HCID 178432740, compound → HCID 178432741, compound

HRID 2388017Notes

Reaction equation

HRID 2388017 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[C:14]([NH:19]/[C:20](/[NH:32]C(=O)OCC2C=CC=CC=2)=[N:21]/C(=O)OCC2C=CC=CC=2)[C:15]([CH3:18])=[N:16][CH:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[OH-].[OH-].[Pd+2]>[NH2:32][C:20]([NH:19][C:14]1[CH:13]=[C:12]([CH2:11][CH2:10][CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH:17]=[N:16][C:15]=1[CH3:18])=[NH:21]

Participants

4

Reactant 1

HCID 178432740HCID 178432740, compound

Product 1

HCID 178432741HCID 178432741, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of dibenzyl {(Z)-[(5-{3-[(tert-butoxycarbonyl)amino]propyl}-2-methylpyridin-3-yl)amino]methylylidene}biscarbamate (3.34 g, 5.80 mmol) in MeOH (100 mL) was added palladium hydroxide on carbon (0.41 g). The reaction vessel was flushed with hydrogen gas and then allowed to stir at rt under an atmosphere of hydrogen gas overnight. The reaction mixture was filtered over a pad of Celite® and the filtrate was concentrated to give tert-butyl [3-(5-{[amino(imino)methyl]amino}-6-methylpyridin-3-yl)propyl]carbamate (1.77 g, 5.76 mmol, 99%) as a white solid. LCMS (FA): Rt=0.76 min, m/z=308.0 (M+H).

Workup

  1. customThe reaction vessel was flushed with hydrogen gas
  2. filtrationThe reaction mixture was filtered over a pad of Celite®
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-907c16d4f4f540f58a1b5b40b8733769
Source dataset
uspto-grants-2012_09
Patent number
US08268992B2

Reaction notes

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