Picolinimidamide → HCID 178517492, compound

HRID 1878608Notes

Reaction equation

HRID 1878608 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([NH2:9])=[NH:8].C[O-:11].[Na+].Cl[C:14]1C=C(C2C=CC=C(C)N=2)N=[C:16]2[NH:27][CH:28]=[CH:29][C:15]=12>CCO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:9]=[C:14]([OH:11])[C:15]2[CH:29]=[CH:28][NH:27][C:16]=2[N:8]=1

Participants

5

Reactant 3

HCID 556504PicolinimidamideHCID 10942334Sodium MethoxideHCID 687902414-chloro-6-(6-methyl-pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 178517492HCID 178517492, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Pyridine-2-carboxamidine (1 eq, 24.8 mmol, 5.69 g) is dissolved in EtOH (60 ml). After addition of NaOMe (30% in MeOH, 1.5 eq, 37 mmol, 6.9 ml) the mixture is stirred for 3 h at r.t. and then filtered. The filtrate is added to 2-cyano-4,4-diethoxy-butyric acid ethyl ester (see Journal of Heterocyclic Chemistry (2006), 43 (6), 1523-1531) (1 eq, 24.8 mmol, 3.01 g) and the resulting mixture is heated at 80° C. for 18 h. The solvents are evaporated, then water (50 ml), EtOH (50 ml) and aqueous HCl solution (2M, 50 ml) are added and the mixture is stirred at 0° C. for 2 h. The mixture is adjusted to pH 8 using aqueous NaOH solution (8 M) and the resulting precipitate is filtered and washed with cold water. The crystals are dried in vacuo giving the title compound; [M+H]+=213.

Workup

  1. filtrationfiltered
  2. temperaturethe resulting mixture is heated at 80° C. for 18 h
  3. customThe solvents are evaporated
  4. additionwater (50 ml), EtOH (50 ml) and aqueous HCl solution (2M, 50 ml) are added
  5. stirringthe mixture is stirred at 0° C. for 2 h
  6. filtrationthe resulting precipitate is filtered
  7. washwashed with cold water
  8. customThe crystals are dried in vacuo

Sources & evidence

ORD record
ord-584d8de6562e45398ea021e1f36f6c35
Source dataset
uspto-grants-2012_11
Patent number
US08314112B2

Reaction notes

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