Methanimidamide, hydrochloride (1:1) → HCID 178433221, compound

HRID 1859075Notes

Reaction equation

HRID 1859075 reaction equation
[NH2:1][C:2]1[C:10]([NH2:11])=[CH:9][CH:8]=[C:7]2[C:3]=1/[C:4](=[CH:13]/[C:14]1[NH:18][CH:17]=[N:16][C:15]=1[CH3:19])/[C:5](=[O:12])[NH:6]2.Cl.[CH:21](N)=N>C(O)C>[CH3:19][C:15]1[N:16]=[CH:17][NH:18][C:14]=1/[CH:13]=[C:4]1\[C:5](=[O:12])[NH:6][C:7]2[CH:8]=[CH:9][C:10]3[NH:11][CH:21]=[N:1][C:2]=3[C:3]\1=2

Participants

4

Reactant 2

HCID 10313058Methanimidamide, hydrochloride (1:1)HCID 178433244(Z)-4,5-diamino-1,3-dihydro-3-[(4-methyl-1H-imidazol-5-yl)methylene]-2H-indol-2-one

Product 1

HCID 178433221HCID 178433221, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (Z)-4,5-diamino-1,3-dihydro-3-[(4-methyl-1H-imidazol-5-yl)methylene]-2H-indol-2-one (30 mg, 0.1175 mmol) (from Example 45 above) and formamidine hydrochloride (95 mg, 1.18 mmol) (Aldrich) in ethanol (1.5 mL) was heated at reflux for 1 h. The mixture was cooled to r.t., and the reaction was quenched with water. The aqueous layer was extracted with dichloromethane. The combined organic layers were washed with brine, dried over anhydrous Mg2SO4 and concentrated under reduced pressure. The crude oily residue was triturated with ether and the resulting yellow precipitate was collected by suction filtration. (First crop; yield 5 mg, 16%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. customthe reaction was quenched with water
  4. extractionThe aqueous layer was extracted with dichloromethane
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous Mg2SO4
  7. concentrationconcentrated under reduced pressure
  8. customThe crude oily residue was triturated with ether
  9. filtrationthe resulting yellow precipitate was collected by suction filtration

Sources & evidence

ORD record
ord-fc90d7d574044680a9cefbf43f7b7354
Source dataset
uspto-grants-2000_11
Patent number
US06153634

Reaction notes

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