Hydrochloric Acid → HCID 178449884, compound

HRID 1821882Notes

Reaction equation

HRID 1821882 reaction equation
[CH3:1][CH:2]([CH3:14])[C:3]([C:5]1[NH:13][C:8]2=[CH:9][N:10]=[CH:11][CH:12]=[C:7]2[CH:6]=1)=O.[C:15]([NH:18][NH2:19])([NH2:17])=[NH:16].[ClH:20].Cl>C(O)C>[ClH:20].[ClH:20].[CH3:1][CH:2]([CH3:14])[C:3](=[N:19][NH:18][C:15]([NH2:17])=[NH:16])[C:5]1[NH:13][C:8]2=[CH:9][N:10]=[CH:11][CH:12]=[C:7]2[CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 578935262-methyl-1-(1H-pyrrolo[2,3-c]pyridin-2-yl)-1-propanoneHCID 178418668HCID 178418668, compound

Product 1

HCID 178449884HCID 178449884, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-methyl-1-(1H-pyrrolo[2,3-c]pyridin-2-yl)-1-propanone (Example 80) (100 mg, 0.53 mmol) in ethanol (5 mL) were added aminoguanidine hydrochloride (58 mg, 0.53 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. Purification by column chromatography (silica gel, 5 to 20% methanol in methylene chloride) produced [[2-methyl-1-(1H-pyrrolo[2,3-c]pyridin-2-yl)propylidene]amino]guanidine dihydrochloride (28 mg, 26%) as a yellow solid: mp 242-245° C.; 1H NMR (500 MHz, CD3OD) δ 1.49 (6H, d, J=7.1 Hz), 3.50-3.54 (1H, m), 7.15 (1H, s), 7.72 (1H, d, J=5.5 Hz), 8.11 (1H, d, J=5.6 Hz), 8.77 (1H, s); ESI MS m/z 245 [C12H16N6+H]+; HPLC (Method A) >99% (AUC) tR=11.9 min.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux under N2
  3. temperatureheating
  4. customwas terminated
  5. customPurification by column chromatography (silica gel, 5 to 20% methanol in methylene chloride)

Sources & evidence

ORD record
ord-8cbe822b496548dfa5305bda3f5de4c8
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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