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

HRID 1531160Notes

Reaction equation

HRID 1531160 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-e13297f28a184692a0b0d748dccd68b0
Source dataset
uspto-grants-2001_03
Patent number
US06197804B1

Reaction notes

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