Ethanol → HCID 58398075, compound

HRID 451505Notes

Reaction equation

HRID 451505 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](F)[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]2[N:11]([N:15]=[C:16]([NH:18][CH:19]3[CH2:24][CH2:23][N:22]([C:25]4[CH:30]=[CH:29][N:28]=[C:27](Cl)[CH:26]=4)[CH2:21][CH2:20]3)[N:17]=2)[CH:12]=[CH:13][CH:14]=1.[O-:32][CH2:33][CH3:34].[Na+].[CH3:36][CH2:37][OH:38]>>[Cl:1][C:2]1[CH:7]=[C:6]([O:32][CH2:33][CH3:34])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]2[N:11]([N:15]=[C:16]([NH:18][CH:19]3[CH2:24][CH2:23][N:22]([C:25]4[CH:30]=[CH:29][N:28]=[C:27]([O:38][CH2:37][CH3:36])[CH:26]=4)[CH2:21][CH2:20]3)[N:17]=2)[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 2723922Sodium ethoxide2×HCID 53353814HCID 53353814, compound

Product 1

HCID 58398075HCID 58398075, compoundYield 35%

Conditions

Temperature
60 °C

Procedure

To a solution of 8-(2-chloro-4-fluorophenyl)-N-(1-(2-chloropyridin-4-yl)piperidin-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine (example 58) (46 mg, 0.10 mmol) in EtOH (1 mL) was added sodium ethoxide solution (21% in ethanol, 56 L, 0.15 mmol) and the reaction mixture was stirred under Argon in a sealed tube at 60° C. for 16 h. After cooling to room temperature the mixture was heated in the microwave to 150° C. for 45 minutes and then sodium ethoxide solution (21% in ethanol, 56 uL, 0.15 mmol) was added and the mixture heated to 150° C. for another 30 in the microwave. The mixture was then evaporated and diluted with water and extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and evaporated. Purification by chromatography (silica gel, 20 g, 0 to 100% ethyl acetate in heptane) afforded the title compound (17 mg, 35%) as a white foam.

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. temperaturewas heated in the microwave to 150° C. for 45 minutes
  3. temperaturethe mixture heated to 150° C. for another 30 in the microwave
  4. customThe mixture was then evaporated
  5. additiondiluted with water
  6. extractionextracted with ethyl acetate
  7. dry with materialThe combined organic phases were dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customPurification by chromatography (silica gel, 20 g, 0 to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-d8905f3456364e04aeaf81f55b6df393
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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