1-methyl-1H-imidazole-4-carboxylic acid → HCID 86690468, compound

HRID 1026745Notes

Reaction equation

HRID 1026745 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]([OH:9])=O)[N:4]=[CH:3]1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[Br:33][C:34]1[CH:39]=[C:38]([CH2:40][NH:41][CH:42]([CH3:44])[CH3:43])[CH:37]=[CH:36][N:35]=1>C(#N)C>[Br:33][C:34]1[CH:39]=[C:38]([CH2:40][N:41]([CH:42]([CH3:44])[CH3:43])[C:7]([C:5]2[N:4]=[CH:3][N:2]([CH3:1])[CH:6]=2)=[O:9])[CH:37]=[CH:36][N:35]=1

Participants

6

Reactant 4

HCID 5415091-methyl-1H-imidazole-4-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 53385538N-[(2-Bromopyridin-4-yl)methyl]propan-2-amine

Product 1

HCID 86690468HCID 86690468, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

After a solution of methyl-1H-imidazole-4-carboxylic acid (1.45 g), 1-hydroxybenzotriazole hydrate (HOBT.H2O) (2.08 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC.HCl) (2.60 g) in acetonitrile (35 mL) was stirred at room temperature for 10 min, a solution of N-[(2-bromopyridin-4-yl)methyl]propan-2-amine (2.59 g) in acetonitrile (15 mL) was added thereto, and the resulting solution was then stirred at room temperature for 23 hr. The solvent was distilled off under reduced pressure, and the residue was then diluted with chloroform and washed with saturated aqueous sodium hydrogen carbonate solution. After extracting with chloroform, the solvent was distilled off under reduced pressure. The resulting residue was purified by column chromatography (silica gel cartridge, chloroform:methanol=98:2-82:18) and (the same column, chloroform:methanol=98:2-85:15) to afford the title compound (3.72 g).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionthe residue was then diluted with chloroform
  3. washwashed with saturated aqueous sodium hydrogen carbonate solution
  4. extractionAfter extracting with chloroform
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resulting residue was purified by column chromatography (silica gel cartridge, chloroform:methanol=98:2-82:18)

Sources & evidence

ORD record
ord-3462e7aca3b44dd8b33af1da04cf2f78
Source dataset
uspto-grants-2014_05
Patent number
US08729271B2

Reaction notes

Loading…