Tetrahydrofuran → tert-Butyl [5-(2-{5-(aminomethyl)-2-[(tert-butoxycarbonyl)amino]phenyl}ethyl)pyridin-3-yl]carbamate

HRID 1614982Notes

Reaction equation

HRID 1614982 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][C:10]=1[CH2:17][CH2:18][C:19]1[CH:20]=[C:21]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH:22]=[N:23][CH:24]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O1CCCC1>[Ni].CO>[NH2:16][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[C:10]([CH2:17][CH2:18][C:19]2[CH:20]=[C:21]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:29])[CH3:30])[CH:22]=[N:23][CH:24]=2)[CH:11]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 58467830tert-Butyl [5-(2-{2-[(tert-butoxycarbonyl)amino]-5-cyanophenyl}ethyl)pyridin-3-yl]carbamate

Product 1

HCID 58467865tert-Butyl [5-(2-{5-(aminomethyl)-2-[(tert-butoxycarbonyl)amino]phenyl}ethyl)pyridin-3-yl]carbamateYield 99%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Into a pressure bottle were added tert-butyl [5-(2-{2-[(tert-butoxycarbonyl)amino]-5-cyanophenyl}ethyl)pyridin-3-yl]carbamate (0.80 g, 1.8 mmol), tetrahydrofuran (3 mL), methanol (10 mL), and Raney nickel (0.30 g, 5 mmol). The reaction mixture was hydrogenated at 45 psi for 2 hours. After filtration to remove the catalyst, the mixture was concentrated under vacuum to give the desired product as an off-white powder (0.30 g, 99%). LCMS for C24H35N4O4 (M+H)+: m/z=443.2.

Workup

  1. filtrationAfter filtration
  2. customto remove the catalyst
  3. concentrationthe mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-758989b6efd04032bebce6e97aa6c733
Source dataset
uspto-grants-2014_07
Patent number
US08765727B2

Reaction notes

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