Dimethylformamide → HCID 66692352, compound

HRID 1048978Notes

Reaction equation

HRID 1048978 reaction equation
[NH2:1][C:2]1[C:3]([NH:12][CH3:13])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([NH:7][CH3:8])=[O:6].CN(C=O)C.OOS([O-])=O.[K+].[CH:25](=O)[C:26]1[CH:31]=[CH:30][CH:29]=[N:28][CH:27]=1>O>[CH3:8][NH:7][C:5]([C:4]1[C:3]2[N:12]([CH3:13])[C:25]([C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)=[N:1][C:2]=2[CH:11]=[CH:10][CH:9]=1)=[O:6]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 103713-PyridinecarboxaldehydeHCID 23707502Potassium hydroxy sulfiteHCID 66684683HCID 66684683, compound

Product 1

HCID 66692352HCID 66692352, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 3-amino-N-methyl-2-(methyl-amino) benzamide (18; 0.2 g, 0.0011 mol) in the mixture of DMF (5 ml) and water (1 ml) was added OXONE® (0.81 g, 0.0013 mol) and followed by nicotinaldehyde (0.13 g, 0.00122 mol) was added portion wise under cooling condition 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 purified by column chromatography on silica gel to afford the desired product N,1-dimethyl-2-(pyridin-3-yl)-1H-benzimidazole-7-carboxamide as brown solid. 1H NMR (400 MHz, DMSO-d6), δ: 9.0 (s, 1H), 8.76-8.75 (d, J=4.0 Hz, 1H), 8.59 (bs, 1H), 8.25-8.23 (d, J=7.6 Hz, 1H), 7.81-7.8 (d, J=7.6 Hz, 1H), 7.64-7.61 (m, 1H), 7.35-7.27 (m, 2H), 3.79 (s, 3H), 2.85-2.84 (d, J=4.4 Hz, 3H). LCMS (ES) m/e MS (M+1-267) Purity: 98.5%.

Workup

  1. additionwas added portion wise
  2. temperatureunder cooling condition with constant stirring
  3. concentrationThe reaction mixture was concentrated on a high vacuo pump
  4. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-59eb930dc3b145c88fd08b86fe968ba1
Source dataset
uspto-grants-2016_07
Patent number
US09382226B2

Reaction notes

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