O-Phenylenediamine → HCID 58668628, compound

HRID 2054461Notes

Reaction equation

HRID 2054461 reaction equation
[CH:1]([C:3]1[C:4]([NH:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])=[N:5][CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:8]=1)=O.[C:22]1([NH2:29])[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH2:28].OS([O-])=O.[Na+]>CC(N(C)C)=O>[NH:28]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N:29]=[C:1]1[C:3]1[C:4]([NH:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])=[N:5][CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:8]=1

Participants

5

Reactant 3

HCID 7243O-PhenylenediamineHCID 23665763Sodium BisulfiteHCID 58668622HCID 58668622, compound

Product 1

HCID 58668628HCID 58668628, compoundYield 27.8%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
250 °C

Procedure

N-(3-formyl-5-phenylpyridin-2-yl)-2,2-dimethylpropanamide (0.1 g, 0.35 mmol), o-phenylenediamine (0.038 g, 0.35 mmol), and NaHSO3 (0.039, 0.53 mmol) were combined in 3 mL of dimethylacetamide and heated to 250° C. in the SmithSynthesizer™ microwave instrument for 10 minutes. Upon cooling, the solvent was removed and the residue was chromatographed on silica gel eluting with hexanes/ethyl acetate (0 to 100% EtOAc over 20 minutes) to afford N-[3-(1H-benzimidazol-2-yl)-5-phenylpyridin-2-yl]-2,2-dimethylpropanamide (0.036 g). 1H NMR (400 MHz, DMSO-D6) δ ppm 1.37 (s, 9H) 7.32 (m, 2H) 7.45 (m, 1H) 7.56 (t, J=7.60 Hz, 2H) 7.65 (d, J=7.87 Hz, 1H) 7.72 (d, J=7.87 Hz, 1H) 7.86 (dd, J=8.33, 1.19 Hz, 2H) 8.81 (d, J=10.07 Hz, 2H) 12.87 (s, 1H) 13.38 (s, 1H) MS m/z 371 (M+1)+.

Workup

  1. temperatureUpon cooling
  2. customthe solvent was removed
  3. customthe residue was chromatographed on silica gel eluting with hexanes/ethyl acetate (0 to 100% EtOAc over 20 minutes)

Sources & evidence

ORD record
ord-f0a46515c1d343deb76c0b028f33d6b6
Source dataset
uspto-grants-2008_02
Patent number
US07329678B2

Reaction notes

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