Pyridine → HCID 69057960, compound

HRID 492253Notes

Reaction equation

HRID 492253 reaction equation
[Cl-].ClC1N(C)[CH2:6][CH2:5][NH+]1C.[NH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]#[N:18])=[N:15][CH:16]=1.[OH:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][C:24]([C:29]([OH:31])=O)=[CH:23]2.C(=O)([O-])O.[Na+].N1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C(Cl)(Cl)Cl>[CH2:38]([O:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][C:24]([C:29]([NH:10][C:11]1[CH:16]=[N:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=1)=[O:31])=[CH:23]2)[C:39]1[CH:6]=[CH:5][CH:42]=[CH:41][CH:40]=1

Participants

7

Reactant 5

HCID 1049PyridineHCID 889585-Hydroxyindole-2-carboxylic acidHCID 516892Sodium BicarbonateHCID 38713955-Aminopyridine-2-carbonitrileHCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chloride

Product 1

HCID 69057960HCID 69057960, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

At 0° C., 2-chloro-1,3-dimethyl-imidazolinium chloride (1.0 g) was added to a chloroform (6.0 mL)/pyridine (6.0 mL) mixed solution of 5-amino-2-cyanopyridine (500 mg) and 5-hydroxyindole-2-carboxylic acid (1.1 g), and stirred for 3 hours, and further stirred overnight at room temperature. Aqueous sodium hydrogencarbonate solution was added to the reaction liquid to stop the reaction, and this was extracted with chloroform. The organic layer was washed with water and saturated saline water, and then dried with anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting crystal was washed with chloroform to obtain the entitled compound (1.4 g) as a pale red solid.

Workup

  1. customfurther stirred overnight
  2. customat room temperature
  3. customthe reaction
  4. extractionthis was extracted with chloroform
  5. washThe organic layer was washed with water and saturated saline water
  6. dry with materialdried with anhydrous sodium sulfate
  7. concentrationThe organic layer was concentrated under reduced pressure
  8. washthe resulting crystal was washed with chloroform

Sources & evidence

ORD record
ord-dd1afc25339d4bd0a78c093b7d8b3fc2
Source dataset
uspto-grants-2009_05
Patent number
US07531668B2

Reaction notes

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