Hydrochloric Acid → HCID 12993667, compound

HRID 859856Notes

Reaction equation

HRID 859856 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=O)#[N:2].[NH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([Cl:15])=[N:13][CH:14]=1.Cl.CN(C)CCCN=C=NCC.Cl>C(OCC)(=O)C.C(Cl)(Cl)Cl.ClCCl>[Cl:15][C:12]1[N:13]=[CH:14][C:9]([CH2:8][NH:7][C:4](=[O:6])[CH2:3][C:1]#[N:2])=[CH:10][CH:11]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 9740Cyanoacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 70209275-(Aminomethyl)-2-chloropyridine

Product 1

HCID 12993667HCID 12993667, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Cyanoacetic acid (2.6 g, 0.030 mmol), 5-aminomethyl-2-chloropyridine (4.3 g, 0.030 mmol) and 1-[3-(dimethylamino) propyl]-3-ethylcarbodiimide hydrochloric acid salt (5.8 g, 0.030 mol) were added to dichloromethane (50 ml), and stirred overnight. Chloroform and 1N hydrochloric acid were added thereto, and crystals were separated out. The crystals were filtered off, dissolved in ethyl acetate, and water was added thereto and subjected to extraction. The organic phase was washed with a saturated sodium bicarbonate and a saturated brine, and then dried anhydrous sodium sulfate. The residue obtained by filtrating and concentrating was washed with hexane and a little amount of ethyl acetate to obtain N-(6-chloro-3-pyridylmethyl)-2-cyanoacetic acid amide (6.1 g, 0.029 mmol, 97%).

Workup

  1. customcrystals were separated out
  2. filtrationThe crystals were filtered off
  3. dissolutiondissolved in ethyl acetate
  4. additionwater was added
  5. extractionsubjected to extraction
  6. washThe organic phase was washed with a saturated sodium bicarbonate
  7. customThe residue obtained
  8. filtrationby filtrating
  9. concentrationconcentrating
  10. washwas washed with hexane

Sources & evidence

ORD record
ord-d709858fd6824a639443ed95c0d679eb
Source dataset
uspto-grants-2006_12
Patent number
US07153815B2

Reaction notes

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