Dimethylformamide → HCID 66692733, compound

HRID 1048981Notes

Reaction equation

HRID 1048981 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])[CH:5]=[CH:6][C:7]=1[NH:8][CH3:9].CN(C=O)C.OOS([O-])=O.[K+].[CH:26](=O)[C:27]1[CH:32]=[CH:31][CH:30]=[N:29][CH:28]=1>O>[CH3:9][N:8]1[C:7]2[CH:6]=[CH:5][C:4]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[CH:3][C:2]=2[N:1]=[C:26]1[C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 103713-PyridinecarboxaldehydeHCID 23707502Potassium hydroxy sulfiteHCID 57291174HCID 57291174, compound

Product 1

HCID 66692733HCID 66692733, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of N-(3-amino-4-(methyl amino) phenyl) methane sulfonamide (0.3 g, 0.0013 mol) in the mixture of DMF (10 ml) and water (2 ml) was added OXONE® (1.02 g, 0.0016 mol) and followed by nicotinaldehyde (0.16 g, 0.0015 mol) was added portion wise with constant stirring. The reaction mixture was allowed to stir at room temperature for 3 h. The reaction mixture was concentrated on a high vacuo pump and diluted with cold water (10 ml) and extracted with ethyl acetate (3×15 ml). The combined organic layers were washed with brine dried over Na2SO4 and concentrated in vacuo and purified by column chromatography on silica gel to afford the desired product N-[1-methyl-2-(pyridin-3-yl)-1H-benzimidazol-5-yl]methanesulfonamide (363) as a brown solid. 1H NMR (400 MHz, DMSO-d6), δ: 9.53 (bs, 1H), 9.04 (s, 1H), 8.75-8.77 (d, J=4.0 Hz, 1H), 8.28-8.26 (d, J=8.0 Hz, 1H), 7.68-7.57 (m, 3H), 7.24-7.21 (d, J=8.4 Hz, 1H), 3.89 (s, 3H), 2.91 (s, 3H). LCMS (ES) m/e MS (M+1=244), Purity 95.64%.

Workup

  1. additionwas added portion wise with constant stirring
  2. concentrationThe reaction mixture was concentrated on a high vacuo pump
  3. additiondiluted with cold water (10 ml)
  4. extractionextracted with ethyl acetate (3×15 ml)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-01aca3b7422f4e14b762aa4550c941a2
Source dataset
uspto-grants-2016_07
Patent number
US09382226B2

Reaction notes

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