Water → HCID 22416529, compound

HRID 1720881Notes

Reaction equation

HRID 1720881 reaction equation
[C:1]([C:8]1[NH:9][CH:10]=[CH:11]N=1)([C:3]1NC=CN=1)=O.[NH2:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([CH3:23])[CH:18]=[CH:17]2.[OH2:24]>ClCCl.CN(C)C=O>[CH3:23][N:19]1[C:20]2[C:16](=[CH:15][C:14]([NH:13][C:18]([NH:19][C:20]3[CH:16]=[CH:15][CH:3]=[C:1]4[C:21]=3[CH:11]=[CH:10][N:9]=[CH:8]4)=[O:24])=[CH:22][CH:21]=2)[CH:17]=[CH:18]1

Participants

6

Reactant 3

HCID 962WaterHCID 27695641-methyl-1H-indol-5-amineHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

Product 1

HCID 22416529HCID 22416529, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of carbonyl diimidazole (0.31 g, 2.15 mmol) in dichloromethane (20 ml) was added 5-aminosioquinoline (0.25 g, 1.7 mmol) in dichloromethane (20 ml). After stirring at room temperature for 0.5 h, the solution was evaporated to dryness. The residue was taken up in dimethylformamide (20 ml) and to this solution was added 5-amino-1-methyl-indole (D2) (0.25 g, 1.7 mmol) in dimethylformamide (20 ml). The reaction mixture was heated to 90° C. for 1 h, then cooled and added dropwise to water, with vigorous stirring. The resulting suspension was filtered off, washed with water and dried in vacuo to yield the title compound in 53% yield, m.p. 254°-259° C.

Workup

  1. customthe solution was evaporated to dryness
  2. temperatureThe reaction mixture was heated to 90° C. for 1 h
  3. temperaturecooled
  4. filtrationThe resulting suspension was filtered off
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-7fd44b51d7634f3489c06d15dd2559d6
Source dataset
uspto-grants-1996_04
Patent number
US05508288

Reaction notes

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