HCID 178432740, compound → HCID 178432741, compound

HRID 1672226Notes

Reaction equation

HRID 1672226 reaction equation
C(OC(=O)[NH:10]/[C:11](/[NH:23][C:24]1[C:25]([CH3:41])=[N:26][CH:27]=[C:28]([CH2:30][CH2:31][CH2:32][NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH:29]=1)=[N:12]\C(=O)OCC1C=CC=CC=1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[C:37]([O:36][C:34](=[O:35])[NH:33][CH2:32][CH2:31][CH2:30][C:28]1[CH:27]=[N:26][C:25]([CH3:41])=[C:24]([NH:23][C:11]([NH2:12])=[NH:10])[CH:29]=1)([CH3:39])([CH3:40])[CH3:38]

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-6f3b58d6f8474ceba5f74dc416dbefc7
Source dataset
uspto-grants-2011_08
Patent number
US07998952B2

Reaction notes

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