Carbamimidoylazanium Chloride → HCID 178513088, compound

HRID 733219Notes

Reaction equation

HRID 733219 reaction equation
CC(C)([O-])C.[K+].[Cl-].[NH2:8][C:9]([NH2:11])=[NH2+:10].[CH:12]1([CH2:15][N:16]2[C:24](=[O:25])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]2[CH2:26][C:27](OCC)=[O:28])[CH2:14][CH2:13]1>O>[CH:12]1([CH2:15][N:16]2[C:24](=[O:25])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]2[CH2:26][C:27]([NH:10][C:9]([NH2:11])=[NH:8])=[O:28])[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 5460839Carbamimidoylazanium ChlorideHCID 23665647Potassium tert-butoxideHCID 69714143HCID 69714143, compound

Product 1

HCID 178513088HCID 178513088, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

N-[(2-Cyclopropylmethyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine is prepared as described in Example 1, starting with 2.9 g of potassium tert-butoxide, 2.5 g of guanidinium chloride and 1.5 g of ethyl (2-cyclopropylmethyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate. The reaction mixture is stirred at a temperature in the region of 20° C. for 20 hours, followed by addition of 20 cm3 of water. The aqueous phase is extracted with 3 times 100 cm3 of ethyl acetate. The organic extracts are combined and then concentrated to dryness under reduced pressure (0.6 kPa) at a temperature in the region of 35° C. The residue is taken up in water, triturated, filtered off and then dried in a desiccator. 1.2 g of N-[(2-cyclopropylmethyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine are thus obtained in the form of an off-white powder melting at 229° C. Mass spectrum: DCI: m/e 287 (M+H)+.

Workup

  1. customN-[(2-Cyclopropylmethyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine is prepared
  2. extractionThe aqueous phase is extracted with 3 times 100 cm3 of ethyl acetate
  3. concentrationconcentrated to dryness under reduced pressure (0.6 kPa) at a temperature in the region of 35° C
  4. customtriturated
  5. filtrationfiltered off
  6. customdried in a desiccator

Sources & evidence

ORD record
ord-f34c07540850460b861dc019f4761fe0
Source dataset
uspto-grants-2009_09
Patent number
US07589117B2

Reaction notes

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