1-methyl-1H-imidazole-4-carboxylic acid → HCID 86690490, compound

HRID 1026764Notes

Reaction equation

HRID 1026764 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.[C:33]1([C:39]2[CH:44]=[CH:43][N:42]=[C:41]([CH2:45][NH:46][CH2:47][CH2:48][CH3:49])[CH:40]=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CN(C)C=O>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]([N:46]([CH2:45][C:41]2[CH:40]=[C:39]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH:44]=[CH:43][N:42]=2)[CH2:47][CH2:48][CH3:49])=[O:9])[N:4]=[CH:3]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 86690482HCID 86690482, compound

Product 1

HCID 86690490HCID 86690490, compoundYield 27.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of methyl-1H-imidazole-4-carboxylic acid (53 mg) in dimethylformamide (1 mL) was added 1-hydroxybenzotriazole hydrate (HOBT.H2O) (64 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC.HCl) (81 mg) and the mixture was stirred at room temperature for 10 min. A solution of N-[(4-phenylpyridin-2-yl)methyl]propan-1-amine (80 mg) in dimethylformamide (2 mL) was added thereto, and the mixture was stirred at room temperature overnight. The solvent was distilled off under reduced pressure and then saturated aqueous sodium hydrogen carbonate solution was added, followed by extraction with ethyl acetate. The organic phase was collected and dried over anhydrous sodium sulfate. After the desiccant was filtered off, 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=100:0-90:10) to afford the title compound (33 mg).

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. distillationThe solvent was distilled off under reduced pressure
  3. additionsaturated aqueous sodium hydrogen carbonate solution was added
  4. extractionfollowed by extraction with ethyl acetate
  5. customThe organic phase was collected
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationAfter the desiccant was filtered off
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe resulting residue was purified by column chromatography (silica gel cartridge, chloroform:methanol=98:2-82:18)

Sources & evidence

ORD record
ord-b84fd62af1a84343b87b609f6fea678c
Source dataset
uspto-grants-2014_05
Patent number
US08729271B2

Reaction notes

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