Water → (Z)-8-[(3-methoxy-1H-pyrrol-2-yl)methylene]-3,6,7,8-tetrahydro-pyrrolo-[3,2-e]benzimidazol-7-one

HRID 1859076Notes

Reaction equation

HRID 1859076 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:15][CH:16]=[CH:17][C:18]=1[O:19][CH3:20])/[C:5](=[O:12])[NH:6]2.Cl.[CH:22](N)=N.O>C(O)C>[CH3:20][O:19][C:18]1[CH:17]=[CH:16][NH:15][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:22]=[N:1][C:2]=3[C:3]\1=2

Participants

5

Reactant 3

HCID 962WaterHCID 10313058Methanimidamide, hydrochloride (1:1)HCID 15512603(Z)-4,5-diamino-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one

Product 1

HCID 9795685(Z)-8-[(3-methoxy-1H-pyrrol-2-yl)methylene]-3,6,7,8-tetrahydro-pyrrolo-[3,2-e]benzimidazol-7-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (Z)-4,5-diamino-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (60 mg, 0.22 mmol) (from Example 15 above) and formamidine hydrochloride (177 mg, 2.2 mmol) (Aldrich) in ethanol (3 mL) was heated at reflux for 45 min. The mixture was cooled to room temperature, and water was slowly added to induce precipitation. The precipitate was collected by suction filtration, washed with water and dried in a vacuum oven overnight to give (Z)-8-[(3-methoxy-1H-pyrrol-2-yl)methylene]-3,6,7,8-tetrahydro-pyrrolo-[3,2-e]benzimidazol-7-one. (Yield 48 mg, 99%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 45 min
  3. customprecipitation
  4. filtrationThe precipitate was collected by suction filtration
  5. washwashed with water
  6. customdried in a vacuum oven overnight

Sources & evidence

ORD record
ord-7fe690faeb1c4f209767e0d7526cc9af
Source dataset
uspto-grants-2000_11
Patent number
US06153634

Reaction notes

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