Water → HCID 14368349, compound

HRID 1762209Notes

Reaction equation

HRID 1762209 reaction equation
[OH:1][C:2]1[C:3]2[N:4]([C:8]([CH2:12][C:13]#[CH:14])=[C:9]([CH3:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:21][C:22]1[C:27]([CH2:28]Cl)=[C:26]([NH:30][C:31]([NH2:33])=[O:32])[CH:25]=[CH:24][CH:23]=1.O>CN(C)C=O>[CH3:11][C:9]1[N:10]=[C:3]2[C:2]([O:1][CH2:28][C:27]3[C:22]([CH3:21])=[CH:23][CH:24]=[CH:25][C:26]=3[NH:30][C:31]([NH2:33])=[O:32])=[CH:7][CH:6]=[CH:5][N:4]2[C:8]=1[CH2:12][C:13]#[CH:14]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 143683478-Hydroxy-2-methyl-3-(2-propynyl)imidazo[1,2-a]pyridineHCID 14368348HCID 14368348, compound

Product 1

HCID 14368349HCID 14368349, compoundYield 12.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 8-hydroxy-2-methyl-3-(2-propynyl) imidazo-[1,2-a]pyridine (0.571 g) and potassium carbonate (0.424 g) in N,N-dimethylformamide (11.5 ml) was stirred at room temperature for 20 minutes under a nitrogen atmosphere and then 6-methyl-2-ureidobenzyl chloride (0.6 g) was added. After being stirred for 2.5 hours. The mixture was poured into water and the resulting precipitates were collected by filtration. The crude product was purified by column chromatography on silica gel (25 g) with a mixture of chloroform and methanol (100:1 to 100:4) as eluents to give 2-methyl-8-(6-methyl-2-ureidobenzyloxy)-3-(2-propynyl)imidazo[1,2-a]pyridine (0.13 g).

Workup

  1. stirringAfter being stirred for 2.5 hours
  2. customthe resulting precipitates
  3. filtrationwere collected by filtration
  4. customThe crude product was purified by column chromatography on silica gel (25 g) with a mixture of chloroform and methanol (100:1 to 100:4) as eluents

Sources & evidence

ORD record
ord-84b7024eef6a4200b59c8a635a4093fa
Source dataset
uspto-grants-1989_05
Patent number
US04831041

Reaction notes

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