Hydrochloric Acid → HCID 15225718, compound

HRID 128998Notes

Reaction equation

HRID 128998 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]([CH3:10])[C:8]3=[N:11][C:12]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[C:13]([CH2:14][C:15](O)=[O:16])[N:7]3[C:6]=2[CH:24]=1.[CH3:25][NH2:26].Cl>O1CCCC1>[CH3:25][NH:26][C:15](=[O:16])[CH2:14][C:13]1[N:7]2[C:8]([N:9]([CH3:10])[C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:24][C:6]=32)=[N:11][C:12]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 15222252HCID 15222252, compound

Product 1

HCID 15225718HCID 15225718, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 1.5 g (0.0047 mol) of 6,9-dimethyl-2-phenyl-9H-imidazo[1,2-a]benzimidazole-3-acetic acid is prepared in 50 ml of dry tetrahydrofuran, 1.22 g (0.0075 mol) of N,N'-carbonyldiimidazole are added thereto and the mixture is stirred for 2 h. The solution obtained is treated with an excess of dry gaseous methylamine and stirred for several hours. The solvent is evaporated under reduced pressure. The residue is taken up in water and the solid residue is isolated by filtration. After drying, the product is purified by silica gel column chromatography, eluting with a dichloromethane/methanol 95/5 mixture. The product obtained is then treated with a hydrochloric acid solution. The precipitate is collected by filtration and treated with an excess of ammonium hydroxide up to a pH of 9 to 10. A solid is isolated which is washed with water and dried. 0.79 g of product is obtained. Melting point: 251°-253° C.

Workup

  1. customThe solution obtained
  2. stirringstirred for several hours
  3. customThe solvent is evaporated under reduced pressure
  4. customthe solid residue is isolated by filtration
  5. customAfter drying
  6. customthe product is purified by silica gel column chromatography
  7. washeluting with a dichloromethane/methanol 95/5 mixture
  8. customThe product obtained
  9. filtrationThe precipitate is collected by filtration
  10. additiontreated with an excess of ammonium hydroxide up to a pH of 9 to 10
  11. customA solid is isolated which
  12. washis washed with water
  13. customdried

Sources & evidence

ORD record
ord-5be1d03b6a7945318e95d3d4d6791c59
Source dataset
uspto-grants-1995_11
Patent number
US05466706

Reaction notes

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