HCID 178432740, compound → HCID 178432741, compound

HRID 1892216Notes

Reaction equation

HRID 1892216 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]>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[N:16][C:15]([CH3:18])=[C:14]([NH:19][C:20]([NH2:32])=[NH:21])[CH:13]=1)([CH3:3])([CH3:4])[CH3:2]

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-7b8665637bad4d1db243c6f42f7e1492
Source dataset
uspto-grants-2013_08
Patent number
US08507667B2

Reaction notes

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