Tert-butyl (1-{4-cyano-2-ethoxy-5-methyl-3-[5-(methylsulfonyl)pyridin-3-yl]phenyl}ethyl)carbamate → 4-(1-Aminoethyl)-3-ethoxy-6-methyl-2-[5-(methylsulfonyl)pyridin-3-yl]benzonitrile

HRID 510995Notes

Reaction equation

HRID 510995 reaction equation
[C:1]([C:3]1[C:8]([CH3:9])=[CH:7][C:6]([CH:10]([NH:12]C(=O)OC(C)(C)C)[CH3:11])=[C:5]([O:20][CH2:21][CH3:22])[C:4]=1[C:23]1[CH:24]=[N:25][CH:26]=[C:27]([S:29]([CH3:32])(=[O:31])=[O:30])[CH:28]=1)#[N:2]>Cl.O1CCOCC1>[NH2:12][CH:10]([C:6]1[CH:7]=[C:8]([CH3:9])[C:3]([C:1]#[N:2])=[C:4]([C:23]2[CH:24]=[N:25][CH:26]=[C:27]([S:29]([CH3:32])(=[O:31])=[O:30])[CH:28]=2)[C:5]=1[O:20][CH2:21][CH3:22])[CH3:11]

Participants

4

Reactant 1

HCID 86666909Tert-butyl (1-{4-cyano-2-ethoxy-5-methyl-3-[5-(methylsulfonyl)pyridin-3-yl]phenyl}ethyl)carbamate

Product 1

HCID 866669104-(1-Aminoethyl)-3-ethoxy-6-methyl-2-[5-(methylsulfonyl)pyridin-3-yl]benzonitrileYield 149.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

The tert-butyl (1-{4-cyano-2-ethoxy-5-methyl-3-[5-(methylsulfonyl)pyridin-3-yl]phenyl}ethyl)carbamate (0.030 gm, 0.065 mmol) was dissolved in 4.0 M HCl in dioxane (2 mL) and was stirred for 1 hour. The reaction was concentrated in vacuo to give 4-(1-aminoethyl)-3-ethoxy-6-methyl-2-[5-(methylsulfonyl)pyridin-3-yl]benzonitrile as a semi-solid (0.035 g, 100%). LCMS calculated for C18H22N3O3S (M+H)+: m/z=360.1. found: 360.2.

Workup

  1. concentrationThe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-7f4481437a28451d9a6cbfb4400bfee1
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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