Ethyl 4-[(5,6-dimethyl-8-nitrotetraazolo[1,5-a]pyridin-7-yl)amino]butanoate → Ethyl 4-[(8-amino-5,6-dimethyltetraazolo[1,5-a]pyridin-7-yl)amino]butanoate

HRID 2366702Notes

Reaction equation

HRID 2366702 reaction equation
[CH3:1][C:2]1[N:7]2[N:8]=[N:9][N:10]=[C:6]2[C:5]([N+:11]([O-])=O)=[C:4]([NH:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:3]=1[CH3:23]>[Pd].C(#N)C>[NH2:11][C:5]1[C:6]2[N:7]([N:8]=[N:9][N:10]=2)[C:2]([CH3:1])=[C:3]([CH3:23])[C:4]=1[NH:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

4

Reactant 1

HCID 57447078Ethyl 4-[(5,6-dimethyl-8-nitrotetraazolo[1,5-a]pyridin-7-yl)amino]butanoate

Product 1

HCID 57447079Ethyl 4-[(8-amino-5,6-dimethyltetraazolo[1,5-a]pyridin-7-yl)amino]butanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of ethyl 4-[(5,6-dimethyl-8-nitrotetraazolo[1,5-a]pyridin-7-yl)amino]butanoate (10.0 g, 31.0 mmol), 10% palladium on carbon (1.0 g), and acetonitrile (310 mL) was added to a pressure vessel, and the reaction was placed under hydrogen pressure (30 psi, 2.1×105 Pa) overnight. The reaction mixture was filtered through a layer of CELITE filter agent, and the filter cake was washed with methanol (50 mL). The filtrate was concentrated under reduced pressure to provide ethyl 4-[(8-amino-5,6-dimethyltetraazolo[1,5-a]pyridin-7-yl)amino]butanoate as a solid. This reaction was repeated a second time.

Workup

  1. additionwas added to a pressure vessel
  2. custompressure (30 psi, 2.1×105 Pa) overnight
  3. filtrationThe reaction mixture was filtered through a layer of CELITE filter agent
  4. washthe filter cake was washed with methanol (50 mL)
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-13a5a0230a4943f99af1a3a755b8080c
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

Loading…