Carbamimidoylazanium Chloride → HCID 178456450, compound

HRID 733217Notes

Reaction equation

HRID 733217 reaction equation
CC(C)([O-])C.[K+].[Cl-].[NH2:8][C:9]([NH2:11])=[NH2+:10].[CH:12]([N:15]1[C:23](=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]1[CH2:25][C:26](OCC)=[O:27])([CH3:14])[CH3:13]>O>[CH:12]([N:15]1[C:23](=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]1[CH2:25][C:26]([NH:10][C:9]([NH2:11])=[NH:8])=[O:27])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 5460839Carbamimidoylazanium ChlorideHCID 23665647Potassium tert-butoxideHCID 86591361HCID 86591361, compound

Product 1

HCID 178456450HCID 178456450, compoundYield 6.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

N-[(2-Isopropyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine is prepared as described in Example 1, starting with 1.5 g of potassium tert-butoxide, 1.3 g of guanidinium chloride and 0.7 g of ethyl (2-isopropyl-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 30 cm3 of water. The aqueous phase is extracted with 3 times 50 cm3 of ethyl acetate and is then concentrated to dryness under reduced pressure (0.6 kPa) at a temperature in the region of 45° C. The residue is taken up in water, triturated and filtered. The solid is taken up in a mixture of dichloromethane/methanol (90/10 by volume) and filtered, and the filtrate is purified by chromatography under argon pressure (60 kPa), on a column of silica gel (particle size 15-40 μm), eluting with a dichloromethane/methanol mixture (90/10 by volume). The fractions comprising the expected product are combined and concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. 0.05 g of N-[(2-isopropyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine is thus obtained in the form of a white solid. Mass spectrum EI: m/e 274 (M+), m/e 187, m/e 132. Infrared spectrum (KBr): 3412; 1974; 1667; 1603; 1531; 1367 and 698 cm−1.

Workup

  1. customN-[(2-Isopropyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine is prepared
  2. extractionThe aqueous phase is extracted with 3 times 50 cm3 of ethyl acetate
  3. concentrationis then concentrated to dryness under reduced pressure (0.6 kPa) at a temperature in the region of 45° C
  4. customtriturated
  5. filtrationfiltered
  6. additionThe solid is taken up in a mixture of dichloromethane/methanol (90/10 by volume)
  7. filtrationfiltered
  8. customthe filtrate is purified by chromatography under argon pressure (60 kPa)
  9. washon a column of silica gel (particle size 15-40 μm), eluting with a dichloromethane/methanol mixture (90/10 by volume)
  10. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-ffbc55fb483a436596971425512fad9e
Source dataset
uspto-grants-2009_09
Patent number
US07589117B2

Reaction notes

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