Hydrochloric Acid → HCID 15222246, compound

HRID 129001Notes

Reaction equation

HRID 129001 reaction equation
[Cl: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]([OH:17])=O)[N:7]3[C:6]=2[CH:24]=1.[CH3:25][NH2:26].Cl>O1CCCC1>[Cl: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:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)=[C:13]([CH2:14][C:15]([NH:26][CH3:25])=[O:17])[N:7]3[C:6]=2[CH:24]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 15222255HCID 15222255, compound

Product 1

HCID 15222246HCID 15222246, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 1.5 g (0.044 mol) of 6-chloro-9-methyl-2-phenyl-9H-imidazo[1,2-a]benzimidazole-3-acetic acid is prepared in 50 ml of dry tetrahydrofuran, 1.15 g (0.071 mol) of N,N'-carbonyldiimidazole are added thereto and the mixture is stirred for 18 h. The solution is then treated with an excess of dry gaseous methylamine and again stirred for 6 h. The solvent is evaporated under reduced pressure. The residue is treated with water, sodium bicarbonate solution and again with water. The insoluble matter is collected by filtration and dried. It is purified by silica gel column chromatography, eluting with a dichloromethane/methanol 97/3 mixture. The product obtained is treated with a hydrochloric acid solution. The precipitate is collected by filtration and treated with excess of ammonium hydroxide. The product obtained is recrystallized from an N,N-dimethylformamide/water 75/25 mixture and then dried at 100° C. under vacuum. 0.8 g of solid is obtained. Melting point: 272°-273.5° C. (decomposition).

Workup

  1. stirringagain stirred for 6 h
  2. customThe solvent is evaporated under reduced pressure
  3. additionThe residue is treated with water, sodium bicarbonate solution and again with water
  4. filtrationThe insoluble matter is collected by filtration
  5. customdried
  6. customIt is purified by silica gel column chromatography
  7. washeluting with a dichloromethane/methanol 97/3 mixture
  8. customThe product obtained
  9. filtrationThe precipitate is collected by filtration
  10. additiontreated with excess of ammonium hydroxide
  11. customThe product obtained
  12. customis recrystallized from an N,N-dimethylformamide/water 75/25 mixture
  13. customdried at 100° C. under vacuum

Sources & evidence

ORD record
ord-3a78b1651a26464da9f5e53279be0a5d
Source dataset
uspto-grants-1995_11
Patent number
US05466706

Reaction notes

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