2-Methylimidazole → HCID 66606726, compound

HRID 563536Notes

Reaction equation

HRID 563536 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[CH:5][N:6]=1.[H-].[Na+].[CH2:9]([O:11][C:12](=[O:40])[CH2:13][C:14]1[CH:15]=[C:16]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][C:23]=2[CH2:32][N:33]([C:36](=[O:39])[CH2:37]Cl)[CH2:34][CH3:35])[C:17]([O:20][CH3:21])=[CH:18][CH:19]=1)[CH3:10]>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:9]([O:11][C:12](=[O:40])[CH2:13][C:14]1[CH:15]=[C:16]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:30])([F:31])[F:29])=[CH:24][C:23]=2[CH2:32][N:33]([CH2:34][CH3:35])[C:36](=[O:39])[CH2:37][N:3]2[CH:4]=[CH:5][N:6]=[C:2]2[CH3:1])[C:17]([O:20][CH3:21])=[CH:18][CH:19]=1)[CH3:10]

Participants

6

Reactant 3

HCID 127492-MethylimidazoleHCID 24758Sodium hydride2×HCID 66607317HCID 66607317, compound

Product 1

HCID 66606726HCID 66606726, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent2×

Procedure

To 2-methylimidazole (0.047 g, 0.57 mmol) in DMF (2 mL) at 0° C. was added sodium hydride (60% in mineral oil; 0.031 g, 0.78 mmol), and the reaction was stirred for 15 minutes. (2′-{[(2-Chloro-acetyl)-ethyl-amino]-methyl}-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester (0.52 mmol) was added in DMF, and the reaction was stirred at room temperature for 1.5 hours. Analytical LCMS showed that a lot of starting material remained, so tetrabutylammonium iodide (0.005 g, 0.01 mmol) was added, and the reaction was stirred for 3 hours. Analytical LCMS showed that no change had occurred, so additional sodium hydride (60% in mineral oil; 0.031 g, 0.78 mmol) was added, and the reaction was stirred overnight at room temperature. The mixture was partitioned between EtOAc and H2O, and the aqueous layer was separated and extracted twice with EtOAc. The combined organic layers were washed three times with H2O, and then dried and concentrated to give the title compound.

Workup

  1. stirringthe reaction was stirred at room temperature for 1.5 hours
  2. additionwas added
  3. stirringthe reaction was stirred for 3 hours
  4. stirringthe reaction was stirred overnight at room temperature
  5. customThe mixture was partitioned between EtOAc and H2O
  6. customthe aqueous layer was separated
  7. extractionextracted twice with EtOAc
  8. washThe combined organic layers were washed three times with H2O
  9. customdried
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-db43d30211db475cbc35343d7d39fb68
Source dataset
uspto-grants-2011_11
Patent number
US08067445B2

Reaction notes

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