Acetic Acid → HCID 18923584, compound

HRID 1290195Notes

Reaction equation

HRID 1290195 reaction equation
[NH2:1][CH2:2][C:3]([N:5]([C:7]1[C:8]([Cl:27])=[C:9]([C:23]([Cl:26])=[CH:24][CH:25]=1)[CH2:10][O:11][C:12]1[C:13]2[N:14]([C:18]([Br:22])=[C:19]([CH3:21])[N:20]=2)[CH:15]=[CH:16][CH:17]=1)[CH3:6])=[O:4].C(O)(=O)C.[O-:32][C:33]#[N:34].[Na+]>O>[Br:22][C:18]1[N:14]2[CH:15]=[CH:16][CH:17]=[C:12]([O:11][CH2:10][C:9]3[C:23]([Cl:26])=[CH:24][CH:25]=[C:7]([N:5]([CH3:6])[C:3](=[O:4])[CH2:2][NH:1][C:33]([NH2:34])=[O:32])[C:8]=3[Cl:27])[C:13]2=[N:20][C:19]=1[CH3:21]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 517096Sodium CyanateHCID 10790603HCID 10790603, compound

Product 1

HCID 18923584HCID 18923584, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 8-[3-(N-glycyl-N-methylamino)-2,6-dichlorobenzyloxy]-3-bromo-2-methylimidazo[1,2-a]pyridine (100 mg), acetic acid (0.5 ml) and water (1.0 ml) was added an aqueous solution (1 ml) of sodium cyanate (138 mg) at 40° C. The mixture was stirred at the same temperature for 1 hour and evaporated in vacuo. The residue was partitioned into dichloromethane and a saturated aqueous solution of sodium hydrogen carbonate and the organic layer was separated. The aqueous layer was extracted with dichloromethane twice. The combined organic layers were washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin-layer chromatography (dichloromethane:methanol=10:1, V/V) followed by crystallization from ethyl acetate-diethyl ether to give 3-bromo-8-[2,6-dichloro-3-[N-methyl-N-(ureidoacetyl)amino]benzyloxy]-2-methylimidazo[1,2-a]pyridine (72 mg) as crystals.

Workup

  1. customevaporated in vacuo
  2. customThe residue was partitioned into dichloromethane
  3. customa saturated aqueous solution of sodium hydrogen carbonate and the organic layer was separated
  4. extractionThe aqueous layer was extracted with dichloromethane twice
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by preparative thin-layer chromatography (dichloromethane:methanol=10:1, V/V)
  9. customfollowed by crystallization from ethyl acetate-diethyl ether

Sources & evidence

ORD record
ord-6a200689defb4660bd13079e8eb8b838
Source dataset
uspto-grants-1998_05
Patent number
US05750699

Reaction notes

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