3-Pyridinecarboxaldehyde → HCID 56645777, compound

HRID 1048967Notes

Reaction equation

HRID 1048967 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[NH:10][CH:11]1[CH2:13][CH2:12]1.[CH:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[N:17][CH:16]=1.OOS([O-])=O.[K+].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH:11]1([N:10]2[C:3]3[CH:4]=[C:5]([C:6]#[N:7])[CH:8]=[CH:9][C:2]=3[N:1]=[C:14]2[C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH2:12][CH2:13]1

Participants

7

Reactant 4

HCID 103713-PyridinecarboxaldehydeHCID 11430Potassium CarbonateHCID 23707502Potassium hydroxy sulfiteHCID 666847494-Amino-3-(cyclopropylamino)benzonitrile

Product 1

HCID 56645777HCID 56645777, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-amino-3-(cyclopropylamino) benzonitrile, (0.2 g, 0.0011 mol) and nicotinaldehyde (0.14 g, 0.0012 mol) in DMF (5 ml) and H2O (2 ml) was added OXONE® monopersulphate (0.84 g, 0.0013 mol). Reaction mass was stirred at room temperature for 3 h. The reaction mixture was basified with 10% K2CO3 solution to pH˜8-10 and extracted with EtOAc (3×20 ml). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated under vacuum to afford the crude compound, which was purified by column chromatography to obtain title compound 1-cyclopropyl-2-(pyridine-3-yl)-1H-benzo[d]imidazole-6-carbonitrile. 1H NMR (400 MHz, DMSO-d6), δ: 9.21 (s, 1H), 8.77-8.76 (d, J=4.4 Hz, 1H), 8.45-8.43 (d, J=8 Hz, 1H), 8.25 (s, 1H), 7.89-7.87 (d, J=8 Hz, 1H), 7.68-7.61 (m, 2H), 3.91-3.87 (m, 1H), 1.17-1.12 (m, 2H), 0.71-0.70 (m, 2H). MS (M+1): 261.12; purity 97.77%.

Workup

  1. customReaction mass
  2. extractionextracted with EtOAc (3×20 ml)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. customto afford the crude compound, which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-6c647904689b49cd95a2c5f32918d923
Source dataset
uspto-grants-2016_07
Patent number
US09382226B2

Reaction notes

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