1-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethanone → HCID 178465622, compound

HRID 1821868Notes

Reaction equation

HRID 1821868 reaction equation
[NH:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[C:10](=O)[CH3:11].[C:13]([NH:16][NH2:17])([NH2:15])=[NH:14].[ClH:18]>C(O)C.Cl>[ClH:18].[ClH:18].[NH:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[C:10](=[N:17][NH:16][C:13]([NH2:15])=[NH:14])[CH3:11]

Participants

5

Reactant 2

HCID 552679001-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethanoneHCID 178418668HCID 178418668, compound

Product 1

HCID 178465622HCID 178465622, compoundYield 161.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of 1-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethanone (Example 70) (90 mg, 0.56 mmol) and aminoguanidine hydrochloride (65 mg, 0.59 mmol) in ethanol (5.6 mL) and 6 N HCl (0.47 mL) was heated under reflux for 1.5 h. The reaction mixture was cooled to room temperature and the precipitate was filtered, rinsed with ethanol and diethyl ether, and dried under vacuum at 45° C. to provide [[1-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethylidene]amino]guanidine dihydrochloride (138 mg, 86%) as a white solid: mp 314-318° C. dec.; 1H NMR (300 MHz, CD3OD) δ2.50 (3H, s), 7.40 (1H, s), 8.10-8.27 (2H, m), 9.04 (1H, s); ESI MS m/z 217 [C10H12N6+H]+; HPLC (Method A) >99% (AUC), tR=9.01 min.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 h
  3. filtrationthe precipitate was filtered
  4. washrinsed with ethanol and diethyl ether
  5. customdried under vacuum at 45° C.

Sources & evidence

ORD record
ord-ea8ba445279a461ca1eab23e704a9187
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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