Guanidine Hydrochloride → HCID 178504650, compound

HRID 733280Notes

Reaction equation

HRID 733280 reaction equation
CC([O-])(C)C.[K+].Cl.[NH2:8][C:9]([NH2:11])=[NH:10].C([O:14][C:15](=O)[CH2:16][CH:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([S:26]([CH3:29])(=[O:28])=[O:27])[CH:24]=2)[C:19](=[O:30])[N:18]1[CH2:31][C:32]([F:35])([F:34])[F:33])C>C([O-])(O)=O.[Na+]>[CH3:29][S:26]([C:23]1[CH:24]=[C:25]2[C:20]([C:19](=[O:30])[N:18]([CH2:31][C:32]([F:34])([F:35])[F:33])[C@H:17]2[CH2:16][C:15]([NH:10][C:9]([NH2:11])=[NH:8])=[O:14])=[CH:21][CH:22]=1)(=[O:27])=[O:28]

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 23665647Potassium tert-butoxideHCID 69052429HCID 69052429, compound

Product 1

HCID 178504650HCID 178504650, compoundYield 24.6%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

1.6 g of KOtBu were dissolved using 22 ml of DMF(anhydrous). This solution was added to a solution prepared of 1.5 g guanidine-hydrochloride using 15 ml of DMF(anhydrous). The mixture was stirred for 30 minutes at ambient temperature. Then, a solution prepared of 1.1 g [6-methanesulfonyl-3-oxo-2-(2,2,2-trifluoro-ethyl)-2,3-dihydro-1H-isoindol-1-yl]-acetic acid ethyl ester using 15 ml DMF(anhydrous) was added. The reaction mixture was stirred at ambient temperature for 22 h. Afterwards, the mixture was taken up in 500 ml of semisaturated aqueous NaHCO3 solution and extracted twice using 200 ml of ethyl acetate each time. The EA layer was dried over Na2SO4 and the solvent was removed in vacuo. Chromatography on silica gel using EA/MeOH 3:1 yielded 0.28 g of an amorphous solid (Rf(EA/MeOH 3:1)=0.15; MS (ES+): 393 (M+1)+).

Workup

  1. additionThis solution was added to a solution
  2. additionwas added
  3. stirringThe reaction mixture was stirred at ambient temperature for 22 h
  4. extractionextracted twice
  5. dry with materialThe EA layer was dried over Na2SO4
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-79f6704e1f4f4c2783d46ca5120d0d06
Source dataset
uspto-grants-2009_09
Patent number
US07589117B2

Reaction notes

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