Hydrochloric Acid → HCID 178478832, compound

HRID 1821848Notes

Reaction equation

HRID 1821848 reaction equation
[C:1]1([C:7]([C:9]2[NH:17][C:12]3=[CH:13][N:14]=[CH:15][CH:16]=[C:11]3[CH:10]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18]([NH:21][NH2:22])([NH2:20])=[NH:19].[ClH:23].Cl.CCOCC>C(O)C.CO>[ClH:23].[ClH:23].[C:1]1([C:7](=[N:22][NH:21][C:18]([NH2:20])=[NH:19])[C:9]2[NH:17][C:12]3=[CH:13][N:14]=[CH:15][CH:16]=[C:11]3[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 3283Diethyl EtherHCID 57893467HCID 57893467, compoundHCID 178418668HCID 178418668, compound

Product 1

HCID 178478832HCID 178478832, compoundYield 154.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent2×

Procedure

To a solution of phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone (Example 35) (0.15 g, 0.67 mmol) in ethanol (6.7 mL) were added aminoguanidine hydrochloride (0.09 g, 0.81 mmol) and 6 N HCl (0.56 mL). The reaction mixture was heated to reflux under N2. After 3 h, heating was terminated and the reaction mixture was slowly cooled to room temperature overnight. The reaction mixture was concentrated to dryness. The residue was dissolved in water and washed with diethyl ether. The aqueous layer was made basic with 15% NaOH solution and extracted with ethyl acetate (2×). The organic extracts were combined and washed with water and saturated NaCl, and dried over Na2SO4. Filtration and concentration provided the crude residue, which was dissolved in methanol. To the methanol solution was added 2 N HCl in Et2O (0.67 mL, 1.34 mmol). The mixture was concentrated to dryness and the resulting solid was crystallized from EtOH/Et2O (9:1) to provide [[phenyl (1H-pyrrolo[2,3-c]pyridin-2-yl)methylene]amino]guanidine dihydrochloride (0.22 g, 93%) as an off-white solid: mp 306-310° C.; 1H NMR (300 MHz, CD3OD) δ6.71 (1H, s), 7.57-7.74 (5H, m), 8.07 (1H, d, J=6.5 Hz), 8.24 (1H, d, J=6.4 Hz), 9.10 (1H, s); ESI MS m/z 279 [C15H14N6+H]+; HPLC (Method A) >99% (AUC) tR=12.9 min.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux under N2
  3. temperatureheating
  4. customwas terminated
  5. concentrationThe reaction mixture was concentrated to dryness
  6. dissolutionThe residue was dissolved in water
  7. washwashed with diethyl ether
  8. extractionextracted with ethyl acetate (2×)
  9. washwashed with water and saturated NaCl
  10. dry with materialdried over Na2SO4
  11. filtrationFiltration and concentration
  12. customprovided the crude residue, which
  13. concentrationThe mixture was concentrated to dryness
  14. customthe resulting solid was crystallized from EtOH/Et2O (9:1)

Sources & evidence

ORD record
ord-63a8477db05f475494a3b91d7cce41e8
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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