Guanidine Hydrochloride → HCID 178457603, compound

HRID 565014Notes

Reaction equation

HRID 565014 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[C:5]1[C:13]([OH:15])=O)(C)C.C(N1[CH:27]=[CH:26]N=C1)(N1C=CN=C1)=O.[ClH:28].[NH2:29][C:30]([NH2:32])=[NH:31].[CH2:33](N(CC)CC)C>CN(C)C=O.O1CCCC1>[ClH:28].[CH:26]([NH:31][C:30]([NH2:32])=[N:29][C:13]([C:5]1[NH:4][C:12]2[C:7]([CH:6]=1)=[CH:8][CH:9]=[CH:10][CH:11]=2)=[O:15])([CH3:27])[CH3:33]

Participants

7

Reactant 4

HCID 5742Guanidine HydrochlorideHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 10536150HCID 10536150, compound

Product 1

HCID 178457603HCID 178457603, compoundYield 47.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A tetrahydrofuran solution, 60 ml, containing 2.00 g (9.84 mmol) of 1-isopropyl-2-indolecarboxylic acid and 2.39 g (14.8 mmol) of carbonyldiimidazole was stirred at room temperature for 2 hours and then at 45 to 50° C. for an hour. After cooling to room temperature, 30 ml of a dimethylformamide solution of 5.64 g (59.0 mmol) of guanidine hydrochloride and 5.97 g (59.0 mmol) of triethylamine was added to the reaction mixture followed by stirring at room temperature for 12 hours. The mixture was then distilled off under reduced pressure and water was added to the resulting residue. After adjusting pH in the range of 5 to 6 with 2N hydrochloric acid, the mixture was extracted three times with ethyl acetate. After drying over anhydrous magnesium sulfate, the extract was acidified with hydrogen chloride/ether. The precipitated crystals were filtered and dried to give 1.31 g (47.4%) of the desired 1-isopropyl-2-indoloyl-guanidine hydrochloride.

Workup

  1. waitat 45 to 50° C. for an hour
  2. temperatureAfter cooling to room temperature
  3. stirringby stirring at room temperature for 12 hours
  4. distillationThe mixture was then distilled off under reduced pressure and water
  5. additionwas added to the resulting residue
  6. extractionthe mixture was extracted three times with ethyl acetate
  7. dry with materialAfter drying over anhydrous magnesium sulfate
  8. filtrationThe precipitated crystals were filtered
  9. customdried

Sources & evidence

ORD record
ord-d44b07e391e744efbbcd17b7859057f1
Source dataset
uspto-grants-2001_01
Patent number
US06169107A

Reaction notes

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