Ethanol → HCID 57855953, compound

HRID 2039620Notes

Reaction equation

HRID 2039620 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([NH2:10])[C:7]([NH:11][CH3:12])=[C:6]([Cl:13])[C:5]=1[NH2:14].Cl.[CH:17]1(C(N)=N)[CH2:19][CH2:18]1.[CH3:23]CO>>[CH3:1][O:2][C:3]([C:4]1[C:5]([NH2:14])=[C:6]([Cl:13])[C:7]2[N:11]([CH3:23])[C:12]([CH:17]3[CH2:19][CH2:18]3)=[N:10][C:8]=2[CH:9]=1)=[O:15]

Participants

4

Reactant 3

HCID 702EthanolHCID 2781916Cyclopropanecarboximidamide hydrochloride3×HCID 57855886HCID 57855886, compound

Product 1

HCID 57855953HCID 57855953, compoundYield 10%

Procedure

To a suspension of 1 g (3.48 mmol) of 2,5-diamino-3-chloro-4-methylamino-benzoic acid methyl ester (synthesis described in example H7) in 153 ml of EtOH, is added 866 mg (6.97 mmol) of cyclopropane carboxamidine hydrochloride. After 24 hours of reaction under reflux, 866 mg (6.97 mmol) of cyclopropane carboxamidine hydrochloride were added more and the reaction is stirred under reflux 2 days more. Again 433 mg (3.48 mmol) of cyclopropane carboxamidine hydrochloride is added and after again 2 days of reaction under reflux, the reaction is stopped and the solvent is evaporated. The residue is suspended in EtOAc and the precipitate is filtrated. The filtrate obtained is evaporated and purified by flash chromatography on silica gel and gives 100 mg (0.36 mmol, 10%) of a brown solid. LC/MS: 280/282 (M+1)+

Workup

  1. customAfter 24 hours of reaction
  2. temperatureunder reflux
  3. temperatureunder reflux 2 days more
  4. temperatureunder reflux
  5. customthe solvent is evaporated
  6. filtrationthe precipitate is filtrated
  7. customThe filtrate obtained
  8. customis evaporated
  9. custompurified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-12ae203fa46f47899809d0218a48c17c
Source dataset
uspto-grants-2013_11
Patent number
US08580785B2

Reaction notes

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