Potassium Carbonate → 4-{4-cyano-3-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]phenoxy}pyridine-2-carbonitrile

HRID 1616219Notes

Reaction equation

HRID 1616219 reaction equation
[CH3:1][C:2]([CH3:25])([CH3:24])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([C:13]3[CH:20]=[C:19]([OH:21])[CH:18]=[CH:17][C:14]=3[C:15]#[N:16])=[CH:10][CH:11]=2)[N:6]([CH3:22])[C:5]1=[O:23].C(=O)([O-])[O-].[K+].[K+].Cl[C:33]1[CH:38]=[CH:37][N:36]=[C:35]([C:39]#[N:40])[CH:34]=1>CS(C)=O>[C:15]([C:14]1[CH:17]=[CH:18][C:19]([O:21][C:33]2[CH:38]=[CH:37][N:36]=[C:35]([C:39]#[N:40])[CH:34]=2)=[CH:20][C:13]=1[C:9]1[N:8]=[C:7]2[N:6]([CH3:22])[C:5](=[O:23])[N:4]([CH2:3][C:2]([CH3:25])([CH3:24])[CH3:1])[C:12]2=[CH:11][CH:10]=1)#[N:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 6933424-Chloro-2-pyridinecarbonitrileHCID 866918272-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]-4-hydroxybenzonitrile

Product 1

HCID 866918294-{4-cyano-3-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]phenoxy}pyridine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 2-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]-4-hydroxybenzonitrile (16-2, 100 mg, 0.30 mmol) in DMSO (4 ml) was charged with Potassium carbonate (82 mg, 0.59 mmol, 2.0 equiv) and 4-Chloro-pyridine-2-carbonitrile (82 mg, 0.59 mmol, 2.0 equiv). The reaction was irradiated at 160° C. for 20 min. The dark mixture was purified via reverse-phase HPLC (Acetonitrile/Water gradient with 0.1% TFA present) to afford the title compound, 4-{4-cyano-3-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]phenoxy}pyridine-2-carbonitrile (3), as a pure yellow-tan solid-oil. 1H NMR (500 MHz, CDCl3) δ 8.64 (d, 1H, J=5.6 Hz), 7.91 (d, 1H, J=8.3 Hz), 7.62 (bs, 1H), 7.54 (d, 1H, J=8.1 Hz), 7.36-7.33 (m, 2H), 7.21-7.15 (m, 2H), 3.71 (s, 2H), 3.58 (s, 3H), 1.06 (s, 9H). LRMS m/z: Calc'd for C25H22N6O2 (M+H) 439.0. found 439.1.

Workup

  1. customThe reaction was irradiated at 160° C. for 20 min
  2. customThe dark mixture was purified via reverse-phase HPLC (Acetonitrile/Water gradient with 0.1% TFA present)

Sources & evidence

ORD record
ord-bb495283cd224aea8983aaedac7fc37c
Source dataset
uspto-grants-2014_07
Patent number
US08765784B2

Reaction notes

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