tert-Butyl [5-({2-[(tert-butoxycarbonyl)amino]-5-cyanophenyl}ethynyl)pyridin-3-yl]carbamate → tert-Butyl [5-(2-{2-[(tert-butoxycarbonyl)amino]-5-cyanophenyl}ethyl)pyridin-3-yl]carbamate

HRID 1614981Notes

Reaction equation

HRID 1614981 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[C:17]#[C: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]>[Pd].CO>[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]

Participants

4

Reactant 1

HCID 58467911tert-Butyl [5-({2-[(tert-butoxycarbonyl)amino]-5-cyanophenyl}ethynyl)pyridin-3-yl]carbamate

Product 1

HCID 58467830tert-Butyl [5-(2-{2-[(tert-butoxycarbonyl)amino]-5-cyanophenyl}ethyl)pyridin-3-yl]carbamateYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Into a reaction flask were added tert-butyl [5-({2-[(tert-butoxycarbonyl)amino]-5-cyanophenyl}ethynyl)pyridin-3-yl]carbamate (0.94 g, 2.2 mmol), methanol (50 mL), and 10% palladium on carbon (0.40 g, 0.38 mmol). The mixture was hydrogenated at 60 psi for 6 hours. After filtration to remove the catalyst, the mixture was concentrated under vacuum to give the desired product as an off-white powder (0.94 g, 99%). LCMS for C24H31N4O4 (M+H)+: m/z=439.2.

Workup

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

Sources & evidence

ORD record
ord-32c9de6cac57420aad2ecb2730bd2e69
Source dataset
uspto-grants-2014_07
Patent number
US08765727B2

Reaction notes

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