Sodium Nitrate → (7-Bromo-4-chloro-1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)hydroxyiminoacetonitrile

HRID 1863997Notes

Reaction equation

HRID 1863997 reaction equation
[Br:1][C:2]1[C:3]([NH:15][CH2:16][CH3:17])=[C:4]([NH:9][C:10](=O)[CH2:11][C:12]#[N:13])[C:5]([Cl:8])=[N:6][CH:7]=1.BrC1C2N(CC)C(CC#N)=NC=2C(Cl)=NC=1.[N+:34]([O-])([O-])=[O:35].[Na+]>C(O)(=O)C>[Br:1][C:2]1[C:3]2[N:15]([CH2:16][CH3:17])[C:10]([C:11](=[N:34][OH:35])[C:12]#[N:13])=[N:9][C:4]=2[C:5]([Cl:8])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 24268Sodium NitrateHCID 45480183(7-Bromo-4-chloro-1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)acetonitrileHCID 57973904N-[5-Bromo-2-chloro-4-(ethylamino)-3-pyridinyl]-2-cyanoacetamide

Product 1

HCID 136380978(7-Bromo-4-chloro-1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)hydroxyiminoacetonitrileYield 114.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of N-[5-bromo-2-chloro-4-(ethylamino)-3-pyridinyl]-2-cyanoacetamide III, (458 g, 1.45 mol) in glacial acetic acid (4.6 L) was heated to 100° C. After 3 h, LC/MS analysis indicated that the conversion to (7-bromo-4-chloro-1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)acetonitrile (IV) was completed. After allowing to cool to ambient temperature, the reaction was charged with sodium nitrate (230 g, 3.34 mol) in portions. Vigorous gas evolution and foaming was observed together with a ˜10° C. exotherm. After stirring at ambient temperature for 16 h, the solid was collected by filtration and dried to a constant weight to give 545 g of the desired product (V) as a light yellow solid. This was used in the next step without further purification. MS (ES+) m/z 328 (M+H)+.

Workup

  1. customwas observed together with a ˜10° C.
  2. filtrationthe solid was collected by filtration
  3. customdried to a constant weight

Sources & evidence

ORD record
ord-9183eef1cd2e45eb917071992ad04803
Source dataset
uspto-grants-2009_12
Patent number
US07625890B2

Reaction notes

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