Hydrochloric Acid → HCID 178478831, compound

HRID 1821871Notes

Reaction equation

HRID 1821871 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[C:9]([C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=O)[NH:8][C:5]2=[CH:6][N:7]=1.[C:19]([NH:22][NH2:23])([NH2:21])=[NH:20].[ClH:24].Cl>C(O)C>[ClH:1].[ClH:24].[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[C:9]([C:11](=[N:23][NH:22][C:19]([NH2:21])=[NH:20])[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:8][C:5]2=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 57893472HCID 57893472, compoundHCID 178418668HCID 178418668, compound

Product 1

HCID 178478831HCID 178478831, compoundYield 161.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (5-chloro-1H-pyrrolo[2,3-c]pyridin-2-yl)(phenyl)methanone (Example 73) (65 mg, 0.25 mmol) in ethanol (5 mL) was added aminoguanidine hydrochloride (55 mg, 0.85 mmol) and 6 N HCl (0.2 mL). The reaction mixture was heated to reflux under N2. After 2 h, heating was terminated and the reaction mixture was cooled to room temperature forming a white precipitate. The precipitate was collected by filtration and dried under vacuum to provide [[(5-chloro-1H-pyrrolo[2,3-c]pyridin-2-yl)(phenyl)methylene]amino]guanidine dihydrochloride (78 mg, 100%) as a white solid: mp 274-278° C.; 1H NMR (300 MHz, CD3OD) δ 6.62 (1H, s), 7.49-7.58 (2H, m), 7.68-7.79 (4H, m), 8.04 (1H, s), 8.98 (1H, s); ESI MS m/z 313 [C15H13ClN6+H]+; HPLC (Method A) >99% (AUC) tR=16.5 min.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux under N2
  3. temperatureheating
  4. customwas terminated
  5. customforming a white precipitate
  6. filtrationThe precipitate was collected by filtration
  7. customdried under vacuum

Sources & evidence

ORD record
ord-ad49ca0733ad422ca760696aa78d6abc
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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