HCID 10923381, compound → HCID 10899400, compound

HRID 1678243Notes

Reaction equation

HRID 1678243 reaction equation
CN(C)/[CH:3]=[CH:4]/[C:5]1[C:10]([N+:11]([O-])=O)=[CH:9][N:8]=[C:7]([N:14]=[CH:15][N:16]([CH3:18])[CH3:17])[CH:6]=1>C(O)C.[Pd]>[CH3:17][N:16]([CH3:18])[CH:15]=[N:14][C:7]1[CH:6]=[C:5]2[CH:4]=[CH:3][NH:11][C:10]2=[CH:9][N:8]=1

Participants

4

Reactant 1

HCID 10923381HCID 10923381, compound

Product 1

HCID 10899400HCID 10899400, compoundYield 105%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of N′-[4-((E)-2-dimethylamino-vinyl)-5-nitro-pyridin-2-yl]-N,N-dimethyl-formamidine (Preparation #10a, 8.36 g, 31.4 mmol) and 10% Pd on carbon (800 mg) in ethanol (120 mL) was shaken in a hydrogenation vessel under an atmosphere of 10-55 psi H2 for about 24 hours. The reaction was filtered through Celite® and concentrated to yield N,N-dimethyl-N′-(1H-pyrrolo[2,3-c]pyridin-5-yl)-formamidine (6.19 g, 105%) as a dark solid. RP HPLC (Table 1, Method e) Rt=0.84, m/z: (MH)+ 189. The crude product was used in the next step without further purification.

Workup

  1. filtrationThe reaction was filtered through Celite®
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-3d1b87fcb5af404b8b0808e2ed26d311
Source dataset
uspto-grants-2011_08
Patent number
US08008481B2

Reaction notes

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