Potassium Carbonate → HCID 66750162, compound

HRID 882198Notes

Reaction equation

HRID 882198 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:18]=[CH:17][C:11]3[NH:12][C:13](=O)[N:14]([CH3:15])[C:10]=3[C:9]=2CC(C)(C)C)[CH:5]=[CH:4][CH:3]=1.[C:24](=[O:27])([O-])[O-].[K+].[K+].[C:30]([C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=1)#[N:31]>CS(C)=O>[CH3:6][C:8]([CH3:18])([CH3:9])[CH2:13][N:12]1[C:11]2[CH:17]=[CH:18][C:8]([C:6]3[N:7]=[C:2]([O:38][C:35]4[CH:36]=[CH:37][C:32]([C:30]#[N:31])=[CH:33][CH:34]=4)[CH:3]=[CH:4][CH:5]=3)=[CH:9][C:10]=2[N:14]([CH3:15])[C:24]1=[O:27]

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 130194-Cyanophenol2×HCID 86686104HCID 86686104, compound

Product 1

HCID 66750162HCID 66750162, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 5-(6-chloropyridin-2-yl)-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-benzimidazol-2-one (5-2, 55 mg, 0.17 mmol) in DMSO (1 ml), was charged with Potassium carbonate (34.6 mg, 0.25 mmol, 1.5 eq) and 4-Cyanophenol (39.7 mg, 0.33 nmol, 2.0 eq), then irradiated in a microwave at 160 deg C. for 20 min. A second addition of Potassium carbonate (34.6 mg, 0.25 mmol, 1.5 eq) and 4-Cyanophenol (39.7 mg, 0.33 mmol, 2.0 eq) was necessary, then the reaction was irradiated again at 160 deg C. for 20 min. The crude, dark mixture was filtered through a fritted disk, then purified via reverse-phase HPLC (Acetonitrile/Water gradient with 0.1% TFA present) to afford the title compound, 4-({6-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-5-yl]pyridin-2-yl}oxy)benzonitrile (5-3), as an orange oil. 1H NMR (500 MHz, CDCl3) δ 7.80 (t, 1H, J=Hz), 7.71 (d, 2H, J=9.0 Hz), 7.62 (d, 1H, J=7.1 Hz), 7.55 (d, 1H, J=7.3 Hz), 7.51 (s, 1H), 7.34-7.31 (m, 2H), 7.06-7.04 (d, 2H, 8.3 Hz), 6.87 (d, 1H, J=8.1 Hz), 3.68 (s, 2H), 3.44 (s, 3H), 1.04 (s, 9H). LRMS m/z: Calcd for C25H25N4O2 (M+H) 414.2, found 414.3.

Workup

  1. customirradiated in a microwave at 160 deg C
  2. customthe reaction was irradiated again at 160 deg C
  3. waitfor 20 min
  4. filtrationThe crude, dark mixture was filtered through a fritted disk
  5. custompurified via reverse-phase HPLC (Acetonitrile/Water gradient with 0.1% TFA present)

Sources & evidence

ORD record
ord-9440e93ad79c488882d87311bef05511
Source dataset
uspto-grants-2015_03
Patent number
US08993779B2

Reaction notes

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