Imidazole → 1-Ethyl-3-[7-pyridin-3-yl-5-(pyrrolidine-1-carbonyl)-imidazo[1,2-a]pyridin-2-yl]-urea

HRID 2112960Notes

Reaction equation

HRID 2112960 reaction equation
N1C=CN=[CH:2]1.C(O[C:9]([C:11]1[N:16]2N=[C:18]([NH:20][C:21]([NH:23][CH2:24][CH3:25])=[O:22])[N:19]=[C:15]2[CH:14]=[C:13]([C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[CH:12]=1)=[O:10])C.[NH:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1>>[CH2:24]([NH:23][C:21]([NH:20][C:18]1[N:19]=[C:15]2[CH:14]=[C:13]([C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)[CH:12]=[C:11]([C:9]([N:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)=[O:10])[N:16]2[CH:2]=1)=[O:22])[CH3:25]

Participants

4

Reactant 3

HCID 795ImidazoleHCID 31268Pyrrolidine2×HCID 576431092-(3-Ethyl-ureido)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethyl ester

Product 1

HCID 688393861-Ethyl-3-[7-pyridin-3-yl-5-(pyrrolidine-1-carbonyl)-imidazo[1,2-a]pyridin-2-yl]-urea

Conditions

Temperature
23 °C

Procedure

A dry mixture of imidazole (2 g) and 2-(3-ethyl-ureido)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethyl ester (which may be produced as described in Example 16, Step 1) (0.160 g, 0.452 mmol) was heated until it became a homogeneous melt. It was then allowed to cool and solidify. To the solid was added pyrrolidine (0.1 mL) and the mixture was heated until it became a homogeneous melt, then allowed to cool to 23° C. Additional pyrrolidine (0.1 mL) was added and the reaction was heated at melt temperature for 30 sec. The reaction was cooled to RT and allowed to solidify. The solid was partitioned between water and EtOAc and the aqueous layer was extracted EtOAc (3×15 mL). The combined organic layers were then washed with brine and dried over sodium sulfate. Evaporation in vacuo gave a solid that was purified by silica gel chromatography (gradient elution 2-30% isopropanol/dichloromethane) to give the desired product. MS (APCI+)=380.1

Workup

  1. temperaturewas heated until it
  2. temperatureto cool
  3. temperaturethe mixture was heated until it
  4. temperaturethe reaction was heated
  5. customfor 30 sec
  6. temperatureThe reaction was cooled to RT
  7. customThe solid was partitioned between water and EtOAc
  8. extractionthe aqueous layer was extracted EtOAc (3×15 mL)
  9. washThe combined organic layers were then washed with brine
  10. dry with materialdried over sodium sulfate
  11. customEvaporation in vacuo
  12. customgave a solid
  13. customthat was purified by silica gel chromatography (gradient elution 2-30% isopropanol/dichloromethane)

Sources & evidence

ORD record
ord-8d609774dce449c5a0fef5244d620afa
Source dataset
uspto-grants-2009_04
Patent number
US07524860B2

Reaction notes

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