Hydrochloric Acid → HCID 178478833, compound

HRID 1821862Notes

Reaction equation

HRID 1821862 reaction equation
[CH2:1]([N:8]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:9]1[CH:10]=[C:11]2[CH:17]=[C:16]([C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=O)[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:33]([NH:36][NH2:37])([NH2:35])=[NH:34].[ClH:38].Cl>C(O)C>[ClH:38].[ClH:38].[CH2:1]([N:8]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:9]1[CH:10]=[C:11]2[CH:17]=[C:16]([C:18](=[N:37][NH:36][C:33]([NH2:35])=[NH:34])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[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 57893557HCID 57893557, compoundHCID 178418668HCID 178418668, compound2×

Product 1

HCID 178478833HCID 178478833, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of [5-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridin-2-yl](phenyl)methanone (Example 55) (129 mg, 0.31 mmol), aminoguanidine hydrochloride (36 mg, 0.32 mmol) and 6 N HCl (0.26 mL) in ethanol (10 mL) was heated to reflux under a nitrogen atmosphere for 2.5 h. TLC analysis showed the remaining ketone, therefore additional aminoguanidine hydrochloride (10 mg, 0.09 mmol) was added. The reaction mixture was refluxed until TLC analysis showed the reaction was completed (2 h). After concentration to dryness, the crude material was triturated with EtOAc. The solid was collected by filtration and dried to provide [[[5-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridin-2-yl](phenyl)methylene]amino]guanidine dihydrochloride (60.6 mg, 36%) as a yellow solid: ESI MS m/z 474 [C29H27N7+H]+; HPLC (Method A) 89.3% (AUC), tR=17.5 min.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under a nitrogen atmosphere for 2.5 h
  3. temperatureThe reaction mixture was refluxed until TLC analysis
  4. custom(2 h)
  5. concentrationAfter concentration to dryness
  6. customthe crude material was triturated with EtOAc
  7. filtrationThe solid was collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-ebfd0848dbf84a6a8e0d9db08374abc1
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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