]([CH2:16]CSSCCC#N)#[N:15].IC1C(C2C=NC=CC=2)=NNC=1>C(OCC)(=O)C>[N:10]1[CH:11]=[CH:12][CH:13]=[C:8]([C:4]2[C:3]([S:2][CH2:1][CH2:16][C:14]#[N:15])=[CH:7][NH:6][N:5]=2)[CH:9]=1

Participants

5

Reactant 3

HCID 2061013-((2-Cyanoethyl)disulfanyl)propanenitrileHCID 178503312HCID 178503312, compoundHCID 178506560HCID 178506560, compound2×

Product 1

HCID 1785112133-(3-Pyridin-3-yl-1H-pyrazol-4-ylsulfanyl)-propionitrileYield 62%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Compound 21R was prepared following the procedure as described for the synthesis of compound 21A (see Scheme 3) using 3-(2-cyano-ethyldisulfanyl)-propionitrile as the disulfide and 3-(4-iodo-1H-pyrazol-3-yl)-pyridine (compound 20B). (conditions flash chromatography (ethyl acetate)) Yield: 62%. (oil). 1H-NMR (200 MHz, CDCl3): δ 9.20 (d, J=2 Hz, 1H), 8.60 (dd, J=5 Hz, 2 Hz, 1H), 8.33 (dt, J=8 Hz, 2 Hz, 1H), 7.82 (s, 1H), 7.43-7.37 (m, 1H), 2.76 (t, J=7 Hz, 2H), 2.45 (t, J=7 Hz, 2H).

Sources & evidence

ORD record
ord-331bd04c7eb842e4a3165d6157b37898
Source dataset
uspto-grants-2014_05
Patent number
US08735388B2

Reaction notes

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