Potassium Carbonate → HCID 18409419, compound

HRID 963022Notes

Reaction equation

HRID 963022 reaction equation
[C:1]([NH:9][C:10]1[N:11]=[CH:12][N:13]([CH2:15][CH2:16][CH2:17][CH2:18][C:19]2([C:32]([NH:34][CH2:35][C:36]([F:39])([F:38])[F:37])=[O:33])[C:31]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:25]3[C:20]2=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:40]C1NC([N+]([O-])=O)=CN=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:1]([NH:9][C:10]1[N:11]=[C:12]([CH3:40])[N:13]([CH2:15][CH2:16][CH2:17][CH2:18][C:19]2([C:32]([NH:34][CH2:35][C:36]([F:38])([F:37])[F:39])=[O:33])[C:31]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:25]3[C:20]2=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 127602-Methyl-5-nitroimidazoleHCID 18409234HCID 18409234, compound

Product 1

HCID 18409419HCID 18409419, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solid mixture of Example 273 Part A(2) compound (1.00 g, 2.35 mmoL), 2-methyl-5-nitroimidazole (400 mg, 3.15 mmol), and K2CO3 (2.82 mmol) was added DMF (5 mL) and the mixture was stirred at room temperature for 3 days. The reaction was partitioned between EtOAc and saturated NaHCO3 and the organic layer was washed successively with H2O and brine. The solution was dried (Na2SO4), filtered, and stripped. The residue was triturated with Et2O/EtOAc/hexane to give title compound (973 mg, 88%) as a white solid. mp 145°-147° C.

Workup

  1. customThe reaction was partitioned between EtOAc and saturated NaHCO3
  2. washthe organic layer was washed successively with H2O and brine
  3. dry with materialThe solution was dried (Na2SO4)
  4. filtrationfiltered
  5. customThe residue was triturated with Et2O/EtOAc/hexane

Sources & evidence

ORD record
ord-35c628ecfb8d40fba042d0d306f26c85
Source dataset
uspto-grants-1998_06
Patent number
US05760246

Reaction notes

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