Potassium Carbonate → HCID 22921578, compound

HRID 2258633Notes

Reaction equation

HRID 2258633 reaction equation
[CH3:1][CH:2]([CH3:30])[CH2:3][N:4]1[C:8]2[CH:9]=[C:10]([N:14]3[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[NH:16][C:15]3=[O:25])[C:11]([F:13])=[CH:12][C:7]=2[N:6]=[C:5]1[C:26]([F:29])([F:28])[F:27].C(=O)([O-])[O-].[K+].[K+].[NH2:37]OS(C1C(C)=CC(C)=CC=1C)(=O)=O>O1CCCC1.O>[NH2:37][N:16]1[C:17]([C:21]([F:24])([F:23])[F:22])=[CH:18][C:19](=[O:20])[N:14]([C:10]2[C:11]([F:13])=[CH:12][C:7]3[N:6]=[C:5]([C:26]([F:27])([F:29])[F:28])[N:4]([CH2:3][CH:2]([CH3:30])[CH3:1])[C:8]=3[CH:9]=2)[C:15]1=[O:25]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamineHCID 22921574HCID 22921574, compound

Product 1

HCID 22921578HCID 22921578, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.3 grams (0.003 mole) of 3-[1-(2-methylpropyl)-2-trifluoromethyl-5-fluorobenzimidazol-6-yl]-6-trifluoromethyluracil (prepared as in Example 2, Steps A-H) in 30 mL of tetrahydrofuran is stirred, and 0.5 gram (0.003 mole) of potassium carbonate, then 0.7 gram (0.003 mole) of 1-aminooxysulfonyl-2,4,6-trimethylbenzene are added. Upon completion of the addition, the reaction mixture is stirred for one hour. The reaction mixture is then diluted with water and extracted with three portions of ethyl acetate. The combined extracts are dried with magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure to a residue, which is purified by column chromatography, yielding 1-amino-3-[1-(2-methylpropyl)-2-trifluoromethyl-5-fluorobenzimidazol-6-yl]-6-trifluoromethyluracil.

Workup

  1. additionUpon completion of the addition
  2. extractionextracted with three portions of ethyl acetate
  3. dry with materialThe combined extracts are dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate is concentrated under reduced pressure to a residue, which
  6. customis purified by column chromatography

Sources & evidence

ORD record
ord-94d6259bd9c04af6b500f90ccacb32dd
Source dataset
uspto-grants-1997_08
Patent number
US05661108

Reaction notes

Loading…