Nicotinic Acid → HCID 19600415, compound

HRID 609769Notes

Reaction equation

HRID 609769 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[CH2:10]([N:17]1[C:21]2[CH:22]=[C:23]([Cl:26])[CH:24]=[CH:25][C:20]=2[N:19]=[C:18]1[C:27]([NH:29][C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[N:35]([CH2:39][CH2:40][CH2:41][NH2:42])[CH:34]=[CH:33]2)=[O:28])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C.C(OP(C#N)(=O)OCC)C>CN(C)C=O.O>[CH2:10]([N:17]1[C:21]2[CH:22]=[C:23]([Cl:26])[CH:24]=[CH:25][C:20]=2[N:19]=[C:18]1[C:27]([NH:29][C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[N:35]([CH2:39][CH2:40][CH2:41][NH:42][C:1]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)=[O:9])[CH:34]=[CH:33]2)=[O:28])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 938Nicotinic AcidHCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 19600385HCID 19600385, compound

Product 1

HCID 19600415HCID 19600415, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To 0.29 g of nicotinic acid was added 50 ml of dimethylformamide, further 1.2 g of 1-benzyl-6-chloro-2-[1-(3-aminopropyl)indol-5-ylaminocarbonyl]-benzimidazole and 0.7 ml of triethylamine were added, the mixture was stirred under cooling at 0° C. Next, 0.49 g of diethylcyanophosphonate was dissolved in 20 ml of dimethylformamide and added thereto and the reaction mixture was stirred at room temperature for 1 day. After the reaction was finished, water was added then the whole mixture was extracted with ethyl acetate, the extract thus obtained was washed with water and an aqueous solution saturated with sodium chloride. The washed extract was dried with anhydrous magnesium sulfate, then the solvent was removed by distillation under reduced pressure. The resulting residue was subjected to a silica gel column chromatography (eluent: 2% methanol/dichloromethane), recrystallized from chloroform, there was obtained 1 g of 1-benzyl-6-chloro-2-{1-[3-(pyridin-3-ylcarbonylamino)propyl]indol-5-ylaminocarbonyl}benzimidazole as in the form of yellow needle crystals.

Workup

  1. additionwere added
  2. additionadded
  3. stirringthe reaction mixture was stirred at room temperature for 1 day
  4. extractionthe whole mixture was extracted with ethyl acetate
  5. extractionthe extract thus
  6. customobtained
  7. washwas washed with water
  8. extractionThe washed extract
  9. dry with materialwas dried with anhydrous magnesium sulfate
  10. customthe solvent was removed by distillation under reduced pressure
  11. customrecrystallized from chloroform

Sources & evidence

ORD record
ord-9e19dc40df064cbabf38fdc428f15528
Source dataset
uspto-grants-1999_12
Patent number
US05998437

Reaction notes

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