Ethoxyacetyl chloride → HCID 21913140, compound

HRID 1245949Notes

Reaction equation

HRID 1245949 reaction equation
[CH3:1][C:2]1[C:3]([NH:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][CH2:23][C:24]2[S:25][CH:26]=[CH:27][N:28]=2)=[C:4]([NH2:16])[C:5]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:6][C:7]=1[CH3:8].[CH2:29]([O:31][CH2:32][C:33](Cl)=O)[CH3:30]>N1C=CC=CC=1.Cl.N1C=CC=CC=1>[CH2:29]([O:31][CH2:32][C:33]1[N:17]([CH2:18][CH2:19][O:20][CH2:21][CH2:22][CH2:23][C:24]2[S:25][CH:26]=[CH:27][N:28]=2)[C:3]2[C:2]([CH3:1])=[C:7]([CH3:8])[N:6]=[C:5]([O:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:4]=2[N:16]=1)[CH3:30]

Participants

5

Reactant 2

HCID 84189Ethoxyacetyl chlorideHCID 69193218HCID 69193218, compound

Product 1

HCID 21913140HCID 21913140, compoundYield 76.6%

Reagents, catalysts & solvents 2

HCID 10176127Pyridinium chlorideCatalystHCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

Under a nitrogen atmosphere, a solution of 5,6-dimethyl-2-phenoxy-N4-{2-[3-(1,3-thiazol-2-yl)propoxy]ethyl}pyridine-3,4-diamine (4.12 g, 10.3 mmol) and pyridine hydrochloride (0.024 g, 0.21 mmol) in pyridine (30 mL) was cooled to 7° C. Ethoxyacetyl chloride (1.33 g, 10.9 mmol) was added, and the reaction was stirred for 30 minutes. The cloudy solution was then heated at 100° C. for 20 hours and then allowed to cool to room temperature. The volatiles were removed under reduced pressure, and the residue was partitioned between water and dichloromethane. The organic layer was washed with potassium carbonate (2×50 mL) and brine (2×50 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting oil was triturated with heptane to provide a solid that was isolated by filtration. 2-(Ethoxymethyl)-6,7-dimethyl-4-phenoxy-1-{2-[3-(1,3-thiazol-2-yl)propoxy]ethyl}-1H-imidazo[4,5-c]pyridine (3.68 g) was obtained as a tan solid.

Workup

  1. temperatureto cool to room temperature
  2. customThe volatiles were removed under reduced pressure
  3. customthe residue was partitioned between water and dichloromethane
  4. washThe organic layer was washed with potassium carbonate (2×50 mL) and brine (2×50 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting oil was triturated with heptane
  9. customto provide a solid
  10. customthat was isolated by filtration

Sources & evidence

ORD record
ord-c67e428800bc48609a5ba8f24d02ced0
Source dataset
uspto-grants-2006_10
Patent number
US07125890B2

Reaction notes

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