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

HRID 541754Notes

Reaction equation

HRID 541754 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[C:6]([C:8]#[C:9][C:10]2[CH:11]=[C:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=[N:14][CH:15]=2)[CH:7]=1>CO.[Pd]>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[C:6]([CH2:8][CH2:9][C:10]2[CH:11]=[C:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=[N:14][CH:15]=2)[CH:7]=1

Participants

4

Reactant 1

HCID 57961651tert-Butyl [5-({5-amino-2-[(tert-butoxycarbonyl)amino]phenyl}ethynyl)pyridin-3-yl]carbamate

Product 1

HCID 57961667tert-Butyl [5-(2-{5-amino-2-[(tert-butoxycarbonyl)amino]phenyl}ethyl)pyridin-3-yl]carbamateYield 92.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl [5-({5-amino-2-[(tert-butoxycarbonyl)amino]phenyl}ethynyl)pyridin-3-yl]carbamate (1.50 g, 3.53 mmol) in methanol (30 mL) was added 10% palladium on carbon (150 mg, 0.141 mmol), and the mixture was hydrogenated under 25 psi of H2 for 2 hours with shaking. The solution was filtered through a pad of celite, and filtrate was concentrated. The residue was purified by flash column chromatography to give the desired product (1.40 g, 92%). LCMS calculated for C23H33N4O4(M+H)+: m/z=429.1.

Workup

  1. filtrationThe solution was filtered through a pad of celite, and filtrate
  2. concentrationwas concentrated
  3. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-73204db8892d494e816b3160802c286e
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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