Hydrochloric Acid → HCID 178465623, compound

HRID 1821861Notes

Reaction equation

HRID 1821861 reaction equation
[CH2:1]([N:8]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:9]1[CH:10]=[C:11]2[CH:17]=[C:16]([C:18](=O)[CH3:19])[NH:15][C:12]2=[CH:13][N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28]([NH:31][NH2:32])([NH2:30])=[NH:29].[ClH:33].Cl>C(O)C>[ClH:33].[ClH:33].[CH2:1]([N:8]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:9]1[CH:10]=[C:11]2[CH:17]=[C:16]([C:18](=[N:32][NH:31][C:28]([NH2:30])=[NH:29])[CH3:19])[NH:15][C:12]2=[CH:13][N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 57893525HCID 57893525, compoundHCID 178418668HCID 178418668, compound

Product 1

HCID 178465623HCID 178465623, compoundYield 125.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-[5-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridin-2-yl]ethanone (Example 56) (91 mg, 0.26 mmol), aminoguanidine hydrochloride (30 mg, 0.27 mmol) and 6 N HCl (0.22 mL) in ethanol (10 mL) was heated to reflux under a nitrogen atmosphere for 1.5 h. The reaction mixture was cooled to room temperature, and the desired product precipitated from the solution. The solid was collected by filtration and rinsed with ethanol. After drying, [[1-[5-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridin-2-yl]ethylidene]amino]guanidine dihydrochloride (82 mg, 65%) was obtained as a yellow solid: EST MS m/z 412 [C24H25N7+H]+; HPLC (Method A) 94.9% (AUC), tR=16.5 min.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under a nitrogen atmosphere for 1.5 h
  3. customthe desired product precipitated from the solution
  4. filtrationThe solid was collected by filtration
  5. washrinsed with ethanol
  6. customAfter drying

Sources & evidence

ORD record
ord-db04f2ddef1b4f1a8fff7808e9792173
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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