Water → HCID 178437449, compound

HRID 1728583Notes

Reaction equation

HRID 1728583 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:20]3=[N:21][CH:22]=[CH:23][C:24]([CH3:25])=[C:19]3[N:18]=[C:17]2[CH2:26][CH3:27])=[CH:11][CH:10]=1)#[N:2].[N-:28]=[N+:29]=[N-:30].[Na+].Cl.C(N(CC)CC)C.O>CN1CCCC1=O>[CH2:26]([C:17]1[N:16]([CH2:15][C:12]2[CH:13]=[CH:14][C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[C:1]3[NH:30][N:29]=[N:28][N:2]=3)=[CH:10][CH:11]=2)[C:20]2=[N:21][CH:22]=[CH:23][C:24]([CH3:25])=[C:19]2[N:18]=1)[CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 152888043-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethyl-7-methyl-3H-imidazo[4,5-b]pyridine

Product 1

HCID 178437449HCID 178437449, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

10 g (0.027M) of 3-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethyl-7-methyl-3H-imidazo[4,5-b]pyridine, 5.3 g (0.081M) of sodium azide and 5.6 g (0.041M) of triethylamine hydrochloride were suspended in 70 ml of N-methylpyrrolidone. The temperature of an oil bath was raised to 150° to 160° C. over a period of 20 min while stirring with a stirrer. The temperature was returned to room temperature after 6 hr, and water was added thereto. The mixture was washed with ethyl acetate (50 ml×3). The watery phase was acidified with acetic acid and extracted with ethyl acetate (100 ml×5). The extract was dried over magnesium sulfate, and the solvent was distilled off in vacuo. The blackish brown oleaginous substance as the residue was purified by medium pressure column chromatography (SiO2, ACOEt:EtOH=40:1~20:1~10:1). The yield was 11 g. Brown oleaginous substance.

Workup

  1. temperatureThe temperature of an oil bath was raised to 150° to 160° C. over a period of 20 min
  2. washThe mixture was washed with ethyl acetate (50 ml×3)
  3. extractionextracted with ethyl acetate (100 ml×5)
  4. dry with materialThe extract was dried over magnesium sulfate
  5. distillationthe solvent was distilled off in vacuo
  6. customThe blackish brown oleaginous substance as the residue was purified by medium pressure column chromatography (SiO2, ACOEt:EtOH=40:1~20:1~10:1)

Sources & evidence

ORD record
ord-e52e5a367d3c4485a10fad396133e400
Source dataset
uspto-grants-1994_07
Patent number
US05328911

Reaction notes

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